The Undefeated Underdogs

Brendan Mahony - Why founders should look at building startups as a game and not a business!


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Oct 30 2024 52 mins  
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👉🏼 About the Guest:

Brendan Mahony is the founder of Sunset, a company that helps tech companies shut down, saving founders thousands of dollars and hundreds of hours. He is also the ex-founder of Toybox (YC S18, acquired) and Contrast (shut down). From this experience, he built Sunset!

👉🏼 About the Host:

Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show.

👉🏼 Sponsor Corner:

Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/



👉🏼 Description:

Listen in as Sharath and Brendan discuss raising money, finding customers at an early stage, weird startup ideas, and more!

👉🏼 Timestamps:

  • 00:00: Episode Highlight
  • 00:22: Shoutout to Acquire.com
  • 02:47: Introduction to Brendan Mahony - founder of Sunset, a startup helping you shut down your startup correctly
  • 04:33: Why create a startup about shutting down startups
  • 10:00: How Brendan raised money as a first-time founder
  • 19:05: How to get investors on board for your startup
  • 20:50: Finding customers as an early-stage startup
  • 25:20: Lessons from the first year of building Sunset
  • 27:20: Building a startup at Y Combinator
  • 32:34: How to bend the rules when you're in founder mode
  • 38:16: How to deal with shutting down your startup - operationally, physically, mentally, emotionally
  • 42:12: What would Brendan work on if not Sunset?
  • 46:00: Weird startup ideas
  • 48:25: Problems startups deal with
  • 50:47: Outro and closing thoughts

👉🏼 Resources:

👉🏼 Where to find Brendan:

  • Twitter: https://x.com/bmaho2211
  • Linkedin: https://www.linkedin.com/in/brendan-mahony-72929385
  • Sunset: https://www.sunsethq.com/

👉🏼 Where to find Sharath:

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