The Full Ratchet Podcast: Investor Stories Lessons Learned

Our Managing Partner, Brian Hirsch, sat down with Nick Moran, host of The Full Ratchet, for a special episode on lessons learned from investors. Brian is joined by Brendan Wallace (Fifth Wall), Tim Guleri (Sierra Ventures), and Dharmesh Thakker (Battery Ventures) for this episode. Each investor shares critical lessons about startup investing and how they’ve refined their investing approach over time.

Brian has invested across various sectors over the past 20 years, including fintech, enterprise/SMB SaaS, marketplaces, healthcare, martech, edtech, and proptech. He was or is responsible for the following TVP investments: ACV Auctions (Nasdaq: ACVA), AiCure, AlphaSense, Bakpax, CommonBond, Cuebiq, Honeybook, Katapult (Nasdaq: KPLT), Lendio, Mighty, Ozobot, ShopKeep (acquired by NYSE: LSPD), Suzy, Thinkful (acquired by NYSE: CHGG), Truveris, Visibly, and Vivvi.

Here are a few highlights from Brian’s conversation with The Full Ratchet. You may also want to check out the full episode of The Full Ratchet: Investor Stories Lessons Learned HERE.

What’s a critical lesson that has changed the way you invest?

The critical lesson I learned 5–7 years into my career is that not investing is a decision (to be honest, I probably learned this later than I should have). This is important since every investor feels like they need to do a lot of deals to build their track record and make their mark in the industry. As a VC, you are with these investments for a very long time (longer than the average marriage in the US), so it’s important to make sure you believe in the business and enjoy working with the team. Every day you’re making a decision, and it’s OK if the decision is not to invest.

How do you know when it’s the right decision or when it’s an investment that you’re excited about?

One of the ways I’ve learned to assess this over the years is to be in tune with my level of excitement about the business after the meeting. When I meet with an entrepreneur, and I find myself constantly thinking about the company and coming up with ideas for opportunities (this doesn’t happen a lot), I know this is something to consider. And if I really love the business, I sometimes get this thought that if I weren’t a VC, I would be excited to run this business as a CEO. Every time I’ve had this feeling and invested, it’s worked out for us.

Listen to more episodes.

You may also want to check out Brian’s first podcast with The Full Ratchet from earlier this year, The Full Ratchet: Maintaining a Disciplined Fund Size and Strategy, The Rise of NYC Tech, and Changes in the Exit Environment HERE.