PSJ #14 — Matt McIlwain

Here’s your PSJ weekly — an insider take on Seattle startups and the people behind them.


This week I talked to Matt McIlwain, Managing Director at Madrona. He shared lessons from 20 years of investing, traits of successful leaders, and how great companies got past their low points.

🎧Podcast here.

I enjoyed Matt’s learning loop framework. He went into detail about how the best leaders bring a unique blend of curiosity, humility, and conviction:

“It’s a curiosity that's grounded in humility. That I think really sets the best entrepreneurs up for the highest potential for success,” Matt said.

But he said that founders also have to act as “Chief Sales Officer.” And to do this, he says it’s all about clarity:

“I think what's interesting is that sometimes the most talented people, one of their gifts is being able to explain clearly to others.”

He cited Sujal Patel, founder & CEO of Isilon, as an example. Matt witnessed how Sujal simplified and explained very complex ideas about data storage in a way that inspired investors, employees, and customers to enroll in his vision. Those conversations gave Matt confidence that Isilon had founder/market fit. That one worked out pretty well!

Matt’s book recommendation is by Essentialism by Greg McKeown. I’m still trying to figure out “The Disciplined Pursuit of Less” in practice so going to put this back on my list.