#145 Capitalist by Day, Spiritual by Night - Alex Hardy on achievement, Wall Street, tech startups, exiting his company, pride & suffering, his sabbatical, suppressing his curiosity and rediscovering his passions

Alex was crushing it early in his career, ending up on Wall Street after getting a combined JD/MBA.  But after a few years, he went looking for his next mountain, aiming his ambition at the tech sector. He ended up co-founding LiveOak, a company he eventually sold in 2020. After that, he struggled to determine what was next and finally decided to walk away from more than a million dollars. Now he's embracing non-doing, reconnecting with his passions, and figuring out what's next.

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⌛TIMESTAMPS

• (01:08) - The scripts Alex grew up with
• (10:06) - Law School & Business School
• (22:41) - Wall Street, Banking & The Pride in suffering
• (30:55) - Tech Start-ups, coffee meetings and friendlessness
• (56:19) - Exiting his tech company & "Total Work"
• (01:14:24) - His Sabbatical, Finding Work Worth Doing & The American Mind
• (01:21:05) - Forgotten Hobbies, Borders & The Love for The Present
• (01:29:02) - Closing remarks

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What is The Pathless Path with Paul Millerd?

The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.