Some founder stories rise because they are polished. These rose because they were honest. The Best of Hello Chaos 2025 brings together ten conversations founders listened to, shared, and sent to friends who needed to hear them. From legacy driven tech and practical AI to hospitality, accessibility, product design, mental health, and brand building, these founders showed what it actually looks like to build in the messy middle. Across industries and backgrounds, one truth stayed consistent. Chaos is not something to escape. It is something to work through. These stories mattered because they met founders where they are and reminded them why they keep building.
Key Takeaways
1️⃣ Founders who last think past the next win
The most shared stories came from builders focused on legacy, clarity, and long term value instead of quick growth. Across every industry, thinking beyond the next milestone changed how these businesses scaled.
2️⃣ Human centered businesses scale further
From accessibility and hospitality to mental health and community, these founders proved that putting people first drives real growth. Empathy was not a soft value. It was a competitive advantage.
3️⃣ Chaos does not go away. Founders build through it
None of these journeys were clean or linear. The founders who resonated most learned how to keep moving forward while uncertainty was still present.
Timestamps
00:00 - Welcome to the Best of 2025
00:43 - Why these episodes mattered
01:11 - Geoff Weber and building legacy through tech
02:09 - Nathan Freystaetter and practical AI for founders
02:38 - Vickie Zambrano and hospitality as community
03:36 - Angela Fowler and accessibility as growth
04:27 - Erika Giuggio and product obsession
04:55 - Mallory Vaughan Patton and brand timing
05:24 - Katie Krimitsos and mental health leadership
05:51 - Jeffrey Lyon and human centered cybersecurity
06:47 - Dr. Emily Guarnotta and leadership pressure
07:16 - Ryan Provost and reimagining alcohol logistics
07:45 - What these stories taught founders
08:14 - Closing reflections on chaos