This Week in Startups

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders, operators, investors, and innovators.

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Every guest on This Week in Startups

888 guests, ranked by how many people never want them back.

1. —
   Dan Senor

   Start-Up Nation Deep Dive with Dan Senor | E1970 · Jun 2024

   0 votes

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2. —
   Dara Khosrowshahi

   Dara Khosrowshahi, Bill Gurley, Brad Gerstner, & Jason Calacanis on Uber's growth and future | E1878 · 2 episodes

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3. —
   Glenn Fogel

   Booking Holdings CEO Glenn Fogel on travel industry trends, M&A, leadership, and more! | E1830 · Oct 2023

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4. —
   Jason Fried

   E1099: Basecamp Co-Founder Jason Fried on building Hey, making email exciting again, Hey vs. Apple & more · Aug 2020

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5. —
   Matt Mullenweg

   Matt Mullenweg on pioneering remote work, investing in open-source, crypto & more | Angel S5 E7 · Mar 2021

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6. —
   Michael Shellenberger

   Apple's new releases, Twitter bots, Didi returns, Bad actors on Binance + Michael Shellenberger's vision for California | E1477 · Jun 2022

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7. —
   Shishir Mehrotra

   Grammarly is now Superhuman! CEO Shishir Mehrotra explains the rebrand | E2201 · 3 episodes

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8. —
   Vlad Tenev

   How Robinhood became a $68B company w/ Vlad Tenev · Mar 2026

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9. —
   Brian Moore

   E1027: Orreco CEO & Founder Dr. Brian Moore built a platform that optimizes performance of elite athletes, shares cutting-edge benefits of blood sampling, biomarkers, inflammation reduction, glucose monitoring & more! · Feb 2020

   0 votes

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10. —
    Joe Thomas

    Best of This Week in Startups: Week of September 21st, 2020 · 2 episodes

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11. —
    Mark Hyman

    Dr. Mark Hyman on Function Health & GLP-1 microdosing | E2334 · Sep 2026

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12. —
    Aaron Levie

    Box CEO Aaron Levie breaks down Box AI and generative AI's impact on business | E1738 · 2 episodes

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13. —
    Adena Hefets

    Self-driving shakeup: TuSimple CEO fired & Argo AI shuts down + Divvy Homes CEO Adena Hefets | E1600 · 2 episodes

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14. —
    Adrian Aoun

    Engineering an AI-powered doctor's office with Forward CEO Adrian Aoun | E1848 · Nov 2023

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15. —
    Alan Chang

    The Wing shuts down, avoiding pitfalls of success + Tesseract Energy's Alan Chang | E1587 · Oct 2022

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16. —
    Albert Wenger

    Evaluating founder ambition, tools vs platforms + USV's Albert Wenger: post-capital world | E1569 · Sep 2022

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17. —
    Alex MacCaw

    E996: Clearbit CEO & Co-founder Alex MacCaw is creating god-mode for marketers with Clearbit X, gives insights on dynamic customer targeting, prioritizing profitability over valuation, GDPR's adverse effect on Facebook & Google, value of aggregated data · Nov 2019

    0 votes

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18. —
    Alex Mather

    E1003: The Athletic CEO & Co-founder Alex Mather is building a paid online sports media publication, shares insights on attracting investors in a seemingly dying industry, managing 500+ remote writers, creating interesting angles through unique coverage & · Nov 2019

    0 votes

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19. —
    Alexandr Wang

    E1005: Scale AI CEO & Co-founder Alexandr Wang creates training data for all AI applications to improve machine learning, shares insights on the future of autonomous vehicles, China's AI advantages over US, importance of humans focusing on higher-value · Nov 2019

    0 votes

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20. —
    Amjad Masad

    AI-Powered Coding & Space Tugboats? Inside the Future of Software & Satellites! | E2099 · 3 episodes

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21. —
    Andrew Dudum

    Hims & Hers CEO Andrew Dudum on the future of healthcare post-COVID, starting a company to SPAC'ing in 36 months | E1181 · Mar 2021

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22. —
    Andrew Farah

    Fundraising | Scaling Your Startup S2 E4 with Density's Andrew Farah and SoleSavy's Dejan Pralica | E1210 · 2 episodes

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23. —
    Andy Rachleff

    Andy Rachleff on SVB, how to evaluate VCs, market pull indicators, Wealthfront, and more | E1699 · 3 episodes

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24. —
    Ankur Nagpal

    Naval's GP, Ankur Nagpal, Breaks Down The Viral "USVC" Fund | E2284 · May 2026

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25. —
    Anton Osika

    Meta's "creepy" new Ray Bans, Beehiiv teams with Discord, AND a visit from Lovable CEO Anton Osika! | E2181 · 2 episodes

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26. —
    Antonio Gracias

    Liquidity Summit Talks: Antonio Gracias and Gavin Baker | E1990 · 2 episodes

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27. —
    Apurva Mehta

    Apurva Mehta and Jack Altman on Sam Altman, CalPERS, and Liquidation Preferences | E1927 · Apr 2024

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28. —
    Arlan Hamilton

    Arlan Hamilton on raising $5M in crowdfunding, empowering & educating underestimated founders | E1205 · 2 episodes

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29. —
    Arthur Mensch

    Why data is the biggest AI bottleneck (feat. Arthur Mensch of Mistral AI) | E2212 · Nov 2025

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30. —
    Arvind Jain

    The future of enterprise search and AI-powered work productivity with Glean's Arvind Jain | E1916 · Mar 2024

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31. —
    Austen Allred

    E1033: News Roundtable! Lambda School CEO Austen Allred & General Catalyst Partner Katherine Boyle on Lambda School controversy, Techlash & late-stage journalism, Robinhood down as Dow jumps & more! · Mar 2020

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32. —
    Ben Gilbert

    Acquired's Ben Gilbert & David Rosenthal on private markets, ZIRP impact, future of Amazon | E1706 · 10 episodes

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33. —
    Bill Clerico

    Momentum investing in VC + Convective Capital's Bill Clerico | E1627 · Dec 2022

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34. —
    Blake Scholl

    Breaking the Sound Barrier with Blake Scholl from Boom Supersonic | E2186 · 2 episodes

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35. —
    Bob Moesta

    Decoding Customer Insights, Trust, and the Jobs-to-be-Done Framework with Bob Moesta | E1943 · May 2024

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36. —
    Brad Feld

    ANGEL: Brad Feld on investing through 3 economic cycles, CEO/investor dynamics, and more | E1660 · 2 episodes

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37. —
    Brad Gerstner

    Reddit communities revolt + Brad Gerstner on state of private and public markets in 2023 | E1761 · 5 episodes

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38. —
    Bradley Tusk

    GoPuff & Fast trimming staff + Bradley Tusk on tech regulation + Glimpse Co-founder Akash Raju | E1424 · 2 episodes

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39. —
    Brian Halligan

    How to calculate "Bottom-up TAM" + Hubspot Co-Founder Brian Halligan on his new climate fund | E1634 · 2 episodes

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40. —
    Brian Singerman

    Founders Fund's Brian Singerman on building a legendary VC firm, "Adapt or Die" and "Ikigai" | E1896 · Feb 2024

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