The Undefeated Underdogs

πŸ‘‰πŸΌ About the Guest:

Ryan Gilbert is the founder of Workspaces, a newsletter with nearly 14K subscribers, $2K MRR, and 45K subscribers on Twitter, all about the desks of creatives around the world, born during the pandemic. Workspaces was acquired by Loops in 2022, where Ryan was Head of Content, and re-acquired by Ryan for $1 in 2024. He has also worked at Product Hunt and has a new newsletter all about the best headlines across the internet, named H1 Gallery.

πŸ‘‰πŸΌ 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.

πŸ‘‰πŸΌ 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/


πŸ‘‰πŸΌ Description:

Listen in as Sharath and Ryan discuss side projects, building a personal brand, curation vs creation, and more!
 
πŸ‘‰πŸΌ Timestamps:
  • 00:00: Episode Highlight
  • 00:38: Shoutout to Acquire.com
  • 03:06: Introduction to Ryan Gilbert - founder of Workspaces
  • 04:41: Curation vs creation and how they're similar
  • 06:35: How to develop taste
  • 11:00: How to build a narrative around your taste
  • 12:02: Current untapped content trends
  • 15:58: The beginning of Workspaces
  • 21:02: How side projects can change your life
  • 22:25: Tactics for growing a newsletter 0 to 1
  • 24:30: Experiments that didn't work for Workspaces
  • 26:47: Improvements that Ryan is planning for Workspaces
  • 28:38: Why sponsorships are harder now
  • 32:08: Running experiments for sponsors
  • 36:52: Ryan's content strategy at Loops - the email platform for SaaS
  • 39:16: Low-cost content tips
  • 40:47: Building a content strategy in 2024
  • 43:54: Current trends people should pay attention to
  • 44:46: How founders can build a personal brand
  • 46:54: Ryan's experience as a new dad
  • 49:46: Outro and closing thoughts
πŸ‘‰πŸΌ Resources:
πŸ‘‰πŸΌ Where to find Ryan:
  • Twitter: https://twitter.com/rjgilbert
  • Website: https://www.workspaces.xyz/
  • Linkedin: https://www.linkedin.com/in/ryang1lbert/
πŸ‘‰πŸΌ Where to find Sharath:

What is The Undefeated Underdogs?

The Undefeated Underdogs is a podcast unpacking the underdog stories you never heard of!

It highlights the underdog mentality and brings authentic conversations with people who play the long game, take action with a chip on their shoulders, and convert obstacles into opportunities!

Buckle up, as I will be bringing some authentic founders, VCs, community builders, and content creators who got underestimated their whole life, and yet they beat the odds and became insanely successful!