
Loading summary
A
HubSpot is a success story, partner. Now think about listening to this podcast. Right now you are probably multitasking. You are probably catching maybe 70 to 80% of what I'm saying. Now flip that and imagine catching only 20%. It's not a good use of your time. That'd be insane, right? But this is the reality for most businesses. Most businesses only use 20% of their data. That's like reading a book with 80% of the pages torn out. You are making decisions with a fraction of the picture. All the important details that get buried in the call logs and the emails and the transcripts and the chat messages, and it's just floating around doing nothing for you. Unless you use HubSpot. Their customer platform brings all that unstructured data together and turns it into insights that actually help you grow your business. Because when you know more, you grow more. And when you're running a business on a hundred percent of your data instead of 20, the decisions get a lot easier. Visit HubSpot.com to get the full picture today in this lessons episode, explore how entrepreneurs can choose the right business by aligning opportunity with long term goals. Discover how different growth stages demand different strategies and leadership. Understand why building for longevity often requires resisting short term pressure. And uncover how the best founders embrace hard problems as the path to lasting success. Okay, so a lot of corporate experience all makes sense now. I heard something that is interesting to me. That's a great entrepreneurial lesson you mentioned. Some businesses are not the right kind of businesses. And we'd argue like, if you can build a business to $100 million, that's a great business, but it wasn't the one to go to a billion. But let's, let's shelve that for now. I have a different question. When you're starting something new, what is the right business? Business. So if you're an entrepreneur and you're getting into it for the first time, how do you decide where to spend your time?
B
For the person starting it, it's the business that accomplishes their goals. At the time, you know, Austin's goal is to run a billion dollar company. So he started Picasso accomplished that goal. That was a realistic goal. So to sort of have this hybrid between realism and surrealism. You know, it's like, yeah, I know I could build a million dollar company. And even now it's funny you mentioned Austin because with Dot Loop, I'm sort of at a similar point with Curator, my own company because, you know, we basically sprinted to a certain size. We're Private. So the numbers are not out there the way venture capital backed are. But we're private. We're profitable. We got cash. We do a million a month in mrr. Like, we're a great business. But the way that it is built today, it does not lead to a billion because Commissions Inc. And Tiger Leads and Boomtown. We've seen the comps for what we've built, and the comps are at about 352, 250, maybe 500 million. That is the highest. Then we looked and we said, okay, who are these brokerages that no one's heard of that everyone makes fun of, that kind of suck, and they're kind of new, and they're not even really doing things that well. How are there, like six of them worth a billion? And there's not one SaaS platform worth a billion? So I'm. I'm swimming in the wrong stream. So. But I can't become a brokerage because all of my clients are with all the brokerages. You know, I'm Switzerland. It's important to me, by the way. So it's hard. And so to pick the thing up off the tracks and go build the business of tomorrow while you're working on the business of today, it's a lot harder than it sounds. And the key is just having great people around you. We. We were never able to look too far into the future when we were caught up in the weeds.
A
Okay. So now let's sort of walk through the entrepreneurial journey. And when you started, when you started Curator, when Austin started Picasso, there's Playbooks you deploy, there's playbooks for your product market fit. First 50 customers. First 100 customers. From 0 to 1 million. From 1 million to 10 million. From 10 million to 100 million. So walk me through the playbook for getting a company off the ground.
B
I want everybody to get the best advice possible. I've built a company like that. I have great opinions on it. But there's a guy named Jason Lemkin. He is the, I believe, the smartest person when it comes to growing a SaaS business from 0 to 10 million in ARR. Because the reason I say that is as I'm on this journey with Jimmy and as I'm working with Austin and going through all these ups and downs, I feel like he's speaking directly to me and he's never met me. He's talking about my problems, he's talking about my issues. He's basically like, reading my diary on Twitter. I'm like, dude, how do you have my piano? What are you doing? And he showed me that he knew me. And so I then really latched on to him because he could get me where I needed, where I knew I could get next. See what I'm saying?
A
Yeah.
B
But what I love about him, too, is he's like, I ain't the one that gets you from 10 to 100. And the person that gets you from 10 to 100 is probably not the one that gets you from 100 to a billion. So don't get romantic about the who or the how. And so for Jimmy and I, we are not driven by financial gain, which, ironically, allows us to play this sort of Simon Sinek infinite game. And so, as opposed to some of the other founders I've seen sort of sell, move on, you know, leverage to. To level up. We've. We've chosen to pivot. We're like Ross on Friends. We're pivoting. Pivot, pivot, pivot. Because we know that we are talented enough. We know that our team is good enough. We know that our ideas are smart enough that we can be bigger and better, way bigger than we are today. When we see companies that are bigger than us and founders that aren't as good as us, we don't stop. We just keep going, you know? But that's how we're driven. I can promise you 98% of the people that started Curator would have sold it already, and they'd probably be, like, building an island somewhere, you know, like. But that's not how we think of success. We love the work. I heard a story. Let me tell you a quick sports story.
A
Yeah, go for it.
B
There's been one flagrant foul in the history of the NBA All Star Game, and it was Dwayne Wade accidentally fouling Kobe Bryant across the face. He broke his nose or broke his cheekbone. Blood was gushing out. And, you know, it's the All Star Game. These guys are. Half of these guys are friends. Well, two nights later, the Heat play the Lakers. And so D. Wade's a little nervous because he never really got to tell him properly that he was sorry. And Kobe comes out, and he's got this mask on, you know, the. The sort of Mamba mask. And D. Wade goes up to him, you know, before the tip off, as. As the game's about to start, he said, hey, man, I'm so freaking sorry. You know, you. You know, it was an accident, but I felt like I just needed to say it again. And he said Kobe looked at him dead in the eye. And he said, I like it. He likes it. He liked the twist that he had to play injured because that's different and it's unique and it's experience now that he can go through that other people haven't, that he can learn from, that he can go show his highlight films. Just like LeBron wearing the mask on the Heat. We've got some Kobe mask games. People that reach the ultimate scale. They are fascinated by solving problems. So if you're building your situation where you're problem free, tough to get all the way to the top because you have to be willing to tackle problems people won't or that they aren't. And so for Kobe, he's just like, this is cool. Tie my hand behind my back. You know, I'll close my eyes on a free throw, right? That's a new challenge because the regular game is easy now. And so I'm trying to level up from there. Leveling up from where Kobe was with shit like playing with a broken face.
A
Upwork is a success story partner. Now one of the biggest lessons I learned building businesses is that you don't have to do it all yourself. The fastest growing companies, they are not working harder, they're delegating smarter. And that's where upwork comes in. Upwork is a one stop platform to find, hire and pay expert freelancers across web and software development and data and analytics and marketing and business operations and more. We're talking over 125 categories of specialized talent. So wherever the skill gap is, you can fill it fast without weeks of recruiting or committing to a full time hire. You can browse profiles, review past work and get help scoping the role before you ever spend a dollar. And with Business plus, you get access to the top 1% of talent on Upwork and with AI powered shortlisting that matches you to the right person in under six hours. Contracts, payments, all handled in one place. It's free to sign up. Job posting is super easy. Visit Upwork.com right now and post your job for free. That is Upwork.com to connect with top talent ready to grow your business. That's up w o r k.com Upwork.com LinkedIn ADS is a success story partner. Now have you ever spent money on something that you were sure was going to be worth it and it just wasn't? Because we've all been there. I've done it more times than I like to admit. And marketers do the same thing you spend on ads. The impressions look great, the reach looks Great. But then nothing turns into revenue and now you have to explain it to your Boss or your CFO or your CEO. LinkedIn calls this bullspend. Now here's what's worth knowing. LinkedIn Ads generates the highest ROAS return on ad spend 121% of all major ad networks and you can target by company industry job title so you're actually reaching buyers, not just eyeballs. Cut the bull. Spend advertise on LinkedIn. Spend $250 on your first campaign on LinkedIn ads and get a $250 credit for the next one. Just go to LinkedIn.com ScottClary that's LinkedIn.com ScottClary Terms and conditions apply. Framer is a success story partner now you could be a solopreneur. You could be an entrepreneur. You could be somebody just sitting at home who's trying to start a business out of their house. But you know the drill. You need good design to create a website to get your business off the ground. But good design is expensive. And you can't afford to hire a designer for every single landing page. Social posts but you also can't afford to look amateur. And I've been there. You need to move fast, you need to look professional. But you also need to not blow your budget on five different tools. Framer already built the fastest way to publish beautiful production ready websites. And it's now redefining how we design for the web with the recent launch of design pages. A free canvas based design tool. Framer is more than a site builder. It's a true all in one design platform. From social assets to to campaign visuals to vectors and icons, all the way to a live site. Framer is where ideas go live, start to finish. And the best part is it's actually free, not a trial free. I'm talking unlimited projects, real vector tools, 3D transformations, everything you need without the nickel and diming. So if you're ready to design, iterate and publish all in one tool, start creating for free@framer.com design and make sure you use code success story for a free month of framer pro. That's framer.com design and use promo code success story framer.com design promo code success story Rules and restrictions may apply. You know, now you made an interesting point. You said when you're building out curator, a lot of people would have sold it before. Now there's a lot of people that would have built it to sell. So when you're building a company and you want to build something that has some longevity and lifetime and legacy to it. It seems like that's what you're doing right now. You want to test out different things. There's a lot of pressure from external stakeholders because a lot of entrepreneurs, they bring in VCs, venture capitalists, investors, and there's a timeline, there's a ticking clock before they have to have an exit event. So you want to build something long term. Does an investor have that same shared opinion? And I guess the question would be for a founder, if they want to take that pressure off, they want to build something that could be more of a lifestyle, how some longevity to it should they work with venture capital investor outside money that's going to put all that pressure to expedite everything?
B
No. You know, I wore this sort of anti Silicon Valley, anti venture capital hat for a while, similar to the guys from base camp, where it's like, hey, there's another way. You don't have to do it this crazy way that Silicon Valley does it, like be proud of, you know, being profitable as an example, like things like that. Yeah. And simple stuff. I actually, as I've gotten a little bit older, I just, it's kind of back to that example we just gave. There's a lot of ways to do things and I don't know how to do it the Silicon Valley way. And that actually now bothers me, Scott. I'm now basically saying the thing I made fun of for 10 years. That's actually the thing that I need to understand better if I'm going to continue to be the best marketing sales professor in the world. Because it's incredibly difficult to keep up with this stuff. I got a push alert yesterday. Google Optimize going away in 2023. I'm like, dude, that's in my book. I can't unprint my book. But I know that going in. So anyway, I hope that makes sense. I wanted to follow up one point about who to onboard though. You know, who do you onboard? Who do you off board is a really interesting question too, because there's these people that like push you up the mountaintop and they, they follow you like a disciple. They really do. When you have a great culture and you have a great mission and you have, you know, founders that are passionate, like it's sort of a good culture, right? It's awesome. There's words, there's colors. Like they're like, it's. It's a real thing. It's amazing. It's hard to replicate. But that startup phase has to change to continue to scale. So all of a sudden you've got these people that pushed you up to this huge mountain that you're grateful to have ever seen the top of and you're starting to realize that they're the wrong people to help you go up the next mountain. And so that change management is tricky, you know, because you've got all these people that got you there but you know, they won't get you here. But you're not going to just lay off all your best people. It's, it's hard. And so to me, you need to have some sort of unemotional line in the sand where we are going to be, you know, founder led, service led, passionate. When we hit these numbers, we are going to then go find experts like this to help us do this. If that was clearly defined on day one, people would know which exit ramp they wanted to take. But who knows what's going to happen with a company. We could have gone bankrupt several times. So like they don't even, like they're buckling up, but they don't know for how long.
A
Thanks for tuning in. If you found this valuable, don't forget to hit that subscribe button so you never miss an episode. And if you want to dive deeper into this conversation, check out the links in the description to watch the full episode. See you in the next one.
Air Date: May 6, 2026
Guest: Chris Smith
Host: Scott D. Clary
In this episode, host Scott D. Clary sits down with Chris Smith, co-founder of Curaytor and author of "The Conversion Code," to unpack the lessons learned from building an eight-figure business without raising outside capital. The conversation delves into how entrepreneurs can choose the right business based on personal goals, match strategies to each stage of company growth, navigate the challenges of building for longevity, and the necessity of embracing hard problems for lasting success. Chris shares candid insights from his own journey, reflecting on leadership, startup culture, and why he and his partner resisted quick exits, opting instead for sustainable impact and continuous growth.
This episode offers a deep dive into lessons from Chris Smith’s unconventional success, including why founders shouldn’t just do what everyone else is doing, the necessity of loving the hard stuff, and how your definition of success—as well as your team and strategy—must evolve as the business does. The tone is honest, pragmatic, and motivational, full of actionable advice and engaging stories for entrepreneurs at all stages.