When it comes to business, the goal isn’t just a big exit—it’s about building something so empowering that staying in or stepping away both feel like exciting options. In this episode, Jaryd Krause is joined by Raleigh Williams, a former Mergers & Acquisitions lawyer turned successful entrepreneur.
Raleigh left his law career after just nine months to start an escape room business, which he scaled and sold for eight figures. Now a father of three and husband to a breast cancer survivor, Raleigh now helps entrepreneurs “take chips off the table” and reconnect with the creativity and joy that originally drove them into business.
The conversation dives deep into Raleigh’s journey—from walking away from law, to building a multi-million-dollar company, to writing a powerful book that helps founders navigate the emotional rollercoaster of exits and acquisitions.
For entrepreneurs wondering whether to sell, grow, or rediscover their passion for their business, this episode is packed with game-changing insights. Learn how to find fulfillment in business, make empowered decisions, and avoid the identity crisis that can follow a big exit.
Get ready for a raw, insightful, and inspiring conversation about purpose, growth, and enjoying the journey of entrepreneurship, no matter what stage you’re in.
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Episode Highlights
03:00 Finding purpose in your work and life
10:00 Combining enjoyment and passion into your business
17:00 Can you truly make a hobby your work?
25:30 The importance of being authentic in both business and personal life.
33:00 How suffering and passion intersect in meaningful work.
41:00 Raleigh’s book and finding true fulfillment.
45:00 Where to find Raleigh and his book?
Courses & Training
Courses & Training
Key Takeaways
➥ Purpose isn’t found—it’s created by doing work that energizes you in the present, not some future ideal.
➥ Passion doesn’t mean ease. True passion often involves suffering you’re willing to bear because the work feels important.
➥ Hobbies don’t have to become work. It’s okay to keep joy separate from your income stream.
➥ Living an undivided life—being the same person in every setting—leads to deeper fulfillment and less emotional burnout.
➥ A true calling feels like something only you can do, even when it’s hard. That’s what gives it meaning.
About The Guest
Raleigh Williams, a former mergers and acquisitions lawyer, left his career in law to start an escape room business, which he scaled and sold for eight figures. A father of three and husband to a breast cancer survivor, Raleigh now helps entrepreneurs take chips off the table and reconnect to their creative abilities.
Connect with Raleigh Williams
Transcription:
Hi, I'm Jarrett Krauss. I'm the host of the Buying Online Business podcast, and today I'm speaking with Rayleigh William, who was a former Mergers and Acquisitions lawyer., He left that career in law to start an escape room, which he scaled and solved for eight figures.
Now he's a father of three, a husband to a breast cancer survivor, and Rayleigh now helps people with such an amazing thing, which is entrepreneurs taking chips off the table and reconnecting to their creative abilities, and helping them find a bit more purpose and fulfillment in their lives.
And in this podcast episode, we talk about Rayleigh's journey of like how he was only in law for about nine months and why he left and then how that evolved into creating this eight figure company, which is the escape room and his exit and then the book that he built and wrote and why he wrote that book. And we talk about specifically entrepreneurs that are wanting to exit their business or have an offer or a deal and whether they should be selling or shouldn't be selling and how does he get them to a place where they're empowered enough to either sell the business for a lot more or hold onto the business and continue to grow it by acquisitions or by just sitting back and let either team do the work.
So he talks more about, like, how do people find more joy in their work and their business, and make a grand exit if it's the right thing. And then what to do next in terms of like their life path after exit, which is super valuable and important because a lot of people become depressed if they're making a big exit and they don't know what to do because they've got money and they're like, what do do with my life now?
And then you've got the opposite side of like, should you just build a business up, and do you want to stay in the business? Like you don't need to make an exit now if you love the business a lot more than you previously did, because you don't feel so bogged down in operations and work. And we talk about how you can do that in your own business. Such a valuable podcast episode talking about purpose, fun, enjoyment, fulfillment, and how we enjoy business and decide to sell or not.
Enjoy the episode.
Riley, welcome to the pod. Thanks so much for your time.
Yeah, man. Appreciate it. Happy to be here.
Yeah, absolutely. You've done so much in M&A. You've come out of M&A, and then you kind of sort of cycled back into helping people sort of with M&A or after M&A, exiting, and stuff. And there's so much to dig into here, but you were a M&A lawyer. How long did you do that for?
I was an M&A lawyer for nine months. So I was a flameout. I was a pretty quick flame out there. Was at, I did it at two different firms. One was one of the top three M&A firms in the world, a law firm in New York City, a place called Skadden Arps. And then I practiced at another firm in Dallas, Texas, called Vincent and Elkins, doing big public transactions as an M&A lawyer, which is potentially the most boring work that exists on earth. So I didn't last very long.
What sort of businesses were you guys acquiring or selling, and why was it so boring? Like you, just like in the wee,lthere for a bit or…
Yeah, I mean, I worked on deals and life sciences, and in New York City, there was a lot of life sciences, biotech work. In Dallas, there were more real estate developers and oil and gas type stuff. I went into M&A law because I thought that it would be good training for me to become an entrepreneur.
I thought that I was going to learn a bunch of stuff that I'd ultimately use as an entrepreneur. And what I found was that the size deals that you're working on they're just so big. They're $20 billion, $50 billion, even billion-dollar, a couple of hundred million dollar deals. The stuff that you're learning about isn't super applicable to running a business, operating a business, doing a startup, or doing your own thing.
And so after I got into it, thinking I could have a couple of years where I would be learning something that would be germane to what I ultimately wanted to do with my life. And very quickly, I realized that I was working on closing checklists, kind of a Microsoft Word monkey.
And so, 30 days into that job as a 30 days into job, after I graduated law school and passed the bar exam, I had a panic attack on my way into work. I was at the gym and I thought that I was having a heart attack. I was having a panic attack, and that was kind of my first signal of like this.
You don't have 10 years that you're going to be able to spend here. Like this, this has to change quicker than you anticipate. And so that was kind of my signal to, like, get to start figuring out what I want to do with my life in a pretty short order. And I think the start of that was going into it, this expectation of like, I think I was scared to go for what I wanted to do, which was running my own business. And so I wanted to go, I wanted to do that in a very safe way.
Almost in a shadow career type way. And then once I got into it, all of my best-laid plans to do that for the rest of my life just fell apart because I was miserable pretty quickly.
Yeah. Mean, what an amazing thing though, to get not 10 years in, but nine months in or so and have that. I mean, it's not great that you're getting so bad that it's physically affecting you, but at least you got out as fast as you could, as soon as you realize those effects versus like some people can do that for a decade and just think that's the norm, you know, for a good year.
From one of them, since I don't drink, or I think a lot of people, they really can't do it, but they find a way to numb themselves to get through it. Drinking or drugs or Adderall, I think they find ways to kind of exceed their natural limitations for as long as they possibly can. And then that becomes its problem.
Like I just wrote a book on kind of like finding your purpose, how to find your thing. And in the book, I write about a guy who was top of his class at a very prestigious law school. And then after 10 years of kind of climbing the ladder, he finally became a partner at this firm, Sidley Austin, which was a very prestigious firm. And within two months of becoming a partner, he ultimately committed suicide in the parking lot of his law firm because he had fixated so much on kind of getting to this mountaintop moment and kind of self-medicated his way there.
You know, he was an alcoholic. Had gone in and out of rehab for alcoholism. And when he finally got to this kind of arrival moment, he realized that he had set his sights on the wrong thing and decided to end his life. So I think for most people, I think that's an extreme case. Most people don't get to that stage, but I think a lot of times, when you're unhappy in this path that you've committed a lot to, whether it's school or tuition money or how much debt you have, you feel like you're committed and you can't reverse that decision. So you try to stick it out for as long as you possibly can, even if everything within you is telling you that you're in the wrong.
Yeah, absolutely. And it can be scary with the society that you have around you, maybe telling you, this is what normal life is, a regular job. And you're like, hang on. It's really hard when you're surrounded by that environment to go, I don't believe it needs to be like this. I believe I can do more and be more, and enjoy more. Which we all can, right? We've got infinite opportunity and infinite potential, every single one of us. And it's so good, the work that you're doing.
Right. This is a portion of what I'm doing with, well, it is, you know, I want to help people replace their income so they can spend more time doing what they love with the people they love. Right. Yeah. Because the more that you do what you love, the better your inflow and life are. And you go from like chasing to attracting. This is my opinion, what I've worked out myself, as well as going from plumber to hating plumbing life, this sort of route.
Yeah, I'm stoked that you didn't stay there for a decade and just suck it up like a lot of people would then go, no, there's better options. So congrats. I'm thrilled for you. And then you moved into business anyway. Like I wanted to mention, like you wanted to do the safe route of like have your job and then see, like kind of like start or business on the side. This is what I tell people to do.
And I think it is the safest route. If it's not physically ailing you, to continue having your work, it's nice to have an income stream and buy a business on the side, or look to find a business on the side, because that way you can slowly leapfrog and not put too much pressure and stress on yourself. Like the stress of having no income, trying to start something, it can cause you to make decisions that aren't the best because you're stressed. Tell me about that. So you just obviously cut it, clean cut, and then went straight into like starting something.
I tried a couple of things on the side. After the panic attack, I thought the panic attack at first was kind of the signal that I needed to make more money to feel freer. And so I tried a kind of side hustle. I mean, this was in 2014, 2015. So buying a business on the side wasn't spoken about. That wasn't a well-laid path like it is now with entrepreneurship through acquisition. And so I tried kind of the side hustle route. I got my real estate license. I thought maybe I'd be a realtor on the side.
I tried to buy tax liens and do a kind of real estate stuff on the side. I tried to do kind of like a faceless Instagram account and try to like, I was trying all of these things that were just money-making opportunities. And what I found was that I was always interested in it for a moment. And then whenever I got my first kind of difficulty, I would quit because I would go into him thinking, this is an easier way to make money than practicing law.
And then, when I found that there was a difficulty in buying tax liens, I was like, I'm only doing this because it's supposed to be easier. This is actually just hard as a thing that I'm doing. And so I had all of these kinds of micro failures where I was losing a couple grand and really just losing the time of and getting more frustrated that I felt like I had had this signal that I needed to leave, but there wasn't this clear path that was presenting itself on what I needed to leave to do of all of the people that I've talked to that have left, and even in my course, I don't know that a clear, you know, I the heavens to open and for the path to be laid out in front of you with a beaming light that tells you the next step forward.
And that never happened for me. I did seven months after that panic attack. My brother sent me an article that was talking about a kind of, I mean, I still remember the title. It was the unbelievably lucrative business of escape rooms. There was this new trend that had been happening in Europe for five years, and Japan, and these escape rooms, where you get locked in a room and you pay to figure out how to get out. And the article is talking about how this emerging trend that was kind of coming to the US is finally here. And so I had never heard of that. I looked up an escape room close to me in Dallas, where I was living, and I went and played one that night with a buddy of mine.
And there was just something about it that it felt I liked, that it was fit, that I could see the product, all of everything else on the internet space of YouTube and Instagram, and do all of this. You're dealing with this in the corporeal world that isn't; none of it physically exists to you. And so I liked the physical aspect of being able to see what this product was. And also it was very. Unintimidating. I was surprised that a product that was so stupid.
Putting a bunch of janky furniture in a room and having people figure out how to get out with padlocks. I was like, it's insane to me that this dumb of an idea could potentially be making this amount of money. And so it felt possible for me for the first time of like, can do, I don't know if I can do a faceless Instagram and be this artist guy, but I know that I can buy some janky furniture and put it in a room and figure out some puzzles.
It was the first, it was kind of, that was the first time where the path, again, didn't present as this clear beam of light onto this path, but it presented as, is something that's within my competency. I can do this. And I tried for a couple of months to do it, to try to find a space to lease while I was practicing law. And it became obvious to me that I was going to need to quit, that I wasn't going to be able to pursue both of them simultaneously, because I was going to have to start it from scratch. If you're buying something now, that's a different path.
If I could have found a way to navigate both of those, I obviously would have. And practicing law, you're making a lot of money nowadays. You're probably making 200 to $210,000 as a first-year associate. So within the law specifically, there's this expectation that you should not be having any outside economic activity outside of your job. And so the law is particularly difficult to kind of find a side path to do. But anyway, that was kind of, that was just not to build your wealth outside of your career.
Yeah, that law and there are a couple of careers like consulting and all those jobs where they're paying you a lot, a high salary, they expect, and any outside, I mean, there's a special process.
I the focusing on that.
They require you to disclose any outside business activity that you have outside of your job at some of these big salary places. Because you're also working on very sensitive and very confidential matters. And so they want to make sure that you don't have a conflict of interest with the work that you're doing. And so it's this very, I think that's atypical. I don't think that's most people's job life, but that was mine. So I kind of had picked this career.
Kind of required me to leave it to kind of find my path.
Wow. Wow. Yeah. Had a story where I was coming up to buy businesses. I'd bought a couple, and I was going to, I was starting to teach people, and I was going to get a job with a brokerage firm, and the brokerage firm was like, you can't buy any businesses, obviously not from our platform, but from anywhere online. And I was like, okay, well, I want to continue investing.
So that's a no from me. Yeah. Well, I'm good friends with those guys still. They've come on the pod, and I've been on their podcast multiple times. They've built their business up. I've built mine up, and it's a great story that you can go your separate ways, like you have as well. That law firm has gone a separate way, and you've gone a separate way, and you've both made it work.
So you mentioned that acquisition, know acquiring, is a lot more popular now. It's still got a bit of a way to go, but I think you're incorrect me for wrong. Did you mention that if you were to start again, like if you were to leave the law firm again and you had some money, would you choose to acquire versus start? And if so, why?
I always kind of have my finger on the pulse of what's happening on the market to the extent that you can find something that kind of matches what you would like to do anyway. And it's already built. Every business is an onion of risk. And when you're starting, the full onion is there, and every step, every stage of business is you peeling off layers and layers of risk of the business.
And so to the extent that you can have an entry point that is less risky because they've solved more and more pieces. I think that's always worth exploring. Think the one hesitation that I always have with people who are on the acquisition side is that there's the risk that exists within the business, and then how you acquire it is super important. And the amount of debt that you're bringing to the business, and whether that debt is personally guaranteed.
I'm at a stage now where I would be, I've made enough money, where I try to I wouldn't put that money back onto the table in the form of a personal guarantee. But if I were leaving my law firm job, I would quit that job with 30 grand to my name. And so to sign a personal guarantee for a couple of million bucks where I stand to lose 30 grand max, I say let it ride, you know what I'm saying? But the wealthier you get, the less risk appetite, you're more concerned with the return of your money than return on your money. And you just want to make sure that you get into a little bit more of a defensive posture.
With family, you know, I have kids and.
Absolutely, and so you should.
So I would say the risks inherent of particularly if you're Yeah, I think I'm always even today I'm not even actively really in the market But you can learn so much about new industries new markets new businesses new opportunities just by looking at businesses that are on the market and to the extent that it makes sense economically to acquire one as opposed to starting one from scratch I think that's always a better entry point because you're just I mean you're speeding up the process and you're paying for something that has already solved a lot of problems and crossed a lot of bridges that you're going to have to cross yourself if you're starting it from scratch.
Yeah, right. You've got product-market fit. People have proven that they're paying for something that they value. That's the biggest heart and part of starting a business. And then the second biggest part is the scalability of that. Right. And you can do your jellies on both of those things and see how it works out. I agree with you in terms of risk.
As you start to grow, there's no need to become more aggressive; is not necessary when you're comfortable. Like what's the point, but when you're not comfortable, like for example, early stages of me being a plumber, I'm like, maybe you with a panic attack, you're like, I'll do anything.
Like, I would do anything to get myself in a better position.
Yeah, mean, like my startup and my startup. I think there's this kind of online world that has kind of glamorized the entrepreneurship path, and my, you know, I quit my job in Texas, and I moved into my in-laws' basement with my wife and my daughter.
And then I became an actor in my escape room because I couldn't afford it, I had to put stupid zombie makeup on my face, and like chase customers around to lose $250 for the day. That was 18 months of that, and it was difficult; it's something that I'm glad that I did. And I am glad that I don't have to do it again for the, unless I sign a bad loan somewhere, you know.
Yeah, but this is the ugly part of what you said, entrepreneurship is glorified, and entrepreneurs are put on a pedestal in the media these days. You do hear the glory stories, but you don't hear the stories of, like, yeah, I was looking at driving Uber one stage, possibly to just keep some more money coming in when things were not going good, or doing another job on the side.
That's pretty normal, you normalize the challenges through entrepreneurship. Want to get to know how you help people and what you do? Do you help people exit their businesses and then move into finding their path? Is it after they've made an exit, or do you help them slowly start to like, like you mentioned, you help people take chips off the table? What does that, what does that look like? And who are these? Like what sort of clients are these people?
They tend to be entrepreneurs who have people that I help on the entrepreneurial side are entrepreneurs who are making at least a million dollars of cash flow per year. So they tend to be businesses that are on the bigger side of things. And they realize that they've been doing this business for long enough. Most people get into entrepreneurship because they think that it's about freedom and that the business that they start or acquire is going to be the vehicle that gives them that freedom.
And I think a lot of times, I wake up five, six, seven years down the road, and you realize that the business owns you more than you own the business, and you aren't nearly as free as you think that you are. But getting out of a business is much more difficult. In my plumber job, on my law firm job, I was always two weeks, I was always 14 days, away from quitting. You could just walk out the door.
And when you have a business with loans and employees and capital calls and operating agreements and partners, extricating yourself from that labyrinth is a more difficult process than you anticipate it being. And so what happens for the entrepreneur is they feel like the business is starting to run them more than they're running the business, but they've ensconced themselves at the center of the business, and they don't know how to get out.
And so they try not to allow themselves to realize that they're getting pulled into this new thing that is either calling their attention, know, shiny object syndrome is a part of it, but it tends to be a major life event that has happened. After I sold my business, six months after I sold, my wife got stage three breast cancer.
And so if the timing had been different, I see it in an entrepreneur that is about to go through a divorce, sickness, illness, a parent or a loved one that's kind of in their periphery dies. And they kind of wake up to this life is shorter than I imagined it to be. And even though from the outside, it looks like entrepreneurship is the greatest thing since sliced bread.
They want to be free. They want to be free from the burden that they can't give off to someone else, like you can in a job. And they want to make sure that they get the economics associated with that. They want to take chips off the table and whether that's selling a part of the business or selling all the business.
And it's a very scary thing for an entrepreneur because they don't have there's no one else that they can talk to. If you talk to a conventional broker, they'll say it's always the best time to sell. So there's not a big group of people that someone could kind of bounce ideas off of, in terms of whether it's now the right time to sell, multiple options, is it worth it today?
And so we try to help people think through that. And if they decide that now is the time to either sell all or a part of their business, then we help make the asset look as appealing as possible and make sure that they get a deal that kind of fits their expectations.
Yeah, cool. Love that. And does it ever get to the point like, cause you're right. Like this is what my biggest warning to people when they're acquiring a business is like, can like at some stage, depending on where you are in buying the business, if you're buying a business under the seven figure range or typically under the half a mil range, you're likely going to be the operator.
Yeah. Yeah. Working in it and it's dangerous because when you start working in it, you can get stuck working in it, and feel like you need to do this job. There's nobody better than me at this job. But the reality is there's like, I'm very replaceable, and this can be people who are better than me at things that I do. Unfortunately, it's not great for the ego. It's great for like, if I can put that aside, it's great for my future self to know that somebody else can do that and free up space, which gives me space for better decisions and ideas, and creativity.
This is my biggest warning to people: you can buy a business and not need to be the operator as well. A LAN entrepreneur doesn't necessarily need to be an operator. If you think of people like Richard Branson and others like large entrepreneurs, like they're not operating all of their businesses.
They've got people to do that. And you can start to do that on a smaller, half, under half a million dollar business. You can have contractors that report to you. Maybe you're the chief of operations, but you're not doing the work other than, like maybe some admin, and then you could hire someone who could be the CEO for you. And that's, do you ever do that for people as well?
Like, it's like you go, well, let's, mean, it's the same process of selling the business too, right? If there's key person dependency, you want to remove yourself first to get a better exit to be more, to make that business more appealing. So do you help with that sort of thing as well? is it?
So when somebody starts working with DealMaven, we give them kind of a broad range of what, if they wanted to sell the business today, what the market would probably pay. And then we give them a list of here are the big impediments to your valuation right now. Here are the things that are dragging, and owner dependency is almost always an aspect of it.
And whether there's owner dependency in the sales process and the fulfillment process, just kind of depending on how big the business is. So there's almost always a process of how we do, what are you doing in the business right now, and how do we get someone to fill that spot before we ever go to market?
Because it's going to come out in diligence, it's going to come out in the process, and you're going to get dinged for it. And so let's fix it before we go out to market. So that's, you know, that would be, I would say that's one of our bigger kind of differentiators between a typical brokerage that says, let's take you to market right now. And because it's owner-dependent, you're going to get a 2X. We say, because you're owner-dependent, you're going to get a 2X.
Let's spend the four months to get you into Forex because those four months to get you out of the business, and you're going to make another couple million bucks, like, are you going to find a better return? Do you have any other place to put your cash that's going to make you a couple of million bucks in a couple of months?
So, like, let's just do the work with you and help make the org chart for the buyer. You know, when I'm talking to a seller, I tend to say, I'm going to help you bury the bodies that are kind of lying out in the ground, and we're going to make sure that whenever it comes out in diligence.
It's not going to be a, I call it burying the bodies, but it's just strengthening the business, is what it is. It's just, I'm trying to make the business better for the potential buyer. Occasionally, not always, but occasionally a seller will decide that now that they've extricated themselves from the business that they don't want to sell, which is, it's almost like, I'm sure you did plumbing jobs where people are like, I got to get this house ready to go to the market.
And they finally renovated the kitchen and put a new bathroom in, and put the new vanity in the master bedroom and then they're like, shit, I don't mind this house that much anymore. This is now a great house, and I don't want to sell anymore. And that's kind of what we do on the business side, is kind of clean some of the stuff up. And if they decide that they want to keep it for another couple of years, we assume that they'll come back to us and use us to help them sell whenever the time comes.
Awesome. I love the work that you're doing. It's so valuable. It's not fear-based. You're helping people go from a possibly fear-based decision to an empowered decision with multiple options versus a fear-based decision. It's like this or that black or white exit or no exit for whatever it's worth right now. Like, let's just get my head above water as fast as possible without thinking about like what's a strategy to get my head above water.
Right. What sort of things can we do along the way? What's that pathway look like? So when people come to you, what's their goal? Like what's their typical, like what's the avatar, is it their goal to be like, I want to exit my business or I want more freedom in my business or is it I want to like, because I help people with like taking chips off the table in terms of like finding their, personal purpose too. What's most of their, most of your audience's actual goal?
They tend not to know, they tend to say, like, the most, one of the companies that we've been working with for two years, they had an unsolicited offer from a private equity fund to buy their pool business for nine million bucks. They had no sense of whether that was a good deal or not a good deal. They just didn't know, they didn't think that their business was worth anything. And so to get a nine-million-dollar offer felt very good. And they followed me on social media, and so they said, Will you look at this offer?
I looked at the offer, and then I looked at their books. A lot of times, owners think that they make what they're reporting on their tax returns. And so these guys thought that they're making two million bucks a year. And so a $9 million off on a $2 million business is not that bad. But when you go through the M&A accounting and you do the ad packs, and you kind of get to the EBITDA number instead of the net profit that you're reporting in taxes.
They're making closer to four and a half million dollars. So it was a two X deal, not a four and a half X deal. And I said, I think this deal is dog shit. You should not take this deal. And we worked with them for a year before we took it to market. And then we took it to market and got them an $18 million offer.
So doubled the offer that they had. But with that $18 million offer, since they had clarity around how to grow the business to maximize enterprise value, they've decided that now they want to be on the acquisition side. So we're helping them acquire other pool companies because now they see a clear path to get to a 30 to $40 million enterprise value as opposed to the nine that they almost took. That was 14, 15, I guess, yeah, a little bit, almost a year and a half ago with their first offer that they had. So it tends to be people, the entrepreneur…
And I can speak to this because I was in this position in my own company, which I ultimately sold. They tend to go through, I almost think of it as a wavelength where there's an ebb and a flow, where some days the entrepreneur wakes up and says, I wouldn't sell this business for a hundred million dollars. And then the next day and their key employee quits and they say, if I got 50 grand and a suitcase on my front door, somebody else could have the damn thing.
Cause I just don't want it anymore. And so we tried to kind of shorten the band and be a sounding board to kind of steady the ship a little bit in turn, and give them a plan on how to get to the number that they're excited about. So they tend to say, I don't, you know, I'll exit for the right number. That's what almost every entrepreneur says. I'll exit at the right number. But it tends to be that their expectation is 50 to 100 % more than what the market will bear. And so we go through and we help them see, okay, well, if that is your number, you're not there today.
There's a gap there, but like we'll help you kind of navigate that gap. So that way, you can get to that number if that's what you'd like to do. If there's a path forward, not every business, we can't help every business in that way, but the businesses that tend to be on the bigger side, a million dollars of EBITDA plus they've solved enough problems in the business and they have enough of the team in place and they're just, they have the resources. They're just not.
Getting deployed into the right areas. And so we help them kind of refocus and kind of package the business in a tighter way, depending on if we feel like we're going to sell to a search funder, that's different than a private equity fund, or a strategic investor. So we kind of get a sense of, you want to sell for $50 million, you're not targeting a search funder, you're targeting a different set of buyers depending on the industry. And so we help them kind of see what that gap is to target that buyer.
Yeah.
I love that. It's such an interesting thing when you've got a business that you feel like has so much involvement for yourself, and that involvement is you doing the work to grow the business. And then you realize, and then you start to put people in place and systems in place that can grow the business without you.
And you're like, hang on a second. Like, I don't need to grow the business. I've got systems, I've got a team. Now I've got time, and it's growing without me. Like, do I like the real problem?
Really is not the business. It's the owner feeling like they're stuck, right? And then helping them feel empowered to like, that's the real goal is to help them not feel stuck in their business, which can make them feel stuck in their life as well.
Yeah, there are always two pieces. There's always what does the business look like? What does that look like as an asset separate from the owner? And then what is, where is the owner's temperament? What's happening in the business's life? And then what's happening in the owner's life?
And those two things have to kind of get onto the same wavelength somehow. You can have a business that's crushing it while an owner's personal life is going to utter shit. And that chasm is something that has to get solved. And so a lot of times, the entrepreneur's desire to sell may have very little to do with what's happening in the business. Like we had some clients that of them, both of the owners, the business was growing 50 % year over years, a manufacturing business.
It was a high-growth business, but both of the owners had lost everything in the 2008 crash that happened in the U.S., and so they were getting to this stage where they were like, I don't want, even though the business is growing, the bigger it grew, the more they felt like it was going to be likely that it was going to crash. So they were just scared of losing everything all over again when they had already gotten to a new level of the game. So it had nothing to do with the business.
It's just a fear story that enters into what if we could have sold for 25 million bucks, but we end up with nothing, just like we did 15 years ago. And so like, what if we end up in the same place all over again? Right. And so it's, I have to navigate those two. And so to the extent that I'm talking to your people of guys that are thinking about buying businesses. You have to understand that there are two parallel problems that you have to solve. What is the asset? What's happening within the asset?
And then also, where is the entrepreneur at? What's happening in the entrepreneur's life? I think there's this like, there's this fixation in the ETA world on the business itself, because that's ultimately going to be the thing that you keep. So you're worried about the P and L and the operations and the people and the product and all that stuff. I think the best deal makers that I've seen, both as a lawyer and as an advisor in the times that I've been in that position, the best deal makers spend an equal amount of time with the entrepreneur and try to help solve the entrepreneur's problems in their lives to the extent that they can. And they realize that the entrepreneur's life is a big part of this business; this business is an extension of this entrepreneur's life. And to the extent that they can solve what's happening in the entrepreneur's life within this transaction.
A lot of the time, they can have a lower entry point price-wise. You can get it for a cheaper price, and you can be a little bit more creative in how the deal gets structured. If the seller likes you and you spend the time understanding where the problem is, a lot of times, a broker is the kind of goalie with the seller.
So you don't get the true answers from the seller about what's happening. You have this kind of polished answer, but if you can find a way to navigate that, then you can get a lot to get that answer comes from a human who has emotion behind it, and work out what that emotion is behind that answer.
Yeah, yeah. You talk about personal purpose as well. Is this a bit separate, or is this sort of on like, people make an exit, or if they free up time in their business, is this something that you work with people to help do, like, have a bit more like personal purpose and about in their life or what you know?
Talk to me about that piece. Yeah, that's, I would say that's been- and well, what's the name of your book too?
The name of the book is the creator. Let's see the creators' call. Which you can't really see the sub line is break free from the default path, live your personal purpose and unleash the creator within. So the book is a little bit of my story of going into law, leaving law, becoming an entrepreneur, having some financial success as an entrepreneur, my wife getting cancer and kind of like going through the roller coaster of life and trying to figure out.
Okay, cool.
What life is inviting you to create from the difficult moments in life? Like when I was experiencing a panic attack from a law firm, I thought that my life was falling apart. Now, with a little bi, with the benefit of hindsight, that happened a decade ago, I'm so grateful for what that experience was because it ultimately opened me up to go down this new path that was so much better for me.
And so I kind of go through my wife's cancer, some difficulties with my parents growing up, and try to look at some of these darker moments, the moments that you don't see on social media, and think of what those invitations were to do? What were those invitations to create, and what got created from that process? And how can I see what the common thread is behind all of it?
I believe that we're all creators and are kind of put on this earth to create. Think entrepreneurship is one way to do that, and not the only way. And I think a lot of times when you can find a business or a way to work and make money, when you can find a way to generate economics in some path that transcends the economics, if you would do the work for free and you can also get paid for it, I think that's kind of the holy grail.
Think entrepreneurship has changed over time, where it's less, it's more about just kind of arbitraging markets, and it's become much more of a financial mechanism and not kind of this life calling that I think it used to be when it wasn't so sexy and so prestigious 20 30 years ago and so I think entrepreneurs have kind of lost this the heart element of it and it has just become Spreadsheets and you know does the deal pencil and I don't think entrepreneurs are asking the question enough of I like this work Is this work that is worth my life force doing? Outside of the economics, and I think if you're a little bit more patient.
You can find the work that's worth doing outside of economics, a nd the economics can be spectacular for you. But if you're not going to ask the question and that goes in stages, I get if I'm listening to this and I'm a lawyer, I'm like, well, screw you, dude. Like I'm just trying to not be freaking miserable. Like I can't even think about.
What I like, Wolf.
And so in the book, I tried to address that and kind of say, even if you're at this earlier stage where you feel like economics are the only thing you're trying to optimize for, you can still ask these questions and you can still find the thing because you'll find that if you feel like the work is worth doing, that is ultimately I think if you look at all the things that I failed at and the couple of things that I've had success at, the things that I've had success at were things that I had convinced myself for whatever reason that the work was worth doing even outside of the economics.
And the things that I failed at right when I hit my first kind of in pass, I decided to quit because I was only doing it for the economics and the economics didn't come easily. so I'm like, screw it. I'm not going to do it. So anyway, I try to help people, whether they're an entrepreneur in a business or a working person who's kind of trying to find their path because they know that the, only know that the path that they're on isn't the one it's, I try to help people through that pivot point of what I'm doing isn't what I want to continue to do.
How do I find that? Purpose, I think, is a short form of like, What is my purpose? I think that's a very difficult question. I wrote the book because I didn't know the answer to that question of how to find your purpose. I felt like I had done law, I had done entrepreneurship, I had kind of been successful. I had found some success on this kind of very well-trodden path, but I felt like I still didn't have my thing that was kind of clicking the way that I expected it to.
And so I wrote the book as an exploration of that question. And the answer that I ultimately came to is a question of what is my purpose? A better question is probably, am I supposed to, what will bring me joy, and create right now? And that is, think of a path, a thread to pull on that can open up new worlds for you if you allow yourself to explore.
I agree with that. I think people have different perceptions of what purpose means. And some people may believe that it's like the purpose is like an end goal, right? Versus, like I'm with you, is like, how do you create something that helps you enjoy or create something that you do enjoy? My belief around purpose is that of what it is like to do, like you say to how do you create something right now that you can enjoy? Right? That's what you mentioned.
Were your words that I just heard you say? I believe that it is more about like right and enjoyment. And how do you have that enjoyment right now? And typically, like, whatever we do in life is like, if we're creating a breath in, we're creating a breath out. Whatever we do is some form of creation.
And how do we do it, how do we work out what that is? That is, you can have it in your business, and then you can have it outside your business, or it can be in one. It doesn't need to be like my money path is like the has to be the thing that I have the most enjoyment from. Can have some level of enjoyment, but it could be different to like say surfing or a different sport like car racing or whatever it is. Have you found that with people that you worked with like in the business?
Yeah, I found that the more intertwined it is, not that everything has to be about business. Tell the story about how, after I sold my company, I thought maybe I wanted to be a pro pickleball player. And so I started to commit to pickleball. Played tennis in college.
And so I kind of started to commit to the process. The more I tried to learn, pickleball was always a hobby that I enjoyed. But the more I tried to make pickleball my work, the more I felt how pointless pickleball was.
And I felt like I was wasting my time, and when I was writing the book, I tried to quit writing the book because I felt like the book was too hard. I had originally set out to write a book on how to sell a company, and I ended up with this book on how to find your purpose.
And I wanted to write about P&Ls and accounting principles, a nd very safe in your head, logical things, not heart-driven, this other book that I ended up writing. And so I learned that pickleball needed to stay a hobby, and it couldn't be my, you know, it's a good release valve for me, and it's not.
I don't view it as important or essential enough to make it my work. Writing the book became more important to me than any of my other money-making endeavors, of helping people sell their companies, anything, all of my investments. The book became the most important thing at that time.
If you listen to some of the best athletes in the world, I listened to this thing from Roger Federer when he was retiring from tennis. And he said, I'm playing a point, whether it's a championship point or a qualifying point, is the most important thing in the world to me. Nothing else matters in my life than this point on this tennis court right here.
And so when you find your creation that can do that for you, that can shut out the rest of the world in that moment, for some surfers at surfing, for pickleball, pickleball couldn't do that for me. So it's a hobby that I enjoy, but it doesn't shut out the rest of the world to me. When I'm playing pickleball, I'm thinking about what I'm going to have for dinner. You know, it just does, it's not all encompassing.
Writing is for me, and surfing is for some other people. So, I think the less divided, when I was working at a law firm, I felt like I was putting on a show. I was pretending that I enjoyed the work because I didn't want to get fired. And that acting job was so draining to me that when I came home, I was exhausted. I had no life in me because I had spent all of my life force pretending that I didn't hate my job.
So the less divided, I think the less divided that you can make your life, the less segmented, fewer masks that you have to put on in certain areas, the more enjoyment, the more fulfillment that you'll feel because you're not living a divided life, you're living an undivided life and you can be authentic in all the stages.
So when I'm helping somebody sell a company, I wear these same clothes, I talk like I'm talking right now, I cuss like I do right now. And if they want a more professional person, if they want a guy who wears a suit or wears a different type of watch, like you're just not my guy.
And that's okay for me because I've learned that for me to contort myself to fit into a certain set of people is a trade that I'm not willing to make anymore. And I think as people do that, they'll be happier.
I agree it's just the fundamental principle, or the fundamental part of that is like just doing more of what you love versus what you don't love.
But it's like, I don't want to do I don't love this job. Like, I don't love wearing these clothes. I have to do it. But then it is a massive privilege. Like, there's work that you need to do. There are things that you need to do to get through that sort of survival phase, which is such a tough phase to get through, you know.
The conventional wisdom in entrepreneurship was that 15 years ago, it was to follow your passion. Now, if you look at most social media stuff, you'll have entrepreneurs who say follow your passion is stupid and not something worth doing. But it is the newer crowd that is wrong.
And I think the older crowd didn't know what they were saying. The real word passion comes from Latin pati, which means to suffer. And so if you make your work. That the suffering is worth it. And that is the crux of why pickleball wasn't worth it for me. The suffering that I needed to withstand to become a pro pickleball player, that suffering was not worth it to me.
I only wanted to do it because I thought it would be easy. And so even doing what you love, think that's a difficult... Writing this book was hell. This was nothing but a year of suffering. This was not... I mean, there were key moments where I felt like I had some insight or some breakthrough in it, but the majority of it, 90 % of it, was suffering.
But it was the suffering that I felt was worth bearing because the work felt important to me. It felt like it was something I felt uniquely called to do. The word vocation, vocare, to hear a voice, means work that you feel uniquely suited to do.
And so when you're doing work where you feel like, who else in the world can do this? I'm the only guy for this thing. And even though it may be hell at times, it's the hell that I am called to bear, and I will do this hell because it's important enough.
To help people out of their jobs, help plumbers buy other businesses, whatever. If that's suffering that you feel like you're uniquely suited to bear, then you're on it. That's the thing. That is your creation in this moment.
And that may change in the future, but that's a little bit of kind of a formula that I try to show in the book of what that kind of the false paths that I've gone down in an attempt to find it.
Awesome, man. Congratulations on writing that book. It's the creator's call, right? Can we, yeah, let's drop a link to where that is. Do you want to?
I think my Chief of Staff is gonna, I know you gave me some homework that I didn't know I did perfectly beforehand, and so the creator's call will be on there.
Yeah, cool. All right. I'll drop a link to the creators' call. And also,o I think I'll just link to your LinkedIn, as well. Unless there's anywhere else that people would.
I mean it's on Amazon. That's where that's you can go, just Amazon, the creators call and and it's there or Raleigh Williams Co. Those are kind of the two places that I talk about it. But yes, perfect.
Awesome, man. Thanks so much for coming on, and thank you for the work that you're doing and for writing that book. It's just making people more fulfilled, and that's the best thing ever. So thanks so much.
Yeah, thanks for having me. It was great. We'll have to do it again soon.
Yeah, Cain. All right, thanks, everybody, for listening. I'll see you in the next one.
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Jaryd Krause is a serial entrepreneur who helps people buy online businesses so they can spend more time doing what they love with who they love. He’s helped people buy and scale sites all the way up to 8 figures – from eCommerce to content websites. He spends his time surfing and traveling, and his biggest goals are around making a real tangible impact on people’s lives.
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