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.
From speech anxiety to AI founder
Nico Aguilar went from a debilitating fear of public speaking to building Speeko, an AI speech coach used by hundreds of thousands.
We talk about starting as an outsider, the reality of building a startup, and why sometimes you just have to put yourself out there.
22 Jul 2026
What 11 Founders Taught Me with Brian McCaffrey
After 11 conversations with founders from around the world, it's time to turn the microphone around.
In this special Season One recap, producer Esther Mogada interviews Brian about the biggest lessons to emerge from Day One Diaries. Together they revisit the themes that kept appearing throughout the series: managing risk, overcoming the fear of failure, finding your unfair advantage, building a business with purpose, and balancing entrepreneurship with family life.
Along the way, you'll hear clips from previous guests and discover how these conversations have shaped Brian's own thinking as he continues to build his business.
Whether you've followed every episode or you're discovering Day One Diaries for the first time, this is the perfect place to reflect on the journey so far and a look ahead to what's coming in Season Two.
17 Jun 2026
Back to my Roots with Mantaj Sidhu
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 opportunities come from going back to your roots.
20 May 2026
Amateur to Professional with Esther Mogada
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 transition from passionate creative to professional business owner.
We also explore storytelling, identity, ambition, motherhood, and why "integration" has become the defining theme of this season of her life.
15 Apr 2026
Risk & Return with Tim Byrne
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.
18 Mar 2026
Skip The Playbook with Manu Ravio
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 skipping the playbook can be the smartest move of all.
17 Feb 2026
Experiment, Learn, Return, with Pete McAvoy
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 this episode, we talk about identity after Big Tech, the challenge of articulating your value as a generalist, and what happens when you treat career risk as an experiment rather than a leap.
Not every transition needs to be dramatic.
Sometimes, real progress comes from testing, learning, and making your next move with greater certainty than before.
14 Jan 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.
10 Dec 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 Barner's (https://barnerbrand.com/) 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/
19 Nov 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 www.peopleplaybook.com
2 Nov 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/
21 Oct 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.
3 Oct 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 www.uof.digital (https://www.uof.digital) to learn more about U of Digital can do for you.
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