
Second Time Founders
Discussing weekly tech news w/ second time venture founders. No investors.
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)
@berman66 (Nanit, Vowel)
@JoeFernandez (Klout, Joymode, newco)
Latest episodes

4 snips
Feb 28, 2024 • 57min
E56 w/ with Waseem Daher of Pilot on getting Jeff Bezos to invest in your company, successful exits and billion dollar company ideas
Exploring successful exits, billion dollar company ideas, and getting Jeff Bezos to invest. From software updates to accounting, the journey to securing investments, growing followers on LinkedIn, and navigating AI in entrepreneurship. Strategic funding considerations and prioritizing emotional resilience in business challenges.

Feb 14, 2024 • 52min
E55 We reached 50k views last episode! Kevin Gibbon just got a term sheet and explains how brutal it out there.
Kevin Gibbon, entrepreneur with experience at Shyp and Airhouse, discusses fundraising challenges, building FOMO, perceptions of selling to private equity, immersive live sports viewing using VR, a new product, and emerging technologies like virtual reality and cryptocurrency.

10 snips
Feb 6, 2024 • 56min
E54 w/ the founder of Intro Raad Mobrem sharing why he started it, how it works and why Nikita Bier makes so much money on it
Raad Mobrem, founder of Intro and Lettuce, discusses the evolution of his mentorship platform, challenges in reaching industry figures, equity models in networking, valuable investment strategies, and unconventional success stories from the Intro platform.

Jan 30, 2024 • 57min
E53 w/ 3rd time founder Mike Adams on learnings including AI and choosing to step down from CEO
Mike Adams, an experienced venture founder, shares his learnings including AI and stepping down as a CEO. He discusses challenges in the tech industry, antitrust issues in AI, competing in different markets, achieving viral growth, and the difficulties of achieving viral network effect growth in an overfunded environment.

5 snips
Jan 23, 2024 • 50min
E52 w/ Box’s @levie on how to take your company to IPO, the future of AI, and his best advice for founders
Experienced venture founders talking about topics that can help others.
Guest
@levie (Box)
Hosts
@berman66 (Nanit, Vowel)
@sm (Winnie)
@kevingibbon (Shyp, Airhouse)

Jan 16, 2024 • 55min
E51 Artifact’s death, rabbit r1 + building hardware companies, second+ to market has the real startup advantage
Discussion on the emotional rollercoaster of being a founder and the demise of Artifact, speculation on the reasons behind the discontinuation of an app, comparison of algorithmic feeds to social apps, challenges faced by second-time founders and marketing wisdom war stories.

Jan 3, 2024 • 56min
E50 2024 predictions! Everything is 📈.AI hype cycle is “dead”? Logistics tech is next, is Gen Z too lazy? Lots of dead venture companies will fold.
Hosts reflect on their experiences and expectations for the upcoming year. Emphasis on the value of having a unique opinion and not blindly following others. Reminiscing about their experience with the internet in the 1990s. Discussion on the hiring process and the importance of case studies. Predictions for 2024 including AI, inflation, logistics tech. Exploring controversial content monetization and evolving landscape of content consumption.

Dec 19, 2023 • 1h 1min
E49 2023 from a founders perspectives, AI hype cycle, SVB collapse, profitability is sexy, layoffs aren’t catastrophic, tech press has changed, different exit paths
Experienced venture founders talking about topics that can help others.
Hosts
@sm (Winnie)
@kevingibbon (Shyp, Airhouse)

Dec 6, 2023 • 1h 1min
E48 Getting to $100M ARR, cutting your team in half, and 3rd time founder tips with Ryan Denehy from Electric AI
Experienced venture founders talking about topics that can help others.
Hosts
@sm (Winnie)
@kevingibbon (Shyp, Airhouse)
Guest
@DenehyXXL (Electric)

Nov 29, 2023 • 50min
E47 Someone building in stealth on the pod and why you should or not
Experienced venture founders talking about topics that can help others.
Hosts
@sm (Winnie)
@kevingibbon (Shyp, Airhouse)
@julien (Breather, Practice)
Guest
@awwstn (Stealth, Racket.com, Capiche)