Can an ‘Abundance Mindset’ Really Help Female Founders Beat the VC Boys’ Club?

Why Do ‘Dolphin’ Founders Outperform ‘Shark’ Entrepreneurs in the New Economy?

Discover key lessons from Valley Girls by Kelley Steven-Waiss. Learn why the male-dominated startup “playbook” is broken, how “intrapreneurship” offers a safer path to innovation, and why female founders must embrace an abundance mindset to secure funding and respect.

Read the full review below to learn the specific “intrapreneurship” strategy that lets you test your startup idea using someone else’s budget before you ever pitch a VC.

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Business founder and HR executive Kelley Steven-Waiss discusses why women in tech start-ups have difficulty securing investors and earning their male peers’ respect. She pursued a familiar entrepreneurial path: Have a “big idea,” assemble a team, tap your network, seek venture capital – and face stumbling blocks from male investors who sideline female decision-makers. Now, she asks if that playbook is still relevant. Could an abundance mindset replace the typical corporate scarcity mindset? Might founders do better as team-oriented dolphins than as sharks? Drawing from interviews with other female founders, Steven-Waiss argues that the business world needs more women to become entrepreneurs and that they deserve more respect.

Take-Aways

• Women entrepreneurs must embrace robust reality to dispel establishment myths.
• Women have hidden superpowers that grant them advantages.
• Intrapreneurship enables you to experiment with another organization’s money and network.
• Male investors “pattern match,” but women don’t fit the pattern.
• Women investors don’t always advocate for other women seeking venture capital.
• A male-dominated start-up culture may not appreciate women’s unique skills.
• Powerful women must stand by their promises.

Summary

Women entrepreneurs must embrace robust reality to dispel establishment myths.

The numbers tell the story: More women than men are graduating from universities in almost every discipline and women’s presence in the professional workforce is growing. What does this mean for female founders launching tech start-ups?

“My gift was my ability to be a disruptor against the status quo, creative and unconstrained in connecting all my experiences into big-picture ideas.”

Historically, men have dominated this field, and venture capitalists remain reluctant to invest in companies founded by women. The myths about which traits a founder must have to succeed reinforce behaviors that favor men’s dominance in start-up culture. According to these myths:

• Founders are aggressive sharks.
• Founders go it alone.
• Founders are born, not made.
• Founders must be financial pros.
• Founders are inherent risk-takers.

The nuanced realities that counter these myths demonstrate that collaboration generates positive results and that women are well-suited to entrepreneurship:

• Founders are cooperative dolphins.
• Founders nurture allies.
• Founders are made, not born.
• Founders must be creative.
• Founders manage risk.

Human resources executives have a vested interest in optimizing talent and maintaining a skilled, dedicated workforce, today and in the future. They seek ways to encourage people to bring their whole selves to work. Firms should determine what opportunities they need to offer to challenge and engage their staff members – such as access to assignments and projects that suit their skills and support their goals, including leadership and entrepreneurship.

Women have hidden superpowers that grant them advantages.

Female entrepreneurs can’t afford to make missteps and lose credibility. Because they are much less likely than men to secure VC start-up funding, they face intense pressure to perform flawlessly.

“Whenever I wanted to say that I couldn’t do something – that I was a woman, that the idea isn’t good enough, that I wasn’t good enough – I told myself that I had to fight through.”

Female entrepreneurs who learn to anticipate setbacks can bring their superpowers to bear. These include:

• A collaboration mindset – Women understand that collaboration and abundance-oriented attitudes can outperform the usual zero-sum mindset.
• Leading from values and purpose – Women understand culture and can adapt their mindsets to fulfill their firm’s collaborative mission statement.
• Seeing value in teamwork – As an executive, author Kelley Steven-Waiss sought employees who complimented or augmented her skills.
• Identifying the win-win – The win-win mindset is the opposite of the zero-sum game attitude so prevalent in start-up culture.
• What’s in it for me? – Steven-Waiss’s Software as a Service talent mobility company, Hitch, encourages users to be alert for opportunities to learn and to enhance their reputation.

To persevere, you need a great team. To keep it, nurture your team members by heeding their input, sharing the wealth, and investing in their future. Approach every setback with the belief that abundance is power and that your values are more powerful than any fear.

Intrapreneurship enables you to experiment with another organization’s money and network.

Building a company from the ground up is daunting for even the most dedicated entrepreneurs. Why take on all that work and risk alone? While the start-up culture’s lone-wolf stereotype persists among male entrepreneurs, women must struggle enough to attract venture capital as it is. This makes collaborative intrapreneurship a good alternative.

While Steven-Waiss was working for HERE Technologies, she honed her leadership skills, expanded her network, and rose to become chief human resources officer (CHRO). When she had a breakthrough idea for a company offering software that connects employees to resources and opportunities to use their skills, she turned to intrapreneurship and collaborated with HERE in its developmental stages. The leadership at HERE gave her start-up, Hitch, its launch, providing her with a lab where she could conduct test runs for her product. HERE provided expertise, technology, and a tremendous client base.

“Intrapreneurship is the gateway drug for entrepreneurship.” (Adriana Gascoigne, founder and CEO, Girls in Tech)

Attorney Denise Hummel Isaacson, who also has experience with intrapreneurship, advises: “The light, the spark, the insatiable drive to succeed cannot stay alive in darkness.” All entrepreneurs can benefit from intrapreneurship. But Isaacson cautions women who want to start a company to consider multiple challenging factors: budget, staffing, performance evaluation methods, support from internal staff and stakeholders, and access to customers and revenue opportunities.

The obstacles that can hinder a woman’s success include a toxic culture, and leaders or employees who resist change. To combat these forces, remain authentic. Demonstrate the dividends that a win-win abundance mindset offers. Do your work so well that others feel a little fear of missing out (FOMO) if they don’t join your effort.

Male investors “pattern match,” but women don’t fit the pattern.

In March 2020, Hitch had just hit its stride through Steven-Waiss’s network of CHROs when COVID-19 shut down the business world. This put HERE Technology in a tight spot. It had to pivot, and Hitch was in the crosshairs. Steven-Waiss couldn’t let it die, so she had to make Hitch independent and spin it out on its own. This gave her the IP and the responsibilities of raising venture capital and building a clientele. In a world that had suddenly become even more uncertain, she had to prove she could make Hitch connect.

“You have to be smart. You have to make yourself a student of the process, which is exactly what I always did when I took on something really scary.”

As soon as you can, learn how to pitch. Steven-Waiss spent years teaching herself how, but she still felt daunted. Instead of following the myth that founders are lone wolves, Steven-Waiss optimized her network by tapping her friends for advice at every stage in the process. She learned valuable lessons. Venture capitalist Cathy Chiu, a friend, warned that a VC might like Steven-Waiss but not her idea – or might like her idea, but not her.

Steven-Waiss could not bootstrap her company with her own savings or ask her friends with limited resources to invest. She sought female angels – wealthy investors seeking interesting new opportunities. One angel, Judy O’Brien, a former partner at Wilson Sonsini Goodrich Rosati – a Silicon Valley corporate law firm with a specialty in venture capital – joined Hitch’s board.

Steven-Waiss had to go the VC route, even though she knew the statistics. While 40% of US business owners are female, only 3% receive VC. For those who have a man on their team, that number increases only to 17.2%.

Men often decide not to invest in the work of female founders because male investors tend to be pattern-matchers who generally seek to invest in founders whose experiences mirror their own. Women-owned start-ups don’t fit their usual investment profiles. Also, prior success attracts more success and, in start-up culture, male entrepreneurs have longer winning track records.

Women investors don’t always advocate for other women seeking venture capital.

While women occupy positions inside large venture firms, many are junior staff members hired to fulfill diversity requirements. Most women in VC firms still lack the experience and power to make big investment decisions. The top VC echelon is overwhelmingly male, and men ultimately write the checks. General partners often need 10 years of proven ROI success to advance within VC firms.

Female VCs don’t always look out for the best interests of female founders. Companies that raise initial funding exclusively from female VCs are two times less likely to receive funding from male VC partners in the second round of financing. Male founders, who remain more likely to attract investors, don’t have this problem. Female founders may find greater success if they seek VC funding first from male investors.

“I was constantly saying to myself, How can I do this? I don’t have the expertise in this. But I had always risen to the occasion.”

During the COVID pandemic, businesses everywhere tried to adapt to a volatile situation. They had to maintain stability and foster resilience, even while their investors were constantly checking in and expecting returns. Diversity programs, which offered more opportunities to underrepresented social groups, suffered. Simultaneously, the nature of how people worked changed to a remote model, which had repercussions for both start-ups and female founders.

For Steven-Waiss, raising money remained a problem. If it hadn’t been for Hitch’s early female investors, her company would not have survived. She leaned into her network, mostly made up of CHROs, to build her clientele.

A male-dominated start-up culture may not appreciate women’s unique skills.

Steven-Waiss knew she didn’t want to be Hitch’s CEO for the long haul. She intended to put someone else in that role, so she could focus on the go-to-market process, where she could apply her evangelizing skills and draw new customers. Her board members seemed anxious because she was a first-time founder and needed help with operations. The board brought in a chief operating officer in 2021.

Steven-Waiss tried to maintain an abundance mindset and remain open to learning from her new executive. But she knew she was vulnerable. The company needed to move forward – and quickly. Within months, Steven-Waiss had to step aside to let her new COO run the company.

“As we move away from the stereotypes of who can be successful founders and CEOs and who can’t, the type of background that I had and others like me will be more appreciated.”

As women chart their course in leadership roles, their unique skills may find more appreciation and respect. Currently, the market does not value their ability to connect the dots “between what exists and what is possible” as much as it values demonstrable results. Most women executives have exceptional knowledge and expertise. But men tend to discount them as entrepreneurs because they don’t have résumés that resemble a male CEO’s profile.

Steven-Waiss developed her ability to recruit and foster talented people when she was HERE’s Chief Human Resource Officer. These skills are crucial to developing the next generation of leaders – particularly in companies that are alert to succession, another area in which CHROs offer guidance. Any organization’s success rests on its people. Especially in the post-pandemic world, with work changing in fundamental ways, female CHROs have a tremendous opportunity for leadership.

Powerful women must stand by their promises.

When boards of directors seek leaders, they prioritize financial skills over people skills. That’s what they are accustomed to – but change is possible. To achieve it, women must support one another. When women in leadership roles make promises and then renege on them, they undermine the credibility of other female leaders. When a woman gains a seat at the table, she may adopt a scarcity mindset and hunker down to protect her position instead of inviting others to share in her advancement. To change the business world, powerful women must put their words of fellowship into action.

“I decided to…call it out here, on paper: The biggest risk for female founders is female investors putting on a guise of solidarity when their actions don’t align to the mission they espouse.”

Three tech-industry female founders recognized Hitch’s value. They helped Steven-Waiss during the painful (but necessary) acquisition process after she stepped aside as CEO and put Hitch on the market. She wanted everyone involved to win and earn back some of their investment.

ServiceNow’s offer to buy Hitch was exactly what Steven-Waiss had hoped to realize. In the end, she wanted to help service providers, such as ServiceNow, optimize their workforce. ServiceNow, which has the expertise and the resources to take Hitch to the next level, hired Steven-Waiss to run it. While it felt strange to change hats and become an employee instead of an owner, she finds gratification in the results of her hard work and in her ability to earn and promote mutual support and investment among female technology entrepreneurs.

About the Author

Kelley Steven-Waiss, founder and CEO of Hitch Works, Inc., co-wrote The Inside Gig: How Sharing Untapped Talent Across Boundaries Unleashes Organizational Capacity.