On this special segment of The Full Ratchet, the following Investors are featured:
- Kevin Stevens of Energize Capital
- Manish Patel of Nava Ventures
- Craig Shapiro of Collaborative Fund
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.
0:35
On today’s special segment, we have Kevin Stevens of energize Kevin, can you tell us a story highlighting a critical lesson that has changed the way you invest.
0:43
Yeah, so kind of tying into the company we missed, we missed the investments that we struggled with the most in our first couple of funds were hardware. And what we learned is that we really need to take one leap at a time. And so if you’re going into so we were going from venture to growth. And so instead of doing hardware growth equity, we should have just done software growth equity, because we were already software investors. And so instead of, you know, trying to make the venture to growth leap and software to hardware leap, we should just make one like, go later stage, keep doing what you’re doing, do what you understand, and that informs a lot of what we’re doing. And we’re thinking about, how do we expand our thesis, or how do we do investments that maybe we’re not comfortable with? We ask ourselves a lot, are we making more than one leap here? Because often, if you’re making more than one leap, you’re increasing the risk and you’re increasing your blind spots. I mean,
1:36
isn’t there an argument that venture is about, you know, leaning into risk as much as possible.
1:42
Yeah, I think that’s true. We get a lot of comments that we look more, even on the venture side, look more like a growth equity firm. I think if you’re a generalist, it is about increasing risk for return. But for us, it’s more being focused. It’s more making sure we’re staying in our lane
2:02
on today’s special segment, we have Manish Patel of Nava ventures. MANISH, can you tell us a story highlighting a critical lesson that has changed the way you invest?
2:09
Yeah, I would say one of the most critical lessons I’ve learned over the years as an investor is think from first principles like the Snapchat story. Don’t follow rules of thumb. Really think from first principles about why is somebody using a product, you know, and do your own research. I think so many times people are dismissive of a great product. Cam is another one in my anti portfolio where I was lucky enough to meet Melanie when she was raising series A and everybody told me, Don’t invest in tools businesses. They’re not good. That doesn’t work, right? And they’re padding pattern matching to like Dreamweaver and other kind of old school businesses. That would have been awesome if I just trusted your instincts, trusted from first principles. Why is this product need to exist in the world?
2:55
It’s amazing advice. Like, you know, I work with my team all the time, and we’re trying to evolve and do better. And if I think about the arc of my career, I went from knowing nothing to knowing a lot, and then you over architect everything based on metrics and checklists and like, and then like, you get a little later in your career and you’re like, you know what? Push all that stuff off your desk and like, just try and find the truth, try and ask the right questions. Try and find people that are cartographers, not navigators, to you know, some construct that doesn’t apply, and it’s, it’s kind of a funny
3:28
art, absolutely. Yeah.
3:35
On today’s special segment, we have Craig Shapiro of collaborative fund, Craig, can you tell us a story, highlighting a critical lesson that has changed the way you invest?
3:44
Well, it’s a it’s a good question. I can’t, I don’t know if there is a specific moment where I learned this lesson, but I think a lot about kind of the value of as an investor, of kind of living at the intersection of naivete and citizen cynicism, meaning, I think when I first got, you know, when I first started investing, I was I was really naive, like I was new to me. There was something that, you know that I was learning kind of as as I was going, and I still am, to a certain extent. But I think sometimes that that bringing a beginner’s mind to it has an advantage. You know, you’ll back things that seem crazy because you don’t know any better. And as you get older, and this isn’t just true in venture but it’s true in most things, you’re the scar tissue. You know, the more times you fall off the bicycle, you know, your body naturally builds up these defense mechanisms so you become more cynical and and I think I try to fight that, because I think you need too much. Which naivete is, is a bad thing, but so is too much cynicism. So there’s, there’s kind of this that the, I think the the most important lesson, or one of the most important lessons, is kind of trying to, to to to balance those two things out. If that makes sense,
5:17
100% Yeah, I was thinking about this the other day. There’s this arc to a lot of people’s careers that I’ve seen where they don’t know much early in their career, and then, you know, they get to maybe early 30s, and they’re pretty dangerous. They know quite a bit. But then, as an investor, you have, like, the curse of perfect, like you’re looking for everything to line up and and then maybe you get older like me, and brain cells are dead, and just it’s easier to make shots that thing on things that don’t look so
5:50
great, totally, totally. It is. I think it’s like that also it happens exponentially the more successful you are, because then your bias is to not, you know, it’s like, we, we, we looked at another, you know, startup in the beverage space, and it was like, Well, we already have, you know, or, or, you know, like, a coffee related startup, and it’s like, well, you know, let’s we, you know, we already have blue bottle, like it’s and so Your bias changes to, like thinking about the downside versus, you know, thinking about the possibilities, which I think is a dangerous thing for venture capitalists, tricky.
6:34
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. Thanks for joining me.
