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

👉🏼 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. 👉🏼 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.👉🏼 Sponsor Corner:Shoutout to Acquire.com 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 - https://try.acquire.com/sharath/👉🏼 Description:Tune in as Sharath and Bobby Pinero discuss the beauty of spreadsheets, pricing as a founder, and taking big bets as a founder.👉🏼 Timestamps:00:00: Episode Highlight00:29: Shoutout to Acquire.com02:55: Introduction to Bobby Pinero and Equals - next-gen spreadsheets06:29: The process of leaving corporate to build your own startup11:55: Bobby's journey as a builder from early-stage startups to starting his own business16:50: Maintaining courage as a startup founder20:38: Why building in spreadsheets is Bobby's calling25:27: Big bets vs small bets when building a startup27:00: The founding story of Equals30:28: The impact of raising money on building your product34:31: How to get customer feedback when building a large product vs MVP39:14: How Bobby built in public - in an unusual way42:43: Pricing advice for early-stage startups50:25: Frameworks for pricing and going freemium53:51: Finding a niche in a crowded and competitive market56:34: Finding the sweet spot to build in as a founder59:57: Raising $6.6M for a seed round at Equals - process, networking, deciding the amount1:04:11: Scaling Intercom from $1M to $200M1:09:14: The similarities between Intercom and Equals1:10:54: Lessons from building Intercom that are important at Equals1:15:22: What's next for Equals?1:18:02: How to keep going every single day as a founder1:22:51: Outro and closing thoughts👉🏼 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/👉🏼 Where to find Bobby Pinero:Twitter: https://twitter.com/bobbypineroEquals: https://wraptext.equals.com/author/bobby/Instagram: https://www.instagram.com/bobby_pinero/Linkedin: https://www.linkedin.com/in/bobbypinero👉🏼 Where to find Sharath:Twitter: https://twitter.com/5harathYouTube: https://www.youtube.com/@5harathWebsite: https://5harath.com/Newsletter: https://5harath.substack.com/