
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

Nov 22, 2023 • 50min
E46 LATEST ON OPEN AI!! But mostly how boards work for your startups work.
Experienced venture founders talking about topics that can help others.
Hosts
@sm (Winnie)
@kevingibbon (Shyp, Airhouse)
@blader (Runway, Sandbox VR, Postmates, Hey)

Nov 7, 2023 • 57min
E45 Platform risk is real (hello OpenAI), working at big companies suck! Join or start a startup instead
Experienced venture founders talking about topics that can help others.
Hosts
@sm (Winnie)
@kevingibbon (Shyp, Airhouse)

Nov 1, 2023 • 52min
E44 What we would tell ourselves if we could go back decades + tips on how to integrate AI into your startup
The podcast explores the potential impact of AI in startups and strategies for integration. The hosts discuss regrets, advice, and the importance of resilience in running a venture-backed company. Lessons learned include the need for a smaller team and focusing on sales. They also highlight the reality of AI companies and the transition to new technologies. Challenges with SQL queries and the importance of understanding programming fundamentals when using AI are also discussed.

Oct 25, 2023 • 1h 1min
E43 Debate! Should you incorporate AI into your startup to raise venture right now?
Speakers discuss their experience at a unique conference in Hawaii, highlighting off-the-record insights. They explore incorporating AI into startups for venture capital funding, emphasizing the importance of pitching unique solutions. The chapter also touches on strategies for startups, including the expansion into banking and the challenges of securing funding.

Oct 18, 2023 • 48min
E42 pivoting from PLG to direct sales, are offsites worth it?, benefits + drawbacks of a remote company
The hosts discuss fundraising challenges and scaling the business, the importance of sustained growth, and finding the right customers. They also explore the challenges of implementing growth strategies in startups, getting early feedback, and the benefits of offsites. Additionally, they discuss choosing the right city for team offsites and the difficulties of fundraising in a market with uncertainty.

Oct 13, 2023 • 48min
E41 Getting to PMF is all that matters, ignore all the other startup bullshit
Experienced venture founders talking about topics that can help others.
Hosts
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)
@berman66 (Nanit, Vowel)

Oct 4, 2023 • 52min
E40 What drives us to create venture backed business
Founders discuss their motivations for starting a venture-backed business, including upbringing, proving oneself, and being in a growth-oriented environment. They also share their experiences of a two hundred million dollar acquisition and the challenges of entrepreneurship. Additionally, they explore clout measurement in the digital landscape and highlight the importance of high-impact individuals for business success.

Sep 27, 2023 • 58min
E39 Is self-care for founders even possible?
Experienced venture founders talking about topics that can help others.
Guest
@EricaDiamond
Hosts
@sm (Winnie)
@kevingibbon (Shyp, Airhouse)

Sep 20, 2023 • 43min
E38 Why founders shouldn’t do YC and other accelerators
The podcast delves into topics such as starting a new business after selling a previous one, personalized registry platforms for parents and organic referral data, joining YPO and building a leadership team, challenges and benefits of building a remote work culture, creating a virtual community, the value of mom friends and supportive communities, and the role of equity and motivation in startups.

Sep 12, 2023 • 60min
E37 Can you make more cash as a founder over 20+ years vs being a senior software engineer at Google making $500k+/yr?
Experienced venture founders talking about topics that can help others.
@sm (Winnie)
@kevingibbon (Shyp, Airhouse)