Day One Diaries

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.

What Good Looks Like with Ceysa McKechnie 01/14/2026

What Good Looks Like with Ceysa McKechnie 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” looks like after corporate: letting go of constant productivity, working within real capacity, and redefining success in a way that supports both the business and the person behind it. /episode/index/show/d48a4b6a-04f7-4eec-ace0-8d7ab593d328/id/39671690

Becoming The CEO with Edu Gaya 12/10/2025

Becoming The CEO with Edu Gaya How Edu Became the Leader His Company Needed What does it take to grow from founder to CEO? Edu Gaya opens up about highs, lows, imposter syndrome, tough decisions, and the resilience required to lead a company through chaos and back to growth. To find out more about Edu's business, visit https://barnerbrand.com/ /episode/index/show/d48a4b6a-04f7-4eec-ace0-8d7ab593d328/id/39290335

Purposeful, Practical, Playful with Tony McGaharan 11/19/2025

Purposeful, Practical, Playful with Tony McGaharan 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. In this conversation, Tony shares how he turned early setbacks like COVID into opportunity, and how he learned to build a company that could thrive without him. To learn more about Tony's work - check out /episode/index/show/d48a4b6a-04f7-4eec-ace0-8d7ab593d328/id/39022585

Beyond The Badge with Toju Duke 11/02/2025

Beyond The Badge with Toju Duke 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 brand and the mindset needed to keep going when certainty disappears. To learn more about Toju's work - check out www.tojuduke.com/ /episode/index/show/d48a4b6a-04f7-4eec-ace0-8d7ab593d328/id/38882650

No Perfect Time, with Eve Lise Mamane 10/21/2025

No Perfect Time, with Eve Lise Mamane 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 once. For more on Agave Health, visit www.agavehealth.com Subscribe to Day One Diaries for more great founder stories. /episode/index/show/d48a4b6a-04f7-4eec-ace0-8d7ab593d328/id/38725370

Fire Yourself Often with Shiv Gupta 10/03/2025

Fire Yourself Often with Shiv Gupta Shiv Gupta left a safe career in ad tech to start U of Digital, a training company helping the industry keep up with constant change. In this episode of Day One Diaries, Shiv shares how he focused hard from day one, learned to ignore distractions, and why his rule is to “fire yourself often”, stepping aside each year to take on the next challenge. Check out to learn more about U of Digital can do for you. /episode/index/show/d48a4b6a-04f7-4eec-ace0-8d7ab593d328/id/38456720

Day One Diaries

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