Second Time Founders

Second Time Founders

Business EN ↓ 86 episodes

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

Business

Podcast website

podcasters.spotify.com

Latest episode

Jun 10, 2025

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Episodes

E36 What are the core foundations to build PMF? Market conditions separate the wheat from the chaff 06.09.2023

Experienced venture founders talking about topics that can help others. @sm (Winnie)  @berman66 (Nanit, Vowel) @kevingibbon (Shyp, Airhouse) 

E35 Is it a good time to raise a series A or B round yet? People that want their name on the blog post are the worst! PMF is very uncomfortable and may require 10-12 hr days. 29.08.2023

Experienced venture founders talking about topics that can help others. @sm (Winnie)  @kevingibbon (Shyp, Airhouse)

E34 Winnie is profitable! Should a CEO/founder get additional equity grants / salary? 15.08.2023

Experienced venture founders talking about topics that can help others. @sm (Winnie)  @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse) 

E33 Founder Stories - Klout’s success v2 Microsoft’s massive offer then Ballmer leaves 23.06.2023

“Founder Stories” where founders talk through something they went through with other founders @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @JoeFernandez (Klout, Joymode, newco)

E32 Founder Stories - Klout’s success 13.06.2023

“Founder Stories” where founders talk through something they went through with other founders @JoeFernandez (Klout, Joymode, newco) @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse) 

E31 Running a venture company profitable. Chasing new platform shifts? 07.06.2023

Second time venture founders talking about topics that can help others. @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @berman66 (Nanit, Vowel)

E30 Startup hiring practices pt 1, GTM tactics 24.05.2023

Second time venture founders talking about topics that can help others. @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @berman66 (Nanit, Vowel)

E29 The siren song of investors, founder PTSD and common coaching questions 17.05.2023

Second time venture founders talking about topics that can help others. @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse) 

E28 Founder Stories - Shyp’s failure v2 - refusing $13M secondary and private jets 10.05.2023

“Founder Stories” where founders talk through something they went through with other founders @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @JoeFernandez (Klout, Joymode, newco)

E27 Founder Stories - Shyp’s failure 03.05.2023

“Founder Stories” where founders talk through something they went through with other founders @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @JoeFernandez (Klout, Joymode, newco)

E26 - "The best episode ever" 19.04.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @julien (Breather, Practice)  @JoeFernandez (Klout, Joymode, newco) @berman66 (Nanit, Vowel)

E25 WARTIME CEO time! IS YCombinator pushing companies' valuations up a good thing? 12.04.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @berman66 (Nanit, Vowel) @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @JoeFernandez (Klout, Joymode, newco)

E24 w/ Mikael Cho of Unsplash about all the lows grinding to become top 150 sites on the internet 04.04.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @mikaelcho (Unsplash) @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @JoeFernandez (Klout, Joymode, newco)

E23 “HEATED EPISODE”!! talking VC downturn, SVB impact, layoffs, surviving, thriving and learning during downturns 29.03.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @berman66 (Nanit, Vowel)

E22 w/ Joe Thomas (Loom) 3 pivots on 20k of funding until Loom started to get some traction and explode 🚀🚀🚀🚀🚀🚀🚀🚀 22.03.2023

Description: Discussing weekly tech news & topics w/ experienced venture founders. No investors. @yoyo_thomas (Loom) @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)  @berman66 (Nanit, Vowel)

E21 w/ Dan Teran (Managed by Q & Gutter) the on-demand economy hype cycle history (2010-2016) 14.03.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @dpteran (Managed by Q, Gutter) @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse)

E19 w/ guest Amjad Masad (Replit) from Jordan to SV on his journey to create the future of programming and why Peter Thiel doesn’t look at product demos 01.03.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @amasad (Replit, Codecademy) @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse)

E20 w/ guest Laura Behrens Wu (Shippo) 10 year journey from an ecomm store to a shipping API unicorn 01.03.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @LauraBehrensWu (Shippo) @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse)

E18 w/ guest Daryna Kulya (OpenPhone) - how to hire the best people ever and go from $0 to $1M ARR 21.02.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @julien (Breather, Practice) @JoeFernandez (Klout, Joymode, newco) @berman66 (Nanit, Vowel)

E17 Creating Founder and Investor Networks, why they matter and how to do it over your career 15.02.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @julien (Breather, Practice) @JoeFernandez (Klout, Joymode, newco) @kevingibbon (Shyp, Airhouse)

E16 w/ Sahil Lavingia taking Gumroad off the VC treadmill, increasing pricing was very controversial but ultimately the right move 08.02.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @shl (Pinterest, Gumroad, Flexile) @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse)

E15 Fundraising lessons from us who collectively have raised $300M+. Tips / tricks / fake term sheets, everything venture fundraising 01.02.2023

Discussing weekly tech news & topics w/ experienced venture founders. No investors. @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse) @berman66 (Nanit, Vowel)

E 14 w/ the core crew - burnout happens when you are becoming successful and can be crippling, how to notice it, prevent it and get out of it 24.01.2023

Discussing weekly tech news w/ experienced venture founders. No investors. @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse) @JoeFernandez (Klout, Joymode, newco) @berman66 (Nanit, Vowel)

E 13 w/ Sidharth Kakkar started Subscript after selling his last company to solve his xls breaking @ $5M ARR, his new company is fully remote and has no meetings 18.01.2023

Discussing weekly tech news w/ experienced venture founders. No investors. Guest - @sikakkar (Subscript, Freckle Education) @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse) @JoeFernandez (Klout, Joymode, newco) @berman66 (Nanit, Vowel)

E 12 w/ Immad Akhund’s 4th company Mercury has been an “overnight” success, serendipity of living in the bay area (yes still!), making over 300 angel investments 11.01.2023

Discussing weekly tech news w/ experienced venture founders. No investors. Guest - @immad (Mercury, YC Partner, Heyzap, Clickpass) @julien (Breather, Practice) @kevingibbon (Shyp, Airhouse) @berman66 (Nanit, Vowel)

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