Bobby Pinero - How to successfully execute big, bold, ambitious bets as a startup founder!

Bobby Pinero - How to successfully execute big, bold, ambitious bets as a startup founder!

πŸ‘‰πŸΌ About the Guest:

Bobby Pinero (CEO at Equals) has been an analyst for the past decade. With 8 years at Intercom, building Finance, Analytics, Biz Ops, and several other functions, he built out functions that took the company from $1M ARR and ~20 employees to ~$200M ARR and ~700 employees. 

He then launched Equals in the middle of 2021, raising a total of ~$23M from Kristina Shen at Andreessen Horowitz and David Sacks at Craft Ventures. 

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 the Head of Community + Brand at Threado, building a side project called GuestLab, and runs a newsletter called YC Founder Stories alongside hosting this podcast.

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:

Tune in as Sharath and Bobby Pinero discuss the beauty of spreadsheets, pricing as a founder, and taking big bets as a founder.

πŸ‘‰πŸΌ Timestamps:
  • 00:00: Episode Highlight
  • 00:29: Shoutout to
  • 02:55: Introduction to Bobby Pinero and Equals - next-gen spreadsheets
  • 06:29: The process of leaving corporate to build your own startup
  • 11:55: Bobby's journey as a builder from early-stage startups to starting his own business
  • 16:50: Maintaining courage as a startup founder
  • 20:38: Why building in spreadsheets is Bobby's calling
  • 25:27: Big bets vs small bets when building a startup
  • 27:00: The founding story of Equals
  • 30:28: The impact of raising money on building your product
  • 34:31: How to get customer feedback when building a large product vs MVP
  • 39:14: How Bobby built in public - in an unusual way
  • 42:43: Pricing advice for early-stage startups
  • 50:25: Frameworks for pricing and going freemium
  • 53:51: Finding a niche in a crowded and competitive market
  • 56:34: Finding the sweet spot to build in as a founder
  • 59:57: Raising $6.6M for a seed round at Equals - process, networking, deciding the amount
  • 1:04:11: Scaling Intercom from $1M to $200M
  • 1:09:14: The similarities between Intercom and Equals
  • 1:10:54: Lessons from building Intercom that are important at Equals
  • 1:15:22: What's next for Equals?
  • 1:18:02: How to keep going every single day as a founder
  • 1:22:51: Outro and closing thoughts
πŸ‘‰πŸΌ Resources:
  • Equals:
  • Intercom:
  • Abbey, Business Operations at Equals:
  • "How Freemium Nearly Killed My Business":
πŸ‘‰πŸΌ Where to find Bobby Pinero:
  • Twitter:
  • Equals:
  • Instagram:
  • Linkedin:
πŸ‘‰πŸΌ Where to find Sharath:

Episode Video