Recap: Transform Spotlight Series – Leading the Charge: A Female Founder’s Guide to Startup Success

“Look for a way to support another woman every single day” – Kelly Steven-Waiss

The recent Transform Spotlight Series event, “Leading the Charge: A Female Founder’s Guide to Startup Success,” was a captivating interview featuring Kelley Steven-Waiss, author of Valley Girls: Lessons from Female Founders of Silicon Valley and Beyond. Hosted by Samara Jaffe, co-founder of Transform, the event delved into Kelley’s inspiring journey as a female entrepreneur, her challenges, and the invaluable lessons she has learned along the way.

Kelley’s Inspiration to Be an Entrepreneur

Kelley’s entrepreneurial spirit was deeply rooted in her upbringing. With both sides of her family running businesses, she learned firsthand about the sacrifices and rewards of entrepreneurship. Her mother’s late-life career switch to law enforcement and subsequent tragic death in the line of duty further fueled Kelley’s drive to make a meaningful impact. “Her second act became the foundation of my software idea, helping people find non-obvious career paths,” Kelley shared.

Overcoming Key Challenges and Setbacks

Starting a business during the pandemic posed unique challenges. Kelley’s leap into entrepreneurship at 50, amidst sending her children to college, required immense passion and fearlessness. “We launched ourselves, pandemic and all, into the world of entrepreneurship,” she recalled. Kelley faced numerous obstacles, from pitching investors without a typical process to selling virtually to customers, employees, and investors. She emphasized the importance of building a supportive team and maintaining resilience through constant selling and pitching.

Essential Resources

Kelley relied heavily on her network, assembling a “personal board of directors” comprising founders, investors, marketers, and sales experts. This group provided invaluable advice and support, offering a safe space to discuss challenges and brainstorm solutions. “Networking and that personal board of directors were crucial in helping navigate the entrepreneurial journey,” Kelley noted.

Choosing the Right Investor

Kelley highlighted the importance of aligning values with investors, considering them as long-term partners. She advised evaluating investors’ networks, industry expertise, and willingness to offer support beyond financial backing. “Money is not all created equal. You need someone who will introduce you to potential customers or other investors,” she explained.

Why She Wrote Her Book

Kelley’s book, Valley Girls, had three objectives:

  1. Encourage innovation inside organizations and through venture capital.
  2. Promote investment in female founders.
  3. Inspire women to support each other. Kelley stressed the importance of women lifting each other up, sharing a quote from her book: “There are women who reach back and pull others up the ladder and others who pull the ladder up behind them.”

Selecting Women to Highlight in Her Book

Kelley’s selection of stories aimed to showcase diverse experiences across different industries and roles. She emphasized the universal challenges of starting a business by including stories of female investors, like Allison Baum Gates from Semper Virens, and founders. “There are lessons to be learned from every side of this equation,” she said.

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Maintaining Mental Health as a Female Founder

Kelley candidly discussed her struggles with work-life balance and mental health. She emphasized the importance of having supportive friends, partners, and a personal board of directors. “Having outlets and reminders to take care of yourself is crucial,” she advised. She mentioned her husband’s role in supporting her emotionally and practically, as well as her friend Judy O’Brien, who would take her for walks and provide an outlet for her to “dump” whatever she was feeling.

Lessons She Wishes She Knew

Reflecting on her journey, Kelley shared several key lessons:

  1. Be selective about sharing concerns; sometimes, waiting until issues resolve themselves is okay.
  2. Hire well and avoid blind loyalty; ensure team members are held accountable for high performance.
  3. Seek advice and support from your network to cover your blind spots.

Kicking Open Doors Without a Network

Kelley encouraged women to be proactive in expanding their networks and seeking mentors. She emphasized the power of small, consistent actions: “Helping one woman every single day with an introduction or advice turns into 365 impactful actions a year. It scales really fast when we all do it.”

Kelley Steven-Waiss’s journey is a testament to the power of passion, resilience, and community support in achieving entrepreneurial success. Her insights and experiences offer valuable lessons for aspiring female founders and leaders, emphasizing the importance of innovation, strategic networking, and mutual support among women. Kelley aptly said, “If we all support each other, think about the impact we can have.”

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