
Bobby Pinero - How to successfully execute big, bold, ambitious bets as a startup founder!
The Undefeated Underdogs
Discussing Launch and the Qualities of Successful Founders
In this chapter, the speakers discuss the qualities that make founders great and share personal stories of finding strength and courage in pursuing their calling. They emphasize the importance of expressing passion and energy to inspire others.
๐๐ผ 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.
๐๐ผ 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.
๐๐ผ Sponsor Corner:
Shoutout to Acquire.com for being the first sponsor of The Undefeated Underdogs podcast! Theyโre 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/
๐๐ผ Description:
Tune in as Sharath and Bobby Pinero discuss the beauty of spreadsheets, pricing as a founder, and taking big bets as a founder.
๐๐ผ Timestamps:
- 00:00: Episode Highlight
- 00:29: Shoutout to Acquire.com
- 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
๐๐ผ Resources:
- Equals: https://equals.com/
- Intercom: https://www.intercom.com/
- Abbey, Business Operations at Equals: https://www.linkedin.com/in/abbey-minondo/
- "How Freemium Nearly Killed My Business": https://wraptext.equals.com/the-fallacy-of-freemium-in-saas/
๐๐ผ Where to find Bobby Pinero:
- Twitter: https://twitter.com/bobbypinero
- Equals: https://wraptext.equals.com/author/bobby/
- Instagram: https://www.instagram.com/bobby_pinero/
- Linkedin: https://www.linkedin.com/in/bobbypinero
๐๐ผ Where to find Sharath:
- Twitter: https://twitter.com/5harath
- YouTube: https://www.youtube.com/@5harath
- Website: https://5harath.com/
- Newsletter: https://5harath.substack.com/