How You Actually Feel Selling Your Company, Is It Worth Tolerating a Toxic Employee, & TechCrunch’s Former Editor in Chief Reflects on His Decade at the Helm [linkblog]

Hunter Walk
3 min readSep 23, 2023

For your weekend pleasure

When It’s Over & Helpful Boards [Jared Hecht/GroupMe, Fundera] — Two more great posts from one of my favorite founder bloggers right now. The former is about deciding to sell your company and the emotional journey accompanying the pragmatic one.

After selling groupme I once had a VC tell me he didn’t know if I had the courage to build a great company since we sold so quickly. These stories and interactions compound and create an illusion of the characteristics we are supposed to have and the iconic people we are supposed to emulate.

But fuck that. My take is so long as you always value and treat your team, investors and customers well, you’re okay. And if you can make everyone money along the way all the better. When you know you know.

‘Helpful Boards’ is self-descriptive, and contains many of his own personal experiences with Board members who helped him be a better CEO. Several specific characteristics of good Board members and Board dynamics. I’d suggest any founder with investors on their Board (or who plan to have them later in their startup’s lifecycle) read this one and use it as a discussion piece if needed.

Scott [Feldman] told me during a board meeting that I was going to run the business [Fundera] into the ground and bankrupt it, and that it’s value was approximately jack shit. I hated him for it, but he was just providing honesty and tough love. I learned a lot from that experience, and finally familiarized myself with terms like trailing twelve months revenue and ebitda margins. He had the courage to tell the truth and that changed the trajectory of the business.

The Irreplaceable but Toxic Employee [Jason Lemkin/SaaStr] — My counsel is not to tolerate it. This is different than someone who is prickly or still improving their ‘people skills.’ Jason also recommends against it — relating his own experiences as a CEO — but understands that occasionally it’s a reality, and in those cases, “Sometimes, still hire them. But … only 1 of them. Only 1. And start working on their replacement…



Hunter Walk

You’ll find me @homebrew , Seed Stage Venture Fund w @satyap . Previously made products at YouTube, Google & SecondLife. Married to @cbarlerin .