A Product Market Fit Show | Startup Podcast for Founders
00:11:14 · Damien Lewke, Pablo Srugo
[00:11:14] S0: Yeah. [00:11:15] S2: How do you make the decision, which is always the key moment of, do you just kind of cold turkey it? Okay, I'm going all in, screw it, or you kind of phase it in. How do you play that out going from employee to founder? [00:11:25] S0: Yeah, great question. So ultimately I can only speak from my experience, but I definitely ascribe to the cold turkey school of thought. So, you know, my decision point basically is I got really quiet with myself and asked myself, if I made $0 and all I could do was tackle this problem. Would I do it, right? If I could accept that I would get no monetary benefit, but I could focus on this problem full time. Would I do it? And the answer was yes, that's when I made the jump. The best advice I can give to a prospective founder is be obsessed with the problem and not inherently your solution. Because your solution will evolve and change over time. If you're calling all the shots a couple of years in, you might want to ask yourself why that's the case. But for me, it was the obsession with the problem and just going, you know what, I got to do this. And thankfully, I made the jump and I'm very grateful that I did. It is a moment of uncertainty. It can be a bit scary when you got forty bucks in your bank account. You're like, oh, gosh, I hope this works. But it has been by far the most rewarding experience.
00:12:27 · Pablo Srugo, Damien Lewke
[00:12:27] S2: But I would argue for somebody in your position who's doing something in their industry. Worst case scenario, a year later, it doesn't work. You're probably extremely hireable. You've got that kind of the downside protection. Which is different than if you go, and this is the good thing about going into your industry. When you decide like, oh, screw it, I'm gonna start a marketplace for whatever, right? And then you try to come back. It's a little tougher. [00:12:47] S0: It certainly is. I will say this for what it's worth as a hiring manager. I actually am always excited to meet founder curious people or former founders. We have a former founder on staff here. You are also extremely hireable if you try something and it doesn't necessarily work out. Because the problem solving and skill sets that you build and learn, honestly, you know, there's that expression, right? We learn far more from failure than we do from success. To me, that says a lot about your character. So it's definitely something that I totally get but yes, you're right.
00:12:47 · Damien Lewke, Pablo Srugo
[00:12:47] S0: It certainly is. I will say this for what it's worth as a hiring manager. I actually am always excited to meet founder curious people or former founders. We have a former founder on staff here. You are also extremely hireable if you try something and it doesn't necessarily work out. Because the problem solving and skill sets that you build and learn, honestly, you know, there's that expression, right? We learn far more from failure than we do from success. To me, that says a lot about your character. So it's definitely something that I totally get but yes, you're right. [00:13:15] S2: I mean, I tend to agree. It always depends on the employer. You know, the bigger company or a small, but for a startup. I can tell you for our companies, the first ten, twenty hires, if they could be all founders, I'd probably be for it, right? We just try, and it's just because the level of management a founder needs, frankly, is zero and so somebody gone out for a year or two years, and done something on their own. It's like, okay, I know I can be like, this is the thing you're doing, and they're just going to go run off and do, which is amazing. [00:13:36] S0: Yeah, a hundred percent, right? And early days, you have to have that kind of flexibility, right? You're wearing a million different hats. There's no structure. Having somebody who can just take something and run with it is invaluable to a startup. [00:13:47] S2: So, we're going through the story. So you've decided that you're going to leave. Are you alone? Do you have a co founder at the outset? What's the setup?
00:13:47 · Pablo Srugo, Damien Lewke
[00:13:47] S2: So, we're going through the story. So you've decided that you're going to leave. Are you alone? Do you have a co founder at the outset? What's the setup? [00:13:47] S0: First time solo founder. So it was just me. [00:13:47] S2: Oh buddy, going on hard mode, I like that. [00:13:58] S0: Yeah, I have conviction, I had conviction and you know, at the time it was the right choice. And I backed that up. [00:13:58] S2: And you're technical, so you could build the stuff and try to sell it? You could do both those things? [00:13:58] S0: Yes, so again, fortunate in that regard where being technical I have the ability to kind of sit across both. But one of the core functions as we built this company is I've continuously hired myself out of a job, right? Hired myself out of the marketing leader role and we've got an amazing head of engineering, product, sales, customer success. That's been my constant focus, right? It's ultimately to bring people who are more skilled and more accomplished in each of these roles to develop that. But yeah, in the beginning, I sat across everything. Which was interesting.
00:14:38 · Pablo Srugo
[00:14:38] S2: I mean, I love that and I actually want to take a tangent on this. Because it's more and more popular that, I mean, solo founders have always been a thing but I think with AI, there's just a rise. Statistically, there's just more and more solo founders. And especially, I would assume that a lot of that increase is actually from the non technical who before, could not start a startup without a technical co founder. Now they're like, wait a second, I could actually build a product. I could deploy something on my own. The question I have is, how have you, specifically, because there's different, you know, people play things different. I'm curious on how you did it. The fact is you therefore start with more equity, which is great. But you have more gaps, more holes to fill. If you're three co founders in theory, I'm like, I'm the salesperson, I'm the product person, I'm the CEO. Whatever it is, right? And so you're like, okay, cool, we don't need to hire VP sales, we don't need to hire VP. Did you therefore hire heads of earlier? Did you give them bigger equity grants than they would have gone into another startup that has two or three co founders? How did that end up playing out for you?
00:15:31 · Damien Lewke
[00:15:31] S0: Yeah, you know, I've always focused on needs based hiring. I think that's another thing too is when you're especially early, you need to be pretty litigious about capital management. But yeah, I mean, my focus was to give folks who are coming in. Because it's earlier and it's riskier, compelling offers, right? To me, I've always believed, and my team knows this. Compensate the folks well. I think one well placed person is far better than four poorly placed people and that's why I think one of the most overlooked but valuable skill sets for a founder is to run an extremely diligent and focused recruitment process. Because you want to be certain. Because when you're six people, that seventh person is, you know, fifteen percent of your business. You want to make sure that you're doing the right thing.