On this special segment of The Full Ratchet, the following Investors are featured:
- Jon Callaghan of True Ventures
- Willy Schlacks of EquipmentShare
- Natalie Dillon of Maveron
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.
We’re proud to partner with Ramp, the modern finance automation platform. Book a demo and get $150—no strings attached.
Want to keep up to date with The Full Ratchet? Follow us on social. You can learn more about New Stack Ventures by visiting our LinkedIn and Twitter.
Transcribed with AI:
0:19
Welcome back to utfr On today’s special segment, we ask guests to tell the most important lesson that they’ve learned in their career. Here’s a segment called Lessons Learned. On today’s special segment, we have John Callahan of true What’s the biggest mistake or the hardest lesson you’ve learned as an investor,
0:42
I focus a lot on understanding time, and I focus a lot I think one of my superpowers, this is not exactly how you frame the question, is in staying in my zone of genius, the biggest mistakes are when I get pulled for some reason or another out of those zones into zones of excellence. And what I mean by that is, like, I’ve been on a million boards, and you got to be on a good director for that, right? But like, trivial examples that I always talk about, it’s like, that’s that’s not often the most impactful way in particularly in early stage, for for for me or one of my partners, to to truly help and impact and sometimes it is and sometimes it’s not, but the biggest mistakes that I look back on have been where I’ve not recognized where to deploy my time correctly. Another one is not carving out enough creative time for like, I protect our team’s creative time and my own creative time, like, viciously. And what I mean by that is I don’t want us over scheduled. I want us to be able to meet enough for this morning group on it tonight, meeting it tomorrow morning. I want us ready for that bolt of lightning. And that is how those bolts of lightning happen for us. So there’s something in in this, in this biggest mistake, kind of category of times at which I haven’t, either for me or for my team, prioritized staying in the creative prepared for the creative moment life happens, the business happens and gets bigger, misreading people, which is just a human thing, misreading alignment, that’s caused a lot of a lot of mistakes over the years, but I, but I would continue to, and I do continue to believe in the best in people and in humanity, and occasionally I’m surprised, rather than the opposite, which is not the way I choose to live. So I I accept it, even though that’s burned me a couple times. It’s it’s part of the way I want to run my day and live my life.
2:34
On today’s special segment we have. Willie schlacks from equipment chair, Willie, can you tell us a story highlighting a critical lesson that has changed the way you lead. I
2:42
thought I was incredible at influencing people, and when I was young and naive, I am not. Now, a big part of that is because people change for themselves, not for you. They’re happy to engage with somebody who’s engaged with them. But it took me freaking forever to understand or realize the amount of energy I was putting into this segment of my imagination that I was somehow effective at changing people now I don’t regret it, because then to come on the other side of it and realize that that is not a useful expenditure of my energy was a freedom setting, like absolutely incredible. So when I do encounter folks that are younger and appear to have a similar behavior as me, I’m like, tap the brakes, yeah, just relax a little bit. And for me, I think there was an ego trip there too. Like, ego loved it, and it just keeps reinforcing this false perception of how you know how much you’re part of the story, and it was, but on the other side of it too, to not have to act on those urges and that ego trip opened up so many other doors for what I could spend my energy in fast doing that. Yeah, that’s probably one of the more more valuable lessons. I acknowledge that I’m saying that because we’re sort of riffing on this topic, topic, but it does feel like if I were to pick one of the more impactful things, that would be the one on today’s
4:01
special segment we have Natalie Dillon of maverick. Natalie, what is the biggest mistake or hardest lesson you’ve learned as an investor, and what’s the story behind it?
4:11
I feel like every day I’m like learning in this job, which is one of the nice and very frustrating parts of the job, but in the 2021 craziness, I was fortunate to be part of companies that had really high, high ramps, and had companies that were marked up by great investors and big funds. I was also more junior in my career at that point, and sort of assumed like bigger fund, bigger investor, they’re going to really dig in, and they’re going to be they’re going to hold the founder accountable. And I think that’s, you know, there’s always exceptions, and bigger fun doesn’t necessarily mean that they will be as engaged. And I think as an early stage investor, you’ve, you have this, like, wonderful, rich history with the founder. You know where they’ve hit plan or where they haven’t hit plan. Or were they over exaggerate or under exaggerate? And I don’t think I appreciated sort of the value of that work, sort of how you have to continue to be that person, regardless of other investors that enter the boardroom. You have to keep the founder accountable. And so that was lesson one. And then I think Lesson Two has been, how do you have those direct conversations with founders when it’s uncomfortable, right, when, and ideally, you, frankly, are having those direct conversations when things are going well, right? You still need to push people to be excellent and and, but learning sort of that rhythm and like, how to establish trust, and how to do that in a way that you’re building credibility versus tarnishing the relationship. And I think my at times inability to do that in the 2021 era, and thinking others around the table who are more senior have bigger funds, like they’ve done this before. We’re going to do it. You’ve got to do it, like at the end of the day, it’s like, you’ve got to have those conversations. And because you’ve been there at the earliest days, there’s actually so much trust that you can lean into. And that’s been a big lesson, and I hope now, like big superpower that I have
6:21
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.
