$500M Founder: Avoid These Critical Mistakes When Competing With Incumbents - A convo w/ Daniel Simon, Coast CEO episode artwork

EPISODE · Sep 16, 2025 · 34 MIN

$500M Founder: Avoid These Critical Mistakes When Competing With Incumbents - A convo w/ Daniel Simon, Coast CEO

from The IO Podcast: Investor + Operator

Are you a small startup trying to compete with the big dogs? Well then this episode is for you.Tyler and Sterling sit down with Daniel Simon, co-founder of Bread (sold for $500M) who is now working on his next big startup: Coast, a fuel card and payment platform for companies that manage large fleets of vehicles.Daniel breaks down his learnings from his time at Bread, what he's doing differently now at Coast, and the important lessons he's learned from building successful companies in niches that are already dominated by large incumbents.Subscribe to never miss an episode!Chapters:(00:00:00) Intro(00:02:09) Disrupting Fleet-Centric Financial Services(00:05:20) Different vs. Better when competing with Incumbents(00:10:14) Customer Feedback for Product Innovation(00:16:34) Finding Partners for Capital Acquisition(00:21:07) How to Fundraise Effectively(00:24:03) Attracting Investors(00:26:38) Iterative Product Development through Sales Feedback--Check out Coast: coastpay.comThis episode was brought to you by Pelion, a VC firm based in Utah. Learn more about them here: pelionvp.com

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$500M Founder: Avoid These Critical Mistakes When Competing With Incumbents - A convo w/ Daniel Simon, Coast CEO

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