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Day One Diaries

Brian McCaffrey

Real stories from the messy middle of starting up. Each episode, host Brian McCaffrey talks with founders, creators, and changemakers about the highs, lows, and lessons of building something from scratch. No glossy success stories - just honest conversations about what it really takes to leave the safe path, take the leap, and figure it out along the way.

PublishesMonthlyEpisodes9Founded7 months ago
Number of ListenersCategories
EntrepreneurshipCareersBusiness

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Latest Episodes

Tim left a 12-year career in capital markets software to co-found a fintech startup. In this episode, he shares what it was like to build and close the business, and how that chapter propelled him into senior leadership roles across e-commerce and fi... more

YouTube

Manu Ravio didn't set out to become a founder. After roles at Google, in deep tech, and in product leadership, he found himself experimenting with AI and eventually launching Formidable - a platform that turns static website forms into live, intellig... more

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After nearly two decades at Google, Pete McAvoy found himself navigating an unexpected turning point. Instead of rushing back into another corporate role, he chose to experiment.

He explored startup advisory work, tested a short-term agency model, ... more

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Ceysa McKechnie on redefining success as a founder Ceysa McKechnie left a successful corporate career to build her own business - and quickly realised that the old definitions of success no longer applied.

In this episode, we explore what "good" lo... more

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How Edu Became the Leader His Company Needed What does it take to grow from founder to CEO? Edu Gaya opens up about Barner's highs, lows, imposter syndrome, tough decisions, and the resilience required to lead a company through chaos and back to grow... more

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When Tony McGaharan left Google to start his own company, he didn't have a perfect plan, but he knew exactly how he wanted people to feel. That clarity shaped People Playbook, a business built on learning that's purposeful, practical, and playful.

... more

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In this episode, Toju Duke talks about how curiosity led her into the world of AI and how she built expertise and influence inside Google before stepping out to build something of her own. She shares what it takes to find your voice beyond a big bran... more

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From Google to founding a virtual ADHD clinic, Eve shares how she built Agave Health while pregnant, proving there's never a perfect time to chase what matters. A raw, honest conversation about pivots, purpose, and building a business and a family at... more

YouTube

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Day One Diaries launched 7 months ago and published 9 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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