How Writing a Book Can Add Revenue Streams and Millions to Your Business with Chandler Bolt – EP 268

Justin Donald: Well, Chandler, so good to have you on the show. We've been talking about doing a show for literally years now, I think.

Chandler Bolt: Yes.

Justin Donald: So, I'm glad you're here. Glad we could do this in person. Makes tons of sense, obviously, with you here in Austin as well. But I guess last time we hung out, we were at, what is it? Where were we? Is it ATX Cocina downtown?

Chandler Bolt: Gosh, maybe so. Was that Dan Martell may be in town?

Justin Donald: Yeah. Dan Martell's event.

Chandler Bolt: His pickleball.

Justin Donald: Oh, that's right.

Chandler Bolt: At the kitchen with, gosh, Clay. And oh yeah, Grant Baldwin was in.

Justin Donald: Grant Baldwin. Yeah. Shout out to those guys. I'm actually going to have Clay on the podcast.

Chandler Bolt: We call them your biggest losers, but yeah.

Justin Donald: By the way, for those of you that don't know, this man right here, Chandler, is a great pickleball player, has a court at his home that he built, and still waiting to play over.

Chandler Bolt: Makes me sound better than I actually am. We got to play at the court, honestly.

Justin Donald: I do, I do. Well, that'll be fun. Hey, I'm just excited because you built a business around helping people brand, and I think that this is important for so many people. We're in a day and an age where having a personal brand, having content that you're putting out can really create a cool lifestyle. And I've seen it. It's been evident in my life through the Lifestyle Investor brand, the book, the podcast. And so, I want to talk about this because your business is helping this for anyone. I talk about a couple of the most impactful books that I've ever read, one of them being the Almanack of Naval Ravikant, and he is big on creating content, branding, things that live beyond you, somewhere else that can get attention when you are not doing anything, right?

It's like today's new form of currency. And I'd love to hear your thoughts around that because you specialize in this, your business, Self-Publishing School, like you guys have Self-Publishing.com. You guys have been one of the fastest-growing companies in the Inc. 5000. You've written a ton of books with and for people. And so, let's get into it.

Chandler Bolt: Yeah. I mean, I think to your point, if you have a business and you don't have a book, you're leaving millions of dollars on the table. I mean, let’s take it even back to you, right? I remember Lifestyle Investor, reading your book as I was getting into investing, and it was crazy helpful, and I think that's just like a classic example of the buyer journey, what it can be once you have a book. A book is better than a business card because people don't throw it away, and it's a deep, meaningful connection with you. They read the book, and then they go on to do business with you. And so, it's like even just thinking about like I had no context of you. I'm sure you had no context of me.

I remember we met at - it was some random Justin Goff’s party at his house. And I remember that was the first time we met, and we had a bunch of mutual friends, Hal Elrod, and a bunch of other people. They're like, "Oh, you got to meet Justin.” But then we briefly met there, and you're like, "Oh, let me grab a book,” and you gave me a book. And then I read that book and I was like, "Oh wow, this is really good,” reached back out and then we ended up hanging out and seeing each other's events. There's a bunch of stuff since then. But that book was the difference between us briefly meeting and maybe never seeing each other again. And I'm like, "Oh no, this is now a deep meaning. I feel like I know this guy because I read his book. This is super impressive.”

And then just the collision that happened from that with Grant Baldwin and Michael Hyatt. And then multiple people in my world are like, "Oh, hey, I'm doing some investing stuff.” It's like, "Have you talked to Justin?” It's just like I think that's just a perfect example of it.

Justin Donald: For sure. And actually, we would probably not be friends today had I not had a book, had that not been the opportunity that really drew us together. And then it's really cool, like having a book, you get to know so much about me without even knowing me. And for me, same thing, when I read authors, I'm like I get to know those authors. I have a relationship with them before I actually have a relationship with them that actually makes me want to have a relationship with them, you know?

Chandler Bolt: Yeah. And leverage at scale.

Justin Donald: Yeah. And someone told me this early on. And I thought it was just the biggest line of garbage, but they said there's life before being an author, a published author, and then there's life after being a published author. And I was like, "Get out of here. That is baloney. There's no way.” Sitting here today, I will tell you unequivocally that is the truest statement I've ever heard. I had no idea the difference in like authority, like inferred authority. It's absolutely crazy. So, I always tell people, "If you're going to write a book, write a good book. But if you have a book that's a bad book, you are still an industry expert to some niche or some genre of people. You have elevated your clout, your status, your expertise. And then when it's a really good book, I think you are able to do things that, from a business standpoint, a branding standpoint, that you would've never been able to do. Would you agree?

Chandler Bolt: Yeah, I agree. I think, to your point, I remember I interviewed Brian Tracy one time, and he said, “I would say there was life BB and AB, before book and after book.” And it's so true. I mean it changes everything. We always say this is kind of like the key that opens the door to Narnia is like all these opportunities that really exist for published authors. And there's a reason why New York Times says 81% of people want to write a book. We know less than 1% of people actually do it. Well, when you do it, you become an authority because you're the 1%. And the root word of authority is author. You can't spell the word authority without the word author.

Justin Donald: I love it. Yeah, that’s fantastic. So, why would you say every entrepreneur, like what are some specifics? Why should entrepreneurs and investors? Our podcast audience is generally going to be entrepreneurs, investors, and then often a lot of people in the W-2 world that are looking to transition into the entrepreneurship and investment world. So, why should they consider this? Why should they consider working with you?

Chandler Bolt: Yeah. I'd speak to each of those groups individually, and it's kind of a lot of overlap, but the entrepreneur you write the book to give you leverage. It brings in lead sales and referrals. And it goes from one-to-one to one-to-many, right? But then the investor, you write the book on your investment philosophy to bring in investors, and then maybe to open up an education arm. That's where a lot of people that we've worked with have done. They teach their type of investing in the book, give away all your best stuff for free. People will pay you to tell it to them again. So, it's kind of like the teach me how to do it, show me how to do it, do it for me.

They use the book as to teach me how to do it. Then they show me how to do it as some sort of coaching course, mastermind, et cetera. The do it for me is I've got to fund, right? So, that's on the investor side of things. And then the W-2, it's to give you leverage. Maybe it's to start a business, maybe it's just income that you want to create. But either way, it's really a leverage.

Justin Donald: Yeah. And think about it this way, like if you have a book, you're going to get speaking gigs. You just are. It's hard not to. I've had so many people reach out that I had no clue who they were, what their group was. Like, it's just going to happen. So, there's extra income opportunities for people who are looking to do that, right? For me, with the Lifestyle Investor, I mean, not only has it helped create this epic mastermind, and really just this funnel of amazing people that we get to do cool stuff together, travel the world, do collaborative learning, and tech strategy and investments. But early days for me, I had to go out and find all my investments.

Well, now with the Lifestyle Investor book, people are constantly reaching out to me. Now, that means that there's a whole lot more I have to kind of sift through, but it is nice because we have gotten a ton of killer deals.

Chandler Bolt: I was going to say deal flow.

Justin Donald: Because we're out there, because people know of it, because people know of our community, and it really has been a game changer.

Chandler Bolt: And down deal flow, which champagne problems, right? That means you got more deals to review.

Justin Donald: That's right. That's right. No doubt.

Chandler Bolt: I'd rather inbound deals and a lot more deals to review than no deals at all, right?

Justin Donald: Oh, without a doubt. So, how do you choose what someone should write about? Like, how would they choose? If someone listening to this is like, what direction should they go in? How do you help them get started?

Chandler Bolt: Yeah. I mean, I think the first question I ask is, what are the broken record conversations that you're already having in your business? A lot of times, I think CEOs feel more like a parrot than a CEO. You keep repeating yourself. So, what are those things you keep repeating? What are the questions you're always getting asked? I mean, in my mind, if you're using the book to grow your business, it's got to directly relate. So, I think about the four Ps of a bestselling book, but then this also ties into your… It's like who's the person that you're writing it for? What's the pain that they have, that they know that they have? What's the promise that you can help them with in this book? And then the price point, which is pretty straightforward.

But I would align that in the book and then align that to the business. And that is when I see books really drive a lot of business. And I'd say the riches are in the niches, like as niched down as specific as possible, the better.

Justin Donald: Yeah. And by the way, I should also say, like anyone watching this or listening, I've actually sat through some of your programming, some of your coursework. I haven't done your full workshop, but I've done some of your partial workshops. I've heard you speak. You're a great speaker, you're an industry expert. You're really great at what you do. You're also great at helping take a complex thing like writing a book and actually simplifying it, so people can get started. I've sat in rooms where you have done that. You're very good at that. What do you say to the people that are just too busy to write a book? I feel like that has to be one of the number one excuses for me. That was my number one excuse early on.

Chandler Bolt: Yeah. I mean that's the biggest excuse is people think either, “I don't have the time,” or, “The timing isn't right,” which is really just a disguised excuse to just keep putting it off. There's never going to be a perfect time. You have to get started before you're ready. I mean, it is a short-term sacrifice, but you create a long-term asset, and that's the biggest thing that I think most people don't understand because they either don't grasp it or they don't do it correctly. So, they think, "Oh yeah, it's just a book. Like, it's not going to really do anything for the business.” But they don't realize how much money they're leaving on the table by not doing it.

And so, that just means you've got to short-term make some sacrifices to create this asset that exists forever. And if you do it correctly, I mean, you know, years ago you published your book. I'm sure to this day you're getting deal flow, you're getting customers, all that stuff. And so, it really is this long-term asset.

Justin Donald: Yeah. And I'm still shocked because generally with a book, they kind of say like in that first week, weekend, a week, maybe even first 10 days is the most you're ever going to sell. But we just keep on selling a ton of copies. So, it's like gain traction, like I'm just still blown away how many people are buying it. And then we had this really cool experience, because I started working with some pro athletes. So, in the mastermind, we've got this amazing guy that I absolutely love. Chris plays professional football in the NFL. And I had another guy in my podcast, Devon Kennard, who had read my work and had been following the podcast for a while and was starting to put some of these deals in place.

And he started building all this passive income to the point that he didn't need to take his next contract. He was able to transition into becoming an investor, which is really cool. So, I got to go to the ESPYs this year and speak to a bunch of the pro athletes, do like a day of passive income and wealth creation, which was really cool. And then in Hard Knocks, so another reason why, like, it's nice having a physical book laying around HBO's, one of their biggest shows, Hard Knocks, which follows the preseason of one of the NFL teams. This year is the Buffalo Bills. Well, we've been talking a lot with Damar Hamlin, who is just an awesome guy. His story's incredible. Died on live TV, was brought back to life, and is back playing again, which is so cool.

And he's just one of the warmest, sweetest, nicest people. We hung out with him at the ESPYs. And in this Hard Knocks episode in his room, at his desk, during this shoot of the episode that just came out, Episode 2, The Lifestyle Investor is literally sitting on his desk, right there plain as day for like a five-minute clip. And so, again, it's like it screams to the fact of like have an asset that can live out there without you having to do the work, right? It's like it's a whole reason that everyone knows what Coca-Cola is. Everyone does. Why do they still place ads on billboards and spend all the money to advertise in the Super Bowl, the most expensive place for advertising?

Top of mind awareness, right? And then just like you've got this element of actively and passively selling things. People just need to see it. And there's a threshold too for some people of like it's the number of iterations or number of impressions, and there's this tipping point where if you've seen something enough, boom, you take action, right? And so, I feel like it's the same thing with a book with content, a podcast, whatever it is.

Chandler Bolt: That's a beautiful thing. A lot of people say a book is the new business card. I think a book's better than a business card because give someone a business card, they're throwing it away within four hours, right? But you give them a book, they keep it and it's in their home, it's in their office, or in this case, it's on HBO because that book is there and it's visible. And every time they see that book, they think of you. So, I feel like that's just such a beautiful example of that at the highest level.

Justin Donald: That's so cool. It's got to be thousands of people you've helped write books at this point.

Chandler Bolt: Yeah. So, we've published about 7,000 books so far. We publish about two to five a day. So, we published two yesterday. I mean, we publish books every day.

Justin Donald: And so, how do you successfully launch a book? Like, how do you guys do that at Self-Publishing?

Chandler Bolt: I think about it as kind of, we call it the Launch Triangle. So, there's kind of these three core elements. There is a launch team, there is promotions, and there’s reviews. So, that's kind of like the three corners of the launch triangle. There's a lot more that you can and should do, obviously, but it really comes down to those three things. If you do nothing else, just create a launch team, small group of people who support the launch. That's going to help you get reviews out of the gates. And then promotions, that's kind of the accordion bucket. That's like we have in one area, it's more what we would call the traditional launch. That's like any traditionally published book, probably did this playbook, right?

Then, on the other hand, is the MVP launch, so kind of the minimum viable product launch. And really, the main difference is just the accordion of promotions. How much time, money, and energy do you have? And then do that. And then I think one important caveat to all that though is most people think about it as launch week. And I think you're a great example of not doing this is we like to think of it as launch year. So, it's just, hey, if you just do a launch week, cool. It's probably going to do nothing like most books. But if you just keep talking about it for at least a year in your example, years later, well, it's no surprise that that book keeps cranking and keeps selling and keeps bringing in customers. So, it's the launch triangle coupled with the one-year launch.

Justin Donald: Yeah. And if you want to talk about a great promotional product of a book, I mean, we just saw it on display this past weekend. Like, the timing of this episode is actually perfect because Alex Hormozi just came out with his new book. And they broke the Guinness Book of World Records for most books sold in, what is it, 72 hours or whatever. And so, previously in the nonfiction category, I think the most ever sold was 1.1 or 1.2 million copies of books, which is a crazy amount. And if you're writing a book, I don't know that you should think like, "Oh, I'm going to get rich on a book.” Most people do not. But it's the business that it can bring. But he was able to sell 3.2 million copies of his book this weekend, which is out of control.

I mean, the only books, I believe, so number one ever by like a landslide in nonfiction… Sorry, the old record is 1.1 or 1.2. So, he literally tripled that. Okay. And then the only other books out there that have ever sold more copies, even on the fiction side, are, I think, three of the Harry Potter books. So, I mean, it's like incredible. And he did $100 million in revenue in his launch.

Chandler Bolt: Yeah. I mean, that's executed at the highest level, right? Super impressive. But Alex Hormozi is a great example of someone you probably wouldn't know of without the books.

Justin Donald: Oh, for sure.

Chandler Bolt: And maybe you know of him, but maybe not so much about his business. And so, I think that's when a lot of times people are like, "Ah, why should I have a book?”

Justin Donald: That's why.

Chandler Bolt: Look around.

Justin Donald: Why should I create content? That's why.

Chandler Bolt: Yeah. Have you ever heard of Acquisition.com? Probably because of one of these three books. Have you ever heard of…? You can just rattle through kind of all these businesses, even Russell Brunson and ClickFunnels. You probably didn't hear about them until these books, right? There are so many examples of the book letting everyone know about the business. And I think Alex is a great example of that.

Justin Donald: So, I was hanging out with some of his friends last night for dinner, and I was going through, and I've got some friends that bought his big package, his once ever only that helped do this book launch, where he tied in some coaching to it. And so, I actually think the number of books was actually like, what was it? I think it was 95 million in book sales, and then it was like 10 million on the coaching product. So, it was actually like a much smaller percentage on coaching. And then I was chatting with some other people, and I guess before he kind of had his rise to prominence, he didn't have necessarily a big social media following. He was posting seven times a week, and then he increased it to 80 times a week. And that was part of that launch for him.

So, again, it's creating content, it's putting your ideas out in the world, obviously putting your ideas in book format. And I think he's done a masterful job, and I think anyone would be happy to have 1/100th of what he's been able to do. Happy with $1 million. Happy with $500,000.

Chandler Bolt: Well, it's funny you talk about the content. I mean, that's what we were talking about the way here is just volume of content. So, most people would be happy with 1/100th of where he's been, and they haven't posted 1/100th of the content he's created. And so, there is an insurer probably get crucified for this in the comments, but there is a certain element of like just ramp up the volume. I know he talks about this, I know Grant Cardone talks about this as like, "Okay, cool. Sure, you can get more traction per piece of content, or you could just create 10 or 100 times as much content.” And in that, there's going to be winners, and you're going to learn and iterate way faster.

So, just increase your inputs, and the outputs will exponentially increase. And I think that's a great example of that, both with him. Macro with his brand, with content, and all that stuff. But even micro in the launch itself, it's like I remember you said, “Hey, we did 500 iterations of ads. We spent $4 million on ads in the lead-up to this launch. Facebook, our account actually maxed out because we had too many iterations of ads.” But that is volume, right? It's not thinking, "Oh, we're just going to design the best ad and we're going to get five cracks at it. We're good. We're smart, so we'll create five good options.” It was like, "No, let's create 500,” and there will probably be five good ones in that 500.

Justin Donald: That's right. Now, how have you used books? Because I think you've published seven, right? You've got a bunch of bestsellers. Okay, so you got a couple of them right here. How have you used books specifically to grow your business so people can kind of take that in whatever direction they need to go for their business?

Chandler Bolt: Yeah, so this book right here is an example. This is my newest book. This has brought in about $7 million in sales in the last 12 months.

Justin Donald: And, if you're just listening, it's the book, Published.

Chandler Bolt: Right. Yeah, Published is the name of the book. So, I look at this specifically as how do we use the book to get more leads, sales, and referrals. So, that is kind of the three buckets that I think entrepreneurs should think in. So, more leads, more sales, more referrals. Leads, these are people who hear about your business because of your book. Sales, this is integrating your book into the sales process for more sales. And then referrals, it's giving your book to people, customers, so that they can refer you. And not dissimilar to how you gave the book to me, right? It's like you gave the book to me years ago. I now know about you and your book. I'm now referring you business.

When Michael Hyatt's asking me like, “Hey, have you ever heard of this Justin Donald guy?” I'm like, "Yeah, I have. I think it's legit.” So, I mean, and that doesn't happen without the book. So, that's kind of the referrals piece. So, for me, it all comes back to lead sales and referrals. There's a bunch of things within that, but that's kind of how I think about it.

Justin Donald: And then how do you help people? So, maybe I have an idea for a book, but I don't have a lot of content for it yet. I'm unsure. It's like I went through your four Ps, so I've got some clarity on that. Like, how do you come along and partner with me and with others to actually help them complete it? Because for busy people, their excuse is like, "Well, I don't have the time, or I'll do it later.” But you simplify a lot of this, right? And I actually want to get into ways that you're disrupting the industry after you answer this question, but like, there are ways that you help make it fun, easy. Like, you have a playbook and a process to actually help people do this. I think when I first started, I was like, “I don't know, how can I come up with this many words for a book?”

But for me, I hired someone that all I wanted them to do is ask me really good questions. So, I actually said, “I want you to come up with the best questions you can, and we're going to record it. You're just going to ask me questions. I'm going to answer them because you're going to ask me stuff that I am not thinking. It's not top of mind.” So, like for me, that was my hack. And I had tons of questions asked, and I came up with so much stuff, and I was like, "Whoa, I didn't even know that was hidden up there.” Or I actually didn't even have the clarity of delineating it how I did until I was asked that question.

Chandler Bolt: That's good. I like that. I think there are two specific ways. There's the framework and then there's how we work with people. So, the framework is, we call it the MORE writing method, which is mind map, outline, rough draft, editing. That is how we help people write better books faster. And then how we work with people is we partner with them, we come alongside them. We say, "All right. What's the plan? What's the goal? What's your book about?” to find the four Ps, all the things. We pair them up with a coach. We've got curriculum, templates, all the things that shortcut the process. Our goal is to save them hundreds of hours in the process, thousands of dollars in the process.

Then we come alongside them for kind of like this final mile of publishing. All the boring logistical stuff that you have to do to publish successfully. We do all that for them, and then they keep all the rights and royalties. So, I believe that Self-Publishing is entrepreneurial publishing, so we want them to keep the upside, and then we help them with a lot of the marketing stuff. So, how do you sell more copies? How do you integrate into your business, all that stuff? Some of that stuff we do for them. Some of that stuff we coach them through so that they're integrating it kind of really into their business. But that's the framework, and that's how we help people.

Justin Donald: That's cool. I'm excited about what you guys are doing in the disrupting of the industry because I think with the actual publishers, I actually think they run a bit of a racket, and I think they’ve been disrupted because they're trying to control too much of the way that it goes down. A long time ago, that was the only way that you really could publish, and I think that the cuts and the splits and the agreements are very egregious, very weighted to these publishers, and I think that there are a handful of companies that have really done a good job. I'm going to mention some other companies as well, because I think the way I look at it is like the more companies disrupting the industry, the better for all companies.

I look at that for masterminds. People are always like, "Alright, tell me the good masterminds and tell me the bad masterminds.” I don't want to badmouth any mastermind. I think every mastermind out there is good for all the masterminds out there, right? So, I don't see any mastermind as a competitor. I see them all as like, hey, the more we build up all these people running them and the masterminds themselves, the better reputation masterminds have, and we all thrive because of it, right? And I believe everyone should be in a mastermind. Find the right fit. What's the right fit for you? I do think figure out the right price point, the right content, the right people, but everyone should be in a mastermind.

It sharpens your skills, makes you better. There's collaborative work. So many reasons. So, I give that example because when we're going into like the disruptors of publishing, you've got these self-publishers, so you actually own what I think is the best name in the space. Self-Publishing, Self-Publishing School, Self-Publishing.com. So, I think you captured something great there. Scribe is a company that was on a meteoric rise, had some crazy issues internally, self-destructed, and then Enduring Ventures bought them. And I love those guys. Just Xavier and Sieva are just awesome. We had them at our last event. Eric Jorgensen was at our last event, who's running it now.

And so, they're building that thing into something great. You've got Charlie Hoehn who's doing some great stuff. So, to me, the three of you guys are really, and there are probably others in the space, but you're the three groups that I think are really doing a high-quality job and truly revolutionizing self-publishing.

Chandler Bolt: I appreciate that. Yeah, that's the goal. I mean, because the publishing industry is kind of a joke. It's the taxi industry before Uber came along. Everybody knows you're getting screwed, but you're kind of like, "This is the only option.”

Justin Donald: Yeah. And it's not even the… Like, so yes, you're getting screwed. Yes, there are these lobbying groups that are preventing a better innovation, a better way of doing it in, but then it's also like there's friction. It's like you get to the end of the ride, they're like, "Okay, we need you to…” Like, I took a cab the other day because a cab came when I ordered an Uber, when I was in LA, when I was at the ESPYs. And so, we get there, and I get out, and he is like, "Oh, you need to pay me.” And I was like, “Oh yeah. This seems backwards.” So, it's like I wasn't trying to not pay him. I'm just used to getting out of an Uber. So, it's like, okay, let me take all this time while you run my card, and then let me sign it. And it is just so backwards from the way that we do things.

Chandler Bolt: Yeah. Well, I think that's the thing about innovation, right, is when the new thing comes along, if it's significantly better than the status quo, well, then the status quo starts to feel dumb. And so, I think with Uber and taxi, that's a great example where it's, okay, well yeah, it makes sense that you would manually pay someone when they finished delivering a service, but then Uber came along and was like, “Hey, you actually don't have to do that. We will automate all of that, and so we will eliminate the weirdness from this experience.” Well, now it seems stupid to do it that way.

Justin Donald: Yeah, that's right.

Chandler Bolt: I think it's very similar for us in Self-Publishing. Traditional publishing, it's like, "Oh yeah, that's just how you do it. You sell in bookstores, you need a publisher, you need all these gatekeepers and middlemen.” And then we say, “Hey, what if traditional publishing and self-publishing just had a baby and it was a better baby? That would be us. Let's work together. Let's create this book. And now it feels stupid to go the other way because you're like, "Why would I give up all this control, the rights, the royalties, soaking things in the process?”

Justin Donald: Everything. And the rights, to me, is the most important thing because I have friends that went the publishing route that want to redo their book or come out with a new version or update their book and their publisher won’t let them, whereas I was able to do it frictionless.

Chandler Bolt: Totally.

Justin Donald: Just, hey, I want to update it. I’ve got a bunch of new deals I’ve done. I got status updates. Like, there’s a whole bunch I’ve learned from these billionaires that I’m hanging out with, like I want to get their playbooks out there, mindset, tax strategy, asset allocation. So, I redid my book, added about 25% to 30% more content to my book, like that. No problem, no friction, no issues. And so, to me, owning the rights is so important, and then just the rights for anything else you would want to do. I mean, if you write a book, my good buddy Kary Oberbrunner has this whole thing of like, when you write a book, there’s actually 17 streams of income that can come from it, and it’s all the different subsidiaries of it. It’s like speaking and coursework and mastermind, masterclass, the list goes on and on, right? And so, yeah, I think if you’re going to do it, you got to own it, yeah.

So, your story is really fascinating because you’re a college dropout who was broke, who started a company. You did over a million in profit in a short period of time. I think it was less than a year, and then by the next year, you’d either doubled or tripled up. I think I had seen something. You got to like $3.3 million in less than 24 months. So, tell us that story.

Chandler Bolt: That’s a crazy story. I mean, growing up, I think I subconsciously knew I always wanted to run a business because I watched my dad and my mom do it. I mean, my dad runs a small-town construction company. My mom, she was a dental hygienist for a bunch of years, then became a realtor. But they met working night shift at a factory, pulled themselves up by their bootstraps, and I noticed, hey, hold up, they’re at my T-ball practice. We’re taking a vacation when my friends’ parents can’t. So, I think subconsciously, I was wired for entrepreneurship and then consciously, I chose it. And the light bulbs just came on as a kid when I started doing stuff and you started making money. And you think, oh, my gosh, I remember the first time I got paid $500. I had like a– it was moving pressure washing and lawn care business, which those three things really. So, it’s just like basically a handyman business, but then I really…

Justin Donald: Like, how can I make money? What needs do I need to fill?

Chandler Bolt: Call me whenever you want, as long as you call me.

Justin Donald: That’s right.

Chandler Bolt: And I will do whatever. And so, I got paid 500 bucks to help these people move out of a house because my mom was a realtor. And I mean, life was never the same again. I mean, I remember just looking at this thinking, first off, this is an iPod, so I can buy an iPod with cash. Second off, this would’ve taken me a month or two in my job doing maintenance on the tennis courts to earn this much money. And so, it just, holy, I mean, that changed everything. And then you fast forward, I mean, I think to really give you the answer to your question, not to give you my whole life history here, but I mean, it just, that unlocked all these things.

And so, I went off to school. I started running businesses, and those businesses started doing decently well in high school and then in college, my first six-figure business running a painting business. Then, I mean, it just unlocked all these things and so dropped out of school, launched a couple of books. The books did decently well. People started asking, “Hey, how are you doing this?” We launched what became SelfPublishing.com, and then it just has kind of scaled significantly over the last decade and some change.

Justin Donald: Yeah, and I think, like you had said or I had read somewhere that in two and a half years, you were up over $5 million. So, you, literally, in two and a half years, went from broke, college dropout to $5 million in net worth.

Chandler Bolt: Yeah, something like that. I mean, I think, like a lot of those numbers were revenue numbers. And so, I think early on, it’s like, I think year one, we did 1.3 if I’m not mistaken. Then year two, it was two-point something. And then year three, it was probably three to five, somewhere in that range. And so, then you go through this whole cycle, right? I’m sure you’re familiar, Keith Cunningham has this quote that I love.

Justin Donald: Think time, I learned think time from him. I implemented that in my life on Fridays. That has been a game changer.

Chandler Bolt: It’s great. I need some more think time, honestly.

Justin Donald: Yeah, no electronics. Turn everything off. Just let your mind wander. Get out in nature. Go on a walk. I started at one hour, I moved it to two hours. It’s like my most productive time of the week. It’s so good. I’ve had so many ideas. I’ve had such clarity. I’ve solved so many problems. It’s pen and paper, and often, I don’t even do that. Like, it’s just so clear that I don’t need to capture it, because, like I just, I got it.

Chandler Bolt: That’s cool. I like that framework. I need to get that integrated. His book, The Road Less Stupid, is really good.

Justin Donald: So good.

Chandler Bolt: I mean, but he has this quote, “Revenue is vanity. Profit is sanity. Cash is king.”

Justin Donald: Yeah.

Chandler Bolt: Revenue is vanity. Profit is sanity. Cash is king. And so, I think that’s what I had to learn early on because the business hits seven figures and then you think, I’m rich. But then you get the P&L, and you’re like…

Justin Donald: You’re like, where’d it all go?

Chandler Bolt: Oh, I’m broke. I got no money. It’s like the seven-figure struggling on. It sounds so funny to people who haven’t lived it, but it’s the seven-figure broke entrepreneur. It’s like, okay, cool, you have a seven-figure business, you’re lucky if you have a six-figure job.

Justin Donald: Yeah.

Chandler Bolt: Lucky.

Justin Donald: Well, that’s the difference right there between a P&L and free cash flow, like an income statement, right?

Chandler Bolt: Totally.

Justin Donald: It’s understanding like what are you reinvesting back into the business? What is your take home? And then are you allocating appropriately for the investments that can work without– I mean, you got to put in some time and energy once to do the research and whatever else. But then you’ve got investments that can now create income for you while you sleep.

Chandler Bolt: You’re even talking cash flow, right, which most people, they’re lucky if they have six figures in profit.

Justin Donald: Right. True.

Chandler Bolt: On a million-dollar business.

Justin Donald: Very true.

Chandler Bolt: And so, I think, that’s what early on, I had to really learn that. So, there was these struggling lean years that, sure, on paper sound awesome. We’re doing millions of dollars a year in revenue. And then you realize you got to get under the hood and say, okay, that’s great. Now, I got to become a real entrepreneur.

Justin Donald: That’s right.

Chandler Bolt: And I got to learn how to run a profitable business. Oh, we’re profitable. Oh, we got no cash. Well, that’s why cash is king, right? So, now, okay, we got to operate our cash flow mechanisms. And so, then I think two, three, four years in, that’s when it really started cranking. And okay, now, we’re really growing and we’re really profitable. And I would credit a lot of that to Keith Cunningham and kind of getting under the hood on a bunch of that stuff. But then it started stacking, and then the net worth starts rising significantly. Then we got time to do some more of the fun investing stuff and the stuff that I know you’re talking about at the time.

Justin Donald: Yeah. Well, let’s get into that for sure. So, I love telling people, like in the beginning of starting a business, you’re just in survival mode. And I remember playing CFO early on. It was like, I’m CEO, I’m COO, I’m CFO. And though I can do it okay, I’m not as good as a dedicated person that is an expert in that space, right? And so, it’s like you bring in these smart people that can really help you. How do you grow revenue? How do you cut expenses? Who’s looking at the financials every week, every day, every month at a minimum, right? And that way, you’re not getting into so much trouble, but early days, it’s like, it’s survival. You’re just trying to get by and you’re like, we don’t have enough people. We got to get someone here. I don’t have time to do this. You’re hiring, you’re investing everything back in the business. And so, but I love now that you’ve got a mature company. I’ve got to imagine profit margin has increased over the years as you become more savvy as an entrepreneur. And I know you’ve started investing. And I’d love to know what are some of the investments that you’ve done that have been really good wins? And what are some of the investments that you’ve done that have been really great lessons, right?

You probably have– I mean, I always tell people you don’t learn when things go great. Like, you actually think you’re better than you really are. You learn when things don’t go great. This is an entrepreneurship as well, right? Because as entrepreneurs, we’re all eternal optimists. We’re going to figure it out, we’re going to make it happen, we’re going to rally the troops. But an investor’s a different mindset. An investor, it’s an entrepreneur, goes into a deal, like, this is a good deal. I’m going to see if there’s any reason I wouldn’t do it, but this thing sounds really good, right? And they’re like emotionally in.

An investor says, this is a bad deal. The only way I’m investing in it is if I prove that it is actually a good deal, right? So, it’s that mindset shift has been a game changer for me and I’ve learned so much in the losses that have made me such a better investor today. So, I’d love to know, like what have you done well with? What have you learned crazy lessons from?

Chandler Bolt: Yeah. Well, you either win or you learn, right? And I’ve got plenty of winners and I’ve got, honestly, probably even more learners aka losers. But I’d say some of the wins were, early on, I mean, I went out and bought SelfPublishing.com. That was a massive win. And so, early on, I thought digital real estate. So, I thought, now this is being totally disruptive with AI and search right now. But there was a while where I said, okay, I could buy physical real estate or I could buy digital real estate. Well, we got really good at SEO and search engine optimization and then blog content and all that stuff. So, I said, well, if you can rank for a key term, like how to write a book or how to publish a book, in our world, that’s the term that we really care about, that’s a really profitable term. Well, if I’ve got a blog on our site that ranks in the top three, I look at that as like a) it’s a real estate property that is in a really good area and it pays me rent every month. And so, that’s how I thought about it is, I said, hey, let’s invest in that because I’m going to get cash flow of that.

So, obviously, we built it up internally with Self-Publishing School. We said, this is working really well. I’m getting paid rent on all these keywords that we own. So, I said, well, let’s go out and buy another one. I went and negotiated the buyout of SelfPublishing.com, and then we built that. That was basically when we got it, it looked like it was in 1990’s Microsoft hunk and got that for less than six figures.

Justin Donald: That’s nice.

Chandler Bolt: It was a really good domain and a– or an email list of close to a hundred thousand people. And so, we used that and then we built that up and that became a $75,000 to $150,000 a month customer acquisition channel. And so, the cost acquire customer at that point is basically nothing, right?

Justin Donald: Well, it sounds like a no-brainer today, but back then, you’re like, wait a minute, I have to spend how much to buy this thing that’s producing nothing. Like, it’s a big risk that you’re hoping.

Chandler Bolt: Well, you got to build the team, right? And so, it’s like, well, I got to build the team and hope that that works. And so, you’ve got some proof of concept, yes, so that would be one of the biggest winners early on. Then I replicated that playbook with TheBookDesigner.com with a couple other small domains that worked. Then I replicated that playbook doing a little roll-up, and so, I thought, okay, I’m not really good at investing outside the business yet, I don’t think, so how do I fuel the main thing? So, I did a little roll-up, bought a couple of companies, few different domains, and that was decent overall, but I think I would consider that a learner, not a winner.

And so, what I didn’t realize because I said, oh, well, we got at the playbook. Let’s just run that back. And what I didn’t realize, there was these freelancing sites and about half or more of the traffic was freelance writers, and the other half was people who would actually want to become authors. And I just didn’t fully calculate that properly. So, it wasn’t as profitable as an acquisition channel as I thought. And then it started competing with our other stuff, both in terms of ranking and Google, but then also in terms of just mind share for the business, trying to do seven things you’re doing well. And so, we’ve sold off since, sold off a bunch of those assets. And that was a learner.

And then I would say there’s some winners that I’ve made in the hard money side of things, like doing some hard money loans and real estate and stuff like that. Some of those are good and then some of those were not so good. So, I think a mistake I would speak to that, I think would be really helpful for your audience, because I’m sure there’s plenty of people thinking about doing this. It’s just back-of-the-napkin hard money loans to people in the industry. And so, that’s like, I’m even going through some of that stuff right now where I made some dumb moves that I shouldn’t have. And so, I’m having, I call it paying tuition to the school of life. I’m paying tuition right now.

Justin Donald: Hard Knocks.

Chandler Bolt: And learning, and so, I’m sifting through some of that. But I think it just goes back to the classic big lesson learned for me. It goes back to the classic Warren Buffett quote, be fearful when people were greedy and greedy when people were fearful. And so, I think we went through this frothy 2021 to 2023, 2024 range period where everything’s ripping. And you feel like an idiot if you’re not investing. There’s deals everywhere and it’s like, man, and meanwhile, inflation is crazy. So, then you’re like, my cash is rotting. There’s lots of it.

Justin Donald: People are making money in any way. It is. People are making money in meme coins. People are making money with a banana as a picture. Everything’s pumping.

Chandler Bolt: Yeah. So, I think I learned some lessons because I made some bets that I shouldn’t have. I’m now having to unwind those and I should have, like investing in a family office, that’s been a great move for me that saved hundreds of thousands of dollars in taxes. They’ve brought me a bunch of great deals. Here, I’m doing some stupid stuff that in hindsight’s stupid. At the time, it looked great. So, it taught me to really tighten up my contracts, tightening up the worst-case scenario, if this, then that. Getting personal guarantees, getting business guarantees. How do you tie that in? It’s all stuff that I know you do extremely well, and I’m sure just like coach people through, but it’s learning. That’s why people need to join your mastermind.

Justin Donald: Here you go. You love teaching this.

Chandler Bolt: You save what Keith Cunningham calls the dumb tax, right? I’m paying a lot of dumb tax right now.

Justin Donald: That’s right. So, by the way, I’ve also learned the super tax many times over, but it’s interesting. So, early on, I thought I could take people at their word and then I realized, oh, you really can’t. You need a contract.

Chandler Bolt: Yes.

Justin Donald: So, then I used the cheapy sites, maybe like LegalZoom or something. I got a contract that had no teeth. So, I’m like, oh, my goodness. And so, I just learned, if you’re going to, well, first and foremost, say no more than you say yes. If you just do that, say no to deals more than you say yes, you’re going to come out ahead, right? Because most deals are bad. You’ve got to find the good ones. So, just kind of have that mindset. And then in the world of hard money lending, if you are not an expert, you are going to get taken by an expert, right? And so…

Chandler Bolt: That’s good.

Justin Donald: Yeah. So, it’s like little things I’ve learned along the way. Number one, always get a personal guarantee, right? I didn’t do that in the beginning, so I got burned there. Number two, always get collateral, right? So, I remember doing that, but I didn’t perfect the collateral, right? So, it didn’t tie back properly. So, it’s like I’m not set up. Yeah, so you’ve got personal guarantee, collateral. Perfect the collateral. Make sure the collateral is worth more than what it is that you’re lending, right? And then there’s all kinds of other things that you can weave into these agreements that can give you a competitive advantage because if I’m going to do hard money lending, I need the pressure to be that you fulfill the agreement we have in place.

Chandler Bolt: Yes.

Justin Donald: Therefore, if you don’t, it needs to be a lot stronger, right?

Chandler Bolt: That’s a big one.

Justin Donald: And so, I like designing these and we like investing with groups that do this, where whether they pay or whether they don’t, you win either way.

Chandler Bolt: Smart.

Justin Donald: And so, if you can win either way, that’s a huge win overall. So, my investing in that space has shifted a lot and I do way less to almost nothing in hard money lending myself these days. And I go with the professionals that have a track record that have been doing it for 15, 20-plus years and we’ve just had great returns because they actually know what the heck they’re doing.

Chandler Bolt: Yeah, how that works, huh? That’s super smart because I would say, even just to break down, I mean, I’m currently in a deal right now, which is okay, I’d learned multiple iterations. I have a better contract. I have a personal guarantee, and I have a business guarantee, and I know this person is worth significantly more than the amount that I lent them, but where I missed is on the teeth. So, now, I’m having to go back and clean that up, which, I’m all ears for advice that you got. I mean, I think it’s going to be a process of like, okay, cool. Now, we got to get on the title. We got to go through legal. We got to ensure the contract says that they got to cover legal costs, but…

Justin Donald: But do they have the money to cover legal costs? Are they going to file for…

Chandler Bolt: I know what you’re saying, yeah.

Justin Donald: Yeah. So, that’s the reason the collateral is just so, so important. And I mean, I feel like I’ve made every mistake in the book here and there’s just so much that you don’t know and there are so many ways that people can kind of skirt the system. And so, yeah, I think it makes sense to hire a great legal counsel, to pay top dollar, to have the best contracts out there, to anticipate every situation that could actually happen. And then as part of the collateral, I’m often negotiating for membership interests, like into those entities, right, so that legally I have that.

There’s other language you can put in these contracts where some states don’t like this, some states do, where there’s a confession of judgment. You can have them sign over that right away, which is them basically saying that they’re guilty or that they’re foregoing their ability to fight it, right? So, there’s a lot of, like, the crafty people that know what they’re doing, they don’t lose. They do not lose or they rarely, rarely lose. And I just learned that I lost too many times and I’m going to just do it the right way, right?

Chandler Bolt: Yes, that’s good.

Justin Donald: Just do it with the professionals. Well, let’s talk on the passive side of things. So, it sounds like you had some lessons learned on the business acquisition, right? And you’ve had some successes on the business acquisition. We talked a little bit about hard money lending. Are there other deals that you have done investing that have gone well and haven’t as maybe an LP or as a partner or anything like that?

Chandler Bolt: Yeah, I think early on, I did a bunch. Well, I lived in San Francisco, so I did a bunch of venture stuff. And so, then you realize, I mean, it’s very similar to the book publishing industry actually. In traditional publishers, it’s like, you’re going to have one out of a hundred if you’re lucky.

Justin Donald: That’s right.

Chandler Bolt: And that’s where you make all your money and the rest are either losers or base hits, right? But you’re not making money on any of those. You’re making money on your unicorn, right? So, I did a bunch of VC stuff. Mediocre. I would not probably touch that asset class much more these days. I got over-indexed on it early on because I was in San Francisco and you’re making money and you got deals all around you, that sort of thing. And then I think, gosh, from there, I did, and this is maybe a cautionary tale and a win, is I got advisory shares in a company and they became a unicorn.

Justin Donald: Oh, that’s awesome.

Chandler Bolt: But I didn’t have my liquidity.

Justin Donald: Okay.

Chandler Bolt: And so, that’s what taught me about the venture stuff is like, okay, I got a minority equity stake in this company, but then they became a unicorn. So, on paper, my equity is worth a ton. They did a massive raise. I wasn’t able to take money off the table. Should have negotiated that in. Big-time tuition to the school of life there. And so, now, I’m still holding that bag of non-liquid stock. Without getting into too many kind of details, I don’t want to out the company because I think they’re good people. It’s a good company. But when the money calls and it’s like, well, if you cash out more than seven people, we got to do a tender offer and is going to slow down this whole thing. They’re like, yeah, we won’t do that.

Justin Donald: That’s right.

Chandler Bolt: And so, then now, of course, I didn’t cash out. Then they got just in the AI space. So, they got disrupted immediately after. So, now, it’s like do the IPO because that’s the only way I get paid unless I sell on the secondary. So, like, that’s an advisory kind of lesson and I look at that more like venture, and then other stuff is hard money on real estate, hard money, minority equity owner, business, a hard money minority equity holder on the storage facility. So, there’s a bunch kind of in that space, and then just, I mean, investments in the business. I don’t really count that, although my stance has shifted due to some of these losses because I’m like, man, I look at investing outside of the business way differently than investing in the business. That’s stupid. Because what’s the best return in the business?

So, right now, I’m investing a lot into a content media team and all that stuff. I will likely lose money on it for the foreseeable future or it will be non-liquid for the foreseeable future. Okay? But the upside is way bigger on year two, three, and four of that than just being like putting it in, like a hard money 10% kind of situation. So, that’s some of the stuff. And then I’m like in private equity stuff, that’s more of an asset class that I like, but there’s kind of a bunch of stuff.

Justin Donald: Yeah, this is awesome. Thanks for being so open on all this. And I love that you’re just willing to share all these things and it gives me some fodder to be able to kind of share, dig through, like jump into, but I think your situation that you outlined is kind of the entrepreneur’s dilemma, which is, I know this industry so well. If I invest my money back into here, I see the path to a return, I see a path to a really good return, and I’m willing to take the risks and the time, and it’s calculated, but it’s still a risk. And so, you get burned on some bad deals not knowing how to invest because you’re spending your time building, right, versus learning how to invest.

And now, all of a sudden, it’s like, well, these are more dangerous over here on the passive side, and my business is where I go. And then most entrepreneurs over-allocate to their business. If anything happens to their business, it wipes them out or close to wipes them out, right? And so, we have just had so much fun teaching entrepreneurs, like, let’s give you the playbook of billionaires, let’s democratize what they do, and let’s show you why they put actually so much of their net worth in alternative investments, in passive vehicles, because once you get that game, it’s the easiest returns you’re going to get.

Once you find the sponsors that have been doing this for 15, 20, like we just invested with the sponsors, been doing it for 30 years with an incredible track record, right? And so, we just formed this new partnership with a group that consults a lot of family offices and gets access to institutional deals. And so, all of our Lifestyle Investor members are fired up because we’re getting institutional level quality deals with preferred terms. Like, our preferred terms are better than what anyone else who is invested in these deals is getting, which is pretty cool.

Chandler Bolt: That’s cool.

Justin Donald: And so, I think that as entrepreneurs learn the foundation, they get an education, learn the lingo, they find that it does make sense to diversify from their business into these other asset classes. And then even speaking to what you were talking about before, I love that you share, like, hey, I now know one out of a hundred companies in the early stage is– that’s like a normal good win, right, which sounds crazy, but the law numbers tell you that, that it’s usually one to two out of a hundred, right? And that’s if you’re really good.

Chandler Bolt: Yeah, yeah.

Justin Donald: So, it’s actually, for most people, worse. Did you know that you have to invest in 412 companies to get a unicorn? That’s usually how many it takes. And so, that’s why billionaires only put about 1% at max. Usually, it’s less than 1% of their net worth in early stage. And then for VC, once you get to later round, so early stage being like angel, like seed, pre-seed. Once you get to venture stage, series A, all the series, B, C, et cetera, it’s usually 4% to 10%, right? And even an aggressive family might be up as like 12%. So, it’s such a small percentage. And then if you look at the bigger chunks, it’s 20% to 30% in real estate. And often, you’re seeing 25% to 40% in private equity, part of that being the VC, right?

Chandler Bolt: Yeah, totally.

Justin Donald: And so, it’s fascinating to help these entrepreneurs in our community have these mental shifts that are so empowering, where it’s like, actually, no, I do want to– it’s not that I don’t want to invest in my business, I just don’t need to invest everything into my business. I need to extract some that can be building my net worth over here. And even more important, in my opinion, building cash flow over here because I think the moment that people have financial freedom, that’s the moment they make the best decisions they’ve ever made for their business and for their family.

Chandler Bolt: I agree. I think that’s super smart.

Justin Donald: Well, this has been a ton of fun. Tell us where we can learn more about you and Self-Publishing.

Chandler Bolt: Yeah. So, I’d say two kind of resources for folks. If you want to grab a free copy of this book, Published, go to PublishedBook.com/audio. You can get the audiobook of that. And then secondly, if you want to check out the company Self-Publishing.com, go to Self-Publishing.com/apply, book a call with our team, we could talk about your book, all that stuff. And then lastly, I’d say, we’re doing a bunch of content stuff. So, we’ve got to find a Self-Publishing.com YouTube channel. We’re about to hit a hundred thousand subscribers there.

Justin Donald: All right.

Chandler Bolt: Putting out a bunch of content. And then I’ve got a Chandler Bolt channel as well, and that’s all things scaling business. So, that’s more just for fun for my buddies that are entrepreneurs and creating the content around all the non-sexy stuff that it takes to actually scale to eight.

Justin Donald: The hard work, you’re saying. The real work.

Chandler Bolt: So, those are a couple of fun channels. If people, if you want the business scaling stuff, go to the Chandler Bolt YouTube channel. If you want book stuff, go to SelfPublishing.com.

Justin Donald: I love it. That’s awesome. I appreciate you being on the show. I love ending every episode with a question to our audience, so I’m going to ask you, it’s the same one every week, but what is one step you can take to move towards financial freedom and really move towards a life that you desire that’s on your terms. Most people live life by default, how do you live a life by design? And what’s one thing you can take from Chandler today to move in that direction? Thanks, and we’ll catch you next week.