How to Win in Venture & Startups with Taylor Brandt

Taylor Brandt has seen both sides of the table as an operator and an investor. 

Now a newly appointed Partner at Headline, she understands what founders go through because she’s been there. 

In this episode, Taylor shares why great investors need true founder empathy, how she made the leap from growth operator to VC, and what separates the best founders from the rest.from Emmett’s fascinating interview that can help you in your own journey to success.

Listen to Season 3, Episode 17 of Turning Pro on Apple, Spotify, or YouTube.

10 Key Takeaways from Taylor Brandt:

1. Investor vs. Founder Pain: Investors ride the highs and lows, but founders feel them 100x more. Great investors recognize this gap and bring real empathy to the table.

2. Founder Empathy Is Earned: If you’ve never operated, you might be a great investor, but you likely don’t feel founder struggles the same way. Early-stage experience matters.

3. You Need Conviction to Win Deals: Early-stage investing isn’t about picking the best deck. It’s about deeply believing in a founder and fighting to win that deal.

4. Venture Isn't Scalable: Unlike software, VC isn’t infinitely scalable. The best investors ruthlessly prioritize their time between sourcing, portfolio support, and firm management.

5. Startup Success Isn’t Just About the Idea: Many great companies are built by founders who simply fit their market better than anyone else. Founder-market fit is everything.

6. Investor Responsiveness Matters: The best investors don’t go dark. They respond fast, stay engaged, and actively help their founders. But they also know when to step back to avoid burnout.

7. Raising Capital is a Game of Leverage: Too many founders raise too early because they can. The best ones build leverage first, then raise strategically when they have real power.

8. VC Has a Storytelling Problem: Some founders raise easily because they master venture storytelling. But a great pitch doesn’t always mean a great business.

9. True Product Market Fit Is Obsession-Level Customer Love: The best companies grow because customers can’t stop talking about them. When people evangelize unprompted, you’re onto something.

10. The Best Investors Go Beyond the Numbers: Data matters, but gut instinct and deep market understanding separate good investors from great ones. The real skill? Seeing what others don’t.

Taylor’s journey proves that great investing is just as much about conviction as it is about numbers. The best investors get into the trenches with their founders, bring real empathy, and fight for what they believe in.

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