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The Full Ratchet

Investor Stories 443. Why Great Investors Move Slowly, Go Deep, and Surround Themselves with the Right People (Hsieh, Madera, Bussgang)

4 min episode · 2 min read
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Episode

4 min

Read time

2 min

Topics

Career Growth, Productivity, Personal Finance

AI-Generated Summary

Key Takeaways

  • Network Strategy: Focus relationship-building on ideal customer profiles aligned with your fund thesis—other investors, fractional executives, wealth managers, and service providers who generate 80% of funded deals at firms like Cypress.
  • Sector Specialization: Select a narrow sector and invest one to three years understanding its dynamics, opinion leaders, and success patterns before making investments to gain pricing advantages and add real value.
  • Investment Pacing: Limit deals to one or two exceptional companies per year rather than five mediocre ones in six months, as weak portfolios consume bandwidth and prevent pursuing breakthrough opportunities three to four years later.

What It Covers

Three veteran venture investors share advice for early-career VCs: build targeted networks, specialize deeply in sectors, and prioritize quality over quantity in investments.

Key Questions Answered

  • Network Strategy: Focus relationship-building on ideal customer profiles aligned with your fund thesis—other investors, fractional executives, wealth managers, and service providers who generate 80% of funded deals at firms like Cypress.
  • Sector Specialization: Select a narrow sector and invest one to three years understanding its dynamics, opinion leaders, and success patterns before making investments to gain pricing advantages and add real value.
  • Investment Pacing: Limit deals to one or two exceptional companies per year rather than five mediocre ones in six months, as weak portfolios consume bandwidth and prevent pursuing breakthrough opportunities three to four years later.

Notable Moment

Busgang warns that new investors can fill their time managing ten to fifteen stagnant portfolio companies, leaving no capacity to pursue transformational deals when they appear.

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Episode Transcript

This episode of TFR is brought to you by Ramp, the spend management platform we use here at TFR. They're offering listeners a $150 just to take a demo. We've never had an offer quite like this. Claim your $150 before this offer is gone at our partner link, ramp.com/partner/tfr. And this episode of TFR is brought to you by the American Arbitration Association, where smart startups and investors turn to for fast, efficient, and cost effective dispute resolution. Visit adr.org/tfr to learn more. Welcome to the podcast about venture capital, where investors and founders alike can learn how VCs make decisions and reach conviction. Your host is Nick Moran, and this is the full ratchet. Welcome back to TFR. On today's special segment, we ask guests for the most important piece of advice that they'd share with folks early in their venture career. Here's the segment called key advice. Today's special segment, we have Vince Shea of Cypress. If you were mentoring a new investor today, what's the single most important piece of advice that you would give them? So the old adage is the network is your net worth. I I think that's most true here in the investing world. Our entire business is trying to get deal flow at the top of the funnel. Like, everything else we do, we have to start with some deal flow. And at Cypress, at least, I'm sure it's true for most investment firms, probably 80% of our our our funded deals come from our network, Our network of other investors, our network of fractional executives, our network of wealth managers, investment bankers, accounting firms, law firms. We spend a ton of time cultivating that network. I think if you're a young investor in the world where you don't necessarily have a network yet, the best thing you do to to, you know, build success for you as an investor is to build up the network through the right type of network, though. Not not going to the wrong events or spending your time with the wrong people. People who fit the let's call it the ideal customer profile, if you will, of your fund or your your investment thesis. On today's special segment, we have Paul Madera, cofounder and general partner at Meritek. Well, if you could share one piece of advice with a young new investor, what would you tell them? I would tell them, be really careful not to do what is the prevalent style today, at least in the late stage world. And that style today in many ways is talking to your buddies and then chasing after the shiny object that that that the shiny company, the interesting company that everyone else thinks is interesting. Instead, you should pick a sector, pick a sector that isn't overly broad, get very smart in that sector, invest a lot of time to understand how does the sector operate, what are the critical dynamics in terms of successful companies …

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