Boring Money

Jim Bologa is a CPA. He spent about ten years at Price Waterhouse and twelve more as a CFO, COO and CEO at public and private equity backed companies. In 2007 a private equity contact called him about a trade school they had just bought in Connecticut. He said he'd come on as a consultant while he looked at other things. Every day at the school he learned something he could use to fix something in his own house. He never left.

Porter and Chester Institute started in Hartford in 1946, training World War II veterans in mechanical drafting. Today it teaches electricians, HVAC techs, plumbers, welders, diesel and auto techs, practical nurses and respiratory therapists. Jim ran it, and YTI Career Institute in Pennsylvania, for close to two decades. Then he bought Porter and Chester. Here's how.

The hard part was the regulation. When a school that takes federal student aid changes owners, the Department of Education can require a letter of credit of 25% of the prior year's Title IV receipts, posted at closing. For Porter and Chester that meant another $12 to $15 million of dead money on top of the purchase price. So in July 2024 Jim bought a small one first, the College of Court Reporting in Valparaiso, Indiana. Then he used it as the platform to buy Porter and Chester. In his words, David bought David, and then David bought Goliath. It took about five years. Other operators are still trying to figure out how he did it.

Today it's 11 campuses, 350 to 400 employees and 2,000 to 3,000 students a year. Most programs run about a year and cost $25,000 to $35,000.

We break down:

My take: this is the path I'd tell an 18 year old to look at. Learn a trade in a year, go work for someone who built a business in it, and then decide if you want to build your own. Your worst case is you go back to work doing the trade you were trained for. That doesn't sound so bad. And it's the same lesson as Jim's own story. He didn't wake up one day and decide to buy a school. He spent almost 20 years inside the business until he could spot the opportunity.

Jake Berk is 31 and the president of Berk International, a second-and-third-generation family business in Boyertown, Pennsylvania that converts toilet paper, paper towels and dry wipes. His grandfather started it in the 1970s buying bales of reclaimed T-shirts; Jake's dad and three uncles cut them into 20-pound boxes of rags and rolled them up driveways on skateboards. They built that into a company, sold it in the late 90s, watched the buyer run it into the ground, took the machinery back and started over. Today it pays eight figures a year and ships to 15 countries.

Jake's dad is still the CEO. Jake is the president who has effectively run sales for ten years. For a long time they loosely talked about where the business was going and never actually said it. Then a consultant sat them down with ten questions, had them write their answers separately, and read them aloud. They were not on the same page. That exercise is the reason this conversation could happen.

We break down:

I grew up in a distribution business and bought it in 2012, and we stocked toilet paper too. Every time it grew I had less cash, which is why I ended up in air filters getting paid upfront. So my take for Jake: more sales is the easy part. Before you hire another rep, model what five times the revenue does to receivables, inventory, purchasing, customer service, lead times and the credit line. Cash, not demand, is what stops a distributor from growing. Nobody actually wants more sales. They want more money in their pocket, and those are not the same thing.

Jonathan Boyar runs Boyar Value Group, the firm his father Mark started in 1975 as a research service and grew into Boyar Asset Management in 1983. The idea has not changed in fifty years: ignore what Wall Street pays as a multiple of earnings and ask what an acquirer would pay for the whole business. If the stock trades at a big discount to that number, it is interesting. If not, you do not have to swing. Jonathan puts 70 to 80 percent of his own net worth into the same stocks he buys for clients, turns the portfolio over about 10 percent a year, and says most days he does nothing.

The best example is Madison Square Garden. When the Knicks and Rangers were sitting inside one company at an enterprise value that made no sense next to what the teams were worth, Boyar wrote a public letter to James Dolan asking him to split them apart. The company did, the press picked it up, and the position outperformed. Patience got rewarded faster than they expected.

We break down:

My take: I left finance for air filters because I wanted something unlikely to change. Jonathan stayed in finance and built the same thing: a process that does not care what is fashionable, a client base that buys into it, and the patience to do nothing most days. Most owners I meet who sell end up afraid of losing what they have. A business you control, throwing off cash, is the opposite of that. That is boring money.

Stanley Henry ran hotels for 12 years. Eleven jobs in twelve years, because he was the guy they sent in to fix the one that wasn't working. New Zealand, Australia, the UK, a stint in Japan. In his last year he was running a hotel in Melbourne that did more profit in one January than it had ever done in revenue in a January, and his boss still didn't think he should be on vacation. He turned to his wife and said it out loud: as long as I work for someone else, they're always going to want more.

Six months later he was back in New Zealand with no network and no brand. He had five or six coffee meetings a day for six months, posted about it on LinkedIn the whole time, and had no idea what the business was going to be. Then COVID locked the country down and everyone he'd met asked him to do for them what he'd been doing for himself. First client May 11, 2020. Seven people a year later. Fifteen staff writing LinkedIn posts for brokers and insurance guys for three years.

Then he hired a 22-year-old with 400,000 TikTok followers to figure out video, and The Attention Seeker went to 300,000 followers in three months, 700,000 in eighteen, then Instagram, YouTube, a podcast. Today it's about 1.5 million followers across platforms, built with no paid spend, which is the whole pitch: an organic agency that is itself one of the biggest brands on organic social. Clients came the same way his LinkedIn clients did. They watched, then they called.

Eighteen months ago the agency was 40 people. Today it's 15 and does more revenue. He replaced eleven project managers with an AI he named Kevin, a context brain on a server in the office that digests every meeting, email and document every six hours and then puts calendar invites in the humans' calendars telling them what to shoot. The editors are still human, because AI makes average and the algorithm only rewards great.

This one is a little different from the usual episode. Filterbuy hired Stanley's agency a few weeks ago. I've believed in organic social for a decade and spent real money failing at it, and my personal brand started two years ago because I decided I had to learn the game myself. So the second half of this conversation is the actual plan for how you make people under 50 care about an air filter company, and how a small boring business anywhere should start.

We break down:

The line I kept coming back to: you can't pay Facebook to distribute crap anymore. The platforms only show people what they'd choose to watch, so the question isn't how do I get my message in front of them. It's what would they want to watch, and how do I get my name next to it. That's the directive I gave my team, and it's why I hired someone who has done it for boring brands before.

Stanley told my head of growth he'd put his neck on the line if the show didn't work. I wish every vendor felt that way. We'll find out in three months.

Jay Peterson got out of Boston College in 1991 into no jobs, went home to Kankakee, Illinois, and sold industrial real estate for a broker who gave him the listing nobody wanted: a hundred acres next to a dynamite plant. Two years later some friends set him up as a Canteen distributor with one route truck and two vending machines. He and his wife Myra were the first two employees. They canceled their honeymoon to take on a Sears distribution center.

That vending company got to about $10 million. He sold it in 2001, kept the water and coffee routes, sold those in 2005, and then a fax came across his desk. Nestle Waters had bought every independent water company in the country to compete with Coke and Pepsi, figured out they only wanted the dense markets, and was selling off the rest. Jay bought the Evansville, Indiana routes, with a Toyota plant and an Alcoa can plant on the customer list, for $225,000 on $1.1 million of revenue. That's Mountain Glacier. He's run it for 20 years.

Today it's a $6 million co-packing plant putting out about 2 million five-gallon bottles a year. 40 truckloads a week, with a plant that can do 80. He went from 30,000 home-delivery customers down to 15 big ones. The sales are there. What's in the way is a robot.

He bought it at a trade show, waited two years for it to be built in Poland, and got it dropped on his floor last June with a two-week install in the contract. It took seven months. The suction cups couldn't hold 20% of his bottles. The layout meant he couldn't go back to hand loading without cutting his throughput in half. He ran the plant around the clock from June to October, put about a million dollars of his own money in, and his father-in-law named the robot Philip Bottles. This year Philip is the employee of the month, every month. The hole from last year is still there.

We break down:

The line I kept coming back to: if you're upside down on half the business, doubling it might just make you upside down by double. Jay wants to go from 40 loads to 80. I don't know if that's a good idea, and neither does he, because nobody has the numbers yet. Once they do, the next move will be obvious to him, to his bank, and to anybody he'd ask for money. Until then everybody is guessing.

Jay is 57. He's spent 33 years horse trading in and out of businesses, and what he wants now is one the Peterson family keeps for another 20. The water is fine. The plant is fine. Culligan wants it. What he has to get right is the boring part.

Ian Dahlberg got out of the Coast Guard and was trying to figure out what he was doing next. He picked up a security guard license on a whim while going to college on the GI Bill, and it got him hired at the Waldorf Astoria in 2012 as a security manager trainee. He says he's got more stories from that one year than from six years in the military. Seven incident reports a day was the average.

Then he did the thing I keep telling people to do. He went back to being a guard. Night shift, shipping container terminal, so he could learn the side of the business he'd been managing from above. He wrote the business plan for Dahlcore in the guard booth. He didn't know what a bill rate was. He couldn't read a P&L.

Six more years inside the industry after that. Branch manager at Securitas, a mobile unit for Chase Bank, then Brooklyn: 300 people and 10,000 guard hours a week. He brought in seven figures of business and his salary went up $5,000. Two employers after that, data centers and then Chelsea Market, six days a week and twelve-hour days. He started Dahlcore in April 2018 by calling cemeteries, because he was looking for somewhere the big companies weren't.

First year, $90,000. Second year, $670,000. Then COVID took him down to three clients and about $8,000 a week. This year he's projected a little over $4 million, on 7% margins.

He also told me he bid roughly $100 million of RFPs this year and won none of them.

We break down:

What transfers from Ian's story is the order he did it in. He used the military to get into something adjacent, worked inside the industry until he understood it, and only then went out on his own against the companies he used to work for. I don't think he makes it without that.

What he's up against now is a different problem. He can have a $10 million business he runs himself, or a $10 million business that runs without him, and only one of those is worth anything to the family he wants to hand it to. He's closer to the first one. That's normal. It's also the whole job from here.

Ron Butler spent eight years at one residential electrical company and didn't want to leave. He asked them to match a $100K offer he'd gotten elsewhere. They couldn't. He pitched them on starting a service department instead, four guys, he'd out-earn the whole shop. They didn't bite. So he took the other job.

Day one he walked into a branch running on chaos. Day two he called his CPA and asked whether $60 or $70K working for himself, after the tax treatment, would match the $100K. She said more than match. Day three he told them it wasn't a good fit and left. He had just bought a house and had no real savings behind him.

That was 18 months ago. Top Notch Electrical Services did $131K gross in its first year, $91K net, and he's at $185K over the last twelve months. All of it word of mouth. He has never spent a dollar on marketing. Nine contractor relationships, built by getting up at 7am, putting on a company shirt, sitting in a coffee shop, writing down 20 or 30 numbers and calling them.

He came in planning to hire his first full-time employee. I told him not to.

We break down:

Ron's slogan is "confidence is competence." He passed his master electrician exam first try, at 26, when the four masters he knows averaged five attempts between them. That trait is why the business works. It's also why he wants to do every job himself, and it's the thing that caps him at $200K if he doesn't let it go. He asked me for a realistic timeline to a million a year. I said twelve months. I don't think he expected the number to be that low.

Justin Campbell got fired from a management job at TGI Fridays, moved back home into the room down the hall from his grandmother, and started taking $50-a-day temp shifts. The job site was far enough that he slept in his car outside it rather than risk the morning drive. One evening a guy from the commercial floor care company next door knocked on his window and asked what he was doing out there. He offered him steady evening hours. That knock is the whole origin story.

Four years later Justin was the youngest director of operations that company had. Then an outside sales team came in, the tenured managers started getting cut, and he got fired again. He started Midland Floor Care off temp-work money, renting equipment from Home Depot one job at a time.

Fifteen years on he's at close to $450,000, 98% commercial, three full-time people plus temp labor he flexes by project. A buyer has already approached him. They want a $4 to $5 million company, so that conversation ended quickly. The gap between those two numbers is what we spent most of this episode on.

We break down:

Justin is also the first guest I've had who actually did the thing I keep telling young people to do: skip the debt, go work inside an industry, then start something in it. He just didn't do it on purpose. And the last thing I told him is the part most people skip. You keep looking for the next solution when the answer is in the doing. There's no magic bullet. Go make it work once.

JT McCord spent eight years as a software engineer outside Columbus, Ohio, making $150K a year and stashing 30% of it. COVID sent him fully remote, and he bought a couple of 3D printers for the basement with no intention of selling anything. Three years later he runs 105 machines out of the bottom floor of an old salon. First year: $50K. Second year: $400K. He's at $400K again halfway through 2026.

The part that got my attention is how he got the machines. One gaming grip listing on Etsy caught fire over Christmas. At the peak, 95% of his revenue came from that single product, and he financed 16 printers off it. Today that listing is less than a quarter of a percent of sales. The business that grew on top of it is the real story.

We break down:

JT asked me how to turn this into an exponential equation. He's a process guy who wrote the software to run a hundred printers without knowing what's on any of them. That's not what's missing. What's missing is the creative side and the distribution side, and those are two halves of the same problem.

Matt McCrink is 22. A year ago he graduated from Auburn and walked into his dad's business — a third-generation operation brokering custom plastic and rubber components for manufacturers. For two decades it had been doing about $50K a year in profit. Basically a side hustle. In the twelve months since Matt joined, revenue went from $380K to over $1 million.

I brought Matt to New York to understand how he did it, and to push him on what comes next — because when I asked him what he's actually building toward, he couldn't say the number out loud. We got there.

We break down:

Matt committed on camera: $2 million in revenue a year from now. We're having him back to check.