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Venture Cycles and Hard Lessons with Matt McIlwain (Madrona)

Driving Alpha

Release Date: 04/10/2025

Francisco Gimenez (8VC) on Spotting Biotech Unicorns Others Miss show art Francisco Gimenez (8VC) on Spotting Biotech Unicorns Others Miss

Driving Alpha

Francisco Gimenez, Partner at 8VC, shares his unconventional journey from Stanford PhD to venture capital, where he leads investments in Bio-IT and enterprise AI. Known for his technical background and sharp instincts, Francisco has been pivotal in backing startups pushing the boundaries of biotech and healthcare innovation.   Here’s a glimpse of what you’ll learn: 00:48 Introduction to Driving Alpha 01:18 Meet Francisco Gimenez: A Journey from Academia to Venture Capital 02:45 Francisco's Early Career and Academic Background 04:02 Joining Formation Eight and Transition to 8VC...

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AI Meets Venture: Ben Orthlieb (Blue Moon) on Outperforming Traditional VCs show art AI Meets Venture: Ben Orthlieb (Blue Moon) on Outperforming Traditional VCs

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What if AI could predict which founders will build billion-dollar companies? Ben Orthlieb, co-founder of Blue Moon, is doing just that, using AI and behavioral science to consistently outperform even the top VC firms. With roots at LinkedIn and Emergence, Ben brings a rigorous, founder-first model to seed investing. Here’s a glimpse of what you’ll learn: 00:00 Intro to Driving Alpha 00:41 Meet Ben Orthlieb of Blue Moon 01:20 Why “2.12” wasn’t working—and how “Blue Moon” captures their true identity 02:05 The meaning behind both names—and what they signal to founders ...

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Brice Penaud & Jonathan Taylor of Water Bear Ventures: Investing in Resilience and Founder Grit show art Brice Penaud & Jonathan Taylor of Water Bear Ventures: Investing in Resilience and Founder Grit

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What if the key to outsized venture returns isn’t just a great idea but the unshakable resilience of the founder behind it? Jonathan Taylor and Brice Penaud of Water Bear Ventures believe grit is the ultimate differentiator, and they’ve built a fund around finding it. Jonathan brings years of experience driving strategic outcomes in venture, while Brice draws on a behavioral science background to decode the mindset of top-tier founders. Here’s a glimpse of what you’ll learn: 00:00 Introduction to Driving Alpha 00:43 Meet the Water Bear Team 02:15 The Origin of Water Bear Ventures...

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What does it take to turn early traction into scalable momentum? And how do you know if your startup—and your engine—is even built for venture capital? Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast   02:20 Meet Manishh Patel: From Google to Nava Ventures   03:17 Growing Up in Rural Kentucky   05:24 The Journey to Venture Capital   08:17 Founding Nava Ventures   16:22 The Series A Focus   19:57 Building the Flywheel: Operational Infrastructure   20:41 Refining the...

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Can deep operational experience shape better venture outcomes? One VC proves it can—drawing from years in the founder seat to back today's most promising startups. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast   01:05 Eric's Background and Career Journey   03:45 Transition to Venture Capital   06:27 Eric's Role at S3 Ventures   07:19 Investment Philosophy and Market Insights   12:12 Texas Venture Ecosystem   20:18 S3 Ventures' Unique Structure   29:56 Advice for...

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Can Middle America become the next innovation powerhouse? Aziz Gilani, General Partner at Mercury, thinks so—and he’s proving it by backing cloud and enterprise software startups across Houston and beyond. With a track record that includes major exits like Black Lotus and Modus, Aziz has helped Mercury’s portfolio reach over $9 billion in enterprise value. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha   00:51 Meet Aziz Gilani: Venture Powerhouse   02:08 Aziz's Journey to Venture Capital   04:20 Houston: A Hub for...

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Venture Cycles and Hard Lessons with Matt McIlwain (Madrona) show art Venture Cycles and Hard Lessons with Matt McIlwain (Madrona)

Driving Alpha

Matt McIlwain, Managing Director at Madrona, has spent over two decades investing in intelligent applications and driving innovation in AI. With a track record including Smartsheet, Apptio, and Isilon, he brings rare perspective from 25 years in venture capital. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast 00:57 Guest Introduction: Matt McElwain from Madrona 01:41 Matt's Journey into Venture Capital 03:06 Early Years at Madrona and the Dot-Com Bust 04:45 Madrona's Investment Strategies and Success Stories 06:29 Driving Alpha for Portfolio...

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Lisa Chai, co-founder and general partner at Interwoven Ventures, joins Driving Alpha to discuss how robotics and AI are transforming industrial technology. With a deep background in venture capital and public markets, Lisa shares her insights into the megatrends driving automation, reshoring, and industrial AI. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast  00:53 Meet Lisa Chai of Interwoven  01:10 Interwoven's Focus and Investment Strategy  02:04 Lisa Chai's Origin Story  06:24 Challenges and Gender Dynamics in Venture...

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Bob Ackerman saw the future of cybersecurity before the market did. As the founder of AllegisCyber Capital, the first venture firm dedicated 100% to cybersecurity, and the co-founder of DataTribe, he’s been at the forefront of investing in cyber defense. With a 20+ year track record, Bob has backed some of the most cutting-edge cybersecurity companies, navigating the intersection of venture capital, AI, and national security. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha 01:00 Meet Bob Ackerman: Cybersecurity Visionary 02:15 The Birth of AllegisCyber ...

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David Hornik, founding partner at Lobby Capital, has spent over 25 years shaping the venture capital landscape. Formerly a lawyer with degrees from Stanford and Harvard, David transitioned into venture capital, making early bets on companies like Splunk, Build.com, and GitLab. His career is marked by a passion for helping founders, fostering strong industry relationships, and identifying high-potential investments. Here’s a glimpse of what you’ll learn: 00:43 Introduction to Driving Alpha Podcast 01:57 Meet David Hornick: From Law to Venture Capital 03:43 Early Ventures and Key...

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More Episodes

Matt McIlwain, Managing Director at Madrona, has spent over two decades investing in intelligent applications and driving innovation in AI. With a track record including Smartsheet, Apptio, and Isilon, he brings rare perspective from 25 years in venture capital.

Here’s a glimpse of what you’ll learn:

  • 00:43 Introduction to Driving Alpha Podcast

  • 00:57 Guest Introduction: Matt McElwain from Madrona

  • 01:41 Matt's Journey into Venture Capital

  • 03:06 Early Years at Madrona and the Dot-Com Bust

  • 04:45 Madrona's Investment Strategies and Success Stories

  • 06:29 Driving Alpha for Portfolio Companies

  • 09:34 Evaluating Founders: The Power of Why

  • 24:49 Navigating Exits and M&A Landscape

  • 28:25 Life Lessons and Long-Term Perspective

  • 32:40 Conclusion and Future Outlook

 

In this episode

Matt recounts his unconventional entry into venture capital—from auto parts to Amazon-era Seattle—and how he joined Madrona just before the dot-com crash. He reflects on the firm’s resilience through market downturns, the evolution of their early-stage to acceleration-stage investment strategy, and how conviction-driven bets like Isilon and Smartsheet became fund-makers despite difficult timing.

Matt breaks down his “power of why” framework for evaluating startups, emphasizing founder-market fit and the value of long-term thinking. He shares candid insights into Madrona’s hands-on approach with founders, how he spots extraordinary teams, and why curiosity is the ultimate trait in successful entrepreneurs. From navigating exits in today’s M&A climate to building enduring partnerships, this conversation is a masterclass in venture capital longevity.