The HubSpot Deal: Radical Transparency as a Negotiation Weapon
The Story
When HubSpot expressed interest in acquiring The Hustle, the initial conversations were vague. Sam cut through it by asking directly: “Do you want to acquire the company?”
Then he did something counterintuitive in M&A, where sellers usually hide weaknesses. He sent HubSpot an email listing every reason The Hustle sucked AND every reason it was great.
No investment banker. Sam distrusted them. Instead, he used high-end lawyers and consulted founder friends (Dave Nemetz, Ramit Sethi) from his Hustle Con network. He also created a bidding situation by having multiple parties interested.
The deal: 27M. HubSpot’s stock doubled after the acquisition.
Sam has said The Hustle would be worth “north of $100M” today.
Lesson for Creators
Radical transparency disarms. Most negotiators hide weaknesses, which creates suspicion. Sam led with his flaws and let the buyer focus on strengths. This builds trust faster and positions you as someone confident enough to be honest. Whether you’re negotiating a brand deal, a partnership, or selling a business: tell them what’s wrong before they find out, and they’ll trust you more on what’s right.
Related
- Disagree, Commit, Then Reverse — Boris built trust through honesty even when it meant admitting disagreement with leadership
- Beer with the Skeptics Before Pitching the Idea — Boris led with vulnerability to win over skeptics, the same disarming transparency Sam used with HubSpot
- Bunk - His First (Tiny) Acquisition — Sam’s first tiny exit taught him the acquisition process he later executed at 1000x scale