Noob School - From West Point to Private Equity with Jake Bennett of Well Street Partners

Episode Date: October 18, 2025

In this episode of Noob School, we sit down with Jake Bennett (via Zoom), cofounder and Principal of Well Street Partners. You can find him on LinkedIn here: linkedin.com/in/jake-bennett314 Jake is a Virginia native whose journey spans systems engineering at West Point, five years of active duty in the U.S. Army (with assignments in Colorado, Oklahoma, and Afghanistan), and an MBA from Michigan Ross. After his service, he joined McKinsey’s Chicago office—leading operational transformations for lower/middle-market industrial firms and executing procurement strategies across industries. Today, Jake and his cofounder are focused on acquiring, operating, and growing small and mid-market businesses through Well Street Partners. In this episode, we dig into: How his systems engineering and military background shaped his leadership and operational mindset What he learned at McKinsey and how that informs his approach to transformation and execution The “what, why, and how” behind Well Street Partners – investment criteria, operations playbooks, and value creation Sales, execution, and building credibility in small / middle market businesses Career transitions: how to lean into your strengths, navigate uncertainty, and build upward momentum Whether you’re early in your career or plotting your next pivot, Jake offers a compelling blueprint at the intersection of operations, strategy, and mission-driven investing. Get your sales in rhythm with The Sterling Method: https://SterlingSales.co I'm going to be sharing my secrets on all my social channels, but if you want them all at your fingertips, start with my book, Sales for Noobs: https://amzn.to/3tiaxsL Subscribe to our newsletter today: https://bit.ly/3Ned5kL #SalesTraining #B2BSales #SalesExcellence #SalesStrategy #BusinessGrowth #SalesLeadership #SalesSuccess #SalesCoaching #SalesSkills #SalesInnovation #SalesTips #SalesPerformance #SalesTransformation #SalesTeamDevelopment #SalesMotivation #SalesEnablement #SalesGoals #SalesExpertise #SalesInsights #SalesTrends#salestrends

New School All right, welcome back to Noob School episode 154. Can you believe it? Today I've got a relatively new friend, but a friend nonetheless, Jake Bennett. Jake, I met him at my daughter, Lizzie, and son-in-law Mike's wedding, which would have been how long ago? Jake, do you remember? Is that 2019? 19, 19. that's about yeah six years so six or seven years ago but we we met at the wedding and gosh there was

you know hundreds of people there but we managed to get a good conversation or two in and uh really like jake and uh as i've gotten to know him more um understanding how he's becoming you know what he's what he's becoming which is pretty pretty darn impressive um currently um i say you're 31? How old am I? 33. You look younger. 33. But you've already, I don't know what you did in high school. I'm guessing high school. Did you do like, were you a really good athlete in high school? Yeah, in high school is kind of a walking stereotype, football, baseball, you know. All the sports? Yeah. And then you went to West Point. Yes. And did you play any sports there or just? just surviving is a sport. Surviving is definitely a sport, but also played team handball there. So not quite, Division I sport, not quite intramurals, but club levels. So in the middle, and we joke, it's all the people that, you know, all the washed up football, basketball, baseball players end up on team handball squad.

Yeah, well, cool, cool. Yeah, well, that's a, yeah, that's a place where you've got to be in tip-top shape, whether you're on playing the sports or not. But you went there, you became an Army officer. You served five years, right? That's right. Five years, okay. And along the way, you got a Bronze Star. And we looked it up because none of us were in the Army,

but we looked it up before us. It's like meritorious service in battle. Is that what that is? Meritorious service, no valor associated with it, so it didn't do anything heroic to earn it. just, you know, did right by my team and the folks I worked around. You did this for giving doing a good job. Yeah.

Okay. Well, still, you're probably underplaying it. And a bronze star sounds pretty good. A lot of hard work. But, yeah, it was part of a good team. So, so I think one of the questions is, where did you, where are you from to begin with? Yeah, so born in Houston, Texas, but did most of my grown up in Virginia. Both of my folks worked for Exxon and then Exxon Mobile.

So I was in Houston when it was Exxon. Then the merger happened and we moved up to northern Virginia. I always have to be careful how I answer that question because if you say you're from Virginia, folks from Southern Virginia will say, oh, well, you're from Northern Virginia. And if you say you're from the D.C. area, then the D.C. natives will come after you for that. So, so, yeah. Okay. That's very, okay. I got it. And why did you decide to go to West Point?

I don't know if I have an inspirational answer to that question. I think at the time, you know, being 16, 17 years old, realized that I was motivated by things in a different way than my peers and felt like going to West Point would be a way to kind of double down on my strengths. People always told me I was a natural leader, still not sure what that means. And then also, like we talked about, you know, was the walking stereotype, big into football, baseball, a few other sports.

In West Point seemed like a place where I could cultivate that leadership side of things, while also, you know, kind of exiting my comfort zone and doing something very interesting in my place. Yeah, something difficult. Yeah. Difficult. And doesn't everyone have to, like, being engineered, do you have to take a lot of engineering courses to go to West Point? Yeah. And so I think for that, I never really stood a chance.

Both my parents have engineering degrees with their oil and gas background. So majored in systems engineering, which was kind of like a jack of all trades type type engineering. Yeah. I guess they don't want people like majoring in poetry and then becoming an army officer. Yeah. So I think like even if you major in like humanities like English or something like that, you're still getting ambassadors in science.

So it's like the only like philosophy majors in the world that are still taking like intensive math and science classes along with their philosophy classes. That's pretty funny. Yeah. So you got out and did you go right to business school at Michigan? Yeah. Yeah. So as I was thinking about getting out of the Army, did kind of what I typically do,

talk to people who had done it, you know, two, three years ahead of me. Heard about this consulting thing and felt like it was a good mix of what I liked in the Army, getting to solve problems, work on teams, but in kind of more of a corporate setting. figured the best way to get my foot in the door and to make sure that I was as prepared as I could be on that first day of consulting work. Business school was the way to go. So, yeah, with the business school route. And then how did you pick Michigan? Why did you go there for business school versus somewhere else? Yeah, so like a lot of other vets who were transitioning, initially started doing kind of looking at the list of MBA rankings and just going down the list and saying, hey, I'll apply to these. But early on in my time, visited Ann Arbor, got to go.

go to University of Michigan for a Saturday football game and just, like, fell in love with the student body, the environment. And it helps that one of the guys that I worked with in the Army, we, you know, deployed to Afghanistan together was like a year ahead of me. So when I visited him, he was in his first year. And then ended up living with him and a few other guys during my first year, their second year. So I think, you know, going from Army into business school was kind of an intimidating proposition. But feeling like even before I was even a student there, I had like some family there, definitely helped much to be there. Yeah. Interesting.

I think that's an interesting point to dwell on for just a minute is, you know, you're going from West Point to being an Army officer to like, what am I going to do next? And you said, I'm talking to, I presume, other Army officers that were a couple years ahead of you that had gotten out a few years ahead of you. What's the landscape looked like? what are some good choices. Is that, is that what happened? Yeah, that's exactly right. I think, you know, you can read all the blogs in the world, watch YouTube videos, read books and things like that, but nothing beats the human experience. And, you know, some of those vets for ones I knew personally. And some were folks that I just kind of randomly reached out to and they saw that I

was also a bet. And so they're willing to talk. And so we get into like how, how Sean and I transitioned into this thing took a very similar process of talking to folks and hearing about their experience. Yeah. Well, that's kind of how we got back together as you just reached out to me as another, you know, a person who has been buying businesses, you know, for a while that, you know, we could talk and discuss things and, you know, it's just a smart thing to do is to find other people that they've already done it, pick their brain and didn't make your decision. Yeah, and I think, you know, nowadays there's so much, so much over email and text. Nothing beats the the face-to-face. I know we met on Zoom, but that's kind of the next best thing with the best thing

being, you know, face-to-face with a coffee or a beer in hand. Yeah, I agree. Good experience business school and probably, you know, if you're looking at top 10 business schools, there's probably not one of them you had gone to you wouldn't have enjoyed, you know? I think so, but, you know, having a big-time football program there definitely doesn't hurt. Well, that's a good point. I guess if you go to Duke, you know, what are you going to do on Saturday? You know, you're not going to go to a football game. You've got to be careful. I got a Duke grad sitting behind me right now.

Well, but he didn't go to a football game. He went to a basketball game. He was probably one of those Cameron crazies. Almost certainly. I think I've seen you with your shirt off. No, but, you know, for a lot of, like, top cases of schools, they're in, you know, a big city. So say if it's in New York, a large portion of the student body kind of lived in New York before, they're going to live in New York after. And because of that, they don't really make as much of an effort to branch out and meet folks.

But whereas at Michigan, you know, very few folks are from Ann Arbor or like, you know, southeast Michigan area. So for lack of a better word, you kind of have a captive audience. And with that, you kind of are forced to hang out with each other, which leads to making it sound so negative. But it leads to like truly like authentic friendships and bonds just because you're around these folks all the time. And then, you know, the football game's obviously a huge amount of fun. But having the entire student body, not just the business. school rally around, you know, one event and in one team, a couple Saturdays in the fall is a pretty powerful thing.

Yeah. You ever heard the name Bo Schembeckler? Oh, I've heard of them. Well, a long time ago, he was the legendary coach there. I always thought that was one of the best football coach names in the business. Absolutely. Absolutely. Yeah.

I mean, it was born to be a football coach. But we were there for the Harbaugh era kind of during the dark days before he turned it around and we started beating up on that school down in Ohio. Yeah, those rascals. Yeah. Well, that's good. So good experience there. And then, so now you've gone from West Point, you know, one of the, probably the greatest

leadership training grounds in the world to a top 10 business school, to McKenzie. And McKenzie is, you know, it's, I think it's still the best large. global consulting firm for business out there. Is that correct? They would tell you so. And I tend to agree. That's what the advertisement said. Yeah, I would agree. Yeah. So it's funny, sometimes when you get to be that good, the only press that gets out there is bad. You know, people just want to, they want to bring you down because you always hear these stories about things didn't work here or didn't work there. But I'm sure it works a lot, you know, or people wouldn't keep using them.

Yeah, and that's the joy of using consultants. When things go well, the executives that the client company can take the credit. If it doesn't go well, the consulting. McKinsey did it. Yeah, yeah, that's great. So you obviously decided you wanted to work for a large consulting company. I would think to learn, to continue to learn, you know, how things work. Was that the idea?

Yeah, absolutely. Coming out of business school, this entrepreneur, route was something that obviously interested me. Kind of felt like I wasn't ready for it. Obviously, business school gives you a lot of those skills and knowledge that you would need, but it's all in this kind of, you know, sterile academic environment where everything's perfect. So the thought of doing, you know, applying some of those skills that I learned in a, like a full contact environment where it's, you know, you're briefing real people, like the data's messy, you're having to navigate, you know, egos and opinions and things like that was a

was appealing to me. So they say that, you know, MBA is obviously your master's in business, but consulting is kind of like you're getting your Ph.D. And so getting a job at McKinsey is not easy. How did that process go? Yeah. So a good thing about going to school like Michigan is that the consulting recruiting process is very, very well structured. It's one of those schools where the firms come to you. So during the first semester of your first year, McKenzie, BCG, Bain, Deloitte, EY, like everyone, comes to campus. And it's kind of a two-way recruiting process where, where obviously you're a student trying to get hired by them,

but it's also an opportunity for them to get to know you. So during that fall, it's kind of like a bit like dating, right, where you're trying to feel out, you know, what they value. And if you think you'd be a good fit there, while they're trying to figure out if, you know, you would be a good fit for what they have going there. So kind of, you know, interviewed with all the different consulting firms, actually did my summer internship at another consulting firm because got the ax from McKinsey

during that between your first and second year internship. But made a good relationship with the veteran recruiter from McKinsey. He was like, hey, like, I think you belong here, like give it another shot next year. So, so came back in the fall. A lot of my peers were, you know, celebrating having their full-time offers and, you know, hanging out and partying, have a good time. While I was, you know, doing interview prep and doing math drills and, you know, doing all that fun stuff, but ended up working out and was able to get my foot in the door. Well, let me ask you this, because it looks like, I mean, I don't take this a wrong way, but I mean, your path has been so pure so far, you know, I'm sure you did very well in high school

and then West Point and then Bronstar, business school, and all of a sudden they cut you at McKenzie. Yeah. How did that feel and what does you do about it? Yeah. I mean, I think overcoming that is, you know, obviously the first, you know, 24 to 48, it's stung quite a bit. You know, you want it badly. I made it right to the final rounds and got cut. I would say like, you know, as you say it, it seems like my resume up to that point was

flawless. But, you know, I definitely dealt with failure along the way as well. Whether it's, you know, setbacks in the Army, not getting the assignment I wanted, or, you know, obviously West Point is a high intensity environment where there's lots of opportunities to make failures big and small. So I feel like I had gotten some reps on failure at the the time. Yeah. And I think always try to use those failures as a way to just kind of bounce back stronger. Um, so coming out of like the, you know, spent 24 to 48 just kind of, you know, a little angry, a little upset of, of coming so close but not getting it. Um, but I think after after that time period, I spent some time reflecting on what I was still missing. And I think where landed was,

you know, was still at that point, you know, six, seven months out of the army really, like still very raw in kind of the way I spoke, the way I solved problems, things like that. So I felt like there were still some areas that I could improve. And it was also pretty encouraged that, you know, despite how raw I was, I still made it, you know, pretty damn close to hitting the goal. So gave me some kind of focused areas to improve on during, during that summer until like the following fall. And I think I'm better for it. Well, that's an excellent point. Excellent point. I think it's worth talking about just for a moment. But, you know, to, you know, of course, we're a little bit upset at first when something happens.

We don't want to happen. But then to say, what can I learn from this? Why did this happen? And probably these people aren't doing it just to get me. You know, I mean, they have a reason. And maybe it's because I'm too military right now. You know, I'm still, you know, still kind of, you know, look military person versus. as a consultant.

And that's a very grown-up thing. The other thing I'll say, I've thought about writing a book on this, but I can't tell you how many people have suffered some type of, you know, what we would think is just a terrible setback and who have turned that into

something completely different, which is ten times better than the direction they were going. 100%. Yeah. 100%. As long as you just keep, like keep the attitude and keep moving north,

But if you stop and dwell on the rest of your life, then you're done. It did defeat you. Yeah, exactly. I wouldn't expect that from you at all. But I'm glad you saw that maybe that was it. You were too close to the Army. You needed some time. Yeah.

Yeah, and I was also fortunate to have, you know, good people around me. Obviously, my parents are always a good support system that helped me, you know, get, they provided some context around, like, that specific failure. Yeah. And also even, like, the final round interviewer that I worked with, gave me the call saying, hey, like, you didn't get it. It was like a very, very cool, like, down-to-earth guy in, like, typical McKinsey fashion. He's like, here are the three things that you need to do if you're going to come back next year and, like, reapply. He gave you a PowerPoint?

No, no PowerPoint. Just, you know, here are the three big things, you know. Oh, geez. Well, so you didn't get it then, but you stayed after it and you eventually got it, and you stayed with McKenzie for how long? About three and a half years. So, yeah, kind of. You kind of of a like like I said got the PhD in business so you know they say the PhD in business thing the other thing they say is that your consulting is worth three years in an industry reason being it's you know high intensity you're kind of constantly changing mental gears switching between projects switching between industries and so you're constantly having to kind of scale up on on learning

things and being able to to walk into a room and tell people what's gonna happen so yeah yeah so first two years there was was an associate and then got promoted a manager. Those first two years, you're kind of focused on like the technical aspects of being a consultant, obviously, you know, Excel, using other, you know, quantitative tools to find answers and messy data. And then, you know, as you progress, they're putting you in front of clients more and it's more kind of storytelling and selling.

So how many engagements did you have? How many different businesses? Oh, man. Let's see. three and a half years, best guess, 10 to 12, kind of a mix of some of them were just kind of six-week diligences or kind of strategy sprints and some were longer-term implementation. So kind of a mixed bag there, but probably 10 or 12 across probably three or four different industries and I don't know how many functional areas.

And can you give us, you know, without giving anything away you can't talk about, what was the best success that you and your team had? best success that I had, we worked with a, like a polyethylene chemicals company. And we were looking at their procurement spent. So for the longest time, they kind of thought they had, you know, achieved maximum savings based off conversations they had with, you know, their vendors and kind of other folks like around the supply chain. And we came in there kind of at the, not because they wanted us there, because like their ownership group wanted us there. And And they're like, hey, like, help us find, like, we think there's value here.

Like, maybe there is, maybe there isn't. Like, get to the bottom of it. And since they were in a good spot to begin with, we had to get creative of where we could find value. But there was value there. So I would say proud of that work is a, like the number of dollars that we identified for them to save just through procurement savings was strong. But then, you know, we also did a good job of towing the line of working with the procurement managers who were kind of comfortable in the status quo. while also working with the ownership group that wanted things like changed very, very differently. I think, you know, I was, you know, a small part of that, but partners I worked with did a great job of kind of balancing all the different stakeholders.

And then us on the ground did a good job of kind of helping everyone understand what value is possible. Good. That's a good. That's a good one. I've got a friend, a good friend that I had worked with before. And he was trying to sell this company, this big, I think it were a fish company or something. like a million dollar project for to do something they really wanted to do, but they just didn't quite have the money. You know, they wanted to do it. They needed to do them money.

Well, he said, well, let me see if I can help you save some money. And he literally did a little mini procurement project for them and saved more than enough money to pay for this project. So. Yeah, the sticker shock on consulting engagements is always, is always very, very real. But then you look at the savings that they can often generate, and it's kind of like, man, we should have done this long time ago. Yeah, yeah, I agree.

Well, there's a reason people use them for sure. So you had a great experience at McKenzie, which again is another, you know, five-star piece of your resume. And you and your partner decided to start Wall Street partners, excuse me, to buy a business, a significant business that y'all would run. and build. Is that correct? Yeah, that's exactly right. You know, I think I recognize that whenever I was doing the best work and happiest in my career,

whether it's at the Army or with McKinsey, is when I was kind of having free reign and able to be entrepreneurial. Yeah. So, like, for example, in Afghanistan, when I was there back in 2016, which Holy Cow seems like a long time ago, there was a hard limit on the number of troops that were allowed to be in country at any given time. And so with that, the folks that were in country were spread very, very, very thin. So at the time, I was executive officer.

So basically second in command for a security task force company element. And my commander was like, hey, like, I have a million things to do. You have a million things to do. Like, just go figure it out and like, let me know if you need anything. And so with that, I was able to kind of operate how I wanted to when I wanted to and kind of prioritize things the way I saw fit and solve problems of which there were many. in whatever way it made the most sense. So really enjoyed that. But, you know, inevitably with the Army or with McKinsey, you're not going to be able to

operate, you know, with full, with full flexibility all the time, only in limited stretches. So I was looking for something that would allow me to kind of build upon the skill set that I had that I built in the Army and with McKinsey. But in that kind of entrepreneurial mindset where we can kind of do things their own way. Yeah. Well, heck, yeah. There's nothing like it. You know, there's nothing like it.

having your own business. Now, let's talk about that because one of the purposes of having you on the podcast is maybe someone who's watching might have a business that they want to sell that would be perfect for you. You know, we don't know. But why don't you tell us about what you're looking for in terms of the type of business and the size? Yeah, absolutely.

So we're a private acquisition firm. We're looking to make one acquisition. Ideally, a company that we would acquire would be owned by a retiring baby boomer who has built an awesome business and wants to be basically rewarded for said awesome business that they've built. Size-wise, we have some flexibility, generally speaking, about 6 to 30 million in revenue, maybe 2 to 6 million in EBITDA. Our sales pitch to them would be we're different than private equity. we can still reward you and help you sail off into the sunset in whichever way you want. But unlike private equity, we'll move ourselves and our families to wherever the business is and we'll personally run it.

So the idea is to reserve the name of the company, the team that's in place, and then that business owner's legacy and allow it to be kind of like our next chapter, our full focus, rather than just being one of many dots on the map. That's pretty good. keep the name, keep everything where it is, and then be very flexible with the owner. Some of them want to leave immediately. Some want to stay.

Some want to keep a piece. Some want to ghost options. I mean, who knows what they want. But it's good that you can offer that to them. Yeah, and like the flexibility you said it is another huge advantage. Some owners just want to, you know, buy their boat and literally sail off into the sunset. Yeah. Whereas some want to stay involved in the business.

and we've seen it shake out a bunch of different ways. Sometimes, like we spoke with a seller a few weeks ago who ran a trucking fleet and kind of, you know, wanted to take his foot off the gas, no pun intended, but he was still very, very interested in like the electric, the EV trucks that they were bringing into the fleet. And so one of the options we gave him was like, hey, like, let us run the trucking about start of the business. And, you know, we'll make you the guy that's in charge of electrifying the fleet and you can run the business. So, yeah, a lot of flexibility. Yeah, that's cool. And then in terms of, so geography doesn't matter, size does matter, six to 30-ish,

and then what about type of business? Yeah, so my background is in industrial services. Sean, my business partner's background is in healthcare. So I'd say we're looking for businesses kind of within those verticals that meet, you know, make it favorable for first-time CEOs. So So some of the characteristics there would be like high amount of recurring revenue, you know, primarily through like contracts, master services agreements, things like that. And low customer concentration so that, you know, if one customer walks out the door, your business doesn't fail. What do you think about these companies that do uniforms? Like pick them up, clean them. Yeah.

We love the linen service game. We love the laundry game. We're actually in the process of reaching out to a few companies. not that general, but a few kind of niches within, within some of those areas. We see a lot of value there. Yeah. Yeah, I always wonder about those. I see the trucks all over the place and I've never worked in a business that required those. But I bet you it's a bet you it's a good business. You mentioned the trucks driving by since we started looking at doing this a little over a year ago. We've now become freaks where wherever we're walking down the sidewalk and we see, you know, a logo

on the side of a work van or a truck or something like that be like oh like I wonder what they do like where they headquartered like I think we can figure out like what their revenue is so we've become like research Greeks like that every time a truck drives by it's unbelievable I mean like I don't know it's probably 20 years ago Jake I was at the at the driving range at the club it was like you know Wednesday afternoon or something and I I saw these older jet not older but old you know probably how old I am right now but like in their 60s or 70s and they're out there on Wednesday, getting ready to go play golf. And I asked the problem, like, tell me what these guys do.

And one of them owned a bunch of convenience stores. One of them made some type of industrial glue. You know, I can't remember what the other one did. But, I mean, it was things that we would never even, you know, there's no sign that says industrial glue, you know. They're out there somewhere doing something, but they got customers that pay them money every month and they can go to the club, play golf whenever they want to. Yeah, and it's like, you know, the industrial glue thing made me think, you know, as we started this too, where you end up doing deep dives into these like seemingly random, like little niches.

So one of the, like the best outcomes of folks that have done something similar to us was say like billboard maintenance company where like they would literally like mow the grass and like repair the light bulbs for like billboards around the country. And it's one of those things like intuitively like makes sense. Like I understand that they would be out there. but I don't ever think to like dig into their business model like this. Yeah, it's wonderful. That's a wonderful niche. It's probably very little competition on a global or national basis or something like that. Yeah, wow.

That's so much fun to talk about these things. You know, my acquisitions are all around, you know, older industrial software companies. And I tell those people, those owners, the same thing you tell them. Like, you know, I'm not a PE company. I'm a software guy, you know, however you want to work it, we'll work it, you know, let's just give you a way out and give me a way in and everyone will be happy. Absolutely. And it does not require me to move somewhere.

That I'm not able to do, but software is a little bit different. I mean, there are people don't have to move either. Everyone can work from home as far as I'm concerned. Yeah. Yeah, there was a guy, a friend of mine was looking years ago to buy a bandana company. They made a pile of bandanas right around here in Greenville and sold them to convenience stores. And you would think that's an overseas thing. But they kind of would change them.

Like maybe there's a Halloween bandana or something about a wrestler bandana or something. There were different little themes that people would buy, not just your standard colors. He did end up getting it. He did buy a cement company. okay you know like 20 trucks and you know and it was it was I think it was doing very well yeah and it's so fun talking to those folks like okay like why would you choose a bandana company and kind of hearing about how they think about things we could talk a lot of business owners and it's one of the best parts of all this is just kind of picking their brains of how they see things and

where they want to take things right yeah yeah one of my favorites was I met a lady who owned a company down in Gainesville, Georgia, and it was a gas detection meter company. They were a handheld. They looked like an iPhone that you'd wear, and it would beep or whatever if there was gas in the mine or in the shaft or wherever they were. And they crushed it. Yeah. Yeah, and those safety-driven compliance-driven businesses are awesome, where, you know,

your customers obviously have to prioritize it because a lot of times, like, lives depend on it. Yeah. And oftentimes, you know, it's outside of their specialties. They kind of can't do it in-house or maybe due to regulations. Like an outsider has to be the one doing the inspection. So we love kind of those safety-adjacent compliance-adjacent businesses for sure. Well, so I look at a lot of different sites like Flippa, Biz Buy, Sell, you know, some of those.

But I don't think I ever see one that's really big enough for you. They're typically smaller. and maybe that's because I have my parameters set for smaller. But where are you finding your opportunities? Yeah, so some of the bigger deals will hit, like those biz-by-sell type websites. But we primarily source our deals through a few different ways. So the first off is just proprietary outreach. So that's us literally reaching out to business owners, trying to get them on the phone,

educate them on kind of who we are, what we're trying to do, and get a feel for, you know, what their objectives are if they're even interested in selling. and if so, do they have the characteristics that would make sense for us? So that can take the form of us just emailing them. We've written letters, some of which get sent back to us. A lot of it is to pick up the phone and calling folks, kind of a lost art. And then just kind of going in person to wherever we think these folks are, so conferences and things like that.

So that's kind of one side of things. And the other side of things would be through brokers. So Biz Buy Sell is like a broker website, but there's, you know, ones of all kinds for all sides and all kind of niches that we work through as well. And so as part of that, a lot of it is just looking at, you know, their online postings and seeing if there's anything interesting us and reaching out of them. But a lot of it is relationship building. So that hopefully, you know, we work with a broker on a few deals that maybe don't work out. But then another similar one comes up and they're like, oh, you know, we should call Jake and Sean to see if they'd be interested in this.

And so we can, you know, get to a deal before it hits the broader market. Yeah, yeah. Yeah, part of it was just having your radar up, too. I mean, my father and his partner back in the day, you know, the partner was on a board at the church. It was like the church board or something. And the guy next to him said, hey, hey, Jake, you seem like a smart business guy. I want to sell my business. How do I do it?

And he says, let me take a look. And so they ended up buying that business and growing it into a real nice, nice business. So. Love that. Yeah. Getting out there and talking is a good thing. Do you have any of your bigger, your business brokers that specialize in tech sales? None that we're working with right now, but some definitely have that focus. Yeah, it seems like most of the brokers you work with either have like a geographical focus where they only focus on business in the southeast, for example, or an industry focus.

So, yeah, there's definitely some out there, but none that we've worked with directly. far. And roughly, we're talking about like service businesses, kind of, I would call them normal businesses. What kind of, how are you figuring rough pricing on, on those businesses these days? So it's typically just straight multiple. So whatever the EBIT is times, you know, an industry kind of standard figure to get to a sales price. Obviously a few things can play with that multiple. Size being probably the biggest one where, you know, like a small MonPas shop made, you know, be on the lower side, whereas a, you know, a regional, like someone who owns like an entire region for that niche is, would go a little bit higher there.

Yeah. The things that can impact that would be the amount of like contractual revenue versus one-time revenue and frankly, a laundry list of other features to get to that sale price. So a lot of it is just kind of like what the market is saying where, you know, if everyone else is buying, you know, that type of business for, you know, six X multiple, then that's, that's probably what this one will go for. but there's also some nuance and variation there. But yeah, that back and forth piece of it kills a lot of deals where, you know,

one side thinks it's worth, you know, some amount and the other side thinks something differently, and they can't get close enough to get a deal done. But, you know, again, that's where the flexibility in our model helps create common ground there, where sometimes those quantitative expectations don't quite line up. Yeah. I heard one buyer say that they were having success, getting the with the owner

to agree that if I can get $12 million out of this then we've got a deal and said okay let me work with you to get there let's see how we can get there

and maybe there's some deferred and maybe there's this and performance and whatever but if you don't have that number to begin with you know it's going to be hard We can help get to a place that that makes sense. Yeah, 100%.

And I think, you know, one thing we found in these early days is that transparency just saves everyone's time and helps you get to a better answer quicker and, you know, a better answer overall. Yeah, and like what you'll see drive up those valuations a lot of times is if the seller believes that there's like still a lot of growth to be done. And allowing them to, you know, roll equity is a good way to be like, okay, like if you believe it, like prove it. The upside is as much as you say.

We think we can take it even higher than that, then like this will be worth even more. If not, that's okay. Yeah. Yeah, that's an easy bet for you. I mean, if people think they can help you take it higher and anticipate to some degree in that, then that's great. Yeah, absolutely. Good.

Okay. All right. So I think we understand what you're looking for. with Wells Street. You're in Chicago, but you're ready to move. Yeah. So we're running our search out of Chicago. It's kind of the perfect place for us. You can fly direct pretty much anywhere. So no matter what business we're looking at, chances are once you get to O'Hare, you can fly directly there. So just relive in my consultant days of spending all the time in United Terminals. Yeah, yeah, I get it. Now, what if the new business is like in Key West? Will that be okay?

You know, that'd be tough. I'd have to convince my wife that we have to move to Key West. What a great place to raise a child. Yeah, yeah. Oh, man. All right. Let's talk about a few other kind of more basic questions. You've had a great career so far, and I think you're really just getting started.

But if somebody else is, let's say, getting out of college and they want to to go into business or sales, what advice would you give them? I would say two things. One is kind of like less inspirational. One's more inspirational. The less inspirational one is just our reading the news. As I was getting out of the Army, it's a piece of advice I got of, you know, just read the Wall Street Journal every morning. It's a great way to understand what's happening in the business world. And then when you are in those environments where you're surrounded by other, you know, corporate folks, it makes a little bit easier to talk the talk and understand the language that they make or that they use.

And then the second piece is figure out storytelling. Kind of everything that we've done up to this point is storytelling, whether it's, you know, while we're fundraising, you know, telling the story of, you know, how our partnership came to be and the story of, you know, our vision for the future. And then we're talking to business owners, the story telling them the story of kind of like who we are and why that story makes us fit to run their business. So kind of like, yeah, the less interesting piece of just read the news and,

get smart on that and then the, you know, like softer piece of work on storytelling. Yeah. So how would you say someone can work on storytelling? I would say, you know, first, you know, get out there. It's easier to tell stories if you have stories to tell. Yeah. And so if you're, you know, getting home every night and just, you know, on social media, you're probably, you know, not going to have too many interesting stories to tell. But if you're getting involved in your local community, going interesting trips, you know, live in life, you'll be better at it. That's good.

Yeah, we coach people the same way on the storytelling. We, you know, instead of, look, if I told you, hey, Jake, we want you to come to our money management firm because we're going to earn you, you know, we're going to earn you probably 11%. You're going to think, that sounds like BS, John. You sound like a sales guy. But if I said, Jake, I don't know if you can join us or not, but what we'd know. normally do is we work with people like Charlie and people like Mike. And, you know, we're getting there, you know, on average, and if we look over five or ten years, you know, heck, one of them double their

money from $400,000 to $800,000 over four years. So that's, I don't know what that comes out to, but we'd love to help you with something like that. Would that make any sense? So, you know, you're seeing it, Mike do it, and you're seeing it in dollars versus percent. And so, yeah, I'm not sure that's the best story in the world, but we like them to tell stories about other people. And it just sounds, it's just that people believe it a lot more than if I just say, here's a statistic. Yeah. Yeah. Yeah.

Good. Okay. And just go Army for a second. Give us one leadership principle that you learn from your Army training and being in the Army. I would say to be genuine. I think, you know, in the Army, a lot of people think that they have to act a certain way in order to be worthy of followership. But I think what I found is that the most authentic leaders are the most effective leaders are the ones who are the most genuine and the most authentic. My battalion commander when I was in Afghanistan, Neil Snyder, was like a very unassuming man.

He like had kind of like, he was kind of like a shorter guy, kind of like seemed like more of an academic. But then like you look at his background and he was like a true background. badass who was also like the smartest person in in any room that he was in. And so, you know, if someone like that walked into a room and tried to, you know, puff his chest out and be, you know, super, super intense, people probably wouldn't respond to it. But, you know, he relied on kind of his sense of humor and his just raw intelligence to inspire followership. And he was one of the best leaders I with because he knew what he was and leaned into it. And also didn't, didn't hurt that he was just like an overwhelmingly talented person who everyone wanted to be around and

follow. Yeah. Yeah. So that's kind of like a good example. And then you see folks who, you know, maybe watched one too many episodes of Band of Brothers or something who were just trying to be, you know, Captain America when they're very much not that. And soldiers, you know, in about 10 seconds, we'll understand, you know, what you really are and, like, not respect you as much if you're not being genuine to who you are. Yeah. And it's easier to be yourself. Totally. You know? Yeah.

It seems like a lot of work to try and put on a mask every day for sure. Right. Right. Yeah. Yeah. I've gone through phases like what I'll, like, I'm, myself is not someone who dresses real nice. I don't really like to look a certain way or dress or whatever. But I've gone through these little phases where I kind of get, I don't know, cocky or something and I'll dress a certain way. And it's just horrible.

You know, it's not, it's not the real John. And it's like peacocking, I guess. I don't know. Yeah. Yeah. Yeah. 100%. But I say be yourself and just, we're going to, we have no other choice. Let's just go with that. Who else am I supposed to be? That's right. I want to be like Jake, but I can't because you're Jake.

So what made you pursue the search fund model instead of doing a startup? So I think I mentioned that the entrepreneurial path was something that itched me for a long time. And to me, the search fund model was entrepreneurship with a path to profitability and maybe like some guardrails in place. So my business partner, Sean, worked kind of interned, like worked at a startup during business school. And for them, I'm sure I'm going to get the numbers wrong. But, you know, they raised, you know, hundreds of million dollars over the course of like five years and hit like $10,000 in revenue just like a few weeks ago. And so like that ramp is, you know, very stressful, very challenging and there's just so much unknown. Whereas, you know, in the search fund model, you're, you know, hopefully acquiring a business that's historically profitable, historically successful.

and you're someone who can step in and hopefully take it to new heights. So kind of like the risk roar profile that I was comfortable with. And it also allowed me to work with, you know, these small and medium-sized businesses that I think are just the best kind of people to work with. Well, I totally agree with you. I'm just completely in favor of, you know, finding a – learning how to run a business. You better learn how to do that first, which you've done in several ways.

but then, you know, picking, getting a business that you can operate is so much better than all these people at startup camp. I mean, so few of them end up with anything. They get some experience, I suppose, but I love the idea of trying to get into a business that you can handle. And it's just kind of ironic that you can sit there and tell me that it's, less risky to buy a business for $50 million than to do a startup on your credit card. Yeah, right. It's funny. And I agree with you.

It's less risky. But it's like, oh, my gosh, that's a lot of money. Yeah. Yeah. But we're, that's, I mean, you could buy, you might well buy one for 50, right? I mean, that's going to be in the, in the sweet spot if you're looking for a $30 million dollar business. Could be, yeah.

Could be. All right. I think we have a deal. So when you buy a business, do you already have like your 30-day plan? We have our 100-day plan. Hundreds-day plan. It's to sit back and listen. I think you hear about the biggest mistake a new Army lieutenant can make,

and it's pretty similar to the biggest mistake that a new CEO or president can make. And it's, you know, showing up on day one with all the answers and going and changing things. So, yeah, I mean, I think those first 100 days will be a lot of listening. and having our eyes and ears open and probably keeping our mouth shut. You know, hopefully opening our mouths when we're interviewing, you know, the middle management as well as some like key customers, but just trying to learn everything we can about the business to, you know, for our sake, you know, understand, you know, what exactly it is we bought and how we think

we can improve it, but also to kind of signal humility that, you know, we're not just going to come in here and kick doors down and break glass, but we're going to make a solution that or come up, you know, run initiatives that make sense, within kind of what the business is already doing. Yeah. Yeah. And, you know, also having a long-term view that you might run this thing for 40 years. Exactly.

What's the hurry? You know, let's take our time. So what advice would you give other veterans that want to start their own or buy a business or kind of get into business on their own? I would say just talk to as many people as you can. I know, like, sorry to go back to the well on that one. but talk to as many people as you can. I think, you know, on social media, particularly nowadays,

there's a lot of just like bad information about, you know, how easy this is. But I think if you get someone on the phone, they'll be transparent with you about kind of what's been good, what's been not so good, and what their actual experience has been like. So it's a great way to kind of learn the ins and outs of, you know, how to exactly do the thing while also giving you, you know, a few landmines that you can hopefully avoid while you do it yourself. Yeah. You're probably too young to remember, but a while back there was this thing where

the whole craze was about buying real estate with no money down. Yeah, yeah. And you could get cash back at closing. I mean, it was, I guess it was a different time then. The appraisers were a little different and the banks were a little different. But yeah. Yeah, but even now, like some of those voices on social media are telling you You can just, you know, knock on the door of a profitable, small business. Yeah. Pinky promise that you'll pay them with, you know, the next 10 years' earnings. And they'll be like, great, let's do it.

Take my business. But a little more to it than that. Yeah, there is. There is. But I do think it's, you know, I think one thing that helps, like when you are going to buy a business from somebody, the fact that you went to West Point and served the country and worked at McKenzie. And, you know, they're going to say, well, this is. is a significant, this is a real deal here. I can talk to this person. This is not some jackleg,

you know, that hadn't done anything yet or, you know, didn't go to business school, hadn't run a business. So I think, you know, but going back to our original premise of the conversation, you know, you've prepared yourself for this moment. And, you know, when I was in my early 20s, I asked my dad, who was a venture capitalist, I said, how, what's the secret for these people that I've met, you know, your friends over the years that have all become extremely successful. And he gave me a letter. He gave me a letter of like it was 10 people. And all of them, all of them had the same characteristic. They all learned business and particularly something about the business that they were in, whether it was the lumber business or finance business

or whatever, but they learned it, made their contacts. And when they were about 30 or early 30, they made their move. And they got a piece of the action. They bought a business. They started the business, whatever. And then worked like hell for 20 or 25 years, right? And so then they're 55 and all of a sudden says, oh, my Lord, Jake's a millionaire. I want to be like Jake.

Well, this has been a long-term plan. You know, it didn't you start when Jake was 52, you know? I mean, you started it when you went to West Point. So I see it coming, Jake. If I could buy stock into you, I would. Thank you. Thank you. But one thing I will say is that, you know, you make it seem like I have this, this is awesome background. I have the privilege to do a couple of good things. But I would say that, you know, some of those, like, pieces of my background look very, very good when talking with, you know, at the NBA crowd or with investors. But for a lot of small business owners, it's almost like a bad thing, right? Where, you know, having like a big brand name of like McKinsey or like having gone to business school, sometimes that can kind of cut the other way. And we're like, oh, you know, like, you think you know everything about my business, but you've never, like, got in your hands dirty.

Things like that. Yeah. So we've had to be careful of, you know, what parts of our background we highlight when having these conversations. Yeah. Obviously, with, you know, with the investor crowd, it's, you know, we're playing up our backgrounds in consulting and business school. But when talking with business owners, it's more about kind of like, you know, who we are as

people, you know, what our families value. And, you know, the military service is, is helpful there sometimes. Yeah. Yeah, I agree. I agree. Well, to me, all those things are very cool, but everyone's not me for sure. But that's a good point. Okay, just a few more questions.

Sure. These are really important. What is your favorite book? My favorite book is Catch 22. So it's, you know, maybe that's like a basic answer, but read it right around the time I got back from Afghanistan. And I think it's been my favorite book ever since. It's, you know, World War II, you know, Army Air Corps pilots. So it takes place during a war, but it's also a very funny, very absurd book.

And so for me, when dealing with, you know, tough times, I found that going at those tough times with a sense of humor and understanding the absurdity of everything. Yeah. Always makes those times a little easier. That's good. Okay. Favorite movie? Favorite movie? That's a tough one.

I don't know if I have like a one favorite movie. You give me more than one? I love The Matrix because I'm a huge nerd and it's one of those movies with great action that also is kind of makes you think. I love Super Bad because it's like kind of a coming of age tale for like our generation where, you know, they're like very vulgar, um, laden experiences in that movie or similar to like my experiences in high school and other folks in my So I said those are two my favorites. Good. That's good.

And then favorite band? Favorite band. That's another one where it's hard to just pick one. So I'll just go red hot chili peppers. Okay. So you like Flea? Yeah, he's all right. Well, is there anything else you want to say or promote before we finish up?

I would say, even if you're not sure, if you think Sean would be a good fit to run your business, I would love to talk to you on the phone for five, 10 minutes, tell you a little bit more about our vision and how we can plug in to what you're doing. Similarly, if someone you know is approaching the retirement age and is built an awesome small business, we'll love to chat with them. If you want to learn more about us,

you can find us online, wellstreet partners.com. We're also on LinkedIn, and John, maybe I'll give you that info to drop in the podcast description. But we love talking to folks, even if you're still kind of kicking the tires on retirement. We'd love to chat. All right. Well, and I would encourage anyone who's even thinking about it in next couple of years to talk to Jake.

He's a great young man and he and his partner are going to do a good job with someone's business. Jake, thank you so much. He had to promise me to come down to Greenville and stay with us and hang out and we'll tell us some more stories. Absolutely. much for having me. Okay, thank you.