Dan Fleyshman is back on Digital Social Hour — and this one goes deep into money, Bitcoin, business, events, poker, and why life is way too short to play small.
Dan breaks down why he believes Bitcoin will eventually be worth millions per coin, how banks profit by slowing down your money, and why Ethereum may be more useful but harder to predict. He also shares insane stories from poker, side bets, crypto mistakes, building Who’s Your Daddy into a major brand, throwing million-dollar events, and why networking still changes everything.
From losing out on millions in Ethereum to building masterminds with celebrities like Mark Wahlberg, Shaq, Floyd Mayweather, Kris Jenner, and more — Dan explains what it really takes to build at scale.
🪙Bitcoin: https://tickets.b.tc/event/bitcoin-2026?promoCodeTask=apply&promoCodeInput=dsh
Chapters
0:00 Why Bitcoin Will Be Worth Millions
0:37 Dan Fleyshman Returns To Digital Social Hour
1:19 Living 250 Days A Year On The Road
2:53 Buying Ethereum At $19
4:05 The $1M Ethereum Poker Story
6:37 Why Bitcoin’s Supply Is Disappearing
8:58 Bitcoin vs Ethereum
10:08 HIMS Ad Break
11:03 Why Banks Slow Down Your Money
12:14 Poker, Side Bets, And Wild Gambling Stories
18:19 Breaking Guinness World Records
21:30 Why Entrepreneurs Can’t Stop Working
23:26 Building Who’s Your Daddy At 18
30:59 The Power Of Events And Networking
38:26 Selling A $100K Mastermind With No Ads
42:13 The Biggest Event Mistakes
47:14 Building An Animal Sanctuary
What You’ll Learn
💰 Why Dan believes Bitcoin will hit millions
📉 Why lost Bitcoin reduces future supply
🏦 How banks profit from slow transfers
⚡ Why Ethereum is more functional than Bitcoin
🎲 Wild poker stories and side bets
🚀 How Dan built a major brand at 18
🎤 What makes events actually work
🧠 Why entrepreneurs are addicted to the game
🎙️ APPLY OR CONNECT
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🎧 LISTEN TO THE PODCAST
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📸 Follow the Host
Sean Kelly on Instagram: @seanmikekelly
⚠️ DISCLAIMER
The views and opinions expressed by guests on Digital Social Hour are their own and do not necessarily reflect those of the host, Sean Kelly, or the Digital Social Hour team.
The host and producers are not responsible for statements, claims, or opinions shared by guests during the show. This content is intended for informational and entertainment purposes only and should not be considered legal, medical, financial, or professional advice.
Listeners are encouraged to do their own research and consult qualified professionals when appropriate. While we aim to share accurate and reliable information, no guarantees are made regarding completeness or accuracy.
🔥 Stay tuned for more conversations with creators, founders, and innovators shaping the digital world.
Keywords
Dan Fleyshman, Digital Social Hour, Sean Kelly, Bitcoin, Ethereum, crypto, cryptocurrency, Bitcoin million dollars, Money Mondays, poker, World Series of Poker, side bets, entrepreneurship, events, mastermind, business podcast, Who’s Your Daddy, business growth, networking, event marketing, animal sanctuary Visit Our Website at https://digital-social-hour.simplecast.com/
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