S1E29: Breaking the Boys Club - Inside the VC Fund That's 70% Female Investors

What happens when a CEO who helped build Old Navy from a startup into an $8 billion company decides to flip venture capital on its head? Dawn Dobras reveals the shocking truth: 93% of venture capital goes to men, and she's built a fund that's 70% female investors to change that.
 
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In this episode, Dawn Dobras exposes why most startup founders get ghosted by VCs (hint: it's not your pitch deck), shares the brutal math behind venture funding (1,000 deals reviewed, only 1-3 funded), and reveals exactly what she looks for beyond the typical metrics.

Plus, she drops game-changing advice on how students are breaking into VC right now without connections or trust funds - including the "shadow portfolio" strategy that's getting MBAs hired.

If you're interested in VC, micro-investing as an Angel investor, or working at a women-led start-up -- this is your episode as Dawn will give you the inside scoop.


Key points:

• Dawn spent 30 years as an operator running companies, including transforming Old Navy from a startup with less than $1M in sales to an $8 billion company, before transitioning to venture capital.
• Only 7% of venture capital check writers are male, with less than 3% of funding going to all-female founding teams and only 2% of healthcare funding directed toward women's health.
• Women invest in venture capital at half the rate of men, largely due to structural barriers including high minimum investments ($500K-$2M) and lack of access to information about the asset class.
• Capital F Fund has over 70% female investors, which is virtually unheard of in venture capital and creates a powerful mentorship network for portfolio companies.
• The fund focuses on three areas where technology shapes women's lives: women's health, digital commerce, and AI enablement, specifically targeting companies with valuations under $12 million.
• Dawn emphasizes that venture funding is extremely selective - they review about 1,000 deals annually and invest in only 1-3, meaning rejection doesn't reflect on the business quality.
• Key investment criteria include emotional resilience and ability to take feedback, as startups face constant challenges and founders must remain open to new ideas and counsel.
• Archive Resale, a portfolio company enabling brands to host resale on their websites, exemplifies the "triple threat" of female founder, climate impact, and tech growth potential.
• Women's health investments include Hey Jane (telehealth abortion care), Stardust (period tracking app designed by women), and Zella Health (AI-powered reproductive health diagnostics).
• For those seeking venture capital careers, Dawn recommends building a track record through shadow portfolios or small angel investments and developing deal flow by networking with founders.

Resources:

• Capital F Fund
• The Council
• Archive Resale
• Forerunner Ventures