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HoldCo Stories: Jesse Tinsley
Winning the long game with the right people
Michael Girdley
January 11, 2025
In partnership with
Hey folks!
That’s right, we’re back with another HoldCo interview.
Today: Jesse Tinsley – who recently acquired Bench Accounting while on vacation and with no investor money.
Read on to discover his acquisition strategy, how he moves so quickly, and his thoughts on long-term business building.
Want the whole story — and the chance to schmooze with him personally? Jesse is a speaker at HoldCo Conference 2025! Grab your ticket today.
Let’s get into it!
What’s your origin story?
I grew up in Silicon Valley, and went to school with a bunch of tech folks who are really successful today. I started my first company in college.
Come the financial crisis I was a “forced entrepreneur”, as I like to call it — because I couldn’t get a job, and the market was terrible.
So I started a services company called Job Mobs doing recruiting and did that for a decade plus. My mother is in recruiting so I learned a lot growing up around it. And both my parents are entrepreneurs who ran their own small businesses for many, many years, so I learned a lot from them.
Then two years ago, we made a bunch of strategic acquisitions. And suddenly I had a recruiting & tech holdco.
I didn't even know what a holding company was until maybe six months to a year ago.
What was your company’s early journey?
I got lucky. I like to joke that my wife was my first angel investor. She had a high-paying tech job, and we started dating the same year I started my company.
So I got lucky as the broke entrepreneur, making a lot less than her at the time. And that helped bootstrap things quite a bit.
From 2012 to 2022, I really started to mentally shift the business to that holdco model. We saw that everyone in the recruiting market was playing defense, and we wanted to play offense.
We saved a bunch of cash, then went out and bought 9 companies in the last two years. We have another 3 or 4 pending right now.
The thinking is, you never want to sell. Private markets are quite liquid now, with so many options for debt and secondaries and sales, so you can keep employees and long-term stockholders happy.
So all those acquisitions were bootstrapped too?
Yeah, we're still self-funded on those. We use cash off our balance sheets, creative financing, burnout, seller’s notes, cash at close, rolled equity, a mix of different things.
I won't name names, but some other holdcos out there are leveraged really, really high with debt. And it meant the last two years, they couldn’t play offense.
So we’ve always been more conservative on that front. Even now our debt levels are very low compared to revenue.
When we use it, we pay it off very quickly. We’re pretty adept at printing cash from all our businesses, so the snowball effect is moving really fast right now.
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What changed in 2022 that you started acquiring?
During COVID there was so much opportunity in the medical space, and I completely missed it. So I was really hard on myself, and did some serious reflection.
And I landed on some core principles that I found really helpful. Basically looking for strategic inflection points in the market.
In May 2022, I spotted some market trends in revenue and jobs report data. And when everybody stopped buying companies, we were like, “Wow, why would we not buy companies at this price?”
It was stupidly good. You could buy at 1x. It doesn’t take a math major to figure that out.
We also made sure we were ready to move extremely quickly. That helps you win a lot of deals.
And we couldn’t do all these deals if not for our really good finance people and accountants and lawyers. We’re not spending hundreds of thousands or millions per transaction on it.
Everything was working in conjunction.
What’s your acquisition strategy?
Early on in my recruiting, I was helping some giant companies scale like Coinbase and 23andMe. So one thing I really understand is talent density and how to scale teams very acutely.
But part of our secret sauce has been point solution companies led by fundamental winners.
Then we focus on retaining those founders, and keeping them motivated and inspired to help us win together. What we say is, we need you all in for at least a year or two.
If they want to leave after that, we can hire a great operator. But our goal is to make rewards and incentives very strong where we might overpay for an acquisition, but it’ll be over four years.
Do you ever think about legacy?
I care about my legacy today. My wife, family, friends.
But in the bigger picture, there’s Vanderbilt, Rockefeller, Rothschild, maybe JP Morgan… but other than them how many founders still have a legacy 100 years later?
Even if I build a $100B company, it’s unlikely my legacy would live on more than one or two generations.
So it has no material impact to me. I don’t need people looking at me and seeing what I’m doing.
What matters to me is that my kids know I’m a good dad. I could care less if everyone forgets me as soon as I die.
If somebody is reading about me in college 50 years later, that’s cool, but it doesn’t impact my decisions at all.
What’s the internal motivator for you? Are you striving for something in particular?
It's funny. It's really easy to compare yourself to others in your journey, whether it’s athletics or academics or whatever. But I don't look at competitors. That’s both a strength and a weakness, but I don't really care who's doing what, right?
I think general happiness is just having some control over where I’m going. I don't have some abstract goal related to value or outcome.
We want to be a $100B+ company. We think we could create an ADP or Workday-type competitor in the future that has the same scale and scope globally, but with automation and AI where we have 500 employees instead of 100,000 like they do.
But I’m not motivated financially. There are lots of easier things I could do to make money, but I like the challenge.
And we have a really good team. The first 10 or 20 employees all made a lot of money, and I think they have the same alignment as me. So the people I get to work with every day have been my friends for a lot of years.
What advice do you have for founders today?
First, find smart people you align with, then work with them as long as you can.
You end up moving at 10x or 20x the speed of everyone else, because you’ve got long relationships with great people that are way better than the people you could normally hire.
That’s all talent density.
My other piece of advice: most founders want to exit too soon, and don’t take enough big swings.
We’ve had multiple acquisition offers over the years, and maybe I have survivorship bias, but I think the longer you go the more your outcomes compound.
Our first acquisition offer was $500K back in 2017. And I almost took it, because it was a lot of money for me then. But two years later we got offered a couple million dollars, then $10M, and so on.
Playing long term games, if you have a plan, is a great way to win. If you can get through the rocky patches, I think most people end up finding success.
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3 things from this week
Appetizer: Did you know the wine market is basically in freefall? All their tailwinds have turned to headwinds. Here’s my take on why.
Main: My friend Sieva Kozinsky wrote about a huge mistake he made. Can you guess where this is going? Read the whole story here (and one-click subscribe, it’s a great newsletter!)
Dessert: At the end of the day, life doesn’t have to be that complicated. What do you think?
Have a great week!
Michael
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