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I crawl out of my car and I call you guys. And I was like, dude, you guys need to come get me. So you took me to a minute clinic.

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The least likely place to resuscitate me. You weren't bleeding. Yeah, yeah, yeah, yeah. I had a massive crippling panic attack. Most people have had them, especially if you're a founder by now. I would learn this later.

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It's when your body is like I can take no more. We're shutting this party down.

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Hello, and welcome to Metacast. And this is your host, Ilya Bezdilov. And with me today is, or actually, I'm with you today in your house. My co-host, Arnab Dekav. We are both in sunny Vancouver today. And our CDO.

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Right there. You can hear probably once in a while. So we are doing a company all hands and offside here in person. Hi, Boomer. He's got a lot to say. Yeah.

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Today we have very special guests. Again, all of our guests are special, but these guys, I discovered accidentally a friend of mine, Prashant, he sent me a message. He's like, dude, check out this episode.

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And it was a startup therapy episode titled Toll Everyone Around the Founder Takes, something like that. It was about the impact on children and spouses and friends and everybody.

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around a startup founder. And the episode was really, really insightful. I think I listened to it two times. I shared it with Arunan right away. Today we have Will and Ryan.

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the host of Startup Therapy podcast and the founders of startups.com. And yeah, welcome to the show, guys. Thanks for having us, guys. Yeah, thanks for having us. Good to be here.

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So can you guys introduce yourself a little bit and maybe tell us what startups.com does? What do we do? Well, yeah, very, very, very many things in the founder space. Let's give a little history lesson to while we're at it. So Will and I have been at this for a long time.

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And we're recording this without Zoom filtration on. You can see that we've been at this for a very long time. I haven't seen myself off Zoom cam in a while. And apparently I have aged. It's not the vitamins I'm taking. It's the Zoom filter. Damn. Yeah, we've been doing this a long time.

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long time. And I don't just mean startups.com. I mean, just like founder space in general, this has been, you know, well, I both long-term founders, but also long-term helpers in the founder space. This is what we love doing. We love talking to other founders, helping them through their problems, reflecting on our own, you know, nothing like holding.

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up the mirror to see what's going on in your world. So, you know, we've consistently built tools, education, community content around the founder space for the last, what are we at? Well, 12, 13 years now.

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Yeah. Getting up there. I was like, how old is my oldest? Because that's a good benchmark. If I could remember that, I'd tell you. Multiply that by dog years. Yeah. Yeah. Is startups.com older than your oldest kid? Just. Okay.

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We both had our oldest kid at the same time. Not together.

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Yeah, not together. Different older kids and not together. Yeah, there are two older kids. Yeah. So we're going back 11 plus years and we've stuck consistently to the North Star, which is we just want to be really helpful to founders and make this amazing.

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journey that can also be really harrowing, really isolating, really stressful, a little less of those things and a little more of the amazing. And I think it's one of the things I keep finding myself repeating to founders a lot lately, which is fall in love with the people you want to serve.

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Fall in love with the population you want to help. Get really, really damn nerdy about their problems and get stuck in all of that.

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And then let the solution flow from there. I run into founders here. They're like, I've got the solution. I'm going to go find a market and people that it'll help. And instead, you know, we've lived that for at least the last, I mean, more than the last 12 years, but in this particular business, the last 11, 12 years, we've absolutely lived that.

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which is we just love founders and our inboxes, our phones, our Twitter threads, all of that will support and justify this. It's all we do. It's all we do. We just talk to founders and it's been great.

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They have no shortage of problems. So it's given us no shortage of businesses to build. Hence, startups.com, fundable, clarity, biz plan, launch rock, all the rest, right? So when you look at the portfolio, all geared towards that.

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I think that's a decent history of what we've done and why. Ryan nailed it on what we do. A little bit of background in the podcast for Startup Therapy. Initially, we're going to do like a lot of people do, a podcast that talks about how to build a startup.

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And we recorded some episodes, some very awkward episodes, I seem to recall, Ryan. Man, so bad. And we were trying to get audio right. We were trying to get topic right. Like, I hated the sound of my voice. Ryan sounds like a radio announcer, so he did not have this problem. Not in my head.

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And so we recorded a bunch of episodes that were like how to build a startup. And they were lame. They were just lame. We talked about the weather. We had it scripted too. We were like, okay, so first be natural, be conversational.

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How is the weather where you are today? It was fantastic. We're listening to this like, damn, this is unlistenable. This is shitty. This is bad. And so I had a bunch of other topics that we were going to play around with.

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And then we started to play around some topics, not about startups, but about founders. And so as you mentioned, startup therapy, had we redone that, it would be called founder therapy.

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It would have been a little more on brand. But that was the genesis. And I think that's important for other people building podcasts that sometimes that initial idea doesn't have to be the idea. I think that's similar to how startups work.

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where everybody thinks they have to have the perfect idea and the perfect pacing out of the gate. And I'm like, no, that's just the seat. So we kind of ran with that. And we did an episode, and my memory serves me, we were about 220, 30 episodes, somewhere in that ballpark. 222 later today, I think.

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If it wasn't the first episode, it was damn near it. We did an episode about how the first $250,000 a founder makes is all the money in the world.

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And it was kind of where we started to really unintentionally debunk these myths, all these bullshit myths about startups, where it's like, oh, you have to make $100 million or nothing.

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No, you don't. It's like, have you actually made $250,000? It's a lot of money. And it's life-changing. And as we started to do that, we started to release those episodes. All of a sudden, we started to get this really

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passionate feedback from people and that's really where we started to say oh damn this is a nerd and it became effortless for us the topics we were talking about

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were things that we had lived personally, the ones that you guys have listened to, when we talked about the toll of all the people around you when you're building a startup, your spouse, your kids, your family, your friends, all of those are real experiences. We're telling you exactly what we went through.

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Ryan and I both had our daughters within, what, the same year, right? Like six months. Yeah, three months apart. Different years, but yeah, it was only because it was in November and a January birthday. Oh, yeah, I mean, time-wise. But literally the year that we started startups.com.

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And that's where we started to learn firsthand the toll it takes. Like, hey, all of a sudden, I've got a kid to come home to. And when we started recording these episodes and covering really personal things, the reaction we got from other founders was like,

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you're in my head. You're literally talking about the things that are in my head right now and that I'm not allowed to talk about in a lot of cases. I'm not allowed to express. So that was the genesis for startup therapy. And you know, a couple hundred episodes in.

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It's not hard to keep finding topics because the moment you talk to another founder, you got another topic. It kind of self-generates. And I think the name is like super apt because that's the feeling I got the first time I was listening. I think it was the...

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Are bootstrapped companies as valuable as venture-backed ones? And I was like, wow, this is exactly what I was thinking about, but also what I wanted to hear at this moment. Just to give some...

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background to our listeners who might not have heard this episode. I guess my biggest takeaway from there was there's actually a very small number of companies that get venture backing every year and an even smaller number of first time.

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venture-backed companies. But I think the total number was 4,000 that you mentioned, and the first time founding is like 1,000. Yeah, that includes second and third rounds, too. Yes.

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But then like if you're in this area, right? So like we were in Big Tech before, so if you're on the West Coast. This is the only thing that you think and see. It's like everyone in your dog gets funding, right? And like if you're not getting funding, like you're nobody, you can't launch a company. Like in this whole kind of indie hacker movement.

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We actually had an episode about this. Indie Hacker Movement is just business. The old school way. Yeah, right. It's just rebranded. It's how people have been doing business like for years. It's just called how most businesses are built historically. Right. Exactly. Yeah.

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So what you guys talking openly about that was really therapeutic in a way because you're like, okay.

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So I just didn't realize that the numbers were so small. Well, that's the thing. You know, I got to say, I might have mentioned this in the episode, but prior to moving back to Columbus, Ohio, where I live now, I actually lived in Beverly Hills, California. And the one thing that always struck me while living there...

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is how these are literally the wealthiest people on the planet, of which I'm not one of them, just to be clear. But these are the wealthiest people on the planet. They can go anywhere they want, and they all choose to come there. It's beautiful in its own right.

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and they've never even heard of venture capital. Think about that for a second. This idea is that the only way you could get to that level is to go the VC track.

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And I'm like, I've never talked to so many people that could not give a shit about technology, venture capital, rich as hell. I'm kind of like, you know, we've got a little bit too much of a bubble situation going on.

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And then you zoom out and you say, hey, if I'm not living literally in San Francisco, like you guys were talking about, and I go to any other town, and I look at the people there that are well-to-do, living amazing lives.

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what percentage of them have ever raised venture capital? And it's going to be like 0.00001%. And yet somehow I'm convinced it's the only way. It's a bullshit narrative.

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Right. So I wonder if that perception is created by all of the venture-backed startups talking about that everywhere. Yeah, absolutely. Of course.

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I mean, it is press worthy. And that seems to amplify, yeah. That's exactly it. I was on the phone yesterday with a journalist who was asking my opinion. And it wasn't to be published. It was just that we were having a conversation with a friend who happens to be a journalist in the startup space.

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Like, so what do you think about the funding crisis? And I was like, it's a really huge problem. It's massive. It's unbelievably big deal for like the 0.5% of companies it applies to.

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That's it, right? And so then we talked about, well, so why does it seem like such a big deal? Because people slowly and carefully and stably building businesses in their homes or a co-working space isn't a news story.

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So it's exactly what you said. The press were the aspect of it. So when we see things in the press, we have to remember they're there for a reason, not because they're important to us, but they're important to getting eyeballs on news stories that pay for advertising that employ people who run newspapers. It's nothing to do with us.

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And coming back to this topic, you didn't go bootstrapping route the very first time, right? So tell us a bit about like, how did you land up in this space? Because right now, I think a lot of what you're talking about is about this topic.

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the last few episodes but initially before startups.com i think you raised the venture funding you ran your startups and all that so tell us like your journey how did you land up on it and what's the path yeah

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Okay, so 30 years ago, I started one of the first web design companies. It's weird to say that, by the way. When you say 30 years ago, I sound like many moons ago, right?

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But that was like circa 94, 93, 94. When marquees on web pages were a thing. Oh, yeah. Oh, no. Actually, it's funny. We hadn't got that far yet.

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That would come later. That would be a massive... I remember when the blink tag was introduced. And minds were blown. We were like, how are we going to leverage this technology? It was incredible. Actually, it's just a fun bookmark at this time.

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At that time, I was a student at The Ohio State University, a theater major actually, had nothing to do with business. And I went to my guidance counselor in arts and sciences to drop out.

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And she was so terrified. She's like, oh my God, what's going wrong? And I'm like, are you kidding? I can't wait to drop out. She's like, what are you talking about? Like, I'm going to start an internet company. And she's like, what's the internet? I figured there was a time, right?

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There was a time. So that's how far back that actually was. It was before people actually had heard of the internet yet. So that said,

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That was a bootstrap company. We were essentially just a design agency. We were building some of the first webpages on the internet. And we grew that really quickly. We grew that to about a $700 million company, bootstrapped, and sold it in 2001.

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Even that was a long time ago. Damn, that was over 20 years ago. Yep, that's a long time ago. You weren't working with each other at that time, though. No.

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We hadn't met you. No, we were working on similar things, which is funny. I mean, sign of the times, I think. Talk about your journey at that time.

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Yeah, I mean, very similar. And just, you know, around the same time that we was building that agency, I was building an agency of my own. It did not get nearly as big. It was also bootstrapped, but we barely left the boots. I think we did buy some shoes with Velcro on them at some point.

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That was kind of as far as we got. But it was such a crazy time. And I mean, I think we can look at some analogs. Crypto brought one of these times around. It did what it did. The internet stuck around in a different way so far. AI is now doing its thing. But it was such a crazy time to be building a company.

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And I think this is probably true for you as well, Will. Venture capital was not on my mind at that time. Raising money was not on my mind at that time. Also, as an 18-year-old in university.

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I probably wouldn't have gone well if I tried, but it wasn't part of the dialogue. Certainly not. I was also at the Ohio State University at the time.

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And it was not part of the zeitgeist. People weren't talking about funding. People weren't talking about investors at that level, right? Investors were old people that sat around pounding tables and talking about the price of copper, as far as I understood. They were not involved in the stuff that I was doing, which was explaining to people like Will was.

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what the hell the internet was, why it was important. My favorite anecdote from that period of time was talking to somebody who was a high level executive at a very large company about the importance of the internet. And he goes, Oh, yeah, hang on, I've got that here in my end.

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gets into a desk drawer and pulls out an AOL floppy. Wasn't even a CD at that point. I'm like, yep, you got it. You totally get it. I thought you were going to say that he would pull a print out of an email or something. If he knew how to print an email, he might have.

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If you saw my agency presentation in 1994, I kid you not, the presentation went like this. In the 1960s, there was something called the DARPAnet.

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which was a defense network. And I had to literally explain how this came to be, right?

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And then my next thing would be, this is called a web page. It goes on something called a web browser, which you use on your computer. You got to understand, people still don't all have computers by this point, right? My secretary has one of those things.

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That's exactly what it was. CEOs would have their secretary come in and show them how to use a computer so that they could use the internet. And these are like majorly paid executives. We had major brands. It was a fun time.

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Yeah, from there, what happened next? What were the next few companies? Basically, your journey up to startups.com.

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Yeah, so I'll give you the condensed version, but after that, in 2001, I started eight more companies. The last three were venture-backed companies, and essentially what I did is I started an incubator, but the ideas were just my ideas.

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I just had a million ideas in a million different industries. We did everything from an online car lease exchange called Swap Elise.

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to online casting for every show on television called GotCast, which is what brought me to Los Angeles, to essentially what Affirm is now, a company called Affordit.

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which was turning retail purchases in 2007 into monthly payments or weekly payments, 10 years ahead of where it should have been.

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And out of that, companies that we own now, like Fundable and BizPlan and what became startups.com, were all generated out of that. The last one I did, the last startup before startups.com,

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was a company called unsubscribe.com, which again, it's so funny when I talk about these things. There was a time where you couldn't unsubscribe from email. People don't remember that, but that actually did exist. And me and a guy named Jamie Siminoff, who started Ring, the doorbell company.

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I started unsubscribed.com. I told them about this ridiculous idea I had on a Sunday morning while eating my chocolate Pop-Tarts that I always had a folder, and I think it was my Yahoo, I'm sure it was my Yahoo, that was called unsubscribe.

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And I said, all I do is as I get junk mail, I move them to the unsubscribed folder. And then I spend my Sunday mornings going through and trying to figure out how to get off all these emails. I was like, imagine if we could automate that. Email is the largest problem there is as far as like total addressable market.

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And he loved it. We raised some money for it and sold it years ago. But that was my last thing. And then startups.com, Ryan and I were very early together 11 years ago. So it's been a minute. It's the longest thing I've ever done.

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Okay. I'm curious with the venture-backed company and bootstrap company. I think the question you asked in one of the...

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episodes is who do you create value for? The question you need to ask yourself. So how was it different when you had a venture-backed company unsubscribed versus with your bootstrap companies? Were there any...

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sort of decisions and situations where you would be like, oh gosh, I wish I didn't take the funding. Or maybe the other way around. The differences are subtle. It's kind of like if you've ever had a steak that's done like perfectly medium rare.

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and you've ever eaten a live earthworm. It's that type of subtlety, right? It's nearly the same thing depending on where you grew up. Yeah, no, I'll let Will go for beer, but I've got my thoughts too. There's more than a few differences.

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Yeah, we've got hundreds of hours on this topic. So here's what was interesting. I think folks will appreciate this. You guys will appreciate this. When I was running unsubscribe.com, affordit.com, gotcast.com, which were all venture-funded companies, I was running them all at the same time. So these weren't like...

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I started them in successive years, but I was running them in parallel. I was also running a few bootstrap companies at the same time, what became BizPlan, what became fundable.com, what became startups.com. So I was kind of running, call it like three bootstrap companies.

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At the same time, I was running three venture-funded companies. Now, what's bizarre about that is that you're basically living like six different lives at the same time. So imagine that this was...

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a version of you as a human. And you had six different versions of your life every day. It's you, but you have a different wife, a different spouse, kids, not kids, you're single, totally different versions of your life all happening at the same time.

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So here's what would happen. We'd call a VC and we'd be like, I've got this amazing new idea. It's called unsubscribe.com, blah, blah, blah. And that VC would be like, that is amazing. I will have a check to you tomorrow. And literally, literal words, right?

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Same call the next day. Different company. I've got this other company called gotcast.com. Not a chance. We have no interest whatsoever. And you're like, dude, I'm the same guy.

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So it was this weird parallel experience, also easily the most unhealthy experience of my life. It's this weird parallel experience where you start to realize that you aren't the only factor.

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The timing, the business, the market, all of these other variables are all things that, frankly, you don't have as much control over as you think. We try to. Like, oh, if I just have the best idea, then it'll just go fine.

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Dude, I had plenty of good ideas, and I ran them all at the same time, and they did not all go the same way. They went dramatically differently. So I want to hear Ryan's take on the bootstrap versus VC side. I'll tell you that...

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having run six lives in parallel, it taught me a lot, which set us up for startups.com.

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I feel like I should probably drop a disclaimer right now around this is not how we recommend running a business and you should not. This is like pharmaceutical level. Like, you know, this could cause these side effects, right? Including weight gain, hair loss, right? Stroke. Yeah. So.

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There are so many differences. I mean, we've touched on various aspects of this across a number of startup therapy episodes. I think the main one for me was that I started to realize that with every decision I made in a company that had investors in the cap table.

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that all of a sudden you had all of these other voices in your head, or at least perspectives that you felt some responsibility for considering and whatever decision got made. Let me give a really simple example here.

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When you go out, you want to figure out what's for dinner. It's just you. You just think about what do I want for dinner? What do I need to do? This sounds good. Tacos sound great. I'm going to go grab tacos. Now, I have a family of five. Well, actually a family of six because my father lives with us.

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When I have to think about what dinner looks like, that decision became infinitely more complicated, right? Ah, we should have tacos. Jack's allergic to shrimp. We should have spaghetti. Hannah doesn't want to eat carbs right now. There's just all of these things that get involved.

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you end up with all of these weird variables thrown into your decision-making matrix that wouldn't have otherwise been there, right? If it was just you making decisions. And Will and I have talked about this a number of times in the podcast, but it's about having that optionality.

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And being able to run the business, not just the way you want to, for the arbitrary sake of being able to say, it's just me, I want to do it my way, right? It's not about that. It's about being able to say, this is what I believe is the critical path right now. I want to follow that.

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And I want to do it this way for these reasons. The second you've got investment dollars in there, the second you're beholden to other people and you've narrowed the allowable outcomes.

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it completely changes your decision-making framework. And so for me, that was always the hardest part when I was like, well, I could do this.

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but that's going to impact the investors this way, or that's going to change the pace to next round of capital, or that's going to impact our ability to hire the way we wanted to, to be able to meet the growth needs.

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All of a sudden, you just got all these other variables thrown into the mix. So for me, that was the heaviest piece. There's a lot of aspects that are really challenging. There's a lot of differences. The amount of stress you go through just to raise the funds.

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cannot be overlooked. That impacts your health, your sanity in the startup. But again, for me, it was about the ongoing lingering effect of just having other decision makers, either actively or just passively, because I couldn't get them out of my head in the matrix.

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If we talk about that, when I was running three companies at the same time that were all venture funded, compared to the bootstrap, the bootstrap companies, you focus solely on your customer, you focus solely on revenue, because that's all that matters. The moment you have investors...

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you focus on them first because they're your lifeblood. And in their whims, in your ability to raise more capital, people don't take this seriously enough, but at which point the money's coming from investors, they are your customer.

00:22:25.104 --> 00:22:33.632
And so all of your decisions and all of your outcomes are based on them. And so you get into this vicious cycle where everything that you do.

00:22:33.632 --> 00:22:45.296
is like, well, how will investors feel about this? And it's a bunch of bullshit because you start doing things where like, oh, if we release this feature that's now AI, investors will be interested in it. And it's like, okay, we would have literally never done that.

00:22:45.296 --> 00:22:57.359
It takes your focus away from like the customers and the product. I can see parallels working to be company where your customer is your manager and their customer is their manager, which is like LPs in the VC case.

00:22:57.359 --> 00:23:10.528
were there any decisions that you made maybe like some examples that you wish you did differently but you did it the way you did because you had investors you know it's weird in the three times that i raised that raised capital for each of those companies

00:23:10.528 --> 00:23:23.615
the seed rounds, the first rounds, they all came together surprisingly quickly. And by the way, that's unusual. And it was also a very unusual time. This is like heading through the financial crisis. It wasn't a great time to be raising capital. And I had never raised capital before.

00:23:23.615 --> 00:23:34.799
My previous companies, I just bootstrapped them all. So I didn't raise capital until I got to my fourth or fifth company. And it just so happened that there was a guy that I knew that ran a venture fund that always wanted to invest in something I was doing.

00:23:34.799 --> 00:23:44.895
And I met with him, told him what I was doing. This was gotcast.com, the online casting company. And he's like, yeah, here's a term sheet for exactly what you want an evaluation that's even good by today's standards.

00:23:44.895 --> 00:23:55.536
And I was like, oh, well, you mean I don't have to use my own money again? I was like, well, that sounds cool. And it is cool. But what I hadn't learned yet, and I would, is that he's now my customer.

00:23:55.536 --> 00:24:08.976
All I care about is serving him. And if I somehow also help my actual customers, bonus. And that really affected me. It took me a long time to understand that. Everybody thinks that it'll change. They think, oh, well, I'll raise some money.

00:24:08.976 --> 00:24:21.200
And then I'll go get customers and it'll be all about customers. That never actually happens. It sounds cool. It never actually happens. So that was a huge lesson through doing both. If you were to like go back, would you?

00:24:21.200 --> 00:24:31.776
try and bootstrap those three companies also? What were the outcomes and how would that have changed it significantly? Sure. So two of them we sold, one of them just faded out.

00:24:31.776 --> 00:24:41.104
And they were both like seed stage fundings, like million, two million, like nothing crazy. Like people do lots and lots of rounds. So the first one was trying to get the order. It was Godcast.

00:24:41.104 --> 00:24:52.960
That one we ended up selling to a private group. That was useless. The second one was afford it. That was probably one of the best business ideas I've ever had. Because again, it was Affirm and Klarna 10 years before Affirm and Klarna.

00:24:52.960 --> 00:25:07.663
But the problem is that it was Affirm and Klarna 10 years before Affirm and Klarna. It was way ahead of its time. Also, right in the middle of the financial crisis. You want a cool time to be raising money for a high-risk consumer finance company? Do it while every bank is melting down.

00:25:07.663 --> 00:25:21.872
It wasn't a popular thread. They're trying to raise for crypto right now. And so by comparison, the money came relatively easy for each of those. When we did unsubscribe, when Jamie and I and my other partner, Josh, did unsubscribe.

00:25:21.872 --> 00:25:35.887
We raised our money in 48 hours. It was unbelievable. I've never seen anything like it. So when I say the raises came easily, with Afford It, we raised the first round relatively easily, but boy, when we went to go do the second round, it was lights out.

00:25:35.887 --> 00:25:49.503
We pitched for a year and a half every single day, three to five VCs a day. I've been to every office on Sand Hill Road and then some. And we had 80 investor meetings, which is a lot. I'm saying...

00:25:49.503 --> 00:26:02.432
80 firms, not just 80 meetings, many meetings per firm. And within those, we had 25 partner pitches. And for those of you that aren't familiar with the significance of a partner pitch, the cadence is simply this.

00:26:02.432 --> 00:26:14.304
You meet with either an associate or usually a low-level person first. They vet you. They then bring you to a single partner. They vet you. And they kind of say to their whole partnership, hey, I think this is a worthy investment.

00:26:14.304 --> 00:26:28.624
Let's have this company come in, pitch the whole partnership. And most VC partnerships say that they have to invest in unison. If one person disagrees, they won't do it. You're lucky if you get a couple of those. That's like the final Shark Tank showdown. We did 25.

00:26:28.624 --> 00:26:43.104
and got eviscerated across the board. We were so toxic for that moment in time. I might as well have been selling credit default swaps that year. Yeah. It was so bad. Iceland was still in the market.

00:26:43.104 --> 00:26:58.064
So anyway, so we got crushed on final fundraise, which is really where that thing died. It was a great business model, though. So while you were doing all that fundraising, what was the company doing? I suppose you were busy, you know, you were on the road all the time. How many people were working? Like, what were they doing? Were you paying them?

00:26:58.064 --> 00:27:09.951
These were early small teams. So these are like five to 10 person teams because you're still only in the seed round. And we weren't thinking in terms of how do we spend as much money as possible. But as Ryan will tell you, I'm very involved.

00:27:09.951 --> 00:27:21.711
At startups.com, I'm writing our copy. I'm doing product management. I'm our CFO. I wear a lot of hats, as does Ryan. Yeah, the way it goes around here. Yeah, there is no management at our company. We're all busy doing shit.

00:27:21.711 --> 00:27:27.311
And so with these companies, I'm not like some figurehead that had the idea and ran off. I'm helping...

00:27:27.311 --> 00:27:40.816
do marketing. I'm helping with writing copy. I'm writing emails. I'm running everything. And I love it. I was probably in the basement of our office running cat five cabling to increase the networking in the sales room, right? Like we got our hands dirty a lot.

00:27:40.816 --> 00:27:55.152
And I think that's one of the challenges is trying to raise, you went through, like you said, every day you had a VC meeting. That takes your focus away from the stuff that your product and your customers need into stuff that...

00:27:55.152 --> 00:27:58.367
You need to raise the next round and the next round.

00:27:58.367 --> 00:28:12.688
It does. Yeah, there's so many distractions involved with fundraising, right? The physical time spent is one of them. Just the fact that you're now emotionally spending energy in other places, right? The yeses are great. The rejections are not. So you're all over the place.

00:28:12.688 --> 00:28:16.336
It's a gambit that you run through and you come out the other end a different person.

00:28:16.336 --> 00:28:29.071
sometimes with money, sometimes without. It's hard to go through that process unscathed. And raising money in 48 hours, to Will's point, very, very unusual and hard to replicate, move. Most people struggle through that period.

00:28:29.071 --> 00:28:37.935
Let's also remind ourselves that most people who set out to raise funding don't actually get there. So there's also all the people who were trying to raise funds and didn't.

00:28:37.935 --> 00:28:46.751
and so think about that so now not only have you faced the distractions the time spent all of that don't have the money and even more sadly now

00:28:46.751 --> 00:29:01.375
you have what's probably a false negative around the viability of your business. Just because investors didn't want to invest in it, now you're going, this thing probably doesn't have legs. This isn't going to work. It's not a good business. It wasn't a good business for them. Go back to the question you asked us at the beginning of this segment, which is,

00:29:01.375 --> 00:29:14.655
Who are we creating value for? Investors look at a business to understand, is it going to make me money? They don't look at it and go, is this a good business? They'll say that. They'll be like, oh, we found a good business last week. What they mean is a business that they think will put money in their pocket.

00:29:14.655 --> 00:29:28.415
Right. Will and I joke about this one all the time. Investors will say things like, oh, it's a lifestyle business. Yeah, no shit. Yeah, of course it is. Right. Of course it's a lifestyle business. Hopefully. Right. I was laughing with somebody the other day. I would say, you know, look, next time somebody hears that.

00:29:28.415 --> 00:29:35.695
they should just high five their co-founder walk out of the room and be like we got all the confirmation we need we don't need their money we can go build a great lifestyle business without them

00:29:35.695 --> 00:29:45.023
yep yeah you were also talking about you know the first 250k being the most important uh money you ever make and i think one of your episodes you said that

00:29:45.023 --> 00:29:59.344
You guys had to do some agency work or contract work while you were building startups.com to fund the business. So can you talk a bit about how you actually do that? Because we might be in a similar situation in a few months, maybe more, I guess, like eight to nine months.

00:29:59.344 --> 00:30:11.327
If you don't make enough revenue from our startup, we don't want to go back to corporate jobs. So you'd rather do some contract work, maybe some education work. Tell us your story, how you did it. How do you find customers? What advice you can give to founders like us?

00:30:11.327 --> 00:30:22.319
Yeah, this is one of my favorite things to talk about. In fact, if you're out building a product, and you can always build a service, if you're thinking, long term, what I need this to be is a piece of software, something that it's going to do.

00:30:22.319 --> 00:30:34.832
whatever, right? Find a way to run that as a service today, because if you can run it as a service proxy, you can start making money right now. Make it something that's an on-ramp for the product later down the road. I think it comes down to

00:30:34.832 --> 00:30:49.215
thinking about what it is you want to build, right? So go back to what I was saying at the beginning of the episode around falling in love with that, the person you want to solve it for. Fall in love with the problems they have. Don't fall in love with your solution. If you think your solution is a piece of software, cool.

00:30:49.215 --> 00:31:00.960
Let's validate the hell out of that and let's make money along the way by running that as a service until we get to the point where it's a viable product. You're also going to build a better product. Ryan's three Ps of great product are proven proprietary process.

00:31:00.960 --> 00:31:12.832
If you can nail that through service, you're going to build a better product. And if you don't, you're going to end up with Ryan's least favorite P in all of product, the pivot. This is where we end up having to now change direction. Why?

00:31:12.832 --> 00:31:23.455
The pivots, you know, this word that we made sound very nice in the startup space, but if you translate, if you look in the dictionary, what it says is built the wrong shit first. That's all it means, right? We just built the wrong thing first.

00:31:23.455 --> 00:31:31.632
I digress, but yes, when we're building out anything, so we looked at our business early on. Will, you'll remember this well. We launched Fundable in 2012.

00:31:31.632 --> 00:31:46.367
We were just we built product. We're sitting around waiting for Obama to sign the Jobs Act into existence. The minute that pen hit the table on C-SPAN, we hit launch and off we went to not much fanfare.

00:31:46.367 --> 00:31:51.728
We had people coming in. Don't get me wrong. There were people like, okay, we can go crowdfund. All right, people showed up.

00:31:51.728 --> 00:32:06.319
It was kind of like opening an innovative new gym that nobody had ever been into before. And they had no idea how to work out on the equipment. They're like, do I hold this above my head? Do I put this on my foot? Why does my back hurt so much? They had no idea what they were doing. And so we quickly realized.

00:32:06.319 --> 00:32:15.359
We needed a service component to what we were doing that would not only augment the product, but would augment our revenue in the short term. And then that went very well very early.

00:32:15.359 --> 00:32:23.296
That turned into a seven-figure line of business very quickly where we were able to really help people to utilize the technology that we just built.

00:32:23.296 --> 00:32:37.711
Oh, interesting. Yeah, I think when you do something that's either B2B or it's like a high check product where you don't have to have like 10 million customers paying you five bucks a month, but you have maybe like a few thousand paying you $500 a month, then I think you can definitely do that.

00:32:37.711 --> 00:32:51.920
thoughts about the consumer product let's say it's an app right we can't provide podcast app as a service to someone it has to be an app so there's a certain point like we have to ship it right what we're trying to do right now is uh i mean what we've done we actually just published a book about starting a podcast so that's kind of it

00:32:51.920 --> 00:33:06.127
We tried to generate revenue through that. But we're also thinking about maybe some additional things, maybe doing some consulting for, I guess, companies of lower caliber than Amazon, maybe teaching product management and, again, software development, these kind of things. But this is not related to the podcasting app that we are working on.

00:33:06.127 --> 00:33:12.256
that would be a distraction just to get the cash flow. Just to extend the runway. Do you know what's more distracting?

00:33:12.256 --> 00:33:25.263
running out of cash and having to shut down your startup okay so put it in the grand scheme of things get the priorities right here guys if the priority is to make the runway extend off to infinity point where like we can just go as long as we want

00:33:25.263 --> 00:33:34.496
There's nothing that's a meaningless distraction, right? As long as you're still getting some time to work on the startup or even no time for a period of time. Will and I joke about this all the time. Startups don't run out of money.

00:33:34.496 --> 00:33:44.175
Startups don't die. They don't need roofs over the head. They don't even need the servers that they exist on because you could offload it and then put it back later. They can just sit and wait for you. The minute you start to have trouble.

00:33:44.175 --> 00:33:57.759
it's a different story. But so something you were saying a second ago is an important point. And I think this is where particularly people who come from a technical background get a little trapped in their own thinking, which is like, at some point, we have to ship it at some point, sure. But you're thinking about

00:33:57.759 --> 00:34:09.152
the technical solution to the problem. If you think about the people that you want to help, go back to what I was saying about just get myopically focused on the population, and then think about the problems they have.

00:34:09.152 --> 00:34:23.952
Then look for the ones that most align with what you want to do. You can usually find overlap there. I'm saying even if you can't, it's cool. If you've got to go drive around on the wrong side of Uber receiving the money, not paying, you have to be on the wrong side of Uber making money to run your startup.

00:34:23.952 --> 00:34:34.719
Okay. But if you can find something that does dovetail into, so if instead of consulting on product, if you could maybe find product companies so you have some relevance and consult on.

00:34:34.719 --> 00:34:45.360
podcasting, for example, or something else, something that's relevant to your market. But you touched on another big one, which is content. So you said we wrote a book. What's the name of the book? It's called The Pragmatic Podcaster.

00:34:45.360 --> 00:34:56.784
I like this. That was not Will and I in the beginning. We're like, how do we make this as technically complicated as possible so that we'll never want to keep one of our episodes? We got over it finally. We were less than pragmatic.

00:34:56.784 --> 00:35:10.655
So you can simply start with content. You can start with community has become a really big thing and people are more and more inclined to pay for access to communities to get answers to the questions they have. Again, like if you know there's somebody out there running a community.

00:35:10.655 --> 00:35:25.184
who cares all day long about you, who cares all day long about the problems that you suffer from, where better to hang out to forward your journey. And so sometimes that means aiming a little bit upper funnel, going kind of earlier stage people who maybe aren't exactly.

00:35:25.184 --> 00:35:36.000
the fit user for your final product. But guess what you're doing the entire time? You're helping to move along that chunk of the population to get them closer and closer so you can act as an on-ramp for your own product.

00:35:36.000 --> 00:35:49.119
Doesn't always work out that way, but these are the explorations I'm always going through as I'm thinking about our own businesses. I'm thinking about how to help other founders, which we do all day, every day. This is the calculus that's playing out in my head. How can we build a good on-ramp that works for us now?

00:35:49.119 --> 00:35:56.000
keeps us moving in the startup and helps to age our population towards utility within whatever the product we want to build at some point is.

00:35:56.000 --> 00:36:09.840
So I'm curious how you guys came up to the startups.com idea because you were just talking about communities, right? And startups.com is about communities. So yeah, what's the origin story of that? How did you just decide like, okay, so this is what we're going to do.

00:36:09.840 --> 00:36:23.807
I was just thinking about this. Ryan, you'll appreciate this. The origin story was me having a heart attack. Like literal heart attack? Pretty much. My heart's stopping. So in the early, early days, I was still running those five plus companies.

00:36:23.807 --> 00:36:37.711
And one of those was going to become fundable. We were kind of developing that. And BizPlan harder existed, et cetera. And Ryan and myself and a couple other people were at lunch together. And I remember telling you, Ryan, I was like, dude, I don't feel right.

00:36:37.711 --> 00:36:41.072
I was 37 years old. My daughter had just been born.

00:36:41.072 --> 00:36:55.199
We had just moved back to Columbus again. We've done this back and forth a couple times. We just moved back from Columbus. We had been running five companies. We had been growing companies, failing companies, like doing everything you possibly can. I had like every life event you could possibly have at exactly the same time. Let's just put it that way.

00:36:55.199 --> 00:37:05.472
getting married, whatever. So anyway, I'm like, hey man, I don't feel right. I go, I hop in my car, and I was going to drive home. And Ryan, you remember, I only lived five minutes from the office. I didn't make it.

00:37:05.472 --> 00:37:14.255
And I'm cruising up the street. I hop on my phone. I call my wife. And I'm like, babe, I don't feel right. And as soon as I said that, almost like on command, my heart stopped.

00:37:14.255 --> 00:37:26.128
By the way, you can't not notice when your heart stops. That's not something where it's like, oh, that feels kind of weird. No, you're kind of dead. And also, the whole body goes limp. By the way, I'm behind the wheel of my car on a highway. Also not a great time.

00:37:26.128 --> 00:37:40.351
I end up coming to, regaining control of the car, and because I'm an idiot, I drive home. I crawl out of my car. Ryan, this always reminds me of Wolf of Wall Street when he's crawling out of his car. And I'm like, I crawl into my living room, and I call you guys.

00:37:40.351 --> 00:37:46.815
I think I called you. And I was like, dude, you guys need to come get me. And because you guys are idiots, you took me to a minute clinic.

00:37:46.815 --> 00:38:01.199
the least likely place to resuscitate me. You weren't bleeding. Yeah, yeah, yeah, yeah. And they put me on the EKG and whatever. They're like, dude, you need to go to the hospital. Like right now, what are you even doing here? And so next thing I know.

00:38:01.199 --> 00:38:12.143
I'm in the emergency room. Short version of it, and I think this is important to folks listening, I had a massive crippling panic attack, which I had never had before in my life. While this was happening or after?

00:38:12.143 --> 00:38:25.711
That's what the heart attack was. That's what the precipitating, yeah. Oh, okay. It was the panic attack. Yeah, it was my heart seizing for long enough for things to not be cool. And when people think panic attack, if you're not, most people have had them, especially if you're a founder by now. I would learn this later.

00:38:25.711 --> 00:38:39.311
But if you haven't had them before, you don't think much of it. Oh, I guess he was just nervous. No, it's when your body is like, I can take no more. There's just nothing left. We're shutting this party down. Anyway, the reason I tell you that story.

00:38:39.311 --> 00:38:53.871
is because at that moment, that was the game changer for me, where I was like, okay, I can't just go do this again. I can't reset. And my wife was like, you're doing all of these things, all these companies, whatever.

00:38:53.871 --> 00:39:05.519
because you can, meaning you're willing to put the time and the effort into it, not because you should. And truer words were never spoken, right? So I ended up taking some time and be like, what do I want to do here?

00:39:05.519 --> 00:39:19.456
a couple of things really resonated with me. And Ryan and I have talked about this stuff at length on our Startup Therapy podcast. One of those was, what don't I ever want to do again? Again, when people are thinking about what's the business idea, et cetera, they think it's just about the business. It's about your life.

00:39:19.456 --> 00:39:33.440
and how you want to live it next. Because this is supposed to be setting you up for the life that you want. And that should be part of the DNA of this company. It's not just about, do we have a cool business idea? And so I tried to think of all the things that I'd want it to be.

00:39:33.440 --> 00:39:44.096
And then something struck me because it was hard to do. Why don't I list all the things I don't want it to be? And Ryan, do you remember when we were sitting in the conference room, we started to list these things?

00:39:44.096 --> 00:39:57.472
You can still see. Number three, don't work with assholes. Exactly, exactly. It was literally written on the board. I probably have a screen cap somewhere, but it was on the board. I know that sounds obvious. Of course I wouldn't want to work with assholes. Try doing it.

00:39:57.472 --> 00:40:08.016
Tried doing it and raising money, by the way. Good luck with that. And so we started to list all these things that we never wanted to do again. For example,

00:40:08.016 --> 00:40:16.831
We never wanted our company to prevent us from being able to spend time with our family. Not that we don't have to work, we have to work. One of those things were like 12 years later I meet my kid.

00:40:16.831 --> 00:40:28.063
Not like that. And no lack of founders have had to make those sacrifices. And that's definitely where I was headed. Ryan, that may have been where you were headed. Elliot, our other partner, that's definitely where he was headed.

00:40:28.063 --> 00:40:39.023
Startups.com wasn't just about there's a market opportunity, which I'm going to explain in a second. It was about we need to change our lives permanently. And it took us every bit of 11 years to get here.

00:40:39.023 --> 00:40:53.648
It didn't just start magically where I guess we don't work with people we don't like and I guess we get to do what we want. I guess we get to see it. Every day we were like, is what we're doing working toward that goal? If so, it's good. If not, raising capital, bad. Now, we always give this disclaimer, by the way.

00:40:53.648 --> 00:41:00.224
We spent a lot of time on this podcast kind of knocking investors. You know we run a fundraising platform for investors.

00:41:00.224 --> 00:41:13.983
This isn't some anti-stat. If you go to your website, startups.com, I think that's one of the more front and center things you will see as like a call out. If you want to do this, join here.

00:41:13.983 --> 00:41:28.351
Yeah, yeah, yeah. But here was the other part of it. Ryan talked to this a moment ago. He mentioned the, you know, love your customer. I know personally, I sat around and I said, if I could do anything on a Saturday, this was the exercise. If I could do anything on a Saturday, unlimited amounts of money.

00:41:28.351 --> 00:41:38.559
and I could spend my time any way I wanted to spend it. How would I spend it? And then how do I make that my job? Turns out, here's how I spend my Saturdays, sitting around bullshitting with founders.

00:41:38.559 --> 00:41:50.608
Most of my friends are founders not because of startups.com. They were founders before startups.com. And I find them to be just naturally the most interesting people in my life. You don't meet many disinterested founders.

00:41:50.608 --> 00:42:04.112
The one cool thing about founders is no one's disinterested in their job. So anyway, so I started to think about it and I'm like, how am I spending my time with these founders? What am I talking to them about? Like, how is that part of kind of who I am or what I care about? And it turned out.

00:42:04.112 --> 00:42:10.335
that if I could have a job, and I know Ryan feels the same way, would we just sit around and bullshit with founders all day?

00:42:10.335 --> 00:42:23.423
is somehow get paid for it. We don't even know how, it actually doesn't even matter how we get paid for it. But if that's actually what we do every day, exactly having this conversation that the group of us are having right now, and that's our job, dude, whatever it has to be.

00:42:23.423 --> 00:42:37.615
And it turned out that was our North Star. Our North Star is how do we just sit around helping founders all day? It didn't start with what's the market opportunity, what's the product, or anything else like that. Our problem statement at startups.com.

00:42:37.615 --> 00:42:47.760
became this simple. There are 40 million startups started every year worldwide. Zero of them know what they're doing. That's our problem statement. No one knows what they're doing.

00:42:47.760 --> 00:43:01.952
Because of that, we're like, anything we could do to help on this journey with funding, with customer acquisition, with mentorship, with peer networking, is going to be a net positive. And over time, it changes, like the form factor of how we need to help startups is going to change.

00:43:01.952 --> 00:43:15.664
I don't care. Because so long as I'm sitting around bullshitting with founders all day, I'm gold. That was the journey. Yeah, we seem to keep inventing new problems at record pace. So there's no shortage of work to be done. It was such an amazing realization to know that.

00:43:15.664 --> 00:43:27.967
There were these things that we had experienced in our own founder journeys, some of which were absolutely amazing and some of which were not, right? Like having to stuff Will into the back of a car. I have to go back to that story for a second. There was this hysterical moment.

00:43:27.967 --> 00:43:39.231
where, because we had laid him out across the back seat horizontally, Elliot on one side, I on the other, we both started to buckle him in. Elliot was buckling in his feet and I was buckling his horse and we looked up at each other and we're like,

00:43:39.231 --> 00:43:54.159
I guess that's what we do. I don't know. There were a lot of things that when you look at the founder journey, there's so many common experiences. And a lot of them are wonderful, but a lot of them are not. And while there were tons of people out there...

00:43:54.159 --> 00:44:07.791
teaching you how to be really good at being a founder, how to be good at growing your business, there weren't enough voices out there telling you how not to do it. Basically, like, here's how to be good at product. Here's how to be good at marketing. Here's how to be good at this. What about here's how not to be bad at your health?

00:44:07.791 --> 00:44:16.815
here's how not to be bad at your relationships here's how not to be bad right and we saw that this was actually when you came down and started to check the balance on most founders

00:44:16.815 --> 00:44:29.568
That there was so much weight on both sides of the fulcrum in terms of things that they were doing well and things that they weren't. And that it wasn't that hard to shift that balance. There were just so many more things they were doing. They had all these opposing forces in their founder lives.

00:44:29.568 --> 00:44:43.648
And that just became something that we really wanted to impact, not just to make you a better at building a business, which that's cool too, right? We wanted to build great businesses, but not at the expense of their personal relationship, not at the expense of their health, not at the expense of their emotional health.

00:44:43.648 --> 00:44:58.000
i think that became again just going back to this whole notion of when you really really love your customer when you really love the person that you want to help everything becomes easy now in our cases we also had personal experience because we were also our own customers right so we were also fixing the problem of not needing to go pick willow

00:44:58.000 --> 00:45:01.599
by the roadside, stuff him into a car and take him to a minute clinic and hope everything was going to be okay.

00:45:01.599 --> 00:45:15.887
It worked out, but could have gone the other way and we wouldn't be on this podcast right now. Well, at least Will wouldn't. Yeah. I'm available. So it's such a fun story to go back through and think about how we got here. And I mean, it goes all the way back, you know, for both of us.

00:45:15.887 --> 00:45:30.096
starting businesses really young, facing all those challenges, not having the type of support that we wanted. And at a time where you just couldn't even go out and find it either. Like at least now you go read a blog post about it. Not that that's a great answer to a lot of these existential questions that we face, but it was better than like, you know.

00:45:30.096 --> 00:45:36.559
like, oh, I'm having an existential crisis as a founder. Let me go to the library. Look in the Dewey Decimal System. There's a book on accounting.

00:45:36.559 --> 00:45:46.688
Maybe that will help me feel better about all this. Starting your small business. Imprint 1975. Sweet. Exactly. That'll help. So a big part of this was just us wanting to build the treehouse we didn't have as kids.

00:45:46.688 --> 00:46:01.311
So it was like, what are all the resources? What's the support? What are the things that we didn't have that we would want to be able to pass on to the next generation? Which is getting easier to say, by the way, well, now that there actually is kind of like a next generation to startup founders, we're seeing people who were born after we graduated university.

00:46:01.311 --> 00:46:15.599
Yeah, amazing. Bizarre. I remember I had 2018 or 2019. So I was a manager. I had an intern. And this girl was... I did the math. I'm like, she could have been legally in my...

00:46:15.599 --> 00:46:30.351
daughter. And I'm like, okay. And I was maybe like 36, 37, but she was very young. She was like 17, 18 probably. The first for me was we were at lunch and we had some same thing. Somebody super young coming right out of college.

00:46:30.351 --> 00:46:37.376
And she was like, oh my god, I can't believe it. My dad is turning 40. I have to get him something for his birthday.

00:46:37.376 --> 00:46:50.016
And I'm like, whoa, I'm older than your dad. I was like, that's some next level stuff. And after that, I was like, yep, I'm that guy now.

00:46:50.016 --> 00:46:53.248
from this point on but yeah it's a lot to digest

00:46:53.248 --> 00:47:07.760
So like more than a decade later now, how's the startups.com, like how's the company structured? How many people do you have? Who does the engineering work? So there's a couple of things I think that are pretty unique. And Ryan, I'd love to hear your perspective of it.

00:47:07.760 --> 00:47:21.456
So we've got about 200 folks on staff. And we've been a self-sufficient, debt-free, profitable company for a pretty long time now, at least five, six, seven years. And because of that, we are very, very financially disciplined.

00:47:21.456 --> 00:47:34.992
Again, I'm our CFO. I am in the books every single day, 24-7, around every decision. And it prevents us from doing a lot of things. I think it's part of things that people don't talk about. They're like, oh, I guess you guys are successful and you have lots of people. No!

00:47:35.056 --> 00:47:47.920
You'd be shocked at how granular these decisions that we can't make are. And here's why. We don't have a pot of money that we don't know what to do with. Every single free cash flow, a dollar, has 10 different places it can go.

00:47:47.920 --> 00:48:01.840
from staffing to marketing to you name it. And so for any time with us, all of our days are spent trying to stack rank what's going to get the next dollar. Because it's one thing, always at the expense of 10 others. And when new folks come on board...

00:48:01.840 --> 00:48:11.744
And they're like, hey, can we do this and this and this? We're like, no, we can't. We actually can't. We are very disciplined and limited. And when we get over our skis, and we do from time to time.

00:48:11.744 --> 00:48:26.623
where expenses are starting to outpace revenue a bit, we have to make hard decisions. We have to cut staff in some cases. Fortunately, knock on wood, haven't had to do a lot of that this year, but who knows? But we're not immune to it. Real stuff happens, and the economy's down. It's down across the board.

00:48:26.623 --> 00:48:41.327
We have six different products and they've all faced some sort of attrition or hit over the past 18 months. Almost impossible not to. So in running this business, we have to respond to that really quickly. Now, if you have a whole bunch of cash in the bank...

00:48:41.327 --> 00:48:56.304
like a lot of my friends do or did. They used to. You can do things differently. You can say, hey, let's even keep hiring going even though it looks like some macro trends aren't working because we want to be able to work through this and there'll be more capital on the other side. Except there wasn't.

00:48:56.304 --> 00:49:05.376
and now everybody's getting cleared out. Right. So we want to talk about your podcast a bit. I think we will soon start running out of time. So your podcast is

00:49:05.376 --> 00:49:19.311
Amazing. Thank you. Since I discovered that episode, I've been binging on it. I also like that your episodes are fairly short. I think it's like 30 to 45 minutes usually. Actually, I did find myself, like I went on a walk, I started listening to your episode. It was that Woodstrap versus VC backed company episode.

00:49:19.311 --> 00:49:25.360
And well, guess what? I made my walk twice longer because I wanted to finish the episode. You're welcome.

00:49:25.360 --> 00:49:36.416
NPR calls this a driveway moment when you come to your garage and you wait for your podcast to finish. You don't go back home, right? I love it. I love that. That was my sort of driveway moment, yeah.

00:49:36.416 --> 00:49:46.976
Hey, how old are you? I'm 39. I'll be 40 this year. Ah, okay. Artem, how about you? I'm 42. Okay, well, then you guys missed the cup. There's an episode called The Curse of the 37-Year-Old Founder.

00:49:46.976 --> 00:49:57.824
which was essentially the story that I told you guys. And I was hoping you weren't going to say 37. There's this weird thing, and I don't know why it's a thing, where everyone seems to have this crushing life moment.

00:49:57.824 --> 00:50:09.407
at 37 as founders. A lot of it has to do with life stage and things like that. If you guys ever get a chance to go back to it, it's both a cautionary tale and probably one of the realest moments that you'll be able to relate to as an adult.

00:50:09.407 --> 00:50:23.168
Yeah, I think before we actually go into the podcast, I think both of us probably faced a bit of that midlife crisis, I guess that's what it is, right? But we were both in corporate jobs and we were just high paid, you know, all the status and brands and all that. But it's like, you're just...

00:50:23.168 --> 00:50:26.751
Can't keep doing this. At some point, you got to do it for you. What are you living for?

00:50:26.751 --> 00:50:38.815
Yeah. It took a few years, but I think we finally figured out how to like untangle all of that. Now it's the next phase is how to keep doing this for a long time. Yeah. And it's a long-term investment. Like a lot of times.

00:50:38.815 --> 00:50:51.088
You know, Ryan, you and I work with people all the time. They're like, you know, I want to get into the startup game. I want this thing to be self-sufficient within the next couple years. Of course. Totally agree. It just doesn't actually work like that. You know, what you think is only going to take like a year or two.

00:50:51.088 --> 00:51:04.655
takes three or four or five years if you're lucky, if it works, and then takes 10 years to really build the thing that you actually thought would take three. And that's fine, by the way. It's just a long period of uncertainty and grind, and that's a lot for people to get through.

00:51:04.655 --> 00:51:06.864
Yeah. Maybe it's...

00:51:06.864 --> 00:51:21.135
it can be compared to raising a child. So it's not like you're getting a baby born and you're like, okay, so I wish, I wish, you know, he got 18, like in two years, right? It does take time. Yeah. Then the minute they get to 18, you wish they would go back again. So be careful what you wish.

00:51:21.135 --> 00:51:29.072
for yeah there are definitely times that we've been through this you know there were there were times I think every business goes through these life cycles where there are periods of like

00:51:29.072 --> 00:51:43.344
pure joy and excitement and build and chase and it's all adrenaline and then you get to these points where like it becomes a little more operational and it's that's kind of like now your kid's 14 or 15 and they don't need you in the same way that they did and you show up with the toys and the games

00:51:43.344 --> 00:51:48.320
like, we don't want to play like that anymore. That's not how this business works now. And you're like, yeah.

00:51:48.320 --> 00:52:02.639
And I think that's one of the fortunate things in our case, we've been able to reinvent the business so many times to keep it fun and exciting. I think the most recent version of that would have been, well, the podcast was one of those things. So to look back to the podcast, the podcast breathed life back into both of us where it was like it gave us.

00:52:02.639 --> 00:52:13.487
this new, amazing outlet that was not just creative, but cathartic. And then we were seeing the reflection from the community, how much it was helping people. Those things feel amazing and kind of bring youth back into it.

00:52:13.487 --> 00:52:23.952
and then our founders group accelerator product which as you build product as you build software as you build platform you get further and further and further away from your user base

00:52:23.952 --> 00:52:36.960
in a real sense, because there's these abstracted layers of value between you and the people you want to help. So bringing that back down to a very human product, in addition to all of the scaled software and education tools that we have was amazing.

00:52:36.960 --> 00:52:51.679
That was a rebirth for all of us where we'd rolled up sleeves back into one-on-one or one-to-many conversations with founders that completely changed how we interact with that customer base that we love so much. It just brought us back to the fold. It made us a ton of new friends.

00:52:51.679 --> 00:53:02.992
When you spend a whole bunch of time with a founder, often at their darkest moments, and they're mostly dark moments, let's call it what it is, and you're the guiding light that kind of guides them out of that, that's a big deal. It's a great way to build a relationship.

00:53:02.992 --> 00:53:11.391
So I don't know if you guys are able to share any numbers in terms of like how many listens you get and kind of what role does the podcast play?

00:53:11.391 --> 00:53:18.512
in the whole kind of overall marketing story. I know it's therapeutic for both of you, but from the business side of things, what's that impact of the podcast?

00:53:18.512 --> 00:53:28.304
It's been interesting and it's been much higher than we would have expected. When you look at the relative numbers, it doesn't compare to some of the things that we do in terms of overall reach.

00:53:28.304 --> 00:53:35.327
The depth of the reach is incredible. We've realized that there's something that there's around a 40%.

00:53:35.327 --> 00:53:47.088
coincidence rate with people who have joined our accelerator and people who were podcast listeners. It wasn't necessarily the podcast that pushed them into it. But when you talk to people who've listened to the podcast.

00:53:47.088 --> 00:53:59.856
And a lot of them have binge listened to like, we get these emails all the time or reviews or whatever, where it's like, I binge listened to the entire series in a week. And I'm like, I'm not even sure they must've listened to it on two speed. I'm not sure that's even possible. I think there's more hours in a week. Anyways.

00:53:59.856 --> 00:54:03.280
And so what ends up happening is this relationship forms.

00:54:03.280 --> 00:54:15.248
And I think this is an important point here because I don't think that will always be true with any podcast, right? I think because of the deeply personal nature, because of the deeply emotional stuff that we're talking about, the existential crisis.

00:54:15.248 --> 00:54:20.335
it brings people close to us in a way that a how-to podcast wouldn't.

00:54:20.335 --> 00:54:32.735
And so I think that there's something really interesting about that. And so in our particular case with the podcast that we have, the audience we have and the way we've chosen to deliver it and stuck to it because we've been given lots of advice. This is the other thing. We could have had more reach with this podcast.

00:54:32.735 --> 00:54:46.047
If we had taken on guests, we could have had more reach for this podcast if we decided to maniacally run around the country and get on everybody else's podcast. But we said that wasn't exactly what we were about. And we've stuck to the guns. And again, the scale.

00:54:46.047 --> 00:55:00.880
not massive, but the impact has been huge because of this coincidence rate with the people that the trust relationship that it builds. It's been something absolutely magical where people feel like they know us. Here's the other thing that's been cool. Well, I'm sure you've experienced this as well. You get on the phone with somebody.

00:55:00.880 --> 00:55:14.367
who you know has spent 200 hours hearing some of your deepest, darkest thoughts and moments, you don't have to play warm up with that person. You're like, I know you know me and I know enough about you given that you spent 200 hours listening to me.

00:55:14.367 --> 00:55:27.423
we can just jump right in. And so like these bonds happen really, really quickly. It's been incredible. I think maybe a way I could summarize that, Ryan, is to say the podcast doesn't bring us customers, it brings us friends. 100%.

00:55:27.423 --> 00:55:41.807
Yeah, great. I can definitely relate to that experience. We recently talked to someone who listened to us from the very first episode, sort of our superfan. He's probably listening to us right now. And in the very beginning of the meeting, so yeah, we met with him and he's like, it feels awkward because I was like, I know so much about you guys and you know nothing about it.

00:55:41.807 --> 00:55:52.463
Right. You know, in the early, early stages, we were probably maybe 20 episodes in. We had done an episode about how a founder is incredibly lonely.

00:55:52.463 --> 00:55:59.615
Because nobody relates to us. We can rarely go to our spouse and tell them what's actually on our mind because there's consequence there.

00:55:59.615 --> 00:56:12.047
They make, oh wait, we're running out of money or like, oh my God, like you're whatever. We often can't go to our co-founder because they're like, wait, you're second guessing whether you want to do this. You can't talk to people at cocktail parties because they're like, what do you do again?

00:56:12.047 --> 00:56:24.864
They don't care. Yeah. At all. 30 years later, my family still thinks I do something, quote, in computers. Yep. That's how connected they are of all the things that I've done for 30 years. No idea what I do, which is fine.

00:56:24.864 --> 00:56:39.648
So we get this really long email from a listener. This is one of the first ones that really struck me. And he said, I was doing a cross-country trip with my fiance. And we started to binge listen to your podcast while in the car. And she said at some point, she looks over.

00:56:39.648 --> 00:56:51.887
And I'm completely in tears. And she's like, are you okay? He's like, this is everything I've been trying to tell you for like the past year. This is exactly how I feel. And I was like, damn.

00:56:51.887 --> 00:57:04.079
As good as our pop-up ads might be on a landing page, nothing evokes that kind of response. You want me to join your mailing list? My God, that speaks to me, right? Night and day, this is not...

00:57:04.079 --> 00:57:19.007
comparable to like customer acquisition whatsoever. You've built a friendship and there's nothing like it. Right. I love the style, free-flowing, natural conversation, but also the topics are, like you said, they're a therapeutic to like listen to.

00:57:19.007 --> 00:57:30.335
So you mentioned that you tried out some guest episodes and had some horrible experiences. Tell us a bit about that. So the first one was Steve Blank. I don't know that Steve knew we were on the podcast.

00:57:30.335 --> 00:57:44.751
Do you remember that? I do. And it's so funny because it was one of those situations where we got the email. We'd love to have... We got an email from... I think maybe the first one was from Steve, but then it quickly turned into talk to my people. Who's Steve, by the way? Just to give some...

00:57:44.751 --> 00:57:57.824
So customer discovery. The guy is an absolute expert. If you want to understand customer discovery, Steve Blankster guy, right? And a very well-known entrepreneur. He's done a lot of things, but probably best known for customer discovery.

00:57:57.824 --> 00:58:12.112
We get the email back saying, you know, OK, talk to my people. OK, so we talk to his people and we give the ethos of the show the fact, you know, this isn't a how to. We don't want to talk customer discovery with Steve. We want to talk about his journey as a founder, where the ups and downs.

00:58:12.112 --> 00:58:18.288
were all these things and I think we had some topic I don't remember what the topic was we're like this is what we're going to focus on and what we got instead was

00:58:18.288 --> 00:58:32.559
Will and I sitting in stunned silence while we got a 30 minute breakdown of customer discovery process. Well, that didn't work as we had hoped or intended or even encouraged. And when it was done, I was like, I actually don't want to publish this episode.

00:58:32.559 --> 00:58:47.168
Like I feel like an a-hole because we have a massive amount of respect for Steve, but it had nothing to do with our podcast whatsoever. And so we tried a few others. Do you guys know who Sam Parr is? He has a My First Million podcast. Yeah. And this was long before that. Sam was doing a business called The Hustle.

00:58:47.168 --> 00:58:57.920
and Sam's been a friend for a long time, and I had Sam on, and Sam ironically started basically doing the My First Million podcast, basically what he wanted to do on the episode.

00:58:57.920 --> 00:59:08.416
This is before his podcast. And he's like interviewing me and asking me how much money I have and all these. And I'm like, what happened? This doesn't make any sense.

00:59:08.416 --> 00:59:19.360
And so we had good guests, and it did not take us long. We only had like three or four, right, Ryan? We had good, good guests, but we realized it wasn't the format. It made no sense.

00:59:19.360 --> 00:59:30.992
There's a whole thing where you have to have guests in order to increase your distribution because ideally they'll share what you do. Totally get it. Totally get it. It just made for a shitty show. So we're stuck on our own fame, which is very, very minimal.

00:59:30.992 --> 00:59:41.215
It was an interesting exploration to go through, right? And I think that if you were to look at those, if anybody else listened to those episodes, I don't think they'd be like, this was a horrible podcast, but it wasn't startup therapy.

00:59:41.215 --> 00:59:49.007
We had done enough episodes, and I'm so glad that we didn't try that early on, Will, because I think it may have completely changed the trajectory. We might have been like, well, this is what the podcast is.

00:59:49.007 --> 01:00:03.824
If we had just stuck with a guest show where we were just interviewing entrepreneurs, I know it wouldn't have had the impact. Nobody would be crying over an interview that we did with Steve Blank, right? We would be. We did. We had to have two episodes after that just to talk about how to not do guests anymore. Yeah, yeah.

01:00:03.824 --> 01:00:13.135
But I think it was an important realization to have and to figure out, again, to Will's point really early on in this episode, what do you not want to do? And sometimes what we say no to...

01:00:13.135 --> 01:00:25.615
is so important to what the final outcome is. Because by saying no to guests, what we said was yes to a deeper conversation between he and I, and yes to being able to provide that value to our audience. And that's super important.

01:00:25.615 --> 01:00:37.487
So I think that for anybody listening who's planning a podcast, starting and trying to building towards that, one of the things to really keep in mind is how are we going to add that specific value to our customer? Don't try to do everything for them.

01:00:37.487 --> 01:00:49.887
Think about who that listener is. What do they need to hear most from me? What's my unique perspective? What is the thing that I bring to the table? They're not going to get from somewhere else, right? Because we could have done them. Here's how to market your startup podcast and join.

01:00:49.887 --> 01:00:59.472
70 or 80 others. We could have done any number of things, but what we chose to do was the thing that we felt like was very underrepresented and would bring a high level of value to the population.

01:00:59.472 --> 01:01:05.456
And if you're doing it right, it's a lot less effort. Podcasts are hard work, but if you're doing it right, it's because you want to be doing it.

01:01:05.456 --> 01:01:19.103
By the way, this podcast here generated two new podcast episodes for us. Here's two new podcasts you're going to see. They came from you guys in this episode. I wrote these down. One's going to be cold when the investor becomes your customer. I think that's going to be a great one to cover.

01:01:19.103 --> 01:01:21.152
I noted that one mentally. Yep.

01:01:21.152 --> 01:01:35.440
I don't have the title here, but the long period of uncertainty and grind, like how long is that exactly? When you say like, hey, Will, it's going to take many years before this thing becomes profitable or self-sustaining. Can you be more specific? Tell me exactly what you mean, because I'm in it and I'd like to know when it's going to be.

01:01:35.440 --> 01:01:48.304
to be over and kind of go through what those milestones are in the different phases. But this is what I'm talking about. We just sit around and bullshit with founders all day and we're like, oh man, that's a really interesting topic. Let's talk about that. Hadn't thought about that one yet. Cool.

01:01:48.304 --> 01:01:58.112
All right. So we are approaching time. And so we wanted to ask you, I guess, a couple of parting questions, very quick ones. What podcasts do you listen to?

01:01:58.112 --> 01:02:05.152
too personally because we've been talking to a lot of podcast listeners recently and that's the primary way people discover podcasts so yeah recommend something to our listeners

01:02:05.152 --> 01:02:17.231
So I found one that I've been listening to a bit recently called Hard Fork. I'm enjoying that one. Yeah, so that's been good. I always get this one wrong. Is it The Verge Report? I'm trying to remember the name of the podcast. The Vergecast?

01:02:17.231 --> 01:02:30.351
The problem is there's The Verge, there's The Verge Cast, there's The Verge Report. I'm going to have to go back and find out what that one is. I can send it to you guys afterwards. I'll have to remember exactly which one it is. Those are good. It's interesting. Right now, I'm actually not listening to a ton of other podcasts. I really enjoy ours.

01:02:30.351 --> 01:02:43.791
There are a few that I'll pick up. When I hit podcasts now, it's mostly to completely unwind or check out. So it's been things like Smartless or what's the one? Fly on the Wall with Dana Carvey.

01:02:43.791 --> 01:02:56.480
Oh, geez. I'm doing a great job of sharing podcasts today, aren't I? They're clearly very emotional to you. Very, very deep. No, they're not. Like these are the things like I listen to them as I go to sleep at night and I fall asleep to these just like lighthearted stuff. It's what I need right now.

01:02:56.480 --> 01:03:05.487
But no, I mean, hard fork, I completely agree. Like I love that podcast. Yeah, it's good. I think it's going to become required listening in my household for my entire family.

01:03:05.487 --> 01:03:18.976
I don't listen to any podcasts. I mean, as funny as it sounds, like the only one I ever listened to, Ryan, you and I talked about this, I'll listen to our podcast. And here's what's so funny about this. This isn't being narcissistic. Whenever we record a podcast, as soon as we hit stop,

01:03:18.976 --> 01:03:33.056
I have no idea what I just said. I go into some weird hole or whatever, and so I'm not kidding. Every time when the podcast actually releases, or I listen to my car, and I'm never in my car, this is why, and I'll put our podcast on.

01:03:33.056 --> 01:03:46.271
I'll start listening. Damn, that's a really good point. And then I realized I'm the one making it. Totally forgot. Yep. I used to listen to it because I was trying to figure out how we could get better, right? How our pacing could get better in whatever.

01:03:46.271 --> 01:04:00.175
But now I listen to it because I haven't actually heard the episode. I'm actually hearing it for the first time and I'm like, wow, we actually were poignant on our point or like, man, we rambled for a while. But since I'm never in my car because I work from home and I don't go anywhere.

01:04:00.175 --> 01:04:12.128
I'm never in a place to podcast or listen to podcasts. I don't listen when I'm working out because I listen to music. I don't listen when I'm in my workshop. I'm a huge carpenter, so I do a ton of them also because I'm listening to music. So I just don't have a venue for it.

01:04:12.128 --> 01:04:25.760
But if I ever start becoming running guy or something like that, I'll be all over the podcast. If you ever become running guy, there'll be more interesting things to talk about. Does somebody else do post-production for you? Or you guys produce your podcast yourself? We outsource it.

01:04:25.760 --> 01:04:33.248
Yeah, we did that for about a hot minute. And then I realized I don't want to be an audio engineer when I grow up. And so we cut that out really quick.

01:04:33.248 --> 01:04:45.711
For us, Ilya does it, but he loves doing that stuff too. Oh, wonderful. If you need more hobby to occupy yourself, we can send you ours. No problem. Free of charge. He may run out of cash, maybe. Yeah, yeah, yeah. There's that side hustle.

01:04:45.711 --> 01:05:00.079
All right. Actually, yeah, that might be a good idea. All right. Well, guys, thanks a lot for your time today. I really appreciate it. And this will come out next week. We publish on Wednesdays at 3 or 3 a.m. Eastern time. You guys get up earlier than we do.

01:05:00.079 --> 01:05:08.384
I'll be awake and ready to go. All right, Arnab. This was an awesome episode. One and a half hours just gone, right? Yeah. Didn't even realize how fast it went.

01:05:08.384 --> 01:05:16.143
Yeah, we actually had to let Will and Ryan go because we were just at time. So we are recording this just by ourselves. Yeah.

01:05:16.143 --> 01:05:30.447
So one thing we wanted to announce, which we'll talk more about in the next episode. So we finally published the book. It's called The Pragmatic Podcaster, a step-by-step guide to starting an amazing podcast. So that's what the book is about. It's about how...

01:05:30.447 --> 01:05:40.496
You actually follow things step by step, starting from figuring out what your podcast is about, who is it for, what the persona. Basically, we take the product management approach to starting a podcast.

01:05:40.496 --> 01:05:50.255
And then going into how they record, what software you use, what microphone you buy, how you get guests, how you write a cold email is one of that, right? Yeah. How you produce your episode.

01:05:50.255 --> 01:06:03.824
and then how you improve over time. And the reason why I picked that name, the Pragmatic Podcaster, it's obviously homage to the Pragmatic Programmer book. The idea here is that being pragmatic means that you don't do things that...

01:06:03.824 --> 01:06:13.295
are not needed. You do like the 20% you need to get 80% done. And then some things you can just do later. Improve later, little by little, yeah.

01:06:13.295 --> 01:06:27.599
Being pragmatic means being incremental in many ways, right? And running a podcast, starting a podcast could feel really overwhelming, especially if you do it all yourself. And overwhelmed, you will not be with my book. So that's like you.

01:06:27.599 --> 01:06:35.775
Yoda. Yeah. I mean, I watched like 10 Star Wars movies. Yeah, right before coming. Yeah. So where can people get that book?

01:06:35.775 --> 01:06:50.096
pragmaticpodcaster.com. And that is on Gumroad right now. So you can get like a EPUB version, PDF version of it. Yeah, you can get the PDF version. I'm still working on the EPUB version. It turned out to be more difficult than I thought. Hopefully by the time we record the next...

01:06:50.096 --> 01:07:04.304
episode we actually will have it on amazon because i just don't know that this kindle create software which is a piece of shit but you get what you get to do to get on amazon and you can also get to the book by going to our website metacastpodcast.com

01:07:04.304 --> 01:07:14.960
There is a book link up there now. So yeah, find it there. Tell us how it's going. Send us any feedback you have. You can reach us at hello at metacastpodcast.com.

01:07:14.960 --> 01:07:26.896
Yeah, and you can get a 30% discount on the book if you use the code Metacast. Yeah. Just type Metacast, you get 30% off. It will be active for a week after this episode comes out. Right.

01:07:26.896 --> 01:07:41.327
Cool. Awesome. And you can always reach out to us at hello at metacastpodcast.com. We would love to hear back from you like you just heard from Ryan and Will. Those long emails, you know, if you made me cry, tell us about it.

01:07:41.327 --> 01:07:53.807
We would love to hear those stories. I really resonate with that kind of deep connection because that's how I feel about podcasts. And we've received a few and they have been amazingly wonderful. Yeah. Yes, yes, absolutely.

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Thank you for listening. Yeah, but you also can support us by finding a t-shirt. We have some pretty cool Metacast t-shirts on our merch store at merch.metacastpodcast.com. We have a few there. Minor podcasting celebrity.

01:08:08.431 --> 01:08:09.552
is my favorite one.

01:08:09.552 --> 01:08:23.823
Yeah, that's the one I got to. It still hasn't arrived yet. Maybe because I'm in Canada. That's an anti-ad. Yeah, but in the US, I got it in less than a week. Within a couple of days. Not a couple of days, because they actually, they print on demand, right? So you order, then they print it.

01:08:23.823 --> 01:08:36.239
and they ship it. It was probably five business days or so. Yeah, not bad. Not bad at all. All right. And then with that, we'll talk to you next week. Bye-bye. Bye.