Second Time Founders

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

Second Time Founders


    • May 2, 2025 LATEST EPISODE
    • monthly NEW EPISODES
    • 54m AVG DURATION
    • 84 EPISODES


    Search for episodes from Second Time Founders with a specific topic:

    Latest episodes from Second Time Founders

    E84 The Rise and Sudden Fall of DEI: Why Startups Are Pivoting Now

    Play Episode Listen Later May 2, 2025 47:21


    @sm (Winnie)@kevingibbon (Shyp, Airhouse, Cytronic)

    startups pivoting shyp airhouse
    E82 Corporate Espionage & AI Takeover: Why Startup Competition Just Got CRAZIER

    Play Episode Listen Later Apr 23, 2025 49:47


    @sm (Winnie)@kevingibbon (Shyp, Airhouse, Cytronic)

    startups competition takeover crazier corporate espionage shyp airhouse
    E82 LinkedIn is the New Press? Going Viral Without Media

    Play Episode Listen Later Mar 13, 2025 48:54


    @sm (Winnie)@kevingibbon (Shyp, Airhouse, Cytronic)

    media going viral new press shyp airhouse
    E81 AI Is Changing Everything for Startups—Legal Fights to Daily Life

    Play Episode Listen Later Feb 26, 2025 48:51


    @sm (Winnie)@kevingibbon (Shyp, Airhouse, Cytronic)

    startups legal fights daily life changing everything shyp airhouse
    E80 The Death of Lean Startups? Why AI Makes Startups Harder, Not Easier

    Play Episode Listen Later Feb 5, 2025 48:00


    @sm (Winnie) @kevingibbon (Shyp, Airhouse, Cytronic)

    death easier harder lean startups shyp airhouse
    E79 Why Airhouse Failed—and How Cytronic Will Win

    Play Episode Listen Later Jan 22, 2025 54:55


    Guest @valdarin (Symantec, Sighten, Airhouse, @cytronic_ai (new!)) Hosts @kevingibbon (Shyp, Airhouse, @cytronic_ai (new!))

    hosts failed symantec shyp airhouse
    E78 Slow Ventures' Will's on what it takes to be the best venture startup

    Play Episode Listen Later Jan 15, 2025 51:09


    Guest @wquist (Slow Ventures) Hosts @kevingibbon (Shyp, Airhouse, something new) @berman66 (Nanit, Vowel, something new?)

    startups vowel slow ventures shyp airhouse
    E77 How Founders should Use AI from Microsoft Copilot Product lead Raj

    Play Episode Listen Later Jan 13, 2025 54:40


    Guest @rajrikhy (Salesforce, AppDirect, bitnami, IBM, Microsoft (CoPilot) Hosts @kevingibbon (Shyp, Airhouse, something new) @sm (Winnie)

    founders ibm salesforce use ai microsoft copilot product lead shyp appdirect airhouse
    E76 8VC's Alex Spotted AI & Defense Trends Early | Founders, Motivation & VC Strategies Revealed

    Play Episode Listen Later Dec 18, 2024 43:28


    Guest @AlexKolicich (8VC, Palantir, Clarium, Google, Waterloo) Hosts @immad (Mercury, YC, Heyzap) @kevingibbon (Shyp, Airhouse, something new) @julien (Breather, Practice) 

    founders google strategy practice motivation defense revealed mercury spotted palantir yc breather shyp heyzap airhouse
    E75 AI vs Junior Engineers and CEO Safety Tips

    Play Episode Listen Later Dec 11, 2024 44:59


    Hosts @kevingibbon (Shyp, Airhouse, something new) @sm (Winnie)

    hosts engineers safety tips shyp airhouse
    E74 Founders: Pay yourself.

    Play Episode Listen Later Nov 22, 2024 48:02


    Hosts @kevingibbon (Shyp, Airhouse) @sm (Winnie)

    founders dreams startups hurt hosts mortgage salary skipping startup life shyp airhouse
    E73 What this election means for your startup, how you can use AI where incumbents can't, Notebook LM has superpowers

    Play Episode Listen Later Oct 30, 2024 36:59


    Hosts @kevingibbon (Shyp, Airhouse) @sm (Winnie)

    elections startups hosts superpowers notebook use ai incumbents shyp airhouse
    E72 Company in under invested space hits $1B in revenue while only raising $10M! evaluating AI tools now and how you should use them in your startup

    Play Episode Listen Later Oct 16, 2024 49:23


    Hosts @kevingibbon (Shyp, Airhouse) @sm (Winnie)

    space tools startups raising hits hosts revenue evaluating invested shyp airhouse
    E71 Founders should prioritize themselves higher than anyone else in their company, are VC events worth it?

    Play Episode Listen Later Oct 9, 2024 49:17


    Hosts @kevingibbon (Shyp, Airhouse) @sm (Winnie)

    founders events hosts prioritize anyone else shyp airhouse
    E70 Joe Fernandez shares his 2.5 year journey to find growth w/ allUP against LinkedIn

    Play Episode Listen Later Sep 11, 2024 56:29


    Hosts @JoeFernandez (Klout, Joymode, allUP) @kevingibbon (Shyp, Airhouse) @sm (Winnie)

    growth year journey shyp joe fernandez joymode airhouse
    E69 How Siqi's marketing launch of Runway got 1/10th the reach of an Apple launch

    Play Episode Listen Later Jul 26, 2024 46:33


    @blader (Runway, Sandbox VR, Postmates, Hey) @kevingibbon (Shyp, Airhouse)

    apple marketing reach launch runway postmates shyp siqi airhouse
    E68 Delian (Varda Space, Founders Fund) on raising / running a cap-ex heavy company, successful founders look different today, working w/ government agencies

    Play Episode Listen Later Jul 17, 2024 53:22


    Hosts @kevingibbon (Shyp, Airhouse) @berman66 (Vowel, Nanit) @sm (Winnie)

    space running raising hosts capex varda government agencies founders fund vowel delian shyp airhouse
    E67 Different exit paths for startups, Software Developer job posting down 40% pre-covid

    Play Episode Listen Later Jul 3, 2024 50:19


    Hosts @kevingibbon (Shyp, Airhouse) @sm (Winnie)

    covid-19 startups hosts exit paths software developers pre covid job postings shyp airhouse
    E66 Tim Novikoff of Super Teacher making enough money from selling his first company to follow his passion

    Play Episode Listen Later Jun 27, 2024 57:42


    Hosts @kevingibbon (Shyp, Airhouse) @julien (Breather, Practice) 

    passion practice teacher selling hosts breather enough money shyp novikoff airhouse
    E65 Siqi calls out Anthos capital on twitter, founder/vc inappropriate behaviour

    Play Episode Listen Later Jun 12, 2024 56:23


    Hosts @kevingibbon (Shyp, Airhouse) @julien (Breather, Practice)  @sm (Winnie)

    founders practice hosts behaviour inappropriate breather shyp siqi anthos capital airhouse
    E64 Debate about if AI will live up to the hype from founders in the arena

    Play Episode Listen Later Jun 5, 2024 54:23


    With @kevingibbon (Shyp, Airhouse) @berman66 (Vowel, Nanit, Zapier)  @blader (Sandbox VR, Runway) @julien (Breather, Practice)

    founders practice debate hype arena runway zapier live up breather vowel shyp airhouse
    E63 Adam Fishman, instrumental in Lyft's success turned from advisor to interim exec to media empire for Dads

    Play Episode Listen Later May 15, 2024 53:46


    Hosts @kevingibbon (Shyp, Airhouse) @sm (Winnie) @berman66 (Vowel, Nanit) 

    success media empire hosts dads advisor lyft exec instrumental interim fishman vowel shyp airhouse
    E62 Sophia Amoruso on the epic rise (and fall) of Nasty Gal, why founders might consider taking secondary, and now what she's building at TrustFundVC

    Play Episode Listen Later Apr 24, 2024 47:59


    Experienced venture founders talking about topics that can help others. Hosts @blader (Runway, Sandbox VR) @sm (Winnie) Guest @sophiaamoruso (Trust Fund)

    founders epic hosts experienced secondary rise and fall runway trust funds sophia amoruso nasty gal
    E61 Immad Akhund on founding Mercury, getting it to a unicorn valuation, and how he angel invests as a founder

    Play Episode Listen Later Apr 17, 2024 46:26


    Experienced venture founders talking about topics that can help others. Host @sm (Winnie) Guest @immad (Mercury)

    founders unicorns mercury founding experienced valuations invests immad
    E60 Ronak Trivedi who created UberPOOL then started Pietra to help create brands to meeting Kanye West

    Play Episode Listen Later Mar 27, 2024 58:57


    Hosts @kevingibbon (Shyp, Airhouse) @sm (Winnie)

    kanye west started created hosts brands trivedi uber pool ronak shyp airhouse
    E59 Peter Kazanjy created the playbook on founder lead sales and how to scale your sales org

    Play Episode Listen Later Mar 19, 2024 45:48


    Hosts @kevingibbon (Shyp, Airhouse)

    founders sales created scale hosts playbook shyp airhouse
    E58 Siqi Chen's secrets on how to raise hundreds of millions for your startup

    Play Episode Listen Later Mar 13, 2024 55:59


    @blader (Runway, Sandbox VR, Postmates, Hey) @sm (Winnie)  @kevingibbon (Shyp, Airhouse)

    secrets startups raise millions hundreds runway postmates shyp siqi chen airhouse
    E57 BREAKING NEWS w/ Mike Knoop of Zapier announcing AI platform Central w/ Vowel

    Play Episode Listen Later Mar 6, 2024 50:42


    Hosts @berman66 (Vowel, Nanit) @kevingibbon (Shyp, Airhouse) @blader (Runway, Sandbox VR, Postmates, Hey)

    hosts platform breaking news runway zapier postmates vowel shyp mike knoop airhouse
    E56 w/ with Waseem Daher of Pilot on getting Jeff Bezos to invest in your company, successful exits and billion dollar company ideas

    Play Episode Listen Later Feb 28, 2024 56:52


    Hosts @sm (Winnie)  @kevingibbon (Shyp, Airhouse)

    ideas pilot invest hosts jeff bezos daher exits billion dollar company waseem shyp airhouse
    E55 We reached 50k views last episode! Kevin Gibbon just got a term sheet and explains how brutal it out there.

    Play Episode Listen Later Feb 14, 2024 52:17


    Hosts @sm (Winnie) intro.co/SaraMauskopf @berman66 (Nanit, Vowel) @julien (Breather, Practice)  @kevingibbon (Shyp, Airhouse)

    practice hosts views brutal reached breather gibbon vowel term sheet 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

    Play Episode Listen Later Feb 6, 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

    founders money sharing started experienced bier nikita lettuce raad shyp airhouse
    E53 w/ 3rd time founder Mike Adams on learnings including AI and choosing to step down from CEO

    Play Episode Listen Later Jan 30, 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)

    founders experienced learnings step down mike adams vowel degreed shyp missionu airhouse
    E52 w/ Box's @levie on how to take your company to IPO, the future of AI, and his best advice for founders

    Play Episode Listen Later Jan 23, 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)

    founders experienced best advice future of ai vowel levie shyp airhouse
    E51 Artifact's death, rabbit r1 + building hardware companies, second+ to market has the real startup advantage

    Play Episode Listen Later Jan 16, 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)

    death market startups companies hosts advantage rabbit hardware experienced runway postmates artifact vowel rabbit r1 shyp airhouse
    E50 2024 predictions! Everything is

    Play Episode Listen Later Jan 3, 2024 56:09


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

    tech predictions gen z companies hosts lazy venture experienced logistics fold 2024 predictions vowel hype cycle 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

    Play Episode Listen Later Dec 19, 2023 60:57


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

    founders tech press sexy hosts exit perspectives collapse paths experienced layoffs profitability catastrophic hype cycle svb collapse shyp airhouse
    E48 Getting to $100M ARR, cutting your team in half, and 3rd time founder tips with Ryan Denehy from Electric AI

    Play Episode Listen Later Dec 6, 2023 61:20


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

    founders hosts electric cutting experienced 100m arr shyp
    E47 Someone building in stealth on the pod and why you should or not

    Play Episode Listen Later Nov 29, 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)

    hosts experienced stealth racket breather shyp airhouse
    E46 LATEST ON OPEN AI!! But mostly how boards work for your startups work.

    Play Episode Listen Later Nov 22, 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)

    startups hosts openai boards experienced runway postmates shyp airhouse
    E45 Platform risk is real (hello OpenAI), working at big companies suck! Join or start a startup instead

    Play Episode Listen Later Nov 7, 2023 56:35


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

    risk startups hosts platform suck openai experienced big companies shyp airhouse
    E44 What we would tell ourselves if we could go back decades + tips on how to integrate AI into your startup

    Play Episode Listen Later Nov 1, 2023 52:13


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

    startups hosts decades experienced integrate vowel shyp airhouse
    E43 Debate! Should you incorporate AI into your startup to raise venture right now?

    Play Episode Listen Later Oct 25, 2023 61:10


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

    debate startups raise hosts venture experienced incorporate shyp airhouse
    E42 pivoting from PLG to direct sales, are offsites worth it?, benefits + drawbacks of a remote company

    Play Episode Listen Later Oct 18, 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)

    practice benefits hosts remote pivoting experienced runway direct sales drawbacks breather shyp airhouse
    E41 Getting to PMF is all that matters, ignore all the other startup bullshit

    Play Episode Listen Later Oct 13, 2023 47:40


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

    practice startups hosts bullshit experienced breather vowel shyp airhouse
    E40 What drives us to create venture backed business

    Play Episode Listen Later Oct 4, 2023 52:26


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

    hosts drives venture experienced backed shyp joymode
    E39 Is self-care for founders even possible?

    Play Episode Listen Later Sep 27, 2023 58:13


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

    founders self care experienced shyp airhouse
    E38 Why founders shouldn't do YC and other accelerators

    Play Episode Listen Later Sep 20, 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/

    founders experienced accelerators vowel
    E37 Can you make more cash as a founder over 20+ years vs being a senior software engineer at Google making $500k+/yr?

    Play Episode Listen Later Sep 12, 2023 59:49


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

    founders google experienced 500k software engineers senior software engineer shyp airhouse
    E36 What are the core foundations to build PMF? Market conditions separate the wheat from the chaff

    Play Episode Listen Later Sep 6, 2023 57:58


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

    foundations separate experienced wheat market conditions chaff vowel 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.

    Play Episode Listen Later Aug 29, 2023 59:01


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

    raise uncomfortable experienced good time require blog post shyp airhouse
    E34 Winnie is profitable! Should a CEO/founder get additional equity grants / salary?

    Play Episode Listen Later Aug 15, 2023 59:08


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

    founders practice equity profitable salary experienced grants ceo founder breather shyp airhouse

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