Most product managers are just project managers with a fancier title. They make zero real decisions, answer to everyone, and wonder why nothing ships on time.
Willis Jackson has been building product teams for over a decade. He's blacklisted entire companies from his hiring pool. And he moved to the Bay Area to measure himself against the best—only to find out nobody there really knows how to do product either.
In this episode, Willis and I get into why product thinking is now the most valuable skill in tech, why AI didn't solve the bottleneck problem (it exposed it), and what happens when engineers can build 10x faster but nobody knows what to build.
We also get into his company Middle Mile—basically the Airbnb of e-commerce fulfillment—and why stay-at-home parents running micro-warehouses out of spare rooms might be the future of how your next Amazon package gets delivered.
Fair warning: if you're a product manager who hasn't talked to a customer for two weeks, this episode is going to be uncomfortable.
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⏱️ Episode Breakdown
00:35 Reconnecting and Early Influences
03:27 The Challenges of Product Management
06:34 The Role of AI in Product Development
09:32 Understanding Risks in AI and Software Development
12:34 Bottlenecks in Product Teams
15:25 The Importance of People in Business
18:17 Innovative Fulfillment Solutions
21:39 The Journey of Building a Business
Links & Resources
Connect with Willis Jackson III on LinkedIn
What Smart CTOs Are Doing Differently With Offshore Teams in 2025
Subscribe to the Global Talent Sprint
Full Scale – Build your dev team quickly and affordably
If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.
Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.
