The Undefeated Underdogs

πŸ‘‰πŸΌ About the Guest:

James Evans (Princeton alumni, ex-Bain) is the co-founder and CEO of CommandBar, a user assistance platform that makes your software product easier to use. In 3.5yrs, CommandBar is a 7-figure ARR SaaS business, with over 20 million end-users across hundreds of customers like Hashicorp, Freshworks, and Hubspot and has grown to a team of 40 people and raised $24 million.

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 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.

πŸ‘‰πŸΌ Sponsor Corner:

Shoutout to for being the first sponsor of 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 -

πŸ‘‰πŸΌ Description:

Listen in as Sharath and James discuss the No-PM Policy, why popups suck, the secrets of a first-time founder, and more!
πŸ‘‰πŸΌ Timestamps:
  • 00:00: Episode Highlight
  • 01:05: Shoutout to
  • 03:34: Introduction to James Evans – Founder of CommandBar and hater of popups!
  • 04:58: Why are popups so irritating?
  • 08:32: What are ways of grabbing a customer's attention?
  • 14:14: How most startups should be capturing customers
  • 19:30: CommandBar's newest product...or not
  • 26:45: Finding inspiration for your brand
  • 29:58: James' No-PM Policy
  • 34:04: Making UX better
  • 38:49:The hardest parts of building
  • 42:48: Applying to Y Combinator
  • 46:00: How the best founders design products
  • 49:57: Under shared secrets from a first-time founder
  • 52:41: What is the secret of sales?
  • 55:35: The dangers you'll see in sales
  • 57:39: The best type of content strategy for startups
  • 1:02:11: Where CommandBar is going next and how AI is revolutionizing the way we work
  • 1:07:08: What drives James as a founder?
  • 1:10:25: Outro and closing thoughts
πŸ‘‰πŸΌ Resources:
πŸ‘‰πŸΌ Where to find James:
  • Twitter:
  • Linkedin:
  • CommandBar Website:
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!