Business Buying for Financial Independence · 2026-08-04 · 51 min
Key moments - from our scoring
Substance score
52 / 100
Five dimensions, 20 points each
Alan Underwood discusses his journey from managing his father's car dealership to launching his own operation in 2007, timed perfectly before the credit crisis - a nearly catastrophic start that forced him to pioneer unique customer experience strategies. His dealership grew to $16 million in annual revenue across two locations with 30 employees, high online reviews (4.8-4.9 stars), and 30,000 Facebook followers, achieved through operational innovations like 30-minute sales autonomy for reps and free oil changes for lifetime ownership to create habit loops. The episode explores his business philosophy ("pray hard, work hard, treat people right") and covers key insights for buyers: securing financing from lenders who back new operators (his breakthrough with a single regional lender), negotiating with landlords, and competing against established businesses. Underwood also addresses the emotional and family factors that led him to sell - multiple personal crises between 2015-2018 involving a newborn with severe birth defects, sleep deprivation managing three concurrent businesses, and cancer losses that prompted him to reconsider his definition of success and financial freedom beyond purely monetary metrics.
Alan systematically contacted lenders across local, regional, and national levels over months until finding one willing to back him. He then became their #1 dealer by demonstrating operational excellence and consistency, eventually closing 100+ loans per month with that single lender.
He leveraged habit loop psychology from behavioral neuroscience: bringing customers back every 3-4 months for free service created automatic purchasing impulses, leading to upsells on brakes, AC repair, and vehicle upgrades worth far more than the oil change cost.
He focused on eliminating customer friction (30-minute sales with full rep autonomy, no manager loop-backs), delivering exceptional service to build online reviews and social proof (4.8+ stars, 30K followers), and working with extreme discipline and integrity despite launching from a junkyard location.
Family crises between 2015-2018 - including a newborn daughter with severe birth defects requiring NICU care, chronic sleep deprivation managing three concurrent businesses, and deaths of in-laws from cancer - forced him to redefine what financial freedom actually meant beyond revenue metrics.
Sellers may have hidden motivations beyond money: family stress, multiple business portfolio fatigue, health shocks, or a sudden revaluation of what success means can drive exits at valuations below intrinsic value, creating buyer opportunities if you understand their real pain points.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains meaningful personal and business anecdotes but lacks actionable, novel insights about business buying/selling mechanics. The core substance - how to evaluate sellers' motivations and recognize desperation - is valuable but underdeveloped; most practical advice is either common sense (treat customers well, pray hard, work hard) or specific only to car dealerships (30-minute sales windows, free oil changes as habit loops). The 13-year business journey gets substantial time, but little strategic detail transfers to other contexts.
pray hard, work hard and treat people right
when we get here in the morning, we pray together and then we work hard and then we treat people right
Alan's personal narrative - selling a $16M business for $100K due to mental health crisis - is genuinely striking and rare for podcast content. However, the underlying frameworks are well-worn: the junkyard-to-success origin story, the importance of mindset and vision, the value of mentors and mastermind groups. The psychological angle (psychache, suicide ideation) adds depth but isn't analyzed with originality; it's presented as personal testimony rather than actionable framework.
I was valuing myself at $0.27. That's what a 9mm round cost
the pressure of a large family, pressure of the businesses and the pressure of the grief just collapsed me
Alan is a legitimate 7-8 figure operator (pizza restaurants, $16M car dealership, solar business, real estate, coaching practice) with 13 years at scale in automotive retail. He has actual skin-in-the-game experience as both founder and seller. However, he's now primarily a coach and speaker rather than an active operator, and the episode frames him partly as a cautionary tale/mentor figure rather than a current practitioner at peak execution. Relevant and credible, but not tier-one operator quality.
I've had several seven and eight figure businesses
I had two locations we had in business for 13 years, and for 13 years in a row, we'd grow in $1 million year over year
The episode is rich with specific details about Alan's car dealership ($16M revenue, 25-30 employees, 4.8-4.9 star reviews, 30,000 Facebook followers, 70+ cars sold within months, 100+ loans/month with one lender, became top dealer in country with that lender). The junkyard story is concrete (8 forty-yard dumpsters, fire, moving back to competitor's location after 2 years). However, on the meta-topic - what buyers should know about distressed sellers - there's almost no specificity: no pricing frameworks, no negotiation tactics, no data on how often this happens, no comparable transactions.
we had two locations we had in business for 13 years, and for 13 years in a row, we'd grow in $1 million year over year
my youngest daughter was born, and she was born with a severe birth defect. The landed her in the NICU for about six weeks
Tim asks sensible follow-up questions (what business was it, why sell, why didn't you regret it, what did coaching do for you) and shows genuine empathy. However, he rarely pushes back, challenges claims, or asks hard questions that a skilled interviewer would pursue. For example: Tim doesn't probe whether the buyer took advantage, doesn't ask what warning signs Alan missed before the crisis, doesn't ask if there were structural red flags in how Alan ran the business that led to the distress, and doesn't challenge the spiritual/prayer narrative when offered as business strategy. The conversation reads more as sympathetic storytelling than rigorous examination of the buying/selling mechanics that ostensibly matters to the audience.
That's incredible. Especially for that time frame.
That's awesome there's a couple things there that I want to touch on
Computed from the transcript - who did the talking, and the words that came up most.
In this episode, Tim sits down with Alan Underwood , a coach, speaker, investor, and entrepreneur, to talk about the seller side of small business transactions. Alan shares the story of building and selling a car dealership, including launching from a former junkyard, surviving a fire before opening, navigating the 2007 credit crunch, and eventually growing the business into a multi-location dealership doing roughly $16 million in annual revenue. Tim is an entrepreneur who believes everyone should explore the opportunities that business and real estate can provide on the path to financial freedom. He owns and operates a wine & liquor store, a software startup, a consulting company, and a growing portfolio of commercial and residential real estate. Tim's passion for independent business has led him to support dozens of other business owners. For over a decade, he has worked with businesses on strategy, processes, finances, and marketing. These experiences, along with analyzing dozens of other businesses for potential acquisition, have provided Tim with an immense knowledge base to pull from.
Transcribed and scored by The B2B Podcast Index.
The location that I chose, where I chose to launch my own business, had been a junkyard for 30 years. It was still a junkyard when I signed the lease. And then my junkyard caught fire. Now, not only did I have a junkyard, but I had a junkyard on fire.
I've got a wife and four kids depending on me, and I'm watching my dream burned in front of me. Welcome to Business Buying for Financial Independence. I'm Tim Delaney, and I help young professionals buy small businesses so they can escape the 9 to 5 and take control of their time, income, and future. If that sounds like you, hit the subscribe button and let's get into it.
- Today, my guest is Alan Underwood. Alan is a coach, speaker, investor, all kinds of things. We'll get into his story in a minute, but I have Alan on today specifically because he has sold a business. And so I wanted to share let him share his perspective as a seller of a business.
For all of you out there that are looking to buy. Kind of poke around and get into the mindset that might be going through a seller's head when you're talking to them. So Alan, welcome to Business Buying for FI. - Tim, thank you for having me.
This is a delight to be with you today and share some of my experience. - Appreciate it. So let's jump in with what kind of business it was that you sold. And give me a time frame of when it was.
- Yeah. Before I dive right in there, Tim, I just want to, you know, maybe set the stage a little bit the type of business that was car dealership. We had two locations we had in business for 13 years, and for 13 years in a row, we'd grow in $1 million year over year. Every year we had 30,000 Facebook followers, 4.
8, 4.9 star reviews, which is unusual for any car business. They don't usually receive high marks, but we took great care of our customers and had great employees, probably 25 or 30 employees at the time, and we'd grown to where we were doing about $16 million a year from starting off. We timed the opening of that business really perfectly for May of 2007, right before credit markets crashed.
And it was pretty certain that that business wasn't going to survive. Here's one. But it's a lot of work and a lot of prayer. We pulled through and eventually had something really successful.
- That's incredible. Especially for that time frame. How did you get into that? What made you open up a car dealership in the first place?
- Yeah, that is a really great story. And it starts actually with a fishing trip. And prior to starting my own business, I was working for my dad and some of his partners managing one of their car dealerships. And before that, I, as the car dealerships, actually would be the second business that I sold.
So before that, I had pizza restaurants. I'd started one location, grown to multiple and then sold to restaurants. My dad invited me to come manage a car dealership for him. I didn't think that could be very much different than selling pizza.
And I learned two lessons really quickly after going to work for my dad. Lesson number one was selling cars. Made a lot more money than selling pizza, and so that was a good surprise. The second thing that I learned was I hated being an employee, and really disliked the fact that somebody else could tell me when to show up to work, when to leave, how to operate.
And that's something I didn't know before I had that experience. So learned those lessons and pretty quickly decided that I want to do this for myself. And so just became a student of the business that I was managing, and got to a point where I felt like it was time to step out on my own. But that was a big decision.
The company that I worked for was well established. My dad had been there for over 25 years. There was a very clear path for me, being able to be there for the rest of my life and never having to worry about a job, never having to worry about a paycheck, but also never really being able to test myself and do what I really wanted to do. And so with all of that kind of swirling around and in the background, my wife was expecting our fourth baby and my dad and I were fishing together.
We're up at Lake Powell, a place that he loved, and I presented to him the thoughts that I was having and what I was wrestling with in this decision and what he shared there has actually completely changed the way I make decisions. And it really provide a framework for now, what I use with people that I coach as I help them make decisions. My dad was a minority and interest partner. He owned 10%.
His business partner, Tom Jones, owned 90%. So my dad had a very stable golden handcuff opportunity and Tom was financially free, was traveling, owned an airplane. All of the stuff that you dream about when you want to be financially free. And so I presented all this to my dad, and he looked at me and he said, Alan, I think that you really only have one question to ask yourself.
And that question is, do you want to be Mike Underwood or Tom Jones 20 years from now? And, you know, a couple of things, Tim, really stand out there is my dad had a lot to lose by me leaving. The location that I was managing was the number one store in both volume and profitability. In fact, the profitability of my used car dealership was higher than all of the new car dealerships that they owned.
And I was the number one manager. So for him to engage in this conversation in a way where he could separate his own interests as a part owner in this business from providing really great advice for his son to me is just amazing. But the clarity that that question provided for that decision and all future decisions has been so helpful because it got me past the how do I do this? How will it work?
What if it doesn't work and just put me into really my future self and determining who I wanted to be, rather than trying to decide how to do it or even what to do. And that's how I got in. I decided right there on that fishing boat that I wanted financial freedom. And so if that's what I wanted, the path that I knew I needed to take was to be an owner.
So I made the decision, not to his delight or his business partners’ delight. I opened Catty Corner from their location and they weren't thrilled with that. They didn't think it was a great the location I chose. They didn't think it was a great location.
And that's, you know, another fun story if you want to go down that path. But that's how I got into the business. - That’s awesome. There's a couple things there that I want to touch on.
First of all, the fact that your father was able to separate his own needs from giving you good advice is a fantastic lesson to any parent out there. I'm sure while he wasn't Tom Jones level of financial freedom, I'm sure you working there gave him a little bit more financial freedom than he would have with any other manager because he trusted you more. So that's incredible that he was able to do that. And then that mindset piece that you you mentioned earlier of just not being able to be an employee of, of somebody, you know, that you recognize that, and you knew that you needed to do something on your own.
So with that location, was it more of they didn't like that you were competitors or were they actually thinking about your own interest? And in that it was really just wasn't a good location for you? - Yeah. I'll share these pictures with you.
Tim, I don't know if you know how you leverage social media, but the pictures will tell a thousand words. So, you know, in a retail business, like cars or anything else, location is very important, right? Curb appeal means something. The location that I chose, where I chose to launch my own business, had been a junkyard for 30 years.
It was still a junkyard when I signed the lease. And so the first step was cleaning this place out. There's a 2000 square foot building on the property. It took eight 40-yard dumpsters to just to clear the garbage out of that building.
And so you can imagine what the rest of the property looked like. And my dad's partner, when I let him know I was making this decision, I just had one thing to say. He didn't say thank you for what you've done. He didn't say, I wish you well.
He just said, “I just want you to know you're making the worst mistake of your life”. And being young and certainly willing to punch back. I guess my response was, well, I just want you to know that one of us is making the worst mistake of their life. Funny about that now, though - It wasn't at the time it was here.
I'm working on this junkyard in full view of all the people that used to work for me. They would drive by and laugh at that experience. And then my junkyard caught fire. And so now, not only so now, not only did I have a junkyard, but I had a junkyard on fire.
And for anybody that's been through a difficult season, And for anybody that's been through a difficult season, they know how that feels. Yeah, here I am, 27 years old. I've got a wife and four kids depending on me, and I'm watching my dream burned in front of me, and several of the people that used to work for me drove over, and they didn't offer to help put out the fire. They didn't offer any consolation.
They just drove over to make fun of me. And, you know, I look back at that now. And what I appreciate in myself is even with the junkyard on fire, I didn't change the vision that I had. It was a setback.
But I didn't feel discouraged at all. It didn't change the vision. And, you know, for anybody going through a difficult season, your perspective on keeping, I guess, your eye on your vision and who you're becoming and not allowing even really difficult things like junkyards on fire to discourage you from what you want to accomplish is, is really important. Now, if we fast forward, once we got open, it took several months, especially with the delays from the fire.
Within just a few months we were selling over 70 cars. Within two years, I had put my dad and his partner out of business at the location across the street, and we actually ended up moving back into that much better location after two years. And that's where we were for the next 11 years. - Wow.
That's had to be a lot of emotion moving back into that building, putting them out of business. That's quite - - A lot of satisfaction. - Yeah that's that's a good overcoming adversity story. You know that should resonate with a lot of listeners of like there's going to be bumps in the road.
Whether you're buying the most profitable business in the world or starting from scratch, there is there's always going to be hurdles to overcome. And you can't let things get in your way or discourage you too much. You know, if Alan can overcome a burning junkyard and create such a big business, you can overcome whatever hurdles you're dealing with. Let's - I want to go back a little bit further for a minute.
And just how did you get interested in entrepreneurship in the first place? You know, you mentioned those pizzerias. Like what was your father was always was your father in the business and an owner growing up as well? Like, was that in your blood?
- No. My dad, like I said, had golden handcuffs. My dad got a degree in accounting, went to work for this car dealership doing the books. Then they hired him to come internal.
Then he ended up managing one of their locations and eventually to keep him employed and fend off some other competing offers. They offered him a small ownership stake. I wonder now my dad passed away about six years ago, you know, if maybe in some ways he didn't live vicariously through me. The best answer that I can give to to your question is people are interested in a lot of different things.
And, you know, like when I was in the car business, my brother, I have a younger brother who's very into cars and really anything machines. And he would call all the time and ask if I'd seen the latest, whatever that just came out, the new Porsche or the new F-150. And he was always so excited about these cars, and I didn't have any clue what he was talking about, because really, the cars didn't matter to me that much. People would ask what my favorite car was, and my answer to that was whatever car sold last.
And so one of the superpowers that that I was gifted with, and one of the things that's always piqued my curiosity and to this day is I just love business. And so, you know, some people like to people watch, I like to business watch. And the way that I got into the pizza business was I was managing six subway stores for a friend while I was in college. And he'd seen this concept for this pizza restaurant, was interested in it.
And so he asked me if I would go check it out. And so I would take a yellow notepad and I would go and sit in this pizza restaurant. And with the background of the systems and processes that subway had in place, which were excellent, I would just observe. And this was a little solopreneur who would open this place and was trying to make it work.
But from the framework of the subway systems and operations and everything they had streamlined, I could see the inefficiencies and recognize that there was something there, but there was also something that could be made better. And so I would count the number of employees that were working. I notice the inefficiencies in the kitchen. I would park out behind the restaurant and like, see what food was being delivered.
And after about 3 or 4 months of doing that, I went back to my boss and I was like, hey, this looks great, and here's how I think we can make it better. And he didn't want to do it. And at that point I'd sold myself on the idea. And so with, you know, the extensive experience of less than one year managing subway restaurants, I went to my dad and pitched him on the idea.
He suggested I talked to my uncle who owned restaurants. One of the funniest conversation told me never to get into the restaurant business. But, you know, I thought at 21 years old that I knew better than he did. And so I ignored that advice, which actually was really great advice.
And then I pitched the idea to my grandpa, and my grandpa gave me one of the funniest responses I've ever received. You know, here I share this idea and I'm all excited and it's going to work and I'm going to be a millionaire. And my grandpa just looked straight at me and kind of shook his head a little bit, and he said, Alan, that will never work. And I just thought he didn't understand.
So I pitched it again. And his response to that was, Alan, if you want to make any money, go sell drugs, sex, or religion. And, you know, looking back, I can't say that he was wrong. Those businesses seem to do well, but I also knew I probably wasn't going to be able to get into any of those businesses.
So, you know, contrary to all the advice given to me, I went ahead and plowed ahead and my dad placed a lot of confidence in me, and lent me the money to open that first location. It went extremely well. Within a year - We actually every year for like the next five years, we opened a new location together. - That's awesome.
Good, good. I like your grandfather's response. And restaurants are tough. That's one industry that I have no interest in whatsoever.
But you're you know that that franchise model like there is generally not a huge fan of franchises either for myself, but they do a great job of teaching those systems and putting systems in place, and they can be a great learning ground for people that are interested in business in general, which you learned from Subway. So you ended up selling those working for the car dealership and then opening your own, and you're doing gangbusters at the car dealership. Why sell it? What's or anything else you want to talk about running that operation, how you grew it so fast?
Was it just customer service or marketing? What was your I guess, what was your secret formula for growing it so well? - The first part of the secret formula was survive. 2007 was a very difficult year.
And, you know, starting a business or buying a business, there are seasons two businesses. And that season was extraordinarily difficult. I was you know, we we had bet the farm on this opportunity. I'd mortgage my house.
Every dollar that we had saved had gone into it. And that year, just by point of reference, it was so difficult financially that we were actually for Christmas that year. I can remember we were like at a goodwill just to like by blankets for the kids. That was Christmas.
And I can remember sitting in the car and being so embarrassed at the, you know, I was making, you know, take this at 20 years ago and I was in my low 20s, you know, mid 20s, I guess 25, 26. And I'm making 150, $200,000 a year. And that next year, I can remember filing on my taxes for 2007, and my income was $7,000. I was so embarrassed to go in and do Christmas shopping at this thrift store that I wouldn't even go inside.
My wife went in and did the Christmas shopping, what we could get, and I can remember getting her back into the car and and turning to her and just telling her, I - I promise you, we will never do this again. We will never be here again. Ed Millett says that the two most powerful forces in the world are a vision of who you want to become and who you're doing it for. And I knew who I wanted to become, and I knew who I was doing it for.
And that first year, one of the biggest challenges that we had was the car business really is a lending business. Everybody buys car cars on debt, so you're really selling debt with an asset attached. That's the business model. And the problem in 2007 is nobody was lending money.
And so our biggest challenge, and something that I realized that first year wasn't our ability by cars or our ability to sell cars, it was our ability to get financing. And so I went through list after list after list of local lenders, regional lenders, national lenders, and in the in the car business until you're seasoned as an operator - Nobody wants to allow you to use their money for your customers. You can't just go and sign up with Bank of America or Wells Fargo and sell their paper.
And so that was a significant challenge. And we ended up finding one lender. And that lender ended up really saving us. We became, over the course of the next four years, the number one dealer in the country, with that lender doing over 100, 100 loans a month with them.
And the secret to our success? They sent a rep out to ask that question, like, how are you guys doing so well, your little independent dealer, what are you doing that's different? And our rep came out and, you know, I'm sure she wanted some, you know, elaborate response. And I said, well, I can tell you what that is.
It said when we get here in the morning, we pray together and then we work hard and then we treat people right. I said, so our secret really is pray hard, work hard and treat people right. And she just kind of looked back at me quizzically. She's like, I can't take that back to corporate and let them know that's that's what you're doing.
And I said, well, you're going to have to make something else up, because I haven't figured out anything else to make this work. So that's what we do. And, you know, that really was the formula going forward. And, you know, I said, I've always been interested in business.
And my superpower attached to that is I'm able to see what small changes can make something just a little bit better. And that's what really serves me as a coach now is and able to see in people small changes that can help them be better. And so what I took to the car business was, you know, nobody likes going in to buy a car. You expect that you're going to be there for hours.
You're going to get, you know, let me talk to my manager and if you'll do this, I'll do that. I didn’t want any of that. So our model was that our salespeople had 30 minutes from the time that people showed up to sell them a car. They had the complete autonomy to negotiate their own deals.
We set a floor that they couldn't go past, but there was no back and forth. They didn't have to ask permission. They could decide what they were going to sell the car for, but if they weren't able to do something in 30 minutes, we'd pull them off and put somebody else on because we wanted people to do what they wanted to do. They came there because they wanted to buy a car.
We should be able to make that easy. So that was the little change in. There were some other innovations that we had business wise, but that was the key one. And then the other thing that we did is we offered a free oil change for as long as they own the car.
And my dad, with his experience in the car business, told me that that was the dumbest thing he'd ever heard of, that it would put us out of business. But the reason why I did that actually had nothing to do with free oil changes or anything else, is I had just read a book that talks about how the brain creates habit loops, and I recognized that if I could create a habit in somebody's brain by just bringing them back to my dealership every 3 or 4 months for an oil change, that when anything car related would pop up almost without thinking, they would either call me or drive to our dealership.
And those free oil changes always led to changing brakes, repairing AC, and ultimately people would be sitting there and see something that was one year newer or two years newer than what they were driving, and it led to a ton of sales. So, you know, and free is the most powerful advertising word on the planet. So I was trying to attach powerful advertising to powerful habit making. And that worked out really well for us.
- Yeah, that's I bought a car from a place that offered free changes once. I think that was free. Oil changes ended up costing me more than I would have spent otherwise on upgrades and repairs and all that kind of stuff because, you know, not that they're necessarily taking advantage, but they're being proactive and pointing things out that need attention. And you end up doing it because you're there.
And why not? They're telling you that this should be looked at and this should be you. Consider replacing this in a few months. Well, you may as well just do it now rather than come back again.
So I yeah, I don't understand why all dealerships don't offer that, because it seems like a no brainer to get people in the door. But that's good of you to recognize that quite a long time ago too. It seems like, you know. So your secret recipe of praying together, working hard and taking care of customers got you some, some good success along with those little tricks of free will changes.
You know why? Why did you end up selling the business? Yeah, well, This is what I call the best, worst mistake of my life. And when I speak on stages across the country, across the world.
Now I share this. And because depending on your perspective, you could see it either way. But here's what happened in 2015, my youngest daughter was born, and she was born with a severe birth defect. The landed her in the NICU for about six weeks.
And during that six week period, you know, it was touch and go with her life and myself or my wife was at the hospital pretty much all the time. And Marin was our eighth. So we have eight kids and, you know, trying to manage seven other kids and school and schedules. And at that time, I not only had the car business, but, you know, we had these repair shops that we had opened, we had an insurance company that we'd opened.
And so I'm trying to manage 2 or 3 businesses, seven kids, you know, very sick kid in the hospital, obviously just super stressful, you know, thankfully came out okay. But then she didn't sleep through the night for the next couple of years, and she would sleep 20 or 30 minutes at a time. So, you know, we're super sleep deprived. And then in 2018, we found out that my mother in law had cancer and we lost her a week later.
Obviously, a huge shock. 13 months after that, my father-in-law's cancer came back and ruptured his carotid artery. And we found him bleeding to death on the kitchen floor. And I ended up administering to him what ended up to be a lethal injection to help him pass.
And that had a severe emotional, psychological impact on me, was dealing with really debilitating PTSD, depression, anxiety. And then, you know, Covid hits early in 2020. And then October of 2020, about 13 months after my father-in-law passed away, my dad had a massive stroke and passed away as well. And I just was completely unprepared for the grief for the depression.
I got really sick after my dad passed away, and I don't know if that was physically sick or emotional sick or it was probably all of it. But, you know, I didn't go to my dad's funeral, I didn't go to his burial. And I can remember telling my wife, I would be happy if she would just throw me in the same grave with my dad and bury me. And within a few months after that, I was I was sitting in a pickup truck looking at a handgun and wanting to end my life.
And looking back on that now, I recognize what had happened is there's a term that I've learned since then that helped me to describe what I was experiencing, and that's called its “psychache”, and it's where it's not really depression, it's not really grief. It's this combination. And what it is if you've watched a building be demolished and they like, set detonations at the top floors and it goes down in the building, just kind of collapses in on itself. That's what happens within the mind when it's under extreme pressure.
So, pressure of a large family, pressure of the businesses and the pressure of the grief just collapsed me. And I ended up, you know, I looked back now and what happened was I was valuing myself at $0.27. That's what a 9mm round cost.
And in an effort to figure out how do I relieve some of this pressure, I also lost all perspective on the value of the business that I built and all I could - The only thing I could feel was the pressure of it. To me, it held no value and I just, I wanted to get out. And so I found a friend who was also in the car business, also very successful, and let him know that I was getting out of the business, didn't I didn't explain to him why and asked him how much cash he had on hand.
He said he had about $100,000. I told him I thought that would be just fine and we literally tend to not sign paperwork. There were no attorneys involved. There was literally - he handed me cash.
I shook his hand, handed him the keys, and I walked away. I then asked on another podcast what I think I lost in that transaction. And the reality is I have no idea. I mean, we could go back and calculate business values and that kind of stuff, but what I gained was an opportunity to save my life.
And, you know, ultimately what I make the same selling decision today. No. No way. On the other end of that transaction, I would make the buying decision for sure.
You know, even if all I did was turn around and, you know, it'd be pretty easy to realize 100% return and sell it for 200,000, even if that's the best you thought you could do. Yeah, but there were multiple millions that were left on the table in that transaction. But I never regret it. Well, that's not true.
There was a period where I did regret it, and I beat myself up about it pretty badly. But I don't feel that way today. Recognize that given the set of circumstances that I had at the time, I made the best decision I knew how to make. And there's a lot of reasons why that decision wasn't a better one, and we can get into that.
But, you know, I'll pause there and and let you guide the conversation where you want to go. - Yeah. I mean, first of all, I'm sorry for all of the loss that you went through. That's it's a lot in a short period of time for anybody.
And I think it, you know, it does kind of show that it doesn't matter how successful anybody is, that there's certain things in life that are going to bring you down, and you have to try to do your best to be prepared for them being successful, having businesses, having all that, you know, monetary gain doesn't let you escape from life's reality sometimes. one of the reasons I wanted to have Alan on to tell this story of how he sold his business and what he sold it for is partially to show people and not to encourage anybody out there to go take advantage of somebody in their situation, but to show people that we often assume that we know what other people are thinking.
And in reality, we never know what somebody else is thinking or what their situation really is, and what reasons they might have for doing what they're doing at that time. You know, Alan mentioned you did go through a period of regret for selling it, what is probably for pennies on the dollar. But - just because he sold it very cheap doesn't necessarily mean that the buyer took advantage of him. It doesn't mean that Alan was, you know, taken advantage of.
It just means that his situation was was what it was, and he needed to do something about it. And in a way, it helped him in the moment of, of that sale, you know, I guess to so to somebody out there that's listening and says, wow, like, that buyer should be ashamed of himself. Like, how, how dare he just hand you $100,000 for such a successful car dealership? What would you say to that person?
Well, I think the the first thing would be to share what happened after. So there's two points. One of those was there was one day in particular, and I had started another business after I told the dealership, the solar business and my daughter, it was probably 5:00 in the morning, 6:00 in the morning. I'm sitting down on the couch thinking about the challenge of growing a new business.
And what did I really leave, you know, on the table with the last one and kind of woe is me. And she sat down on my lap and she said, you know, to this day how she even had this on her mind to have no idea. But she said, dad, do you like the car business or the solar business better? And in my mind I was like, there were a lot more zeros attached to the car business.
Like, you know, that's an easy response. But I said, “I don't know. Which one do you like better?” And she said, “Dad, when we had the car business, you were gone all the time.
” “And with the solar business, you're home all the time.” “I like the solar business better.” And, you know, such a powerful reframe for me that, you know, my my daughter had one metric of success and that was, is my dad home or not? And, you know, we'll often we'll buy a business or start a business.
And what we say is, I'm doing this for my family. And I don't think anybody's insincere in saying that. But the reality is, is a lot of us lose sight of that and our desire to grow and achieve overcomes really what the initial design of the business was in the first place was to give us more time to be with our families, and that I'm not going to say that that was the last time I thought about it, but it reframed it so powerfully for me that it really stops the regret. And then a couple of years later, I'm still good friends with the guy that bought the business.
I talked to him on a regular basis. He's doing extremely well, not just with the location that I sold him, but other dealerships. He's open, and I sat down with him just to see how things were going, and he said, you know, I kind of have a hard time talking to you about this because that location is amazing, is doing great. And, you know, I got a good deal on it.
And I'm not really sure how you feel about that. And, you know, he didn't know what I was going through, what my motivations were for selling. And so I took the time to explain that. And I said, I just want you to know how grateful I am.
I made a decision. You got a great deal. But I also feel like I got a great deal. Now, financially, we could say that it wasn't a great deal for me, but it gave me exactly what I needed at the time.
It needed me. It gave me space to begin the process of healing from the trauma and the grief and the depression that I was experiencing, and I wouldn't have had the freedom to do what I'm doing now without that experience, because I don't know if I had the courage to sell and walk away. I think I'd still be doing it if it weren't necessarily the best thing for me. And you know, I've now discovered really what I love doing in a lot of different ways.
I, you know, became a pilot. I discovered this new hobby of flying that has transformed my life in a lot of ways. I'm now able to sit in rooms with business leaders that are navigating equally difficult circumstances and show up as somebody that understands what they're experiencing. If all I had ever experienced was extreme success, you know, the business keeps growing and then we exit for multiple millions.
There's no way I could sit down with somebody that's going through divorce or dealing with depression, or they just lost everything in an investment and be able to understand how that feels and help them through it, because I had to learn how to go through it myself. And so that experience has been so valuable. So I'm grateful that it happened. Certainly wouldn't make the same selling decision today.
But I'm a different person today. And I have, you know, I work I work with a coach, I have a network of peers that advise me now, and I didn't have any of that then. And so I made the best decision I could. So I wasn't a victim.
And I don't feel victimized by that decision. - Yeah. That's good. That's a good, good mindset.
And you touched on you've touched on mindset a couple of times. I also want to point out that that story with your daughter is heartwarming, that the fact that it is important for all of us in business and in work, will never remember that you stayed late at the office and worked too much. But your kids always will. So just, you know, always keep that in mind whatever profession or business you're in.
And then, you know, you touched on getting around people, coaches, mentors, and masterminds. I'm personally a huge fan of that mindset. You know, we're both in a group together You know, we're both in a group together You know, we're both in a group together and there's other groups out there. When did you discover that that type of thing coaching, masterminding, mentoring and what has it done for you since?
- A really great question. Ultimately, the decision to sell - part of that decision was made because I was doing it in a vacuum. And my dad and my father-in-law were my business advisory network, and I really didn't know anyone else who I felt like I could sit down with and share the success that I was having, but also the challenges I was having, and get trusted advice on how to navigate that. And that was a big part after that, and getting to where I am today was intentionally looking like, where do I find other people who think like me, who have built businesses who, you know, aren't satisfied with the 9 to 5.
And it took a couple of years and then and I tried on a couple of different masterminds, and some of them have added a little bit of value. But it wasn't until I found the current mastermind that we're in together that there really was some acceleration. And now, you know, my wife and I have had this conversation. What if the depression comes back?
What if you get anxiety again? And my response to that is easy as well - I know today that if I'm facing difficult challenges, I can pick up the phone. And I have a personal relationship with 200 or 300 other business owners that I can reach out to, and they'll help. And that is such comfort and an advantage.
And then, you know, I hired a coach about two years ago to help grow the real estate business that I was working with. And also there's coaching practice. And, you know, coaching and community are two different things that serve different purposes. But both of them are accelerants.
So, you know, if you can afford to do one and not afford to do the other one, you know, pick one and run with it. If most of the guys that I know that are most successful have both. They have a community that they're part of, but they also hire coaches to help get them to the next level. And you see that in sports and business and politics and public speaking and across every area of life, those who perform at the highest level recognize the value of a coach to help push them or pull them or prod them to that level.
- Yeah, yeah. And on that note, do you want to talk a little bit about the kind of coaching that you do for others? - Sure. So the tagline for my coaching practice is mentoring in the moments that matter.
So, you know, I've had several seven and eight figure businesses. So there's a lot of coaches that can help with mindset. And certainly I do that. There's a lot of coaches that have a particular business strategy that they can help with.
Certainly I can do that. And so I stand at this really unique intersection of psychology and strategy, where the first thing with anybody that I'm working with is understanding what their mindset is, how are they talking to themselves? How do they view the world and their business? What are the real challenges that we're facing internally?
And then we can address those together, but then also doing a really deep dive on their business operations and identifying are their systems, processes, or procedures that we need to bring in. You know, one of the things I look back on and laugh about myself here. I'd grown this car dealership to $16 million a year, and I still did all of the book work for that entire time in 13 years, because I didn't know that you could hire somebody virtually to do it. And I didn't want to pay for somebody locally to do it.
And now I have, I don't know, eight or 9 or 10 different LLCs. Maybe there's more than that. I have one bookkeeper out of the Philippines that's been with me for the last 4 or 5 years, and I think my average payroll for her to manage the books on all of those entities is like $200 a month. And so, you know, certainly I exchanged a lot of time doing book work for that business.
So those are the experiences that I can bring to the table also is, hey, you know, this is a really low dollar activity. Let's get you doing what produces money for the business and eliminate the things that other people can do much better, much quicker and much less expensive than you're doing it now. So that's where I work. My typical client is an entrepreneur or a high level executive.
I've worked with Dennis and doctors and orthodontists and vice presidents of major banks and contractors and cabinet company owners, people trying to buy a business, sell a business. So pretty broad range there. But it's people that are facing a change, whether it's a change in business or change in life, and they need some additional support to navigate that. - Yeah.
And that's you know, like you said earlier, having a coach in your corner to help navigate those, those changes and those kind of periods of life is super helpful. Also, having a group of people in the form of a mastermind or programs like that that you can get multiple voices on a on a situation can really help as well. So if you're if that description of a person fits you and you're interested, make sure you reach out to Alan. See how you can help.
Anything else that you want to leave the listeners with? Any advice in business or life in general? - Now, all I would say is that if I look back at the great decisions that I've made in my life and the ones that have not been so great, the great decisions happened when I had a mentor or someone like my dad, who's sitting on the boat and can help me see things that I can't see and can ask questions that I'm not asking myself, and whether that's in a professional relationship and it's a paid engagement or just somebody that you can trust, you know, in your community, there's nothing more valuable than having another set of eyes on what you're doing, whether that's life or business and being able to trust that.
And then the other thing is, what I needed the most at the most difficult time was hope. And there's going to be people that listen to this, Tim, that are navigating a divorce or they've just received a terrible diagnosis or they've lost somebody that they love or their business is struggling or investments have gone bad. Those are what I call the moments that matter most in our life. And it's the points in life that really clarify the importance of relationships, that magnify the decisions that we make.
And if any of your listeners are navigating something like that and they just need somebody to talk through it, I do that without any commitment. And then if there's an engagement behind that, that's fine. But having gone through that myself back, if I, you know, show you the screensaver on my phone, it has two words. And those, those words are, be there.
And I've just made a commitment to myself into a world that I want to be there for people that are navigating those difficult things. Because that's what I needed most, was somebody to be there. So I want to thank you for allowing me to be here with you and have this experience. And I love what you're doing, the community that you're trying to build and the the information that you're providing, buying a business is a big deal.
And if you do it right, it can be a huge blessing. And if you do it wrong, it can be a huge burden. And you and I have both seen both sides of that coin. So helping people through that sure, as a service to the world.
So thank you for what you're doing. - Thanks for saying that. And thank you very much for being here. I really appreciate you sharing your story and offering to help anybody out there that is going through something right now.
Don't hesitate to reach out to Alan. It's amazing person with a big heart, so definitely reach out if you need it with that. Thank you everybody for listening today. And thank you.
Alan, for being here. I look forward to seeing you all again soon. Cheers. Thanks for listening to Business Buying for Financial Independence.
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