Product Growth Podcast
with Aakash Gupta
The AI-Native PM Operating System
Live demo of Mike’s composable AI operating system — how he turns Claude + MCP into a real PM workflow.
Currently — Head of Product & AI, David’s Bridal · Building Pearl Planner
BROOKLYN, NY · EST. 2010
I build AI products.
I lead the teams that ship them.
Product leader specializing in AI-native products. Head of Product & AI at David’s Bridal, building Pearl Planner. Previously Automattic (WooCommerce, Blaze), EIG (Luster.ai), 10up, DocuSign. Advised Google, Microsoft, Meta, Starbucks.
- Years building product
- 12+
- AI products shipped 0→1
- 3
- Newsletter readers
- 38.4k
- New-user acquisition (Woo)
- 8×
P
Currently building
Pearl Planner — an AI-native wedding planning platform at David’s Bridal.
Selected work
The portfolio is navigable by skill.
Twelve years of shipped work across AI, ecommerce platforms, ad marketplaces, and publishing systems. Open the work explorer and filter by the skill you care about.
~/writing $ ls –recent
Writing
& thinking.
Essays, podcast appearances, and bylines on AI-native product work, MCP, evals, and the craft of shipping with agents. Home base is the Leading Product newsletter — 38,400 readers Sunday mornings.
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38,400 readers
Sunday mornings. One essay on building AI-native products — evals, MCP, prompt infra, the operator’s view.
› essays [recent]
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$ featured
Wedding Color Studio — A Case Study in Shipping AI as Product
A David’s Bridal-branded React + Gemini app that turns a five-color palette into a named identity, a generative editorial mood board, a six-scene vision board, and a shoppable bridesmaid lineup — wired end-to-end with the polish of a shipping product.
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Build a Composable AI Operating System
Building Your Personal Command Center Learn how to become a 100X PM with a composable tool stack you can run from your favorite AI…
Read →
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How to 10x Quality and Consistency With LLMs
Go beyond your default LLM chat and give yourself real PM superpowers in minutes.
Read →
› podcasts [recent]
Supra Insider
with Ben Lang & Bobby Pinero
AI tooling and MCP demos for product teams
Why MCP changes the shape of internal product tooling — and a walkthrough of the stack Mike actually uses.
Search Engine Journal
Feature
Automattic’s Blaze brings WordPress posts to ad networks
Coverage of the Blaze Ad Platform launch and what it means for the long tail of WordPress publishers.
› bylines [archive]
Endorsements
What the people I’ve worked with actually say.
Pulled from managers, direct reports, and peers across the last decade. Real names; full versions on the endorsements page.
What my managers say
Mike is the rare product leader who can shape a vision, ship 0→1, and then teach the rest of the org to do the same. Every team I’ve put him on has come out sharper.
Jake Miller · President · Engineered Innovation Group
He took on Woo Express when it was still ideas on a wall and turned it into one of the cleanest product launches we’ve shipped at Automattic.
Mary Hubbard · VP of WooCommerce · Automattic
Mike sees the product, the team, and the business as one system. That’s vanishingly rare.
Grant Landram · President · 10up
What my teams say
He’s the manager who will both raise the bar and clear it for you. I learned more in two years working for Mike than the previous five.
Eric Binnion · Senior Product Manager · Automattic
Calm in the room, fast on the keyboard, sharp on the strategy.
Brandi Awbrey · Product Lead
What my peers say
If you want one person who can lead the AI product motion and make your existing PMs better at the same time — it’s Mike.
Beau Lebens · Head of Product · Automattic
I trust Mike’s read on AI more than almost anyone else’s in this industry.
Joshua Fisher · Founder · Yardstick