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🎙️This Big Law Partner Rolled Up 3 SaaS Companies And Sold to PE (All in 20 Months)

Author

Helen Guo
December 05, 2025

Hello SMB Deal Hunters!

This week's greatest hits episode with Brian Wolfe started where a lot of you might be right now.

Brian was a partner at a Big Law firm. He’d climbed to the top of the corporate ladder.

But he kept seeing the same playbook among his clients: PE firms doing rollups in fragmented spaces, buying competitors, growing organically, and selling for massive multiples.

And he realized he was watching from the sidelines.

Then someone from his Chicago community (who had bootstrapped and sold a SaaS company) asked if he wanted to partner and do it themselves.

Brian had an insight from watching all these deals get done: The power of multiple expansion. He calls it "the eighth wonder of the world."

So, how did they execute on it?

🚀 They did a SaaS rollup in MarTech, buying companies that helped people rank on Google search.

🚀 They closed 3 deals in 20 months (and found very creative ways to source them)

🚀 They exploited SaaS arbitrage: Low-growth SaaS companies (3-5%) sell for 1-2x revenue. Could they buy them, invest in sales/marketing, grow to 25-30%, and sell at 5-6x?

🚀 They sold the roll-up to a big PE firm in record time, closing in a matter of months from their first conversation.

And for our audio-only listeners, jump in and listen on Spotify or Apple Podcasts!

Alumni Spotlight

For those who missed it, we also did an SMB Deal Hunter Pro case study breaking down Iris’s acquisition of a recruiting agency cashflowing $400k / year.

She did it in 4 months.

Why was she in such a rush?

Because she had just been laid off from her job as an engineering manager at a major tech company.

And she was 3 months pregnant. So, she decided to join the Pro program.

The result?

🚀 We helped her find an $1M agricultural recruiting agency cash-flowing $400K/year

🚀 4 months from joining to closing (6 weeks before her baby arrived)

🚀 She closed at a 2.4x multiple (most people pay 3-4x)

She closed the same month as a friend who had also been searching. Except he’d been looking on his own for 2.5 years.

Same goal. Very different paths.

And here’s what she had to say when we asked her about her experience:

I think that people sometimes can be very illogical when they think about making a decision to join a program like this.

And they might be focused on the fact that you have to pay a fee and that fee is not cheap, right?

But if you're gonna be dropping $100 - $500k on a down payment for a business, then the fee to do the program is literally inconsequential relative to what you're paying for the acquisition.

And I think the benefit of the program, comparatively, is just so immense that I just don't see why you would want to do it on your own.

— Iris

So, if you want me and my team to work with you to find, finance, and acquire a million-dollar cash-flowing business in the next 6-12 months, you might be interested in the Pro program.

P.S. We’re going to be raising prices on Jan. 1st. We’ve spent the last year…

  • Helping our members close over $115MM in deals

  • Doubling the M&A advisors every Pro member has 1:1 access to

  • Building an off-market marketplace with hundreds of listings no on else can access (more added every week)

COMMUNITY PERKS

• Ready to buy and operate a $1M+ business? Get expert help at every step.

• Want to invest passively in SMB acquisitions? Get access to investment opportunities.

• Get a personal introduction to my preferred SBA 7(a) lender, non-SBA lenders, Quality of Earnings providers, or legal counsel

• Raising capital for your deal? I’ll connect you with investors from the SMB Deal Hunter Community.

• Interested in selling your business? I’ll help you connect with buyers from the SMB Deal Hunter Community.

THAT’S A WRAP

Want me to interview you for my podcast? Hit reply.

See you next week with some new deals!

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Disclaimer

This publication is a newsletter only and the information provided herein is the opinion of our editors and writers only. Any transaction or opportunity of any kind is provided for information only; SMB Deal Hunter does not verify nor confirm information. SMB Deal Hunter is not making any offer to readers to participate in any transaction or opportunity described herein.