Second Time Founders
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)
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Author
Second Time Founders
Category
Podcast website
Latest episode
Jun 10, 2025
Where to listen?
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Episodes
E61 Immad Akhund on founding Mercury, getting it to a unicorn valuation, and how he angel invests as a founder 17.04.2024 46:26
Experienced venture founders talking about topics that can help others. Host @sm (Winnie) Guest @immad (Mercury)
E60 Ronak Trivedi who created UberPOOL then started Pietra to help create brands to meeting Kanye West 27.03.2024 58:57
Hosts @kevingibbon (Shyp, Airhouse) @sm (Winnie)
E59 Peter Kazanjy created the playbook on founder lead sales and how to scale your sales org 19.03.2024 45:48
Hosts @kevingibbon (Shyp, Airhouse)
E58 Siqi Chen’s secrets on how to raise hundreds of millions for your startup 13.03.2024 55:59
@blader (Runway, Sandbox VR, Postmates, Hey) @sm (Winnie) @kevingibbon (Shyp, Airhouse)
E57 BREAKING NEWS w/ Mike Knoop of Zapier announcing AI platform Central w/ Vowel 06.03.2024 50:42
Hosts @berman66 (Vowel, Nanit) @kevingibbon (Shyp, Airhouse) @blader (Runway, Sandbox VR, Postmates, Hey)
E56 w/ with Waseem Daher of Pilot on getting Jeff Bezos to invest in your company, successful exits and billion dollar company ideas 28.02.2024 56:52
Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse)
E55 We reached 50k views last episode! Kevin Gibbon just got a term sheet and explains how brutal it out there. 14.02.2024 52:17
Hosts @sm (Winnie) intro.co/SaraMauskopf @berman66 (Nanit, Vowel) @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse)
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 06.02.2024 55:33
Experienced venture founders talking about topics that can help others. Guest @Raadmobrem (Intro, Lettuce) intro.co/Raadmobrem Hosts @sm (Winnie) intro.co/SaraMauskopf @kevingibbon (Shyp, Airhouse) intro.co/KevinGibbon
E53 w/ 3rd time founder Mike Adams on learnings including AI and choosing to step down from CEO 30.01.2024 56:54
Experienced venture founders talking about topics that can help others. Guest @michaelglena (Degreed, MissionU, Grain) Hosts @berman66 (Nanit, Vowel) @kevingibbon (Shyp, Airhouse)
E52 w/ Box’s @levie on how to take your company to IPO, the future of AI, and his best advice for founders 23.01.2024 49:43
Experienced venture founders talking about topics that can help others. Guest @levie (Box) Hosts @berman66 (Nanit, Vowel) @sm (Winnie) @kevingibbon (Shyp, Airhouse)
E51 Artifact’s death, rabbit r1 + building hardware companies, second+ to market has the real startup advantage 16.01.2024 55:01
Experienced venture founders talking about topics that can help others. Hosts @blader (Runway, Sandbox VR, Postmates, Hey) @berman66 (Nanit, Vowel) @kevingibbon (Shyp, Airhouse)
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. 03.01.2024 56:09
Experienced venture founders talking about topics that can help others. Hosts @sm (Winnie) @berman66 (Nanit, Vowel) @kevingibbon (Shyp, Airhouse)
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 19.12.2023 1:00:57
Experienced venture founders talking about topics that can help others. Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse)
E48 Getting to $100M ARR, cutting your team in half, and 3rd time founder tips with Ryan Denehy from Electric AI 06.12.2023 1:01:20
Experienced venture founders talking about topics that can help others. Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse) Guest @DenehyXXL (Electric)
E47 Someone building in stealth on the pod and why you should or not 29.11.2023 50:21
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)
E46 LATEST ON OPEN AI!! But mostly how boards work for your startups work. 22.11.2023 50:22
Experienced venture founders talking about topics that can help others. Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse) @blader (Runway, Sandbox VR, Postmates, Hey)
E45 Platform risk is real (hello OpenAI), working at big companies suck! Join or start a startup instead 07.11.2023 56:35
Experienced venture founders talking about topics that can help others. Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse)
E44 What we would tell ourselves if we could go back decades + tips on how to integrate AI into your startup 01.11.2023 52:13
Experienced venture founders talking about topics that can help others. Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse) @berman66 (Nanit, Vowel)
E43 Debate! Should you incorporate AI into your startup to raise venture right now? 25.10.2023 1:01:10
Experienced venture founders talking about topics that can help others. Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse)
E42 pivoting from PLG to direct sales, are offsites worth it?, benefits + drawbacks of a remote company 18.10.2023 47:58
Experienced venture founders talking about topics that can help others. Hosts @julien (Breather, Practice) @sm (Winnie) @kevingibbon (Shyp, Airhouse) @blader (Hey, Sandbox VR, Runway)
E41 Getting to PMF is all that matters, ignore all the other startup bullshit 13.10.2023 47:40
Experienced venture founders talking about topics that can help others. Hosts @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse) @berman66 (Nanit, Vowel)
E40 What drives us to create venture backed business 04.10.2023 52:26
Experienced venture founders talking about topics that can help others. Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse) @JoeFernandez (Klout, Joymode, newco)
E39 Is self-care for founders even possible? 27.09.2023 58:13
Experienced venture founders talking about topics that can help others. Guest @EricaDiamond Hosts @sm (Winnie) @kevingibbon (Shyp, Airhouse)
E38 Why founders shouldn’t do YC and other accelerators 20.09.2023 43:07
Experienced venture founders talking about topics that can help others. @sm (Winnie) @berman66 (Nanit, Vowel) https://www.linkedin.com/in/lily-brynes-walla-527b082b/
E37 Can you make more cash as a founder over 20+ years vs being a senior software engineer at Google making $500k+/yr? 12.09.2023 59:49
Experienced venture founders talking about topics that can help others. @sm (Winnie) @kevingibbon (Shyp, Airhouse)
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