Reboot Media - The Reboot Chronicles Show

08/01/2026

Retirement is an industrial revolution trap nobody talks about. Think about your next gig and Rebooting your life instead!

Most people spend decades building toward it. Then they get there and realize nobody told them what comes next. The systems around work and aging were built for a world where people lived to their seventies. That world is gone.

A 70 year old today has the same mental and physical acuity as a 53 year old in the year 2000. First time entrepreneurs over 50 are three times more likely to succeed. And 75 percent of global wealth is held by people between 50 and 70. Yet only 5 percent of advertising even talks to them.

CEO and age inclusion pioneer Lyndsey Simpson of 55/Redefined is leading the rebellion against all of it on this episode of The RebootChronicles Show. Tune in to find out why she hired 400 retired bankers back into the workforce using just her cell phone, why self limiting beliefs about aging are literally knocking years off your life, and how to design the second half of YOUR life before it designs itself without you.

Listen/Watch/Subscribe wherever you get podcasts or here:

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Website: https://zurl.co/TYlrO

#55/Redefined

07/15/2026

We’re revisiting a 12-minute clip from our Reboot Chronicles conversation with Morgan Brennan.

Tune in for an insightful discussion on business, leadership, and the stories shaping today’s world.

Watch here: https://zurl.co/pUWgB

07/12/2026

From actor to entrepreneur, Eric Winter is rewriting the rum industry’s playbook.

Best known as Sergeant Tim Bradford on The Rookie, Eric has pursued many paths — from pre-med to actor, producer, and now co-founder of Palm Republic Rum.

Revisit this Reboot Chronicles clip as Eric shares the story behind building an award-winning brand with purpose beyond the spotlight.

Watch here: https://zurl.co/BXH7X

07/08/2026

We’re revisiting a powerful 8-minute clip from our Reboot Chronicles conversation with Joe Moglia — a leader who has proven that reinvention is not only possible, but powerful.

From the high-stakes world of finance as CEO of TD Ameritrade to the intensity of college football at Coastal Carolina, Joe’s journey is a playbook for courage, grit, leadership, and betting on yourself.

Watch the clip here: https://zurl.co/OxEfv

06/22/2026

06/21/2026

Thanks/love to all you remarkable fathers out there around the world...please share your weekend photos!

06/18/2026

🌮🍾

06/05/2026

05/11/2026

While enterprise software giants scramble to reboot around perceived threats and opportunities of the SaaSpocalypse shift show, Infor is blazing new trails.

On this episode of The Reboot Chronicles Show, join me for a behind the scenes tour of how this $3.5 billion company with 17,000 employees and 90,000 partner/clients—like top manufacturers PBC Linear, Timken, and Molex—is rebooting software to drive enterprise outcomes, not just features.

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05/03/2026

Why do people tell you to stay in your lane...is it good advice?
⛔️Maybe not.

Which lane—carpool, breakdown, bike, or slow lane? Next-Gen leaders don’t stay in—they create—lanes!

Few have spent more time inside the minds of the world’s most powerful fast-lane leaders than Yale's Jeff Sonnenfeld. Founder of the Chief Executive Leadership Institute, he has advised five U.S. presidents and thousands of CEOs navigating crisis, succession, geopolitical shocks, and the ever-shifting expectations of corporate governance.

Author of Trump's TEN Commandments - and a trusted voice across CBS, NBC, ABC, CNN, CNBC, Fox, Wall Street Journal, New York Times, Financial Times, & Bloomberg - Jeff has spent a lifetime decoding the human side of leadership in eight books, hundreds of articles, and decades of governance research.

On this special-extended episode of The Reboot Chronicles Show, we unpack rare no-holds-barred stories about how top CEOs are approaching AI and China, what civic duty has to do with corporate strategy, why failure/setbacks are the best leadership lessons…and what open-lane leaders can learn from President Trump’s playbook.

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Reboot Site >> https://zurl.co/XxcYJ