How Nathan Latka Uses His Podcast To Become An Investor In Tech Companies

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All right, welcome to Bacon Wrapped Business. This is Brad Costanzo, and today I've got a guest that I've been wanting to get on this show for a long time. I've been on his podcast a long time ago, and I've been waiting to return the favor and get to pick his brain on the show. Nathan Lotka is joining me here today. Say hey, Nathan.

Hello, Brad. How are you? You're totally lying. You just said I can have this guy on my show. I'm gonna wait as long as possible.

I'm gonna wait. I wanted to make sure that the show had enough. What do I say? Weight and cachet. To honor the great Nathan Latke now. So, you know, I want to introduce, like, kind of how we met and, you know, how we know each other. So I think I. I remember when you had the hey, was it, hey, yo, that was the software, right?

That's right.

Years ago. And we can talk a little bit about what that was and how you sold it, but I remember that. And then I believe our mutual friend Lo Silva made an introduction. And originally, I got to share my story and advice and whatnot. On your podcast. Maybe. Gosh, I think it's been a year and a half. Something like maybe a year ago. And then just recently, we reconnected at Steve Ulcer's was the New Media Summit. We were both icons of influence. I think I still got my badge somewhere to prove it to my wife. That, look, I'm an icon.

Didn't happen unless you have the badge.

Exactly. I did take a badge. I said a picture of the badge. I said, if it exists on the badge, it must be true. Yes, but, man, I've been really impressed with watching the stuff you've done, from selling hey, yo. To creating hey, yo. To selling that and going on to create a podcast that called the Top Entre. Is it the top or the top entrepreneurs?

Yeah, people can just Google the top podcast and it shows up at the top spot, but I guess the full name is the top entrepreneurs.

So I've never asked you this, but did you call it the top entrepreneurs for SEO or the top for SEO?

I Did it for se. I did it for SEO reasons. So when you looked at the search volume for podcasting in general about two years ago, you saw steadily increasing the search term for the top podcast going really quickly. And I'm like, well, hell, I'm just gonna my show something like that to take advantage of the swing.

That's awesome. Yeah. And I went the exact opposite way. I was like, let's get some. Let's get some crazy. Make it my business, baby. Well, speaking of our friend Lo Silva, who was also a guest in the show, and he's been one of my longtime friends, when he had a podcast, he said, hey, man, can you share this episode on Facebook? And I was like, yeah. So I just wrote something in the title that said, check this out. LOS just shared some bacon wrapped business advice if I've ever seen it. And I was like, that would be a good podcast name. So bacon rat business was born.

So did you then get into launching your show just because you respected LOS and had such a good time on his and you said, hey, if it's working for him, I should do it too?

Respected Lo who respects LOS that's why.

I'm asking him, who the hell respects Lois?

I can't wait to send this to him. No. So a bunch of my friends have been telling me that I should do it, and I never just wanted to come out with a Brad Costanzo show, because that was. It was. So when I did that and I saw the name, I was talking to my buddy Nate. I was gonna say Nate, Nick Unsworth. And Nick had me on his show, and I was telling him I was thinking about doing it. He said, well, what would it be called? And I said, bacon wrap business. And he's like, cool, you got the URL. I said, not yet, but it's available. So he interviewed me and he said, okay, so go check out Brad's new podcast@baconrapbusiness.com I was like, okay, I guess I've got to start this now. Nick, when does this show come out? And he said, 10 days. So I had 10 days to go from concept to launch, and it was just baptism by fire. So that's good stuff. It's been great. You know, it's been such a cool way for me. And I know for you as well, this is one of the big things I want to talk about to get access and influence in the marketplace. And you've really done this in a very big way. And in fact, when we were having lunch the other day, you even mentioned what did you say? I'm not even a entrepreneur or a marketer. I'm an investment banker. So you've kind of changed that around. And I definitely want to talk about some of the ways you're approaching deal structure and how you're using your podcast very strategically to build access and influence to some of the truly the top and especially tech entrepreneurs out there and creating the getlock database and some of the other stuff that.

Yeah, this will blow your mind, Brad. Why? Actually, I ran the numbers the other day because we've just passed our 1000th interview. Now we've only released about 700 of them. We have a thousand interviews, and altogether the CEOs, they employ 28,000 people. They've raised $6.3 billion, and they do $3.7 billion annually altogether. So, I mean, that gives you a sense. And then just to break that down into some cohorts. Right. So 20 of my interviews are with software CEOs doing more than 100 million per year. But then I have hundreds that are people that are less than a million in annual revenue that are just starting. So, I mean, it really runs the gamut.

Yeah, no. Absolutely no. When you got into the podcast, so tell me where you were. So, first of all, hey, yo, explain what the software did.

Yeah, the very quick heyo story. I was 19, in college, studying architecture. It was 09. Nobody is hiring architects in the middle of a financial crash. Nobody's building. That's the first thing to go. So I said, to hell with this. Launched heyo the software company, and all I did to launch it is I saw another software doing the same thing. I thought the CEO was a total deadbeat, not a good marketer, and said, you know, I'm just going to create the exact same thing and out market him. And I just crushed him. Right. So, you know, a year and a half in, you know, we were growing 30, 40, 50 grand in monthly recurring revenue. We then got investment from some of the world, actually, many would say the world's top angel investors. And David Cohen from Techstars and, you know, Dave McClure from 500 Startups and from other folks. And then I raised a $2 million round of funding. Once we grew to about 90 grand in monthly recurring revenue, grew that to about 5 million bucks in total sales up to the time when I was 25 years old and then sold it to our number one competitor. And so that's that. That kind of rounds out that whole story in 30 seconds.

Where'd you. Where'd you Go when you're in your early 20s, where'd you go for funding back then? Because a lot of people I know when I was in my early 20s, I knew where to go for happy hour, but I didn't know where to go for. To raise millions in funding.

Yeah. Well, so I never went out to raise capital. What happened was, as I started meeting just influential business people who asked me. Good question. I would ask a very simple question that I have to give myself some credit. I think, for my age at the time, it was like a genius thing to do. I just said, hey, Brad, I really respect you. Can I put you on my monthly update list where I send out all my private financial metrics on the business, and if you see something you can help me with or challenge me on, just reply back. If not, no need to reply, but at least you get free information. And now these people would say yes to that. So once they started getting these updates and I'm doing 10, 20, 30, they're writing back going, have you thought about investment? And I'm going, what do you mean, investment? How does that work? And then they have to teach me. Right. That's how it happened.

That's. That's amazing. And, you know, I've always heard that. And actually my friend Roland Frazier also said this on our show, on our episode together. But it's like, you know, if you want to raise money, ask for advice. If you want to get advice, ask for money.

Yeah. And that, you know, it's true, but you still have to be a little bit of an artist and you have to be a little creative. Because I meet so many people over lunch and they end with, so, Nathan, how can I be of service to you? How can I help you? It makes me want to vomit. It's like they read that tactic in a Vanessa Van Edwards book on how to captivate people. So they said, I'm going to ask it at the end of all my conversations because it's a strategic thing to do. It just. It doesn't sound good. So you have to ask for advice, but not make it seem like you're asking for advice for the sake of, like, a stupid question.

Right. And actually, I mentioned that exact same thing when we were on the panel at New Media Summit. And at the end of this show, I've got my own twist on that, which I'll ask you, but it's a totally different way, especially because I think that I hate that question. Hey, Nathan, how can I support you? What can I do for, like.

You know, why It's a bad question because it requires me to do work. It requires me to think of a way for you to help me. Because I can't just say, brad, you can't help me because it makes me sound too egotistic. So you're putting the work on me, and it's just not a good thing. You'll never hear from me again. If you ask me that.

No, we are 100% on the same page. I think I even did a podcast episode on this about how much it annoys me and there's a better way to do it, which we'll get to, dear listeners. But anyway, I love that, in a way, you were even asking them. It's almost like, hey, can you be on my board? But you didn't even ask for that much of a commitment. Can I just send you an update on my financials and everything else that's going on? I mean, who would really say no? I'm sure most people would say, yeah, absolutely.

Listen, the trick is money follows Mindshare. Whether it's an investor putting money in your company or customers buying your product, money follows mindshare. So you have to either create value in your product where users are getting addicted. That's getting mind share, or create intellectual conversations with potential investors that gets them thinking about you more. That's Mindshare. So focus on capturing Mindshare first. And the money becomes so easy, Brad. I mean, I have so much like, money comes to me now. I clap my fingers and boom, money is here. It's so easy once you do that.

Yeah. The biggest problem is probably just knowing where to. Where to deploy it.

Exactly right.

And that's a good problem to have. I'd rather have.

Yes.

You know, more money and not enough ideas. You've got a lot of investments that you're making, so. And as you said, you're. You're seeing yourself as an. More of an investment banker, especially with this platform. And you're taking. And you're taking. You're making investments, taking equity, doing some really creative deals, both with your podcast and with food trucks and with everything else. Tell me about some of the investments you're making right now.

Yeah, so. So we did an amount last year in terms of me helping CEOs raise capital and me helping CEOs sell their companies for great multiples. We did an amount, I think, that would shock most people, considering I have no banking background. In fact, I had so many emails coming to me from very large banks, their M and A departments, begging me. I mean, they would kiss my foot if I asked them to, to join their M and A firms, right? Because these are typical investment banking firms where they're making 3% of a sale price. If they sell a company for a billion dollars, you know, they get, you know, 30 million. That's their whole business. Right. What happened was the podcast basically allowed me to have 15 to 20 minute conversations with the really unbelievable CEOs. And after the interview would end, we'd have five minutes for my next interview where they'd say, Nathan, we're thinking about selling or we're thinking about raising capital or hey, we want to buy other companies. And I would then go to work helping them get the deal they wanted and they put all their business through me. And I just take a. I say, I don't, I don't even sign an agreement, Brad. What I say is, listen, I'm going to help you sell your company or raise capital or whatever for an unbelievable price. And we're not even going to sign anything. But here's what I expect. If you like the deal at the end, I expect a big, beautiful truckload of money in front of my house in a big shiny silver car. Right? And then I will give you more deals if you do that. So that's how I operate.

That's great. And then do you just. Then when you're raising the money, when you're helping them do that, you're doing that via your platform and your contacts and your Rolodex that you've developed through all that?

Yeah, it's phone calls and people I've connected with. You know, my podcast is a. It's a very, very sophisticated audience that listens. I mean, like for example, you know, the John Lee Dumas, entrepreneur on fire, even kind of Nick Unsworth, those kind of motivational kind of shows. That's not every. No, those people, when they listen to my show, they hate me. Which is fine. I'm a very metrics driven. I ask every CEO how much revenue they did last month, what do they pay themselves, what's their equity, what's their valuation, the hard stuff. And so I have very, very sophisticated listeners, like M and a people, CEOs of huge companies. I mean, the smartest people. So those people listen and then they reach out and say, nathan, I heard this person on your show. Can you set up an intro? I want to invest. So I've just started building, building, building that Rolodex.

That's great. As I mentioned those two words earlier, and it's a big part of the advice that I get, that I try to take myself and that I give a lot of people is that it's access and influence, the two hinges, the small hinges that swing big doors of opportunity. Because if you can get access, and access doesn't necessarily mean ownership, right? I mean, we're in an access economy. Airbnb, Uber, etc. And even capital, you don't have to have all the money if you can make a. If you have influence with the people who do. And you've done a really good job of using your platform to get access to influence and then build influence for yourself, which gives you more access to more people and more influence. And as I say, it's kind of like compound interest. And it's the sole reason I started my podcast. I didn't know where it was going to go. I didn't have any specific reason. I don't have a coaching program on the back of this where I'm selling things. I do consulting, I do investments, acquisitions as well. But my entire thing was if I can get the right guests on the phone and build relationships with there, there's a lot of opportunities that can open. That's funny. All of the really, really cool things that are going on in my business life are a direct result of this podcast and a direct result of treating it strategically and not just trying to fill up the airwaves with more, you know, two idiots talking about marketing stuff.

Yeah, I feel so bad when I listen to these people that launch a show. They've been doing it for three years. I listen to an episode and I'm bored as hell and I go, oh my gosh, I feel so bad for these people because they are just living in a delusional world. Like, yeah, maybe they have a million downloads, but that door that that's opening for them are to people that are broke and in debt. Like, I hate to say it, but like, I'm focused on opening doors where if the door gets opened, it's 20, 30, 50, 100 million dollar deals for me. Not a $10 person signing up for my info product membership site right now.

Are you, Are you making any. Are you personally making many investments of your own cash in some of these deals right now, or are you able to, you know, wield some of your influence and things in order to get equity without.

Yeah, there are some people that have wanted more of my mind share. So to get that, they have given me equity and I help them grow so fast and then raise at a much higher valuation. I have also decided to Write very large checks to other venture capital firms as a limited partner, and then I will recommend people who are interested in funding to those firms. So I invest. But in. But. But I'm not the one making the investment decision. It's my money, but someone else has control over it because I wrote a check.

And you handle all the. Yeah, all the other little administrative stuff. Diligence.

Yeah, exactly. Now the. The other aspect there is I am doing some deals myself, but these are more for entertainment purposes. Right. So the other day I walked with my checkbook down Rainey street in Austin and bought a random business on the spot that I didn't know. It ended up being a food truck called Ming's Funny Pad Thai.

Yeah.

Wrote her a $6,000 check. She pays me back 75 cents per meal till I'm paid back, and then 5 cents per meal in perpetuity.

That's a Kevin O' Leary deal right there. Mr. Wonderful.

That is. But it's great returns, right? And more importantly, almost. Well, 1.1, I think. Or maybe it's up to 1.3 million people watched my Facebook Live when I did that on my Facebook page at Nathan Latke. So that gave me the opportunity to teach over a million people about business and investing. It cost me a six grand check, which also helped an entrepreneur and also helped her grow. So those are more for entertainment and teaching purposes.

Well, it didn't even cost you. I mean, it was an investment that is currently paying you back.

I already got paid back. I'm already making money. I've already made, I think like 11% return on that in seven months.

That's awesome. Now are you buying any. Are you acquiring any businesses like majority ownership and trying to take full control over those? Because I know you got the top inbox and another one send later.

I did. Yeah. Those deals I did. I bought the whole company. Not made an investment, bought the whole company. And the reason I really like the top inbox.com is because it is a tool that helps salespeople send emails later in Gmail or auto follow up, which increases conversion and close ratios or even it allows you to see when your emails are opened. And so I use the tool back at heyo. And so when I realized there's an opportunity to buy it, I wrote the check very quickly, I bought it. And I have to tell you, Brad, it's growing so fast now. I mean, it's almost doubling quarter over quarter in terms of both users and revenue base.

That's amazing. And I'm a user of it.

Oh, good.

Yeah, absolutely. I love it. And there'll be a link to that in the show notes. I'll make sure that that's all available. How much did you. Do you have a team handling that? Like how much of your own time are you spent working and operating? I mean, what's your role there?

Yeah, I'm not a big team guy. Right. I don't like making people feel good and like all that.

I could never.

Yeah, I'm not a team guy. I just like getting stuff done. I like credit. Like, I like to know that if something goes well, my name's on it and I get credit. But also if it goes bad, you get all the shit. I'm really good at dealing with shit. Right.

So are you in there dealing with the shit every day? Like, are you. How much time are you spending running?

Those are very. So that company, let's. For the top inbox, I maybe spend an hour a month on that. And that's usually most of that time is our emails with the developer that I have developing on it.

Right. So okay, so. And then how many people typically does it take to run something like that?

Well, that one, I could release the developer if I wanted to stop making product updates and it would still grow about 6 or 7% month over month in terms of revenue.

So it's just the two of you?

Well, yeah. I mean, I don't have any full time employees. They're all like, what I do is I have all my systems built out in tasks and I then hire people for those tasks. And what I do is once the task gets going and I get in a flow, if I don't like that person, X is charging me 10 bucks to do that task. I will go make it competitive and find someone to do it at 5 to cut my cost in half because I have a lot of volume. So get the task laid out. Hire a person for the task to execute it. Once you get a volume play, then negotiate a lower price point with that person or go replace them with somebody else.

Are you doing much micromanagement of them, like the project management or do you have anybody to kind of oversee that? Report back to you KPIs and you only come in when necessary.

My biggest time investment is making sure the task is clear and concise at the beginning. That's my biggest time investment. And then after it. No, it just runs.

Yeah. Nice. Yeah. So I just bought a. I just bought a business a couple months ago.

Is the E Commerce one right?

Yeah, well, actually that one and I'll tell you offline about how that's kind of changed, but in a good way. That one's on hold. I'm not quite close.

Wait. Come on, Brad. Why you got to tell me offline?

What'd you do?

Did you walk away?

Because it's not. Things aren't done yet. Things aren't done yet. It is still being massaged and manipulated, however. All good. But the other one that I bought, it was a. It was a smaller website. It has a big audience, it's got some great opportunities. But then one of the issues that I noticed as I bought it, it's almost like getting a new Christmas toy, right? It's like, oh, you're excited to unwrap it, and then you realize that assembly is required and you go, oh, shit. So now I'm in the process of building, of bringing the people to handle those tasks. I've had to kind of zoom back out and say, stop working on this $10 an hour stuff, because. But sometimes you need to. Sometimes you got to roll up the sleeves and figure it out, okay, what the heck did I buy so that I can hire the right people? But that's not my strength, which is managing teams, project managing, and I love systems. I'm just not the best at creating them or following them. So I'm trying to learn that aspect as an entrepreneur and what I've been doing, what's been really cool about the acquisition I've done, the acquisition I'm working on, is it's forcing me to think more. Instead of like a business owner, I'm trying to think more like an owner of businesses and dive more into P&Ls and balance sheets and income statements and really understanding how the business runs from a investor level, as opposed to worrying about conversion optimization and EPC and all this other stuff, because that's not ultimately where I want to be. I want to be investing in more businesses using my influence, using my knowledge and strategies to help them grow without having to get into weeds.

And what do you hope the outcome is? You want to sell them or milk them for cash flow forever? What do you want to do with them?

The two that I'm working on right now is basically fix and sell, because I know I don't want to necessarily be in them for a long term, but they both got the potential for an exit. Maybe a small exit, maybe a big one. And it's kind of hard to say at the moment, but, I mean, look.

That'S my strategy as well, and it's one of the reasons I don't like hiring people because that's actually, I mean it can be a liability when you're trying to sell the company. But if you have a booklet of tasks that have to be executed, that's easy to pass off.

Absolutely. You know, one of my mentors had said, now he was a very, I don't want to say he was a, you know, misanthrope or just hated people, but he kind of hated, he hated employees. And he was always very much like everybody says hire a players. He goes, no, have A plus systems that you can plug in C players and you know, you can replace them when needed if your systems are good enough. Now that's true to a degree.

Here's what I'll say about that. It's 100% true that if you want to de risk your ability to hit doubles, and by double, I mean a four million dollar exit every two years, you should do exactly what you just said. A systems that you can plug anybody into. If you want to create the next Facebook where there has to be some innovative breakthrough, you have to design, create something brand new, you have to go the other route, which is agreed a players random but your chances of success are significantly lower.

Yeah, no, absolutely. And it also depends if you're trying to be really innovative, you need innovative minds behind that. If you're trying to buy cash cow, that's just, alright, let's get this in, plug the pieces together and sell somebody a business in a box. Different story. But you know, those are some of the things that I'm working on. That's one of the reasons I was really excited to talk to you today is because there's very few people out there who actually do think very much like a deal maker. And how can I, you know, how can I think a little bit outside of the box and put together really lucrative deals using non linear strategies? And you're definitely doing a lot of that. I was really impressed. Did you, when you started the top podcast, did you, did you have this in mind or was it like, no, I'm gonna start this.

I will never be the coach that looks back and said, oh, look how smart I am. I planned this from the beginning. What I do believe, what I do believe and I've always believed and you can go watch videos of me from 10 years ago. Momentum is king and so I know if the ball gets going, I will make good things happen. Now I didn't know this stuff would be happening, but I knew if I just got going and committed to it no matter what good stuff would happen.

Yeah, I love it. It's exactly what I did too. It's just get the ball moving and figure it out as you go. Because it's way too hard to just plan it like I, I can. I've never been able to come up with like a five year plan. What's your five year plans? I literally don't know. Because I'd be thrilled if my life and business is totally different in a year. As long as it's better.

Yeah, I mean, look, it's true. It's one of the issues I have with like these books that come out, you know, the one minute manager, blah, blah, blah, you know, Gary Keller and Jay Papa's on the one thing. Big fans of both of them. Really well done book. But it is the stupidest thing you could possibly do to focus on one thing. No, no successful person has ever focused on one thing. Okay. Look at Bezos. He's got his hands in so many pots now, right? And he created momentum starting first. And the second he had the ability to do it, he launched other balls in the air. So that's one of, I mean, that's one of the things I tell people all the time is you shouldn't worry about starting a bunch of stuff, you should worry about finishing. Right. So know when to end them. Know what? No. Ask yourself at the beginning, if this goes 100% according to plan, what's the most money I can make? And if that money doesn't start coming in in the time period you give yourself, shut it down and launch a different ball in the air.

That's also.

Yeah.

My contention with people who say never ever, ever, ever give up. That's terrible advice. You have to know, because those are people who don't understand opportunity cost and.

People that have a big ego that don't want the public to see them as a failure. So that's why they say never give up.

Yeah, I mean, never give up on trying to improve your life and go after you what you really want. But business ideas, etc. I, you know, one of the businesses that we talked about when I was on your show, the coffee business that I was doing with my wife, because of opportunity costs and because of some unforeseen things, I had to, it's still there, but I had to put it way on the back shelf because of that exact reason. The economics weren't working out. Opportunity cost was too big. And I just realized that this is never going to be, this is going to be a single. It's never going to be a double triple home run. And you should give.

You should shut the stuff down fast with no apology and as quick as you possibly can.

Right. Well, I was, it was funny. I was in a mastermind when this happened. When I made that decision and everybody just raised their drinks and toasted. It was a drinking mastermind, but it won't be your last. And it's kind of cool when you know that sometimes quitting is the exact right thing to do.

You have to swing the bat to hit home run. Swing, swing, swing.

Who do you go to for. Who do you. Who do you turn to for advice right now? Like, who are you? Some of your most trusted advisors? Mentors? I mean, maybe we don't know them if we don't know their names. You can, like, in general, who they are.

Well, you have to be very careful with advice because even a billionaire giving you advice is coming from a very different perspective. And that billionaire probably doesn't remember the actual steps they took when they made their first dollar to teach you. And even if they did, it might not be relevant today. So I. What I do is I go hunting for patterns, right? I go hunting for systems and patterns. And so I don't like to get that in the medium of people talking to me, like, over coffee. What I like to do is go read biographies and pull the pattern. You know, read a biography about Warren Buffett on commerce one day and the next day on Walt Disney about creativity and pull the pattern from both, both commerce and creativity and build that pattern into your business.

I love that. Okay, so you don't. Yeah, you'll go to the source material and you'll. As I said, I try to do that as well. And you get a lot of insights over that because. Yeah, a lot of the context can be lost in just conversations. People giving you advice on, well, this is what I would do. And they don't even know the full picture.

Yeah, a lot of people think you're making someone feel good. A lot of people actually.