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.
Day One Diaries
Claim This Podcastby Brian McCaffrey
11 episodes
Updated Daily
Accepts GuestsHas Sponsors
Podcast Overview
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.
Language
🇺🇲
Publishing Since
10/3/2025
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Recent Episodes
June 17, 2026
Back to my Roots with Mantaj Sidhu
<p dir="ltr">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.</p> <p dir="ltr">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.</p> <p> </p>
May 20, 2026
Amateur to Professional with Esther Mogada
<p>From underground fashion shows in Belfast to building a global storytelling business, Esther Mogada shares the messy reality of turning creativity into a profession.</p> <p>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.</p> <p>We also explore storytelling, identity, ambition, motherhood, and why "integration" has become the defining theme of this season of her life.</p>
April 15, 2026
Risk & Return with Tim Byrne
<p>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.</p> <p>We talk about risk, employability, and why taking the leap strengthened his career rather than set it back.</p>
11 total episodes available
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Frequently asked questions
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- What is Day One Diaries?
- How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Information about guest appearances is not available.
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