Alexa von Tobel (Inspired Capital) - The evolution of New York's startup ecosystem, staying price discipline and what it means to be a generalist


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My guest today is [Alexa von Tobel](, Founder of [Inspired Capital]( and [LearnVest]( Inspired is a generalist fund based in New York City that backs early-stage founders with transformative ideas. Some of their companies include Chief, Geneva, Public and Snackpass. They recently closed their second fund of $281 million investing in seed and series A companies. She also founded LearnVest, which was an American financial planning company which she sold for $250 million. In this episode we discuss how New York's entrepreneurial and venture capital scene has risen in the past 15 years, her approach to investing as a generalist and staying price disciplined in this current market. Without further ado, here's Alexa.

Some of the questions I ask Alexa:

1. So what inspired you to start Inspired Capital?

2. How did the fund come together?

3. What was fund 1’s focus?

4. Unfair advantages?

5. Operational experience to be a great investor?

6. What were some of your biggest learnings through fund 1?

7. How do you approach investing at seed and Series A?

8. How has New York transformed as a startup and venture ecosystem in the past 15 years?

1. What verticals in New York are you most excited about?

9. How is fund 2 going to be different from fund 1?

10. How do you think about price discipline in the current market?

11. Is founder-friendly in today’s landscape writing a larger check?

12. How do you approach partnering with founders?

13. Are you finding that founders aren’t always choosing the highest prices?

14. How do you stay price discipline in this current market?

15. What’s your sourcing strategy?

16. What parts of the creator economy excite you?

17. Has COVID changed your mind on any particular verticals?

18. What’s one thing you would change about venture capital?

19. What’s one piece of advice for founders?

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