The Most Sued Podcaster in SaaS – Nathan Latka

Todd Chambers
Todd Chambers here, hello!

Welcome to another episode of the Masters of SaaS, a podcast brought to you by Upraw Media an agency that works exclusively with SaaS companies to help them scale up their paid media. On the podcast, we speak with the top 1% in SaaS - smart people who really know their stuff.

Like today's guest, Nathan Lakha, a serial entrepreneur and host of the Nathan Lakha Show, a podcast that focuses on data, so you can quickly understand the numbers behind the fastest growing SaaS companies in the world. I'm a huge fan of Nathan's show, and I have massive respect, considering he recorded more than 3,500 episodes - this is our 17th episodes, so this is what I'm up against! Nathan also runs Founderpath, which helps SaaS founders get capital by converting their MRR into upfront cash without the need to sell equity. In the episode we cover why Nathan is the most sued podcaster, Nathan's first SaaS company, Heyo, and his negative funding experience, how to convert MRR into upfront cash with Founderpath and why you should focus on revenue per employee, how Nathan bends the rules to his advantage, and how he batches tasks, saves on switching costs and gets more done. I had loads of fun chatting with Nathan and hope you guys enjoy it too. Let's do it!

Hey, Nathan, welcome to the show.

Nathan Latka
Todd Chambers, thanks for having me on.

Todd Chambers
Yeah, pleasure is all mine. So, for the people that don't know you - who the hell is Nathan Latka?

Nathan Latka
You know, it's a funny question. I ultimately am whatever people describe me as, and people describe me as very different things depending on who you talk to. So, I turn that back on you. How would you describe what I'm working on, from your own perspective?

Todd Chambers
I would say you're an entrepreneur, I would say you're a bit of a hustler. It seems like you have your finger in many different pies. And I would say you're an expert in SaaS. And I would maybe layer that with, as you said, potentially controversial in the eyes of some people. I think maybe the way you communicate, you're very direct, it can potentially rub people the wrong way. But I think maybe you're just a bit misunderstood. So that's how I would summarise you.

Nathan Latka
You're much nicer than I am!

Yeah, I mean, I can't verify this actually, 100%. But I'm going to make this statement. And maybe someone has been sued more than I have. But I'm pretty certain I'm the most sued podcaster, because when I launched the podcast I made a promise to myself that, you know, I didn't want to be Tim Ferriss and record four hour episodes, and I also didn't want to be, you know, John Lee Dumas and record fifteen minute episodes that were sort of fluffy about, like, "what's your biggest failure"? I want to short episodes with SaaS founders that were really hard hitting. And you know, I now have a situation where founders come on, we fall in love, they share great data - rich data, valuations, what they pay themselves, their profit, sharing their last run valuation, but then their boards hear it and they send me a cease and desist. And I get in trouble. But I ultimately end up winning most of those. So that's where the controversial part, I think, probably comes in.

Todd Chambers
That's absolutely crazy... So, I have a bunch of questions around kind of the origin story of yourself. But you originally had a company called Heyo, I think it was called, right? Which was, was that kind of your first endeavour into entrepreneurship? Like, maybe we can start there?

Nathan Latka
Yeah, I was 19. I was an architecture major and the mountains of Southwest Virginia...

Todd Chambers
Architecture?

Nathan Latka
Yeah, Virginia Tech. You learn a lot, by the way, when I now write angel checks, and a founder tells me that they were an architect major or a theatre major, I'm almost always interested because you learn so much about empathy. And many SaaS companies, the reason they fail is they don't know how to build empathy into the product. They just tackle it from, like, a pure, like, numbers, or pure, like, UI perspective. But empathy is critical.

So, yeah, I was an architect major, but Todd, there was a slight problem - I loved money. And to make money being an architect, you had to, like, it was almost implied, you have to be, like, 0.001% to go build, like the Guggenheim, which I was never gonna be. So, I started selling actually, much like you're doing, I launched a very small agency, you're probably much larger than I ever was. But I was selling one off custom Facebook fan pages, and ultimately said, "the way to scale this is, I don't want to spend 10 hour delivering each of these individual professional services sales - I'd rather build a drag and drop tool like Weebly or Wix would do for a website. But build that too, so people could pay me a monthly fee to drag and drop Facebook apps together". And that's when I found my developers. That's when I launch Heyo and that's when I learned what SaaS was.

Todd Chambers
And you were, like, 19 years old?

Nathan Latka
Yeah, I was probably 20, 21 at the point when I pivoted from agency to SaaS company. But again, I didn't know it was a SaaS company. This was just a way for me to scale my time without having to do work. So you charge a lower recurring fee, but not do any professional services work.

Todd Chambers
What did you mean, specifically, on the empathy side? I'm interested in what you meant there.

Nathan Latka
Well, to me, empathy is about emotions. You know, my empathy today comes across in a lot of the copy that I put out, you know, I think it's a very unique ability. I mean, I think this because people tell me, then I go, "you know what, you're probably right", right? They say, "Nathan, I open all your emails, like, the copy is always really interesting. It makes me curious every time, like, I learned so much, you know". Copy to me is what empathy means, and then how you position the copy will determine how you drive your onboarding flows, your upsell funnels, things like that in your SaaS product.

Todd Chambers
100%. You know, we offer copywriting services, conversion optimization, and we'd interview people, especially in copywriting. And you have to speak to the real world motivation, to the pain points. Because people buy an emotion, right? And then they reason with logic. So I think what you're saying is, speak to the human behind it. And don't just think about the numbers and the revenue and like us. That's kind of what you're trying to say.

Nathan Latka
It's the reason why today when I see a SaaS company who's not investing in building a community, I'm not interested, you know. It's so easy to rip off code today, the only real business moat a SaaS company has is the community. You know, you recently had Guillaume on with Lemlist, people should go re-listen to that episode, right, I mean, he was able to turn down that offer because he's built an incredible community, and he could probably sell them anything - he just happens to sell an email outreach right now called Lemlist.

Todd Chambers
Super cool guy, by the way. Yeah. Like you said, He's built such an amazing community and the Lemlisters, yeah, his community, the Lemlisters, indeed.

So, you had this SaaS product, Heyo. How long did you run it for? Like, how long did it take to build...

Nathan Latka
This was my SaaS education, right? I mean, I learned a lot. I scaled that bootstrap from my dorm room to about 60,000 bucks a month in revenue. And that's, you know, a lot of people do podcasts, they do stuff like this. And they just spew numbers with no proof. As you know, I'm a proof oriented guy, which is why on page 6, in my book, I put my tax returns from that year - 2013. And you can actually see the revenue when I was 21, in my dorm room, you see what we hit. And ultimately, what happened was, when we started having a success, I had investors reach out ask me to invest. I thought, "of course I want to TechCrunch headline", like, "of course I want to raise capital". So they gave me, you know, two and a half million, two million bucks at eight and a half million pre-money valuation, so 10.5 posts. I was like the richest student on campus, living in the most beautiful penthouse apartment above the theatre downtown. I'm like, this is what it feels like! This must be what it feels like.

But then you quickly realise it is a whole different ballgame, a whole different ballgame. My happiness went down, our cash flows went down, my team got less creative because their answer to every problem was throw money at it. I had a board that I hated, it took 10 hours a month to put together reporting documents for, a whole different world. In my opinion, it was a massive mistake, you know, we got an acquisition offer from iContact to sell the business for $6.5 million, slightly after the time that we raised, and I had to say I would have taken it, you know, I still owned 60% of the business at that point. So, you can do the math on what I would have made on that sale. But the board basically said, "Nathan, we just invested at a 10 post-money, we want to see you scale to 100 million, don't sell for six and a half!" and they blocked it. The thing with raising capital is that you lose so much optionality. And in entrepreneurship optionality is the king, not a TechCrunch headline promoting a big valuation.

Todd Chambers
So, what did you do? So they blocked you from selling? So how did things kind of manifest?

Nathan Latka
Well, this was my biggest mistake. I should have insisted that we sell the business because the timing was right. What I did instead was, I kept running the business for another three years, partly because I was comfortable. You know, I was CEO, we had revenue, I was paying myself I think 125 grand, right? As a very young person that was like, and I had almost no expenses, I was saving money like crazy, investing in real estate, all this stuff, I shouldn't have done that. Those are your best years of your life, most flexibility, you're single, there's no kids, you have very low expenses, your health is good, usually. I should have gotten out earlier. But what I did was I waited and I sold the business in 2015, at a loss.

And part of the reason I launched my podcast, The Top Entrepreneurs, in 2015, was because I didn't want other founders to go down that same funding rabbit hole that I did without understanding what you're actually doing. A TechCrunch headline spikes your traffic one day, and then it's gone. But raising capital can make your life a living hell if you don't understand what you're getting into.

Todd Chambers
So true. We work with loads of different SaaS companies, and they're funded. And the thing that always sticks out to me is that they make kind of really short term strategies, based on kind of short term thinking. It's like, "okay, we need to grow, we need to get to the next round". Everything is often dictated from that kind of thing over your shoulder, you have this funding. and I totally agree with the optionality to kind of... You're in control of your own destiny, right?

Super interesting! I no clue that you started the podcast because you had that really, really bad experience, and that was kind of my question. Did you start the podcast as a way to kind of grow that SaaS business or did it come afterwards? And I guess that's answered that question. So...

Nathan Latka
No, it was totally separate, completely separate. But, like, when you look at, from a financial perspective, you know, the money I made in my, you know, between 19 and 25, a lot of people think like I made a bunch of money on the exit. I made nothing on the exit, my money from Heyo came from the large salaries I was paying myself before we raise capital, because I was in full control, and I bootstrapped it. For context, the first large sponsor deal we landed for our podcast was worth way more than all the money that I made at Heyo over my first five years building a SaaS company,right? Media is very powerful.

Todd Chambers
So, you started the podcast. And yeah, if anybody's listened to your podcast, you obviously have a very direct style. And you just touched on that today, you know, you wanted to extract the numbers, the value, you didn't want any fluff, you wanted there to be like that, right in that sweet zone, where people could listen to it and just get like a ton of value. So, how did that go in the early days? Was that like, "okay, I'm gonna try and make a podcast that I would want to listen to"? Like, what was the kind of the thinking behind it?

Nathan Latka
The podcast was just a way to set up an environment that was ripe for me to get what I wanted, which was data quickly, right? I'm in the lead position as the podcast host, my guest is in a position where they are already in a pre-disposition spot to know that they're gonna have to answer questions, right? So, I have permission to sort of go and ask these questions. And the only question is, how deep and how fast? And how much? How many questions can I ask in a 15 minute period? So, the podcast was just the right mousetrap just sort of set up the system to like, learn quickly, and that's what I was optimising for.

Todd Chambers
But what was the, kind of, the endgame? Were you thinking, "okay, I'm just going to build this podcast and then monetize it", or is it, like, "I'm going to set up an investment fund, and this gives gives me data"... And like, yeah, what was the endgame?

Nathan Latka
Well, I think a lot of, sort of, people that are full of hot air would say, "this is all tactically plan", you know, "to have success". And they say it was strategic, I planned it from the start. It's all bullshit, right? The best founders pivot really quick. They do things they love, and then they figure out how to monetize later. And I was the same way, I had no idea what the podcast would turn into.

Now, some things I learned since 2015, it was a couple things; one, there's a lot of podcasts. So, if you're not entertaining, you're going to lose, even if you're smarter than everybody else. There's a lot of very smart people that can't hold an audience. And they wonder why these people, like, Jake Paul, get all the attention - because the guy's entertaining! You have to entertain, and that earns your right to then educate. A lot of people are really bad entertainers. So, the reason I've amped up the aggressiveness is because it's more entertaining, my retention metrics on the podcast go up the more controversial an episode is, so, I will always be and always try and be more direct, shorter, and more to the point.

Todd Chambers
You seem to lean into that, kind of, being controversial. Again, is that a strategic decision...?

Nathan Latka
I mean, 100%, it's biology. I mean, if you remember, guys, from chemistry, the one thing you learn is every force has an equal and opposite force. And if it doesn't have an equal and opposite force, it doesn't exist, because mass is neither created or destroyed. So, for you to create a movement and a massive audience of lovers, you have to have an equal and opposite opposing force of haters. If you don't, you have nothing. So, it's really important you invest in building both at the same time. You can't just do one, it's a marketplace model.

Todd Chambers
So, in the beginning, when you were starting the podcast, I'm sure like everybody you started off slow, you barely had any people listening to it. Like, how long did it really take you to, to kind of, make a success of it. Because you seem like someone that just grinds, you seem like a real worker. I mean, you put, like, one podcast a day. And you know, we struggle to get one every couple of weeks. So, just, how hard was that to get the thing going in the early days?

Nathan Latka
You have to love it. I mean, we just recorded our 3,035th episode, you can't do that without loving what you're doing. So, you have to love it. Early on, when I launched the podcast... I hustle and I grind, but I also want to be smart. And so I said, "what can I do to incentivize people to share the episodes early on? So, we had, I basically recorded 60 episodes before we went live, and then emailed everyone and said, "hey, I'm only picking 10 to go live on day one, for you to claim a spot, just reply back to this email and say that you're willing to promote your episode to your email list". So, the first 10 that said yes. We had almost 3.1 million emails going out in the first week promoting the podcast. So, we actually went from nothing... It might have been the fastest show ever to go from zero to a million downloads, it took about two and a half months.

Todd Chambers
Super smart. And actually, I learned that from you as well, I can't remember, I was listening to a piece of your content about the podcast. And now, when I'm thinking about guests, it obviously makes sense to leverage someone that already has an audience, and someone that's willing to be there to help you promote it, right? So, yes, super smart move.

Nathan Latka
This is hard to execute, because this comes down to empathy. You can't do this in such a direct way where it pisses off the person, right? So, you have to sort of say it in a way that's non threatening, and it sort of, like, both sides can win. and getting the art of, like, that statement correct is not easy.

Todd Chambers
How did you get people to be so transparent about their revenue? I mean, like, you can pretty much ask whatever you want and, you know, people are willing to answer. How difficult was it to get people to sign up to that in the early days? I mean, now it gets easier because you have a big audience and it's you know, there's value in it for them. But in the early days, how did you achieve that?

Nathan Latka
So, it didn't start this aggressive. It got more aggressive when I realised it was working and working for me was defined as number of people listening and how long they listened for, and how many subscribers and reviews. But I mean, we now, you know, to a couple of weeks ago, Vivo exited to Build.com for 2.4 million. Alex being one of the co-founders of Vivo came on my podcast a day before the announcement - that's crazy! Usually CEOs if they're about to sell, if they're gonna sell tomorrow for $2.3 billion, you think they're doing media interviews the day before that could jeopardise the sale? Heck no! But we got the interview, right? And now that's like a piece that's doing very well on YouTube because of the context of when it happened. So, a part of the reason a lot of CEOs come on my show, is they actually want to talk about the numbers. Yeah, right. But their board sometimes doesn't want them to. So, I'm their excuse, they can just tell the board. "Look how hard he push me on the show, guys, I had no choice, I had no choice"! But the entrepreneur wants to talk about the revenue and valuation, they want to talk about their story. So, it's a lot of fun.

Todd Chambers
So what else are you doing? So, you have the podcast, you've also written the book, you have your own fund, you have a subscription to, you know, all the data on the SaaS companies, like, what are the main kind of business ventures you have? Right now?

Nathan Latka
The biggest question I got once we published our 1,000th episode with Nathan, on the SaaS Founder; "I'm trying to scale from, you know, one to 10 million in revenue, which episode should I listen to first?". And there wasn't an easy way for me to answer that. So we've we built GetLatka.com to basically index all the audio data. So, every time a CEO said our last round valuation was 6 million, we pull out 6 million we put on our company profile and underline it. So now, you can go to GetLakta, click any data point and hear the CEO explaining why churn was 6%, the number one growth tactic they use to go from one to 10 million in ARR, Why Guillaume paid each three founders $444,000 last year, $100,000 base and $32,000 in dividend payouts, so, it's all linked up. So, GetLatka came because that's what my audience wanted. And then what happened was we started getting SEO traffic and people said, "do you have more data, I'm willing to pay for it". So we launched subscriptions on GetLatka, and that's sort of how that got going.

Now, the book was totally different, the magazine was totally different. The book happened because publishers would put their authors on my show during book launch week, and they would see how much I moved them up the Amazon rankings. And it was always a massive impact. So they knew I could sell which to all publishers care about. And, eventually, I was able to run a bidding war to get a great book deal to publish my own book. And now, anyone listening, right now you can find that, the next time you go to the airport, on the airport sort of Hudson bookstores.

Todd Chambers
Tell us about the book!

Nathan Latka
It's... I mean, have you seen it?

Todd Chambers
I haven't read it. I've read a few summaries of it. And I've heard you talking about it.

Nathan Latka
Yeah, summaries are great. Yeah, look, the book is really a collection of short stories. My thesis was, people need to be able to get the book, open it to any page and see a headline or a screenshot that interests them, read two pages and get value. So, it's a collection of a bunch of ways I generate a revenue built stuff between ages of 19 and 29. And the book is called "How To Be A Capitalist Without Any Capital". And so, you know, my goal on that was just to get to the Washington Journal best-seller list. We sold about 7,000 copies in the first week and hit it. And now, you know, we really enjoy it, right, folks buy it, they take pictures of themselves reading it, they tweet it to me, etc. We just passed sort of 30,000 sales, and the book is what ended up driving the magazine growth. So you know, I'm happy to dive into that. I think it's interesting, but the magazine is actually... I copied the magazine idea from Russell Brunson and ClickFunnels, you know, they've bootstrapped to 100 million bucks plus in revenue, he built this genius funnel to recover CAC, like, the instant that the first checkout happened. And that's what I'm doing with the magazine.

Todd Chambers
Interesting. Yeah, tell us about the magazine.

Nathan Latka
The magazine started off, as you know... Here's what it looks like, right? It's highly focused on SaaS. Now, this whole thing is generated from podcast transcripts, right? And then, what we do is we will then print off inside, essentially, a list of all the data, like, we'll list the companies, the valuation metrics, the revenue, the funding round, etc. But it started off as free if you pay $8.99 shipping, but now what we do is, you can buy the magazine, it's 29 bucks. So, I think it's the most expensive magazine out there. I don't know that I've ever paid that much for a magazine. But it's because I saw people getting the magazine at conferences, and they would go in and open and they'd circle companies in the list that they wanted to go meet or follow up with. And like, "oh my gosh, in the magazine checkout funnel, I should upsell the excel file with the data". And so our average checkout value now on nathanlatka.com/magazine is about almost 550 bucks per checkout, because of how the funnel works. It's a very profitable funnel, and we use that to then go up, so, you know, the other stuff we're working on.

Todd Chambers
Something that strikes me about you, Nathan, I think, this is maybe, I don't step out of line here, It's more, like, the American way. Your book is, you know, about capitalism, but you, and you said it in the beginning - you like money, right? Is that the thing you think that really drives you? Is it, like, you're just an ambitious dude, just under the skin? Or are you like really trying to become a billionaire? Like, what drives Nathan Lakha, you know, to do all this stuff and to hustle every day?

Nathan Latka
I mean, I will build a amount of wealth that I think will surprise even your listeners today. Just give me enough time and it will happen and they will read about it and they'll go, "I remember when Todd interviewed that guy and he said it, and look, it happened". So, it will happen.

But I will tell you - money is not what drives me. Competition is what drives me. I absolutely love competing with the best, the brightest, the smartest in any space. You know, if I wasn't interested in business competition, I would be playing games all day with friends, because it's a board game, you compete, I'd be playing flag football on the park drillfield here in Austin, Texas, I'd be playing power grid, right? So, I just love competition. And what I see business as you are picking a competition you want to play when you pick your market. And whenever you're selling the rules are established, the first decision you have is, do you stick with the rules? Or do you break them? Right? The second is, you know, once you sort of copy what already exists in your market, what unique twist can you add that no one else can replicate? And then, how do you win? And the measuring thing in businesses is money. So, that's why I look at money.

Todd Chambers
Gotcha. Do you break the rules?

Nathan Latka
I mean, I don't think any PR firm working with a podcast host would ever advocate for the podcast host to mark themselves as the most sued podcaster - but I guarantee you, your audience is listening right now going, "this guy's really the most sued, what, that, why is he getting sued? I want to go listen", right. So, you know, I guarantee you, no one's ever paid a major media outlet to write a negative article about them specifically to give their haters something to share on social media - you know, where the headline includes the word "con-man" to really make it feel real. This trick has worked on some of the brightest minds on Twitter, they don't even realise what I'm doing to them. It's incredible. So, yes, I mean, we're breaking all kinds of rules.

Todd Chambers
This is what I'm talking about! You seem to lean into being controversial, but like, for me... I get it. It works, totally, it's working for you, and, like, you know, kudos to you. But I can imagine a lot of people saying, like, on a personal level, they maybe wouldn't like, you know, getting Twitter storms, you know. I'm actually not personally on Twitter, but kind of that negative... Like how does that kind of impact you, you know, personally?

Nathan Latka
What I need smarter enemies. I wish these people hating me on Twitter were better at it. You want that equal and opposing force. Your CAC to get a hater is cheaper than your CAC to get a lover, right? And they both listen. And if my revenue model is sponsors, I just want them to listen. So, it's cheaper for me to get more people hating me. Howard Stern signed a half billion dollar deal with Sirius based off people listening because they hate him, right? There's nothing wrong with a strategy. The problem is most people aren't tough enough to deal with haters, right?

So, you know, I stand for something very specific, which is... VC backed founders have TechCrunch, bootstrap SaaS founders have Latka. That's who I celebrate. That's who I love, that I promote. You know, I retweet people when they get their first customer. And so, I will always fight for that, which means I will always hit VC backed founders very hard, like, on my podcast, and many times they don't like it, because they're used to having Forbes and TechCrunch bow down to them and their $20 billion valuation, and I won't do it. That's why it's controversial, but it works.

Todd Chambers
So, it does very much seem like going back to my question before, things seem to be driven by money. And you're like, you could see your instant response was like, yeah, "you just wait and see". But like, why? What is it that drives you? I mean, you said you want to compete, but like,do you really need to build the biggest buildings, do you really need to have all this wealth? Like, really, like, what, why, especially at the expense of what I just said...

Nathan Latka
It's the same reason I do the podcast, which is competing. On it with this sort of structure, I'm learning faster than anybody else - I can guarantee it. There's nobody that's learning as fast as I am in SaaS, there's no one that's interviewed 3,500 SaaS founders daily, you know, for five years, I just, I'm learning extremely fast.

So, to answer your question, it's not about building the biggest building, it's about saying, "I'm gonna write a book and try and sell more copies than Ryan Holiday's last book, because I'm gonna love the process, I'm gonna frickin' love the process". The only way you can do what I'm doing is you have to love the day- to-day, right? And I do. I know that if I go, say, "I want to go roll up the most mobile home parks", even if I don't roll up the most mobile home parks and beat Sam Zell, the process there for me to learn is driven by the competition. And I'm going to learn and retain better because of that dopamine that I get from the competition.

Todd Chambers
you must have learned so much, like you said, you've interviewed 3,500 people. I mean, take the business and the money aside, like you said, just the personal development of just speaking and interviewing so many smart people, like, man, you must have learned a bunch!

Are there any things that like really stick out now? I mean, have you kind of tricked, change the way you do business or, like, one of the key things that you take with you over those 3,500 episodes? I know that's a really big question, but is there anything that kind of sticks out?

Nathan Latka
What I've learned the most sort of doing this is how to build rapport quickly. Right? We don't do pre-interviews, we don't do any context setting. It's literally on 15 minutes on, you know, I'm asking very personal questions to strangers. What do you pay yourself? What was evaluation? What's your revenue per employee? What's your churn? Like, you have to just get very good at really caring about people and listening very intensely for the full 15 minutes, so that you can build enough rapport quickly to ask these very intense questions. That's really the biggest thing. By the way, if you're curious, the hardest founders to do this with are ex Israeli defense, they are those founders. And by far the hardest to quickly build rapport with and then ask, you know, intense questions.

Todd Chambers
So it's just like a cultural thing?

Nathan Latka
Well, they're trained when they go to the Defence Forces, how, like, interrogation techniques, which is essentially what I'm doing on the podcast, but in a smiley way, with my Nike hat on, in a very, hopefully non threatening manner.

Todd Chambers
I'm not sure anyone's watched all 3,500 episodes, but I'm sure a lot of people follow you. And I've seen a few, I've seen some pretty icy episodes... And sometimes I'll watch some of the episodes, and I'm like, "did this guy really know what he, or this girl, you know, really know what they're getting themselves into?". It's like, they seem to come on, they have their coffee, they're nice and relaxed, and you're like, bang, right? Let's go in there, like, Jesus! It's like a train hit them! Do you think people, do you think often people don't prepare for the them, or?

Nathan Latka
I have no remorse for people that don't prepare. I mean, for your show, I listened to Guillaume's episode, I listened to the ActiveCampaign episode, I'm prepared. And your episodes are longer than mine, they're 48 to 50 minutes, you know, each of mine takes 15 minutes, or even just scanning the iTunes reviews to understand it's been the same format for five years. So if you come on my show, and you have no idea what you're getting into, that just makes it more entertaining, because people go, "I wonder if this person knew what the heck they were getting into"!

Todd Chambers
Another thing that strikes me about you as well, and, Nathan, I'm sure a lot of people are thinking this... You seem to always be on? Like, I don't know, you seem to be one of those guys that's just blessed with, you know, you wake up in the morning, and you just like, go. And, like, you're just one of those guys, where your brain is just always on, it's always working. I don't know, you just seem to be like, have that natural, kind of, like, sharp brain.

Nathan Latka

I mean, like, I think thinking is, like, sort of a beautiful thing to be good at. And so, I'm always thinking, I'm always interested, you know, I'm always sort of learning. But look, I mean, you come meet me in person, and I'm a big teddy bear. Right? We'll go on a beautiful hike for two hours. You know, you'll see quickly, you'll learn my schedule. I was at a Mastermind in Mexico last week for a week and everyone was very surprised that I took an hour and a half long nap every day. They're going, "I thought you're always on I thought...". Oh, I get eight hours of sleep. And I take an hour and a half long nap. I'm always very well rested. So yeah, I'm always on. But that doesn't mean my calendar is packed. I'm actually trying to get closer and closer to a blank calendar.

Todd Chambers
Gotcha. So how the hell would you get close to a blank calendar when you do a podcast every day? Do you, like, batch them and do five a day - dude, how, like, does that work?

Nathan Latka
So, it's extreme batching. Two days a month, I will do 30 episodes back to back. So record 60 episodes each month, which means I'm always building my buffer, because you're only recording 30 right, or publishing 30. We're scheduled out, now, like... I could die today, you'll still get Latka greatness for, whatever, seven, eight months, whatever our buffer is, I don't know what the buffer is right now. But it's many months, so, it's extreme batching and a lot of coffee, and I just do 30 back to back 8am to basically 6pm two days a month.

Todd Chambers
Wow! Okay, that is really extreme batching. I guess the advantage of that is why you probably get in a bit of a rhythm and you get in the zone. Like, if I do a podcast and then, like, I do one three weeks later, I'm like, okay, and I'm out of the zone, where you're just like bang, bang, bang, bang. So is that an advantage as well, I guess, a huge advantage.

Nathan Latka
That's exactly right. Look, most of the people listening right now, you lose most your productivity based off switching costs. The number one easy thing you can do to get more out of your life, whatever you're trying to accomplish is to stop switching so much. Turn your phone off, focus for receiving, just focus for an hour with no distractions, and then do two hours and then do six. So that's what I'm doing.

Todd Chambers
Yeah. And by the way, that's, like, exactly a problem I'm trying to solve right now. Just the constant Slack messages, the constant e-mails - the switching cost is is real. Yeah, you just have to block everything. You have to prioritise your time, you have to be able to say no, and just have to be able to block out distractions. And I guess extreme batching is a good way to do that.

Nathan Latka
No, that's exactly right. You nailed it.

Todd Chambers
Okay, so, what about Founderpath? It seems like your mantra was that you don't necessarily need to take funding and that was kind of the whole story behind Guillaume at Lemlist. And that's kind of what, you also had that negative experience early on, but now you also have a founder fund. So how do you, kind of, align those two things?

Nathan Latka
Well, I wish I had Founderpath when I was building Heyo... So, when I had scaled Heyo to $60,000 a month in revenue, if Founderpath existed, then I could have gotten about $350,000 of cash from founder path by turning my monthly recurring revenue into upfront cash without selling.

Todd Chambers
Yeah, explain how that works.

Nathan Latka
It's factoring. So, to anyone listening right now, if you even, if you have as little as 1,000 bucks a month in revenue all the way up to, we have companies that you're just doing a million a month in revenue, but you can take a monthly contract for 100 bucks a month... We'll buy it so the annual value is 1,200 bucks. We'll buy it from you at a discount, so something between $1,000 The full $12,000 value, and then you get that cash today to go invest in Todd, right, and PPC services, right, to see if your ad spend has been working, and then you pay it back over 12 months. So this, I think, our plan, I mean, I think we'll invest billions of dollars into SaaS companies. But it's not a VC, we're not taking equity. There's no board, there's no board seat. It's literally just converting your MRR to upfront cash.

Todd Chambers
Gotcha. And how is that going? How many companies have you invested in today?

Nathan Latka
Yeah, no, it's a good question. So, we launched the tool back about two and a half years ago, as a way to help founders understand their data. And what happened is founders started asking me, "Nathan, can you help us raise debt capital or equity capital or anything? Can you help us sell?". So, we did almost $20 million worth of deals in a sort of marketplace model like this is high touch, a lot of my time, but it was working. And what happened was, I said, "you know what, instead of selling these deals off and helping these founders go raise from other providers like Lighter Capital, Espresso, SaaS Capital, Timaya, Hercules, SBB, etc. I should just raise a fund and do the deals myself". And so that's what we did.

I put up a million of my own cash many years ago to test it, then ended up raising a $5 million fund. Now we've raised much significantly more than that, you're actually going to see an announcement here very soon that's a multiple of that. But let's just say we're well on our way, we have over 2,000 - to answer your question directly - over 2,000 founders that have connected to the platform directly. So, Plaid, Stripe, because, they want our free reporting. And then, of that a portion are actually taking capital, but, currently, there's over $276 million of approved receivables. So, that's the amount of capital founders could get on our platform if they wanted. If they push the button - approved. And we think we'll hit a billion dollars invested in this form, you know, by 2023.

Todd Chambers
Is that high touch, is that where the majority of your time is spent right now?

Nathan Latka
No, it was high touch. Founderpath was built to make it no touch. Yeah, founders now can log on Founderpath once a week, and they take more money every week.

Todd Chambers
Wow. Okay, interesting. So, where is the majority of your time spent right now?

Nathan Latka
Honestly, most of is spent on reading. I just got done reading a book called Mastermind, which was by this guy named... It's a documentary, essentially on this guy named Paul Le Roux, super smart entrepreneur from the States - but then turned into sort of a drug lord and criminal. I'm now reading "House of Morgan" so that I can understand how the banking industry was built and see if there's things I can do with Founderpath, should we open a bank for bootstrap founders, you know, a lot of bootstrap owners listening right now, maybe have 2 or 3 million in revenue, you know, they go try and buy a house. And the bank won't lend to them because they don't have a historical pay stub, but they're rich in terms of equity and cash flow. Well, what if we launched a bank that can be personal bank for bootstrap SaaS founders, right? These are sort of the things that I'm thinking about today.

Todd Chambers
Gotcha. What's your favourite coffee, Nathan? If I if I had $1 every time I see you in a video, you're always drinking a coffee, man. But what do you get your coffee, like, are your a big coffee lover?

Nathan Latka
Yeah, so, unfortunately, I like supporting local brands, but Starbucks is close. So, this is, it's the Venti Pike Place with extra cream. I always love holding a coffee, I just, I don't know. It's like, I love coffee. So, if I'm dealing, if I have a sweet tooth in the afternoon, I need to pick me up, I'll get, you know, a Grande Mocha with whip from Starbucks. I'm usually drinking two or three coffees a day.

Todd Chambers
The American style coffees are just so God damn big!

Nathan Latka
Oh, your coffee is much better! European coffee is much better than American coffee.

Todd Chambers
Yeah, I mean, I'm biased, but I agree! Way better.

Cool. So, what else is in the pipeline, man? So, is it just more of the same, or like, yeah, what else is coming up for Nathan Latka?

Nathan Latka
We are hyper focused on celebrating bootstrapped founders. They just, you know, it's ridiculous that TechCrunch promotes these headlines - look, TechCrunch should be liable for the billions that WeWork took from investors, because media outlets with reporters who didn't ask the tough questions built WeWork when there was no real business. If they ask the real questions in these headlines... These outlets are in the bags of VCs, they have to propagate the story of go raise capital. That's what success looks like. And these outlets, The Wall Street Journal, Forbes TechCrunch, they also don't want to hit the founders hard because they want the next interview with the founder. See, I don't want to be friends with my guests. If I end up friends great. I just want to capture the story.

So, my focus today is on celebrating bootstrapped founders who are crushing it - people like Nathan Barry at ConvertKit, who gives dividends and rev shares to all of his employees and team members, broke 25 million last year, Guillaume, who you guys can go listen to on Todd's podcast a couple episodes ago... There's so many companies ran by great bootstrapped founders. And so, what I'm focused on now is building more media assets around this space. So, we have the magazine, we have the book, we're doing the Latka 1,000 SaaS Award Show in Austin, Texas on September 10, which will be an incredible event. It'll be a beautiful awards event celebrating bootstrap founders. And then I'm focused just a lot on Founderpath, right? How do we raise a larger fund at a cheaper cost of capital so we can pass those savings on to bootstrap founders, and we're going to avoid going out and competing. And there's other people in the Founderpath space that have raised gobs of capital - but they're diluted like crazy, they're very distracted, they're not focused on bootstrap, SaaS founders, and we're gonna win that space by hyper focusing on bootstrap SaaS founders.

Todd Chambers
Love it. Maybe on that note, then, for, you know, bootstrap founders listening, the same question I asked Guillaume as well, considering his experience; What advice would you give to, you know, bootstrap founders, that want to start a SaaS company? It's like, you don't need money... Yeah. What would be your advice to those people?

Nathan Latka
Yeah, focus on revenue per employee, the best business is a one person show doing, you know, 10 million in revenue, right? If your competitor has 100 people and 10 million in revenue and a big valuation, he gets a TechCrunch article, you're still way more successful than them, right? Revenue, more freedom, revenue per employee... So focus on revenue per employee. Valuations do not matter. Unless they eventually one day become a liquid in the form of a secondary, or your, you know, someone's buying you. But you have to remember, the higher your valuation, the less likely buyers you have, because they have to come up with more money. So, it's much better to focus on building a $5 million SaaS company with 2 million in profits than it is to go try and raise a billion dollars, and raise, and build a $5 billion SaaS company that you can IPO in 20 years, maybe.

Todd Chambers
Really, really good advice. Something else, I listened to you, I think it was SaaStock. And you were talking about how many agencies convert into SaaS companies, And I was like, for me, I feel like, because, I mean, we run an agency, right? The growth of the agency is highly dependent on having more staff. And it's like, it's great, so for me, it was kind of like, "oh, yeah, you know, maybe we should be thinking about... I mean, we learn how to market SaaS companies all day, every day, like, so we're pretty good at that. So, I'm thinking, that's probably a pretty good, good move for us. But has that been an observation, you found tons of agents seem to start their own SaaS companies?

Nathan Latka
well, not tons, but the most successful SaaS companies, this is how they're built. They honestly... You potentially are the next billion, like, you know, next, you know, call at $20 million revenue SaaS company that's highly profitable. Because you are working with a lot of clients right now. You are seeing the same problems across, like, how they manage PPC, and you're going to think of tools to invent for them. And one of those tools that you start building internally will eventually, will spin out as your own product. So, I'm very bullish on that model. I think you're in a unique position to do that. How, out of curiosity, how many folks do you have full time right now?

Todd Chambers
Nine.

Nathan Latka
Okay, got it. Interesting. And it's pure agency model, so you're essentially just sort of trading time for money, right?

Todd Chambers
Exactly. So, we build their own frameworks and things, but it's just retainers and, and yes, selling our time, effectively, which we need to move away from. But pure agency.

Nathan Latka
But there's nothing wrong with that, like, to build up a nice little cash thing. Because look, there are a ton of individual SaaS tools in one of your spaces. So like, you guys are helping folks with paid media paid, social customer research, copywriting conversion, optimization, analytics measurement, I can literally name 20 SaaS companies in each of those six service categories that you're currently delivering. And the playbook, if I was you, would be to go out and buy a company in one of those six spaces that you're delivering services in, sign up your customers to that SaaS company, and that's going to get you more growth quickly. And then you're going to use what you know about building a SaaS company, because you're doing it for others right now to grow that thing. And that's, you're going to create a lot of personal wealth for yourself. That's my personal opinion.

Todd Chambers
Nice. I love the idea! I didn't think of that one, buying a SaaS company to get myself, yeah, kind of take that big jump instead of building something from the ground.

Nathan Latka
And it doesn't have to be expensive. I mean, you know, there's great deals there. There are several I know right now that are doing maybe 500,000 bucks in ARR, that you can, you know, you can buy them for one to 2x revenue, if you understand and to get to the founder and in the right way and set it up properly. So it doesn't have to be expensive.

Todd Chambers
What about agencies? I always... This is a thing that I always come back to, is like, what is the end-game for Upraw Media? I... Funding and selling companies is not my expertise. So I'm always like, you know, at the end of the day, am I ever gonna be able to sell Upraw? Am I gonna have to hire somebody to take it over? What is your two cents on that, you see many agencies sell?

Nathan Latka
Yeah, the sale price on an agency will be somewhere... Currently, there's between sort of one and 3x EBITDA, it's a lot of hustle. If I was running agency today, what I would be doing is using it to get personally wealthy, so that I could invest in a dev, co founders, CTOs or dev shop to build a SaaS tool. So, like, I would be, for you, focused on how do you build personal wealth from this, and also maybe pay dividends out to the team. So, you can eventually pivot into a SaaS company, or if you want to sell, you know, so, if you keep doubling down on the media brand... Like, what you're doing with the podcast and build other media assets, you could end up in a position like The Hustle or Morning Brew, right, where Hubspot is buying The Hustle or the media business, right? Because it's a moat for them. You could see a SaaS company maybe like Supermetrics, right, by, you know, you're close to those guys, you work with Mikael, you had him on as well. They could end up buying you, because you will then be their media personality, and you build a media business inside of Supermetrics - and they'll pay a premium for that.

Todd Chambers
Yeah, it's super interesting, the whole media piece. Because, like, a lot of people aren't really willing to put the work in for, like, a podcast, because they want the immediate returns, right? Like, full transparency, this is like, what, the 17th episode or something. I mean, yeah, people come to our website and it adds a lot of credibility that I'm having these types of things. But I haven't had one person say, "oh I found your podcast on Spotify or on YouTube and then...". Like, that doesn't, that hasn't happened yet. Like, you have to play the long game, right?

Nathan Latka
Don't get discouraged, stick to it for two years - at least.

Todd Chambers
200 episodes is the goal.

Nathan Latka
Yes stick to it, no matter what. Even if nobody listens, because there are compounding returns over time, I can just tell you there are compounding returns over time, and you're doing a great job - the content is great, the guests are great. I know sometimes you're getting, like, the VP of marketing, sometimes it's the CMO, sometimes the CEO - if you really dominate, like, one position group, you will be the go to source for every SaaS CMO and, with that sort of monopolisation of that specific niche, it allows you to have pricing power with sponsors that want to reach just CMOS, or if you want just SaaS, then you can sell it to CMOS. You have pricing leverage there because of the media asset.

Todd Chambers
Yeah, great advice. Cool! What, let's, let's kind of close up, so, what do you do in your personal time? What are some stuff people don't know about you doing in your personal time, you know?

Nathan Latka
I always have a bag of almonds next to me - I'm always eating almonds.

Todd Chambers
Salted?

Nathan Latka
Oh, no, unsalted - bad for the skin! Bad for the blood, bad for the skin. So I'm always doing that, you know, I'm working out once a day, and I'm using WHOOP to track all of my personal metrics. I'm experimenting with creatine, I do that. I think, like, I don't have veins yet, but I really want, like, veins and muscle. So, I have a little bit, a little action, right there. But I want more, I want more veins. I'm running a lot. The reading that I'm doing these days are, you know, sort of, they're sort of, they come off as sort of, like, scammy books, but, like, you know, "Writing Riches" Ray Edwards, these are very helpful with copywriting stuff. What else do I do in my personal time? A lot of board games, love playing board games, playing a lot of poker.

Todd Chambers
Nice! Where do you, where do you play poker?

Nathan Latka
Just home games. The beautiful thing about poker, I'll tell you this, because I think this is not why most people play poker. You win in poker by doing nothing. Like, if you can default to doing nothing, you'll generally win. Most people lose in poker because when you're six hours into a session, you're bored and you just start playing hands you shouldn't play. So, there is no better practice for me from a business perspective than going to a poker table and teaching myself to sit there still for eight hours and fold for eight hours straight and do nothing. That's what I'm practising is doing nothing and that sort of focus and like stability is what enables me to then go take bigger risks elsewhere in life.

Todd Chambers
That makes sense. Totally. And you mentioned Ryan Holiday there. Are you a follower of stoicism at all?

Nathan Latka
So, I haven't read his stoicism books, but I'm a big fan of just Ryan in general. You know, he's dedicated to his craft. He doesn't care what other people think, from what I can tell he was helpful for me when I was writing my book, which I appreciated, He owns goats, which I love. And he's here in Austin, Texas.

Todd Chambers
So nice. How is how is it in Austin, Texas? You were the first states in the US to just, like, say "fuck it, let's just open up".

Nathan Latka
Yeah, we're I mean, by the way, I'm trying to get more international travelling. So, I went ahead and got my my my Pfizer double vaccine there. You know, it's open, I mean, nothing's - no masks inside. It's pretty much life as back to life as normal, which is why we said you know, we're going to do our first live event in September. We did a pre-sales, we had a lot of people purchase pre-sale tickets, so everything looks good. I think it's probably still pretty closed up over there, right?

Todd Chambers
Oh, this is the zombie apocalypse here. It's - I'm looking at the window now - it's rain, hammering, it's like, June and there is rain hammering against the window. It's pretty much still... restaurants aren't open, it's masks in the office here. It's pretty doomy.

Nathan Latka
I mean, I'm gonna go to Equinox later here in Austin and work out with no mask. You know, I'll probably, you know, just go into sauna with my protein drink and relax for 10 minutes. There's no masks in the sauna, which you know, COVID in the air. I mean, sauna is like the last place you want to be if you're worried about that, but most people are back. I mean, most people are vaccinated. I think that's, you know, the Biden administration has done a good job rolling out those vaccinations.

Todd Chambers
Yeah. And at the end of the day, listen, we have to be grateful for what we have. And you know, I can't complain about you know, lockdown, I feel blessed for the life I live, so, I mean. Yeah, the bad times just make you appreciate the good times.

Nathan Latka
Yeah, and Todd, you came onto my radar like a frickin rocket. You know, many months ago, I'm really bullish on what you're doing. I appreciate what you're doing for the SaaS world. And man, I just hope you stick with it for the long run. I think you've built something really special here.

Todd Chambers
Thank you so much for your time, Nathan and yeah, let's speak soon!

Nathan Latka
All right, thanks.

Todd Chambers
Thanks for listening to the podcast, guys. for links to any other resources, head over to https://uprawmedia.com/blog. And, super important, please let us know how we're doing! Check the links in the description where you can leave some feedback or you can just email me todd@uprawmedia.com. 'Till next time, adios!

Transcribed by https://otter.ai