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Book Summary: Self-Made Boss – Advice, Hacks, and Lessons from Small Business Owners

Self-Made Boss (2022) is a practical starter kit for anyone looking to start a small business. It’s packed with advice and case studies looking at small businesses from across the United States, with step-by-step instructions for turning your great idea into a successful business.

Introduction: Kick-start your journey to self-employment.

Small businesses do so much more than contribute to the economy. They’re a big part of our social fabric: they give neighborhoods character, and they’re part of the lifeblood that holds communities together.

The United States has a lot of small business owners – approximately 30 million, in fact. If you’re looking to join their number and want to set up a small business of your own, then these summaries are for you. If you’ve already struck out on your own and you’re seeking advice and inspiration from other small business owners, they’re for you, too.

You can find a lot of inspirational business books from Fortune 500 CEOs – but what if you own a neighborhood pizza joint and you’re looking to source the best Buffalo mozzarella? Or you just opened a bookstore and you need to build your social media presence? You need practical business advice that’s tailored to your situation.

The authors call this book a starter kit. That means that in these summaries, we won’t be getting into the weeds with many of the topics that might be relevant at various stages in starting a business, like tax strategy or how exactly you set up a profit-and-loss statement. (When it comes to that sort of thing, the details vary a lot based on industry and location anyway.) Instead, we’ll outline the basics of what it takes to become a self-made boss and point you in the right direction for getting started.

[Book Summary] Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners

In these summaries, you’ll learn

  • what a mom-and-pop ice cream shop has to teach all business owners;
  • the two things you can do to weather most business setbacks; and
  • how to create buzz for your business by word-of-mouth.

Get connected with free business resources.

No matter where you are in the world, there are probably free small business resources that you’re not using.

If you’re in the United States, then by all means get in contact with your local branch of the Small Business Administration, or SBA. It just might be the federal government’s best-kept secret!

The SBA is a treasure trove of free resources that far too few entrepreneurs utilize. Don’t make that mistake yourself, and definitely don’t pay expensive consultants for information the SBA gives out for free!

The SBA will help you workshop an idea from the ground up, get a loan, and draw up initial contacts, as well as connect you with the right mentors. Its staff members have probably seen all of your problems before and will help you avoid common pitfalls. So if you haven’t already, find the SBA resources in your state.

Even if you’re not in the US, chances are there are nonprofits, free public resources, and networks in your area that will support you. Your first step should be to get in contact with them.

There are people out there who want to help you. Go and find them!

Outline your vision and articulate your goals by writing a solid business plan.

Let’s not sugarcoat it: starting a small business is risky. You have about a fifty-fifty chance of surviving the first five years; in fact, one small business in five will fold within its first year. To prevent this, it’s absolutely critical to think through your venture systematically. And that’s what a business plan is for.

Now, a business plan is crucial if you’re looking for a grant or a loan. As an outward-facing document, it can help you convince people that you’re taking the venture seriously and that you know what you’re doing.

But even if you’re not looking for external funding, it’s a great idea to write a business plan anyway, even if it’s just for yourself. A business plan is your chance to present your vision for what you’re building and outline your plans for achieving your goals. Simply put, it’s the blueprint for your business. And the act of writing a business plan requires you to research your industry and think objectively about what goals you’re aiming to achieve. The thought process behind it will positively influence your entire business and get you started on the right track. So don’t procrastinate on this one – it isn’t just busywork!

So how do you do it? Fortunately, you won’t need to reinvent the wheel every time – it’s a pretty formulaic process, and there are plenty of resources online – and in the Blinkist library – for the specifics of how to do it. But here are some tips to get you started:

The beginning of your business plan, the executive summary, is your chance to tell your story vividly and engagingly. In it, briefly run through what the rest of your plan lays out in detail, with particular focus on the problem, solution, and audience. Pro tip: the executive summary will go first in the document, but it might be easier to write it last. But whenever you choose to write it, remember – to convince your readers, the executive summary has to be punchy!

Then, for the rest of the document, get much more concrete and objective. Write like a banker, not a poet; back up your claims with evidence and statistics, and don’t make claims you can’t prove – that you make the best sub sandwiches in town, for example. Be selective with your information and be sure to present yourself and your team in the best possible light.

If you’re aiming your business plan at investors, it’s a good idea to hire an accountant to help you make realistic financial projections and to put everything in the format your audience is expecting. And don’t send gimmicks along with the business plan! Investors will gladly eat the baked goods in your gift basket, but the money you spend on those treats isn’t a smart expenditure – they’re unlikely to sway anyone, and they might just make you look less than serious. Just stick to the facts instead.

What’s important is that you succinctly articulate the problem or need you’re looking to address, and why anyone would pay for your solution. Is your potential business not just feasible, but attractive to potential customers? Answering this question for yourself and for potential investors is at the core of a solid business plan.

Take care of your incorporation paperwork and other licensing requirements from the outset.

Unless you’re opening a law firm, chances are, you’re not starting a business in order to do legal paperwork – that isn’t most people’s idea of fun! But if you want your business to be aboveboard, it can’t be avoided. Given that, you might as well knock it out as quickly as possible so you can focus on running your business. It’ll also help you avoid fines or even your business getting shut down later on down the line.

Fortunately, incorporating your business isn’t as painful as it sounds. To begin, you’ll need to decide on your corporate structure. This will determine the parameters of your business and how it will be taxed. Here, we’ll outline the basics so you can get the lay of the land, but it’s a good idea to do your own web research and follow up with a lawyer to get a full picture of the pros and cons of each. Also note that how you incorporate your business might vary from state to state.

First, there’s the simplest form of incorporation: sole proprietorship. This means that only you own the business, and in most cases you only need to file one form, the DBA, or “Doing Business As” form. A sole proprietorship is a pass-through entity, meaning that corporate profits are only taxed once as part of the owner’s income. They’re super easy to set up, so it might make sense to start here and change your structure later if you need to. The downside to a sole proprietorship, though, is that you’re 100% responsible for any business liabilities or debts incurred.

Next up, you have the LLC, or limited liability corporation. It’s a little more complicated than a sole proprietorship, but it’s likely that you can take care of the paperwork in about two hours. The advantages of an LLC are that as many people as you like can own the business and personal assets are protected. Should your business flop, you won’t stand to lose your retirement fund or your house!

If an LLC is sounding like the right option for you, also look into structuring your business as an S corp, which is similar to an LLC except that it has more formalities. An S corp’s advantage over an LLC is that S corps have been around longer, so certain investors, lawyers, and advisors might prefer to work with you.

Finally, if you’re looking to one day raise capital by selling shares of your business, you’ll need to incorporate as a C corporation. A C corp allows for multiple types of stock shares and unlimited shareholders. There’s a disadvantage to it too, though – unlike the other three structures, which are all pass-through entities, a C corp is taxed twice. Given the increased tax burden, don’t set up a C corp unless you’re sure it’s the right option for you.

You’ll need a lawyer to set up an S corp or a C corp, unlike for a sole proprietorship or LLC. But even for those, you can always hire a lawyer – if you’re worried you’re in over your head, that could mean peace of mind.

Finally, be sure to look into what licenses and insurance you need for your industry. An insurance broker can help you with this.

When designing your operational workflows, use observation and standardization to your advantage.

Now let’s get to why you’re really here: learning how to get up and running!

The real question here is: how do you turn your idea into a finished product in the hands of a customer? Essentially, we’re talking about process management of your operations. Small businesses typically have small margins, so the successful ones pay close attention to every aspect of how the company is run. That means getting really specific with the nitty gritty details of your workflows and optimizing for efficiency.

To nail down your operations, use data to your advantage. Take the time to observe and document your operational processes – everything from sourcing materials to inventory management, distribution, and sales processes. Anything that’s done routinely should be standardized and documented, then systematized. A documented, standardized workflow will be hugely helpful in identifying problems or inefficiencies and will help you test new solutions. Plus, having clear and documented workflows will make it easier to train new employees or sell your business to someone else at a later date.

Want an example? Let’s look at Pesso’s Ices & Ice Cream in Bayside, New York, run by a father and a son. The younger Pesso took a long and close look at all aspects of their business – from ingredients to spoon prices to hiring practices – and made educated guesses about how to improve the business.

When he noticed that the shop barely made any money before two o’clock, he decided to change the opening hours. He also ran a full cost analysis and realized that despite ingredient costs rising dramatically in a few years, his shop hadn’t adjusted the prices of their ice cream. He changed the price and sizing of the scoops, and stopped offering less popular menu items like floats, which took more work than scooping ice cream but generated little revenue. A few customers complained, but most didn’t notice. Some even appreciated it, reporting that fewer choices had reduced their decision fatigue. For Pesso, a simpler menu allowed him to focus on quality and also boosted his margins.

Nowadays, Pesso is a small business consultant. Based on his success with the ice cream shop, he advises other business owners to observe your systems first, from multiple angles, then simplify.

The more data you have on your processes, the more easily you’ll be able to go from reactive to predictive. You’ll be able to adapt to changing customer demands more nimbly, because you’ll be able to observe trends. As Mike Bloomberg once quipped, “In God we trust. Everyone else: bring data.”

When building your brand, create a signature experience to generate buzz in your community.

Here’s a fact that every business owner needs to know: seventy percent of purchasing decisions are made based on how a customer feels during a transaction.

As you’re building your business, it’s critical to ensure that your customers feel understood and valued when interacting with your brand. To keep those customers coming back and make you their small business of choice, you want to form a bond based on trust.

One way to do this is to create a signature experience. Think about Ikea for a second. Any trip to the Swedish furniture giant is iconic – it’s always about getting lost in a maze of charmingly arranged rooms that allow you to easily visualize how that Billy bookcase will mesh with your lifestyle. At the end, there’s always a plate of the store’s famous Swedish meatballs waiting for you. From start to finish, the store has created an iconic experience designed to leave a lasting and positive impression.

You don’t need to be the world’s largest furniture retailer to do the same. In fact, designing an engaging experience for your customers is a great opportunity to put love and creativity into your business.

One good example of a small business with a signature experience is the children’s bookstore Wild Rumpus in Minneapolis. It sells books, of course, but it also has cats and chickens running around at all hours of the day, aquariums in the bathrooms, and whimsical exploration areas. Parents love to bring their kids to a place with a memorable experience, and the store’s neighborhood has more character because of it.

Once you’ve given your brand this kind of unique personality, expand on it and publicize it. To begin with, you can create buzz through word of mouth. Giving away products and services is a good way to boost this initially, and you can solicit feedback from these early customers to improve your product.

Next, be sure to build up your web presence from the get-go. Before they even consider walking through your door and giving you their money, most prospective customers will look you up online to see if your business is legitimate. You need to provide them with all the necessary info – your opening hours, for example – but also be sure to tell your story. Who are you, and why’d you decide to go into business? It’s a great opportunity to connect with your customers on a human level.

The authors also recommend investing in design earlier than you might think; a logo goes a long way in establishing your brand identity! If you can afford it, hiring a graphic designer and a photographer from the start is a great way to establish credibility online.

Leveraging social media is also a must. When you have new inventory, weekly specials, and promotions, use the various platforms to share them. It can take some time to grow a social media presence, but make sure you persist. There’s no one-size-fit-all approach to success on social media, but it’s good to start out with a presence on at least one or two platforms and aim to post three to five times per week.

Finally, don’t discount traditional methods of acquiring publicity. You can always place an ad in a local paper or sponsor a community activity for free press coverage. If you’re about to open or have a special event, send out a press release and see if local media is interested in covering it.

To stay ahead of unexpected setbacks, observe consumer trends and be flexible in your approach to business.

Let’s say your business is official and you’ve been around for several months. Customers are regularly coming through the door, and you feel like you’ve nailed down your operational procedures. Maybe you’re even profitable already.

Unfortunately, this smooth sailing probably won’t last long. You’ll likely confront a business disruption that can come in many different forms, ranging from everyday setbacks like traffic jams and unreliable employees to larger-scale issues like changing consumer behavior or world events like wars and pandemics. But don’t lose heart! There are a couple of ways to prepare yourself to roll with the punches.

The first is to be observant. Keep a close eye on your company’s sales information, and compare it to consumer trends and feedback from customers. Some setbacks, like a hurricane, will sneak up on you. But more often, changes that commonly affect business happen gradually. If you learn to read your market and pay attention to trends, you can adapt your business accordingly.

The second is to be flexible. The ability to pivot might be the most important key to success. Keep asking yourself how you can adapt or improve, and stay committed to evolving your business.

Being observant and flexible will help you find new opportunities in business if your initial approach isn’t working. One way is to create an adjacent product if yours isn’t selling for one reason or another. Let’s say that, pre-pandemic, you found success selling homemade festival fashion on Etsy, an online craft marketplace. Your Coachella-ready crop tops were flying off the shelves in 2019, but by the spring of 2020, when pretty much all festivals worldwide were canceled, business wasn’t exactly booming.

In April 2020, the pandemic was well underway and Etsy executives sent a memo to its sellers, suggesting that they all make masks. It was good advice, and you’d have been wise to take it. In just a few short months, mom-and-pop shops sold $500 million worth of masks – a product for which there had previously been almost no demand.

When you encounter your first roadblock, ask yourself whether it’s time to double down on your vision or to recalibrate your approach. Remember to let the data do the talking, and don’t operate solely on gut feelings. Consider reaching out to an expert in your industry to talk about the challenge you’re facing.

Final Summary

If you have an itch to strike out on your own and start a small business, you’re in great company.

Self-made bosses are daring individuals who see problems in the world and decide to become part of the solution. Some are creatives looking to turn passion into a profession; others are just inspired to give back to their community. No matter what, they’re people with the drive to build something from the ground up.

To turn your spark of inspiration into a successful business, get practical. Get in touch with your local SMB and access their free business resources, then build your business plan, incorporate, and standardize your workflows. Then focus on creating a signature experience that keeps your customers coming back. Finally, stay flexible and observant, and you and your business will be in it for the long haul.

Thanks so much for listening. We hope you’ve found these summaries useful and inspiring. Please let us know what you thought by giving us a rating!

About the author

Jackie Reses is the Chief Executive Officer of Luna Financial Group, a fintech building banking-related financial infrastructure for tech and crypto companies and the Chair of the Economic Advisory Council of the Federal Reserve Bank of San Francisco. Previously, she was the Executive Chairman of Square Financial Services, Capital Lead and Head of the People Team at Square Inc. (Block Inc). She has been named one of Forbes “Self Made Women,” Fast Company’s “Most Creative People in Business,” and American Banker‘s “Most Powerful Woman in Finance.” Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide, one of the largest private equity firms in the world. Jackie is also on the board of directors of Endeavor, Affirm and Nubank.

Lauren Weinberg is the Chief Marketing Officer of Square, where she leads global Marketing and Communications for the $100B company that provides business solutions for millions of small business owners all over the world. She has been named on Forbes “CMO Next,” Brand Innovators “Top Women in Marketing,” and Fintech Hub’s “30 Most Influential Fintech Marketers.” Prior, she held leadership roles at Yahoo, MTV, and AOL. She is an AdWeek Executive Mentor and advises early stage startups.


Entrepreneurship, Management, Leadership, Business Development, Business Franchises, Commerce, Customer Relations

Table of Contents

Acknowledgments vii
Prologue: A Letter to Our Readers xi
1 Taking the First Step 1
2 Creating a Business Plan 15
3 Legal Matters 31
4 Operations and Logistics How to Get Up and Running 45
5 Finances How to Manage Your Money, Get Loans, and Get Paid 63
6 Brand Building and Marketing 95
7 Hiring and HR 119
8 Roadblocks 157
9 Growth and Scale 171
10 Transitions 193
Index 209


Part starter-kit, part encyclopedia, and part inspiration, Self-Made Boss is an essential survival guide for small businesses

When it comes to getting practical advice, small business owners too often don’t know where to look. Sure, you can find all sorts of high-level strategic tips from Fortune 500 CEOs. But what if you own a restaurant, and you’re trying to figure out how to source good fish, or if you’re looking to increase revenue from your plumbing supply store? You’ll be running a lot of Google searches before you hear from someone who’s actually stood in your shoes.

Longtime Square executives Jackie Reses and Lauren Weinberg want to change this. So they reached out across the country, talking to dozens of entrepreneurs with valuable businesses―and invaluable advice. This book is the product of that research. Part starter-kit, part encyclopedia, part inspiration, Self-Made Boss is filled with information not just about who these small business owners are, but how they built their companies, step by step.

How did they get their start? When did they decide to hire more staff? How did they set a course for growth? And when problems arose, how did they fight through them? You’ll hear from a second-generation ice cream shop owner on how to manage price increases; an oyster farmer finding new ways to stay afloat in the middle of a global pandemic; a roofer who refused to be denied or defined by her race and gender―and dozens of other small business owners making a big difference in their communities.

No matter the size of your business today―or where you’re thinking about taking the jump tomorrow―you’ll find answers you can apply right away.

Because there’s a common purpose that all small business owners share: the drive to build something from the ground up; the relentless pursuit of turning obstacles into opportunities and roadblocks into stepping stones. It’s tough and messy, hard-fought and hard-won. And above all, it’s something you can’t have when you work anywhere else―or for anyone else.

That’s what it means to be a Self-Made Boss.

Video and Podcast


From the Back Cover

“A small business doesn’t come with an owner’s manual . . . until now. Drawing on their extensive experience working with small business owners, Jackie Reses and Lauren Weinberg share the stories and tips you need to help your business thrive.” – Adam Grant, #1 New York Times bestselling author of Think Again and host of the TED podcast WorkLife

“We started Shake Shack as a humble hot dog cart to raise money for a public park in NYC and never dreamed it would become a global public company. I’ve lived so many of the challenges that small business owners experience and this read provides the nuts and bolts guide every entrepreneur can get their arms around.” – Randy Garruti, CEO, Shake Shack

“Jackie and Lauren have worked with thousands of small business owners across multiple companies. They have distilled so many crucial lessons, resources, and tools here that the book is literally a how-to guide to helping your company succeed. And the learnings are well delivered—accessible, engaging, and practical.” – Allan Thygesen, Google President Americas and Global Partners

“Small business is part of our ethos at M&T Bank. Helping entrepreneurs grow their businesses—and themselves—through mentorship and resources is some of our most important work. We all need a community of advisors to instruct and inspire us, and that’s what Jackie and Lauren have created in this book for business owners everywhere.” – Rene F. Jones, chairman and CEO, M&T Bank

“When small businesses thrive, so does the entire economy. Self-Made Boss is teeming with actionable insights to help small businesses succeed, no matter the obstacles ahead.” – Karen G. Mills, Harvard Business School Senior Fellow, former SBA administrator and Obama cabinet member

“As always, Jackie and Lauren have provided us with sound advice. Use this book as your go-to manual with practical and real information. I loved reading these stories about the amazing small business owners who started with nothing and were able to make it happen.” – Gregg Renfrew, CEO Beautycounter

“Learning from mentors and a community of other business builders is key to my success as a serial entrepreneur. Jackie and Lauren have been mentors to thousands of small businesses, and their work helped millions more. Self-Made Boss is an impressive distillation of wisdom from years in the trenches, and I love how they tie highly relevant stories to insightful lessons.” – Joe Lonsdale, cofounder of Palantir, Addepar, Resilience Bio and Partner, 8VC

“Many of us dream of starting our own business. But how do we make those dreams a reality? Entrepreneur and small business gurus Reses and Weinberg share the real deal on what really matters when starting—and growing—a sustainable business. Their lessons from thousands of small business owners won’t just save you time and money, they will help you love what you do that much more.” – Lisa Kay Solomon, coauthor of the bestselling books Moments of Impact and Design a Better Business

“Jackie ties together her formative experiences, applies her Wharton-honed insights, and extends the leadership I have seen firsthand in her service as an alumna to others through this book. Readers will benefit from the book’s wit, wisdom, and empathy, and the depths of her interest in businesses of all types in varying sectors. She embodies the entrepreneurial spirit we strive to inspire at Wharton.” – Erika H. James, dean and Reliance Professor of Management and Private Enterprise, The Wharton School

“There are great entrepreneurs and there are thoughtful students of business. Jackie Reses is both, and it makes this book an important one. The US economy is much more likely to succeed if entrepreneurs succeed. And entrepreneurs are much more likely to succeed if they heed this important book’s wisdom.” – Laurence H. Summers, a Charles W. Eliot University Professor and President Emeritus at Harvard University, the 71st secretary of the Treasury under President Clinton, and director of the National Economic Council under President Obama

“Thank you, Jackie and Lauren, for creating such a thoughtful book as a lifeline to the real world of small business entrepreneurship! When I started my business 20 years ago, I wish I would have had something as valuable as this for guidance and support as I navigated what it is to be a boss in the world of big business. As a female entrepreneur running three floral businesses, navigating the ins and outs of business from scratch is full of challenges, both emotional and financial. You literally create the road map as you go.” – Sharla Flock, Sharla Flock Designs

Read an Excerpt/PDF Preview


Jackie: Forever thankful to my beloved family: Matt, Emilia, Charlotte, and Owen. They make me laugh and think every day. I love you and I’d be lost without you. My parents also showed me how the care of a local business person made a difference in a community. I spent my childhood working at Reses Pharmacy in Pomona, New Jersey, and some of my earliest memories are behind the counter helping to manage the greeting card inventory in a small shop. Life lessons from the pharmacy sit with me every day. I am also thankful to my coauthor and friend, Lauren. This has been a labor of love, and I couldn’t think of another person that I would want working on this with me.

Lauren: Thank you to my incredibly supportive family. Jeremy, Ethan, and Ben, you put up with my crazy schedule and have always been my biggest fans. I would never be able to write this book or lean in to my career without your unwavering support. My parents both worked in and owned small businesses. (Fun fact: my dad is featured in this book.) I appreciate the work ethic they instilled in me from a young age. I’d also like to thank Jackie, my partner on this initiative. Jackie has been my mentor and my biggest cheerleader for many years. I am so grateful for Jackie and my other mentors, including Lisa Licht, Kathy Savitt, Mollie Spillman and Nada Stirratt. I’ve been standing on the shoulders of these incredible women and make an effort to pay it forward every day.

We were lucky to have a lot of help with this book at every stage.

When we were first thinking about the idea, there were many at Square, where both of us worked, who dedicated their personal time to review and support ideas for the book. They include Ed Lin, Eitan Bencuya, Katie Dally, Mallory Russell, Justin Lomax, Zack Ashley and Kelsy Reitz. They were willing to lean in when this was just an idea and a book proposal.

Then, when we moved into finding sellers from across the globe, we enlisted the help of Nelson Murray, Jeff Suppes, Mallory Russell, and Evan Groll. They had an eye for small businesses that had incredible stories to tell and helped us brainstorm titles for the book as well. Mallory, in particular, helped us fine-tune the chapters and areas we would focus on to ensure we hit the most important topics for business owners.

We also needed advice on broadening our network. Samantha Ku, Andy Montgomery, and Audrey Kim went out of their way to support our research with additional insight and ideas. Audrey helped us think about which experts would be helpful to include so that we could get the frameworks organized. Andy gave us feedback on our design and had a critical eye toward the cover.

Andrew Gerlach from Sullivan and Cromwell, Gary Horowitz of Simpson Thatcher, and Ryan LaForce of Goodwin Procter also provided us first-rate legal insight. Alana White from Giant Spoon provided additional insight about how business owners should think about leveraging traditional media channels for marketing.

Michelle Garcia-Vasquez has been with us the entire time, organizing calls, keeping our drafts in order, managing the process with sellers and experts. She put her heart and soul into our book and took on a huge amount of work to help get this over the finish line! Kate Kapoor took on the final management of our drafts, bios, and photos and dug in with her fantastic organizational skills.

Ingrid Case is our voice. She understood how to jump in and help us bring the stories of our sellers to life. She worked with us throughout the entire process and made us laugh and cry. She interviewed every small business included in this book and brought the stories to life. Tyler Lechtenberg helped us on projects while we were at Square and once again helped in crafting these stories. He and his colleagues at Fenway Strategies, such as Sam Koppelman, live in rarified writing air . . . and we are thankful for their advice, edits, and voice.

Jack Dorsey didn’t write one word of this book. He did inspire us with his steadfast focus on how important the small business economy is, and how we need to create tools to help them thrive. His passion is inspiring and will always be a part of the story of how this book came to be.

Most of all, we want to thank all of the entrepreneurs, business owners, and experts who shared their stories and advice so freely. We’re proud to know you.


A Letter to Our Readers

Jackie: For four years, I traveled across the United States, a country with more food trucks and beauty salons, coffee bars, and record shops than anyone could possibly visit in one life span—let alone four years. That didn’t stop me from trying, though.

At the time, getting to know our country’s small businesses was a big part of my job. I ran the small business lending and banking business at Square. I believed deeply not just in crunching numbers and optimizing machine learning credit algorithms, but in actually talking to small business owners to truly understand their goals and challenges, sample their goods, and listen to their stories. I was part business advisor, part solutions creator, part psychiatrist.

And for four years, all across the country, I spent a lot of my time applying those skills. From Philadelphia to Minnetonka, Atlanta to Santa Rosa, I crisscrossed the country to meet these extraordinary entrepreneurs and hear their stories.

I met Kelly Kondah, who’d owned Colossal Cupcakes in Ohio, and talked about her approach to decor in her retail stores. I spent time with Courtney Foster, a one-chair beauty salon owner in New York City. I bought flowers from Jen Pratt, whose flower truck in Idaho brightens an entire community’s birthdays and Mother’s Days. I ate turkey legs with Philip Webber at his food truck in North Carolina. I even sampled the beats of Andrew Hypes, a DJ in Virginia.

Nearly everyone I spoke with—whether they’d invented a new snack for kids or operated a brick-and-mortar restaurant that had been passed down from their parents, whether they were running a bubble tea chain or a plastic surgery business—had something insightful to share about what it took to build, run, and grow a company.

Maybe it was a 60-year-old boosting sales by becoming a social media savant. Maybe it was an oyster farmer reinventing his business in the middle of a global pandemic. Maybe it was an entrepreneur who refused to be defined, or denied, because of her race and gender.

No matter the details, I was amazed by the wisdom and insights that each business owner could offer. They knew their stuff. The more I heard from them, the more I wanted other small business owners to hear from them, too.

Each of these conversations uncovered something else for me: When it comes to getting practical business advice, small business owners are woefully underserved. Sure, you can find all sorts of slick tips from towering CEOs of Fortune 500 companies. But what if you own a restaurant, and you’re trying to figure out how to source good fish, or if you own a plumbing supply store and you’re trying to crack $1 million in revenue for the first time? You’ll be running a lot of Google searches before you hear from someone who’s actually stood in your shoes.

I wanted to change that. I became focused on helping these small business owners share their advice—because the story of our country’s small businesses is anything but small.

Here in the United States, we have close to 30 million small businesses, and internationally there is comparable depth. I’ve always known how important they are to our country and the communities that make us who we are, because my parents owned one.

I learned from a young age that when you run the neighborhood pharmacy, as my parents did, there is no such thing as Christmas holiday. When customers were out of important medication on a holiday, they knew to call my family. If they needed a house visit, my parents would come right over. My mom embodied the idea that “the customer is always right” as she stood behind the counter of the pharmacy dealing with people who sometimes wore their stress in their language. It was a priceless learning experience to see business and community wrapped up with the entrepreneurial spirit of a family business.

There are business owners like my parents all across the country, whose employees make up more than half our working economy. But here’s the thing: those numbers still don’t come close to tallying up what these businesses mean, not just for the people running them, but also for the people who love them. Think about the neighborhood pizza joint your kid’s Little League team heads to after a big win or the family-owned hardware store that sold you the part that finally stopped that leaky faucet. Profits alone don’t convey the full story of these businesses. They don’t just contribute to our economies. They’re part of the fabric that holds our neighborhoods and towns together.

I hope this book reflects that larger story. In these pages, you’ll read not just about who these small business owners are, but how they built their companies, step by step. How did they get their start? When did they decide to hire more staff? How did they set a course for growth? And when problems arose, how did they fight through them?

From the example of the dozens of business owners we spoke with for this book, I hope you will take away practical advice and lessons you can put to work right away as you become your own Self-Made Boss.

When I decided to write this book, I spent a lot of time thinking about whose stories I would include in it—but I didn’t spend any time contemplating who I needed by my side to write it. From the very beginning, I knew I needed someone who’d lived a lot of these experiences on her own, someone who has seen the ups and downs of owning a small business from many angles. So for me, there was only one person I wanted to be my partner: my brilliant colleague and friend, Lauren Weinberg.

Lauren: Before I became chief marketing officer at Square, I’d been in the corporate world for nearly half my life. I’d led large teams for a major reality television network. I’d served on corporate boards—sometimes with other women, mostly without. I’d had workplaces I loved and jobs where I couldn’t wait to clock out. But one experience taught me more than any other: being my own boss.

In the middle of my career, I set out on my own as a consultant, helping both startups and established brands navigate marketing strategy. When I first started my own shop, I thought making the website would be the biggest hurdle. After all, I’d been doing marketing work for decades. I figured I had all the skills I needed—and a Rolodex full of contacts. What else was there to learn?

The answer, as it turned out, was a lot. You know the stuff that just happens when you work at someone else’s company? When you’re running your own company, you have to do all that stuff by yourself. All of it. Applying for an employer identification number. Setting up an LLC. Opening a business bank account. Sending out invoices—and making sure you actually get paid.

For me, that meant that instead of doing what I started my business to do, I was spending an inordinate amount of time plugging numbers into spreadsheets or driving to the bank. The first couple of months were especially rough. Working on my first two or three projects, I made the mistake of telling clients to pay me after I finished their project. These projects could go on for months, and during that time, I didn’t get paid.

I found out quickly just how steep the learning curve was going to be. During my time at Square, I saw that this constant learning and balancing act was all too familiar to so many of our sellers.

Since 2017, like Jackie, I’ve been listening to small businesses of every shape and size, helping them tell their stories and grow their companies. During conversations, in research data and survey responses, at educational events for sellers, and in the lead-up to big marketing launches, I kept hearing the same thing: One of the biggest struggles for any small business is feeling like you’re stretched too thin. If you run a food truck, you’re not only the chef, you’re also the accountant. In a bookstore, you’re not just in charge of choosing the latest titles and booking local authors for readings, you’re also responsible for building a social media presence. It’s part of what makes being a small business owner such a shot of adrenaline. But it doesn’t make things any easier.

When the Covid-19 pandemic hit in 2020, a big part of my job became reaching out to these entrepreneurs, hearing about how they were weathering a storm for which no one had time to prepare. When cities were locked down and in-person sales plummeted, small business owners were forced to adapt or close their doors, maybe forever. The stories I heard of business owners who shifted their focus, who retooled their business plans, who scraped and clawed just to stay afloat—those stories once again proved to me the brilliance and resilience that defines this community of small business owners.

Not every year will bring a pandemic, of course. But every year—every day—will bring its own new challenges. That’s why Jackie and I wrote this book. We hope it can help you avoid common pitfalls, or at least help you navigate through some of these roadblocks. We hope that you can spend less time worrying about the things you’re not an expert in—like running HR or setting up a profit-and-loss statement—and more time doing what you love. And we hope, more than anything, that you won’t feel alone, because you’ll know that even if you run your business by yourself, you are part of a community of small business owners who keep our economy, and our country, running.

Now, we know how busy you are, so we designed this book to be easy to read. Before you get started, here are a few tips about how you can use it:

  • You don’t have to read it cover to cover. Think about it as a reference guide, something you can flip to when you come across a new challenge. If you want to read about managing your finances, go to Chapter 5. If you want to learn more about marketing, head to Chapter 6. We hope to provide you with some answers—or at least, a good starting place.
  • We’ve got something for you, no matter the stage of your business. If you’re just starting out, you might want to check out our introductory chapters on starting a business (Chapter 1), creating a business plan (Chapter 2), and operations and logistics (Chapter 4). If you’ve been doing this a while and are feeling stuck, you might find inspiration in our chapters on roadblocks (Chapter 8) or growth and scale (Chapter 9).
  • This is a starter kit. We try to identify and cover just about any problem you might come across and give you the hard-earned wisdom of other small business owners like you. We recognize that sometimes, you might need to go further to get really in the weeds on a given topic—like your tax strategy or structuring an acquisition. That’s when you’ll want to find another resource or even hire experts who can help you with your specific questions. Throughout the book, we’ve made sure to provide advice on where to turn if you need further answers.
  • It’s a chance to spur reflection—and generate plans. At the end of each chapter, we’ve included questions that you may want to consider. It’s worth thinking ahead and gaming out possible scenarios. Even if a decision doesn’t feel especially pressing right now, it almost certainly will someday.

As you’ll read in these pages, there’s no specific road map for any small business owner. That’s the beauty—and the risk—of being your own boss. But no matter how you decided to start your business, or where you’re thinking about taking it, there’s a common purpose that all small business owners share. In fact, it’s more than a purpose. It’s an identity, one defined not by what you do but by who you are.

It’s the drive to build something from the ground up. It’s the relentless pursuit of turning obstacles into opportunities, roadblocks into stepping-stones. It’s the commitment to throwing everything you’ve got into your business, being willing to spend hours ordering inventory and balancing your sheets, putting every spare dollar back into your dream. It’s tough and messy, hard-fought and hard-won. And above all, it’s something you can’t have when you work anywhere else—or for anyone else.

That’s what it means to be a Self-Made Boss.

Welcome to the club.

CHAPTER 1 Taking the First Step

Two months into her job at a biotech startup, Meenal Lele read an article in a medical journal that changed the course of her life. For the first time, researchers had found that exposing children to small amounts of common allergens early in their lives could prevent them from developing allergies. For Meenal, reading this was a mixed blessing.

On the one hand, this news made her “kind of furious,” because her 11-month-old child had already developed severe allergies to eggs, peanuts, and tree nuts—in other words, it was too late to help him avoid allergies. But on the other hand, she finally had steps she could take that might help her other children remain allergy-free. So she started preparing microscopic amounts of foods like eggs and peanuts for him to try.

As it turned out, doing this in a way that was safe for many babies to eat—while making sure she didn’t contaminate her kitchen and endanger her older child—was easier said than done, even for someone who had spent her career pioneering innovations in biotech. She remembers asking herself endless questions: “How finely ground is fine enough? How many grams of protein are in a peanut?”

Meenal Lele Meenal Lele is founder and CEO of Lil Mixins, an allergy prevention company. She previously led the clinical studies and education that brought the Subchondroplasty procedure (acquired by Zimmer) and PIVO blood collection (acquired by BD) to market. She has an engineering and a business degree from the University of Pennsylvania.

There had to be a better way, Meenal concluded, but she couldn’t find it anywhere. So she decided to create her own solution. After two and a half years of experimentation, she pulled it off, creating Lil Mixins, a company that sells supplements with precisely measured amounts of common allergens to help children build a tolerance to them before it’s too late.

It’s a smart business that improves people’s lives—and it all came from Meenal’s life experience.

Based in Philadelphia, Pennsylvania, Lil Mixins is just one of those 30 million American small businesses we told you about in our Prologue. Each one has its own origin story.

Many entrepreneurs start their companies for the same reason Meenal did: they see a problem in the world and decide to become part of the solution. Of course, there are other reasons to start a small business too, whether you have an itch to strike out on your own, build on a family legacy, turn a passion into a profession, or give back to your community. Throughout this book, you’ll hear from entrepreneurs who took the leap of faith to start a company for all these reasons. In every instance, they had an idea they were excited about and a plan to bring it to life.

In this chapter, we’re focusing on that initial spark, the idea that spurs you to start your business in the first place. Because along the way, running your business will only get harder—trust us. If you can remember why you began the work in the first place, it will help keep the tough days in perspective.

Being Your Own Boss

Bobby Crocker Bobby Crocker owns LVLUP Fitness, a personalized training service in California’s Bay Area. He is an ex-professional baseball player.

Drafted out of college, Bobby Crocker played Major League Baseball as an outfielder for the Oakland Athletics. When a shoulder injury ended his baseball career, he knew he needed another way to make a living.

“I did interviews with other companies, but I kept landing back on wanting my independence,” Bobby says. “I remember watching my dad run a construction business. Like him, I feel a big motivation to be able to provide for myself and my family on my own terms. It gave me a sense of pride and purpose.”

Six years ago, Bobby began working as a self-employed personal trainer in the Bay Area, helping his clients build their fitness and their confidence. He loves the independence, he says, though he found aspects of it challenging at first.

“In baseball, the framework was provided for me,” Bobby says. “I knew what I would do every day, and I felt responsible for executing that schedule. Creating a framework for myself took some time.” In this way, for Bobby, being able to create his schedule, strategy, and relationships had positives and negatives: what he gained in freedom he lost in structure.

Carrying on the Family Business

Aylon Pesso Together with his father, Aylon Pesso owns and runs Pesso’s Ices & Ice Cream in Bayside, New York. His favorite ice cream flavor is roasted marshmallow.

Bobby is a solo act, but plenty of entrepreneurs become involved in small businesses alongside their family members. Aylon Pesso, for instance, co-owns an ice cream shop, Pesso’s Ices & Ice Cream, in Queens, New York, with his father.

The family has been in the dessert business since Aylon’s early adolescence when his father, Gidon Pesso, a serial entrepreneur then working as a house painter, decided to try his hand at ice cream.

Aylon scooped ice cream through high school and took over the store’s social media, website, and marketing in college. After graduating, he went back to work with his father, eventually becoming part owner and vice president of operations.

Aylon has an older brother, but he wasn’t interested in the family business. “I was closer to our dad, maybe more like-thinking,” he says. “That’s helped us make it work. We can look at something, give each other a look, and know what we have to do to make it work.”

For a long time, Aylon recalls, they offered 132 flavors every day, all made on-site in small batches. Now they use data from their point-of-sale system to understand which of their 60 flavors are making money.

“The ice-cream trade is a good business,” he says. “Ice cream gives people joy, and they get to give that experience to other people. I make something with my hands that will make someone happy.”

And even though working with family can bring challenges—as we’ll discuss in later chapters—when you are able to put smiles on the faces of customers alongside your loved ones, it can be that much sweeter.

Pursuing a Personal Passion

The enthusiasm Aylon Pesso feels for ice cream, Peter Stein feels for oysters. “I can’t remember a day that I didn’t love oysters,” he says. “On a calorie basis, oysters are the most sustainable and nutritious food source in the world. They’re high in all the good things and low in all the bad things.”

Peter had been a business management consultant, a New York classroom teacher, and an education software employee. Then he was laid off, and he did some soul-searching.

Peter Stein Peter Stein owns Peeko Oysters, which is on Long Island near New Suffolk, NY. He can’t remember a time when he didn’t love oysters.

“I grew up coming to the East End of Long Island on the weekends and in the summer,” he said. “I loved fishing with my dad, and my dad loved oysters as well. When I had a blank spot in my career, I went back to what I had always loved.”

That’s when he set out to build Peeko Oysters in Little Peconic Bay on Long Island. As you’ll read in Chapters 4 and 8, he’s become quite a success. Today, restaurants all over the New York area sell his Peeko oysters to their customers, and the retail side of the business is thriving too. Peter’s lifelong passion is still going strong.

Making a Living After a Life Transition

Like Peter, many business owners start companies in response to a personal transition: being laid off, returning to work after spending years as a full-time parent, or pivoting to a new industry after retirement.

Jen Pratt, for instance, started Fresh Sunshine Flowers in Sandpoint, Idaho, after her employer, clothing company Coldwater Creek, closed its doors in 2014. “My mom was a florist, and I grew up helping and learning from her,” Jen says. But building a brick-and-mortar floral business from the ground up was a daunting prospect. It meant high overhead costs, like rent or a mortgage, not to mention utilities. So Jen started her florist operation in a white box truck with a side window.

Jen Pratt Jen Pratt owns Fresh Sunshine Flowers in Sandpoint, ID. She began her business by selling out of a box truck with a side window, back when food trucks were at their peak.

Jen bought her truck in May. A graphic designer friend helped Jen come up with a logo, and another friend helped design decals to put on the truck. A third buddy helped her gut and build out the truck, and a fourth friend, this one a mechanic, got the truck in running order. By July 4, Jen was ready to roll out her floral spin on a food truck, offering up bouquets that were red, white, blue, and every color in between.

Giving Back to Your Community

Erin Caudell and her partner, Franklin Pleasant, believe that everyone should have access to safe, nutritious food. Through The Local Grocer, based in Flint, Michigan, they are putting that belief into practice.

Before they could do that, though, Erin and Franklin needed to get a farm—so they took out a loan and bought 10 acres from a county land bank that holds foreclosed properties. They started growing dozens of different kinds of organic vegetables.

Erin Caudell Erin Caudell and her partner, Franklin Pleasant, co-own The Local Grocer in Flint, MI. They are longtime food activists and newer farmers, working to make sure every community has access to nutrient-dense foods.

The Local Grocer has also teamed up with two other local farms as part of a community-supported agriculture (CSA) program, which allows families in the region to sign up for regular deliveries of a wide range of crops, from sweet corn and winter squash to broccoli and cauliflower.

They also participate in farmers markets, run a catering business, rent out their commercial kitchen, and sell their own and other farmers’ products directly to buyers. “We’ve probably worked with 25 different farmers to buy for the store,” Erin says. “We see this as a business incubator where we can give feedback and learn something ourselves.

“Franklin and I take part-time jobs here and there, especially in the winter, to make this work,” she says. The hope is that The Local Grocer will eventually support the couple and their two children.

Filling a Gap: Build the Business You Want to Patronize

When photographer Lucia Rollow graduated from New York’s School of Visual Arts, she couldn’t afford access to a darkroom. One day, when she was complaining about this to a neighbor, she learned that her building was renting storage spaces in the basement for $75 a month.

Lucia rented one and set up a darkroom in that space. When she started telling friends about it, she quickly came to realize that she wasn’t the only one in Brooklyn who needed a place to develop film. It wasn’t long before her little idea had a big following of paying customers.

A year later, Lucia had earned enough to move her business, which she called the Brooklyn Community Darkroom, into a storefront. In 2015, the darkroom moved to its current location in the Bushwick neighborhood. Now called the Bushwick Community Darkroom, it rents out darkroom time and offers development services and classes in developing and printing to an audience that ranges from beginners to professional photographers. “The goal is to support a community of photographers,” Lucia says. “Someone with any level of knowledge or experience can come and learn.” About 500 photographers use the facility every month.

Lucia runs the darkroom with a staff of 10 part-time employees, each working between one and three days a week. She relishes being in charge. “Now that I’ve had this flexibility,” she says, “I don’t think I could handle the lack of flexibility of working for someone else.”

Lucia Rollow Lucia Rollow owns Bushwick Community Darkroom in Brooklyn, NY. A graduate of New York’s School of Visual Arts, Rollow’s first darkroom was a storage cubby in the basement of her apartment building.

Same Picture, Different Details

No matter what kind of business they’re in, or why they started it, all small business owners have a common struggle. They’re all working to figure out how to best take an idea and turn it into a reality—and make a living while they’re at it.

Small businesses might look very different from the outside, but in reality, most are quite similar. Aylon Pesso sells ice cream and Jen Pratt sells flowers, but they both need to set up their finances and legally incorporate. They both hire help, run business operations, build their brands, decide how to grow and scale, and have to get past roadblocks. And they both may eventually transition away from the business they’ve built and step into whatever comes next.

If you’re starting or running a small business, you’ll have to do those things, too. You probably don’t sell oysters or make dietary supplements out of common allergens. But at root, your challenges and concerns will probably look a lot like the ones that Peter and Meenal face.

That’s why we wrote this book. We learned a lot hearing about how each of these business owners built their business. And we believe that you will, too.

Find and Use Free Resources

Before we dive into more of these Self-Made Bosses’ stories, we’d be remiss if we didn’t point out the free public resources that can help you start and grow your small business. The Small Business Administration (SBA), for instance, is a federal agency that gives out a treasure trove of free resources.


Bill Briggs Bill Briggs is former acting associate administrator, Office of Capital Access, a division of the Small Business Administration. Currently he works as a consultant in Arlington, VA. Running the 2020 Paycheck Protection Program is his proudest professional achievement.

“The SBA is the best-kept secret in the federal government,” says Bill Briggs, who worked for the SBA for three and a half years. “Going there is like going to a library for a small business that has very helpful librarians. They’ve seen your problems before and can help you do the right things and avoid the pitfalls.”

The SBA and its resource centers can help you:

  • Explore a new idea
  • Write a business plan
  • Find a mentor or coach
  • Grow your business
  • Get a loan
  • Find grants
  • Put your personal and business finances in order
  • Start or improve any part of your business
  • Draw up initial contracts

“The biggest mistake entrepreneurs make is not using the SBA network,” Bill says. “Google ‘SBA resources’ in your state. They will help you even if you just have an idea. Have hope and have patience—people out there want to help you.”

You can also take advantage of locally based help. Local chambers of commerce may offer valuable resources, including education and access to partners that can help you get started. There are also specialized chambers of commerce that support specific demographic groups, like the Black Chamber of Commerce or the Hispanic Chamber of Commerce.

Many other free resources can also help guide your business formation. To start and run the Bushwick Community Darkroom, for instance, Lucia Rollow used Start Small Think Big (, a nonprofit that helps under-resourced entrepreneurs create businesses in underserved areas. “If I had used them back in the beginning, starting this business would have been a lot easier,” she says.

In fact, Lucia says, New York and many other locations around the United States have free public resources for entrepreneurs. “Start with your city’s website,” she suggests. “Look for a section on small business resources. Do a Google search. If you’re a woman or a member of a minority group, look for services to support you specifically.” You might be surprised at what you find in your local community.

More important, enjoy the jump! It’s daunting, emotionally challenging, and may very well become your life’s work. With those stakes in mind, take the time to think through how you will start, run, and grow your business.

It’s the first step to becoming a Self-Made Boss.

Questions to Consider

  • Will you like being your own boss? Do you prefer dictating your own schedule—or are you the kind of person who needs more structure?
  • What are your passions? Could you turn them into a career?
  • What kind of businesses do you wish existed? Could you be the person to make one of them happen?
  • Do you have a support network of friends and family who can advise you or provide other support?
  • Are you okay with uncertainty? Are you the kind of person that is willing to ride out the ups and downs? If so, when are you going to get started?

CHAPTER 2 Creating a Business Plan

Michael Lassner is a man with a plan—in fact, he’s a man with many plans. That’s because, when he started Allied Steel Buildings, he paid the price for not having one.

In the early days, Michael and his business partner ran their company out of an apartment in Fort Lauderdale, Florida. They were so busy doing the work in front of them that they didn’t make time to think about what came next.

Over the years, however, it became clear that the pair had different visions for their future. Michael’s partner wanted to stay smaller and closer to home, working on simpler projects. Michael wanted to make the business bigger, more global, and more complex.

“The first year was great. A year or two later, we began to wonder if we were right for each other,” Michael says. “Clarity around our business plan was the missing piece. We were looking at how we can be successful today rather than at where we were going. If we’d done that, we would have realized that this wasn’t the right partnership.”

After buying out his former partner, Michael focused on building alignment with his team so that everyone would be on the same page about their purpose. Today, he and his employees maintain an ongoing business plan.

“We think about our goals and the markets we’re in, and we plan around opportunities in particular markets,” he says. “We do postmortems, too. Here was the plan, what happened, what can we learn. We always learn something.”

Michael Lassner Michael Lassner, president of Allied Steel Buildings, is disrupting the global steel construction industry. He believes success is created by modeling business strategies around client needs. Michael leads an international team of innovators, who tirelessly work daily to deliver on the promise of clients first.

Now? Michael says he has “plans within plans—not just a long-term goal of entering a new market, but a plan for how to actually accomplish it,” and he thinks all small business owners should do the same—to analyze not only where they are, but where they want to go and how they’re going to get there.

In this chapter, we will show you how to do exactly that.

The Blueprint for Your Business

Small businesses have about a 50-50 chance of surviving the first five years—and one in five doesn’t even make it a full 12 months, according to the US Bureau of Labor Statistics.

Michael was lucky to be able to buy out his partner and run the company his own way. But businesses have a much better shot at long-term survival and success if they lay out their vision for the future before, not after, they start running it.

This means writing a business plan, and it’s one of the most important steps in building a successful company. Sometimes this business plan is written for public consumption. For instance, if you would like anyone else to put money into your company—which could be in the form of a grant, stock shares, or a loan—you will need a polished business plan. A bank will certainly want to see one before approving a loan. Your family and friends might have fewer requirements before sending you a check, but a written plan will still help set their minds at ease by demonstrating that you’re taking your venture seriously.

Even if you don’t intend to take loans or outside investors, and even if you don’t have anyone to read your business plan, systematically thinking through a blueprint is still critical. Yvonne Cariveau, director of the Center for Innovation & Entrepreneurship at Minnesota State University’s College of Business, is an expert on business plans. She says that you don’t necessarily need to write out a buttoned-up essay, but you do need to do the thinking and research that a business plan forces you to perform.

That’s what Jordan Rosner did when she opened her photography business in Millburn, New Jersey. She researched her industry, wrote up a plan, put it in a drawer, and hasn’t looked at it since. What she learned in the process of writing the plan, however, has stayed with her every day. She says thinking about how she was going to approach every element of her business is what’s helped make her business a success.

Yvonne Cariveau Yvonne Cariveau directs the Center for Innovation & Entrepreneurship at Minnesota State University in Mankato, MN. She teaches classes on entrepreneurship and has been an entrepreneur herself for 28 years with her business, Internet Connections, Inc.

Like Jordan, you might end up doing the research, writing a rough draft, and stopping there—using your business plan for internal purposes. Or you might draft an externally facing plan: perhaps one for bankers or venture capitalists, one for individual investors, one for potential business partners, and one for yourself. The information in these documents won’t change, but the focus will shift toward the things you think a particular audience will want to know.

A business plan has multiple sections, each of which is described briefly in this chapter.

An Executive Summary

A good executive summary pops. It should grab the reader and explain, succinctly and compellingly, why your business will succeed. You’ll want to explain briefly what’s in the rest of the document, particularly the problem, solution, and audience, so that readers will understand what you’re doing and why. Tell your story as vividly as you can. Another tip: Write the summary last. It should be a greatest hits, of sorts, for what’s to come. Just because it’s short doesn’t mean it’s not important; it might be the most critical part of the entire document.

Jordan Rosner Jordan Rosner is a photographer in Millburn, NJ. She got her start in photography in high school and worked for local newspapers after completing a degree in photojournalism from Lehigh University.

The Management Team

Your plan should include bios of the owners and key employees of the business, particularly if they have relevant experience for the new situation. Each person’s bio can be as short as a few bullet points or a few paragraphs that highlight what’s relevant. You don’t need to include every step of your career; be selective and decide how best to present yourself. Explain what qualifies each person for his or her role.

Your team members don’t need to have worked in your industry, but you do need to draw parallels between the work they’ve done and the skills you’ll need from your company’s management team. If you haven’t spent much time in your industry yet, an advisory board of people with relevant experience can help round out your team.

Problem, Solution, and Audience

Most businesses exist to solve a problem, such as selling a product that customers can’t get nearby or offering a new or better service than what’s already on the market. But before you decide that your solution is the solution, spend more time listening to other people talk about the problem.

Do your research, no matter what field you are in. “Define your problem very, very specifically. Observe. Ask open-ended questions,” Yvonne says. Cariveau likes to snowshoe, for example, but finds it awkward to attach her snowshoes’ back binding to her boots. If she were thinking of making a product to solve that problem, she says, she would go and watch people put on snowshoes. Where do they hit problems? Do the difficulties involve flexibility, cold fingers, stiff plastic, or bindings that are too short? The point is, refine your idea and then refine it some more. Even after you launch your product, listen to customer feedback and keep iterating.

“Entrepreneurs fall in love with their solutions before they really understand the problem,” she explains. Is the problem you’re considering actually worth solving? Is the solution worth tons of money and years of life? And is your solution the best one—or is it just the first one you thought of? Make sure you’re honest with yourself about your answers.

Then, if you still feel you’ve identified a problem that you think you can solve, consider who might pay you to solve it. Is your product a good match for their needs?

It’s also possible that no one will pay you to solve a problem you’ve identified. Hedberg Maps in Minneapolis, Minnesota, created an atlas of all the area sports facilities. The company thought that parents would want directions to the soccer fields and hockey rinks where young people were playing, and that school sports teams could sell the atlas as a fundraiser. However, parents were more comfortable getting directions from apps on their phones, and a local soccer association already had a lock on fundraiser sales. The map company ended up paying to have the unsold atlases destroyed.

If you’ve established that the problem in front of you is worth solving and potentially profitable, ask yourself: Who else has tried to solve it? Did that attempt work? What can you learn or borrow from other companies in the same industry? Don’t disparage the competition. Most people aren’t all that different from you—they, too, are trying their best to solve a problem. Instead of dismissing them, explain what’s different about your solution and why it will be more successful.

At the end of the day, a prospective business owner needs to know if her idea is desirable, feasible, and viable. Is this a problem that should be solved? Will customers pay you enough for the solution to make solving the problem worth your while?

When you’re answering these questions, don’t make claims without backing them up with evidence. Keep your projections conservative, and be realistic about the time and resources available to you. It’s good to be optimistic—that’s why you’re getting into business—but overly optimistic assumptions will set you up for failure. Whether you’re building a house or a business, most things cost more and take longer than you initially predict. Write up a business plan that assumes the worst-case scenario. That way, at the very least, you’ll meet your baseline. Anything above it is a bonus.


Now that you’ve identified a problem and your solution, you’ll have to go about actually producing your product or streamlining your service. You’ll need materials and a way to manufacture what you’re selling. What method will you use to make your product? What facilities and equipment will you use? Who will do the work, and what will their roles be? What processes will you put in place for production? Will you have an office? A store? Where will these things be located? Will you need to find or build new locations? When, where, and how will you do that?

Lisa O’Kelly Lisa O’Kelly is cofounder of Zellee Organic, based in Maui, HI. The company makes an organic, plant-based fruit jel snack that uses konjac, a plant from East Asia, to gel the product, instead of gelatin.

Operations have been an issue for Zellee, a Hawaii-based company that makes a plant-based fruit snack. The concept started as a home kitchen recipe, but formulating a recipe for commercial success involved hiring a food chemist and a nutritional label attorney. Next, the firm found someone who could package the result in squeeze pouches. But the owners quickly recognized the manufacturer wasn’t a good fit, so Zellee went through two more options before they solidified a good relationship with a manufacturing facility.

Their troubles with manufacturers may be over, but Zellee is still working out supplier issues. On its last run, the company had difficulty sourcing peach puree, says co-owner Lisa O’Kelly. “Ingredient supplies can be dependent on the quality of the last harvest,” she says.

In your business plan, you’ll want to think through your operations as specifically as possible. The goal is to lay a good foundation for production and sales—as well as alternatives so you’re prepared when you hit a bump in the road.

Lisa says you’ll most likely need to find more than one supplier, and you should talk to other businesses in the same space about your manufacturing options. If you’re producing at a large scale, for example, you’ll have many more variables to consider. “You may need to manufacture overseas, at least to start, because it’s so much less expensive,” she said. “US Department of Commerce Export Assistance Centers, which have feet on the ground all over, can help you figure out manufacturing and understand the questions and expenses involved.”

For more on operations, check out Chapter 4.


Once you know how you’ll source your materials and have developed the process you’ll use to transform them into a finished product, you need to identify each of your costs. You should understand exactly how much you will spend to make a unit of whatever you’re selling.

Without understanding how much it costs you to produce something, you can’t know how much you need to sell it for in order to make a profit—or at least stay in business. “If you have a business where it costs you $100 to make an item and you can only sell it for $90, then you might as well just create an organization that gives $10 to every person you meet,” Minnesota State’s Yvonne Cariveau says.

Say you make muffins, and it costs you more to create them than you can charge for them: you don’t have a business—you have a charity. Go look at the competition and see how much they’re charging for a muffin. This is called benchmarking data, and in most industries, you can find prices for any given good by being curious and shopping as a customer. “Data is knowledge,” Lisa says, “and it helps you make a structured guess. You can have the best muffins ever, and the numbers are still more important.”

How many muffins do you think you can sell? Start with the total size of your market and figure out how many people you can make aware of your business through marketing. Of those who know about you, maybe between 2 and 3 percent will visit your website. An even smaller proportion will make a purchase. From playing with these numbers, you can create cash flow and balance sheet projections.

As you go forward, simultaneously try to increase income and decrease costs. Could you charge a little bit more? At what price point will a customer stop buying? “Get a projection sheet and play with the projections,” Lisa says. “There are templates everywhere.”

Remember, too, that you don’t just need enough money to open. You need enough money to get through the inevitable ups and downs of the first few weeks and months. Most businesses aren’t immediately profitable, and all businesses go through booms and busts. Assume that you’ll earn less and spend more than you initially imagined.

While making your business plan, you should also think through how you’ll manage repayments to investors and lenders if necessary. Whether they take a hands-on role or operate as silent partners, every financial contributor wants to know when you will repay the investment or loan, and at what rate of return. It’s typical for investors to want out in three to five years.

This is just a taste of what you’ll want to consider when it comes to finances—to learn more, check out Chapter 5.


Now that you’ve thought through your operations and financial viability, how will you find prospective customers and tell them about your value proposition?

Chapter 6 explores marketing strategies in more detail, but it isn’t as simple as handing out some flyers. You’ll want to tap into your network; build an online brand, including on social media; consider partnerships with other small businesses; and explore advertisements and earned media opportunities. Marketing is a constantly moving target—you’ll always need to be looking for new ways to reach your audience.

And remember that you’re not only marketing your company. You’re marketing your individual products, and it’s important to do that strategically. “Market the things with the largest profit margins first,” Lisa says. That advice forces you to think about the cost to you of whatever you’re selling.

You also need to think about the kind of sales you’re making. It’s easier to sell more to existing customers than to find new ones. How will your business find first-time clients? And how will it persuade them to stick around and buy from you again?

Those are the primary sections of a written business plan—and the primary concepts to think deeply about, even if you’re not writing the plan out formally. From here, you can use or tailor the plan for any audience you need. You might have a presentation for an investor; it wouldn’t hurt to show a possible lender a well-thought-out business plan. It may be something you continue to refine among your leadership team. But even if you simply keep it in a folder on your computer and never look at it again, the work you’ve done will stay in your mind, and it will help form your strategy going forward.

Take It on the Road

Before you dive in headfirst, make sure to test your conclusions. “Make your product, take it somewhere small, and see if anyone wants it,” says Lisa. It could be at a fair or on a street corner. It could be a trial run with a few potential clients. Based on that experience, what about your projections do you need to change?

Here’s an important factor: pay attention to how much you enjoyed the experience. “Figure out if you even like to do this,” she adds. “Maybe you’ll hate it!”

If it’s the latter, think long and hard about whether this idea is the right place for you to dedicate a lot of time. Most businesses probably won’t be very successful if their founders aren’t excited to do the work.

A Few More Planning Tips

As you write your business plan:

  • Have a vision. Present your vision for what you believe you are building. A vision can be more future looking and optimistic about your goals. Be as clear-eyed as you can be in stating what you want to be.
  • Be logical. Think like a banker or an investor for the concrete details, not like a dreamer.
  • Support your claims with statistics, facts, and quotes from knowledgeable sources.
  • Don’t discuss rumors. Hearsay about your competitors doesn’t belong in a business plan.
  • Avoid superlatives. Major, unique, the first, the only, the best, the most, unbelievable, amazing, terrific—none of these words should have a place in your plan. In most instances, you can’t back up these claims with data, because they are, at their core, opinions. There’s no way, for instance, to prove that you have the best Mexican food in town. (You can, however, quote someone else saying that—a food reviewer, for instance—if it will add credibility.) There’s also a very good chance that your product or service is not truly the first or unique. That’s fine. The world has room for more than one vintner. Just be truthful in what you claim.
  • Be realistic. Don’t overestimate your financial projections or underestimate your time frames. Assume that your business will bring in half the revenue that seems reasonable and take twice the time you initially estimate to get up and running. If you’re able to bring in more money in less time, that’s great. Make the surprises good ones.
  • Hire or contract with an accountant or a financial expert to help you think through the financial side of your business. If you’re writing a business plan for investors or lenders, ask the accountant to put your financial projections in the standard business format that your audience expects.
  • Don’t send investors a gimmick. They’ll eat the cookies that you send, but the baked goods won’t make them more likely to invest in your business. Investors want facts, not snacks.

Ask for Help

Whether you create a formal business plan or not, thinking through a proposed business is a lot of work. You don’t have to hire someone with an MBA or pay consultants—not at first, anyway. You can get help, usually for free, from a wide variety of sources:

  • The Small Business Administration (SBA) is often the quickest way to find free help. It funds small business development centers (SBDC), often hosted by large universities, which can help you one-on-one for as long as you need.
  • Your local chamber of commerce likely has resources and relationships with advisors and business content.
  • County and city governments, as well as local, state, and federal lawmakers, often offer grants to help small businesses.
  • Retired people from your industry might be happy to coach you, or you could join a group of current entrepreneurs who meet regularly for advice and support. Chambers of commerce and SBDCs can help you find both.
  • Workforce Investment Boards exist in every state. They help unemployed people find jobs and offer subsidies to business owners to hire an employee for three to six months. They may also offer subsidized employee training.
  • Your own network. “Think about your friend group,” says Jen Pratt, owner of Fresh Sunshine Flowers in Sandpoint, Idaho. “Who can help you? You don’t have to do this on your own. You have an amazing support system already.”

Jen Pratt Jen Pratt owns Fresh Sunshine Flowers in Sandpoint, ID. She began her business by selling out of a box truck with a side window, back when food trucks were at their peak.

Questions to Consider

  • Have you sketched out your business plan, including vision, operations, and financial needs? Books, online resources, and Small Business Administration (SBA) resources can all help you organize and refine your thinking.
  • Can you succinctly articulate your business plan?
  • What problem are you solving or need are you filling? Will someone pay you for your solution?
  • What business tools or vendors do you need to get started? Do you know how much it will cost and what you’ll need to do to get them on board?
  • What milestones will you aim toward on your way to success?

CHAPTER 3 Legal Matters

Five years after starting Jewel Branding in Atlanta, Georgia, Julie Newman says she felt like a dairy farmer who needed to milk her cows every day: “I couldn’t go away for a few days and know that everything would be fine.”

Julie Newman Julie Newman is a licensing executive specializing in art influencers, designers, and design-based corporate and cultural brands. Areas of expertise include consumer products retail strategy, brand strategy, with strengths in brand management, international strategic partnerships, and creative brand extensions.

That’s why she decided to bring on a partner who could help make sales and run the business—and when she met Ilana Wilensky at an industry networking event, she knew she’d met her match. “I had a gut feeling that this would work well,” Julie says.

At first, Ilana worked as Julie’s employee. But, over time, the two developed their own areas of expertise: Ilana mastered sales, marketing, and public relations, while Julie focused on finance, operations, and processes. After a year, Ilana came aboard as an official partner. She bought a third of the business, with an option to buy another 15 percent after three years. Together, she and Julie also own a software business, which merchandizes the technology they’ve developed to run Jewel Branding to the rest of the branding industry.

Ilana Wilensky Ilana Wilensky is president of Jewel Branding and Licensing in Atlanta, GA. Her agency represents designers and brands to license their trademarks and designs to manufacturers across a wide range of consumer products that are sold through retail channels.

Though they say they get on so well that they haven’t had to refer to their contract, the pair couldn’t have become official partners without a written agreement.

While taking the time to write down how your business will operate might sound like busywork, that couldn’t be further from the truth. Not all partnerships are going to run as smoothly as Julie and Ilana’s. Sometimes roles will be less clear; sometimes you’ll have multiple people with varying degrees of ownership; and sometimes you’ll need to account for intellectual property, protect yourselves from liability, save money on taxes, or manage some other variable within your agreement.

In each of these cases, you’ll have to answer a question, usually right when you begin your business: How are you going to structure your company?

In this chapter, we’ll walk you through your options and discuss a few other legal matters you’ll want to think through. While we are outlining the basics, do your own web research and follow up with an attorney so that you have a more detailed view of the pros and cons of each structure and how it applies to your personal situation.


Jeremy Weinberg Jeremy Weinberg is a tax attorney currently residing in Short Hills, New Jersey. Jeremy specializes in the taxation of partnerships and similar pass-through entities. After spending 10+ years in private practice, Jeremy retired from the practice of law to start a travel company and is now his own self-made boss.


A partnership is a legal arrangement that lets two or more people own and operate a business together, sharing in that company’s profits and losses.

Building a strong partnership is an intentional act. Jeremy Weinberg, a partnership law expert in Short Hills, New Jersey, says potential partners should always take time to ask each other questions to make sure they’re on the same page. These include:

  • What is your vision for this business? How do you see it evolving? How do you imagine your current and future roles?
  • What will each of you put into this partnership? Contributions might include money, expertise, time, contacts, a rent-free spot in a garage—anything, really!
  • How will you allocate partnership income and loss among partners? If you’re putting equal amounts of money, time, and skills into the business, it might make sense to apportion income and loss 50/50. If your contribution levels aren’t the same, what’s the right way to split the pie?
  • How much of what you earn will go back into the business? How much will be distributed to each partner? On what schedule?
  • If one partner dies, will that person’s shares go to her heirs or to the company’s other shareholders? Or will those circumstances trigger a company sale, with proceeds divided between each partner or heir?
  • How will this partnership end? You might intend to sell the business, perhaps when it reaches a particular level of sales or profitability. You could plan to someday sell your interest in the partnership. If that happens, does the other partner get right of first refusal on the purchase? Can your partner veto your sale if she prefers not to work with the purchaser you’ve selected? Will one partner buy out the other at some point?

Although tax laws dictate certain requirements for partnerships, you have a lot of flexibility in determining the answer to most of these questions, Jeremy says. A partnership agreement can set out what you’ve already decided you’ll do at various junctures, or it can describe the process you’ll use to make those decisions when the time comes. A clear written agreement can significantly contribute to a partnership’s success, because it forces both people to think through hard questions they otherwise might put off until it’s too late.

Sometimes, simple problems sink partnerships. Mike Yardley, a mechanic and owner of MYT Automotive in Columbia Falls, Montana, was part of a partnership that he recalls falling apart because the pair didn’t discuss how much each of them would earn or how they would pay the rent. “The friendship didn’t survive being around each other all the time, becoming a business, and surviving the lean times,” Mike says.

Mike Yardley Mike joined the army out of high school and used the GI Bill to learn auto mechanics. Mike worked for auto dealerships until 2005. He made the decision to work for independent auto shops and found he was better off working for himself, which he has been since 2009.

In other situations, more complicated problems are to blame, as when Michael Lassner, CEO of Allied Steel Buildings in Fort Lauderdale, Florida, realized that he and his partner worked well together in the short term but had opposing long-term visions. In retrospect, he says, he didn’t pick the right person for the company he wanted to build. Recognizing that from the get-go would have saved a lot of time and stress.

Other partnerships have floundered simply because the kitchen is bursting with cooks. More partners can mean more money and expertise, but it can also mean more opinions and more jostling for control.

Julie and Ilana are proud of the partnership—and the companies—they’ve built. But it hasn’t happened on its own. Outside of the legal agreement they worked up together, their strong partnership also depends on daily practices. Here are a few of their tips:

Michael Lassner Michael Lassner, president of Allied Steel Buildings, is disrupting the global steel construction industry. He believes success is created by modeling business strategies around client needs. Michael leads an international team of innovators who tirelessly work daily to deliver on the promise of clients first.

  • Divide responsibilities. Respect that the other person is competent to handle the items on their plate.
  • Make big decisions together.
  • Communicate. “We talk every day,” Julie says. “We need to be on the same page for ourselves and for our employees. We try to have a united front and handle things together.”
  • Put ego aside. Support each other and your employees by making sure everyone gets recognition for their contributions.
  • Collaborate. “We’re collaborative, and we’ve found that it doesn’t work if we hire people who aren’t,” Ilana says.

After eight years, Ilana and Julie are friends as well as business partners. They socialize together outside work. Their husbands even like each other. “We’re very lucky that this is such a strong partnership,” Ilana says. “That doesn’t happen all the time.”

Corporate Structure

Whether you’re going into business on your own or with a partner, one of the first legal decisions you’ll make is figuring out the corporate structure you’ll use.

Your corporate structure lays out your company’s parameters, governing how you pay taxes, how you split ownership, and a few things you are and aren’t able to do. There are a variety of possible incorporation types, each with its own advantages and drawbacks. We’ll walk you through them here.

Sole Proprietorship

This is the simplest form of incorporation. You don’t need any particular paperwork to incorporate as a sole proprietor, though you may need local licensing and/or a DBA—a document stating that you’re “doing business”—to operate legally. In some states, business owners file DBAs with the state secretary of state. Others ask you to file a DBA at the city or county level. Google “where to file a DBA?” to find out what your state requires.

A sole proprietorship is what’s called a pass-through entity: company profits are taxed once, as part of the owner’s personal income. Owners don’t need to submit a separate tax return for their businesses; instead, they add a Schedule C to their personal tax return. The potential downsides to sole proprietorship are that you’re on the hook for any business liability or debt you incur—and just one person can own your company. But because they’re so easy to set up, it can make sense to start out as one. After all, you can always move to a different corporate structure later.

Limited Liability Company (LLC)

Nat Case Nat Case is a cartographer and designer in Minneapolis, MN, where he is also co-owner of INCase LLC. His work includes maps for National Geographic magazine and atlases, interpretive landscape signs, and maps for a variety of scholarly publishers.

An LLC is a little more complex than a sole proprietorship, but the hassle isn’t huge; you just have to file some paperwork and pay some fees.

Nat Case, a cartographer in Minneapolis, Minnesota, says that it took him around two hours to register his partnership as an LLC. He searched “how to register an LLC in Minnesota,” and the results helped him fill out a form at the Minnesota State Department and announce the company’s incorporation, which is a state requirement. The registration fee was less than $100, he says, and the public announcement cost around $50. INCase LLC, which offers cartographic and editorial services, has to renew the registration every year, but that’s free and easily accomplished online.

In exchange for that small effort, incorporating as an LLC offers you significant benefits. For starters, you can have as many owners as you like. And while it’s similar to a sole proprietorship in that it’s a pass-through entity, meaning that business profits are taxed just once, it also has the advantage of protecting the business owners from business liabilities.

“If you’re a sole proprietor, your personal liability is on the line if a customer or employee sues you,” says Sarah Barrack, a partner at a New York law firm that she managed. “You will pay any damages from your personal assets, which are all fair game.”

But if you set up a legal corporate entity, such as an LLC, only your business assets are at risk. You’re probably not going to lose your house or your retirement money, Andrew says.


Sarah Barrack Sarah Barrack is a lawyer in the New York City metropolitan area. She has been working with small businesses and creators for decades. Sarah specializes in working with creative talent in the entertainment industry.

S Corporation

Like an LLC, an S corporation lets you have multiple owners—in this case, up to 100 shareholders, all of whom must be US citizens or residents. It keeps your personal and business liability separate, and profits are taxed just once. As with an LLC, you’ll need to file paperwork and pay fees to stay in compliance. Structuring your business as an S corp also means that you’ll have a board of directors, and you’ll have to follow rules about holding meetings and keeping records. You’ll need an attorney to help you set up an S corp.

LLCs and S corporations are both taxed once, on owners’ personal tax returns, and they both protect owners’ personal assets from business liability. S corporations do have some advantages over LLCs. Some investors prefer to put money into S corps, and because they’ve been around much longer than LLCs, S corps are often more familiar to lawyers and other advisors.

S corps also offer business owners the ability to receive both salary and dividends, which can mean a lower overall tax bill. LLC owners, by contrast, pay self-employment taxes, which can mean higher overall taxes.

If you hope to eventually raise capital by selling shares or going public, you’ll want to incorporate as a C corporation. Changing from S corp to C corp status is easy and simple. The trip from LLC to C corp, on the other hand, is much more complex.

C Corporation

If you hope to one day sell your shares publicly, this is the best corporate structure for you. It allows unlimited shareholders and permits multiple types of stock shares. Otherwise, it’s just like an S corporation, but with one significant difference: profits are taxed twice—first at the business level and then again at the personal level.

A C corporation structure might give you more access to capital, but at the price of reduced control for the initial owners, plus many more reporting requirements.

Like an S corp, a C corp is not a do-it-yourself project. You’ll need an attorney with experience in this area.

“For small businesses owned by individuals, an S corp is a good choice, and an LLC is better,” Sarah says. “You want a pass-through entity, one that is taxed as though it’s just you, and taxed just once.”

Unless you have a specific reason to choose a C corp construction, don’t. An LLC and an S corp both protect you from personal liability without increasing your tax burden.

Making It Official

If you alone own your company, or you have a single partner, you may be able to do your own paperwork. You can also hire a service or a small business attorney. If you have multiple investors, Sarah recommends bringing a lawyer on board. Even in a two-person partnership, you should discuss what rights and responsibilities you’ll each have, and document your agreement, in addition to the rights that any investors may have.

As you designate ownership, keep in mind that a business that is majority-owned by women or Black, indigenous, or other people of color will have advantages in marketing, landing government contracts, and potential eligibility for government programs, grants, and tax incentives. In a two-person partnership where one person is male and the other female, or one person white and the other an underrepresented minority, it may make sense to structure ownership not in exactly equal halves, but with a tilt to qualifying for this unique status. “My wife is my LLC partner, and if I’d been smart, I would have registered the company as more hers than mine,” Nat Case says.

Licenses, Intellectual Property, Insurance, Privacy Protection, and Taxes

Filing paperwork to document your incorporation is just the beginning for many businesses. You may also need a license from your state or city. Research this, register, and pay fees as necessary. Yes, it’s a hassle, but it’s preferable to paying fines or even having your business shut down later if you ignore this step.

Look into other requirements, too. In general, if you want to start a business that involves safety precautions, such as food service, construction building systems repair, or haircutting, you are going to need to do more than simply register with your city to open up. Businesses that serve alcohol or involve firearms have both federal and state requirements. Google searches, professional organizations, and consultants can all help you navigate the thicket, too.

Pay attention to the legal side of any intellectual property you’re using. If you’re building a business using other people’s technology, make sure you have permission to do so. You don’t want to accidentally infringe on someone else’s rights and have to dismantle your company. You should also protect your own intellectual property by filing for patents and copyrights as appropriate. A trade or intellectual property lawyer can help you with both research and the filing process.

Pick a business name and create marketing materials that don’t copy anyone else, even accidentally. See what businesses are in the same space. Search online. When you incorporate, most states will let you search their database of company names. Do that so you don’t rip off anyone else’s name; that can come back to bite you, too.

No one wants to pay for insurance, but it’s still important to do so. You’ll want owner’s or renter’s insurance for your company’s physical location, as well as errors and omissions (E&O) insurance to cover your liabilities. An insurance broker can provide a package that covers typical small-business exposures.

If you take information from your customers—email addresses, credit card details, account passwords, other private financial or personal information—you need to be sure that you protect that information from hackers. That means segregating information and shielding it electronically and manually in ways that comply with state and federal regulations. Choose technology products that protect customer information.

Don’t overcomplicate things. Buy what you need now—and nothing more. Don’t buy an enterprise software system for a one-person operation.

Another tip: Pay your payroll taxes, sales tax remittance, and estimated quarterly taxes on time. The penalties for not doing so aren’t terrible, but they’re also a completely unnecessary expense. It’s very easy to get behind and never catch up if you don’t stay abreast of your tax responsibilities. Helping you with this is one of your accountant’s primary duties.


You might purchase a franchise, or you might ultimately decide to turn your new business into a franchise.

There are multiple types of franchises: product franchises, manufacturing franchises, or business format franchises.

To franchise your business or become a franchisee, you’ll want the help of an attorney with specific experience in this area.

Unless you’re opening up a law firm, odds are good that you aren’t starting your business to do legal work. When you’re busy, it’s the last thing you’re going to want to do, but it’s also the only way you can be sure that your company is aboveboard. So, think about the type of business you want to form, research what kind of incorporation makes most sense for you, and get it done. You don’t have time to waste. You have a business to start.

One last note: If you’re worried you’re in over your head figuring these things out, or you think you’re at risk of skirting the law, hire a lawyer. It may feel expensive, but the peace of mind will be worth it.

Questions to Consider

  • Do you want to start your business by yourself—or will you want a partner? If you do, what kind of partner do you want?
  • How will you structure your business? Have you compared legal structures that fit your needs?
  • Do you want many shareholders—or, eventually, to become public? Do you want to become a franchise?
  • Are you covering all your bases on licensing, incorporation and set-up?

CHAPTER 4 Operations and Logistics

How to Get Up and Running

In 2015, Peter Stein was a man who loved oysters.

Peter Stein Peter Stein owns Peeko Oysters, which is on Long Island near New Suffolk, NY. He can’t remember a time when he didn’t love oysters.

In 2016, Peter was a man who loved oysters and had a plan to make a living by farming them.

By early 2020, Peter had 2 million oysters in the water and was selling them to New York’s top restaurants, where patrons ordered them nearly as fast as he could grow them—as though each one contained a pearl.

In half a decade, Peter went from being a fan of oysters to a man selling them hand over fist. How did he do it?

Sure, a big part of the reason for Peter’s success is that his oysters are delicious; if they weren’t, no one would buy them. Ultimately, however, the reason Peter’s business is so successful is that he pays close attention to every aspect of his operations.

Whether he’s figuring out the best place to source baby oysters, refining his process to grow them into adulthood, or marketing to the restaurants that will ultimately serve them on plates of crushed ice or in bowls of creamy chowder, Peter has his business down to a science.

If you want to boost your margins, you’ll want to think about operations the way Peter does. That’s what we’ll focus on in this chapter. Thinking through the processes and mechanics that make your company run is the difference between customers leaving your store happy and customers grumbling while they stand in a line that never seems to move. It’s the difference between razor-thin margins and more comfortable margins. It’s the difference between your company becoming a hobby that fades or a business that lasts.

Nailing down your operations—making sure your company is efficient and effective—will also make it possible for someone else to run your business. That’s handy when you want to take a day off . . . or, one day, sell the company and retire or move on to something else.

Make the Thing You Make

Operations is about how your company gets from an idea to a finished product or service that it can sell to customers.

“Operations is essentially process management,” says Lisa Skluzacek, operations manager for Nature Valley Innovation at General Mills in Golden Valley, Minnesota. “You figure out your target customer and look at how you will get every item on your business menu into that person’s hands.”

Under the umbrella of operations, you’ll find logistics, sourcing materials, inventory management, distribution, and sales processes. Within each category, you’ll also find yourself asking all sorts of questions.


Lisa Skluzacek Lisa Skluzacek is operations business manager for snacks at General Mills’ snack division in Golden Valley, MN. She has worked for General Mills since 1991 and is also an avid sailor and farmer.

“If you’re moving things in and out of your warehouse, how many loading docks do you need? If you’re delivering bread, how many trucks and drivers do you need? Do you have enough cold storage for the butter? What’s your timing on all of this?” Lisa says.

She adds that many small companies don’t consider these business dynamics enough. “They just do it,” she says. “But if you’re going to grow your business, you need to think about how your jobs break down into component pieces, so that more people can do those jobs.”

As a small business owner, you want every step of the process to run as efficiently as possible. That means you’ve got to get down to the nitty-gritty details.

Use Data to Design an Efficient Workflow

Whether you’re a sole proprietor or leading a staff of dozens, spend time observing and refining your work process. Standardize the things you routinely do, and document your system. That way, if something in your process goes awry or feels inefficient, it will be easier to identify the problem and test new solutions, rather than having to reinvent the wheel every day.

Jonathan Sciabica Jonathan Sciabica runs Sciabica Family California Olive Oil & Gourmet Foods. His grandfather and great-grandfather began the business using knowledge they brought with them from Italy.

Sometimes, your eyes will fool you. When you can, gather actual data and then use that data to make intelligent changes. Are there ways to improve trouble areas? Look at the step before and the step following a problem to get a broader perspective. Look for bottlenecks, too. For instance, maybe you’re spending a lot of time managing your inventory. In that case, an automated inventory management system might save you time; it could also save you a lot of money.

Information can also help you improve your product. At Sciabica Family California Olive Oil & Gourmet Foods in Modesto, California, Jonathan Sciabica found that exchanging tall, thin bottles for shorter, squarer models both streamlined shipping and made the oil more practical for consumers to use. Why? Because the old bottles didn’t fit on most kitchen shelves. The new ones do. The old bottles didn’t mail in standard-size boxes. The new ones do. Sometimes it’s that simple.

Consider how you’ll manage variability. Every business has slow days and weeks, as well as times when they’re virtually “on fire” with orders coming in. How will you handle those surges and declines in demand?

Drafting a clear workflow makes training employees easier, because you’ll know exactly what they should be doing, and they can go back and read it over if they need a reminder. It also makes it easier for employees to step in and take your place, temporarily or permanently, if you need to take a vacation or want to retire.

Hold meetings to talk about how your team is functioning. What’s working? What could be better? Don’t just talk; listen to their ideas, too. These meetings shouldn’t be about pointing fingers, but about ironing out the kinks in your process.

Source Raw Materials

Every business that sells a tangible product needs raw materials. For Peter Stein, that includes space in the bay, called “bay bottom,” and baby oysters. He’s put a lot of thought into how he sources both.

There are two ways to grow oysters in New York: you either own bay bottom or you lease bay bottom from the county. Leasing requires less up-front money than buying, but it requires much more patience. Peter works in Suffolk County, which holds just one annual lottery for 10-year leases on 60 ten-acre oyster-farming sites.

Alternatively, you could buy bay bottom. That’s what Peter decided to do, purchasing his property from an oyster farmer who was leaving the industry. He could have gotten financing to help build out his operations, he says, but chose to avoid debt by paying cash from his savings.

Owning bay bottom was just the first step. Peter still had to go through an extensive permitting process with the Army Corps of Engineers, the Department of Environmental Conservation, the town of Southold, the Coast Guard, and Suffolk County. “You’re putting things in the water that could be a navigational hazard, so that’s why the Coast Guard cares,” Peter says. “The US Corps of Engineers gets involved because you’re putting things in the water that could disintegrate.”

Peter navigated the permitting process on his own, without help from a lawyer. But depending on the complexity of the process and your expertise in the industry—as well as time and money constraints—you may choose to bring a lawyer in to help, and that’s fine, too. “There’s no playbook for this,” Peter says. “Anyone who starts a business needs a certain kind of grit and persistence. In food production, you bring that to another level. You’re producing something that people are going to consume, so food producers are more heavily regulated and scrutinized by governmental agencies.”

Peter adds that he was pretty sure he could create a viable business around oysters, and that optimism kept him going as he slogged through the permitting process. “I know a lot of people in the restaurant business in New York City, so I never doubted that there was a market and I could access it,” he says.

Once you know what your raw materials will be, you need reliable ways to source them. With access to bay bottom and permits in place, Peter needed baby oysters and oyster hotels for them to live in and grow. The oyster hotels use a tray system, with trays made of steel mesh. Peter decided not to build the cages himself. “I could have learned to weld, but it’s more efficient to let other people assemble our cages,” he says. “My time is more valuably spent selling oysters to top restaurants.”

In nature, baby oysters, also called oyster seeds, float around for two weeks, then latch onto a surface in the bay and start growing. Stein buys his oyster seeds when they’ve already grown substantially, because it means his process will require less labor—and the oysters are more likely to survive.

“You pay more, but you have less labor and mortality, plus the oysters are easier to handle, because they’re bigger,” Peter says. “How much time do you have to wait? How much labor are you willing to put in? Those are questions you have to answer.”

Find the Right Suppliers

There aren’t many oyster hatcheries on the East Coast, and not every hatchery sells oysters at the bigger size Peter prefers. That narrows his choices. He also has to think about transportation. “Going to Maine means two days of travel time, so I like hatcheries that are closer to me and don’t require a truck, a trailer, or a very expensive UPS bill,” he says.

Peter tracks the performance of oyster seeds from different hatcheries to help him decide if paying more or using hatcheries that are farther away makes sense for his bottom line. That’s how he decided against driving to buy oyster seeds from an attractive hatchery in Cape Cod, Massachusetts. “They’re more expensive and they aren’t materially better,” he says. “Why pay 20 percent more?”

LaTonia Cokely LaTonia Cokely owns Adjourn Teahouse in the Washington, DC, metro area. She wanted a tea and wellness brand for years and started Adjourn when her husband gifted her the incorporation details for Christmas.

Over the past four years, Peter has used five or six different hatcheries. He’s continuing to refine his opinions about which of those offer the best value.

Another small business owner, LaTonia Cokely, who runs Adjourn Teahouse in Washington, DC, also works to track down the right suppliers for the tea blends she creates. “I do a lot of research for my supply chain,” LaTonia says. “I belong to a network of similar businesses where I can talk with owners and connect with their distributors.”

That strategy has connected LaTonia with five different herb sellers, but she prefers to buy directly from farms. They tend to have the sustainably sourced, organic options her customers prefer. Expense, availability, and consistency also matter to her—and to the people who buy her products.

It’s not possible to get every ingredient for each of LaTonia’s teas all year round—a problem she solves by offering both signature teas, which have readily available ingredients, and limited editions, which have ingredients that are more difficult to find. “I’m always looking for additional possible suppliers,” she says.

Manage Inventory

Peter started his business with three oyster hotels. Now, he has about 130. That’s around 2 million oysters in the water, all of which need regular inspections for growth rate and disease.

To keep track of his inventory, Peter knew he would need software. At first, he tried to build it himself, coding a product that would geo tag oyster hotel locations through his cell phone. But, before long, he joined forces with someone who was creating similar software, becoming a beta tester. “It’s easier to tweak existing software than to build it from the ground up,” he says.

He’s working to make his OysterTracker software 100 percent accurate, but Peter says that he can’t let perfect be the enemy of good. “I’ll take 80 percent accurate today over 100 percent accurate three months from now,” he says.

Oysters grow during the summer months and are dormant through the winter, so it’s up to Peter to make sure that he’s balancing supply and demand throughout the year.

“Software helps me keep track of that inventory,” he says. “If I’m selling 10,000 oysters a week and I have 30,000 oysters in the bay, I know I’ll be out of oysters by the new year. Or, if I have 300,000 oysters in the bay, I need to get a giddyap on my sales, or I won’t have room for the next batch of oysters.”

In addition to planning his sales, Peter needs to anticipate his needs for staff and gear. He has a boat and a minicrane system, in addition to the oyster hotels, which all cost money. Year-round, he has two full-time employees, but during the summer, he hires part-timers as well. “I get data and I plan accordingly,” he says.

Get Your Manufacturing Process Right

Peter’s manufacturing process involves leaving oyster seeds in the bay and waiting while the oysters grow themselves—for the most part. He also runs the growing oysters through a tumbler every three to six weeks during the summer growing season. Bouncing around in the tumbler, which looks like a giant bingo cage, chips off shell length and encourages the oyster to put energy into growing a deeper, harder shell. “It’s a little like pruning a plant,” Stein says.

For many other firms, manufacturing is more complicated. Zellee Organic, a snack business based in Hawaii and Northern California, started with a family recipe. But the owners quickly realized that there’s a big difference between a recipe that makes enough for four or five people and one that makes thousands of servings. “I spent hours and hours making various recipes,” says co-owner Lisa O’Kelly. “Once we were happy with our formulation on the stovetop, our contractor food scientist helped convert the measurements to the batch requirements. We did many test runs as well at the co-packer.”

Lisa O’Kelly Lisa O’Kelly is cofounder of Zellee Organic, based in Maui, HI. The company makes an organic, plant-based fruit jel snack that uses konjac, a plant from East Asia, to gel the product, instead of gelatin.

Like Zellee, you’ll also need to choose how you’ll package your product, which can be easier said than done. At first, Zellee couldn’t find anyone to produce squeeze pouches, since manufacturers in the United States sometimes required minimum orders of millions of packages. “We were a small startup and didn’t have the capital to meet the minimum requirements,” Lisa says.

But Zellee eventually found a plant in California that had squeeze pouch equipment left over from another client and was willing to try a run of 30,000 pouches. They couldn’t find a plant that was willing to do small production runs, so Zellee next tried a plant in Utah. “That experience wasn’t great,” Lisa says. “They were also new and there were a lot of hiccups. Along the way, we should have talked to the factory’s other clients. If you look at other companies’ packaging, you can get a good sense of where it’s made. Call them up and ask if they’re happy, or ask the packager to offer references.”

Zellee has since moved to a larger, more established packager, which has enabled it to increase production runs with confidence.

It’s important to have mutual trust with your co-packer. “As with most things, having strong, honest relationships with your partners is a must,” Lisa says. “You grow together.”

Optimize Your Distribution Plan

For Jonathan Sciabica, owner of Sciabica Family California Olive Oil & Gourmet Foods, packaging and distribution go hand in hand. It started with Jonathan’s realization that he needed to get his product to online purchasers more quickly. “People put olive oil on the grocery list when they run out,” he says. “It was taking 10 days for us to get oil to retail customers, and by then, they’d have bought something else.”

Flat-rate boxes and padded envelopes from the post office came to the rescue. “The flat-rate padded envelope has changed our business,” Jonathan says. “The post office rep drops off pallets of boxes and padded envelopes, and then they pick them up, filled with bottles of olive oil.” The orders usually reach customers in just two or three days, even in Alaska and Hawaii. (Delivery speed dropped during the Covid-19 pandemic in 2020 but rebounded in 2021.)

Next, Sciabica adjusted its bottles to fit better inside the boxes and padded envelopes. At the time, tall, thin bottles were in vogue. The company could get 250-milliliter bottles of this shape into a flat-rate box or envelope, but its 500-milliliter bottle didn’t fit.

Sciabica redesigned its bottles to be shorter and broader. Now the company can fit two 500-milliliter bottles in a flat-rate padded envelope, and five bottles into the medium-sized flat-rate box. “Understanding how purchases happen and making the appropriate changes has let us offer Amazon-level service through the post office,” Jonathan says.

The company made another helpful change when it began offering its product in a bag-in-box container, which uses plastic bags rather than bottles. Olive oil normally oxidizes after about three months in an open bottle. “It gets bland and starts to smell like crayons,” Jonathan says. For that reason, the company wanted to get rid of its half-gallon jug.

The University of California at Davis released a study on the benefits of bag-in-box for olive oil, and Jonathan was intrigued. “Bag-in-box technology was associated with cheap wine, and that’s unfortunate, because the packaging isn’t cheap and it protects the wine better,” he says. “Olive oil always gets used over time, so it makes even more sense to bag-in-box it.”

Jonathan found a manufacturer that could handle making the bag, then had the box made locally and bought a machine to do the filling. “We created a product that you can use over six months with no oxidation,” he says.

When it comes to distribution, you’ll have a few choices to make, depending on the type of business you run. Sciabica distributes to online customers through the mail. Restaurants can use delivery services like DoorDash or Postmates. If you’re distributing nationwide, you might use private distributors to deliver your products in bulk. Many small consumer brands are starting to use e-commerce platforms as distribution channels. They can drop-ship their products straight to a fulfillment center, never letting it sit in local inventory at all.

But for many businesses, outsourcing distribution isn’t worth it. Peter Stein, for instance, strongly believes in selling directly to restaurants.

“No distributor cares more about my product than I do,” he says.

He handles the deliveries himself and likes having individual relationships with the chefs and restaurant owners who buy his oysters. That, he says, is because purchasers are more likely to be loyal to someone they know, and he’s able to fix any problems on the spot, by comping or replacing an entire order if something goes wrong.