How This Software Engineer Bought an IT Business He'd Never Heard Of (and Kept His Day Job)

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Christian's whole journey started at a free Codie event. He showed up hungry, knowing nothing about the industry he'd eventually buy into.

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Christian Riboldi builds software for a living. He’s got a W-2 job, a loving wife, and 4 beautiful kids. The 4th arrived mid-search, which we'll get to.

About a year and a half ago, he decided he wanted ownership.

So he did something about it and signed up for Main Street Millionaire Live even though he'd never heard of Codie. Christian was just hungry for knowledge and saw an event about buying businesses.

He joined the Academy at the end of it, tore through the course in a couple of weeks, and fired off his first LOI almost immediately.

After becoming an Academy ambassador and getting his reps in, he closed on a managed IT services business back in July. Here's everything that happened in between, and what you can use in your own search.

Christian's first LOI? A $5M deal with roughly $1M in SDE.

"I was like, this would be so sweet, and we'll figure out how to fund it later."

The sellers wanted a multiple well above the 3 to 4x range we teach, so while this deal died, Christian kept the education.

"Every single time I put in an LOI, I learned a whole lot about myself [and] what I even consider to be a good deal."

He submitted 5 LOIs over the course of the next year and change, and finally, the 6th one went all the way.

The lesson: Your first LOI teaches you more than your first 10 hours of research. Put in the reps early, because while it feels scary, each one gets you closer to where you want to be.

A fellow Academy member had just closed on their own business when they sent Christian a listing with a note: you should buy one of these.

It was managed IT support for small businesses.

Funny enough, Christian writes software for a living and had never heard of the industry. Turns out it was a great (if relatively niche) opportunity. And while that specific deal was too big, it pointed him at the exact type of business he'd close on months later.

The lesson: Deal flow follows people who broadcast what they want. Your next deal might be sitting in someone else's inbox right now.

The conversations that unlocked Christian's deal happened inside the Contrarian Academy. If you want the same playbook, and the same room, start here.

After baby number 4, the search stalled.

It took two things to restart it:

First, Christian's wife joined the hunt and started surfacing good deals. We talk all the time about how labor intensive finding a business can be, and it’s easy to get burned out. Having someone help you hunt doesn’t just decrease your workload, it keeps you from getting cynical and giving up.

Second, he sat down with fellow members Ellie, Paige, and Michelle at our Main Street Over Wall Street event and talked partnership for the first time.

That conversation is what finally helped things click. Running a business solo didn't work for Christian’s situation. 4 kids, full-time job, and being human all take time and energy... But with a trusted operator handling the day-to-day and earning equity over time? That could work. Christian brought the capital and the technical expertise, while his operator brought the hours.

And the idea is to slowly taper his own involvement as the operator trains the team.

"If I hadn't had that mindset of being willing to bring someone on, I would never have closed on this deal."

The lesson: The deal you can't do alone might be the deal you can do together. Explore partnership structures before you need one.

The best advice Christian got: "I would prefer to overpay for really good professional due diligence than underpay and get a surprise later."

So he hired a CPA for a quality-of-earnings report and a lawyer to carry him through close. He told us it was about $22,000 all in, and worth every penny.

Then his loan broker found a lender willing to roll that cost into his equity injection requirement, which shrank the cash he had to bring to the table on closing day. We call that a win-win.

The lesson: Due diligence feels expensive until you skip it. Buy the certainty.

The business: listed at $1.5M, with $300K in SDE on $500K in revenue.

The broker told Christian there were already 2 offers on the table at $1.2M each, both leaning on a large seller note the seller didn't love. So Christian offered the same $1.2M with cleaner terms, and the seller picked him. In the end, the deal looked like this: 75% SBA loan, 15% seller note, and 10% cash.

Then he backed it up. His loan broker handed him a checklist of everything the lender would ask for, so he had it ready before anyone asked. And his seller stayed motivated and communicative the whole way through.

The result: 15 business days from finished underwriting to close. 52 calendar days from signed term sheet to keys.

The lesson: Sellers say they want the highest number. They pick the offer they trust to actually close, and you earn that trust by being ready.

Christian is 2 weeks into ownership and told us it’s like drinking from a fire hose.

He's now running our playbook:

And when you ask him if it was worth it, he doesn't hesitate.

"This isn't a golden ticket. It's a lot of work. But it's good. It's worth it."

6 LOIs. 5 passes. 1 yes.

If you’re in the middle of your business buying journey, never forget: it doesn’t matter how many deals fall through. You only need ONE to close.

- Team Contrarian

CALLING ALL OWNERS!

If you already own a business, you know that feeling. Every question routes through you, and growth stalls right where your available hours run out.

The Growth Accelerator Workshop gets you out of the weeds over a few days in Austin, in a room with operators who've already scaled past where you're stuck.

You'll find where growth leaks out, rank your next moves with real ROI math, and decide what to scale, fix, or kill. Then you walk out with a battle-ready 90-day roadmap.

Most owners don't need another idea. They need someone to tell them which 1 to focus on.

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