Why Working for Second Time Founders Works Better..

Adam Liebman, VP of Sales at Steno and angel investor, explains why working for or backing repeat founders beats first-timers. Execution matters more than ideas. Ryan Shank rented a SoHo studio on Peerspace in hours to start this podcast, proving action creates luck.
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I mean, that's the— it's like the whole thing about investing, right? It's the power law. You only have to be right once. And one thing I learned from all the angel investments, and even maybe more so as an employee, uh, working for a non-first-time founder is a huge advantage.
Here's Adam Liebman, prolific tech sales leader, angel investor, and friend.
And friend. Yeah. Uh, we have, we have a good story. Adam Liebman, uh, currently the VP of Sales at Steno, which I think we will definitely not plug, but we help lawyers find court reporters for depositions. Very fun stuff. That is— wow. Uh, I think, I think we'll probably have more fun talking about the trip I took for Steno recently down to Nashville. But great to be here. A Podcast. Am I a guest? Am I a future co-host? Is this a thing? We don't know. We don't know. See how this goes today.
We're gonna see how it goes. Leave a comment, uh, if you like what you see. I know we're gonna be flooded with comments. So like, subscribe, download, definitely, definitely get in early, definitely get in early with the, with the, uh, the comments there. But look, one thing I do want to, want to highlight is that, uh, that life rewards action. And, uh, I just, I mean, even a quick story about booking this podcast. We, uh, I went on Peerspace, which is a website where you can find studios to, to book in, uh, in New York and other cities, and I saw this backdrop here and I was like, this space looks awesome. It's in SoHo, it's like $150 for an hour to rent the studio. And I just, you know, went through the motions and, and rented the studio and I was like, oh, this is cool. And then it, it kind of transfers from being like an idea to this is happening. It's real. And, you know, I want to highlight like it's not just coming up with ideas and then not taking action. Everyone has ideas. I feel like I've talked to 100 people that are like, I thought of Uber. It's like, Okay.
Yeah.
Okay. Sally from like Memphis, which I love. Memphis is a cool city too. It's a great city, but it's like life rewards action and then, you know, creativity creates energy that creates action and then just things happen. So like, you know, that saying you create your own luck. And, and one final thing, most people that I've noticed kind of have a fear of failing, so then they don't actually start. But I actually have a fear of not failing. Because that means I didn't put myself in a position to fail. Means I didn't act.
Yeah, it's true. You know, listen, we're both founders. I had a failed startup. I remember when I was at Single Platform, Dave Tisch actually came in and he gave a talk to the sales team. And I don't remember what the context for this statement was, but he was like, ideas are shit, execution is everything. And it's like, you can have the idea for Uber, you can have the idea for anything. And we all kind of know what we have to do if we want to put something into action. But the tough part is going and doing it. So listen, did I think that on Saturday I was going to be here in a podcast studio recording with you? Absolutely not. But man, this is fun and we'll see what happens.
Yeah, no, this, this studio is awesome. Speaking of that, speaking of failures, I, I forget who it was, but they were like, here's everything I've done. And it's like a list of things. It's like failure, failure, failure, win, failure, failure, failure. It's like if you can bat 200. Yep, you could be a multi-billionaire.
I mean, that's the— it's like the whole thing about investing, right? It's the power law. You only have to be right once. And one thing I learned from all the angel investments, and even maybe more so as an employee, uh, working for a non-first-time founder is a huge advantage. Investing in a non-first-time founder is a huge advantage. I know for Squad which is the failed dating app startup that I, that I had back in 2015, um, I would do roughly 1 million things different if I started that company today. But I didn't know all that stuff, and I had to kind of fail and learn those things on my own. And I think, um, you know, you have to like just go and do it and see what happens. You only have to be right once. First 2-hour warm-up to Share Willow.
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