Venture Capital Icon Reflects on His Best and Worst Investments
EP 100 of The Logan Bartlett Show: Untold stories from tech's inner circle
After 23+ years in venture capital, Jeremy Levine has thrived through many eras, taking risks on now-iconic companies like LinkedIn, Shopify, Yelp, Pinterest, and more. In our discussion, Jeremy shared stories behind these investments and the mindsets he’s developed along the way.
The conversation turned out to be one of my longest and most in-depth to date, an ultimate discussion for anyone that wants to nerd out on venture capital with us. A few takeaways…
Click here to view the episode transcript | Watch on Youtube | Listen on Spotify or Apple Podcasts
✉️ Episode Memo
→ Does price actually matter?
Jeremy’s POV: “The idea price doesn't matter and that it's binary is just wildly flawed and lazy thinking. I think it's just dead wrong.”
The math is undeniable: a venture fund that returned 5x would have only returned 2.5x if you paid double the price for each deal. So, price simply has to matter in aggregate.
Yet, if the only choice is to invest in a startup that will grow 100x, but you wanted to invest at a price that would’ve led to a 200x return, investing at the higher price is still very wise. If we had the benefit of hindsight, VC would be really, really easy.
Regardless, Jeremy avoids feeling FOMO, and instead convinces himself he has JOMO (Joy Of Missing Out), as we all love to avoid wasting time on things that you weren’t actually going to follow through with.
→ Why Jeremy hates investment memo templates
Using templates for investment memos stifles deep, first-principle thinking. Instead of crafting a unique investment story, you’re doing busy work completing a form. While most of the memo can follow a structure, the first page should always be written from scratch. Templates can standardize discussions unfairly, emphasizing the same aspects for every company, regardless if their stand out value is their tech/market/product/etc. Instead, ask yourself “what is the most important thing?” and start from there.
→ Bessemer’s voting system for investment decisions
For every investment decision, team member’s vote on how confident they feel in an investment from 1-10. It serves 2 purposes…
Team feedback: as the lead partner on a decision, getting feedback can help you make a better decision (of which you will be celebrated or blamed for). Numeric ratings help clarify the discussion, as a 10 indicates more concrete approval than just saying "I love it," while a 6 provides grounds to discuss specific pros and cons.
Keeps you honest: The voting process helps minimize hindsight bias by documenting your true confidence level at the time, allowing for a more objective review of your decision later on.
Funny enough, some of Jeremy’s best investments got very weak votes, and we talk through these in the full episode. We also explored how the VC landscape has evolved over the last 20 years and where the industry may head next. Plus, lots of insights from Jeremy’s journey into VC, along with foundational advice and principles that anyone aspiring to succeed in the industry may find valuable
⭐ Trailer
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