131: $60M Exit, $526M IPO, and Using AI to Scale with Joe Stolte

Today, I’m joined by Joe Stolte, a serial entrepreneur, growth coach, and the CEO of Daily.ai, a company that helps brands publish AI-powered email newsletters that generate 40-60% open rates without writing a single piece of content.

As a program manager at Microsoft in his 20s, Joe was making over $250,000. But as an entrepreneur at heart, he knew he couldn’t ignore the call to go out on his own. After his first attempt at raising outside capital left Joe $37,000 in debt, he learned from his experience, going on to found 5 companies and exit 3.

Joe is also a former Inc 500 entrepreneur who helped create a $60M+ exit at GrowFlow, helped take Lottery.com public at $526M, and helped grow Tractionology Group to producing $44M in client revenue in 3 years.

In today’s episode, you’ll hear Joe’s firsthand experience about the pros and cons of bootstrapping vs. fundraising. You’ll also learn a step-by-step process for fundraising (even if you don’t have high-powered connections), how to set up powerful introductions to investors with deep pockets, and how to use AI to boost your revenue — not just your dopamine.

Inspiring Quotes

• “To get great at something, you have to play the tape back and make one improvement and then try again.” – Joe Stolte

• “I’d rather be patient for the right chess move than just barf all over the situation or move too quickly. I want to move more like an orca and less like a piranha at this stage of my career.” – Joe Stolte

• “To me, the core of business is asking how can I behave slightly more like a detached scientist that’s just interested in running 10,000 experiments until I crack them.” – Joe Stolte

• “The absolute worst is rarely going to happen. Plan for the likely worst-case scenarios.” – Joe Stolte

• “I’ll never do another venture-backed company again. I want to play my game.” – Joe Stolte

• “Raising money creates the ability to create a bigger outcome faster.” – Joe Stolte

• “I think AI is as transformative as electricity.” – Joe Stolte

• “f you can get around a great leader and absorb what they’re great at, you will shortcut so much of your journey.” – Joe Stolte

• “Get comfortable asking for help, because you are going to need a lot of it all the time for the rest of your career, and that’s a muscle worth building.” – Joe Stolte

• Being predestined for entrepreneurship
• Quitting a $250K job to pursue a calling
• How breakdancing set Joe up for success
• Keeping your identity in new environments
• Tips for raising for a Series A
• How to set up impactful introductions
• The pressure that comes with outside money
• Going from $0 to $1.5M ARR in 14 months
• What should you not use AI for?
• Advice for entrepreneurs in their 20s

Brad Weimert: Joe Stolte, I am thrilled to see you. I am sad that we are not in studio today, but I appreciate you carving out some time.

Joe Stolte: Yeah, I’m super glad to be here. I would much rather be there, considering that we’re a 30-minute drive from each other.

Brad Weimert: Yes, well, all in good time. You are a super interesting character from an entrepreneurial perspective because you’ve had just a litany of different things you’ve been a part of from three exits, being the COO of Lottery.com, which went public at 526 million, and also, being a f*cking program manager for Microsoft. So, this corporate intersection with entrepreneurial ventures, and there’s a lot there, and then most recently, Daily.ai. And I want to get there, but let’s start with the beginning of entrepreneurship for you and how you started your journey there.

Joe Stolte: Yeah, man. I’m just one of those guys, I’m one of those small percentage of humans, I think, that was predisposition for entrepreneurship. And I don’t say that as if it’s like some kind of badge of honor because many days, it feels like a curse. So, I was born in the early 80s. My father was in the military. Instead of traveling, like bringing the family and moving us around everywhere, he just left for long periods of time. My mom worked two jobs. We’re kind of lower middle class, farm town of less than a thousand people outside of Portland, Oregon.

So, my first kind of entrepreneurial– like my first journey in entrepreneurship was in two phases. Phase one was my parents were working all the time and they couldn’t take me to school. We didn’t have a lot of money, so they would give me a little bit of lunch money to go buy, money at school, but the school lunch was crap. So, at 7 or 8 and I would walk myself to school, I’d walk by the corner store and I’d get all the candy that I could buy with my $2.78. And then I would just flip the candy for the best meals from the kids whose parents actually had time to make them good stuff, like the lasagnas or the sandwiches or whatever. So, that was the first thing. And I realize the value of money is, like, you can take money and turn it into stuff and get more stuff. So, that was the first hint.

And then later, when I was about 9 or 10 years old, this is like the early 90s. Back then, I really wanted Guess overalls, a Raiders Starter jacket, and Jordan shoes. That was like what I had to have because I was watching a bunch of MTVs. I was super into hip-hop. But my parents definitely didn’t have money. My school clothes budget was going to this place called Kmart and you had like 50 bucks, you can go hog wild for the whole year. That included underwear and socks.

So, I pretty quickly realized, like, there’s only a couple of ways to make money in my little farm town. And one of them was mowing lawns. The only problem with that is that I hated mowing lawns. So, what I did is I door knocked. I did about 50, 60 houses, and about half of them said yes, but I was like, “Hey, can I mow your lawn for 10 bucks? And then if you like it, can I just keep mowing it for the rest of the summer?” And they were like, “Yeah, sure.” So, the thing is, I hated mowing the lawn and I didn’t want to do it. I mowed the first one and I ran over somebody’s sprinkler and it was bad. It was like ended up costing me money.

So, what I did is I had my friends basically said, “Hey, can I borrow some of your lawn mowers?” I had my Mexican friends ask the migrant workers in my farm town if they would mow lawns for five bucks, and then they just mowed lawns all summer for me. And I got my money. And that’s where I first realized, like, there’s a better way than just going to work and figuring it out. I was too young to get a job. And I was a little bit too innocent to sell weed, which is the only other way that people were making money at my age, in my town. So, that’s what I did.

And then that was really my first ever journey into entrepreneurship. And I could keep going. It’s like, I didn’t build businesses, but it was like one hustle after another until I finally learned about business and the game of business, entrepreneurship, and the different levels and how you could play. And then I was like, “Oh, wow, okay, here we go.” This is a whole other level to this game, and there’s many layers to that onion.

Brad Weimert: Well, I want to talk about the formal businesses that you’ve been a part of. But that initial journey, there are a couple things that hit me there. One is leverage. One is the early realization that you didn’t want to do the thing. You wanted to create the arbitrage, right? You wanted to get the margin and have other people do it. I kind of grew up with a lot of the same hustles, but my first foray into making real money was selling, was sales, and that was heavily dependent on my own actions. And to this day, to my great detriment, because I still think I’ll just do that to myself. And way past the point of that being a functional path for scale, growth, etc., how do you think that has rippled through the rest of your entrepreneurial journey? Or has it?

Joe Stolte: Yeah, it definitely has. So, for me, over time, I’ve learned that my zone of genius is in four areas. It’s learning, connecting, creating, and coaching. And I put sales and marketing under coaching. Just all forms of influence sit under that folder in my life. But I didn’t know that for a long time, so I ended up, had this whole journey in my story where I was a professional dancer and made basically no money. And then I found a mentor of mine one day that worked in management consulting, and he kind of put me on to this world of business. He took me under his wing and ended up going to college. And that’s how I ended up at Microsoft. I did a few years in management consulting, then I ended up at Microsoft.

And at that time, it was the opposite of leverage. It was like, how hard can I work to break through this glass ceiling and make more money on a salary basis than anyone else in my family really had ever? And then I found myself at Microsoft. I was making a quarter million dollars a year. I was in my mid-20s, late 20s, and I’d wiggled my way into a remote work situation where I was flying to all these other countries that Microsoft operated in, and no one really knew where I was. So, it’s kind of a dream job, except I felt this calling on my heart that there was something better. I was watching my friends who were both good at leverage, smart, a little bit lucky, and putting themselves in the right place at the right time. This is in the early 2000s. And I was like, “Huh, well, what if I started to use some of this leverage stuff and stop working so hard, but combine them where I could actually raise money and get other people to do the really difficult things that I don’t want to do or don’t want to muscle through? But I’ll still work hard.”

So, I didn’t really give up this hustle and grind. I just pointed that laser beam somewhere else, and I tried to raise money to hire other smart people to do their bit so that we could go farther faster and make a huge debt. And that was my first big, like, oh man, we could really, really make money and really have an impact on the world with this model. And as soon as I kind of connected those dots, I was like, there’s no way I could stay at Microsoft. I mean, I learned a lot working in a big company. I really did. I got to work under some amazing leaders. I got to learn how they think, how they move. I was desensitized to obscenely large numbers, working at Microsoft and going down to the country manager of Mexico, the general manager of Mexico, and saying, “How do we get from 750 million to 1.5 billion in the next five years?” That was the nature of my work with that particular part of Microsoft. And so, I’d just been desensitized to the number of billion.

And so, doing things with people to get a lot of money to go from other people’s bank accounts into yours, I got desensitized to that, which was good because when I became an entrepreneur, my expectation wasn’t, oh, man, getting a million is hard. My expectation was like, I got to build a unicorn. I got to build a business valued at $1 billion. And I didn’t have an appreciation for how hard that was, but one of the gifts I got from the corporate world is the big numbers. It’s like, get into a million didn’t seem a big deal to me. I was like, oh, just hurry up and do that.

Brad Weimert: I think normalizing higher levels is a very helpful frame until you normalize something that’s really hard to launch off it and move past it. I also have no choice but to pull on the thread. I mean, we talk in Broadway, we talk in strip clubs. What do you mean becoming a dancer?

Joe Stolte: Yeah, I was a member of the two-time world champion breakdancing crew, the Massive Monkees.

Brad Weimert: Shut the f*ck up.

Joe Stolte: We have the most watched breakdancing crew video on YouTube. I could keep going. We toured on Warped Tour. I helped get into the Olympics. I’m going to be in Paris in a few weeks. We’re breaking in the Olympics. And we helped get it into the Youth Olympics. I created the qualifying event for the youth, like youth national qualifier for North America. I’ve had this whole separate alter identity, like this Clark Kent thing versus Superman thing. I have this alternate identity as a b-boy, as a breakdancer that you…

Brad Weimert: Yeah. It does not sound like Clark Kent at all.

Joe Stolte: Yeah. Well, I think this is Clark Kent, and that’s probably Superman, whatever, but like, no. But yeah, so I had this whole other life as a professional dancer, man. At 17, I didn’t want to go to college. I just wanted to train breaking eight hours a day, like a warrior and a champion, and then…

Brad Weimert: So, how did that happen? So, I grew up, music is like, it’s a huge portion of my life. I had an underground hip-hop radio show for five years. My whole world was underground hip-hop for a very long time, but I also had this draw towards money. And as soon as I figured out that I was in control of how much money I made, my focus changed. And I really thought at the time that I would want to get back to music. And there’s part of me that wants to spend time on that, but it is dwarfed by my desire to create a much bigger life. But it is a huge part of my life, and hip-hop was. Hip-hop, from a music perspective, was really important to me. The graffiti was very important to me as well from an artistic perspective. The breaking was super interesting, but I had no desire to be a breakdancer. Where did it start? And how did you find yourself there as opposed to another area of hip-hop?

Joe Stolte: Yeah. Well, I started when one of my older brothers, half-brothers played the bass. Another one played sax. And then me and my closest brother in age, we loved hip-hop from six, seven, eight years old. I was getting tapes in the 80s that came up from California. I got on one side, it was like 2 Live Crew’s As Nasty as They Wanna Be. On the other side, it was N.W.A.’s Straight Outta Compton. So, it was mostly West Coast and bass rap.

But I started emceeing at a really young age. I still have my brother Sly’s tapes of us recording ourselves rapping, like five and six, just trying to emulate. And I was raised, I went to church, and so, what I would do, the way I learn how to rap is I would want to rewrite the raps with other cuss words. So, I would think, what’s another way where we could say that but not swear? So that when I’m doing the lyrics in my head, I didn’t have to have all this negative stuff running around in my head.

So, first, it was emceeing, then like, I think it was Source Magazine or XXL, I saw an ad for turntables in the back. So, I did another hustle to get money and bought turntables and started buying old records and figuring out how to mix. And then what happened is I was to play basketball competitively, like thousand free throws in my driveway kind of a kid. And I was so competitive with myself that I just get this burning desire and I’m like, I want that. I’m going to put the work in and get it done.

And then what happened is, like, I saw some friends of mine try– they’re breaking and they’re getting pretty good at it. So, I tried it and I was so terrible at it. I mean, I couldn’t do a handstand, a cartwheel. I was like, the least physical dude in the world is like gangly white kid. I love to dance. I could dance though, like, I could do the running man and I had rhythm. My mom had rhythm, I had rhythm. So, yeah, I tried it. I was so bad at it, and I was just like, I got to master this. I was like, I have to get good at this.

And I really wanted to learn the windmill. So, I would go home and I would watch Beat Street and then I would record myself on this little VHS camera that I borrowed from a friend. And I would try it for 20 minutes, and I would watch the tape and I would try to figure one thing to improve. I didn’t really have a teacher, just had some other guys learning, and that was it. I was like, I just have to learn the windmill.

And then that thing just consumed me. I started going down the rabbit hole of like, what is real hip-hop? And like, where did it start? And then, sooner or later, I’m 17. I’m like, okay, I’m out of high school. The first thing I wanted to do is go to New York. So, we’d go spend summers in Harlem and the Bronx, and we would learn. I’d go to all the boroughs and learn from all the original b-boys that were from each borough. They each had a story about where the moves came from.

And at this point, I’m just fully immersed in mastering the culture, the history. How do we apply that to movement? The world just kind of didn’t matter to me. All I cared about was learning this dance, making my mark on this culture, being as good as I could and just one thing after another. And so, I just had the laser vision on. I locked in, and for me, breaking was the first thing that I mastered, right? I just chose mastery. I want to learn. Like, in breaking, we have sayings, right? I think it’s in hip-hop too, but like, each one, teach one. You learn something, you teach somebody else.

I’d go to New York and learn the style, learn this, like, the mentality. Then I’d come back and I would teach it in Seattle, where I was at the time. Another one is like, always be a student. So, I’m always trying to understand what’s the history of an idea, what’s the history of this thing? So, I can understand the context and honor that. Another one is like, it’s a bit like respect your elders. So, there’s this rule book I got inadvertently from studying breaking culture.

But the reason why that matters, the business, is that’s the same rulebook I took to learn management consulting to be great at Microsoft. And then when I became a tech entrepreneur, it’s the same rule book. I studied the history, I was humble, I put the work in, I ran the tape back, just like when I was trying to learn windmill. If I’m trying to do something, learn how to speak, learn how to sell, learn how to write coffee, learn how to manage a team, or at the time, it was just of like one VA or whatever, I always want to improve. I had in my mind that to get great at something, you have to play the tape back and make one improvement and then try again.

I got that from breaking. So, it’s actually a really important segue to my story that I usually don’t get into, but that’s how I got into it. And then it just became this sort of operating system for anything that I approach. At this point, it’s unconscious competence. I just go into a new topic. I love learning it. I’ve got a process and I just do it. But all that came from breaking, man. It came from loving something, having that singular focus, and just being relentless on getting from where I am to where I want to be and just do it constantly, manufacturing my own desire and my own optimism, especially when I was terrible. And there’s times been like, we could do a whole podcast on this, where like there’s a whole streak where we would just get second place all the time. But these big world titles and you train all the time and you go and then some subjective judge makes the wrong call and you lose by one vote, I mean, it’s heartbreaking.

So, all of that set me up for all of the face punching that came later as an entrepreneur. And in some ways, as an entrepreneur, I’m like, no, this is all right. I’m not dancing in front of 30,000 people. I can probably handle this webinar. You know what I mean? There’s just such a different set of experiences that I can normalize back to that made a lot of the– what I watch other people struggle with in entrepreneurship, I was just lucky because I did something similar in a similar capacity in a different lifetime, basically.

Brad Weimert: Yeah. I mean, I think that one’s perception of luck versus effort and experience and drive, it’s an interesting balance, and I think there’s truth in a lot of different ways when you position things. But the experience, certainly, I mean, I can see tons of throughlines there. Also, you’re digging into sort of two different chapters, right? The first is the choice to master and starting at a point where you’re terrible. And the lesson there for people is really important because most people, when they’re terrible at something, they never bother trying to even get off the starting line. They just say, “I’m not good at that.” And they self-identify as not good at that as opposed to self-identifying as being at the beginning, right? And there’s an important difference between those two characters.

And then the second one is being in these worldwide competitions where you’re coming in second place and you’re towards the finish line of mastery or way deeper in the game, I don’t know that there’s a finish line. One of the things that is curious to me through that specific context is you are a white kid in the mid-90s, late 90s trying to be a breakdancer. I would imagine, as a DJ in the mid-90s, as a little white kid, I can relate in some level, but I would imagine that you did not feel part of the group, part of the culture, and you were isolated in some respects. There are a lot of business situations where you walk into the room and you are isolated. You are not yet entrenched in the culture. You do not understand that you do not fit in. Did you experience that isolation in the hip-hop culture as a white kid in the 90s? And how did that impact everything else?

Joe Stolte: Yeah, man, I mean, I didn’t really have any white friends growing up. I have my brothers, my half-brothers and my brothers. So, that was my closest. And then it wasn’t until high school, I met kind of a mentor in hip-hop, a guy named DJ Bless, and he really showed me like, oh, man, there’s so much more to this. There’s the four elements and there’s all these unwritten codes. And I was like, oh, I was getting the special esoteric knowledge. And he was a white guy as well, but he also grew up in the Portland area, being kind of the only white guy as a DJ as well.

And I mean, I just grew up not around a lot of white people. So, I just kind of normalized, like, I’m not going to swear in Spanish, but the things that, like, I would walk into the room and I would just hear that and I would just laugh at it because I’m like, yeah, yeah, yeah, I’m the white guy. Or we would go into different hoods all over the world, really, but also, in America, we’d be in Chicago, we’d be in New York, we’d be in just LA, Oakland. Part of it was isolating, but also part of it was like, I just felt honored to be there, man, honestly. I’d go, and these guys from the hood would give us the ghetto hall pass and we’d go to Harlem and the right people would be like, yo, these guys are with us. And when they’re coming and going, don’t bother them.

Same thing in the Bronx. You go with the right people to the right park and then there’s a good chance that no one’s going to mess with you. Obviously, there’s no APB that goes out, so you still got to watch out or whatever. But I learned how to adapt. I learned that, yes, I’m white, and it’s also how I hold myself. If I was showing up with a suit and a briefcase at two in the morning going into the Bronx, at the times when I was going there, probably a bad idea. But if I’m the only white guy and I dress the part and I’m not being too noisy or being a prick or drawing attention to myself, then I’ll probably be okay.

But I came, batteries included, knowing like, yo, this is not my world. I’m not a default member of this world. So, there’s always some level of tread carefully and tread respectfully. And I just grew up in a weird neighborhood, like, always looking over my shoulder, and a lot of people getting in fights, a lot of drugs, a lot of gangs. So, I don’t know, part of that just came, batteries included. And thinking back about it, it’s such a long time ago, I forgot what it feels to feel like that. But yeah, I mean, part of it was isolation and part of it was just like, how respectful and adaptable can I be?

And that’s the demeanor that I’ve taken into, like, I can go to any situation and think like, all right, how respectable and adaptable can I be without losing my identity, without losing my authenticity and turning into a people pleaser or trying to be someone that I’m not? I got to understand that barrier. But there’s a certain flexibility to behavior that I got from that exact situation being the white kid, the only white kid most of the time in almost every environment that I was in, in middle school and high school.

Brad Weimert: Yeah, I love that. Well, let’s talk about your first entrepreneurial foray from a sort of structured, formulated perspective. Bootstrapped, funded, how did you dive into that world?

Joe Stolte: Yep. This is probably a boring place to start, but the first company I ever really started was a charity. We started a company called Extraordinary Futures, and I basically licensed the Tony Robbins Research Institute material, which is kind of like all Tony stuff distilled into a sixth-grade level. And we built a leadership program that combined teaching breaking plus this stuff. And we had hundreds of kids in Seattle in our programs, and we really codified that organization. But man, I wanted to make money and there wasn’t a lot of money in that.

So, the next thing I did when I left Microsoft is I started a company called Rallysong. And that company we raised money for, we raised about a million bucks from what we would call friends, family, and fools. At that stage, we’re really selling the team and the dream. It’s like, “Hey, look who I have around me. Here’s the big idea that we have.” And honestly, man, I kind of cashed in three or four years of credibility that I built in the professional world, the corporate kind of Fortune 50 world to say, “Hey, I’m going to go make this move over here. You trust me from this world. I’m going to cash that credibility in and ask you to support me financially in this new world.” So, my mentor and a handful of people, they funded that company.

And that company was basically– this is back in 2013, and we built a platform that helps big musicians raise money for their favorite charities. And then we kept a percentage of it. And it’s cool because every dollar that you donate, you put a name in the hat. We draw a lucky winner, and then you get to go have an experience with that artist. So, we did yoga on the beach with Jack Johnson or we did a private guitar lesson with Jonathan Davis, the lead singer of Korn, and on and on and on. We grew up with all these different bands and famous people. I was living in LA at the time, and that business was amazing.

And what I realized is that I got lucky on that first fundraise because when we got to our Series A, I got left at the altar. This guy, basically, we flew to Dallas, I won’t say his name, but we high fived and popped the champagne and then, man, he negotiated us forever after that until we ran out of money and then bought one of our biggest competitors. And whether he did that strategically or he just lost faith in us, I’ll never know. But I realized that I learned all this stuff in corporate America, but man, I didn’t know anything about fundraising. I got lucky. I got real lucky, and I didn’t go to Stanford. I mean, I had management consulting at Microsoft on my resume, but none of the people around me kind of had these gold stamps of approval that tend to give you a lot of grace when you’re raising money, like if you went to Stanford or MIT or Harvard and you went to Y Combinator or whatever. So, I didn’t have any of that, and we got lost. We got our faces ripped off.

So, I went from quarter million dollars a year in super easy job to over $37,000 in debt and my credit card declining at the Whole Foods in Venice Beach where I couldn’t pay for my hot bar food and me walking home with my tail between my legs, like, oh. So, that first company was bathing in the fire of failure, spectacular failure. I can laugh about it now. But it didn’t feel very good at the time, for sure.

Brad Weimert: Bathing in the fire of failure. So, I want to talk about the attempt at the Series A because, look, raising money is a full-time gig. And when I talk to serial entrepreneurs who have only done it with other people’s money and they’ve never bootstrapped, when I talk to you and I’ve had the good fortune of talking to a lot of people at this point around this, the responsibilities of a CEO in a venture backed startup, one of them is always around fundraising. And it’s a never-ending responsibility and it’s a skill set, like you have to know. And as you pointed out, you did not have the background for it, nor do I. Tell me what you would have done differently through that Series A today, because today, you’ve now gone through this a few times. What would you have done differently to protect yourself then? And what are the kind of lessons to avoid when you’re raising a Series A?

Joe Stolte: Yeah. I mean, that failure put me on this journey to really master raising money. So, what I would have done is I would have read the most recent book, a book from 10 years ago, and a legacy book on money and fundraising or, like, Guerrilla Financing. I would have read a bunch of books on fundraising, I would have found a mentor, and I would have asked somebody that’s already done it and just try to model what they do, or at least try to model what I think the throughline was for me. I didn’t do any of that. I just went in with this kind of kid-ish, like, “Oh, it’s all going to work out, and everybody’s my friend. And you’re a cool guy. You’re a great investor. Let’s do it.” Because that was my experience before.

And what I would do differently is this is my process for fundraising. It’s really simple. I make a list of 100 potential people that I’m going to raise money from. And when you’re raising money, my experience of it is you’re in one of two camps. Camp one is you’ve surrounded yourself with enough social proof, enough seals of approval, some like Stanford kids or Harvard kids, MIT kids, people with past exits, people that have worked at Goldman Sachs or whatever, McKinsey. And then you’re kind of in a different class. You maybe have two or three conversations. VCs are generally pretty nice. And usually, the tier one, the Andreessen Horowitz of the world, the Sequoias of the world, they’re going to write you a check, or your alumni network is going to make those intros. And that’s kind of how that works.

I think everybody else should prepare themselves for 150 conversations. So, what I do is I make a list of 100 investors that I’d like to get money from and I categorize them as high, medium, low for fit. Fit would be like they can help me beyond the money. They’re not a jerk and they’re not going to try to kick me out of my company later. So, I have high, medium, low. And low is just like someone that could give me money, but there’s no strategic value. Medium is in the middle, and high is like, that’s the best. It’s all those things.

And them investing in my company kind of already pre-raises my next round just from a signaling perspective, a social perspective. It’s like if Andreessen Horowitz backs you, for example, I’m using those because a lot of people know about a16z. It’s a huge signaling mechanism for what comes next. So, make that list of 100, high, medium, low. I put my pitch material together. And by the way, what really cracked it open for me was reading Oren Klaff’s material, particularly Pitch Anything if you’re interested in fundraising in any capacity. That was my Bible at the time. I really mastered everything in that book and tried to apply it.

His second book is also very good. It’s called Flip the Script. It’s a little more advanced, but Pitch Anything was what really opened it up for me. So, I would get all my material ready, and then I would have the framing correct. So, for everyone that I’m trying to get to and if Brad’s the guy I want to get to, I want to get an intro from somebody that already has Brad’s respect. So, in that person, make that intro, I inherit that respect by default, at least, versus me coming in cold or knocking on the front door. I’m not against that. I’m happy to do that. I just know that from a relationship leverage perspective, kind of like the mowing lawns example, I have a lot more leverage if someone that Brad really respects makes that intro.

So, I’m going to do a little digging to try to get those intros, but here’s the big strategy. I’m going to go to the bottom and I’m going to pitch them, I’m going to go through my pitch, I’m going to do all my stuff, and then they’re going to tell me what they like and don’t like. They’re going to ask a bunch of questions. Then I’m going to revise my investment deck. Then I’m going to go to the next chunk and then the next chunk and then the next chunk. By the time I get to the top and then my pitch is battle hardened, every FAQ you could possibly ask me has been considered. I’ve revised, I think, probably 20 times. I’m like, I know my pitch so well, I’m singing it. I know what questions you’re going to ask ahead them off with the pass.

It’s kind of like doing a really, really dope webinar. The more you do it, the more you get used to it. And then you start doing the FAQs at the end. You might be thinking this, there’s that version in your pitch and the pitch isn’t always like, in fact, it’s very infrequently like, “Hey, Brad, sit down and let me present to you for 15 minutes, then you ask me questions.” It’s more like, “Hey, you’re going to read my deck and we’re going to have a conversation.” So, what I do is I make a Loom where I make it very informal, no more than seven, eight minutes. I get through all the material fast, and then I just let them ask me questions, but we’re facilitating the same thing.

But then anyway, that’s my process, man. By the time I get to the top, I might have to have 20, 30, 40 conversations, but everything’s buttoned up. I got everything they could possibly ask me for ready. And I’ve just kind of reverse engineered that group of investors in terms of what they would need to make me investable, and then I just keep morphing my situation until it’s a square peg in a square hole. And then I get my check and then we move on.

But it’s a long process, it’s a full-time job. It’s like you’re selling a security and it’s like a security, it needs to be an offer, man. Most people, the fundraise, don’t think about it like that, but I’m from the direct response marketing world too, like, it’s a security. It’s got to have its own marketing, its own positioning, its own offer, its own ideal target avatar, all of that stuff, its own affiliates, its own partners. Just think about it like that and you can actually get, I think, a lot more traction than people that don’t know anything about fundraising.

If you know about selling and you know about webinars and offers and that kind of stuff, it’s very similar. But I think a big mistake that I made is I didn’t appreciate, hey, man, this is the security. It’s like having a second business with a second brand and a second story and a separate market that I’m selling to. So, if you treat it like that and you put the time in to craft all that stuff up, man, it can actually be really fun. But if you don’t respect it and you don’t put that work in, then you can get your frickin’ ass kicked, and it sucks.

Brad Weimert: So, create a big ass list for potential investors, 100, 150 potential investors. Rank them, low, medium, high, in terms of functionally, whether they’re smart money or not, whether there’s additional value outside of the money and character and all those things. One of the big things that you mentioned that resonates is third-party credibility, is get edified by somebody to get the introduction into those people. One of the things that happens pretty routinely in my life is somebody who says, “Oh, hey, do you know Joe Stolte? And he’d be great for blah, blah, blah.” And I’m like, “Yeah, but you should do an intro,” because that introduction, even though I already know you, still adds additional credibility to the picture. And there’s another person chiming in, saying, “Hey, you should do this.” And so, even if I’ve been introduced to somebody once, twice, three times, another introduction from somebody else still adds to the picture.

Joe Stolte: Oh, 100%.

Brad Weimert: So, I love that.

Joe Stolte: I mean, I do this in everything, man. We can get to Daily, but a customer I had on my kind of dream 50 was Dan Sullivan. He’s like at the top strategic coach. I had multiple offers get introduced to Dan Sullivan by multiple people. And I was like, “No, I’m good. I’ll wait,” because I knew that I wanted to be introduced to Dan Sullivan through Joe Polish because I know they’re really close. And I love Joe and I know that my business partners are friends with Joe. So, I go into Joe first. I develop the relationship with Joe. I really serve Joe. I built a genuine relationship. It wasn’t like I’m like social engineering and we’re being manipulative. Like, Joe is a friend. We work together, we partner together. And I didn’t even tell him, “Hey, man, I want to meet Dan Sullivan.” Just naturally. Naturally, he put me in a place where he would endorse me to Dan. I didn’t even ask for it. I just knew that if I served Joe enough, he’s such a giver, he’s going to introduce me to Dan. And that bridge was 10 times stronger than the other people that had offered me to introduce me to Dan in the past.

So, I actually passed up the offer until I found the person that I thought was the right bridge because, I don’t know how, maybe it’s possible, but I don’t know how to erase a first impression, oh, like that first bridge. I don’t know how to erase that. I can wait and get a better one later. And I’ve done that. And it also works. I feel it, I feel like there’s a residue of that first introduction, that first impression. And I’d rather just be patient for the right move, the right chess move instead of really, like super eager to just barf all over the situation or move too quickly. I want to move more like an orca and less like a piranha in the game at this stage of my career. And so, that third-party credibility and the right third-party credibility at the right time, I mean, then in my opinion, it’s worth waiting for if the person is the right person and you want to be in a relationship with them.

Brad Weimert: Yeah, I think Dan is in the middle or somewhere there. If somebody, if I identify that the referral source is not going to be highly credible, then I’ll pass. But I’m infrequently around people. In those contexts, it happens, but I’m pretty f*cking deliberate about who I spend time with, so it’s more common that I have a highly credible person doing the intro. So, I won’t wait for the magic one. But it’s a different approach, and I think that’s a really good point. You can’t erase a first impression.

Joe Stolte: I mean, I don’t know, everybody, to be clear, but if you’re in my top five, I’ll wait. I might not be in this game for a long time. This is what I love to do and I don’t have to rush it. But just about everybody else, I’m not that calculated. I’m like, oh, cool. Yeah, I’ll talk to that guy. But it’s important, man, being even marginally intentional about (a) going through a third party that has a good bridge and good, like, I call it getting prescribed, I want to get prescribed by the doctor level authority to someone else, then I inherit the residue of that. But if even just a little bit intentional about that, it’s incredible how much faster you can fast forward through all the bullsh*t of getting to know somebody and just get right down to it.

Brad Weimert: So, the final point that I wanted to wrap to close out the fundraising element was you mentioned strategically going through the pitch from low value to high value investors. And I think that that’s a really, really important thing to highlight, because most people and most business contacts go straight for the largest fish, the big whale, because they’re like, oh, that’s all I have to do. I have to get this one instead of getting your reps in on a lower value target. So, work with a bunch of low risk, low reward possibilities, prospects, whether it’s a client, a strategic partner, in this case, an investor until you are f*cking dialed. And then when you’re ready, you can go after the bigger stuff. And I think that that lesson is just gold for so many different scenarios in business.

Joe Stolte: 100%. There’s no way the first version of your product is going to be great. Go for version 10, man. You can fly as like I’m going to give it to people, care about their reaction to it, take that feedback, iterate, and have that iteration cycle. To me, that’s the core of business. It’s like, how can I behave slightly more like a detached scientist that’s just interested in running 10,000 experiments until I crack it? Then coming in like, oh, I’m just one funnel away. I’m just going to make that one funnel and crack it all the way open or I’m one sales letter away. The thing is that that’s true, but it’s only partially true. You are one funnel away, but you got to get through the other 99 to get to the one a lot of times.

So, yeah, I just come in with that expectation and I don’t know if that’s a limiting belief where I create my own reality, I make it harder than it needs to be. But I’m very comfortable in that approach. I don’t need to be the expert. I just need to follow the same formula that I learned windmills with and breakdancing to do almost anything in business. And over enough time, I’ll crack it.

Brad Weimert: Well, let’s fast forward to Daily.ai. So, let me start with the year that you started the company.

Joe Stolte: Yeah. So, in 2021, I was at GrowFlow and we sold that business for just shy of 70 million bucks. We took it from a million in ARR to 8 million in ARR, and we sold it for just shy of 70 to the largest payment processor in the cannabis industry. We were the largest compliant software in the cannabis industry. And I was about to have my second child and I was, like, hey, man, I’m in my late 30s.

Brad Weimert: I’m sorry, I have to interrupt. I blame this on you entirely. You brought up the numbers in the sale. So, you sold it for 70 million to a payment processor. You’ve got all sorts of bells going off in my head. You’re a compliant software for cannabis. And for those that don’t know that space, so Easy Pay Direct is very deep in processing for CBD, and as of June 2024, nobody in the world can process for marijuana through the Visa/Mastercard rails. You can do the debit card networks and there’s some other random workarounds.

But as a result, I happen to know a sh*tload about this space in compliance, and cannabis is a huge deal. And it’s a sticky one, too, man. Like, for you to dive into that particular place is bizarre to me anyway, because it’s a complicated, horrific regulatory nightmare. But I want to hear about just the– because I do want to get to Daily.ai, but tell me about the fundraise and the dilution and the exit of that particular business in the timeline, because somebody that’s been in and out of a ton of businesses like you have, both as the COO and as the founder, etc., it’s interesting to hear how you think about it, but give me the metrics and timeline for that stuff.

Joe Stolte: Yeah, for context, my first role in entrepreneurship was the COO, then it was the chief revenue officer, and then it was the CEO. In between, I was COO of a company that we quickly sold. So, I got that chair. But I’ve kind of switched hats over the years to find what I like the best. Candidly, if I could go and wave a magic wand, I would just be a chief revenue officer forever. It’s so much easier than being CEO. But anyway, yeah, so the company’s name was GrowFlow. And I didn’t start the company, a guy named Rufus Casey started it, and he had a lot of foresight in that space and he got the company to about 900k in ARR and it kind of got stuck and hit a ceiling.

And then a good friend of mine who I’d sold a business with before and spent time with that Lottery, Travis Steffen was advising them and he came on, and they asked him to come on as CEO, and he asked me if I kind of wanted to be co-CEO. And I’m not into the co-CEO thing, I think, one head for each role. But I was like, “Hey, I’ll be the chief revenue officer.” So, we kind of had to clean up the cap table, the capitalization table, who owns what, investors and all that. And then we went it up, we brought it out for an investment round. We basically followed the playbook I described earlier in the conversation. And we were able to get about an $8 million round on March 20th of 2020, right before the world got face slapped with COVID.

And we were raising that money, like my plan was to build localized sales teams in door knock, right? Door knock cannabis facilities. Why? Because you can’t run ads because it’s a regulated market, and you can’t really do anything on organic social because unless they’re looking for you, the algorithm just nerfs you permanently. So, I was like, “Cool. Let’s just build a localized sales team. I did this at Microsoft. I understand structurally how it works. It will be a little bit different, but let’s go.”

Then COVID happens. I’m like, “Oh, man.” So, what did I do? I pulled out my direct response playbook. I did direct mail, gag gifts over direct mail to hook them into email, and then we built a 15-person sales team, all virtual. And those guys, we trained every day, like role playing every day. And just a beautiful, beautiful machine of revenue that we built and we just slowly chipped away every month, grew every month, every month, every month. We got to about 8 million in less than two and a half years. And then we flipped it and we sold it to Dama Financial, who, again, was like kind of the largest solution in the payment processing space at the time.

And again, I’m not an expert in the payment processing side, except that I know it’s a pain in the ass. But I was glad to sell that business because, man, I’ll be honest, the only reason we were in that space is because regulated markets were second nature to us. We just built Lottery.com. We had, I think, at one point in time, 13 active bills in different states to change the legislature, to make what we were doing legal. We had this huge lobbying force.

So, going into cannabis, I was like, “Man, all right, I understand regulatory environments. It sucks, but we can figure it out.” And we did. But as an extra, it’s a whole other layer of pain that I would not recommend anybody subjugate themselves to at all. But that’s it. We did one round of financing and it obviously diluted everybody down, but it was a little bit of a cap table clean up and reset. So, it was kind of nonstandard. And the fund that came in and supported us was kind of half venture capital, half private equity. But, yeah, so I was one shot at capital, and then we sold the company to Dama just a few years later. And so, it was a nice, clean ride.

Brad Weimert: So, was doing a million, one shot of capital for 8 million, was doing a million a year, one shot of capital at 8 million, and with what valuation? And said another way, how much of the company did they take when they gave you money?

Joe Stolte: Yeah. I don’t remember the exact numbers on this deal, but I think we sold about 30% of the company, right? So, that would have been, $24, $30 million post-money valuation, something like that. When you raise a round, especially like each round, the benchmark that most people go for is you really don’t want to sell any more than 20% of your company. So, if you think I’m going to need four funding rounds to get to a $1 billion valuation and I had to go public or get bought for a lot of money, you just want to do the math. You start off as a founder, it’s me and Brad. We’re going to go start the ACME Venture. And we’re 50/50. And then you create what’s called an employee stock option pool and you’re giving equity to your employees, and that’s usually the 15%. So, now, we’re diluted 15%.

Then we go raise our first round. We’re going to lose 15% to 20%. The next round, we’re going to lose 20%. The next round, we’re going to lose 20%. So, each time you’re diluting the game is if I lose 20%, can I take that money and make the pie so much bigger that my net outcome from that business and my net equity is actually worth more, even though I own less of the company over time? And it’s a game of speed.

The difference between this and bootstrapping is with bootstrapping, you can play chess a little bit more earlier, but with venture, dude, at GrowFlow, we went from 119 employees in less than 90 days. We raise the round. We blitzscaled, dude. We hired an army and we just took the market by storm. Because that’s what you do when you raise money, it’s like gun to the head. The money is the clock. How fast can you go without making mistakes? Giddy up. Like, that’s it. Whereas, like, I’ve built an agency and sold it, where none of that time pressure was there. It’s like, you have a whole different set of challenges, which is keeping yourself motivated. But with this dude, like a metaphorical kind of the head, there’s always this pressure. There’s always this little bit of an anvil on my chest, like, yo, what are you doing? Let’s go, let’s go, let’s go.

And so, I kind of think about it like being an athlete. If you’re an athlete in the NBA, if you’re LeBron James, it’s like, you’re really good, but you’re playing someone else’s game even if you love it. So, after Daily, I mean, this is not what the podcast is about, I’ll never do another venture backed company again. I want to play my game, where I had Garrett Gunderson come speak at an event that I did, and his whole thesis was like, “Dude, just play your game.” And I was like, “That’s right.” And I just woke up. I’m like a thoroughbred horse running around in someone else’s track right now, which is fine because I love it and I’ve done well for myself financially. But how much better is going to be when I play my game, where I set the rules and I just build the whole thing myself? But, yeah, that’s how the fundraising game works.

But dude, it is literally gun to the head, go. And if you stagnate, then some kid in San Francisco is going to come up with an idea and pitch it to someone and raise more money and move faster than you, or build some piece of technology that makes you obsolete. So, it’s go, go, go from day zero.

Brad Weimert: Let me challenge that for a second.

Joe Stolte: Please?

Brad Weimert: It’s go, go, go. Do you think that that pressure produces a better outcome than not having that pressure in a bootstrapped environment?

Joe Stolte: I don’t know. I have this framework in my head. Like, if you draw a parabola, like an upside-down U, that’s like in a statistical distribution, everything to the left is the early stages, and everything to the right, it’s like the later. I think if you’re on the left side of the parabola, speed is more important. And as soon as you get close to the top or the middle, thinking before you leap becomes infinitely more important. So, Microsoft, way to the right. Rallysong, way to the left. And this is, as you scale, thinking before you leap becomes more important. And that is equally true in a bootstrapped company, but I don’t know.

One of the things I think about with early stage and raising money is that producing a better outcome, I think it creates the ability to create a bigger outcome faster, right? Look at ChatGPT, man, fastest growing product in human history. That company was not bootstrapped. That would have not been possible unless it was a phenomenally rich dude that just self-funded it. You don’t build something like that on your own.

Brad Weimert: Kind of was. I mean, the phenomenally rich dude was Elon.

Joe Stolte: Yeah, but they used a bunch of other people’s money, dude. And it was, like, Sam Altman didn’t go. Man, you know what? Guys, we’re just going to drink Red Bull and crank it out in the garage for six months and launch this thing. That’s possible with techno– it actually is possible now to do that. I just think that the scale with which they’re operating, you go from never really heard of you to the average person to the fastest growing product in human history, to being called before the Senate to talk about the safety of AI and being one of the most important names in technology on the planet, in like what? Like, less than a year. That’s kind of…

Brad Weimert: Yeah, this is a good transitional point. And that’s why I asked you the timeline for Daily.ai. So, you started Daily.ai in, you said, 2021. Is that right?

Joe Stolte: Yeah, 2021. So, the backstory there was basically like, Peter Diamandis and Eben Pagan had taken an idea of Eben’s and paid a little bit of money to have someone build– my business partner, Morgan McDermott, build a prototype and had put it in front of a few people, but it really hadn’t seen the light of day from a marketing perspective and it really didn’t have any positioning. The product wasn’t entirely usable yet. So, I came on, and it was literally, like, GrowFlow is under contract. I’m like, I met these guys and I was like, “Let’s go.” And I was like, “I will moonlight as whatever you need me to moonlight as to see if there’s a market for this.” And I just jumped right into the next thing because I was like, “This is my last time to do startup stuff.” I was 39, second kid on the way. And I was like, from a stage of life perspective, it’s stage appropriate for me to take another crack at this.

When I’m in my 50s, just me personally, my choice, I don’t want to be playing this kind of game. I want to play a different game. And so, yeah, we launched, we started tinkering at the end of ‘21. We launched an alpha in 2022, and then ChatGPT came out at that year, like October, November. And it was like, all right.

Brad Weimert: Well, let me– so that’s actually what I want to talk about because the GPT models, when ChatGPT launched, it was ChatGPT and it was 3, right? But we look at, I think you also know the– I don’t even know what the f*ck they’re calling themselves now, the Jasper guys. Is that currently their name?

Joe Stolte: Yeah.

Brad Weimert: They went through a few different names, I lost track. But they’re local and they’re great. But similarly, they got involved in the AI model very early. And the evolution, the power of the GPT models as they escalate, it’s significantly different than it was early. And so, what the product could be and what it did when GPT 3 happened, or before that, it was very different than like now at– now, we’re at 4.0, right? It’s a radically different product. So, what was it? Like, where were you in terms of that release? And did you feel ahead of the curve? And how much did the product work then versus now?

Joe Stolte: Yeah. We were very fortunate because Peter Diamandis is kind of a high-profile futurist. He has a lot of access to, like, Eric Schmidt, his homie, he helped inspire Elon to get in the space race. I mean, he’s very connected. So, we got OpenAI access to the API, to GPT 2 very early, like in 2021. And so, it was fun, man. We were early and we developed a real perspective of where the puck is going. As a non-AI guy, I was able to come in and run my same playbook of trying to master this and learn to it, dig, and get a sense of where this is going.

And so, we launched that alpha product in 2022 and where I wanted to take the business, there’s two problems. The capability of the machine learning wasn’t there yet. And the willingness of the marketplace to accept what I wanted to build wasn’t there yet, right? I didn’t trust a total AI, like my vision for Daily.ai is taking one to many marketing and segmenting it to the perfect 1 to 1 segment. So, Brad, it gets the right message at the right time in the right channel with the right offer through AI, generative AI and machine learning. So, that was what we started to do. And we could do a bunch of that with generative, like we do generate content with generative AI, but we had to build our own machine learning models to really figure out this personalization stuff.

So, in 2022, we launched it, and our first product was like AI automated email newsletters, where every recipient gets their own version of the newsletter based on what they click on. It’s like having the Instagram algorithm in your inbox. But publishers, customers that make newsletters and send them to their audience were like, I don’t trust the AI. I want to approve one– so we had to rejigger it, and then we were in the middle of that, and then ChatGPT came out and I was like, “Oh, shoot, we got to go, man. Let’s go.”

So, we rebranded to Daily.ai at the beginning of ‘23, and then we launched to the marketplace. And we went from 0 to 1.5 million in ARR in about 14 months. So, it’s the first time I’ve ever launched a company indirectly into the tidal wave of a market. The tidal wave has already come and I come later. And so, it was a little bit of a new experience for me, man. It was like, I felt a different pressure. I was like, oh, man. Every minute, what’s possible? What should we be doing? Should we do an AI conference? Should we do this feature? Should we do that? And I’m like, “No, stay focused.” So, yeah, it was a fun experience. 2023 was awesome.

And what I noticed in 2022 was that, this term is pretty common now, but I learned the term multimodal, right? I heard it on a product release randomly on GitHub. And I was like, “What does that mean?” And I was like, “Oh, multimodal.” It’s going to start off as text and then voice and then video, and then it’ll be 3D worlds or whatever, four-dimensional worlds. And I was like, “Interesting.” And I was like, “Okay, well, if that’s true, and that seems reasonably true, then our product maturity arc can follow that same thing,” right?

So, then we just place bets. Well, how soon will audio be at five nines in quality? How soon will video be at whatever quality is necessary to achieve our objectives, where maybe I can send– like today, it’s possible, I could send Brad, if he goes through a demo of ours, a voice note that says, “Hey, Brad, I love the Easy Pay Direct, just thinking about Daily.ai. I am so glad you looked at our product. My name is Joe. I’m the CEO. If you have anything you need for me, man, you just reach out to us anytime. I’m here to support you.” And then AI could make that whole thing. And if you didn’t know me, you’d never know, right?

Or someone could speak that and it could sound like me. So, voice is there, but when will video be there? So, that was our mental model for where’s the putt going. And I said, “Okay, cool.” As long as we’re like at or right before the wave when it hits, like when the technology and the capability get there, we’ll be able to deliver this into our customers as fast as we possibly can. So, how can we build the rails, where it’s just okay, the LEM is a little bit better. Boom. Flip that in there, right? Gemini just came out. Boom. Get access to that API. We got everything ready. We have all the code written. Okay, they just turn on that new functionality. Bam! Build this, ship it, fly it. How are they responding?

So, that’s how we think about innovating in this game of AI where it’s like, dude, everybody’s got more money than us and everyone’s trying to get on in the game. We’re just like, all right, how can we prebuild the machine learning models that can ingest this new multimodal capability as it comes out, so that we can be the first to market with something really, truly incredible for our customers?

Brad Weimert: Dope.

Joe Stolte: Yeah, it’s fun, man.

Brad Weimert: Well, let me ask you some general questions about AI. And it’s always tempting to get tactical with things because I’m like, what can I do right now? But that’s also the stuff that despite the fact that a lot of entrepreneurs want that, and I think there’s this interesting disparity around the narrative that entrepreneurs want freedom and independence and variety and what I believe to be the reality is, we really want people to just tell us what the f*ck to do because we have decision fatigue and don’t know what direction to go and don’t have confidence or a concrete answer. Anyway, what do you think people should not be using AI for today, in June of ‘24?

Joe Stolte: When you say people, you mean business owners and entrepreneurs?

Brad Weimert: Thank you, yeah. What do you think business owners should not be using AI for that they might be trying to use it for right now?

Joe Stolte: I can say what I think is useful for us and extrapolate it, like, at our company, the mantra is outcomes over outputs. Anybody can go into ChatGPT and get an output. That’s awesome. You get that novelty rush of like, oh my God, I’m talking to the super intelligent thing, and words magically appeared and I got this really mediocre blogpost that I haven’t realized is mediocre yet because I haven’t tested it. And I’m so enamored with this magic that I’m forgetting all the stuff I know, which is, like, the majority of everything I do in the marketplace is going to fail, so I have to test it. So, test it, man. I think what people maybe should focus on is what’s the outcome and how does this thing move the needle in my outcome. So, is it better, faster, cheaper? And if so, how do I know what quantifiable metric am I measuring to make sure it’s moving the needle?

Otherwise, it’s just a novelty and dopamine kick. And you can get that from watching Netflix. You might as well be intentional about watching your favorite movie instead of farting around thinking it’s going to turn your business into this, like, behemoth. There is something said about getting up the learning curve. So, do use the tools, play with them. I think about AI in two ways. One is I think about it like a really, really, really good intern. And I would never ship intern work to the marketplace. So, it always needs a human touch. And I think about it is as transformative as electricity. Anything that didn’t have electricity that now has electricity will also have AI inside of it.

So, what’s the implication to your business? Get involved, like learn at whatever pace you’re comfortable with and try to play around, but do it in a way where you can get your teams and your capabilities and your strategy aligned up to move the needle, the outcome in your business. And that’s a very healthy way to approach AI. I don’t think there’s a wrong way to do it. I think the wrong way to do it is probably to stick your head in the sand and then pretend like it’s not coming, because that would be like, hey, electricity just came out. When is it a convenient time to put electricity in your business?

And I get it if you’re not like a “techie” or technology person or this is all very overwhelming. The funny thing is, is if you have real world human intelligence and you have mental models or you’re way up the experience curve in some area in your industry, you actually have an advantage for using generative AI because you just have to learn how to talk to it. If I’ve been in the real– we were at the family mastermind and I did a breakout room, right? And someone was asking me, “Well, what can I do with this?” And I was like, “Well, what do you do?” And he’s like, “Well, I’ve been in real estate for 25 years and I’ve done hundreds of millions of dollars and then thousands of deals.” I’m like, “Amazing,” like, take all of that and then go have a conversation with AI because you can start having a really engaging conversation on, I don’t know, like cost segregation, fairly complex stuff that you find a second nature, and you can start going deep with the model in a way, like a beginner in real estate can’t, that maybe really loves AI. So, you have all this knowledge that you can bring to the party if you just learn how to play the instrument a little bit.

So, I think the biggest mistake is putting your head in the sand and thinking this isn’t for you, because some of the smartest people that have the best knowledge and the most experience gain the most from just blurring the basics, man. So, that’s probably the wrong way to use it. And I think just getting high on the novelty of it is another rabbit hole that I see a lot of people getting stuck in. They make big strategic decisions in their business to reformulate their marketing and everything you’re doing in sales to try to AI-ify it and I commend the nature of that.

But dude, as a marketer, rule zero for me is if the pipes aren’t broken, don’t fix it, man. Pushing money through, be careful. Like, test it. Test it a little bit. Keep those pipes flowing, man. Like, it’s pretty ballsy to take something where the pipes are flowing and you’re like, you know what? I’m going to build a whole new mousetrap over here. It’s like, ooh, test it. Make it work small and then go big.

Brad Weimert: Yeah. I mean, for me, one of the general guiding principles in business is look for the lever, and the lever is almost always not the thing that’s already working. It’s usually an area that’s not working well at all, right? Because that’s the low-hanging fruit. If something’s not working very well, then I can look at a significant gain, not an incremental one, right? If your machine is humming, then you start to look at, where can I get incremental gains? But like for most entrepreneurs, there’s still significant low-hanging fruit to create a big lever. And that’s not replacing your sales force with a robot, probably. 

Joe Stolte: Yeah. Not today. Not right now.

Brad Weimert: Not today.

Joe Stolte: There’s other parts in your business like if you’ve got like a team of more than one or two people, that’s like, okay, cool. Like, you could look at YouTube and learn how to build a custom GPT to have your EA really automate your calendaring. Or you could just chat with like a version of ChatGPT that’s personalized for you and knows your calendar. It’s like, “Hey, when can Joe meet Brad for another podcast? Give me three dates that are the soonest,” and then it’ll just tell you. You know, they don’t have to fart around.

Like, there’s really productivity things you could do inside the business that are like safer places to do that like HR and finance and administrative work where you could totally automate the piss out of those, and you actually get some material time savings for your staff and level them up where you don’t have to put your revenue at risk, you know? And yeah, you can write copy and, yeah, you can do a bunch of things but I still think the best place to get AI leverage in sales and marketing is to go use the battle-tested AI that’s called Google and Meta. They have these clairvoyant machine-learning models that seem to be able to help people print money. Like, go get better at that before you completely redo your sales process with generative AI because that’s a bit risky.

But, yeah, I think start in the back office, man. Start backstage. There are so many things with AI and so many tools you can implement to materially save time on the backstage that I would start there before I moved into the pipes where the money flows. 

Brad Weimert: Well, I know we’re coming up on time here. So, a couple of other quick ones. What advice do you have for a 25-year-old entrepreneur starting today? 

Joe Stolte: Yeah. Well, this is counterintuitive and not obvious. I’ll say two things, the thing you don’t want to hear, that you need to hear, and then maybe something will actually help you if you’re stubborn like I was is if you’re 25, you have a lot of runway. Like, a lot of runway in terms of like peak energy. And just as a species at the time of this recording, we haven’t quite cracked infinite energy for the rest of our lives. But you’re basically young and invincible. You can get hammered, wake up, and drink a Red Bull, and you’re fine, right? Like, if you can actually use these years in your life to get under an amazing leader, even if that means humbling yourself and going to work for them, even though you know in your heart of hearts you’re an entrepreneur, but you find an incredible leader and you go pour everything you have into whatever it is they want you to do for a year or two, you will shave so much time off the experience curve as an entrepreneur.

You will save so many times getting punched in the face. You will glean so much wisdom on how to leverage like other people’s time, which ultimately is the game of business. Money’s a huge part of it but leveraging other people’s time and capability and skill. So, if you can get around a great leader and just absorb what they’re great at, you will shortcut so much of your journey. It’s so much better than a mastermind. It’s so much better than a course, and it’s so much better than paying for a coach. Just absorb an amazing leader for at least a couple of years, 18 to 36 months. I’m telling you, you probably don’t want to do that, but that will change your life, right?

Beyond that, I would say, there are so many pieces of advice I would give someone. If you’re like, “Screw it. I’m just going to go out on my own,” I think the biggest strides I’ve gotten is from humbling myself and just being like, “I’m the village idiot, man. Help me.” Brad, you’re great at that, “Help me with this.” Like, we were just talking about payments and, like, I know enough to be dangerous, but you’re God mode there like, “Help me.” Like, just saying, “Help me. Help me. Help me. Help me.” I think when I watch a lot of early entrepreneurs do that are very capable, they get a little bit too much entitlement too early.

They have a little bit too ego or they’re a little bit sensitive and insecure and they mask over that with this like hard shell, which is cool. I get it, man. Like, we’re all on our journey. You’re still learning how to wear the pants of entrepreneurship. It’s kind of like you’re a kid but put your dad shoes on at the front door and, “Hey, look at me. I’m daddy.” Like, you’ll grow into those shoes and you’ll grow a lot faster if you just ask people for help and like legit ask for help. And you can do that by paying people in masterminds and getting a coach, I support that. Get everything you can from everything you’ve got. Like, I learned that from Jay Abraham 25 years ago.

That being said, dude, just being humble and meeting really intelligent people and not being afraid to be like, “Hey, man. Can I ask for your help on this?” Use the H word. Will you help me on this? It’s a big ask but you’d be shocked how many people that are farther up the football field will be like, “Hell, yes, I will help you.” Because I remember what it was like when, A, I couldn’t ask for help or, B, no one would give me freaking help. And you miss 100% of the shots you don’t take. So, like, there’s a million things I could say and I want to say, but I think the best thing is to just get comfortable asking for help because you are going to need a lot of it all the time for the rest of your career, and that’s a muscle worth building. 

Brad Weimert: Yeah. I definitely echo that sentiment. I mean, I’m very good at learning from my own mistakes after I’ve made them a bunch of times in a row. I’m not very good at learning from other people’s mistakes. And when I think about the biggest mistakes that I’ve made, the first is not working for somebody else and learning from them. You are 100% right. I would have shaved ten years off my f*cking journey if I just watched somebody else do it and learn the lessons from them. Number two is if you walk into a room and your ego is in the way, you’re not going to learn sh*t from anybody.

And if you walk into a room humble and immediately talk to the smartest people in the room and say, “I don’t really know what the f*ck I’m talking about. Can you explain this to me?” you’re much more likely to get an honest, helpful, thorough answer. And the other thing that usually comes out of that is because you set the bar so low to these potential mentors, presumably you’re not an idiot doing this, but maybe you are. But you set the bar so low that anything makes you actually look like you know more than you do, as opposed to coming in and posturing like an expert almost no matter what, you’re not going to be impressive if you set that standard and you’re not going to come off well and build the relationships that you need to learn. So, I love that advice. 

Joe Stolte: 100%, dude. Like, I think what we do when we go from like middle school to high school is we like want to be cool and we want to fit in and we all just become who we need to become to be accepted because we’d rather do that than be rejected. And then we never quite kind of get out of that mode. And that leaves this weird residue as you become older and you’re a 25-year-old entrepreneur. Like, I think it’s much more useful to just go into those situations then I walk into a big room and I’m just gratitude right off the bat. I’m so thankful to be here because gratitude is like the universe is an infinite energy source.

If I can get into that space, I get energy that’s positive to work with and then I go right into curiosity. What can I learn? Who can I help? But even before then, like, what can I learn? Like, when I went to the family, that’s not my world. And I met Matt Andrews and the Family is an amazing mastermind for real estate professionals and other great people, too. I’m fairly versed in real estate, but I don’t know anybody in that room. I knew nobody, and I was just like, “Oh my God, I’m so thankful. Like, farm kid from a town of less than a thousand people. How did I end up here? This is cool.” And then I’m like, “Well, who’s here? Like, who can I learn from?”

And I don’t come in like I’m a five-time founder with three exits and I’m just like, “Oh, dude.” Like, I’m here to actually help get some partners for my business but I’m also like, “Look at all these people that have crushed it in the best asset class on the planet.” Like, I just want, who can I meet? And the first person I met at the Family was Jay Conner, and he was such a cool dude, and he became one of our customers. But I was like, “This guy’s on fire.” And he’s infectious and I’ve learned a lot about private money lending from him. That’s not why. I didn’t go in the room like, “Hey, let me sell my sh*t.” Although in the back of my mind, I was like, “Eventually I’d like to sell some sh*t to make this trip worth it.”

But I’m going to come in with that gratitude and then I’m going to shift in that curiosity. Then I don’t come off as a prick or an inauthentic weirdo. I’m just kind of like, “Okay, cool. Like, I’m normal and chill and I don’t have to be somebody I’m not. I’m just curious Joe and I want to learn.” So, that frame for me has been, dude, it’s been like a cheat code. I don’t have to be the chess beater. I just walk in as the village idiot. And then when people, if you want to edify me and put me on stage, I’ll go into performance mode, and I’m happy to do that but that’s not where I started. 

Brad Weimert: That’s great. Yes. Family Mastermind is an awesome group. Jay Conner’s a client and also awesome. Huge fan of him. Well, Joe, par for the course here, and shouldn’t be surprising to me, but I have like 800 other questions for you and no more time. So, in the meantime, until we actually get you in studio for those other 800 questions or just hang out, where do you want to point people? What do you want to direct people to? 

Joe Stolte: Yeah, I think if you are interested in learning about AI and you’re interested in learning about kind of where AI intersects with marketing, and you want to have a newsletter at all or email newsletter, you can follow me, @joestoltelive, on Instagram and then just DM me the word ‘AI,’ the two letters AI, and I’m happy to point you to some resources, free or otherwise, that can help on your journey with AI, especially at the intersection of AI and marketing. And then in that same conversation, if you want to learn about AI automated email newsletters, I’m happy to point you towards Daily.ai. But if you need a resource in AI and you’re looking for a place to get started, just DM ‘AI’ on Instagram, @joestoltelive. I’d love to help you out. 

Brad Weimert: Love it, man. Well, I’m going to do my best to dig up some videos of you breakdancing and post them somewhere. 

Joe Stolte: I’ll send you a few. 

Brad Weimert: Yes, that’d be amazing. That’d be amazing. And, yeah, it’s great, man. I appreciate you carving out time. Until next time. 

Joe Stolte: All right. Thanks, Brad.