
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

Feb 8, 2023 • 1h 6min
E16 w/ Sahil Lavingia taking Gumroad off the VC treadmill, increasing pricing was very controversial but ultimately the right move
Discussing weekly tech news & topics w/ experienced venture founders. No investors.
@shl (Pinterest, Gumroad, Flexile)
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)

Feb 1, 2023 • 1h 2min
E15 Fundraising lessons from us who collectively have raised $300M+. Tips / tricks / fake term sheets, everything venture fundraising
Discussing weekly tech news & topics w/ experienced venture founders. No investors.
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)
@berman66 (Nanit, Vowel)

Jan 24, 2023 • 1h
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
Discussing weekly tech news w/ experienced venture founders. No investors.
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)
@JoeFernandez (Klout, Joymode, newco)
@berman66 (Nanit, Vowel)

Jan 18, 2023 • 54min
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
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)

Jan 11, 2023 • 55min
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
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)

Jan 4, 2023 • 50min
E 11 w/ Siqi Chen built Runway because of how much building the operating model @ Sandbox VR sucked, is 5 years of runway insane? operating models are different for today's AI, ML
Discussing weekly tech news w/ experienced venture founders. No investors.
Guest - @blader (Runway, Sandbox VR, Postmates, Hey)
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)
@berman66 (Nanit, Vowel)
Fred Wilsons post discussed - https://avc.com/2023/01/what-will-happen-in-2023/
Tomasz Tunguz post discussed - https://tomtunguz.com/sizing-web3-b2b-market/

4 snips
Dec 28, 2022 • 49min
E 10 w/ William Hockey, Plaid getting their series A term sheet pulled from a tier 1 VC, William buys a bank to build the financial system from the bottom up, founders share everything
Discussing weekly tech news w/ experienced venture founders. No investors.
Guest - @williamhockey (plaid, column)
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)

Dec 21, 2022 • 57min
E 9 w/ Adam Nash, growing up in SV and going through 4 tech cycles, building in the bay vs other cities vs remote, working in fintech before it was fintech
Discussing weekly tech news w/ experienced venture founders. No investors.
Guest - @adamnash (Apple, eBay, Linkedin, EIR at Greylock, Wealthfront, Dropbox, Founder Daffy)
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)
@berman66 (Nanit, Vowel)
@JoeFernandez (Klout, Joymode, newco)

Dec 14, 2022 • 50min
Ep 8 - Our first guest Sara Mauskopf of Winnie, raising VC as a woman, all 5 of us are first borns and need to be CEOs, board dynamics, independent board members, Sara’s windy road building Winnie
Discussing weekly tech news w/ second time venture founders. No investors.
Guest - @sm (Google, Twitter, Postmates, Winnie)
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)
@berman66 (Nanit, Vowel)
@JoeFernandez (Klout, Joymode, newco)

Dec 7, 2022 • 58min
Ep 7 - Taking John Doerr through finding PMF again, AI company raises 500x, Joe shares fake metrics, revenge of the VCs, are investor updates worth it, faustian agreement w/ VC
Discussing weekly tech news w/ second time venture founders. No investors.
@julien (Breather, Practice)
@kevingibbon (Shyp, Airhouse)
@JoeFernandez (Klout, Joymode, newco)