Shark Tank host Matt Higgins makes the case that job autonomy beats money for long-term power. We break down the strategic “burn the boats” mindset (for goals, not tactics), the three-year quit rule, and how to use a big-brand logo as leverage—somewhere else.
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
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22:42
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22:42
Doom Spending vs. FIRE: Can a Kid Pension Fix Retirement?
From vending machines to van life, today’s money plans feel unhinged. On this episode, we welcome special guest Orianna Rosa Royle —award-winning journalist and Associate Editor at the Success Desk at Fortune. She helps us break down Germany’s “start at age six” pension idea, why Social Security fears are fueling bad choices, and the $32 investing habit that could change your future.
Reference Article by
Orianna Rosa Royle
As boomers are forced to ‘unretire’ because they’ve not saved enough, 6-year-olds in Germany could soon have retirement accounts
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
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23:29
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23:29
How Do You Get Hired in an Employers' Market?
Instead of chasing openings, how do you become a candidate that employers chase? We cover Madeline Mann's "job shopper" system: targeted networking that isn't cringe, the 10%-above rule, work-sample binders that win interviews, and the negotiation language that gets you paid without getting bounced.
Special Guest:
Madeline Mann
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc
Aaron Calafato
Listen to Aaron's 7 Minute Stories Podcast
Leah Ova
Follow Leah on TikTok
Editorial:
Brooks Borden
Matt Sunbulli
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
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23:47
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23:47
One Million Missing Jobs, CEO vs Employee Optimism Gap & Vanishing Bosses | TLO Headlines
On this episode of TLO Headlines cohosts Matt Sunbulli and Aaron Calafato dig into last week's historic jobs revision number (1 million fewer jobs), why executives and workers see the economy so differently, and what “span of control” means when your manager has 20+ direct reports. Finally, they wrap with culture (Severance, The Studio) and the rise of chaotic workplace TV as a mirror of the anxiety that today’s professionals feel.
Hosts:
Matt Sunbulli
https://www.linkedin.com/in/sunbulli/
https://www.firstdraft.vc/
Aaron Calafato
https://www.7minutestoriespod.com/
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18:47
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18:47
Job Search Secrets, Interviews, and Confidence | TLO Office Hours
In this bonus episode, TLO co-host Leah Ova sits down with Linda Raynier—career strategist, speaker, and author of the upcoming book The Quiet Achiever: Your Journey to Authentic Confidence. With nearly 1M YouTube subscribers and over 2.6M LinkedIn Learning students, Linda has become a trusted guide for introverted professionals navigating confidence, communication, and leadership. Together they tackle Glassdoor community questions on awkward interviews, social media checks, ghosting, and whether extroverts really have the edge in hiring. Stick around for a rapid-fire segment where Linda shares her most underrated job search tool—and her biggest ick as a recruiter.
Guest
Linda Raynier
Welcome to The Lonely Office, an award-winning podcast about making sense of the increasingly blurry line between work and life, brought to you by Glassdoor. We tackle real workplace stories from anonymous firsthand accounts—job ghosting, the truth behind unlimited PTO, nightmare bosses—and share insider advice on layoffs, severance, negotiations, and career moves. From candidates vaping in interviews to employees fired over free speech, we cover the wild reality of modern jobs. Whether you’re growing your career or simply a jobseeker hunting for an edge, you don’t have to navigate it alone.
TLO is hosted by Matt Sunbulli (serial tech entrepreneur, Founder @ Fishbowl and First Draft AI), Aaron Calafato (Storyteller, Narrative Designer & Content Strategist), and Leah Ova (content creator and advertising executive), with special appearances from industry thought leaders and economists.
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