The Undefeated Underdogs

Andrew Rea - Why first-time founders should invest time and effort in building conviction!


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Aug 29 2024 63 mins   1
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👉🏼 About the Guest:

Andrew Rea is the founder of TaxWire which automates SaaS sales tax compliance across your finance stack. He accidentally started Taxwire when he was doing fractional work. Previously he played key roles and led growth at On Deck and Party Round. He also built and sold an EV company that made golf carts.


👉🏼 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 22,000 using give-first principles and creating high-value content. Currently, he is building a SaaS product called GuestLab, and runs another podcast series called YC Founder Stories alongside hosting this one, as well as running Founder Gigs, a resource to discover flexible gigs while building your dream business.

👉🏼 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/

This episode is brought to you by Sunset. They handle all the legal, tax, and operational burdens when shutting down — making sure founders and investors avoid penalties, reduce liabilities, and immediately move on to what's next. If you're interested in learning more, visit sunsethq.com to meet with a representative for their team. And make sure to mention the Undefeated Underdogs Podcast to get $2K off of your dissolution.



👉🏼 Description:

Listen in as Sharath and Andrew discuss building health, conviction in yourself as a founder, and more!

👉🏼 Timestamps:

  • 00:00: Episode Highlight
  • 00:34: Shoutout to Acquire.com and Sunset
  • 03:50: Introduction to Andrew Rea - founder of Taxwire and fan of rotisserie chicken
  • 05:38 Why Andrew is a fan of rotisserie chicken
  • 12:50: Why founders need conviction
  • 22:40: The first breakthrough for Andrea and his transition to being a founder
  • 31:06: Why we need to take more bets on people
  • 38:45: When founders should focus on growth
  • 45:20: Patterns of unconventional growth at startups
  • 49:25: How to find the problem only you can solve
  • 59:23: Why you should or should not apply to an accelerator
  • 1:01:08: Why founders should pay attention to boring problems
  • 1:07:06: Outro and closing thoughts

👉🏼 Resources:

  • Link to Acquire.com: https://try.acquire.com/sharath/
  • Link to Sunset: https://www.sunsethq.com
  • Regina G. - https://www.linkedin.com/in/rpgbx
  • Capital: https://capital.xyz/

👉🏼 Where to find Andrew:

  • Twitter: https://x.com/andrew__rea
  • Linkedin: https://www.linkedin.com/in/andrewrea1996/
  • Newsletter and Blog: https://blog.andrewrea.xyz/

👉🏼 Where to find Sharath:

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