On this special segment of The Full Ratchet, the following Investors are featured:
- Madhavan Ramanujam of 49 Palms Ventures
- David Cohen of Techstars
- Victor Orlovski of R136 Ventures
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 etfr 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.
0:35
On today’s special segment, we have Madhavan Ramanujam of 49 palms. What’s the greatest lesson you’ve learned in your work with VCs and
0:42
startups, one of the key lessons that I learned in the last, let’s say, you know, six months or so that we have been, you know, getting the fund off the ground is when we, you know, when we started thinking about our own thesis. We thought that we would be more, you know, relevant in series A or Series B, as in, especially after a product market fit is established, there is a, you know, monetization model in place, and people need to scale it. That’s probably when we can lean in and actually operate the biggest learning and we have now done office hours with over, you know, 100 companies. And what we have actually seen is the our thesis is really relevant even in the pre seed and seed stages, because most of these founders are, you know, thinking about how to navigate POCs, how to actually have commercial discussion. How do I charge it? Goes back to the cost dynamics and the value capture, because the founders know that they’re building something of insane value. But how do you capture it from the get go? Because if you don’t, you start training your customers to expect more for less. So the big learning for us has been that our Fit is actually probably more pre seed, seed and a and of course, we can follow on in one more round in terms of, like our reserve strategy. But that was a good learning that we are. You know, our expertise is needed much more earlier than what we even thought. Love it
2:08
on today’s special segment, we have David Cohen of TechStars, what’s the biggest mistake or the hardest lesson you’ve learned as an investor, and what’s the story behind that lesson?
2:18
I’ll talk a little bit about liquidity. You know, it’s obviously a hot topic today for LPS, for fund managers, but it’s a hot topic for founders. Also, right that, you know, when’s the right time to sell, or do I partially sell? Or, you know, and I actually think for most of the best investors in the world it it ends up mattering more when you sell almost than what you invest in, right? And so we get very focused on, like the person’s ability to pick, but the money is made or lost in the moments they choose to sell or hold. From my experience, and I think I didn’t really appreciate that until I’d been doing this for 20 years, right? You have those opportunities. And you know, when do you sell an Uber right? How much do you sell? Because there are going to be opportunities. And you know, when you sort of look at that, you say, well, that that could be 100x difference or a really big outcome, right? And that really matters for, you know, your own outcome, and your LPs and your you know, everyone in your world, right? And so there is no magic answer to it, but, but having an approach and sticking to it, right? Like saying to yourself, Okay, when it hits a certain valuation, I’m always going to sell, you know, 20% or whatever, because I want to take the win, you know, get the DPI back to my investors. But even that isn’t always right, you know, because I have about 30 or 35 LP investments in funds, and I’ve worked with managers who didn’t sell, you know, in that moment, and that was a good decision in one case, and the worst decision ever in the other, where it went to literally zero. That does happen, right? Goes from a billion to zero, sometimes much faster than zero to a billion. So I think that’s it is just sort of putting more energy and more focus on that decision making. It makes a huge difference in the outcomes.
4:29
On today’s special segment, we have Victor Orlovsky of our 136 ventures. What is the biggest mistake or hardest lesson you’ve learned as an investor?
4:38
Well, I think that, unfortunately, probably my biggest mistakes I had of me still, so as well as biggest victories, I’m sure so I believe as an investor, I was too Hurry up, especially when I started my career as venture capitalist. I think trying to like get the deal early enough to. Like, keep investing, especially when you raised money like from third parties, keep investing immediately. Is not wise. And sometimes you get pushed by investors. I mean, why you haven’t invested yet? I mean, we have put money, like, three months ago and haven’t been haven’t seen any deal so far, and you are pushed by investors to do deals, but I think that it’s not wise. I think that you have to really wait for your company, right? It’s like, I mean, I’m just thinking of my business to be kind of a smarter business when you sit long and don’t shoot like, as long as you can, don’t shoot like, everything you see you should, like, wait and wait and wait and be sure when you trigger. That’s my mistake. When I’m doing it like, too fast. Sometimes
6:01
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.
