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Conventional M&A wisdom said training companies can't be sold at premium multiples. Too founder-dependent. Too project-based. Too much key-person risk.

DI sold at 4x revenue. Here's what made the difference.

Operational systems. We ran on EOS for four years before the sale. Every leader owned their numbers. Weekly L10 meetings caught issues before they became crises. Quarterly Rocks kept the team focused. The business made decisions without the founder in the room.

Direct client ownership. We went direct to enterprise in 2010. Every client relationship was ours. Every dollar of revenue was earned through relationships we controlled. An acquirer could underwrite that revenue because it didn't depend on a third party.

A transferable contractor model. The 300-instructor network transferred with the business. Instructor relationships, matching processes, delivery operations. None of it depended on me. That's what eliminated the key-person risk that kills most service company acquisitions.

Disciplined financials. 12 months of cash reserves. No debt. Clean books. A business that operated from strength, not from desperation.

The proof: during the 18-month transition to Pluralsight, revenue grew from $12M to $17M. The business didn't just survive without the founder running day-to-day. It grew 40%.

The deal itself took years of conversations and false starts before Pluralsight became the right partner. A few things we learned that apply to any training company owner considering a sale:

Join a CEO peer group. I was part of Vistage for years. Having a room of experienced operators who'd been through acquisitions, who could be honest when you needed it, was invaluable for the emotional arc of selling.

Hire an M&A attorney independent from your investment banker. Your banker's job is to close the deal. Your attorney's job is to protect your interests. Those are not the same thing. Keep them separate.

Know your number before conversations start. The deal process is emotional. Life-changing money makes rational thinking harder. Having a clear walk-away number, defined before any offer arrives, gives you an anchor.

Prepare for the identity transition. For 18 years, I was the founder of DevelopIntelligence. That identity shaped everything. The financial transition is straightforward. The identity transition is harder than the startup years. Expect it. Plan for it.

The highest point wasn't the money. It was the impact on our team members and their families. That's what made 18 years worth it.

Every operational challenge in the DI story is what TryTami was built to eliminate. Managing hundreds of contractors on spreadsheets. Scheduling at scale via email. Tribal knowledge for instructor matching. Manual logistics coordination.

The founder's best value at DI was vision and customer relationships. The operations side was what we spent years trying to backfill. TryTami gives training companies that operational infrastructure from day one.

Instructor matching based on skills, availability, and client fit. Automated scheduling. End-to-end training communications. Real-time reporting.

The delivery infrastructure that took DevelopIntelligence 18 years to build. Available as software.

All four parts in one place: the bootstrap model, contractor economics, the inflection point decisions, and the exit.

Get it here:

Thanks for reading,
Kelby and Dave

About the Authors

Kelby founded DevelopIntelligence, an instructor-led training business, and grew it to an acquisition by Pluralsight. He's building TryTami to automate the operational playbook that made his previous training business work.

Dave is Head of GTM at TryTami. He helped grow DevelopIntelligence with Kelby and has experience at multiple EdTech companies.