In this episode of the Startup Ignition Podcast, we sit down with Matt Stapleton, a multi-time founder who recently exited Spiff to Salesforce for nearly $480 million. Matt shares his journey from "dialing for dollars" as a commission-only rep to building and exiting two successful FinTech companies: Capshare and Spiff. We dive deep into the importance of clean cap tables (including a horror story about 16 classes of preferred stock), why the best SaaS ideas are often hidden in manual Excel spreadsheets, and the strategic nuance of taking investment from corporate venture arms. Matt closes the episode with his "2% rule" for productivity that helped him navigate the path from idea to nine-figure exit.


(00:00:00) Introduction and Matt Stapleton’s bio

(00:04:35) Icebreaker: The real reason founders love AI

(00:07:51) Horror Story: The cap table with 16 classes of preferred stock

(00:12:10) Why bad cap table management is securities fraud

(00:16:23) The key to getting acquired: Beginning with the end in mind

(00:19:00) Matt’s background: From finance major to cold calling

(00:30:17) How "dialing for dollars" changed Matt’s career trajectory

(00:34:50) Founding Capshare and competing with Carta

(00:46:17) The first exit: Selling Capshare to Solium/Morgan Stanley

(00:51:28) The genesis of Spiff: Replacing spreadsheets with SaaS

(00:56:48) Why public companies still run critical processes on Excel

(01:01:20) Public vs. Private exits: Valuation multiples and liquidity

(01:05:43) Strategy: Taking investment from Salesforce before the acquisition

(01:08:50) Final Tip: The "2% Rule" and doing the hard things

Learn more about us:
https://startupignition.com/links

Apply to be a guest on the pod:
https://startup-ignition-podcast.paperform.co/

Follow John & Tyler:
https://x.com/trich_
https://www.linkedin.com/in/johnrichards/

Subscribe on YouTube:
https://www.youtube.com/@StartupIgnition

Follow on X:
https://x.com/startupignition

Follow on Instagram:
https://www.instagram.com/startupignition/

Follow on TikTok:
https://www.tiktok.com/@startupignition

Follow on LinkedIn:
https://www.linkedin.com/school/6458758/admin/dashboard/

Follow on Facebook:
https://www.facebook.com/startupignition/

#SaaS
#FinTech
#StartupExit
#Salesforce
#Spiff
#CapTable
#Entrepreneurship
#VentureCapital
#Founders
#BusinessPodcast
#ExitStrategy
#StartupAdvice
#CorporateDev
#SalesCommission
#TechStartups
#AngelInvesting
#StartupIgnition
#UtahTech
#BootstrapToExit
#SaaSFounders