How AI Startups Can Win With Better Strategy - Ep. 50 with Mike Maples

Mar 5, 2025

Mike Maples, a veteran venture investor and co-founder of Floodgate, shares insights on AI startups and strategic advantages over giants like OpenAI. He reveals the importance of counter-positioning and adapting to technological inflections that reshape business models. Discussing outcome-based pricing and cultural shifts, Mike emphasizes how smaller teams can innovate faster. He also explores the balance between integrated and modular solutions, and how AI transforms product development and fundraising, giving startups an edge in a competitive landscape.

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INSIGHT

Counter-Positioning Beats Product Parity

Counter-positioning the business model can disorient incumbents and create huge advantage.
Shift from selling software seats to substituting labor or outcomes can bypass entrenched pricing norms.

INSIGHT

Harness Inflections For Asymmetric Wins

Sea changes shift which business models are attractive and create asymmetric opportunities.
Startups should harness inflections to wage 'asymmetric warfare' on incumbents' rules.

ADVICE

Sell Outcomes, Not Seats

Try outcome-based pricing when you can unambiguously 'ring the bell' for customers.
Price by delivered value or tasks rather than by seats to capture labor-cost buckets incumbents ignore.

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Mike Maples knows how AI startups can beat incumbents with billions of dollars.

Mike—who wrote early checks to Twitter, Twitch, Okta, and Lyft, and now invests through Floodgate, the fund he cofounded—told me it's not about the smartest model, or raising the most money.

Startups can win in AI with better strategy.

AI is changing the economics of startups—both how they’re started and how they’re funded. A new breed of companies is emerging, and I invited Mike on the show to talk about how they can best strategize. Last year, Mike co-authored a book called Pattern Breakers, which is essentially a guidebook to why there’s no guidebook to building companies. I really liked it, and my colleague Evan Armstrong reviewed it for Every, so I was glad to have him on. We talk about how shifts in technology create space for smaller players to compete—even with AI giants like OpenAI—and how to capitalize on them.

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Timestamps:

Introduction: 00:02:20
Innovate the business model, not just the product: 00:06:02
How startups can compete against the likes of OpenAI: 00:15:49
Mike’s take on DeepSeek: 00:19:34
Why the future has always belonged to the tinkerers: 00:21:44
How small teams today can make big money: 00:24:03
Find niches that incumbents can’t or don’t want to enter: 00:28:55
The qualities of the truly AI-native: 00:47:08
How AI changes the funding model for software companies: 00:53:46
Knowledge work is moving toward systems-level thinking: 00:58:23

Links to resources mentioned in the episode:

Mike Maple: @m2jr
The fund Mike confounded, Floodgate: @floodgatefund
Evan’s piece reviewing Pattern Breakers: "A New Book of the Startup Bible"
Dan’s piece on the allocation economy: "The Knowledge Economy Is Over. Welcome to the Allocation Economy."