Stop Hiring Advisors Who Want a Retainer (The Equity Playbook) episode artwork

EPISODE · Mar 17, 2026 · 30 MIN

Stop Hiring Advisors Who Want a Retainer (The Equity Playbook)

from We Live to Build

Why do most startups waste thousands of dollars on advisors who deliver zero results? Ron Levin, a partner at Alumni Ventures, explains why you should never pay a retainer to an advisor and how to structure equity-based deals that actually align incentives. In this interview, Ron shares his transition from co-founding TravelPerk (a unicorn startup) to becoming a venture capitalist. He reveals why he prefers investing over operating, the "Cold Outreach" myth that stops founders from reaching VCs, and the new trend of startups hitting $1M ARR before even raising a seed round. He also breaks down his "Super Angel" scout program and why the best founders are often the ones who failed their first time. Check out the company: https://alumniventures.com----------------------------------------------------------------------------------------------------------------------------📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------▶ Get my eBook free - https://welivetobuild.com/network-----------------------------------📈 WORK WITH ME-----------------------------------▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------👀 CONNECT WITH SEAN---------------------------------------------▶ LinkedIn: https://linkedin.com/in/seanweisbrot▶ Inquiries: [email protected]🕒 CHAPTERS---------------------------00:00 - Founder vs. Investor: Which is Better?02:20 - How to Find the "One in a Million" Startup05:08 - Why Venture Capital Still Works (Despite the Failures)07:54 - The "First Check" Myth: Who Really Invests First?08:35 - Why VCs Brag About Seeing thousands of Decks10:04 - The "Cold Outreach" Truth: How to Get a Meeting14:40 - Stop Hiring Advisors on Retainer (Do This Instead)17:00 - How to Use Advisors to Open Doors (The TravelPerk Story)19:50 - My Worst Investment Mistake ($50k to Zero)21:28 - The New Standard: $1M ARR for Seed Rounds?25:40 - Alumni Ventures Investment Strategy (Co-Investing)27:28 - The #1 Career Lesson: Do What You Actually LikeLeave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

Why do most startups waste thousands of dollars on advisors who deliver zero results? Ron Levin, a partner at Alumni Ventures, explains why you should never pay a retainer to an advisor and how to structure equity-based deals that actually align incentives. In this interview, Ron shares his transition from co-founding TravelPerk (a unicorn startup) to becoming a venture capitalist. He reveals why he prefers investing over operating, the "Cold Outreach" myth that stops founders from reaching VCs, and the new trend of startups hitting $1M ARR before even raising a seed round. He also breaks down his "Super Angel" scout program and why the best founders are often the ones who failed their first time. Check out the company: https://alumniventures.com----------------------------------------------------------------------------------------------------------------------------📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------▶ Get my eBook free - https://welivetobuild.com/network-----------------------------------📈 WORK WITH ME-----------------------------------▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------👀 CONNECT WITH SEAN---------------------------------------------▶ LinkedIn: https://linkedin.com/in/seanweisbrot▶ Inquiries: [email protected]🕒 CHAPTERS---------------------------00:00 - Founder vs. Investor: Which is Better?02:20 - How to Find the "One in a Million" Startup05:08 - Why Venture Capital Still Works (Despite the Failures)07:54 - The "First Check" Myth: Who Really Invests First?08:35 - Why VCs Brag About Seeing thousands of Decks10:04 - The "Cold Outreach" Truth: How to Get a Meeting14:40 - Stop Hiring Advisors on Retainer (Do This Instead)17:00 - How to Use Advisors to Open Doors (The TravelPerk Story)19:50 - My Worst Investment Mistake ($50k to Zero)21:28 - The New Standard: $1M ARR for Seed Rounds?25:40 - Alumni Ventures Investment Strategy (Co-Investing)27:28 - The #1 Career Lesson: Do What You Actually LikeLeave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

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Stop Hiring Advisors Who Want a Retainer (The Equity Playbook)

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This episode was published on March 17, 2026.

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Why do most startups waste thousands of dollars on advisors who deliver zero results? Ron Levin, a partner at Alumni Ventures, explains why you should never pay a retainer to an advisor and how to structure equity-based deals that actually align...

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