On this special segment of The Full Ratchet, the following Investors are featured:
- Jim Tananbaum of Foresite Capital
- Eric Ries Author of The Lean Startup
- Grant Demaree of Onebrief
We asked guests to tell the most important lesson they’ve learned in their career.
The host of The Full Ratchet is Nick Moran of New Stack Ventures, a venture capital firm committed to investing in founders outside of the Bay Area.
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Transcribed with AI:
0:19
Welcome back to TFR. On today’s special segment, we ask guests to tell the most important lesson that they’ve learned in their career. Here’s the segment called “Lessons Learned. On today’s special segment, we have Jim Tannenbaum of Foresight Capital. What is the biggest mistake and/or hardest lesson you’ve learned as an investor, and what’s the story behind the lesson?
0:44
I think there are two. There are two sets of two sets of lessons. One lesson has to do with the prematurely getting out a winner’s lesson, because that has by far the biggest impact on a fund. We’re getting better at it, but I would say that over the course of 10 years, when you have a conservative organization. There’s a bias towards seeing the glass not being, you know, sort of half full, and and then that bias is, you know, occasionally towards early distributions or early sales of things that then end up delivering another 5x of performance. And I say that’s the biggest sin and and the most painful sin that venture capitalists can make. The other side of it, from time to time, you have entrepreneurs that are zealots. That zealotness leads them to put together stories that are compelling. Unless you check every single fact, then the question becomes just how much fact checking, like, do you want to do when you’re in business with somebody? We’ve definitely had a couple painful lessons. We should have checked every single fact, and in some cases, people you know were right at the line. In one case, over the line in terms of you know you know what what they were telling us and allowing us to do. You know those are the tough ones, and and what I think we’ve learned through the years is how to have that difficult conversation in the you know in the lowest energy kind of way, so that we can you know we can get to the bottom of everything without basically calling questions unnecessarily or doing anything that creates extra energy. But that’s definitely an art. It’s definitely been a place where I wish we had we had pushed a little harder in a couple circumstances as well. Brenna
2:23
Emery joins us today from the Bay Area. He’s the CEO and founder of One Brief, the defense company building the operating system for military planning. Can you tell us a story highlighting a critical lesson that has changed how you lead?
2:36
So, Lou Craparparata, or Lieutenant General retired Luc Crapora, he was a Marine Corps general. He was an advisor to me for a long time before becoming a board member here. In the early days of the company, I was not in good health. There was a year where I traveled over 250 nights. I tried really hard to get a lot of exercise. I tried really hard to make it work out, but like, there’s only so much of that you can do, and some of that was self-imposed, and in hindsight, not totally necessary. I I was about 20 pounds heavier than than I am now, which was very unusual compared to like my you know military fitness, and I was pretty sad about it. And I was getting sick like twice a month, and it’s it’s just very hard to show up the way you need to at at that stage, he was like, “How well you sleep is is the decider of of how good or bad you’re going to do in leadership. You must find a way to make yourself sleep. That was actually the whole advice. Eventually, problem solve that. From okay, here’s how I can make the room cold enough. Here’s how I can get enough exercise. Here’s how I can make sure I have zero caffeine, except in the early morning. Here’s the the many other things I can do. Here’s how being concerned about these 100 issues immediately before bed is like fundamentally unproductive. But you gotta sleep, and as a early stage founder, if you’re like a little proud of, hey, I can fight it out. I know I can succeed. It doesn’t matter how little sleep I got. I will stand and deliver and figure this out, or I will make however many sacrifices I’ve got to make. I get it, and that’s not an attitude that’s going to carry you into really effective leadership, and saying no, no, no, this is a top priority problem. You must figure out how to sleep. I think is is the the leadership lesson on being able to to show up for the people and make some make some decisions.
4:36
It’s kind of engraved in us to just show up and perform, regardless of yeah how much sleep you got or you know whatever it is, but that’s that’s great simple advice. Everybody can fix that.
4:54
On today’s special segment, we have Eric Ries, founder of the Long Term Stock Exchange and author. Of the lean startup and incorruptible, Eric. What is the biggest mistake or hardest lesson you’ve learned as an investor, and what is the story behind that lesson? Opportunity costs are always
5:10
the highest. Like it’s you know, it’s not the things I’ve invested in and lost money on. It’s the things I could have invested in and didn’t. I told the story about Dario coming to meet with me. I didn’t even try to invest in the company. I was like, ah, that’ll be rude. I don’t want to be, I don’t want to be gauche. Like he’s come to me for help on something substantive. We didn’t, we didn’t even discuss it. And you picked in the iconic big company of the last 20 years. Like I could have gone there as an employee or as an investor. Like early on, like I sat with Mark Zuckerberg and Cheryl, and I and Cheryl gave me the rocket ship speech, and I was like, nah, not that interested. Like could have gone to Google. I’ve missed them all, so don’t take investment advice from me. Very expensive mistakes, but you can’t be in this business like you just can’t be in this business if that kind of thing bothers you. It just just would drive you crazy.
5:55
That will conclude this installment of Investor Stories. If you’re enjoying the program and would like to see it continue. Take a moment and leave a five-star review in iTunes. Okay, that will wrap things up for today. Until next time, over prepare, choose carefully, and invest confidently.
