EPISODE

Saas Companies that Anyone Can Start with Rob Walling

Jan 11, 2022·80:00·Sam & Shaan·with Rob Walling, Ben·Listen·AppleSpotify
0:0040:0080:00
14 moments · 315 paragraphs · synced to the second

There's a lot of online communities. Anyone can start one. You get a few hundred people together. There are so few people who not only run in-person events, but who do them well. And if you can do that, it is an incredible competitive advantage.

SAM

Okay. Uh, Sean's not here. What are we going to talk about? Uh, a few things. Oh, let me tell you something. Sorry, I asked you a question and then I interrupted you, but let me tell you something. So I'm doing something cool in 10 days. So on the pod and on Twitter, I talked about how I'm buying a piece of property and I'm turning it into like a thing, like a, like a hotel, Airbnb fitness thing. I had this guy, I'm not going to say who it is yet because I haven't asked his permission. But basically he bought, uh, like 5,000 acres in the South, in a, in a state in the South, let's say Georgia. And he is turning it into an airline hotel or an airline neighborhood soon with hotels. So basically they're putting an airstrip in the middle of this piece of property and then they're lining up houses along it. So, uh, you could buy a house and then soon it's going to be a hotel and then they're going to have an airplane hangar there. So for all airplane enthusiasts, you can keep your plane there and take off and land on this, you know, right outside your home. So it's basically like having a, a, a house on a golf course, except instead of a golf course, it's an airplane runway and hangar. But here's the kicker. He asked me if I wanted to come check it out and I said, yeah, sure. He goes, all right, meet me at the Teterboro Airport in New— like outside of New York on, you know, January 25th and we'll fly my jet down. Um, so I'm flying private down. I'm gonna go up to New York just to fly back down, just like it creates it. But nice, isn't that— isn't that sick?

BEN

So is this, um, is it like super rural or is it, uh, kind of just outside of a major metropolitan area?

SAM

It's an hour and a half outside of a major area.

BEN

Got it. So, and most of these people, most of these houses, is this gonna be these people's like full-time residents, you think?

SAM

No, no, probably not. It's a lot of like older people. You don't have to be, you don't have to be like rich, rich to do this. I think you have to like be able to afford a $200,000 plane or something like that. That could be your hobby. So you have to have some money, but it's not like gonna be necessarily like incredibly wealthy people. Yeah.

BEN

So enough to afford like a Cessna or something like that. And you can just fly in and it's just somewhere to fly and then you stay by your airport and just hang out and chill.

SAM

Yeah, that's kind of neat, right?

BEN

Yeah, it is kind of cool. How much do you think he's in on this project?

SAM

Um, uh, I'll, I'll say it. And then if he says I can't, but, uh, nearly 8 figures is the money that he's had to use his own money to do that. And then he'll, uh, raise some more money.

BEN

And then how many houses?

SAM

And he was like, he was like, oh, it's just like a side project. And I was like, what? That is huge.

BEN

That is, uh, how rich is your friend? What does this represent for him?

SAM

I don't know. I just met him. Um, I'm not like wealthy enough to be able to afford that, but not wealthy enough to like, I like, if he loses that, it's not, it's like, will be really bad.

BEN

Do you own any like vacation homes or secondary homes or anything like that?

SAM

Well, no, no. I own, um, my house that I live in. I own, and then I own some, uh, uh, like rentals and like, uh, now a vacant lot that I'm building a house on to sell.

BEN

But nothing like this. No plain vacation home.

SAM

No, no, I don't own— I don't— I think that vacation homes only make sense for me personally, only makes sense to me if I buy them and rent them out. And so if I can find a place in New York or California that I like, and I could rent it out and make a profit, then I would do it. So I met this guy the other day who was a billionaire or close to a billionaire. And this person has a an apartment. They don't live in New York, but they have an apartment there and it's really fancy. And then they have a place in Park City and they rent it out when, when they're not there and it pays for itself. And they're still like, it's like a wealthy person. I think that's the way to go is you, but not everyone's comfortable doing that.

BEN

It's interesting to me, cuz this idea that you're describing sounds like the inverse of what I would want. Like, I want to be able to fly places so that I could stay there. Like I wanna fly to New York so I can go to New York. But this is the opposite. They're setting up somewhere to stay so that they can fly.

Does that make sense?

SAM

Well, it's not just that. Just imagine you're like 65 years old and like you want to like spend the weekend at this area and you want to fly there and stay there and hang out and then go on trips throughout the day and just hang out with a bunch of other airplane nerds that are like you. Yeah, sure. So it's like if you're like 65 and this is your passion, I think, I think that people who are into this shit are so into it that they just want to be around other people who are into it.

BEN

Yeah, I think there are a lot of opportunities like this as people— as more and more people— because it looks— sounds like this is mostly retirees, but I think you could also do it towards remote workers of just like— people have lived places for no particular reason in the past, and I think as people can now choose where they want to live, they're going to start congregating more in groups of like I don't know, group around their hobbies or like vegans, how they want to eat. I don't know, like random niches.

SAM

I agree. I think that will happen too. The day that New York allows short-term rentals— so in New York, you're not allowed to rent for under 30 days, um, or you gotta like jump through crazy hoops. But the day that that's allowed, I'll be buying a place there.

Huh.

SAM

But not, not until that's allowed. Oh, okay. You want to talk about this, uh, Elizabeth Holmes thing?

BEN

Yes, I do. Uh, so you, you sent this to me. Well, you want to give the backstory?

SAM

Well, let's say what happened yesterday.

BEN

So, uh, yesterday you sent a post to me and Sean that you were on the front page of Hacker News.

SAM

Yes, they had— go ahead. I meant like what happened to Holmes yesterday.

BEN

Oh, so Elizabeth Holmes, uh, convicted of like 3 or 4 crimes. Um, I don't know if she's been sentenced yet, but she could serve— she will serve years of of hard time.

SAM

Potentially up to 20 years.

Yes.

BEN

Well, there's 3 counts that were— carry sentences up to 20 years and one that carries up to 5. So I don't know if those are additive or if it's only up to 20. I don't know how that works.

SAM

But yeah. So yeah. And what happened yesterday, it actually happened on Sunday night. I got a text from a friend who goes, hey, you're on the front page of Hacker News. If you don't go to Hacker News, it's basically like Reddit, but like, if I said Reddit for nerds, you would be shocked because Reddit is for nerds, but this is like really for nerds, like nerd nerds. And it's all like computer nerds. And of which I am one of them. And I, uh, I got a text saying that my article that I wrote in 2015, it was on the front page of Reddit or on Hacker News. And it was getting it, which means you'll get millions of visitors. And the headline to my article was. The coverage of Theranos is utter bullshit. And I wrote this article defending Theranos, Theranos, and defending Elizabeth Holmes, and it did not age well, that article. But let me explain what the article— do you have the article in front of you? Yes.

BEN

I just want to talk about my favorite, like, subheadline, which is you called it a minor PR hiccup.

SAM

Yeah. So I call this a minor PR hiccup. So I wrote this into— so I was like 24, I think, or 25 when I wrote this. So whatever, you know, I've grown and I read my writing. I was like, oh my God, I wasn't bad then, but I'm way better now. And so I was a little embarrassed. But the article basically was written after people accused Holmes of at first doing something wrong and they were hating on her. But previously, in the, in the previous month, in the previous few years, she was on the COVID of all these same magazines. And the point of my article was on the, on the, on the surface, it looked like I was defending her and I was defending her. But what I really was also doing, and I say this in the article, is I was defending this idea that like it's— I think it's nonsense and crazy that we build these people up and say that they're like the next, you know, the next Steve Jobs or whatever it is. And we like want small businesses to win and someone starts a business and we want them to win. But then once they get really successful or potentially like, uh, they're considered like a winner, we turn on them and we just hate them just because they're doing something like that seems really weird and they talk funny or they look funny. And I thought that's bullshit. So I stand by that second half because now that's even the whole anti-tech thing is even bigger. But yeah, I was wrong. I, I was so wrong about her. Yeah.

BEN

It's just, you see so many cases of a lot of these hit pieces that are totally not fair to founders that like your guard was up enough that you didn't see that this was the time that they were actually right.

SAM

She fooled me, man. She fooled me.

BEN

She fucked you in with her deep voice and those big eyes, dude.

SAM

She got me. I was so on board. The reason, here's why I was on board with it. And the reason why I was on board with it. Is really a— I can't decide if it's a good reason or a bad reason, and you tell me. So their biggest backer was Tim Draper. I don't know Tim, but I used to be friends with his son, and his friend's son Billy is an awesome dude. And from what I've read about Tim, Tim seems amazing. I know that he's like this, like, high-integrity, very honest person. He seems like a great guy. He don't party, don't drink, and he's known for like being one of the first investors in SpaceX, I believe first investor in Hotmail. So a bunch of these like really amazing companies that helped found the internet and create the internet and everything. And he was super on board with Theranos for a long time. And so I was thinking, well, there's no way that Tim Draper would do something, um, or like would be tricked by this because he obviously didn't know, but he's like, there's no way that Tim would be tricked by this. And that's why I was like on board.

Yeah.

BEN

And just to back you up, uh, just reading from the article, it's expected that a young company that's attempting to change a massive and archaic industry will mess up. It appears that Theranos made a bunch of mistakes and I'm not defending their actions. I'm also not saying that the media shouldn't point out the truths about Theranos's mistakes. You just go on to say, talk about how the cycle kind of flipped on them. So, yeah, I mean, it is true what you're saying, but it is still funny to have an article up with that headline.

SAM

And I didn't delete it on purpose. So around 3 years ago, someone made fun of me for that article and I was like, I'm not deleting that. Well, keep it up. It's all right. I got it wrong. If I'm gonna, if I'm gonna take swings, I gotta let people see the misses too.

BEN

Yeah, absolutely.

SAM

Um, all right. Wanna go to one more topic?

BEN

Yeah, we got 4 minutes.

SAM

So, all right. So you tweeted out something that was pretty cool. What was it?

BEN

Okay. So it was essentially, we started a new family tradition in my family this year, which is, well, and it was just my wife and I doing it because We, we, we started— we're going to try and roll out to my siblings and my parents.

SAM

But didn't she make a presentation? Yes.

BEN

So what it is is that I decided it was kind of my idea that at the end of the year we're going to make presentations about how the past year went and essentially what our goals are for the coming year and our resolutions and that type of stuff. And we're going to present it at like a family board meeting. It could be a slide deck, it could be like a memo, but it's essentially called the board meeting. Family board is sitting there and you have to present on your year.

SAM

It looked like she was presenting to a bunch of people.

BEN

Yeah, it was just you.

It was—

BEN

yeah, it's just me.

SAM

Oh my God. And—

BEN

but okay, so— and I should say, we're not totally crazy. Like, we did it kind of funny, all right? I dressed up as Steve Jobs. I put on the black mock neck, gold glasses.

SAM

Um, I'm not criticizing you. I think it's cool. No, I know.

BEN

I just don't want you to get the wrong idea that we were like getting hardcore, going over our numbers. Like a lot of it was, was kind of funny, was played for chuckles, but it was a good opportunity to just reflect on what we'd done and, uh, and what we hope to do this year and, and, uh, and go over it.

SAM

So what was the, uh, was that effective?

BEN

Yeah. I mean, some of the stuff, so let me read some of this stuff actually. Um, me and Sam, I do the same, I do the same thing. So My wife actually collects the stats, uh, and your wife's pretty alpha, right? Yeah, she graduated from, uh, a top law school in the country and then worked for Georgetown. Uh, pretty fancy. Yeah, it's good. It's good law school. And then she works for a big law firm now. So she took stats. She like tracks all her mother stuff, because we had a baby last November. Um, and so I couldn't believe some of the stuff. So like gallons of milk that her body produced in 2021, 350.

SAM

Gross! Isn't that crazy?

How does a—

SAM

how does a body do that? That is crazy.

BEN

I know, that's— that blew my mind.

SAM

350 gallons, so much.

BEN

It's so much.

SAM

So you're— that's hilarious. You're You track how much milk your wife made?

BEN

Yeah, she also kept track of how many nights she slept on the floor in our daughter's room, because like sometimes she wouldn't sleep. And so 104 nights, almost a third of the year. Yeah, she slept on the floor in Claire's room. Um, no, the number of hours she spent nursing her was 1,800. Um, and then we tracked—

SAM

wait, 1,800 in one year? Yeah. Wow, man, being a woman is so much harder.

BEN

I know that, that did help me realize like, wow, that's just like, that's another job in addition to your job.

SAM

Like, holy moly, that's crazy. What else?

BEN

Uh, any other stuff? Yeah. Um, she counted the number of times my daughter was obsessed with this book, Monsters Come Out Tonight, which is Halloween book. She read it 62 times.

SAM

Why does she do all this, your wife? Just because she wants to show your kids?

BEN

I don't know. She's just compulsive, actually. She is the type of person where in the morning she'll go, do you know what today is? And I never know because she always knows weird anniversaries in her head. She's like, oh, it's 10 months since this happened. I'm like, how do you know that? But she compulsively tracks little numbers in her head. So she apparently tracks them on her phone, too.

SAM

Dude, your wife's Rain Man. That's sick. She's like a lactating Rain Man. That's lovely.

BEN

I might have to delete that.

SAM

I don't know. I don't know.

BEN

I'll have to think hard before I decide whether to publish an episode in which we call her a lactating Rain Man.

SAM

Um, that's cool.

BEN

So what do you mean as a compliment though? Right?

SAM

You mean as a compliment? Yeah. Well, it's neither a compliment. Well, the Rain Man is, the lactating thing is just fact. Um, the Rain Man thing is definitely a compliment. Um, do, uh, do, do you, is she care, is she earning more than you as you start your business? Yes. That's pretty sick, right?

BEN

It's nice. I don't mind it.

SAM

You, uh, is she paying for everything?

BEN

Um, no. So she's actually still net negative because she just graduated in, um, whatever, in the summer and didn't start school until October. Um, so I— my goal is for us to never have a year where she earns more than me, not for any like sexist reasons. I just, you know, it's a gold mine, so I got to make more money than her this year. But yeah, in the last quarter of last year, she made more money than me.

SAM

So, all right. And that's actually like, I think there's a lot of guys who are self-conscious about that. I, uh, feel the opposite. I'm like, I want you, like, I want to be the lazier of the, like, I want her to earn more and just maybe like not have to work.

BEN

I am self-conscious about it. I, I do, like, I'm happy for her to have a career, but like, it's not so much of like, uh, self-conscious about her making money, but it is like a little bit of like a step it up. You gotta get your business into a place where you're out-earning me. Like, look what I'm out here doing, you know?

SAM

That's sick though. It's pretty sick. I think, you know how like there's articles that talk about like your best financial decision? My opinion is the best financial decision you can make. Of course, this is a good decision for a lot of other reasons. But the best financial decision is marrying the right woman.

BEN

Amen.

SAM

Or picking the right spouse, rather.

Or just staying married, right? Did you have— you're the millionaire next door where they're like, no, what did they say? They look at all these factors that like most millionaires have, and this is not Silicon Valley millionaires. It's like auctioneers and construction company owners. And they say like, here are all these factors, like most have never purchased a suit for more than I think it's like $800. Most have never paid more than $200 for a watch. Most, and the vast, vast majority of them never got divorced.

SAM

Don't get divorced then.

That's great.

SAM

Crazy. And I think even if you get a prenup, I don't think that that like, it, it doesn't, does a prenup only work for the earnings that you made before you got married? Yes. So then who cares in most cases?

Exactly. Cause you get married. I got married at 25. I was worth jack shit. Right. And it's like all the money that I've made in my life has been since I've got married. I've been married 21 years.

SAM

So. Does a prenup cover if you start a business and it's worth nothing and then you get married and 10 years later it's worth a lot? Does that— is this— which one does that count as?

That I do not know. What I do know is a friend of mine got married, got a prenup, and he had crypto and he specified like this, my hundreds of Bitcoin are excluded and they've gone up in values and they're still excluded. But I don't know if company shares act the same way. I would guess they would, but you know, we'd have to get a lawyer on here. Why are we, why are we covering this? It's like the worst sad topic.

SAM

No, here's why we're covering it. Because, um, Ben's, Ben quit his job to start a podcast, uh, a popular, uh, a podcast that's going pretty well. And he works for us part-time as a producer. And he, his wife is a very successful lawyer. And I asked him, I said, you know, like a lot of men might be self-conscious about that. About your wife earning significantly more than you, how does it make you feel? And, uh, I was just curious.

BEN

Has your wife ever earned more than you, Rob?

Ooh, that's a good question.

SAM

Um, well, your businesses are like family businesses, kind of, right?

Yeah. I mean, she runs her own thing, dude. I actually think, I mean, yeah. So when I left Drip 2 years ago, I sold a company and then I left it in 2018. I didn't work for 6 months, but it's like, so I wasn't earning anything. But then even after that, like starting TinySeed, I didn't take a paycheck for a year. And she was making several hundred grand at her business. So yes, she has, but it's also like, yeah, but I sold a company. I think I'm excused at this point.

SAM

You know, I, uh, my wife became a millionaire, a liquid millionaire before I did.

That's awesome.

SAM

Because by 2 months, was it like stock or what would you have? She worked at Airbnb for a long time and then it went public in December and I sold my company in February. So she beat me by 2 months.

You didn't feel, you didn't feel bad about that at all, did you?

SAM

Dude, I was pumped for her. I was so— I mean, the way that everything is ours. So it was like, frankly, when she got paid, I was like, oh, I just got paid too. I mean, I thought it was awesome. We're live now, by the way, Rob. Oh, great. Are you okay with that?

Absolutely, sir.

SAM

I'm always—

I'm always— I was born ready. Yeah.

SAM

So this is Rob Walling. Rob, you— you— I was just on your pod like 2 weeks ago. Did it go well?

Yeah. Well, I got a lot of positive feedback actually. What was interesting is someone said, a couple people said, you guys have real great rapport. And I said, which is funny because we've never met. It's not like we're best friends, but they said you sounded like you were friends. You're naturals, you know? And I said, I think it's easy to have a podcaster on a show because they're just entertaining naturally.

SAM

And I've been reading your work for like 10 years. Um, and so, or I forget how long, but basically Ben, we, so this is Ben, Ben works with us. Um, he's filling in for Sean today. We, uh, I sent Rob like an email, like in 2000, and I forget, he like pulled it up, but I sent like my first email to him like years ago saying how much I loved his content. And then I was finally on his podcast like 8 years later.

So it worked out. Yeah. And that helps. That familiarity certainly helps. I know that people who listen to my podcast and then appear on it know what to expect and they're able to, to roll with it, which is why before coming on here, I, I, I've listened to your show on and off over the years, but like, I listened to like the last 4 episodes just so I would have some familiarity.

SAM

What did you think?

I think they're great. You got a great show here. I think you should change the name of the show is what I think you should. I think the name's off.

SAM

The name is horrible.

I know it's tough. And man, I have, you know, my podcast is Startups for the Rest of Us, which I still like, but it feels long now. And I've debated whether to change it. Have you guys actually considered it? Cause I'm curious what would go, what would need to go into a name change?

SAM

The problem is. Is we considered it like a year ago when we were smaller, but then we were like, back then we were like, oh, we're too big. Back when we did that, we were at like 300,000 or 400,000 uniques a month and, or visitor or, um, listeners a month. And we were like, oh, but we're too big. It already is stuck. Now we just, in December we crossed 2 million, uh, listens a month. And we're like, now we're definitely too, like, we're definitely too big. And Dharmesh, who is the founder of HubSpot, who now owns the podcast, He was like, you got to change the name. And I'm like, Dharmesh, it's way too late. And he was like, no, it's not. And so he thinks we should do it. I think it's too late in the game. Frankly, I think a bad name sometimes is a good— is a good thing. But the name is quite horrible. And I feel embarrassed to tell my barber and stuff. They're like, well, what's it about? I'm like, I'm not sure, but not much. But yeah, it's not about making your first million, that's for sure.

Yeah, it's not get rich quick. It's like a real business podcast. And that's— that's That's the thing is since you have subscribers, because what I've thought about is like, let's say we change the name of, you know, of Startups for the Rest of Us. I think I just change it in the RSS feed. I change it with Apple and Spotify and then it just propagates. I think people, I'd need new line, you know, a liner art or whatever. I think people would be confused for a few weeks. And I guess all the incoming links would say Startups for the Rest of Us or My First Million. But aside from that, I just don't know the backlash. It's, it's it's less of like changing the name of a company is really hard, right? Because of the brand you've built. But changing the name of a podcast, I think is so— I, I'd like to think it's simpler, but I've never done it.

SAM

Our friend Nathan, uh, started this company called ConvertKit, which is amazing. And I'm an investor in, and it was crushing. And he changed the name to something. I forget what he changed the name to.

It was Seva. Seva.

SAM

Yeah. Which apparently, does that mean something offensive in Hindi?

It wasn't offensive, but it was, it, it, it has like a spiritual meaning. And so the back— he had backlash, right? And it was about cultural appropriation was the kind of phrase that was used.

SAM

Yeah. It's like a, it's a word in a different language. And people were like, you can't name your company that. And I, he's not a, he's like, at the time it was probably like a 50-person company. They probably did some research, but they mostly like just probably read the definition in a dictionary and thought it sounded cool. And then like a week later they changed it back to ConvertKit. Which I think is a great idea. ConvertKit's a good name.

Yeah, it's— that's, that's the other thing with the name change is, okay, so you're going to change My First Million. What are you going to change it to? Because naming is really hard, right?

SAM

Are you very hard?

I know some people who are really good at it. Most people are not, including myself. I struggle with naming. I always go too literal.

SAM

We would hire— I would hire one of those like naming firms. I actually think that— I think a naming firm is actually a great idea.

Yeah. At this level and at the, at the, the kind of reach that you have and the stakes and the race, I guess the resources you have, it would be a no-brainer.

SAM

Yeah.

Someone's really good. I don't, I don't know. Do you listen to Tropical MBA Podcast by chance?

SAM

Yeah. I like those guys.

Yeah. They had a really good kind of lower budget naming person. I say lower budget, let's say $5,000, $10,000 versus, you know, you can pay $100,000 or more. Um, she was super sharp. It was such a good episode and she had like an ebook on how she does it. And I was intrigued by that just because I— you look, you and I are going to be putting out new— whether we rename things or putting out new stuff for the rest of our lives. So how do we get better at this? Right? That's something I want to do.

SAM

Do you like that? Yeah. What were you saying, Ben?

BEN

I— you actually answered the question I was gonna ask, which is how much is a naming service? But there you go. But I mean, you know, I think like the thing about My First Million, like you said, sometimes a bad name is a good name. Because the thing is, it forces someone to react, like someone has to have an opinion about My First Million, they might not like it., but they're not gonna just like forget about it. They're gonna like, oh, what's that?

SAM

But dude, my companies are called The Hustle, horrible name. HustleCon, horrible name. One time I had a conference on content and I called it ConCon. No, no. Um, a meetup series called Pizza in the 40s. Uh, our subscription service called Trends. Like, I'm not good at, like, I, I, like, I've done Trends is good.

The Hustle is pretty bad. The rest of them are tough because the hustle, hustle now has this negative, or it has for several years, this hustle culture, right? It has a negative kind of connotation. So I guess if you're leaning into that, at least it gets attention, but it's a tough one to do.

SAM

So Rob, how do you describe your, your, who you are in a professional sense? How do, cause I was going to introduce you, but you're, you're, you're pretty eclectic that I don't even know how to the proper way to do it.

Yeah. I mean, bottom line, man, I used to be a software developer and then I didn't want to work for other people. So I started startups and first it was, I mean, in 2006 it was downloadable software. There really wasn't SaaS. And then it became SaaS, right? That's what you do now if you're in software. So I became a founder, serial entrepreneur, launched a few, acquired a few, and along the way started blogging about it. As you know, as you were saying, I wrote a couple— I've written 3 books about bootstrapping startups. I bootstrapped everything. I never raised funding. I'm not anti-funding. I'm not. I think funding has a time and a place, but I am anti the narrative that in order to start a startup, you have to raise funding because that is just not the case. I think 1% of companies 1% of tech companies need funding and the other 99% really shouldn't, shouldn't do it. So around 2011, then started a podcast and then, uh, no, that was 2010. And then 2011 started my events called MicroConf. And, um, and then just a couple of years ago launched an accelerator for SaaS bootstrappers.

SAM

So you, um, I wanted to go to MicroConf years ago. I remember that. And I didn't have enough money to go, so I'm going to have to go soon. But how— what were the name of some of your software companies? I know Drip. And can you reveal like how big some of these grew to?

Yeah, Drip grew into— well, I mean, Drip is tens of millions now, but I sold it in— in 20— what year was that? 2016. Grew it to a few million bucks before I sold it.

SAM

You grew it to $3 million a year in revenue and then it now does tens of millions of dollars.

Oh yeah, absolutely. I mean, this is email, email service providers or really any type of SaaS. If you double down on it like and you stick around for a long time, this stuff just, it compiles, it goes up every month if you're doing it right.

SAM

You know, you're selling it.

No, never, never a day have I woken up and thought, I really wish I was still working on that. Like I learned we were a team of 10 when we sold it and I learned what I needed to learn and it was enough money that I never had to work again. And that had been a goal. I was 41 maybe when I sold it, and that was a lifelong goal, you know, to have enough money to not work again. Yep. And I knew I would— I knew I would work.

SAM

Well, what was your number?

Well, I don't want to tell you how much.

SAM

No, but like, you don't tell me what you sold for, but like, in like when you said my goal is to earn this much, like, what was the threshold of not having to work?

Oh, that's interesting. You know, when I was 25, I just thought it was millions. I never actually calculated it. And then as I got into my thirties, I started saying, well, what's this 4% rule thing that you hear about in personal finance? Right. And I actually think the 4% rule is bullshit. Um, I think you need to be, you need to be a little more cautious. So it's about 3, 3.5%. So then the rule is if you need, if you want $150,000 a year to live on and you have $5 million in the bank, then the idea is that if you do the 4% rule, you can take out $200,000 a year. And never, um, touch the principal because stocks and bonds and other investments are, are due and inflation are working there. So a 3% rule would give you about $150 grand. So I'm not using my numbers, but you get the idea. So it quickly became apparent to me that when I was in my thirties of like, I think somewhere it's somewhere between $5 and $10 million, I think is most people's number. It depends on where you live, depends on how you live. Um, but I think anything north of $10 is like, like, It is excess. I'll say that. I, I'm north of 10 and I, and I feel like I did, my life didn't change. There was some point between 5 and 10 where it was like, yeah, that's enough. You know, I still like having the money and I do things with it, but, um, definitely it's not like I would have had to work again, even with a major stock market downturn or something.

SAM

That's pretty cool. $3 million with 10 employees is a pretty sick business when it's software.

It was very efficient. We were also really, I mean, I was bootstrapped. I should have raised a round. I should have raised a seed round because it was way stressful and I was— I burned out pretty hard on it. And that was part of— there were several factors into selling for me. And I'm curious if you, you know, have talked about why you sold as well. But for me, it was like, number one, if I can never— if I can have enough money that I control my own destiny for the rest of my life, that was a big win. It was the only way I would sell.

SAM

That was the only reason why I sold.

It's just like, take the cash off and now you can do anything. I mean, I started a damn startup accelerator, right? So we fund bootstrap SaaS founders. I'm not going to make money from that. And that's a 5 to 10 year play to make real money, right? To actually get the carry back. I take a salary, but it's like a token to what I could be making somewhere else. Um, and so I can now do play long ball with it because I'm not thinking, oh, how am I gonna, you know, how am I gonna do my big score? I never wanted to be worth— I never— my goal was never I need $100 million or I need a billion. It would be— I'd be fine with that, but that's not— that wasn't the goal. It was to have that freedom.

SAM

I sold to have that, but I wish the, the thing about my company is that I loved it. I mean, I still, I'm still here and I love it. Um, like I hate it and I, I hated, uh, like there was days where I'm like, this sucks. I hate media. I hate dealing with people. Of course I had like those normal things, but like the thing is, is that like I started my company because I was just blogging for fun when it didn't make money and I didn't actually think it was gonna make money. And now that I have something. I still do this because I just am a compulsive and I love it. And so I, I love my company. I just wish, I wish I was wealthy that I didn't have to sell it. Do you know what I mean? Yep. And so, because now I know I'm gonna have to go and start it again one day.

You're gonna have to start something and that one you won't have to sell, right? You'll be in a position where you can decide to, to do it or not and you can make bigger bets because if it goes to zero, it's not like you're sitting where I was in 2015 where it's like I am literally worth millions and millions of dollars on paper. And I have actual liquid net worth, about $400,000 in retirement savings between my wife and I. And I have about $50,000 in the bank and our house, which had no equity because it was, you know, it had gone down or whatever. So that was it. So I was like, I felt way overexposed to something tragic happening.

SAM

When you are doing $3 million in recurring revenue, I'm not sure if you— how you do, like, if people pay upfront or whatnot. But like I've seen ConvertKit's numbers, like all the public stuff that they reveal, and they didn't have a significant amount of cash in the bank. Was your, was your thing the same way where— Absolutely. We did it because like, you think 10 employees making $3 million, like, oh, you should have like plenty of money. But what was the truth?

The truth is that growth just destroys cash. Like no matter how much cash we made, I've, I was spending it on AWS bills. I was spending it with SendGrid. I would hire another contractor. I would hire another employee. The moment we grew by $10,000 in a month, let's say, of monthly recurring. And I'm like, great, now I can hire another engineer because, oh my God, we are understaffed. So at 10 people, we were way understaffed. And yeah, I'm trying to think. And that's where, like, my decision at that point was I'm either going to raise an angel round, like a seed round. Or we should sell it. And that was, that was the decision of do we double down on this business for another 2 to 4 years, or am I ready to, to, you know, make, make that choice of letting it go?

SAM

And so that was— I was a Drip user. Who owns it?

Well, what's interesting, so Leadpages bought it. Leadpages had raised $38 million in venture and they— it's actually a parent company called Avenue 81 Incorporated that owned Leadpages and then acquired Drip. So there's two products under one umbrella. Well, pretty soon within the Avenue81, you know, CEO realized the opportunity here is Drip. Like, Drip is a multi-billion dollar opportunity, whereas landing pages are, you know, the whole market at the time was $80 million, maybe $100 million. And that's, that sounds like a lot to us, but they're venture-backed, so they need to get to billions in valuation. So they actually sold off Leadpages, and the company is now Drip. So Drip owns Drip now. You know what I mean? Like it's, it was a turnaround. I don't know if you, I don't know if you ever heard that this happened with Best Buy where they acquired Geek Squad. And now like Best Buy would not exist without Geek Squad because that was like all their net profit through the last 15 years. That is, that essentially happened with Drip. They just refocused the whole team that had 170 employees. And I got to start handpicking people from the Leadpages team and pulling them over to help grow the team. So when I left, there were 100-something people working on Drip.

SAM

Do you feel like— see, remember like when you're a kid and you used to date someone and then you see her with another guy and you like feel just like that, that gel— you feel like anger and jealousy and you're sad? Do you, do you still have that? Do you have that emotion when you see Drip?

I don't. And but, but I will say that there have been some things that have happened that have that I haven't been happy with. So they like raised prices and they didn't do it very well right after I left, like a few months after. And I was like, you guys are better than— like, I would have done that so differently. And if I was in the room, I would have said, don't do it. They just did it really fast. They didn't grandfather, you know, they just made kind of all the 101 mistakes. And that sucked. And then there was a huge backlash against Drip, which is part of my legacy. Like Drip is, you know, it's like The Hustle will always— you will always be the founder of The Hustle, right? And I will always be the co-founder of Drip. They, they've messed with the UI, they've reshaped it and stuff. So when I go in now, I'm a little bit like, ugh, I liked it the old way. But, but I don't feel it's not the ex-girlfriend thing. It's more of a, I did have to let it go, you know, and just, and just let it go. I still use it. I, I mean, I'm in it every day. It's such a good tool.

SAM

Do you, that, that's a good sign. Do you, um, and then MicroConf, was that a big business? Cause I'm, when, when I started HustleCon, I like research you guys to steal ideas, but like also like to make sure it's a good business. And I was like, well, Rob's pretty savvy and he's doing it. So like, yeah, I could probably make a profit off this.

Yeah. Yeah, it was definitely, you know, it was a side project, like a hobby all this time, right? Until about 2 years ago where when I left Drip, I had this big decision of like, I have this podcast at the time. I had a co-host with the podcast. I'm solo now. Had MicroConf. Do I sell all of that? I literally thought of just leaving the whole entrepreneur, like, blogging, podcasting thing and going in, like, I was going to acquire a tabletop gaming, the second biggest tabletop gaming website. Right.

SAM

Which is like, what's a tabletop game?

I don't know. You know, like Settlers of Catan or like Dungeons and Dragons. So it's like, not like a board game is Monopoly. Right. But then there's like levels above that of complexity and stuff.

SAM

And so, which are booming right now.

Huge. Well, COVID helped, but also they're just, they're super popular. And so I was like, that's a hobby of mine. And I was like, I really want to do it. And then I started talking to the owner of the site, who's great. Great dude. And I'm like, what are your numbers? And he started giving me the numbers. And I was like, this makes no money. This may— and he's like, yeah, dude, tabletop games make no money. Like that, you know, there's the few, there's the Catan and there's D&D. There's like 10 or 20. Everything else kind of is— I'm overgeneralizing here because certainly there's other, but it's not like startup. Like we are so spoiled with startups where we don't manufacture physical things and you don't have returns and you don't have excess inventory and you don't have warehousing and all that stuff. And the profit margins are thin. And et cetera, et cetera. So that's when I doubled down on all of that. And so, yes, your initial question was, is MicroKump a good business? Yes. Will we sell? Let's see. We'll sell 7, like low 7 figures, like $1 million, $1.5 million, I think, in top line this year, maybe somewhere in that range. I need to look at the budget. You can tell that I have someone running it because I should know that. I would know that number if I was actually into it.

SAM

Will you be able to— and I mean, if you do 1.5, I would, I would hope that you probably do like 300 or 400 in profit.

Um, I think so. Although here's what we do. See, we are not running it as a profit machine. We are running it almost, it's become like a service to the community. Um, and so we run a bunch of the events at breakeven or loss. Like our local events are where we go to San Jose or Atlanta or Austin, Texas. We do a one-day event. Those tend to break even or lose money. And we're doing it to try to just expand. Like the mission is to increase the number of independent startups in the world, right? That's what we want to do. Bootstrap startups used to be the term, but it's like, it's not solely bootstrap. Some people raise small amounts of money and to do that, we got to get the word out. And so we run it at a, you know, 10 to 20% profit, net profit margin. And we could make more money. We used to make more money. Um, 5 years ago or whatever, but there's just no need to at this point.

SAM

That's a pretty sick side, like a good hobby.

It was good. It wasn't before when I still had Drip, we weren't doing a million because we were, you know, we're going to do 15 events this year. When we were, when I was running Drip, we were doing 3, but they were big. They were big events. We would have, trying to think of what our top line revenue was even. It was half, you know, let's say half a million, $600 grand across 3 events. So it was good, but it's a brand, right, man. It's like the first year, We, in 2011, we went to sell tickets and we were like, we're gonna sell 200 tickets at $800 a piece or $500 a piece. And we sold like 70 at like $500 a piece. Yeah, it's a slog.

SAM

Terrible. And the shitty part, everyone's like, you're gonna make money off sponsors. And yes, you will. It's gonna take you 2 or 3 years though for them to trust you. Yep. And we almost, what I didn't realize with events was they buy like a year in advance. So like our first sponsorships were like $2K a piece. And then we started getting the $50K and $100K, but they booked a year in advance. And I was like, wait, what? So like, it's, it's a, it's a crazy business.

Yeah. I personally wouldn't, I kept saying to my, I had a co-founder with that and then our event producer. And I kept saying, I don't want to be in the events business. Right. We had one event and then we expanded it to two because we wanted to do one in Europe. And then we expanded to three because we wanted an earlier stage event. And I kept saying, I don't want to be in the events business. And they kept telling me, that's the business. This is an events business. You've started one, you know, but I did it more as a community. I want to— I always thought of it as a community because that's like MicroConf has an online community and YouTube channel and all that stuff.

SAM

Ben, you look like you're about to say something.

BEN

No, no, I was just— Oh, you're laughing. Yeah, I was just laughing. Do you, uh, I, I, who starts a business, an event business, and doesn't know it's an event business?

SAM

But, uh, dude, I was the same way. I started— when I started HostCon, I was like, this is This is stupid. This is just a means to an end. We're getting out of this immediately. And then it's like, uh, it's, it's kind of like when you see all your friends starting software companies, you're like, dude, events are embarrassing. Why would I want this? Like, this is stupid. It doesn't, it's too hard. But then once you get a little more confident in yourself and you're like, well, if I accept it for like, for what it is, it's actually pretty neat. Um, yeah.

And there's nothing like it, like in this, even let's say pre-COVID. From 2011 until this year, over the last 10, 11 years, there's a lot of online communities. Anyone can start one. You get a few hundred people together. There are so few people who not only run in-person events, but who do them well. And if you can do that, it is an incredible competitive advantage. And not even that we have that much competition, but it is, it's not just like, I'm gonna run a business and make money. It's like the community of MicroConf is so tightly knit and it's because we meet in person. You know what I mean? You just, you have, I mean, you, you've experienced this where you go to an event, you meet someone in person and we, the retention rate was 60 or 70%. So you come back to the next year and everybody kind of knows each other and then you get new blood and you know, so there was, it, it built a way better community than if we did not have in-person events.

SAM

So because your job, because your career, you see a lot of like crazy software companies, some of which maybe aren't necessarily huge, But they are, could be surprising because you're like, I cannot believe someone's making this work. And you probably are able to spot lots of opportunities. We asked you if you knew of, uh, we asked you ahead of time and I'm curious if you were to think of any, any software companies where you see and you're shocked at the, that this is like a problem that needed to be solved.

Yeah, I see a bunch. So I have some, I have some both ideas that I haven't seen implemented that maybe we can dig into later.

SAM

Uh, let's do, yeah, we'll do both of those. Yep.

But there, so I'll talk about a couple. So TinySeed is the startup accelerator I run. And so as a result, you know, we've had across what, 4 batches? Is that right? 4 batches. We've had 2 or 3,000 applicants. So I've seen a lot of SaaS companies come through. Wow. And what I've, I've been surprised by a ton of them. Let me just look at one right here. So CRM or kind of customer interactions applied to any niche and the smallest niche you can imagine. So like home improvement contractors, the founder of Builder Prime is the size— is SaaS. We funded it with TinySeed and he had a home improvement project and he said the experience dealing with the contractor, the contractor was fine, but the communication was like text and then email. And it was anytime there's a bunch of texts and email, that can be a product.

SAM

What was the name? Build a what?

Builder Prime.

SAM

Builder Prime.

Builder Prime. Yep. And so it's in essence, I think he might call it CRM for, yeah, he calls it best CRM, but really it's not only the sales process, but then it's the communication during a home improvement project. And so like, shouldn't you, I would say, well, shouldn't, couldn't you use Basecamp? Isn't it like project management? Or could I use Microsoft Project like online? Right? Cause you could, but it's like, no, this is a strongly typed version of that. That is completely built for their needs.

SAM

How's this going?

It's going really well. I can't disclose revenue, but I'll say anyone who's in batch 2, any of those companies are going to be, you know, mid-six figures into seven figures. Right.

SAM

The founder of HubSpot, Brian Halligan, came on the pod and he told us that when they— I'm going to paraphrase the story. I might get a little bit wrong. He said that when they first started HubSpot, they were like at a fork in the road and not sure which way they were gonna go. And for a minute, I think they even created it and even had some sales, but they were like, well, let's like, HubSpot is a CRM, but then let's create like LawSpot. So it's like, uh, HubSpot just for lawyers. So instead of like making it one for everyone, we're gonna make an individual one for different industries. And so let's create LawSpot and just get lawyers to use it. And that's kind of basically what this company Builder Prime is because you would say like, well, why can't you just use HubSpot? Why can't you just use Assign whatever you want it, whatever it is. I understand. And so, all right, this is a cool company. How big is the team on this? What, what, Ben?

BEN

My other question is, um, like, do you have any companies, Rob, that you work with that are building apps on top of Salesforce or HubSpot that are like building in those ecosystems? Or do you think they should always go the direction of Builder Prime and just build their entire own ecosystem?

We have one who is built on Heroku. We have one who's kind of built— is a WordPress plugin, kind of built on WordPress. They're actually doing really well. It's Castos. It's podcast hosting. They're, they're into 7 figures, but there's no, you know, so the thing is, is with building on HubSpot or Salesforce, there's this platform risk, right? 'cause I had an angel investment that was doing really well, was built on Shopify, was a Shopify app, and they started killing it. And then Shopify came a-knocking and said, "You gotta start paying us a big chunk of your revenue or we shut you down." I mean, really, I would say it's shady shit, but it is what it is. It's platform risk, right? So that's where we have to be aware. If you go to sell a SaaS company and you're solely built on top of a platform, you sell for a lower multiple than if you were on your own. So as a result, what we say when folks come in and apply and say, hey, I'm only on Heroku, or if we, we see Shopify apps come through, we had to have seen Salesforce apps come through. I don't remember a HubSpot one, to be honest. But what we say is, cool, it's not a non-starter, but how are you thinking about this? Are you building for what other platforms? Are you building for how do you escape that? 'Cause by the, you know, when you're $500 grand a year, no one cares. When you're $5 million a year on a platform, they notice. And that there's, there's a danger there.

SAM

That's, that's pretty cool. That's interesting. I mean, I knew that was true, but I didn't know that Shopify could change the prices that they charge.

Seen it happen firsthand. Yeah.

SAM

What else is interesting?

Go ahead. Yeah. There's, there's another one. Um, this one's interesting. It's called Scraping Bee. And the cool part about them is they are public with their revenue. So I can actually at least give you an idea. So they crossed $1 million in annual recurring, uh, just 2, 3 months ago. And if you look at what it is, is it's, they allow you, if you want to, um, scrape the web, right? If it's like, well, I want to get all, you know, the products off of any, this particular e-commerce site, you can go in and it's not a GUI. Like you need to write a little bit of code, but then they have all the servers that allow you to get around. Being blocked by APIs or whatever. And when you think about this idea, it's, it's like, well, that sounds like a nice little $5,000-$10,000 a month idea, right? They're doing north of a, you know, probably $100,000 a month right now.

SAM

I haven't looked at their revenue recently, but like, it says they're going to employees.

Yeah, it's 2 employees. It's the 2 founders. What they're doing, it's crazy. We're encouraging them to hire actually, because here's the problem. Let's say they wanted to sell. I'm not saying they do, but if they wanted to, that's a problem. Like, they would, they would be worth more if they were a team of 5 or 10 than if they're only 2, because they're making a bunch of profit, but it's— there's risk there, right?

SAM

Do they have— is this like, uh, one of those, uh, public revenue things on like the Bear Metrics or whatever?

You know, I think they just disclose it on Twitter. It's Pierre DeWolf's. Yeah. And it's like every couple months he'll say when they hit a milestone, They'll be like, we hit this. And, um, the co-founder, I mean, co-founders Pierre and Kevin are really cool and transparent and they talk a lot about, I mean, it's content and SEO and they have grown crazy fast. I believe, and my memory serves me correctly, that when they joined TinySeed, they were at $4K a month. And this was 2 years ago, tops, 18 months, 2 years. I, you know, so it's like to go from $4K to ostensibly what, $90K, $100K, they're in that range a month. Um, pretty cool.

SAM

These guys should raise money maybe.

Yeah, they should. They could if they wanted to. It's up to them.

SAM

Right. But the valuations right now for a company that's growing quick that has a million in revenue is like $50 to $100 million.

Yeah. It's nuts.

SAM

I know. So like if you could raise $5 million and just do 5, I mean, that's kind of interesting. That'd be, that'd be easy to justify.

Right. But it depends on the founder. Right. It's like, that's one of the things that a lot of bootstrappers They don't want to get on that. Once you raise that money, now you're on the venture track. Right. And it's like, I got to raise every few months.

SAM

I'm supposed to get hired.

Yeah, but we're different. TinySeed's for bootstrappers. And so with TinySeed, folks can run their business and take profits out. We actually fund LLCs and they can take profits out if they want, or they get paid. We get paid if they take profits out. Cause we, we, you know, buy a percentage of their equity. So basically, if they take dividends out, we, you know, serve pro rata in those. Or if they were to sell the company, again, we own stock, so, or units in LLCs. So we get that percentage when they sell.

SAM

But is that actually going to be profitable for you, you think, more so than trying to get, trying to do the traditional model where you throw shit at the wall and 10% maybe works?

Right. Well, we, we are still in the traditional model of we've funded 59, 60 companies to date and we will fund another 100 and we have enough money right now to fund another 120, 150 in the next 3 years. So we are still in that model of making a lot of bets. What we're, what we see is that our bets, like, I don't think we will have a billion dollar outcome. I just don't see that being reasonable. I think we have a lot of $10 to $50, $10 to $100 million outcomes. And the number we've run a bunch of models. And in fact, if you go to tinysuit.com/thesis, you will see my co-founder is a data— was a data scientist, PhD in computer science, and we ran a bunch of backtesting on anonymous SaaS data. Uh, I think it was several thousand companies and looked at our, our funding approach versus, you know, what it would return. And it will return venture-like returns with, I believe, lower downside risk because we invested— we invest at the early stage at low valuations, in essence. Wow.

SAM

What else is interesting to you?

Um, yeah, you want another, another company?

SAM

No, tell me what ideas that you think there's opportunities in.

Yes. All right. So here's, so I always, when I start with ideas, I'm such a B2B SaaS founder, right? So I start with the problem, right? And so first, anytime I see someone doing something in Excel or a Google Sheet, I think to myself, that could, that's an idea, right? If you take it, or if there's a bunch of email, you know, or texts back and forth. Um, those are, cause it's communication or it's just storage. There's a couple of things that, um, I'm pretty fascinated by. So one is podcast apps are doing quite well. Like we're in Riverside now. We've funded, I'm invested in Squadcast, which is a competitor of Riverside.

SAM

Um, and I think, uh, both of them we're using Riverside now. We use Squadcast. We use Zencastr.

We use everything. I was with them before. Yeah. With Squadcast. And then of course, podcast hosting, right? There's Castos and Libsyn and others. And there's even podcast editing, like Alitu. I, we use, I use Audacity and then my editor uses Adobe something or other, but like Alitu, A-L-I-T-U, is podcast editing in the browser. So like the stack starting to get there, we have disparate tools to do things, but when HubSpot launched, so I, so I know Dharmesh, right? Dharmesh and I were bloggers and speakers. We met at BOS in 2008 or something. So I remember when HubSpot launched and I remember thinking, but all of these things exist. Like in early days, HubSpot was like, it was like a blog, I think, plus a marketing website, plus Google Analytics, plus I don't remember what it was.

SAM

Something else. Like an email capture form or something.

Something like that. It was very simple, but I was like, I could, but I remember saying, Dharmesh, but I could build that, you know, with MailChimp plus WordPress, you know? And he's like, yeah, but. Business owners don't want to do that. They want to bundle.

SAM

And he was right.

I think, and he was right. I said, they're public and where you guys are an amazing company. I think of the same thing with podcast production where I right now, I mean, I've been running a podcast for 11 years and I have, you know, people helping with it. And I literally am in Notion dragging this thing over here and then sending an email that sends an email to my producer to do something that we then log into Castos to upload. You know what I mean? It's like, where's the HubSpot for that? Where's the bundling of the podcast stuff?

SAM

I have a strong opinion. I have two strong opinions. The first is I'm almost certain. No, I'm partially certain that for the most part, podcasting software and podcasting tools is a horrible business because a few reasons, very few podcasts are successful and most all of them are broke.

Here's my, here's the counterpoint to this, right?

SAM

Because I like to be, I am an investor, so I see the numbers.

All right. Um, Squadcast doing several million a year in revenue and they're not doing it on the fly fishing podcast. Think of the 3 avatars for a podcast. There, there's the hobbyist, my Dungeons and Dragons podcast, my fly fishing, and they're going to, they're broke and they're going to pay $9 a month. Right. And they're going to churn like crazy because they're going to start, it's too much work. All right. Then there's the next tier up, which is. Startups for the Rest of Us. I'd say My First Million is in that where it's like a single show. But if I go to pay $100 a month for Squadcast Riverside, $100 a month for hosting, it's not a big deal to me. Right. And I don't think it is to you. So it's not $9, but for you it's like $100. I think if I were to say, oh, My First Million should pay $500 a month for each of these, you start to feel like, I'm not sure that's worth it, but there's a number there. Okay. So there's a, and they, and we don't churn. I mean, I've been doing it for 12 years. You guys have been doing it for several.

SAM

It's like the, the, the S&P of, of podcasts.

It's the S&P that actually sticks around. There's hobbyists, there's S&P, then there's one level up. So there's iHeartRadio, there's ESPN's podcast, there's the Kevin Smith podcast, Smodcast, right? There is Kara Swisher has a whole network, Gimlet Media, NPR. Like once they— especially once they went remote, that's the enterprise.

SAM

But how many of those are there? Because for example, like Vox. I think Vox was trying to sell their CM. Like, it's all media companies are like, oh, we built this proprietary technology to like get our articles shared better and like things like that. And like, cool, I would love that technology. But they want to go out like Washington Post is doing this. They want to go out and sell their software. And I'm like, how many fucking media companies could pay $100 grand a year for software? Most media companies are broke. And so that's my same thing to podcasters. But all right, I agree those exist. I want to be— I need to be convinced that there's like enough of them.

Ben was going to say something. We should let him talk.

BEN

I was blown away. So we got a pitch from one of these recording companies, one of the ones that Rob mentioned. I won't say which. But I assumed that the pro tier that Rob was talking about would be like 10x what a normal plan was. And it was like 100x. It was like It was like $100,000 plus a month for, um, a month, a month, a month for some of these pro features. Yeah. And, um, the squat— I was blown away. I could not believe it. I was blown away. But anyways, you know, it's worth it for, for a lot of people. So anyway, well, for that type of company, you don't need that many customers, I think is, is maybe the point.

SAM

Really? Do you get crazy amounts of features with $1,000 a month?

BEN

I mean, they're cool. They are cool features. They're cool features.

SAM

Wow, that is crazy.

That does sound high, I will admit. That's crazy. That's where you don't need that. You don't need that many.

SAM

Okay, so podcasting is— you're saying it's a good business because there's actually enough customers to make it work, right?

Yeah, yeah. And podcasting has this other thing that, that is I think undervalued or just not talked about enough. It's this concept of a dual funnel or a split funnel where you have, you know, who else has this is, um, electronic signature. eSignature has this where you have this super wide funnel. There's either free users or very inexpensive users on the low end. And so a lot of people use it, thus you build a brand and you just have 5,000, 10,000 customers, whatever. Some are just users, some are customers. You also, if you have any type of viral loop, that's amazing, right? You send the link to Squadcast or Riverside, you send a link to get a document signed. Oh, a little bit of virality. But then on the top end with eSignature, similarly, you have realty mortgage brokers who, I need 8,000 documents a month signed, and suddenly that's at $10,000, $20,000, $30,000 a month. That dual funnel is incredible because when you, if you're just enterprise, then you're enterprise. Right? And it's like Oracle in the old days. It's like, all right, so we need to close 500 deals this whole year, but each deal is $1 million or $2 million, right? I mean, that's— it's like these massive deals and it's just this grind of enterprise sales. But when you have the low-end funnel and the high-end funnel, it's, um, it feeds on itself and it helps you have a more stable business.

SAM

The companies that are able to charge, uh, 6 figures a year in software, do you think that a lot of times their software is actually better than the $5 a month tool tools that are in the same category, but for different people. Like, is it, is it, you know, if a company, if it's $5 a month versus $500,000 a year, is it actually 1,000 times better?

No, it's not. And I would, it's not, um, $5 a month, I would say, or whatever, a more accurate one is like, you know, is if I'm paying $250 a month versus $25,000 a month, let's say that's, it's 100x difference. Those are probably relatively similar. And in fact, a lot of the pricing advice we give to our founders, um, or I give on the podcast as well, is the moment someone approaches you, a potential customer, and says, cool, we like your software, we need to redline your terms of service, or we need, uh, to invoice with POs, or we need single sign-on, or we need a Salesforce integration, or we need— there's, there's this whole list of things that instantly should trigger you should pay about 100 times more, that your price should go up because the sheer headache of dealing with procurement and going through that process and the maintenance and all the, you know, the interaction, it's not that the software is better, it's that the time and the headache and the pain of making that sale and maintaining that customer is, that's where it's at, right? That's where the money's spent.

SAM

But is it that hard to like, do the single sign-on or like, isn't there, is there not like an 80/20 thing that you can do where it's like it works for most high-end customers?

Well, there's two things, right? It's, are we pricing on value? Because I price on value, right? There's— you can price on cost, you can price on value. What's the third? I forget what the other one is anyways, but certainly I'm not pricing my SaaS on cost because I would have no margin, right? So I'm going to try to price based on the value. And, um, I could build single sign-on. It's like, hey, let's let everyone have it. But it's a trigger that that company has the ability to pay. And frankly are going to get a lot more value out of it than a one-person team using it. Right. You know, it's like Gimlet Media versus Rob Walling comes to, you know, sign up for your podcast recording. It's like Gimlet Media should pay a lot more than me, not because they, they need that many more features, but they just should. Their whole business is built on it and they're making millions.

SAM

Matters more to them.

Yeah.

SAM

Are there any other ideas that interest you at the moment?

Oh yeah. So I gotta be honest, man. I mean, this is not even a SaaS idea. I'm just gonna throw it out. You know, you, do you know the website examine.com?

SAM

My favorite website out there. I would put it in top 10. I'm a paying, I'm a paying member. There's a new one that I'm looking at called, uh, consumer. It's like examine.com, but for, uh, brands for vitamin brands. Yep. Anyway.

Yeah. Examine is nutrition information you can trust. So I interviewed the founder, uh, on my I love Saul. Saul's— he's great. I interviewed him on the podcast. Sherry, my wife, has been friends with him for several years since they met at an event. So I had him on the show and I was fascinated by it because I'm like, it's nutrition information you can trust, right? And you know that, but I'm saying it for the audience. Where is the Examine.com for crypto and NFT, like for Web3 stuff? Because I feel like there's so much crazy info out there.

SAM

Agreed.

And there's so many opinions and religious, you know, not truly religious, but like religious fervor. And the, and the Bitcoin maximalist and shit. And it's like, someone can do this, right?

SAM

This business and the business. So let's talk about that. Examine. I've talked about Examine on the pod a ton because I think it's one of those sites that I see. I don't think I know how big they are. I mean, like I would imagine like not big, like 2 or 3 million a year in revenue, but I have no idea. That's just a guess. But I know it's not big cuz they don't hire a ton of people. And I was like, this is one of the most undermonetized sites I've, I know well, I actually think that their— Examine could be significantly— Examine could be a $100 million a year business, I think.

How, how, how do you think?

SAM

So there's a bunch of, so I would, I think that they, for one, they don't do any affiliates. So something like Wirecutter, you know, Wirecutter?

Mm-hmm. Yep.

SAM

Uh, so in, um, in New York Times, you know, they're a publicly traded company. They're the Wirecutter revenue got classified now as, uh, like other revenue. So I've been trying to like decipher it and figure it out. And they do something like close to 9 figures in sales from affiliate affiliates. Examine doesn't want to do that. But I think they, I think they could, I think they could do it in a tasteful way and it could work wonderfully because what Examine doesn't do is they don't tell you which brands to buy, but I think they should, cause that's what I want. And that's what a lot of people want. Additionally, I think you could sell to doctors. So there's actually another company out there that does like $400 or $500 million a year in sales. And they sell to doctors. And when you go to the doctor and you have like a rash, they just like— it's like Wikipedia for doctors. They like look it up and like the latest, uh, studies are there on that.

Interesting. And Examine, you know, I didn't talk to Saul about that, but they don't want to do it because they don't— do they not want it to taint the— they don't want to become a review site. I mean, that's why we don't trust review sites, right? Is the—

SAM

but I trust some. I trust Wirecutter.

Yeah.

SAM

I mean, I think there, I think there's this way to solve for that. Like, like Do like if Casey Neistat is a YouTuber who I like, if he tells me a cool product and then there's an affiliate link there, I don't care that it's an affiliate link.

Right.

SAM

But anyway, what, uh, exam— I also think examine.com could work for injuries.

Oh, like medical, like, hey, my knee, because like to get the definitive.

SAM

Yeah.

This is that, or just illnesses in general, right?

SAM

You Google symptoms and like rehab.

Yeah.

BEN

Are you sick or injured enough to make that a thing that you would pay a monthly subscription for?

Not me.

SAM

Well, I don't know. I don't know if you could make money through subscriptions with that, but I do think that like when you have like an Achilles injury and you're like, I'm desperate, I'll do anything. I just need to learn. Like, because I remember when I was researching for my, like I had a pain in my leg. I was like, I like, I went to all the studies and I just read all the studies. I'm like, I'm just going to figure this out. I'm not going to read like an eHow article on how to do this. I'm just gonna go to source and like What's the, what's the thing that I'm reading about the studies, but how does, uh, Rob, do you know, how does examine.com operate? Like, how does that literally work? Cause all they do is they like pour through all the studies and find the ones that have a good sample size that have definitive proof. And they make a list of like, these work for sure. And then they have another list that says these seem like they might be able to work, but we can't say for certain. And then these are shit. Don't trust.

Pretty much. Yep. And they, their big hit early on, he said all this on the podcast. It was, it was all SEO, right? It was organic. And then they took a Google dive at some point. I don't know when it was, but, um, they had already implemented their subscription revenue. I don't even think that they had ads at one point. I don't know that they do anymore. I'm actually on the site looking around, but yeah, that's it. That's how they write the topic and their, what is their value? It's the brand. It's the trust. You know what I mean? That's why everyone goes to it because they have built that brand that you, you trust it and I trust it.

SAM

But, but how do they do that though? Do they literally just have one? They go, uh, all right, editorial team this week, you Steve, you're a writer. Your writing topic is, um, um, building muscles. So go and research everything that helps you go research creatine protein.

The, so if I were them, I would be looking— they've been around for a decade now. All the topics have been covered. I'm only looking for new information, right? I'd be monitoring all the journals, all the whatevers, and have subscriptions to all that. I don't know exactly how they do it, but that, that would be it, right? It's having, having a Google Alerts essentially for all the new medical stuff to just update. You just want to keep it updated.

SAM

That's crazy.

I can't imagine there's a new topic they haven't already covered in their thousands of pages.

SAM

And this would actually make way more money in crypto.

Totally. I mean, there's several, there's several niches where this, this would be interesting. The hardest part is there's a bunch of crypto news sites, and when I go to them, I just don't know, I don't trust them.

SAM

Yeah, I don't know, like, are these guys like these like hardcore libertarian, the world's gonna end, fuck money, like, fuck, uh, cash because it's just stupid? Or are they, you know, like, a great way to explain it is like basically, do you remember like the Mac versus PC ads Where there was like a, like a cool looking Mac guy versus a nerdy PC guy. And do you remember that animosity it created between Mac and PC guys? Now imagine if each person who owned a Mac or a PC had a million dollars of Apple stock. That's like, that's like the, the, the hate. That's like the vibe that you're gonna get.

That's right. It's religious fervor with money behind it now.

SAM

And so it's very hard for me to hear a crypto guy, even Sean. Sean's one of my best friends and he, but I know he's got a lot of crypto. So I'm like, but is this because you— are you telling me what you want to happen or what you think will happen?

Right.

SAM

So it's actually really interesting. What would you do to build that?

I would start— so first thing you have to do is build credibility. You have to start there. So I'd probably start a podcast so that people could hear my thinking week to week. Um, I would definitely be attending all of the crypto events anywhere to get into the network, to build trust, because if people don't— if you're anonymous, like if you try to build this anonymously, no one's No one's gonna believe it. So I would get into the network and then, um, follow the model. I would look at what did Xamn do? We know anyone who has done this model, what did they do in terms of, of, uh, content? And then obviously just hire writers and look at the white papers and give our opinions.

SAM

And this is actually a cool business cuz this business could last 100 years. So like if you look at like, um, Consumer Reports, Consumer Reports has been around for decades. They still do well into the 9 figures of revenue. So Consumer Reports is a, you know, review site that people pay money for. They're a nonprofit. So all of their expenses are public. All their revenue is public and everything, and they're still growing. And so like, if you do a good job of building a brand, like on this topic and you start reviewing stuff and you do a good job, you can review many other things and last for a very long time. Kind of a cool company.

Yeah. Yeah, they are still kicking.

SAM

Anything else interests you?

I am interested in, I mean, this, you know, normally I'm boring, boring businesses are my favorite, right? Because it's like B2B SaaS is, is the way to go. Um, I think anytime you can take a concept, like we've said with Builder Prime, um, you know, where it was just like CRM for customers. We have another company we funded called Client Hub, which is basically project management CRM for accountants. And then we have another one that's called Gymdesk, which is basically run your gym business on it. It's like kind of CRM and communication. So it's like, where, how many niches are there where that works? Some of these are going to be 7 or 8 for your businesses. Some of the niches are going to be very, very small. Um, but that's where you just have to pick. It's like, hey, am I a lifestyle bootstrapper? Cause I want a $10,000, $20,000 a month business. Um, but I like these ideas of, you know, it depends on your ambition. But if you want to stay small and just build an incredibly profitable business with 2 people working on a, you know, $100 grand a month, I mean, you can enter a less competitive space. If you want to grow big and grow faster, then you enter a space like electronic signature or like calendar scheduling links, which we funded companies in both, like Calendly competitor and, you know, and HelloSign competitor or whatever. There's a lot of competition. You have to move faster, but the market opportunity there is just tremendous.

SAM

Do you, uh, what do you, how do you decide if it's gonna be an 8-figure idea or much smaller? Is there a metric that you look for?

Yeah, that's an interesting question. I usually, so with Tiny Seed companies, when they apply, we say, if your ambition is to build a 7-figure annual recurring revenue company, then you're in the right place. We get some people who say, I really want just a half million dollar business. It's like, great. That's going to be a great business for you, but that's not really fundable for us. It just doesn't make sense. Um, I think a big piece of can it get into the, you know, and we'd love to see mid-seven figures and up, right? Um, but a big question of can it get there, a lot of it, it's less about market size because most markets are big enough. There are few markets that are too small. Most of it is, uh, the metrics of the business is where we look at the churn and we look at the pricing. And so if you're, if everybody's too price sensitive, to your point earlier, if everyone's a Fly Fisherman podcast and everyone's paying in, you know, $10 to $20 a month, and that's kind of where most people are, and then your churn is 10%, like, you just can't, you know, almost impossible to build a million, $2 million business. But when you get to the point where, hey, my average revenue per user is $100 or $500 a month, and your churn is 2 or 3%, you would have to own the whole market. Like, there's almost any market is big enough that that can be a $5 million business. All right.

SAM

My last question. How many of these folks building software companies that you see, yourself included, are non-technical?

Well, that's a great question.

SAM

And if they are non-technical, what do they do?

Yep. So I'm a developer or was. I haven't written code in years, but We actually ask, so we do a State of Independent SaaS survey and we put out a report and it like an industry report. And we asked the question, do you have at least one technical founder? Right. Or, you know, and yes or no. Right. And the number of SaaS companies kind of bootstrapped-ish SaaS companies with zero, with no technical founders. Is like, I believe it's 20%, 25%.

SAM

Wow. It's very possible.

It is. And usually what the expertise they have, they're either the subject matter expert, like we're going to build software for accountants. I was an accountant for 20 years, right? We're going to build software for UX designers. I was a designer for 10 years. They're either that or they're sales or marketing. That's what they should have. Now we've seen where there's a developer and then there's like the business person, the business guy or gal.

SAM

Which just means like anything.

Yeah, it usually winds up meaning you're not actually that helpful and you probably shouldn't be a co-founder. You know, if you can't sell or market or like have input on the product, you know, or develop it, like those are really the four roles, um, you probably shouldn't be.

SAM

So if I'm, if I like, I'm not tech, I'm not technical, but I, um, I can like I stuff together and use Zapier and I'm super creative. How do I start a, start a software company without hiring? Or I would, if maybe hiring's it, but without having a co-founder, right?

So for you, since you have money, you would either acquire something, cuz there's always stuff for sale that you may wanna acquire and then just grow if you have a content marketing expertise, or you would hire, you know, a developer or an agency or something to build it. If you don't have the money. Uh, a lot of people, non-technical, will work a day job and actually funnel money to the side to basically pay for a developer to do it. Um, the other two approaches I've seen are exactly what you said, which is I'm going to build my minimum viable product using Zapier and Notion and chewing gum. Right. And I'm just going to cobble it together to the point where, hey, if I get a few grand a month in revenue, this proves it. And now I'm going to use that to get it built. It's a harder way to go, but it's possible. The last one I've seen, which is genius, and this is what the founder of Castos did, because he's not— he's a single founder, not a developer. He worked a day job. He started a productized service, podcast editing, and he got it up to— I forget what the number was— $30,000 or $40,000 a month in productized podcast. He was one of the earlier ones. It was called Podcast Motor. He was working a day job the whole time.

SAM

So then while he was actually doing the editing, or he would— he did it and then got someone overseas. Exactly.

Yep. Yep. Or even, even as folks in US and Canada doing it. And there was enough profit margin that he then started reinvesting, you know, and said, well, now I want to build. Now that I'm doing podcast hosting, he actually was in the podcast space. Someone says, I have this WordPress podcast plugin for podcast hosting on WordPress. And I want someone to kind of adopt it type thing. Since he was doing something in public, they approached him, he bought it for not very much money. And then he built the entire, you know, what, again, as a 7-figure business. He's raised, you know, 3— aside from us, he's raised $750,000 and it's growing fast. So that's the other way to do it is like, I even— I was a developer and I had to do it nights and weekends too, you know, and I was pulling money away from the day job.

SAM

For the agency and hiring a developer, what, what's the best way to do that? Do a lot of these folks like— a lot, like when I was starting, everyone said like, oh, just go on oDesk and hire someone in India to do it. And I'm like, I don't know, man, that doesn't sound like I can like Like, yeah. So like, what are you— what, what, what, are there any agencies that you like? Or for hiring devs, are you hiring someone by the hour in America? What, what's, what do you typically see?

Yeah, I typically see, I see a lot of people going either through referrals, like you get into a community, um, MicroConf Connect or IndieHackers or whatever, Dynamite Circle, and you ask and you say, who has used someone whom you trust, right? So you try to get that referral. It's not just a a flat look because going to Upwork, which used to be oDesk, is kind of a shit show these days. The other thing is there are now these referral services aggregators. There's one called Trustshoring, which is run by a guy who attends MicroConf, but he basically knows a bunch of Eastern European dev agencies. And if you come to him and say, I want to build an iOS app, he'll say, cool, I have these 3 agencies that I, that I refer to. He's almost like a broker in a way, but like he's a good dude and he knows them, you know? And so he, and he's vetted them. And then there's one called clouddevs.com and they do the similar thing for Latin America. And so the nice thing about Latin—

SAM

Do you like Toptal or anything like that?

Toptal's good. It's expensive. Um, right. Cause I think it's $150 an hour. So it depends on budget and all that. If you're, if you're scraping by, I haven't used Toptal, but I've had friends use it and I heard quality was really good in the early days. And of course, like anything. It gets, you know, less and less, but, um, that's certainly something you could try too.

SAM

How much would you budget to create an MVP?

It depends on what it is. You're talking like a SaaS app? Here's the other thing, man. If you, if you are non-technical and you've never started a startup before, I would say don't build a SaaS app. It's too hard. Like go, I have this thing called the stair-step approach to bootstrapping, which is like start small with like a WordPress plugin, a HubSpot add-on, a Salesforce add-on, a Heroku add-on. And go build that, cut your teeth at it. It's way less expensive, way harder to maintain— way easier to maintain. You get the experience, you get some revenue, then grow it to enough that you can buy out— just buy out your day job. $8,000 to $8,000 a month, maybe $10,000 a month. Then now you have experience, you can double down and, um, and do it.

SAM

It's awesome.

To your, to your question of building an MVP of a SaaS app, $10,000 to $30,000 if I were to throw it out.

SAM

But, and you think a non-technical person could actually maintain that and understand what's going on?

Well, no, then you'd need to have that agency stick around. That's where I'm saying, if you're non-technical, um, you either need some money. I mean, this is why folks, you build it and you're, you pre-sell it. You get to the point where there's enough revenue that you can then justify, you know, raising funding, right? If you're, if you're non-technical or you have a side job, that's, uh, putting money into it.

SAM

Well, thanks for coming and talking about this. I— you have a good view of what's going on in, in this space. I think it's badass. Ben, what do you think?

BEN

Yeah, that was great. Thanks so much for coming on, Rob. Appreciate it.

Absolutely. Thank you guys.

SAM

I really appreciate it.

So good.

SAM

This is awesome. Um, do you want to give a pitch? Where, where do you people follow you most?

So I'm on Twitter @robwalling, and frankly, they listen to this podcast, they would probably like Startups for the Rest of Us. It's more focused on, you know, SaaS and startups, but 35 minutes every week for 590 episodes.

SAM

That's badass. I, I'm a fan. I've been listening to you for a long time, almost 10 years. It feels like, thank you. This is awesome. Thanks for coming.

Thanks so much, Sam.

SAM

Boom. That's it.