In short
Episode 254 is a conversation about “3 paths” to replace a W-2 quickly, plus how to choose and build lifestyle/bootstrapped businesses.
Guest
Chris Sacchinelli, a former CFO who left finance to buy a $96,000 pool route and grew it into an $18M business in about five years. He argues that lifestyle businesses can be “life-changing,” and that replacing W-2 income can happen with small customer counts (example: 10 customers paying $1,000/month). He claims “passive income” is rare—mostly for people born with money or already wealthy. He recommends three business types: newsletters (long-game distribution like SEO), low-capital home services (pressure washing, window washing, carpet cleaning, etc.), and AI consulting (helping SMBs implement AI).
Notable examples
Christmas lighting entrepreneurs (Steve Hunsaker and Ann McGinty) and a former CFO named Clayton from the C4 energy drink company who scaled a $96k pool route. He also shares newsletter strategy: “know thyself” then focus on distribution, and uses a “mind, people, money” framework.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Power of Lifestyle Businesses
0:45 to 3:00
Discussion on the potential of lifestyle businesses and how they can replace W-2 income.
“creating content while also building, buying, and selling businesses.”
Chris's Journey into Podcasting
3:00 to 6:00
Chris shares his background, motivation for starting the podcast, and learning experiences.
“Because I think that that is a very unique concept that you just flagged, like creating a capsule.”
Favorite Episodes and Entrepreneurs
6:00 to 9:00
Chris talks about some of his favorite episodes and entrepreneurs he has interviewed.
“I still think newsletters are just an incredible investment.”
Exploring Business Frameworks
9:00 to 12:00
Discussion on frameworks for finding successful business opportunities, including newsletters and home services.
“That might be like the only differentiating asset that I have.”
Local Newsletters and Monetization
12:00 to 14:00
Strategies for starting local newsletters and monetizing them effectively.
“job all the way to exit five, sell your business, right?”
Finding Your Niche in Entrepreneurship
14:00 to 15:20
Learn how to identify what you are good at and passionate about for entrepreneurial success.
“So I think that if you aren't passionate about something, you're not going to keep doing it.”
The Reality of Passive Income
15:20 to 16:40
Understand the misconceptions surrounding passive income and how it truly works.
“And then once you get started, stay consistent.”
Building a Home Services Business
16:40 to 18:10
Explore how home service businesses can offer low capital entry and high cash flow.
“So we also, like we don't talk about it a ton, but we own blue collar capital and that's all home service, blue collar stuff in the portfolio.”
The Importance of Getting in the Weeds
18:10 to 19:40
Learn why first-time entrepreneurs should immerse themselves in their business for success.
“Pick something that you can understand at least the mechanics of how to grow it and how to operate it in particular.”
Entering the AI Consulting Space
19:40 to 21:00
Discover how to leverage AI consulting as a viable business option for new entrepreneurs.
“I would spend time, energy, and money producing this podcast, interviewing these individuals, and giving you insights into how to build, buy, start, grow your business.”
Show all 30 chapters
Navigating Multiple Business Ventures
21:00 to 22:40
Understand the challenges of managing multiple businesses and the importance of focus.
“Like I like the fact that it gives you a place to look and focus.”
The Pursuit of Freedom in Entrepreneurship
22:40 to 24:20
Examine the true goals of entrepreneurship beyond just financial success.
“I had CEOs who were running those businesses, but I was operationally responsible for them.”
The Concept of Uncapped Upside
24:20 to 26:10
Learn about the potential benefits and risks of entrepreneurship regarding financial and personal freedom.
“where you offer a couple of services and then are really hands-off.”
The Concept of Uncapped Upside
28:00 to 29:00
Explore the freedom and potential of uncapped financial and personal growth.
“So when I say uncapped upside, the inverse is also true.”
Ranking Values: Mind, Money, and People
29:00 to 30:10
Learn how to prioritize mind, people, and money in decision-making.
“I feel like we subscribe to a similar sheet of music.”
The Importance of Focus in Business
30:10 to 31:25
Understand the need for focused decision-making and prioritization in business.
“Could I get people together to actually figure out how to solve healthcare?”
Personal Philosophy: Family and Business Balance
31:25 to 32:45
Discuss the importance of family priorities in business choices.
“And now you have this like almost like pressure is a privilege to a certain extent.”
Creating Freedom Through Structure
32:45 to 33:55
Learn how to create a structure that allows for personal and professional freedom.
“It's because I'm like, my kids are going to be out of the house.”
Launching a Healthcare Venture Studio
33:55 to 36:40
Discover the process and considerations of starting a healthcare venture studio.
“Because literally, you're creating the ability to have the freedom of time to spend with your, invest with your family while also still pursuing what you're passionate about.”
Evaluating New Ventures and Ideas
36:40 to 38:45
Learn how to assess the potential of new business ventures and partnerships.
“So Owen and I might have experience, but maybe we don't have anybody on the team who can actually help spin up a CRM, for example.”
Lessons from Past Ventures and Experiences
38:45 to 40:05
Reflect on lessons learned from previous ventures and accelerators.
“that's like the lens that I'm looking at it through now is like, how do we generate quick wins?”
Focusing on Industry vs. Function
40:05 to 42:01
Examine the debate between focusing on industry or function in business.
“And it was a very visceral experience because we lived it every day and there's a lot of energy.”
Investing in Startups: Insights from Experience
42:01 to 43:28
Learn about the challenges and considerations of investing in new businesses.
“let's invest in people who are starting businesses.”
Bootstrapping and Financial Strategies
43:28 to 44:41
Understand the importance of bootstrapping and strategic financial planning in business.
“Yeah, I kind of really actually super love it.”
The Complexity of Business Structures
44:41 to 46:54
Explore the complexities involved in managing business structures like holdcos and funds.
“Like we're, we're, we're trying to figure this out.”
Accelerators vs. Incubators: Which is Better?
46:54 to 48:28
Debate the merits of accelerator and incubator models in business growth.
“And I got, it's just like, I don't want to figure all that crap out.”
Challenges of Scaling Businesses
48:28 to 50:08
Discuss the difficulties in scaling and managing multiple business ventures.
“But both of them are just like very exciting opportunities.”
Simplifying Business Operations for Success
50:08 to 52:02
Learn strategies for simplifying business operations to enhance productivity.
“Like legitimately, yeah, like all things for sure to think about.”
The Value of Lifestyle and Bootstrap Businesses
52:02 to 53:55
Recognize the importance of lifestyle businesses in achieving a fulfilling life.
“Anybody would want to buy, but you would never want to sell.”
Redefining Success in Entrepreneurship
53:55 to 55:40
Reflect on the true meaning of success beyond financial metrics in entrepreneurship.
“It is like quite like you have the prerequisite of you need experience and everything starts somewhere, but it's almost like having the goal line.”
Transcript
Automatic transcript. May contain errors.0:00I made$1 ,000 on YouTube, which for me was like, what? There's a million ways to make a million bucks and I want to find everyone. Now we look at Facebook and we're like, it's a money printing machine. I put a dollar in, I get$5 out. He was the former CFO, left it to buy this$96 ,000 pool route and grew that to an$18 million business in like five years. They look down on the$200 ,000,$300 ,000,$400 ,000 a year pressure washing business. When in actuality, that guy's living the life that we all thought we wanted when we started out. I genuinely believe like these lifestyle businesses, these bootstrap businesses, they're life-changing businesses.
0:30You could get 10 customers, charge them$1 ,000 a month, and all of a sudden you've replaced your W-2 income. There's only two people who have passive income. Do you know who they are?
0:41You are a content creator who is also practicing what you preach, creating content while also building, buying, and selling businesses. And you have been doing it for a long period of time. Your content, I'm a fan of your content. Thank you. I was telling you pre-show, like I cook steaks to watching it. Sweet. Why did you start? What's it about? So a couple of years ago, I sold the majority of my businesses. I bought, sold, started over a dozen businesses. And I got in this kind of weird spot where I was no longer operating businesses. And if anybody who's listening that's bootstrapped a company, you know that it takes a lot to be successful.
1:14It takes a lot of focus and you can't be chasing a bunch of shiny objects. So when I sold, that was the first time in years that I like picked up my head to look around like, oh, I could do something different than what I've been doing for the last 10 years. And I started getting really curious. I started actually seeing different types of businesses like CAC. What's CAC? I don't know what customer acquisition called. LTV? I don't know what that means. SEO? Like all these things that I just didn't know. And at the same time, I have a friend of mine who's on social media, and I saw the relationships that he was building.
1:44My kids were young. And so it kind of just came to this point where I was thinking, I want to meet interesting people. and learn about their businesses because I don't know what else is out there. And this will be a way for me to meet them. I'm terrible at journaling. So this is a kind of a journal for my kids. They can come back and listen to, you know, 38, 39-year-old dad feed it into an LLM and actually have a conversation with him. And then number three, I want to learn. So meet cool people, journal for my kids, learn cool stuff. And that's really why I started the podcast. And now over 250 episodes later, I've interviewed tons of different entrepreneurs in different industries.
2:18And it's been a blast, man. I'm still having fun. Dig it. Yeah, no, so many of those things resonate very closely. I think that the concept of a capsule in time, that's a unique thought, right? Yeah. And it's something you have to invest in. Yeah, I mean, that's why I got these cool lights behind me and stuff. I've spent a ton of time. I was just telling my wife, I made$1 ,000 on YouTube last month, which for me was like, what? I can't believe I made$1 ,000 on YouTube. And she's like, oh, cool. So your hourly rate is like 30 cents an hour? I was like, okay, fair enough. But yeah, it takes a lot.
2:50It's like a business. It takes time. It takes consistency. It takes execution. You've got to be willing to pivot. It's not easy. When you're creating the content, are you thinking about the audience? Are you thinking about your kiddos? Because I think that that is a very unique concept that you just flagged, like creating a capsule. Yeah. And there is a real reality that this content that we're creating right now could be turned into some sort of something for them to experience. So I think of my kiddos in the sense that I don't want it to be incongruent what they see with who I am. So I'll make stupid jokes.
3:22I'll, you know, just have fun in these conversations. I'm not trying to be super buttoned up and be like, well, did you know that the AltaVita-Kak ratio is actually translated from the Greek? I don't want to be like that. I want my kids to actually see who I am. So that kind of informs the way that I approach things. As far as who I pick to interview, it's really just, oh, that's interesting. What's a newsletter? Oh, that's interesting. What's gutter cleaning? Like, so then I get to go learn about it. I mean, you get to go into the economics of it. I mean, it's Nickonomics. Yeah, yes. So you do also nerd out as well.
3:53And how many episodes have you done so far? I think 250. I think we're at 250 recorded. Such a like crazy milestone. In a year and a half, it's too much. I've actually decided, I'm like, I got to cut back. I can't do three times a week anymore with all the stuff that I have going on. It was a season. It served a purpose. It's been amazing. I've met some really cool people. But yeah, about 250 in a year and a half is a lot of episodes. Yeah, no, it is. Of the 250, what's your favorite? Oh my gosh. That's like asking which one was my favorite kid. Well, top three. Top three. Most recently, I had an entrepreneur named Steve Hunsaker on.
4:30And I honestly don't even remember what we spoke about. I just remember I had a ton of fun. And Steve's this guy who just has like lots of ideas. He's done a lot of home services. I think his first business was a Christmas lighting company. I got a lot of energy from that one. I think that was a really cool episode. But Ann McGinty has been on a couple of times. And she's just somebody who always has a lot of ideas. She also started a Christmas lighting company. And then I had someone on, and I'm blanking on his name, but he was the former CFO of, do you know C4, the energy drink company? No. Okay, so they're big.
5:04They do like hundreds of millions of dollars a year. He was the former CFO of that company. left it to like buy this$96 ,000 pool route and grew that to an$18 million business in like five years. Clayton is his name. That was a really, really cool episode. Just so those are three off the top of my head. Just interesting people that I talked to. Dig it. When you're talking about the businesses, like, I mean, you just listed three. They're definitely SMBs and they're definitely simple businesses. Two of them were the same. Christmas lights. Christmas lights. Doesn't get much simpler than hanging lights, right?
5:37I mean, you get to explore all these things. So I think like in the tagline of your channel, it's literally there's a million ways to make a million bucks and I want to find every one. Yes. What are the best? I'll give you some that I really like, but I'm actually more interested in the framework that kind of I've created than I am specific businesses because I think that the business changes depending on you. Let's talk about the framework. I'll give you three that I love right now. Newsletters. I still think newsletters are just an incredible investment. They're not something that's going to pay off right away, but if you take time to build out a distribution channel, you have a lot of opportunities down the road.
6:13So newsletters, whether that's local, whether that's topic specific, whether that's personal, I just think a newsletter are really cool businesses that I hadn't thought of. Pretty much any home services business that is low capital investment that can scale to get me out of my nine to five job. So we're talking about like pressure washing businesses, window washing businesses, carpet cleaning, roofing, not so much. But anything that I could like$10 ,000 investment and all of a sudden within a couple of months I could replace my W-2 income on the home services side. I really like that. The third one would be AI consulting businesses.
6:49I don't know if you remember this. I'm 40. I'll be 40 in a couple of weeks. But in 2008, people didn't know what social media was. They didn't know how to rank on Google. They didn't know like how to actually go and get business. And so they would just hire anybody off the street. They're like, oh, you know what Instagram is? Be my social media person. I think in the way that that happened in 2008, AI is now that in 2025. These small businesses know they need it. They know that it's valuable, but they don't have the first clue of how to actually implement it. So if you're somebody who knows a business, go learn AI and you can start an AI consulting company helping with implementation.
7:23So those are the three that I think are really cool businesses at the moment. Yeah, no, I dig it 100%. It's like on the AI side, it's, you know, social media, 2000, 1999 to 2000. It's this change of an era going from yellow pages to.com, first time. Somebody who could learn how to build with Dreamweaver could charge 35 grand to make an HTML website. And that's, I mean, it's really like one of those moment in time type of shifts. Now we look at Facebook and we're like, it's a money printing machine. If you understand how to target people, if you understand how to like write the copy and run the ads, I put a dollar in, I get$5 out.
8:02But back then there was no such thing as Facebook ads. Google pay-per-click was a thing, but even SEO was like barely understood. It was the Wild West. So if you just knew a little bit, it added so much more to the businesses than people actually realized back then. So yeah, I think it's very similar to 2008. What about newsletters? So newsletter is something that we dabbled in. And I did a buy and build in public on this channel a couple of years ago. We acquired a whole bunch of newsletters. We rolled them up into Simple Profits, which we run now weekly, like 300 something issues, 50 ,000 subscribers.
8:35And that's what seeded a lot of this channel. You had somebody on the pod recently, and it was like local newsletters. It was like a way to grow a list local. Like, what are some of the teach train equipped hints? Like, what's the cheat codes for somebody who wants to get into the newsletter game? Let me actually start backwards, even higher level than that. I think when you're looking at starting these types of businesses, the first thing that I want to look at is, what do I know? What am I good at? What do I have experience in? It might be that I have time. That might be like the only differentiating asset that I have.
9:10I might just be young and I don't need a ton of money until I can spend time on things. It might be that I have a specific skill set. It might be that I have a specific knowledge base. But you want to look and say, what do I differentiate in? And then the second thing you want to do is focus on distribution. Those are the first two steps. Know thyself and then work backwards in terms of distribution. Is there someone that I know? Could I piggyback off of somebody? How could I actually sell this? Then comes kind of everything else. So the reason that I love newsletters is because newsletters are like SEO, search engine optimization.
9:41If you have a website and you just add articles over time, over time, over time, you rank better and better and better, right? Google looks at you. Oh, this is a trustworthy site. They have this history. Certain keywords are obviously being filtered all the time when people are searching for things. So the more articles you have, the more keywords that those can show up, the better your ranking. So, but SEO is not a short term thing. It's not like, oh, I wake up one morning and all of a sudden my website is search engine optimized. It takes time. But if you're willing to be consistent, it's pretty simple.
10:10That's how I look at newsletters. Newsletters, you're not going to wake up overnight and be like, I've got a whole million dollar business. But if you find within a market one of basically these three criteria, either you're a local newsletter and you're geographic specific. So you're like everything to everybody. Number two, you're a local newsletter, but you are demographic specific. So I'm like, I'm a local newsletter for dads in their 30s. Or you're a local newsletter with an interest specific. So, okay, I'm a local newsletter for concerts. If you pick one of those and you just start putting out week after week after week, you will gain subscribers over time.
10:53You can play the long game there. And all of a sudden, within a couple of years, or if you're really hungry, a couple of months, you can have 10 ,000 subscribers. And then what happens is you have distribution. So companies will pay you because they say, Chris has eyeballs that are looking at his newsletter every single week. Oh, and they're a local newsletter, local to Connecticut. Great. I want to advertise my local business to this newsletter because it's got the demographic that I want to advertise to. And all of a sudden, you can start making money from that. That's like the first order of making money.
11:24The second order of making money is, hey, I started this newsletter and it was for dads in their 30s. Now I have 10 ,000 subscribers and these are dads in their 30s who on average make$100 ,000 a year that are health conscious. What business could I launch off of this? Could I launch a supplement business? Could I launch a content business? Could I launch a gym membership? Now I'm playing in the game of I can launch a business because I have the distribution as opposed to I'm just getting money from advertisers who are willing to pay me for the eyeballs within my distribution. So our audience, we call them investmentors.
11:56We focus on everybody from exit one, which is exit your day job, make your business your job all the way to exit five, sell your business, right? And everything in between. Everything starts somewhere. so we just gave a place to start and the first was like know thyself find a voice which may be difficult right that's i don't know it's harder find a voice or find distribution but from a find a voice perspective you gave two different approaches two very different approaches one was who do you identify as dadpreneur and the other was where do you identify who do you identify with and that was that local geography right and you're focusing on different things.
12:38Now, I know that there's different strategies where you could start local, you could pair up with businesses, you could cross promote, you could build your list that way. And it's like very systematic. It's very process driven. And there's a built-in market. There's a built-in demand. It's a way to monetize very quick, which is what you just kind of covered. And then the dadpreneur is like something that's hopefully passion filled. Which do you think would be the better place for somebody exit one to start and why? When you say exit one, they've already exited? Exit one, exit your day job. You're trying to exit out your day job.
13:10Oh, oh, oh. And make something your job, make something profitable, make something going. Do you think that you should start writing something that you resonate with, like Dadpreneur, and you're just writing it weekly because that's your passion, that's your identity? Or do you think you should get specific and say, hey, I'm going to build this specific local newsletter? Okay, I'm going to get a little touchy-feely with you, but I think it's 100 % the truth. How old are you? 36. Okay, I think you'll agree with me. You have enough life experience. Have you heard of this Japanese saying, ikagi, I-K-A-G-A-I?
13:44Yeah, well. So it's these concentric circles. Did you say yes? Yeah, for the audience, though. Okay, it's these concentric circles of what do I know? Like, you know, what's my skill set? What am I passionate about? And what will the world pay for? Now, anyways, there's like a fourth one that people use. I like to use just the three. So I think that if you aren't passionate about something, you're not going to keep doing it. Like entrepreneurship is hard, whether it's a side hustle or whether it's your main business. And there will come a day where you're like, why am I doing this? Like I could just go get my job back.
14:18Why am I trying to actually launch this newsletter? And if you aren't at least passionate about it, it makes it much easier to give up. So I think what you need to do is take a look at yourself and say, what am I good at? What am I passionate about? And what will people pay for? And it's not just going to be one thing. You can take a look at the market and do a market assessment and say, what newsletters are out there? What is saturated? What is not saturated? What do I know? And you start building sort of this profile of newsletters. And then all of a sudden, you're going to have like a list of five where you can say, you know what?
14:48I'm an electrical engineer and I live in New Haven, Connecticut. And I really, really love doing projects at my house. I'm going to start Dad Renovator newsletter because I know that there aren't that many. I know that it's a high ticket item. I know that I can speak passionately about it and knowledgeably about it. And I can do it for long enough where I can do the fulfillment until I can, whatever, bring somebody in or hire somebody on. So that's really more the approach that I would look at is kind of those three things. What do I know? What would add value? And what am I passionate about? Yeah, it doesn't have to be perfect.
15:19It's like everything starts somewhere, just get started is the key. And then once you get started, stay consistent. Because consistency is the thing that separates most, right? Most folks can't stay consistent over a long period of time. it is probably easier if you find the money you do something simple and find the money fast but it's true but that's just not life yeah i have this i have this joke where i'm like everyone wants passive income and i'm like dude there's only two people who have passive income do you know who they are they are people who are born with money or people who have already made a lot of money because then they have money and they can buy real estate and they can get passive income from that real estate basis yeah no i don't think that there really is any such thing as truly passive income unless you're like truly just like to the point where you don't care because no matter what there's concern concern costs stuff if i have 50 million dollars and i put 10 million of that 50 50 million with somebody to manage it and be like just get me like a five percent return a year to me that's passive i don't care that's passive income i'm at the point where that's but you don't get there unless you have 50 million dollars do you know what i mean everything Everything starts somewhere in a very real place.
16:30Everything starts somewhere. So the newsletter place is a place to start for sure. Home services, high leverage, low capital, high scale. It's a very real place to start for sure. Love those businesses. So we also, like we don't talk about it a ton, but we own blue collar capital and that's all home service, blue collar stuff in the portfolio. And it's a very real space and it's becoming more popular than it's been in the past. How do you do that? So let's talk about, what do you think? So low capital, high scale. We gave a couple of examples, pressure washing. Do you see these businesses being things that you could build and then and get yourself out of?
17:09Or do you think you're do you think you're creating an asset getting into this or are you just replacing a job? I'll go through my framework. If you are a first if you're a first time entrepreneur, kind of what I've seen is you just want something to get you in the game. and the reason I like these home services businesses is because they're low capital and they have the ability to generate high cash flow. And by high cash flow, I don't mean a million dollars a year, but I mean enough cash flow to replace your W-2. And then you're in the game. Then you're getting experience, how to run a business.
17:38You're understanding how to hire people and how to manage a route and how to actually sell to individuals or upsell or how to deal with problems that you didn't actually foresee before you started the business. So for me, it's like you're just getting in the game and that's not going to be your forever business. And that's okay. There aren't many people who are still with their first business. Like Mark Zuckerberg being with Facebook until now is like not a common thing. Yeah, it's kind of like you don't know what you don't know. You don't know what you don't know and you don't know how to get better.
18:06So everything needs to start. That's why when I'm talking to entrepreneurs in particular, I say, know thyself first, first and foremost. Good place to start is a newsletter. Find a voice. Yes, find a voice. Pick something that you can understand at least the mechanics of how to grow it and how to operate it in particular. I think a lot of people look at this and like, oh, I want to hire someone to do it. Oh, I want to have passive income. And it's like, people talk about it like it's a bad thing. Being in the weeds in your first business is the differentiator. Like your willingness to outwork other people, your willingness to just figure it out becomes the differentiator.
18:43And if you rob yourself of gaining that knowledge and that experience, you will never understand how to scale because you can't scale something that you don't know. And that's why I tell a lot of people, it's like pick something that's hard and sweaty and get in the weeds for a year or two, really understand it. And then you can pick your head up and like, okay, I didn't like this. I like that. I think I'm going to try this new thing over here. Yeah, but the depth and breadth of experience that you're going to pick up and the good time decisions you're going to make because of it. Totally. You can't replace it.
19:10You can't replace it. Third, AI consulting biz. Yeah, I just love these businesses. What about a duo? If you notice, all of these businesses, I'm picking for like first-time entrepreneurs who want to get into the game. And this is another business. All of these are services businesses. So all of these are a pain to scale. You've had services businesses. It's hard to manage people. They depend on people to scale. Hey, I don't know if you remember this, but when we started this podcast, we entered into a social contract. I would spend time, energy, and money producing this podcast, interviewing these individuals, and giving you insights into how to build, buy, start, grow your business.
19:49And you would like, subscribe, and leave me a five-star review. Now, out of that, we both get to talk to really cool people and hear really cool insights. We both get a ton of value. But I just want to help you keep your word. So would you do me a favor? Will you go leave a five-star review for me on Apple or Spotify? It would really help. and if you want, even share this with a friend. So for the most part, many of these are going to hit a ceiling and the same would be for AI consulting services. But it gets you in the game. And right now there are so many business owners who don't even know what to do with AI.
20:20They're like, well, should I be trying to rank on Google's AI search? Should I be using AI? Well, I have some marketing needs. Should I use AI to write my copy? Could I replace employees? How do I audit? Like they just don't know. So if you can step into a business and say, hey, I used to run an HVAC company. Let me show you how to use AI in your business. It's going to save you time. It's going to save you money and it's going to drive you revenue. They're going to pay for that all day long. And you don't need 50 customers. You could get 10 customers, charge them$1 ,000 a month and all of a sudden you've replaced your W-2 income.
20:54And now you're learning on somebody else's dime. And like I said, it's just like getting into the game. It just gets you in the game. Yeah, I like the focus about it. Like I like the fact that it gives you a place to look and focus. and in focusing it gives you the place to plan and then just do and once you do do a little bit more do a little bit better for sure but yeah like it gives you you know honestly because i do think that shiny objects is a very real thing for a lot of folks but like giving a place to focus and then not having the pressure of it having to be huge and just building a simple business that actually generates revenue, hopefully kicks off profit, put some profit in your pocket.
21:34It's like a great place to start. That's a great place to live. And then life is a very long thing and it's a journey. And then as you go down this journey, you start to pick up the experience. You go exit two, exit three, exit four, exit five. You're learning how to operate businesses and then exit businesses, which you have experience with, right? So if we wind it back into not, you know, exit one early audience, but folks listening that have seven, eight figure businesses right now, and they're trying to really pick up some game. What do we do? Take us back to those moments in time. So if we did a quick inventory, seven, you had seven eight-figure businesses that you exited from, healthcare, e-com, crypto.
22:15They weren't eight-figure. They were combined. They were doing$30 million a year in revenue, but they weren't seven individual eight-figure businesses, if that makes sense. Gotcha, yeah, yeah, yeah. Okay, so healthy seven-figure businesses. Healthy seven-figure businesses and were you running them all at the same time or these were individual pursuits and focuses and there were moments in time and you were navigating them and then you had to make decisions of what to do. So no, I wasn't running them all at the same time. I had CEOs who were running those businesses, but I was operationally responsible for them.
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22:48And we were talking about this before the call. I was excited to dive into it. Kind of going back to the like, know thyself. What motivates you? What are you looking for? A lot of times you get into entrepreneurship and you think, well, I want to have a hundred million dollar business or a billion dollar business, or I want to own 10 companies. I saw this clip of Chris Krohn talking and he's like, I'm really deep into private equity. My goal is to own 10 ,000 companies. And I think any entrepreneur who has experience would understand nobody wants 10 ,000 businesses. It's so much headache. It's so much complexity.
23:19And so when you're starting out, you don't necessarily know all of these things, but you kind of know that you want freedom. you want the ability to not have a capped upside you want to control your schedule and your life you don't know any other path than entrepreneurship and every entrepreneur that we've seen on the news is like mark zuckerberg is a hundred billion dollars you know elon musk has 500 billion dollars and so you think that's what you're supposed to shoot for what i've learned over time however is that many people lose sight of that and they think they think they look down on the two, three,$400 ,000 a year pressure washing business.
23:55When in actuality, that guy's living the life that we all thought we wanted when we started out. Controls his schedule, has good money, is well known in the community. You know what I mean? And so we chase a lot of these bigger things. So to your question about running these businesses, I realized kind of over time that operating dozens of businesses is really hard. Yeah. It's at scale. It's really, really hard unless they are all the same type of business or you have like a centralized office where you offer a couple of services and then are really hands-off. If you're trying to like roll up different businesses and different industries, like we have a tree trimming business, we had a crypto mining business, we had an RV park, we had a digital agency, home health, hospice, medical practice management.
24:45None of those are similar. And so there's a lot of operational complexity to executing well on any of those individual businesses and your context switching all the time, it makes it really difficult. So what I would say to somebody who's trying to scale, I don't think trying to get to a hundred million or a billion dollar companies, bad thing. If you're trying to scale, pick an industry and stay in the industry or pick a function, centralize that function and just be totally hands off. So you're either Jeff Bezos and you have one company effectively, or you're Warren Buffett and you have 50 different companies that you own big stakes in, but you're totally hands-off.
25:24In a nutshell, I would say that's kind of my lesson in hold co-building. Oh, like without a doubt, a thousand percent agree with all of that. And I think that right now it's becoming more of a popular theme. So I've been building Simple Holding since 2012. And when I started, nobody knew what a hold co - It was not like, I literally be like, what are you doing? Like, what is that? A business that owns other businesses? What do you do? How's that a thing? And now it's starting to become like more and more popular. And as things start to become more popular, obviously more people get involved with it.
25:59And when more people get involved with it, not all the right people are getting involved with it, just a lot of large numbers. And that's like a great formula for a lot of mistakes to happen. And when a lot of mistakes happen, there's loss. and I one of the things of this show I would hopefully like to help folks do is avoid risk and avoid loss right mitigate the risk decrease the risk increase your upside so one thing for folks listening is like don't make that and don't make that the pursuit right like that's not the goal you got to figure out how to get yourself there is the goal and you just gave a couple of really cool things for us to get into first was like the ability to not have capped upside That's like a cool quote.
26:42That's a quotable. The ability to not have a cap upside is like super cool, which means you have an objective of putting yourself there, right? So you have a goal and then you have a thing you need to focus on. And then in approach from specifically the whole co-perspective, we said industry focus or function focus. And you're quite literally thinking right now through this, right? So early in the show, you said like literally something you were quite literally thinking through. Let's work through it together. Like, I love this. I obsess over this. This is what I live. When you're thinking about it, how do you differentiate?
27:17Like, what is your core objective? So on the whole co side, it's the ability to not have capped upside. What does that even mean to you? Because you said not just money. You said also time. Like, you sprinkled in a couple of things after, which I thought was like, oh, that's brilliant. That's awesome. My brother-in-law started a company eight years ago. He literally bootstrapped it to a$500 million company today. He's still operating that company. Great company. And he said to me early on before they even got the ball rolling, he was like, you know, I just got tired of relying on other people's generosity.
27:49I think many times when you are in a job, you're relying on your boss to say you do a good job and maybe give you a bonus or maybe give you a raise. And the metrics aren't really clear or objective. So when I say uncapped upside, the inverse is also true. You have downside. Like you could go bankrupt and lose everything, but it all of a sudden it's dependent on you now. And so now I'm not just going to get that 10 % raise a year or maybe a$20 ,000 bonus. Whatever I do could be as big as I want it to be. If I execute well, there's something freeing about that, that I really like. The other sides of the upside are, I want to spend my time with whoever I want, working on the projects that I want.
28:34To me, that is what brings joy and fulfillment in life. So if I am creating my own opportunities, my upside is not capped because now I've got the potential of financial upside. I've got the potential of intellectual fulfillment and I've got the potential of emotional fulfillment and stability. So, you know, money, mind and people. So that's why I say like there's an uncapped upside when you're looking at growing these businesses. I feel like we subscribe to a similar sheet of music. We're reading off a similar sheet of music to a certain extent. I'm a big believer that money is a short-term motivator.
29:12I think that money is a short-term motivator for people, whether you're in a job or whether you're an owner. It's there when you don't have it, but then as soon as you do, it becomes very much so less valuable and other things in life become more valuable. and we're living in a world of real constraints and scarcity. And we are at the end of the day, allocators, whether we accept that we are or not, all of us as humans are, we have a certain amount of time to allocate to anyone, which thing or heart or anything really care. When you're thinking about this, like what is the frame? So mind, money, mind, and people, how do you rank them?
29:48Like what is your rank and retrieve to make decisions around? What's your framework? Because you mentioned a framework earlier a couple of times, and I also want to squeeze out the framework itself. So I'm trying to... My ranking is mind, people, money. And mind and people are probably interchangeable. Money is definitely a third. So mind being the intellectual pursuit, mind being the ability to pursue full potential, mind being... Curiosity. Curiosity. Oh, that's interesting. Can we solve this problem? Is it a big enough problem? Could I get people together to actually figure out how to solve healthcare?
30:23Is it going to stimulate me every single day to keep coming back to it? Because if it doesn't, I'm going to be distracted by something else. Does that make sense? Yeah, it does. And it also ties in because it's like mind is almost like the ability to be selfish, selfish to be selfless, to be selfishest. Mind, I have to identify the thing that's big enough to get people involved. Second, people. So now I need to be able to selflessly get people involved. self-adjust collectively as a whole, we need to pursue this thing and make some money. We need to make some money. Yeah. Yeah. No, it makes a ton of sense when you're thinking about the whole code and you're thinking about what you're doing.
31:01So you have a ton of collective experience. You have experience as an operator, the life experience of needing to do things, right? So we all, we need to do stuff at first and then eventually you achieve and you kind of have more freedom and it's like, what do I want to do? And that's typically like when a lot of shiny objects start to come in and you start doing a lot of stuff because you're like, oh, I couldn't do this stuff before. And now let me do everything. And then you realize, oh, that's a lot. It's not really what I want. It's not optimizing for my life. What do I do now? And now you have this like almost like pressure is a privilege to a certain extent.
31:36You have like you're put in the position of privilege to a certain extent to make the right type of decisions, good, timely decisions. And you also have kiddos and you have all these other things that you need to make employees, team members, all this stuff. What's your frame? So not necessarily where you've been, but where you want to go. Like when you're thinking about your businesses and you're thinking about what you're building, what is your frame that you're deciding with that? So I'll give you the philosophical and then I'll give you the practical. The philosophical is my biggest rule is I don't want to be away from my kids.
32:05Yesterday was our first day of the basketball season and I'm coaching my two boys teams and we, and they're back to back and we got them arranged and I got to coach my eight-year-old and my five-year-old. It was freaking amazing. So good. We had a son that passed away 10 years ago. And that was just a, I mean, you've been through some stuff. You shared some things with me before we started. When you realize what life is really supposed to be about, then you're able to set very clear expectations for yourself. And I'm not saying I always adhere to them, but that's one of them. I want to be around for my kids.
32:40I'm turning 40 and I'm going to be honest. I'm a little bit of a head case about it because I'm like, not because I'm sitting here like, I thought I'd be a billionaire. I thought I'd have five jets. It's because I'm like, my kids are going to be out of the house. And like, then what am I going to do? I freaking love these little a-holes. They're just going to leave someday. So that's my number one. That's my number one when I'm looking at opportunities right now is, do I have to go anywhere? Do I have to be gone? Can I be there for basketball practice? Can I be there for soccer? or can I be there for music or sports activities, et cetera?
33:15And then I would say it's the three that I've already said. Can I work on the thing that I want to with who I want to when I want to? And if it doesn't meet those criteria, then we don't, I don't really pursue them. But once I'm into something, we can talk about like specifically how I'm evaluating things right now. So first and foremost, that was, yes, absolutely. And absolutely on a lot of different levels. And I appreciate that. when you're in that mindset, two-part question would be the structure of approaching that because that seems ideal. And then you need to create the ideal, right? Because literally, you're creating the ability to have the freedom of time to spend with your, invest with your family while also still pursuing what you're passionate about.
34:05And then the byproduct becomes these pursuits that you do, which becomes another level of accountability and you're responsible for. So then you have to have the structure to be able to manage it and maintain it and focus on it. And I guess that also directly ties into what you just said, which is framing of decision. So how do you decide what to do? Well, the first thing I'll say is I know that I'm very lucky. And for probably 99 % of people who are even listening to this, I've gotten to do something that they haven't, which is I had time. You know, I had exits and I had money and I didn't have to jump into something else.
34:39I wasted a lot of time, but like it also just had the freedom to like explore and figure out what was the next swing going to be. And I wasn't ultra concerned about organization and like trying to optimize. Now though, I'm at the place where with my brother-in-law, we just launched a healthcare venture studio, which I'm freaking stoked about. Okay, let's talk about it. So this is the thesis behind the venture studio. He has this healthcare company. They're big. 5 ,000 employees, 8 ,000 patients, 70 facilities, $500 million in top line revenue. And for the last year, he knew that I was doing podcasting and looking around.
35:15We'd been talking about, let's start a venture studio here in Boise, and we could invest in companies. And it was all these things outside of healthcare. And eventually we had a conversation where I was like, oh, and why did we do anything other than healthcare? We know healthcare. We've been better than 99 % of people in healthcare. why wouldn't we just double down and stay in healthcare? And it was like, duh. So we decided let's launch a healthcare-focused venture studio where we can leverage the assets within his company to build other products. And the lens that we look at it is like this.
35:45Do we understand and can we add value to the product? That means probably 90 % of them are going to be healthcare items. And they might even be focused to things that we have experience in, like home health, hospice, home care, skilled nursing, assisted living, etc. But there's going to be 10 to 20 % that are not healthcare focused, but we can still add value to. One example would be, maybe there's an HR software that somebody has created that maybe we want to start up or we want to invest in, or a CRM that we want to build for our own purposes. That's not necessarily healthcare specific, but it is something that we can leverage the assets of Cascadia, who we've partnered with, in order to suss out.
36:26Right. So that's, that's the first question is like, do we have a core competency to actually add value to this thing? The sort of second question is, okay, if we do have a core competency, do we have the bandwidth or the expertise within the team to help facilitate that? So Owen and I might have experience, but maybe we don't have anybody on the team who can actually help spin up a CRM, for example. The next lens layer that we look at is, all right, since this is going to be more of a venture bet, we know that eight out of 10 venture bets are going to fail. We're going to throw a million dollars a year at this.
37:00And so if we're throwing a million dollars a year at this, we at least need a 20 % IRR. We know it's going to be better over time, but at least in like the initial two years, we need like a 20 % IRR. So any project that we take on has to return a minimum expectation of between$100 ,000 and$200 ,000 in value. So maybe we'll have a hit rate of five out of 10. But at least if we just regress to the mean and have a hit rate of two out of 10, we are at least returning that$200 ,000 so that we can have that return on invested capital because we're putting a million dollars a year. And then the third piece is, is it an incubated idea or is it an accelerated idea?
37:42If it's incubated, that means we are going to create it internally. It might be an AI software. It might be a product. whatever it is. There's somebody internally who has an idea. Cool. We incubate that and then we give it an opportunity, but it also might be an accelerated idea. So maybe somebody has gotten to an MVP, but they just don't have a customer to test it with or resources or distribution, whatever. And so is there an opportunity for us to bring in somebody into the accelerator and then grow them? So one of the companies that we're talking to right now is a staffing company. I'll try to be as specific as I can, but remain high level.
38:16A staffing company that has no healthcare experience. So they already have the operational expertise in staffing, but they want to get into healthcare. Well, that's a perfect recipe for our accelerator. Cool. Come in. We'll give you access. We'll take an equity stake in this new venture. You can understand healthcare. We'll give you access to our distribution channel. We'll advocate for you. And now you have the operational expertise. You've already done this before. You can go and run with it. We can drive business your way. It's a win-win for everybody. So they come in for three months, learn the healthcare space and spin out.
38:44And so that's how the accelerator portion of it works. that's like the lens that I'm looking at it through now is like, how do we generate quick wins? Dang it. I have so many questions. Okay. I don't know if you want to go through them or if you're going to want to have the answers on them or not, but I got so many questions. So talk about live, learned experience. So flashback 2012, bootstrapped eight figures, sold, restructured. First thing I thought I had to do was start vesting in companies because I felt like I wasn't a real startup guy. And I had a big chip on my shoulder and I was like, oh, this is what you do now.
39:23So I got this huge space in Norwalk, Connecticut and we just started opening up doors to companies to come in and we called it an accelerator, an incubator accelerator. And I was like semi writing checks to them. We had a semi-structured program that they would go through. And long story short, it was not a success. It was a great way for me to lose my money. Spoiler alert, it was not a success. And what I did pull out of that is a lot of structured process, a lot of things that we ended up productizing and turned into playbooks. And then I ultimately implemented in other aspects of the portfolio in other ways.
40:03So there was value extraction and it was a very real experience. And it was a very visceral experience because we lived it every day and there's a lot of energy. I didn't learn my lesson because in 2016, I repeated the same thing, partnering with IBM and doing an AI accelerator program in Bridgeport, Connecticut, converting a space. So I have this live-learned experience of this approach. So I have these questions and thoughts in mind as well. But the key thing is you define something in terms of a focus. so you are now specifically focusing solely on healthcare whereas previously we just listed a whole spectrum of different businesses that you're involved with it was like tree trimming all the way to x xyz in this moment in time you have this focus so industry so earlier we said that there was two perspectives to take in terms of the whole code am i having an industry focus or i'm having a functional focus, industry focus or functional focus, Amazon, Berkshire, and you decided industry.
41:10So you were focused on health, which is like so cool in the first place. I wish I could get into like being in the healthcare industry because talk about a macro trend. Bro, I love, I talk about that all the time. Warren Buffett has a quote where he's like, Like, what's my favorite business? Or what's my favorite boat? A boat with a tailwind. So, like, I just love macro trends like that. Dude, and, like, so cool. Like, so many things. And, I mean, you have the experience, which I don't think I actually knew. Like, on the in-home living, assisted living stuff. Like, talk about a great, you know, that's a super interesting industry to just nerd out on.
41:48So many different angles to take. Let me hit a couple things that you said. One, I also had a similar experience. Chris and I, my best friend, we launched this company called CoFounders. And the whole idea behind it was like, okay, we have some experience, we have some money, let's invest in people who are starting businesses. And so the tree trimming business came out of that and digital agency came out of that. Yeah, it created the problems that you're talking about. And so what I realized in that was like, first of all, I don't have enough money to do this the way that I'd want to do it. Because, and you probably noticed it too, you would have had to hire like a program director.
42:23You'd have to hire someone who's like, an operator who's in the weeds with each one of these. You got to do a lot of mentorship. You got to get them up and running. Like if you're doing an incubator or an accelerator, it requires an infrastructure that is not cheap. So you might think like, oh, I got a couple million dollars. A couple million dollars doesn't cut it. A couple million dollars a year, but not a couple million dollars to like actually start this whole thing. And so I realized really quickly like, oh shoot, man, that's not the way that I want to go. And then by necessity, I had to focus on industry because I don't know your full background.
42:53Chris's background is marketing. That guy, Facebook ads, organic, Google, whatever. So he can invest in basically any industry that worries about CAC and LTV, right? Because he understands how you go out and get customers. And so that's not industry specific, but that's like role specific. Makes sense for the tree trimming stuff. Yeah, quite literally. Get a lead, sell a lead in a sense, yeah. That's all it is. It's a lead generating company and we're actually pivoting that business. But so that's why I'm saying like, you know, if you're an amazing marketer, you could start a whole co-company that's just providing that expertise to founders.
43:27But for me, I didn't have that specific expertise. So I went the healthcare route. I stayed in the industry. Yeah, I kind of really actually super love it. But you're coming in with a big partner, it sounds like. I am, yeah. I think you mentioned it, Cascadia. Cascadia Healthcare. Don't know enough. Not an SME in the space at all, but it sounds awesome. I mean. Because that's like an anchor. That's like a really strong play because now you can make intros. Network is what works at the end of the day. And we can facilitate. We can source a bunch of ideas. We can test a bunch of ideas. Like, there's a lot of advantages to it.
44:01You talked about 20 % IRR, though. Are you pulling in outside capital? Because, yeah, like, that talk about lessons learned. Like, it is, like, a very expensive proposition to execute. No, I mean, that's another lesson learned. No, we don't want to. I'm talking on the bootstrapping podcast, my friend. I'm not raising any money. Like, no. But no fund economics or anything? No. No, it's just us. And I don't even know that we will spend a million dollars a year. That's what we had like originally earmarked where we're like, okay, we feel good about this. But every decision is run through kind of a committee where we have a conversation like, well, do we need this investment?
44:33Like, does it make sense? So like we're willing to spend up to that, but that doesn't necessarily mean, okay, we've got, we have it. We got to deploy it because we're bootstrapping. Like we're, we're, we're trying to figure this out. We haven't taken money off the table, but what we wanted to do is because this is kind of a new venture for all of us. my brother-in-law and then his two partners are our partners in it as well because it's a new venture we wanted to like learn it first yeah shocking i know and then once we have like a track record and we've learned it then we can go raise money at you know advantageous terms and rates etc but starting out it's just like let's just build a muscle first and then if we really need money to throw gas on the fire then we can go and raise money because that's what money's for Like don't note side, that's something that I made a mistake with.
45:19So I took the same perspective. I was like, oh, I don't have the track record to do this. Like I need to do it myself. I need to prove myself. I need to. So I funded and I was like, I'll do it with my own capital, fund it. And then I'll use that to then go raise a fund and then use the economics of that fund to then carry costs and use the management fees to cover op X and then use the capital to leverage up, do more deals better, et cetera, et cetera. and I never was able to bridge it to the second. And if I was to start it again, I would do it from the beginning. Dude, what you just said is like, I just don't think people understand holdcoats or funds.
45:55Once you create a holdco or a fund, you've now introduced a whole other operational complexity and dynamic. You've got to manage the fund. You've got to manage investors. If you're raising a fund, there are real SEC regulations that you need to comply with. And the way that you report and the way that you do your financials, there's a bar that you have to meet. It's, you know, otherwise you go to jail like Tai Lopez. Yeah. Talk about a story, right? Do you want that? Like that, that's the other question is like, now you're, you're answering to a bunch of different people. And the same is true on the hold co side.
46:25Like, okay, you have a whole co now. How do we run payroll? Who does AP? Do we have a shared banking account? Who's funding things up? Yeah. What's the IT infrastructure? Like it's just specific to the, to the accelerator model, to the incubator accelerator model, which I guess, I guess my difference in perspective is you're thinking about this as the whole co and then within this this is your whole code in a sense plat vehicle and then within that you have an accelerator and an incubator structure within it and i'm thinking about it just as like one functional entity of like the thing in which it's happening and like a better way to support that yeah without over over complexity of it because yeah structuring you could always do like entity structuring to be able to you know silo different different things and make it make sense i guess the structuring is one thing but i just mean now you've got like well i gotta have the quarterly compliance call and I got to send out the fund update.
47:16And I got, it's just like, I don't want to figure all that crap out. Yeah, for sure. And no, I get it. I get it. And things definitely, you know, everything, you know, is a process. So when you're talking about this is, are, these are going to be deals that you're either incubating, which means that you're setting them up or you're accelerating, which means that they're already coming in. And then all of it is flowing up. Are you looking to do like majority ownership? So are you doing like traditional HOKO, I want 80 % of ownership into these things? Or are you doing it more like venture deals?
47:52So the accelerator will be more similar to venture deals. The incubator will be more similar to HOLDCO. But the truth is, I don't know. If you could only pick one, which would you pick? Like if you could only do one type, if you could only do incubator or you could only do accelerator, which one would you pick? I love the accelerator because somebody already has a product. that's so hard to even get to a place where you have a functioning product. And if they come and I'm like, oh, man, we know this person, this person, this one. We're connected in this industry and this industry. I think we could really not only help them on the user experience, but we could grow this thing from a distribution standpoint.
48:27That's where I get excited on the accelerator side. So in a vacuum, probably the incubator. But both of them are just like very exciting opportunities. So like something I haven't really seen happened, because like the accelerator model has been around for a very, very long time at this point. And there's different degrees of them, for sure. There's different spectrums that we've seen across the board. I haven't really seen anybody that does like, almost like a PE buyout program where you're coming in with the intention to sell and the whole co is coming in with the intention to buy. And so now you're actually buying established businesses within the healthcare space.
49:05So I'm not opposed to it. Here's the problem with it, and it might be the fundamental problem that I've had with just holdcos in general, is if you want a proper holdco, you've got to have a person to run it. ETA. Yeah, and those are hard to find, man. It's hard to find really good, talented, consistent, dependable operators. and then to give them the equity that they need in order to stay. Like if they're that good, where they're growing that business in the way that you want it to be grown, they're not staying for like 5 % equity. They're mobile. They can go and start their own business. They can go raise money and have 90 % equity.
49:45So it's hard to do it with just one. And then all of a sudden you're like, well, I want to have 10. Like, all right, well, I got to win the lottery, not only once, but like 10 different times. So I'm not opposed to the private equity model where it's an accelerator and you buy them out. The fundamental problem with that is it then exposes me to, now I got to go replace them. Who's the person? And that's just a hard game to play. No, interesting. Like legitimately, yeah, like all things for sure to think about. I think the concept of scaling this type of business model is really so difficult. And I think like what we navigated to very uniquely on this call is so special because it comes from a super organic place and you kind of have to live it to even be able to talk about it to a certain extent, because that is such a real thing.
50:30It's like you're struggling, struggling, struggling. You're working, you're grinding, you make it. Now you make it. Now you have this freedom. You almost put yourself into as many things. You start saying yes, because you want more. And then you create a more problem in a sense. And then you're like, oh, now I got to really simplify. And it's like, oh, what do I do? And like, we're not all worn, you know, like at the end of the day, like not all warren buffett like and that's what i've done on our own you know and then like life is a real thing dude and i think that conversation about like the kiddos and priorities and all that stuff is like such a real thing but meanwhile you're holding these assets which are really just liabilities disguised because you're responsible for them yes and it's like what do i do what i do with my hands i gotta figure this shit out you know which is why i think conversations like this and like this type of stuff is super valuable i love the idea of hold codes it's just when you actually get into it and you experience it for me it's just for me like it totally could be for other people and it is for other people obviously i'm like i just don't want that like overhead in my mind of like oh that we got the liability with this company and this company and this company that are all different yeah i got a context switch every single time time now if you like that stuff and you're good at that stuff and whatever go for it but for me it's just like that's that's a mental tax that i i just don't want to have and so it's hard what we've been trying to do like what i've been trying to drive through through mental model is same thing same effort of simplicity so like i've you know gone through a very similar thing over the the past five years of a reason and outside reason to simplify and primarily driven by my kiddos so like super cool in terms of the overlap where I landed was the concept of just building an ownable business like I feel like the place to live and the challenge that I've been trying to like master for the past half a decade now of like obsession like nerd out obsession in a closet in a room somewhere it's like how do you build a truly ownable business like an ownable business being a business that anybody would want to buy but yet you would never want to sell That's an interesting framework.
52:48Anybody would want to buy, but you would never want to sell. Yeah. So like a business that's so valuable, everybody would want to buy it. So profitable, you would never want to sell it. And then so simple, you could run it. That's a very good and interesting way to articulate it. I used to do it as well. People crap on these quote unquote small businesses. Oh, they do a million dollars a year in top line revenue and the owner makes 300 grand. It's like, yeah, but he works an hour a week. he's finally gotten to the place where he works an hour a week in that business yeah dude controls his life and it's so like what are we here for like because i want to be at a cocktail party telling people i don't care about things that they don't really care about either like i made a million dollars this year aren't i cool and like they're gonna they'll forget about you in 30 seconds like nobody cares yeah what actually matters yeah right yeah dude i think that's why yeah i genuinely believe like these lifestyle businesses these bootstrap businesses they're life-changing businesses.
53:43I think like, honestly, the easiest way to change your life is to get into like a bootstrapped or even like a blue collar, simple profitable business. Genuinely. I don't think that anybody could just do it. I think like what we talked about earlier in the pod is essential. It is like quite like you have the prerequisite of you need experience and everything starts somewhere, but it's almost like having the goal line. It's not the goal line shouldn't be a billion dollars and raising all this venture money and doing all these things. It should be like, I'm starting this local newsletter because I know that down the line, I'm going to have a power washing company.
54:16And I know that after that, you know what I'm saying? Yes. You know? Dude, I invested in this guy a couple of years ago, a couple hundred thousand dollars. And it was a lot of money. He lost it all. It was a bad bet. But, you know, you miss some things sometimes. And his attitude with it was very flippant. And it was like, well, you know, we tried and tell investments go. And I think the thing that I realized in that moment was like, oh, if you've never made a certain amount of money, you just have no appreciation. You don't. And when I hear people say like, I want to make a billion dollars. Oh, I want to be a billionaire.
54:55I'm like, do you know how much a billion dollars is? Do you know how much a billion dollars is? you haven't even made a hundred grand and you're talking about a billion dollars, the sacrifice, the time, the energy, the luck that it takes to get a billion dollars. Like you just don't even have an appreciation. And I think that unfortunately people don't appreciate it because they've never experienced it. And people have made it not cool to be like, oh, this lifestyle business is doing amazing things. And I'm with you. Like that's what life is about. Control your life, control your destiny, do something fun that you love, give back to the community, spend time with your family.
55:31Who cares if it's a million dollar business or a hundred million dollar business? Like I now architected the life that you always wanted. That's why we do entrepreneurship. All right. Hopefully you liked that episode. And if you've made it this far, you're either really committed or you're stuck doing yard work and you can't actually skip on your phone. So while I have you, the show is growing, but I have a favor to ask of you. Will you please help me grow the show? I want to reach more people. There's a couple of things that you can do. Like and subscribe is the simplest thing. obviously you want to get notifications for when the next episode is coming out but if you go the next step will you leave me a review five star on spotify or apple what that does is it tells the algorithm that oh hey this is a high value podcast because more people are leaving reviews for it and it then pushes it out to more people so that's why when people are like will you like and subscribe and put the five star rating it's not just to make themselves feel better it's actually to get more exposure for the show so if you do that for me i would greatly appreciate it and I'll see you next time.
From the publisher
MY NEWSLETTER - https://nikolas-newsletter-241a64.beehiiv.com/subscribe
Join me, Nik (https://x.com/CoFoundersNik), as I sit down with Chris Sacchinelli (https://x.com/@investopreneur_). Chris is an entrepreneur who has been practicing what he preaches for years, creating content while building, buying, and selling over a dozen businesses.
We dive deep into the best paths for first-time entrepreneurs looking to replace their W-2 income. He shares his top three business ideas right now - Newsletters, low-capital Home Services (like pressure washing), and AI consulting, explaining why these simple, bootstrap ventures are truly life-changing businesses.
Questions This Episode Answers:
• What are the three best businesses for first-time entrepreneurs right now?
• What is the true reality of passive income?
• How can focusing on consistency with a newsletter lead to guaranteed business distribution?
• What is the framework you should use to decide what business to start (Ikagi)?
• How do you structure a multi-million dollar Hold Co to avoid unnecessary operational complexity?
Enjoy the conversation!
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Love it or hate it, I'd love your feedback.
Please fill out this brief survey with your opinion or email me at nik@cofounders.com with your thoughts.
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This week we covered:
00:00 The Journey of Entrepreneurship
03:02 The Power of Content Creation
05:58 Exploring Business Frameworks
08:51 The Newsletter Revolution
11:44 Finding Your Voice in Business
15:05 The Reality of Passive Income
17:58 Home Services as a Starting Point
20:50 Scaling Businesses Effectively
23:41 The Pursuit of Uncapped Upside
28:30 The Pursuit of Fulfillment
32:16 Balancing Family and Business
35:07 Launching a Healthcare Venture Studio
38:58 Lessons from Past Experiences
45:13 Navigating the Challenges of Business Models
52:17 Building an Ownable Business
