Matt McIlwain: The Learning Loop [Built in Seattle Ep. #22]
2 min read

Matt McIlwain: The Learning Loop [Built in Seattle Ep. #22]

Matt McIlwain, Managing Director at Madrona, shares his lessons from 20 years of tech investing, Madrona's "bigger pie" mission, and what he sees in the best leaders.

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Matt McIlwain's results stand out.

20 years as a VC at Madrona. Headline IPOs like Accolade, Smartsheet, Apptio, Isilon. Invested in cloud before it was cool. 3x Midas list. 3x CB's top 100 VC list. That's just the start.

But he's remained on earth. He shows up without ego. He's willing to share the struggles and get into the learning process.

Matt shares his lessons on this episode of The Built in Seattle Podcast.

Episode Highlights

  • Why Madrona wants to build a bigger pie of success in the community.
  • How a multigenerational team has defined Madrona's values for 25 years.
  • Assessing  founder/market fit and why it matters.
  • Lessons from the dot-com boom and bust.
  • Why founders explaining complex ideas simply is an investor signal.
  • How founders become the Chief Sales Officer
  • How "the learning loop" works for the best founders.
  • Why selling a vision starts with humility and curiosity.
  • What it takes to get through the low points in company building.
  • How Madrona decided to stick with Smartsheet in their hardest times.
  • The intersection of computer science with biological and chemical sciences.
  • What Matt is excited about next.

Matt McIlwain Bio

Matt is a Manager Director at Madrona Venture Group where he invests in a broad range of software and data-driven companies with a focus on cloud computing, intelligent applications, and the intersection of the digital and physical world. He believes in the Learning Loop for entrepreneurs who journey from curiosity to triangulation and decision making. This leads to outcomes and ongoing learnings.

Before joining Madrona in 2000, Matt was vice president of business process for the Genuine Parts Company (NYSE: GPC). He also was an engagement manager at McKinsey & Company, concentrating on strategy and marketing in technology-driven sectors and prior to that worked in investment banking at Credit Suisse.

Matt is the Chairman of the Board of Trustees of Fred Hutchinson Cancer Research Center and a board member of Washington Policy Center. Matt enjoys going on adventures with his family, discussing public policy issues, and trying out new technologies. He is also an avid runner, Peloton biker, and a major Sounders and Seahawks fan.

In 2017, Matt was named Emerging Company Director of the year by the Puget Sound Business Journal, in partnership with the prestigious National Association of Corporate Directors’ (NACD) Northwest chapter. In 2011, he received the Washington Policy Center’s Champion of Freedom Award. He has also been named several times to both the list of Top 100 Venture Capitalists by CB Insights and The New York Times and the Forbes Midas list.

Matt is a graduate of Dartmouth College and holds an MBA from Harvard Business School and a Master’s in Public Policy from Harvard’s Kennedy School of Government.