From a food startup that accidentally became a catering company, to a fitness business he sold, to a real estate tool launching now, Nathaniel McNamara has surfed every tech wave since the first web browser. Building Dealyo, he gets into why focus beats boiling the ocean, how he lost money slowly on Polymarket to learn faster, and why optimism keeps winning the AI argument with his wife.

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0:00:00 The food-to-fitness studio story
0:05:20 Tech cycles from the first browser to AI
0:07:48 Why intelligence keeps getting cheaper
0:13:46 Time off and the projects that didn't stick
0:16:31 How Dealyo started with a real estate headache
0:18:15 Being the service, not just the tool
0:22:15 Single player now, big business later
0:28:10 Houston versus the coastal tech scenes
0:32:16 Why focus beats boiling the ocean
0:37:47 Faster horse or build the car
0:40:05 Spending now to win later
0:44:01 Losing money slowly on prediction markets
0:52:08 Optimism, humanities, and self-driving cars
0:59:28 Staying focused on what's next

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