The IO Podcast: Investor + Operator $500M Founder: Avoid These Critical Mistakes When Competing With Incumbents - A convo w/ Daniel Simon, Coast CEO
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Sep 16, 2025 Daniel Simon, Founder and CEO of Coast, shares invaluable insights from his journey in fintech, notably after co-founding Bread, which sold for $500M. He discusses the key to competing with large incumbents by emphasizing product differentiation and maintaining a mobile-first approach. Daniel also delves into effective fundraising strategies, cultivating relationships with investors, and innovative customer acquisition methods. His passion for revolutionizing financial services shines through as he outlines exciting plans for Coast's future.
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Respect Incumbents' Hidden Strengths
- Incumbents often look ripe for disruption but have deep, entrenched product features and integrations.
- Approach them with humility and respect for the advantages of incumbency when planning competition.
Differentiate By Vertical Focus
- Find a real differentiation rather than trying to be marginally better than incumbents.
- Verticalize the product to force a clear customer choice and create a new category.
Mobile Enables New Fleet Workflows
- Old workflows persist because they were invented before smartphones existed.
- Reimagining data capture (SMS/app) can create fungible cards and better driver authentication.