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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Episode 33: Daniel Berk – https://www.linkedin.com/in/danielberk – is back with Troy Munson – https://www.linkedin.com/in/troymunson – for a wide-ranging convo that spans euro trips, retirement blueprints, and AI clones. They riff on building wealth without burnout, why vacations matter more than birthday parties, and what happens when your AI twin outlives you. Also: the iPhone is mid, social media might be a drug, and Jeff Bezos (almost) gets a handshake.
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Show Notes:
(0:00) Subscribe on YouTube or else
(0:29) Troy’s intervention? Rebrand talk and show structure
(1:09) Why guests are hard (and unpaid help wanted)
(2:42) Troy’s month in Europe vs. real life in South Carolina
(4:55) Retire by 45 — or maybe 40?
(7:03) Kids, wealth planning, and living now
(9:04) What does “retirement” even mean anymore?
(10:00) Angel investing, advising, and startup stakes
(12:35) The Beehive bet and life after SaaS
(14:04) Building wealth as a parent — risk and responsibility
(16:00) Side hustle mentality and the $100K confidence
(17:19) Digital afterlife and AI twins: what happens when you die?
(19:02) AI clones at work — Adam Robbins goes full simulation
(20:02) Scarlett Johansson vs. AI voices
(21:03) Legal gray zones of deepfake content
(22:00) TikTok shop, AI influencers, and automated income
(23:14) Should the U.S. delete TikTok?
(25:13) Gen Y, Yik Yak, and nostalgia apps
(27:12) Gamified loneliness and doomscrolling depression
(28:30) Are creators addicted, too?
(30:50) Should social media exist at all?
(34:15) What if the internet had a time limit?
(36:00) Is distribution just another name for social media?
(37:08) The future of wearables and AR
(39:01) Is iPhone just… boring now?
(41:26) Leaving Apple? Notes, texts, and bubble shaming
(44:31) Merch plug, Bezos jokes, and outro banter
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Links:
• Daniel Berk's LinkedIn – https://www.linkedin.com/in/danielberk
• Troy Munson's LinkedIn – https://www.linkedin.com/in/troymunson
• Two Dads in Tech Newsletter – https://twodadsintech.com
• Shop Two Dads in Tech – https://shop.twodadsintech.com
• Listen on Spotify – https://open.spotify.com/show/30GQP8FPJoKpLGpYBahlFP
• Listen on Apple – https://podcasts.apple.com/us/podcast/two-dads-in-tech/id1785662964
• Check out Dimmo – https://www.dimmo.ai
43 episodes
