Brian McCaffrey
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.
Author
Brian McCaffrey
Category
Podcast website
Latest episode
Jun 17, 2026
Where to listen?
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Episodes
Back to my Roots with Mantaj Sidhu 17.06.2026 35:31
After five years at Google, Mantaj Sidhu walked away from the perks, the travel, and the security to return home to India and build something of his own. In this episode, Mantaj shares the story behind Gill Organics, a unique farming business built on trust, transparency and clean food. We talk about leaving corporate life, experimenting with business ideas, and why sometimes the best opportunitie...
Amateur to Professional with Esther Mogada 20.05.2026 35:19
From underground fashion shows in Belfast to building a global storytelling business, Esther Mogada shares the messy reality of turning creativity into a profession. In this episode, Esther talks about quitting her part-time job during the pandemic with nothing but a $47 filmmaking course, the insecurity of being self-taught, nearly losing her business after becoming a mother, and the painful tran...
Risk & Return with Tim Byrne 15.04.2026 33:43
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 fintech. We talk about risk, employability, and why taking the leap strengthened his career rather than set it back.
Skip The Playbook with Manu Ravio 18.03.2026 29:22
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, intelligent conversations. In this episode, we talk about not fitting the corporate mold, building under financial pressure, and why starting narrow and skipp...
Experiment, Learn, Return, with Pete McAvoy 17.02.2026 31:32
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, and tried building something on his own. Some things worked. Some didn't. The market proved tougher than expected. But what he gained was clarity. In th...
What Good Looks Like with Ceysa McKechnie 14.01.2026 33:25
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 busi...
Becoming The CEO with Edu Gaya 10.12.2025 36:19
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 growth. To find out more about Edu's business, visit https://barnerbrand.com/
Purposeful, Practical, Playful with Tony McGaharan 19.11.2025 38:15
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 with...
Beyond The Badge with Toju Duke 02.11.2025 35:26
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/
No Perfect Time, with Eve Lise Mamane 21.10.2025 33:08
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.
Fire Yourself Often with Shiv Gupta 03.10.2025 35:00
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 www.uof.digital to learn more about U of...
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