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Success isn’t just about hustle—it’s about surviving the chaos of growth.
Jason Long knows this better than most. After building a 30-person agency, he lost it all in the 2008 crash, nearly died in a horrific car accident, and spent years rebuilding both his businesses and himself.
In this episode, Jason and I get real about what scaling actually takes—the mistakes most entrepreneurs make, and the systems that separate struggling founders from professional CEOs.
Here’s what you’ll hear:
- Why 80-hour work weeks are a badge of failure, not success
- The accident that forced Jason to rebuild his brain—and his businesses
- How private equity taught him the power of financial literacy
- The frameworks he blends (EOS, OKRs, forecasting) to actually scale companies
- The mindset shift that frees entrepreneurs from burnout
This one’s raw, practical, and packed with lessons you can apply today.
👉 Looking for a roadmap to scale with less stress? Let's talk.
🔗 Resources & Guest Links:
👉 Looking for a roadmap to scale with less stress? Let's talk.
🔗 Resources & Guest Links:
- Jason Long: Website, Ascendance, Tangent Solutions, JH Media Group
Creators and Guests
Host
What is Beyond 8 Figures?
At Beyond 8 Figures, we believe in DELIBERATE entrepreneurship. It means creating a solid foundational framework for your entrepreneurial journey, building from a place of passion, and intentionally aligning your actions with your goals so that you can create success on your terms.
Join A.J. Lawrence, the journeyman entrepreneur with several 7 figure exits, as he shares honest conversations with successful entrepreneurs about their experiences starting and scaling businesses to $10M and beyond, the realities of being a modern-day entrepreneur, advice for practicing deliberate entrepreneurship, and more!
[Intro]
A.J. Lawrence:
Hey, everyone. Welcome back. It's been a bit, but today I'm really kind of excited. I've talked about being in the Dynamite Circle in the past and really some really interesting people. Recently I've been working on a project that hopefully I'll be able to talk. But a good friend of mine suggested as I've been working on this project to talk with Jason Long. Jason is famous in the Dynamite Circle and outside the Dynamite Circle for doing some incredibly amazing things. From his own companies to rolling things up into a private equity structure, to his own coaching, just, you know, tons of cool investments and just always a really smart, nice guy. I've never met Jason before. So as he sits there right to the side on the camera, it's kind of funny. But it was like, oh, that'd be cool. I've always heard amazing things about Jason. I've seen great things about his writing. I've read great things that he's written. So we've been chatting on this project, he's been nothing but this amazing font of information and like, oh, did you think about this? Did you do this? Have you? I'm like, okay, I have have 20,000 more things to work on. But it's been really great. And I thought it'd be wonderful to have him on the show to talk about his journey, talk about some of his experiences, and just share with us. So before I keep rambling on too much, Jason, thank you so much for coming on the show. I really appreciate this.
Jason Long:
Absolutely. I'm excited to talk. Appreciate you having me on here.
A.J. Lawrence:
No, this will be cool because you've done so much. And I knew I just couldn't do it fully justice. Can you kind of share just a bit about your journey because there's so many cool moving parts going on.
Jason Long:
I started my first business in '94 as a high school student. My mom really wanted me to get a job and so I started working as a bag boy at a grocery store. And I immediately realized that that was not for me. And so I saw people every week or so, people would come in to the gumball machines. There's this giant rack of gumball machines and they would just take money out of the gumball machines. And I was like, wow, that's so much easier than bagging groceries and cleaning up bathrooms. Which by the way, you'd think they have custodians to do it or janitors do. No, like they put the bag boys in to clean up the bathrooms and fix all sorts of other problems. They used to, at least. So I just got done one day like cleaning up a disgusting bathroom and I was watching these guys just pour money into a bucket and I was like, yeah, there's a better way to make a living. So I saved my money from working at the bagging groceries and I'm not very creative. So I bought some gumball machines and I started putting gumball machines in at friends’ families’ businesses. So like an auto repair shop like other other local businesses. And that's really how I got started in business. I mean, that's how like that was my personal first initiative. But I come from a long line of entrepreneurs. My grandfather was a very successful entrepreneur, my mom was a very successful entrepreneur. So I kind of knew. Not new, but I found it easy. Yeah, I found it easy because I had a lot of mentorship and a lot of help moving forward. And so I did that. And then I was in high school, so I opened a paintball store and, and that actually did moderately well for like a 16, 17 year old kid with like an actual brick and mortar store. Closed that window, went to university. And then in university I was a terrible student. I just, I didn't see the value of what university had for me personally because I knew I was probably never going to go work at somebody's business. So I started a business in school and before I dropped out of university, the business was doing pretty well. It was paying for my living, it was paying for everything. And I realized I was failing at university and I was failing in business because I was trying to do too many things. So I just let go, let my parents down. They were very upset and I went to pursue business and I told them, don't worry, if I need it, I'll go back. It's been 25 years, no one has yet to ask me for my diploma. So I think, I think I'm going to make it out with this one. So, yes, I went on to do that. Within a few years we grew a reasonable sized business. We had like this really nice office. It was doing great. I was really happy with the way things were going. I will say we built a really brittle business in the beginning because I didn't understand what I was doing. I didn't know what I didn't know. I didn't have great leadership or mentorship like my parents. My mom's businesses were really different, much bigger businesses. My grandfather's businesses, he was gone by that point but his business was tremendously bigger and I didn't have good mentorship on that. And so when the 2007, 2008 crash happened, my business tanked. And then shortly thereafter I got into a really bad car accident and I, and I really had to start, start things over. Almost done. I'll make the rest of it fast.
A.J. Lawrence:
No, no, no, no, no, that. Because I really wanted to bring, you know, come back to that because I've been reading a bit about what you've discussed on that. It's really fascinating. So keep going. Yes.
Jason Long:
So then that put me to around 2012. The business went from 30 full time people in 2007 to three of us in 2011, 2012. And then I started rebuilding it again. I got it back up to like 1012 people around 2015. And at that point that's actually when I joined the DC, the Dynamite Circle. Started doing things quite differently. Like learned from, realized I wanted to have a fully location independent lifestyle, started traveling a lot more, started meeting a lot more entrepreneurs all around the world. Changed up my business a lot, then went into private equity, exited some, had a nice exit on private equity, had another exit with one of my other businesses during that time as well. And took some time off after private equity because it was pretty tough, pretty stressful and wanted some time with my family. And then now I'm working on a couple other businesses.
A.J. Lawrence:
You said early on it was a lot of, and I'm going to put words into your mouth but you didn't have the mentor. So it sounded like there was a lot of just like rubbing of sticks and hoping things happened early on. Housing crisis, you know, economic, I saw that across a lot of businesses. We lost so many clients, but I got new clients. But it was luck. You got involved and your private equity was long term care. Correct? Now, from rubbing sticks and trying to figure things on the fly, or as I always call it, you know, building the car as you're driving down the highway going 90 miles an hour to one of the most process driven, report CYA, you know, cover your as$ processes, and private equity. How did you evolve to be able to handle that and do that? Because you and I have talked and your spreadsheets are amazing. The way you, you know, and that's just a very, that's just a tool. But your thought process of how you use these tools, it's incredibly well structured. The insights you're able to gather and sort of the way you build them to gain these insights is, it was pretty intense. There must have been some interesting learning period that you pushed yourself through to then be able to evolve into this private equity space.
Jason Long:
Yeah, that was essentially just me getting my as$ kicked over and over and over and over again. So I run small businesses for a long time and I'm very familiar with balance sheet and a P and L and, and a basic forecast when I got started in private equity. But I was not prepared for the level of financial literacy that I was going to need to move into that space. I went into this thing like really having no idea the depth that I was going to get into, into that and the fact that I was going to have to become really good at it. And this is actually in my coaching, like this is what I teach a lot of people is these entrepreneurs that are founder CEOs that are scaling businesses that need to become professional managers. This is the stuff they're missing. In a lot of cases it's process driven leadership, budget driven leadership. You know, like how do you build a CEO's vision into a budget and then lead through that budget and manage through that budget, those kinds of things. Super, super important. And that's when you move into private equity. That's how they manage it. Because that's the only way to manage these larger organizations. And so essentially the way I got good at it is I went to my first board meeting. I wouldn't say I had no clue what was going on, but I would say close to it. And you know, like the CFO is going through the budget and they're explaining all these things, and they take a look at me and they go, what about this cell right here, Jason? What's going on with that? And I'm just like, in my brain, you got the face that's like, oh, yeah, yeah, yeah, no problem. Hey, CFO, why don't you explain that real quick? But in my brain, I'm just like, I got no idea what these guys are talking about. And every one of these people on my board were either very successful former CEOs, investors, and or mostly financial analysts. And these guys were rock stars at this stuff. And they ran circles around me. And the only way that I could really just show up was to know this stuff. And so at a certain point, relatively early on into getting into private equity, one, I started taking courses myself and just upgrading my skill set on modeling and finance and all of that. And two, I had my CFO just like sit with me for a few hours every single week and answer questions and go through stuff and teach me stuff. And then I kind of found that I had an affinity for it because I really saw the value of being able to manage these large, complex organizations through forecasts and through these models. And I understand. I started to understand the value that a CEO at that level really provides, which is being able to tell the future. The closer you can predict, the better you can be at predicting the future. Even if it means the business is going down, the more valuable you are at the private equity level to a board, because they need to know for their other investments, what's this business doing in that process?
A.J. Lawrence:
So from that first sort of like, what is this? What's the implications of this cell? And I love getting those questions. You know, media, you know, every industry you can always kind of, there's always a client who does that to realizing, okay, I need to start learning. You took some courses, you started working with your own CFO, you started pushing yourself. How much time did it take before you started going, ooh, maybe I can do something with this? What was that for you about?
Jason Long:
I realized immediately, not only could I do something, but I saw the power going in with a group of rockstar CEOs on my board that I saw immediately the value and the power of it. Like the first meeting, I was like, oh, I've been doing it wrong my whole life. It was obvious. And I would also like to point out I am a vision driven CEO. I'm more the visionary than the integrator here. This stuff did not come natural to me. But I also used to work in software development where you have to be super detail oriented, like super, super, super detail oriented. And it came really hard for me. So I tell everybody out there, if I can do it, anybody can do it, because it was against the grain for me.
A.J. Lawrence:
Okay, sorry. About how long did it take before you felt like you could actually do stuff with this? Not that you saw the value, because obviously you saw the value enough to start pushing yourself.
Jason Long:
Keep in mind, I was in the middle of doing a very challenging turnaround at the time so I was extremely busy, working 80 hours a week or more in a lot of cases. So it wasn't like I had a ton of time to really dig in, as much as I would have loved to have done it. So I would say somewhere between six months and a year.
A.J. Lawrence:
That dedication to push yourself. I think one of the things I've seen a lot, even in my own experience, when something is important, making sure you find that way of doing it. Yeah, it's that like, okay, 30 days before it becomes a habit, 90 days before you actually start barehandedly recalling stuff. But six months to a year before like 80% skill set of like, oh, okay. It is always interesting, but that's an important skill and you've taken it pretty far years later from it. Because I played with it.
Jason Long:
There's a little more to that story. So I was given a budget for this business. And like the CFO at the time, he was the CFO of a parent organization. So I took over a business unit that they were going to spin off and sell. So my job was to take this distressed asset, turn it around, stabilize it, and like stabilize it, see if I could turn it around and sell it. That was the goal, really. If I just sold it for any reasonable amount of money, they would have been happy with that because it was an asset that was just on fire and nobody wanted to touch it. And so I worked with the CEO, but they gave me a budget. And I looked at this budget. It took me a while to really go through it, and I was like, this makes zero sense. Like, somebody just made this sh!t up. And they did. They made that sh!t up. Somebody just rolled some dice and flipped the coin and put numbers in there. But the thing is, I was accountable to those numbers. And so I realized real quickly, like, I got to sit in front of this board every single month and they're going to hammer me on this stuff. I got to make sure these numbers are spot on. Otherwise I'm going to look like an idiot over and over and over and over. And I don't like being an idiot in front of really smart people, in front of anybody. Definitely not those we were talking.
A.J. Lawrence:
I'm using you for that very same thing in my project. You know, I keep you updated as I move forward. So I force myself to actually go through the steps to reduce my idiocy, not get rid of it, unfortunately, but at least keep it under control. All right, so you had this great reason and a great kind of negative thing behind you. Like, okay, I gotta do this. I'm going to take a step back because one of the things in which I've been finding as I've been talking with other entrepreneurs is all the stuff we do as an entrepreneur at times really is counter to our own well being. The stress, the hyper focus, the hours, all the things. Now there's so much great benefits, but if we're not careful, it kind of leads it. Now you not only have dealt with that, but you also had an accident that you had to kind of deal with and kind of recovery and bring through. And then you use that as kind of a catalyst on your journey. Do you want to maybe walk us through your recovery and then how you brought that into being an entrepreneur?
Jason Long:
Yeah, absolutely. I did have one other important note about the first thing you said about working all the hours and doing all this stuff and all of that. You know, after all of these years of work, I think the best entrepreneurs, maybe not in startup phase, but after startup phase, are not working. I'm sure they're not working, that they're working 20, 30 hours a week at most. The times when I've had the businesses that are smooth, they're running, I've set everything up, everything is going and really like, I just leave at any given time. Like the really good entrepreneurs, that's where they get to. I see a lot of younger entrepreneurs wearing this badge that's like, oh, I work 80 hours a week. I work so hard. And I tell them, that's not a badge of success, that's a badge of failure. You've done it wrong. If you're working that many hours, like, you are completely doing it wrong. As an entrepreneur, we take these risks, we do these things so we can have great lifestyles and we have businesses that support us having a great lifestyle. And so that was great learning. That was something that I really learned throughout my time building businesses. But, it's an important thing for people to know, especially people first getting started. And then next going into the accident, where would you like me to start on that?
A.J. Lawrence:
I’ll let you because I know a bunch of things happened all at once. I don't want to, you know, like I said, I've gone through a bunch of your podcasts. I've read multiple bio because you're on multiple websites of multiple businesses with multiple bios. So this is your story. I don't want to, you know, rephrase it in the incorrect way.
Jason Long:
Yeah. So let's go back to 2007, a couple years before that car accident. Things were going so good. They were so good, man. Like, I was making money. I bought this house. I was still 20 something years old. I was dating a beautiful, beautiful woman. We've been together for multiple years. Everything was looking so good. It was looking so, so good. I mean, not everything. Obviously, like there were cracks in the business. I could kind of see, like, hey, there's going to be a problem. But like, it felt so good. I felt so sure of myself. My ego was just growing so big. And then late 2007-2008 rolls around, the economy crashes. And when we were not well diversified in our client base and our business dried up, it dried up. It seemed like overnight. So we had all of these people working, everything going smooth, but we built a brittle business. We didn't have great contracts, we didn't have great recurring revenue. We didn't have a lot of the things that you really need to stabilize an agency business. And so when the economy crashed, a lot of our retainer clients and the ones that were on contract just killed the contracts. And we didn't have any recourse for that. We didn't have ways to keep people. We didn't have good recurring revenue outside of that. And the business just tanked. And I thought, well, we can probably wait it out. But we burned through all of our padding and then we just had to start letting people go. And we went from like 30 people down to like eight people in like three or four months. It was brutal. It was so stressful. And not only that, we had to move out of our office in the middle of the night. It was one of those where like, we didn't have any money. We couldn't pay rent the next day. We had all of our stuff in there. There was no coming back from it. We showed up at 10 o' clock at night, loaded up trucks with all of our stuff, moved out in the middle of the night. Fortunately, I bought that house. So I moved kind of illegally. I moved the last few people we had into my living room and ran the business out of my living room, and I slept in one room. And that sucked. That was really, really tough. And then finally things were coming back. Like, I was like, okay, yeah, we're doing good. Like, things are getting back on track. And, it was September 11th of 2009. I was going to a business meeting in Norcross, Georgia. I was driving with my creative director and director of account management. It was Ryan and Christina. I was in the backseat. We were driving down the highway at 75 miles an hour. Somebody was texting and driving, and they merged into us. Christina pulled away towards the median, and when she came back, she lost control. The car spun out into the one spot they were doing construction on the median. So the median was broken. So we t-boned into the median at like 70 something miles an hour. And that median came, like concrete came through the body of the car, through the frame of the car, through my seat, and hit me in the back and broke nine vertebrae. It cracked my SI joint, which is like right where your pelvis and your spine meet. It broke my pubic symphysis, which is like if your pelvis is like this, it's the part at the bottom. So my pelvis was like that. I had two or both. My lungs were collapsed. I had severe brain damage, heart damage, liver damage, kidney damage. Like, everything in my abdomen was just torn all to hell. Massive internal bleeding. I had to be cut out with the jaws of life. Like, you know, they just sliced the car apart to get me apart, and my back was basically, like, snapped backwards in half. And it hurt really bad. So I was actually really fortunate. I was knocked out. They say I woke up. I don't remember any of it. I got to the hospital. I only saw it in my paperwork. I told them, I'm fine. I would like to go home now. Go ahead and let me go home. I just. I'm feeling a little short of breath, but I'm gonna be fine. Don't you guys worry. And they were like, actually, we're intubating. You right now. And I was like, huh? And that was. And. And then I. They put me into an induced coma. I fell into a regular coma. I was like, from the inflammation of my brain. And then I was in a coma for, like two or three weeks or something. And I was in the hospital for months and months afterwards. And. And yeah, it was. It was a really, really hard recovery because I lost two really important pieces. It's that one make it really hard to be in a relationship without. And to make it extremely hard to run a business without one was logistics. So I remember they would give me this, like, map of my house with, like, a list of things that I had to do. And it would say, like, you know, what do you do first? You get out of bed, you brush your teeth, you put on your clothes, you know, whatever the steps you would take. And I would have to fill the thing out over and over and over again. And I remember the first thing I did, first time I did, they take a look and they go, oh, I see. I see you're gonna go get the newspaper from the front yard before you put on your clothes. And I was like, you don't know me, but I do see what you're getting at. So I couldn't do logistics. And then I temporarily lost the ability to look at somebody and no emotion they were feeling. And nobody knew that this was a problem. Like, you don't know. Like you don't realize that. You just think somebody's a total asshole. And so that caused me no end of trouble. And so without those two things, both my businesses, or not both, all my businesses at the time started to fall apart. I had a relationship with a woman that went on for a long time. And then that ended, you know, about a year after the accident, which was, I think, questionably, even harder for me. That loss was a serious loss for me. I was very, very upset from that. And then I ended up falling into a depression. And finally my dad got really sick, and he ended up in the hospital. He had Rocky Mountain spotted fever because we owned a farm together. And he got in a tick bite and got Rocky Mountain spotted fever, which can kill you. It had an 80% mortality rate before antibiotics. And so he was in the hospital with that. They thought he was going to die. He's a doctor. I went in to see him, I said, hey, dad, like, something. Something's wrong with my heart, my pulse. And he feels my pulse, and he's like, you need to go down to cardiology right now. So I walked down there, tell him Dr. Long sent me, and next thing I know I'm in the hospital too. And it was stress related and due to the heart injuries that I incurred as well during the car accident. So during that, at that point they told me like, you got to get out from under the stress or you're going to die. And there's not much we can do other than maybe give you a pacemaker, but you got to figure out how to get out under this stress. So I went home that day after getting out and after seeing the specialist, I made a one year plan to leave the city I was in. The next day it was six month plan, the next day it was a three month plan, the next day it was a six week plan. And the next day I left. And during that time I sold everything I had or gave it away except for my computer, my guitar, my bike, my clothes and my dog. And I left and started my life over. Yeah, I just left and just started life over at 30 something years old.
A.J. Lawrence:
Was that about the time you joined DC?
Jason Long:
No. Tom Libelt was a buddy of mine. Tom was in the DC and he told me, he was like, Jason, I met this group of people, you need to meet them, it will change your life. And I was like, great, yeah man, where's the meeting? I love meeting new people. He's like, Bangkok. I was like, I'm not going to Bangkok, Tom. And this was such a mindset shift for me and I've dealt with so many other people that are in this mindset now that are like, I can't go to Bangkok, I have a business to run, I have these things to do, I have blah, blah, blah, blah, blah, all these reasons why I can't do this. And what they don't realize is that by having a massive network of a huge network of amazing entrepreneurs, it will change your life. You, everything gets so much easier. And I didn't see it and I didn't know it and I didn't realize that taking that time and improving yourself as an entrepreneur is the number one thing that you can do and to make a difference in your business and in your life. So even though he invited me for 2012 or 2013, one of the first DC events, I didn't go. And I didn't go until I saw him go from running this little Atlanta based SEO agency to just traveling the world full time, hanging out with amazing people. I saw his pictures, his business started shooting up and I call him, I'm like, what are you doing, man? Like, how the hell did you do all this stuff? He's like, I told you. You need to come meet these people. And I was like, okay, now it's 2015. Where's the meeting? Prague. I was like, cool, man. I'll be in Prague. So I was dating another woman at that time. She and I take a trip to Italy. She goes home, I go to Prague. I meet all of these amazing entrepreneurs. It starts to give me clarity on where to go next, what to do next, how to grow things, and how to live this lifestyle that I always wanted to live. I realized quickly that my relationship with her isn't going to work because I want to go travel the world. And she wants, very legitimately, to have a very stable life in Atlanta, Georgia, which, by the way, she got married recently. We’re still friends. She's a fantastic woman. And so that was kind of like one of the other jumping off points in my life. So it took me a long time to get past this. It took me many, many trials. It was the hardest time of my life. Going through my businesses failing, my dad almost dying, brain damage, body damage. Like not being able to walk for almost a year in a wheelchair for six months of that, on my back for three months on, in wheelchair for six months. Having to recoup, recuperate, you know, after being formally very fit and just going down to like nothing. I was a swimmer in university, and then I was on the crew team in university. I was a triathlete. I am an avid crossfit athlete. And, yeah, I went to just like, when you don't walk for almost a year, your legs just turn into like bones and like a bag of flesh with no muscle in there. And it's so hard to see what body you've worked so hard for just go to nothing.
A.J. Lawrence:
Not even a year. I mean, just over two years ago, pinched a couple of my discs, just a hinged, and I was in bed for three weeks and another four weeks of barely, you know, walking like this everywhere. And my legs shriveled and it took forever before I could even do anything in the weight room. So you're recovering out of that. You've restructured your life. You've rededicated how you're going, approaching things. You've left the city you're in. You have your dog, your guitar. It’s like, if you had a pickup truck, you have a great country song there. All right, so come on. Go to Nashville and start writing country song.
Jason Long:
No, it would have been a great time. Like, I would have had all the stories to become a great country singer. I actually lived near a railroad.
A.J. Lawrence:
So you had everything as it goes, trains. All right, sorry, sorry. Let's go back. You do this. You sold your businesses. You sold your–
Jason Long:
I didn't sell them. I didn't sell them. They just struggled. I should have sold them. That would have been a way smarter idea. What I should have done. If I could go back in time and just smack myself after that relationship ended in 2011, what I should have done. If I knew then what I know now, I would. It would have been an absolute no brainer. I should have just called my business partner at the time and said, look, man, I'm not fit to run this business right now. I need another year or two to get my shit together. This whole thing just ended. I'm depressed. I'm having these problems. I'm not like, I'm having other issues. I have brain damage. Like, there's all of these things. What I should have done is made that phone call, put my stuff in storage, let my parents hold my dog for a little while, get my backpack and just travel the world. I had the money to do it. I had the time to do it. I was. I had been in a relationship for many years. I was unattached. That would have been, for me, the best choice is if I knew then what I know now, I'd have gone to Southeast Asia, I'd have gone to Bangkok, and I would have traveled all through Micronesia, Polynesia, Southeast Asia, Australia, all of that area. I would have done that for a year. Probably jumped over to South and Central America and then come back a year to two years later and just started it fresh. That's what I should have done.
A.J. Lawrence:
You did people like with your businesses. So how did things change? What did you start seeing? You were in your recovery, you were struggling. These businesses were struggling. You didn't take the time for yourself. About that time, you start getting involved with PE also.
Jason Long:
The people that I had remaining, which was very few, I wanted to make sure that they were employed, that they were taken care of. And that's I think that's one of the main reasons I didn't just bail on everything. I had a really dedicated core team of people, and I want to make sure they were okay. And I knew that if I just bailed, knowing then what I know now, they'd have been fine, but I didn't see it at the time. And so I stayed on and I reduced the company down to just the minimal so that I could pay for my lifestyle. And I had minimal responsibilities. I still worked, but like the company, when I cut everything down to just really just me and a couple other people, the company made money every month and I didn't have to work that much, and we had good recurring revenue, and I could take the time to recover myself. And it took me a while to get to that point, to let go of all the rest of the people, to really take it fully remote in 2012. Like, it takes some time to get to that. So I think around 2013, like I had taken it down to the bare bones, and I was just partying a lot. Really. Like I went out four or five days a week, party all the time. I had a great time, did lots and lots of activities, went out with friends all the time. It was fantastic. Actually, I didn't get into private equity until years later.
A.J. Lawrence:
Okay, I thought that was like ‘13 or so. Oh, am I getting the decades wrong?
Jason Long:
Yeah, it was 2019 when I got into private equity, so there was no way I could have done it in 2013. I was still recovering from brain damage from 2013.
A.J. Lawrence:
So sorry, I got that whole wrong. Okay, so all right. So you went through your teenage years, you know, as an entrepreneur. Teenage experience. Hey, let me have fun with what, you know, the capabilities. You did this, you exit, it happens. And you come out of this with this idea of your coaching program. So you want to maybe, you know, talk about how that developed and what's going on with that right now?
Jason Long:
So, man, so many things came out of that. It wasn't just coaching. So many things came out of that. During the time that I was doing private equity work, I learned all of these skills that I saw that so many entrepreneurs that are scaling businesses don't have. It takes this particular kind of setup, this kind of person to take a business from 0 to 1. But it's really hard for that 0 to 1 person to take it from 1 to 10. And so really what we see is that a lot of times people are growing through being in the right place at the right time. They were lucky. It's not that they didn't work hard, but they were lucky in a lot of ways. They saw something, they jumped on it, they made it work, they got it up here, but then they hit this ceiling where they just can't scale past that because they don't know what it means to be a professional CEO. They don't have that CEO skillset. They've never worked in a professionally managed organization. I saw this need for entrepreneurs that are scaling to learn these other skill sets because I saw, at the private equity level, they're doing it like this. At the small business, they're doing it like this. And there's nobody in between this teaching people how to go from here to here. And I thought, yeah, that's probably something everybody should know about. So rather than doing coaching, I didn't take that approach to begin with at all. I was like, let me just speak about this. Let me just do public speaking just to educate people, because I saw so many people with this problem. So I started speaking at DC events. I started speaking at other events just to teach, just because I like doing it and I like helping people. And then somebody was like, hey, you know, like, you should do some coaching work. And I was like, ah, like, maybe I could make some money doing this. And at the time, I was still working in private equity. I was getting paid plenty. I had huge bonuses. I was like, maybe, maybe not. I'm pretty busy. But then I saw the end of that business coming. I knew that we were going to exit that business. I knew that was coming to the end. I was like, well, let me just throw it out there and see how it goes. And so I was a keynote speaker at a pretty big entrepreneurship conference for a really big, really big one. And I had all my materials that I put up just teaching people how to do this stuff. And at the end I was like, get my materials, fill out this form. Like take the QR code, take them to the form, fill out this form and get my materials. And at the end of that, the form was something that said, would you be interested in working with Jason as a coach? How much money would you pay? 3,000 a month, 5,000 a month, 10,000 a month. And I had like 20 people say, I'll pay you $5,000 a month to be a coach. And I was like, cool, we got a business. And so that was how it started. And I just started working with a handful of them. I realized very quickly that I could really only take four clients at a time just because I'm busy with other businesses. And I would get people's businesses mixed up which is really embarrassing to say if I have more than four or five at a time. So I scaled it back to just be a handful of businesses and I just work at this point with four at a time at any given point. And it's a really rewarding job. It's a really, really rewarding thing to see these businesses scale and to see these professionals, these CEOs become professional CEOs and solve these big changes that are life changing changes for them. They go from having a good business where they're gonna make a lot of money to being able to make a life changing money and really make massive impacts through their businesses to the world is a huge, huge thing for me.
A.J. Lawrence:
Well, one of the things you and I have discussed and I was reading through some of the things what I found really interesting was I've been, you know, I realized after I sold I probably should have had an EOS. EOS was kind of around back in, you know, the naughts and early teens or early 2010s scaling up. And then there's always a startup culture of OKRs that came out of Google. I think there's always that kind of ongoing discussion. Well this, it works in this, it works in that. It's better than nothing because you have the cadence. So what I found interesting was, having had that and having you know, 5,000 Starwars versus StarTrek arguments with other entrepreneurs around us Scaling Up and OKRs, you've created your own blended. And you even then will go further and you kind of blend it on the situation you're working with the person. How did that come about and how do you kind of look to blend different elements of these structures and processes to fit the entrepreneur?
Jason Long:
You hit on something really important. It was a mistake that I made early on. I thought that everybody needed to operate in a particular way. And what I realized is that you have to meet your client where they are. And sometimes clients don't have any goal systems in place and sometimes that's okay. You know, like in some cases they got bigger fish to fry. There's other problems and that needs to be done a little bit later. In some cases they have, in other cases they've got a goal system in place. Like they've got traction in place and it's starting to fall apart. Their company is scaled beyond a point where it's really, really working or it's the kind of business it doesn't work as well. And so one, the lesson was meet the clients where they are and implement what they need at that time. And then as they're scaling, then you can implement other systems over time. Not everybody needs this super robust forecast. Not everybody needs a super robust goal system. Not everybody needs all of these things. Sometimes they just need a marketing solution, sometimes they just need a sales solution and then we can work on the next thing. And so what I found though is that at a certain scale, I think traction starts to break down a little bit. It becomes not quite as useful. It's really useful if you're like 2 to 10 people, fantastic system. If you're 50 to 100, it starts getting hard. If you're 100 plus, it starts getting real hard. And so, and one of the other major things is that the way that traction works is like everybody has a KPI that they're measuring every single, every single week, right? And they're meeting on it every single week. That is really useful if everything is really well organized on the rocks. But in a lot of cases, as it begins to scale, those rocks start to kind of fall apart a little bit or it doesn't align as well as it should. It just becomes such a big task to get everything to align properly. And I find that implementing sometimes just layering OKRs on top of a KPI system is completely fine. Because as the CEO at the CEO level, at C suite level, you need to very clearly see how every single initiative in the entire business is laser focusing to the top, most important thing or things that you're doing. And through the KPIs and goals through the traction system. I have a lot more trouble with that than just doing it through the OKR system. But the VTO system, the Vision Traction Organizer for traction, and the process of getting to the VTO, like the entire meeting system of getting that set up, I think is what needs to be laid as an underlying foundation for the business. So I like to implement the VTO to get everything set and we know where the business is going, what it's going to look like. I do have a few little flavors and changes on that like they do 1 year, 3 years, 10 years on the goals. I like to do 1, 3, 6, 9. So it's just an every 3 year chunk. I think it's a little easier to do that. There's a lot of other little things like that as well. But I like the VTO on the bottom and then instead of KPI's traction, OKRs on top of it.
A.J. Lawrence:
No, I like that because you were talking about earlier being handed budget, your rocks in a sense. The bigger it is, without the careful feeding and training of your team, further down you go, getting the rocks to kind of start lining up for everyone that's involved gets harder and harder. It can be done, but you are spending that much more time feeding it where an OKR system is a little bit more straightforward. And you're still getting the leading indicator, you're getting that forward motion to move that much faster, you're still getting that benefit. Maybe not as hard, but you're not giving up a lot of overhead to get that. So I like that process. That is really kind of smart.
Jason Long:
The other part is that the on track, off track for every one of those initiatives throughout the entire process. So like in the rock system, like you're working towards them. But I really like having every single metric lined up in a spreadsheet where I can see it with the OKR system and being able to say like every single item, what's on track, what's off track. And I don't let people say like it's in danger. It's either you're doing it or you're not doing it or it's done. There's no in between on that. So it's real, crystal clear as to how things are looking in that system. The other thing that's really important though, that I think is a major failing of both of those systems, is actually the number one failing of both traction and measure what matters. I think it's implied in measure what matters, but it's not clearly stated is that these things have to relate to your forecast, they have to relate to your budget. You have to say if I set a rock or I set a goal, what is the financial measure of that goal? So as a CEO, I need to say like these are my assumptions for this quarter. Each one of these things is going to. I'm going to spend this much money, I'm going to do this thing and it's going to have this kind of impact and I need to see what that impact is in my forecast and in my actuals. And I need to look every single month and do a retrospective on, these were the things that ended this month, this is what we should be seeing that I forecast, we should be seeing from this. This is actually where we are at, and what is the variance and how much is the variance and how do I need to change things. How do I need to have that feedback loop to understand what's happening? Without the feedback loop you're lost as a C-suite, you're lost as a CEO. You have to be held accountable to the financial, the finances of the business and see the feedback loop. So formally you have to make the assumptions and state how much money are we going to make, how much are we going to lose based on XYZ things. And that has to be reflected in the goals as well.
A.J. Lawrence:
And it's really kind of interesting because I'm looking back at my experience where I was saying earlier I always found my month to month was never accurate but my annually until it wasn't. That kind of logic thing. In a sense the most important thing is that variance, the VIC. It is why is there wobbliness understanding that then? Because most everything in business is not failure of incremental, it's failure to handle X objects. Things that just come out of nowhere, things you didn't plan on. And if you don't understand your variance then you don't understand the incremental changes you can bring to bear when something turns against you. And being in that position, that is really interesting. And just kind of in thinking back, I mean how I failed. Oh I recovered similar to you. Yeah 35 to 5 going to from a really one of the great offices in Dumbo, New York, sweeping views of the bridges and the river to like a little office park, you know in the back corner. And losing half of the people who I thought I had “saved” because it was like no way are we working this and then regrowing it before selling. But that it's that very much that like oh the variance is the real, the real learning opportunity is that variance. And by focusing on understanding what that is and creating systems, because most of the time you're just trying to move forward. Fire, fire, fire, fire. I gotta hit a number, gotta do this. How many people do I gotta bug? Not the, Oh, what can I learn by how many people I reached out to that this happened? Or how do I build the team and how come the team is uneven in their execution of why you know all those things that then later on.
Jason Long:
That's actually one of the really important points. There are two other pieces on this as far as the variances are concerned. One, when you have a board, especially like a voting board that can vote you out, that can whatever, you know, no confidence in you, all of that, super important to be on top of those things because you're you have a boss, but the other boss that you have is your team. And obviously some people think that's more or less important. But if you have a bonus structure in place, which I think for the most part is a really, really important piece of business, if your variances are off too much, you're not going to be able to fulfill those bonuses. And you want your team to get those bonuses, you want them incentivized, you want them pushing forward, you want them to see this stuff. And your decisions as a CEO directly relate to every single person in the entire business's ability to get those bonuses. And so being on track with your variances and really, really putting in a lot of time upfront front into the strategy and thought and work that it goes into building your budgets and building the one year and the multi year planning for the business and really thinking out like every single campaign, what are we going to do, every release, every single item, what's the effect of that? That set of work is the thing that most CEOs not operating at that higher level, these smaller business CEOs moving up to that level, they don't understand how much time they should spend on strategy and working through all those things. Because that, especially in like Q4, that's the majority of your work every day you're working on what's your next year budget, what are all the things you're going to be doing, what are all the product releases, what are the service changes, what does next year look like? What is your bonus pool going to look like? Who are you going to bring on? What is next year's org chart going to like by the end of next year? What is your org chart going to look like? Where's your growth going? Obviously you should be thinking three years, six years, nine years out as well. But you got to figure all that stuff out in Q4 ahead of being ready to present a budget the first business day of the new year and have the whole team, hands on meeting about what does that look like? And this is actually one of the big differences I see between let's call them big time CEOs and small CEOs is that small CEOs are looking at what's right in front of them. What does this month look like? What does next month look like? What does this quarter look like? When I was doing that talk that I was telling you about that I got all my coaching clients, one of the things I had I said, everybody ratio. How many people here have a one year plan where you've thought out every one of your marketing campaigns, every one of your growth campaigns? I think I had, out of 500 CEOs I had maybe less than 2% raise their hand and say like, yeah, I've got a plan for that. Everybody else, these are for the most part smaller level CEOs. The guys that raise their hand are running big businesses. I was like, how much? You know, six month plan. How many? Three month plan. A lot of people said 50%. Three months, one month. Everybody's up, right? Most people are up. That's one of the big differences. You got to really, really put the time and energy in to think about that stuff.
A.J. Lawrence:
I want to go on and on and on, but we are kind of pushing this now. Jason, what's the best way someone can find out more information about you? Where should they go?
Jason Long:
Jasonmlong.me. That's jasonmlong.me. Yep, you get me there. You can also get me at tangentsolutions.net or jhmediagroup.com or Ascendance, sorry, my coaching company, Ascendance.coach.
A.J. Lawrence:
And I think we as entrepreneurs get caught in, you know, I always call it the rubbing the sticks together. But as you said, that kind of lowercase ceo because it's cool. And it's like, wow, this is better than working for the man. And we do this, the ego comes in, as you kind of call. Yeah, because I thought I was hot sh!t. We're fragile in that state. And you know, into your experience, we can be very, very fragile. But with the right work and the right effort and the right focus over time we can work on that and we can be less fragile, at least in our environment. We still are human beings. So that part we can't quite yet get rid of yet. You know, give it another a little bit more time. We'll be all uploaded. Your own experiences, to kind of wrap it up, into the private equity to now this coaching because yeah, finding your ability to understand what's driving your business and understanding in a way that creates a common language between multiple pieces. Because at the end of the day that’s what we do. And if you're not using the math, the maths if you're from Europe, then yeah, you're kind of creating stories from scratch each time. Yet with the math, with the budget, within the structure, within the strategic framework, and then sort of the cadences and then the type of reporting effort and the sharing of data and the tracking of data amongst different people in the identification, you layer these things on in a way that really drives value. I'm looking at this all in hindsight, like, wow, that would have been great. That would have been amazing. So, no, thank you so much for sharing this. And look, love to keep talking with you. Love to find more things to kind of discuss. And I hope, as you know, as you see what I'm doing with my efforts here, and hopefully I'll be able to share, but I'm keeping it very slow as I move forward here. But, Jason, this has been a lot to think of. So thank you so much for coming on the show today.
Jason Long:
Yeah, absolutely. Absolutely. Thank you so much for having me.
A.J. Lawrence:
My pleasure. This is all for me. Mine, mine, mine. Now, everyone, thank you so much for listening to this episode today. Please go check out Jason's material. There's so much to share. He has some really great information to look at. Your own business, take it into your perspective of what you're working on, because I know just from reading his material, I had been thinking about it and being introduced and then speaking of Jason, whole another level of way of thinking of what I'm trying to work on. So please, if you're in the position, reach out to him, talk to him about what you're doing with your business and sort of how he goes about helping people like you. And maybe you learn and maybe you find a really great path. So, everyone, thank you again for listening. Can't wait to be back. Talk to you again soon. Bye-bye.