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A young attorney finds herself trapped in a workplace where the expectations keep shifting and the finish line keeps moving. Her story mirrors what so many job seekers are facing in 2025: disappearing opportunities, unclear roles, and leadership that prioritizes itself over its people. In this episode, Matt, Aaron, and Leah break down how to recognize these red flags early and how to safeguard your career before you get stuck running someone else’s race.
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
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Matt Sunbulli
Zaid Safe
Aaron Calafato
Layoffs are rising, AI is being blamed, but the data doesn’t agree. Challenger reports the highest October cuts since 2003 with AI as the #2 reason, while Yale’s 33-month BLS analysis finds no real disruption in high-AI-exposure jobs. We break down the confusion, the “AI layoff boomerang,” and why companies still struggle to get actual ROI from AI.
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
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Matt Sunbulli
Zaid Safe
Aaron Calafato
A new trend is spreading through Silicon Valley’s AI startups as job seekers are being sold “hard mode” as a badge of honor. What began as a protest against overwork in China has quietly become a recruitment pitch in America, with some companies normalizing 80-hour weeks as proof of passion and purpose. In this episode, Aaron, Matt, and Leah unpack the rise of the 9-9-6 culture, the strange mix of ideology and ambition driving it, and whether burnout has become the new benchmark for success. Because if working nonstop is the future of innovation, who’s really winning?
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
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Matt Sunbulli
Zaid Safe
Aaron Calafato
Job searches are dragging on longer than ever with endless applications, ghosted interviews. Maybe it’s time to stop waiting for someone to hire you… and start hiring yourself.
This week, TLO cohost and serial entrepreneur Matt Sunbulli shares the mindset and the literal script for turning frustration into a startup idea. We talk about why job hunts have become endurance tests, the rise of accidental entrepreneurs, and what it really takes to make the leap from job seeker to founder.
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
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Matt Sunbulli
Zaid Safe
Aaron Calafato
In a recent memo AT&T's CEO declared the company had “shifted away” from employment elements rooted in loyalty. Chief Correspondent at Business Insider, Aki Ito, breaks down how the employment contract has collapsed and what “strategic loyalty” looks like when the relationship becomes purely transactional.
*Read Aki Ito's article about The Future of Loyalty
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
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Matt Sunbulli
Zaid Safe
Aaron Calafato
Everyone’s using AI. in therapy, at work, even at the doctor’s office. Yet, we still avoid talking about it. AI has become the invisible collaborator behind so much of modern life, but it remains taboo to mention at work and in most public settings. In this episode, we explore the culture lag between private use and public admission and ask: when will saying “I used AI for that” sound as normal as “I used Google”?
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
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Matt Sunbulli
Zaid Safe
Aaron Calafato
What happens when AI makes average work cheap? How do you stay valuable when AI commoditizes the very skills that once made you special? We explore how comparative advantage, a 200-year-old economic idea, explains today’s career dilemma: when to double down on your craft, when to pivot, and how to uncover the strengths machines still can’t copy. Plus, why narrowing your focus might be the most empowering move in an age obsessed with doing everything.
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
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Matt Sunbulli
Zaid Safe
Aaron Calafato
Managers are juggling 20–30 reports, one-on-ones are drive-bys, and "office hours" are replacing mentorship. We unpack whether AI is the accelerant: which tasks it's automating (performance reviews, expense approvals), why public markets love lean orgs, and how to stay visible when your boss is underwater. Playbooks for managing up, narrating your wins, and getting coached in a flat org.
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:
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
Job search support groups are transforming career hunting from a solo struggle into a multiplayer team effort. Phyl Terry, founder of Never Search Alone, joins us to talk about why even Harvard MBAs are joining support groups to crack today's brutal job market, how job search councils work, and the what's ahead for job seekers as AI rewires the market.
Special Guest:
Phyl Terry
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:
Ken Wendt
Senior Audio Engineer:
Ken Wendt
Research:
Zaid Safe
Matt Sunbulli
Aaron Calafato
What role does social media really play in your job hunt? TLO's Leah Ova talks with career coach Janel Abrahami to separate myth from reality, exploring how recruiters view your online footprint, what helps (and what backfires), and why one underrated job search tool might be the best advice you’ll hear this year.
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