We All Fail - Let’s Get Better at It

Learning from missed deals, tough pivots, and the lessons they leave behind

July 08, 2025

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💡From Our Team

In venture capital, failure isn’t the exception—it’s the expectation. Most investments don’t return, most startups don’t scale, and most founders get told “no” before they ever hear “yes.” This week, we’re diving into the role failure plays in success—from investors and founders who’ve lived it, and what we can all learn from it.

📈VC Success Rates: The Math Behind the Model

In venture, even the best portfolios have a high failure rate:

  • 65% of startups return less than investors put in

  • 1 in 10 investments typically drive all the fund’s returns

  • Only ~4% of VC-backed startups ever exit above $100M

  • Most VCs rely on a few “home runs” to make up for the many misses

This is why portfolio thinking matters. VCs expect failure—it’s priced into the model. What matters most is learning, pattern recognition, and doubling down when you see traction.

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💸 Bessemer’s Anti-Portfolio

Bessemer Venture Partners famously publishes an “anti-portfolio”—a public list of all the companies they passed on that went on to be wildly successful.

Included on the list?

  • Airbnb

  • Google

  • Tesla

  • Apple

They missed these bets for reasons that, at the time, made sense. But the lesson isn’t just that they were wrong. It’s that everyone is, sometimes—even the best.

You’ll never catch every winner. Success in VC is not about being perfect, but about being thoughtful, open, and willing to keep learning.

[note: Girls Into VC founder Isabella is working at Bessemer this summer!]

👩‍💼Founder Feature: Payal Kadakia, ClassPass

Click to read more!

Payal Kadakia is the founder of ClassPass, now a $1B+ company that revolutionized the fitness industry. But it didn’t start that way. Her first three product launches failed. Investors didn’t believe consumers would book workout classes online. Studios weren’t interested. People didn’t understand the platform.

So she pivoted—again and again. Eventually, the core idea stuck. Kadakia has spoken publicly about how customer feedback, patience, and adaptability turned her early failures into strategic wins.

“I only started to succeed when I stopped clinging to the first version of my idea and really started listening to what people needed.”

- Payal Kadakia

❗ Startup Highlight: Frnds of Frnds

Meet Frnds of Frnds, a Washington, D.C.–based startup that’s making dating safer, more authentic, and way more fun. Founded by Shayna Ellis, a Georgetown student and former BCG intern, the app uses your contacts to create a curated dating pool of people who share mutual connections. The result? A tighter, more trusted circle for online dating—think less swiping in the dark, more meaningful matches.

Shayna got the idea in fall 2023, during her first real break from the structured recruiting cycle. "So many of my friends had been complaining to me about the quality and safety of dating apps like Hinge," she shared. "I met my boyfriend through mutual friends, and the idea kind of just popped into my head."

She teamed up with her longtime friend Jake, a software engineer at the University of Michigan, and together they dove headfirst into building the app—handling everything from design to marketing to code. “It’s been really stressful but also so rewarding to get to work on something that I’m so passionate about,” Shayna said. “We've already hit a great user base with our public beta even before we've launched officially!”

For Shayna, this startup journey has been a return to something she always dreamed of. “Growing up, I had always wanted to be a founder, but I sort of settled into the college culture of feeling that I had to pursue the ‘right’ track,” she reflected. “Even if Frnds of Frnds doesn’t ‘succeed’ in typical terms, the value of the experience makes me feel like it’s been a success already.”

And her advice for other aspiring founders? “There is literally no downside to putting yourself out there if you have an idea and want to pursue it,” she said. “Every idea that isn’t attempted is an idea lost—and I think a lot of women naturally feel like their ideas aren’t worth executing, but they are!”

💼 Opportunities

In Boston? Attend this workshop on July 29th on women’s financial wellness! here

Costanoa Ventures is hiring an associate to join the team in San Francisco here

776 is hiring a venture capital analyst! here

✨ Girls Into VC Update

2025 Fellowship Session 4 Recap: Breaking Into Venture: Where to Start?

This week in the Girls Into VC Summer 2025 Fellowship, we focused on practical, strategic steps to build a career in venture capital—from internships to full-time roles. Whether you’re early in your journey or refining your path, here are the key takeaways:

📚 1. Keep Learning

VCs are curious by nature, and the best way to grow is to stay informed.

  • Tune into podcasts like 20VC and Acquired for insights from both founders and investors

  • Dive into Venture Deals and The Lean Startup for foundational knowledge

  • Follow newsletters (like ours!) and use LinkedIn/blogs to stay up to date on trends, deals, and people in the ecosystem

🤝 2. Build Genuine Connections

Relationships open doors. Make them intentionally.

  • Do your research before reaching out

  • Craft thoughtful questions

  • Lead the conversation and always follow up with a thank-you

📝 3. Optimize Your Resume

Highlight leadership, initiative, and relevant skills—even if you’re just getting started. No experience? Start building it now through student organizations, research, or startup work.

🌱 4. Take Initiative

Don’t wait for a job title to act like an investor.

  • Set up meetings with startups and founders

  • Conduct research on sectors you care about

  • Begin forming your own investment thesis

  • Seek out startup experience to sharpen your perspective

This session reminded us that breaking into VC is playing the long game—one that requires being strategic, intentional, and, most importantly, curious. If one path doesn’t work, don’t be discouraged. There’s more than one way in, and every setback is a chance to pivot, learn, and find the route that’s right for you.

💕 At Girls Into VC, we know that failure is part of the journey—it’s what you do with it that matters. Growth comes from how you respond, reflect, and try again. The future of venture will be led by those who embrace both the wins and the setbacks, and we’re proud to be learning, building, and moving forward alongside you.