Phil Taylor, CTO ⁨@CDW⁩ , built a 250-person services company from the ground up, sold it to CDW, and now runs their Digital Velocity business unit. But what makes his story compelling isn't the exit — it's how he got there.

At 21, he was distributing half a billion dollars in checks. One error could've bankrupted the company. Years later, he learned the hard way that being right matters less than helping your team win. He'll tell you about the Silverlight bet that taught him to ship imperfect products fast, the founders he picked wrong, and why his best business came from investing in people he let go.

He's also refreshingly honest about AI hype, why most services companies miss the obvious, and how to actually scale when you can't touch the code your teams are shipping.

If you're building a company, leading engineers, or trying to figure out how to compete without a shiny product, this one's worth your time.

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Timestamps

00:00 Meet Phil — from software engineer to CTO at CDW

01:51 The builder mindset, started at age 13

02:30 Distributing $500M in checks at 21

04:38 The team rebellion that humbled him as a leader

05:37 Choosing to win with your team, not be right

06:56 Ship value fast — perfect is the enemy of good

07:19 Listen to customers, don't sell them

09:09 The honest manager who told him to go start something

10:11 Building serverless before AWS Lambda

11:06 Pivoting to services, betting on Kubernetes

12:44 Exiting to CDW during the pandemic

13:28 Investing in people — your best network effect

15:32 The jump to enterprise — processes and structure

18:40 Running services like a product with real standards

19:08 AI quality control — why manual testing still matters

21:18 Staying on top of innovation

24:13 Zero to one in consulting — partnerships first

26:04 Building your portfolio of capabilities

28:40 AI is overhyped, cloud is a journey

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🔗 Connect with Phil Taylor → https://www.linkedin.com/in/ptaylor1/

🔗 Connect with Mala Ramakrishnan → https://www.linkedin.com/in/malaramakrishnan

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