The instinct is always to wait. Revenue is growing. The team is strong. The pipeline is full. Why would you have a conversation about partnership when everything is working?
Because that’s exactly when you have the most leverage, the most options, and the clearest thinking.
The founders who end up in the worst deals are the ones who come to the table under pressure. A key employee left. A major client churned. Cash flow tightened. Suddenly, the conversation shifts from “what do I want?” to “what can I get?” And the terms reflect that shift.
The Strength Position
Jason Hennessey didn’t partner with Herringbone Digital because Hennessey Digital was struggling. The agency was a 7x Inc. 5000 company with eight-figure revenue and a dominant position in legal SEO. He came to the table from strength, which meant he could be selective about the partner, the terms, and the structure.
Micki Love at CJ Advertising had 15 PE firms pursuing her. She wasn’t shopping the business. Buyers were coming to her. That dynamic exists because CJ had something rare: 30 years of proprietary data, deep client relationships, and a brand that couldn’t be replicated. She had the luxury of choosing the partner that aligned with her values rather than accepting the highest bid.
Seth Price built BluShark Digital into a category leader serving over 300 law firms. The business was healthy, but Seth also recognized that the landscape was shifting. AI, consolidation, and increasing competition meant that the strongest position to negotiate from was today, not tomorrow.
The Risk of Waiting
Every founder who delays the conversation is making an implicit bet. They’re betting that the business will be worth more next year than it is today. Sometimes that bet pays off, but it carries risks that founders chronically underestimate.
Market conditions change. The M&A environment that favors agencies today may not exist in two years. Interest rates, buyer appetite, and competitive dynamics all fluctuate in ways that individual founders can’t control.
Key person risk is real. Most agencies are built around a small number of high-performers. One departure can materially impact revenue, client retention, or operational capacity. The value of the business today includes those people. Tomorrow is uncertain.
AI is reshaping the landscape faster than most founders appreciate. The agencies that integrate AI effectively will pull ahead. The ones that don’t will find their competitive position eroding. Inside a portfolio with shared AI investment and 70+ experiments running, that adaptation happens faster.
And the playbook that built the agency to its current size rarely scales it to the next level without significant investment in people, technology, and infrastructure. The gap between $8M and $20M is wider than the gap between $2M and $8M, and it requires different capabilities.
What the Conversation Actually Looks Like
Exploring a partnership doesn’t mean committing to one. The initial conversation is confidential, low-pressure, and designed to help both sides evaluate fit. Most of the founders in our portfolio spent months in dialogue before making any decisions.
The goal isn’t to convince anyone to sell. It’s to give founders the information they need to make the best decision for themselves, their team, and their clients. Sometimes that decision is to partner. Sometimes it’s to keep building independently. Either way, having the information is better than operating in the dark.
If you’ve built something valuable and you’re curious about what the next chapter could look like, the strongest move is to start the conversation while you’re in a position of strength. Reach out to the Herringbone Digital team for a confidential discussion.