Ep 36. When Your Sail Tears: Resilience in Business with Shelby Hacala
Ever feel like running a business is like sailing in unpredictable waters? For entrepreneurs and leaders, the journey is full of unexpected turns, but that’s where growth happens.
In this episode, Shelby Hacala, seasoned entrepreneur and passionate sailor, shares how lessons from the open sea, adaptation, resilience, teamwork, and strategic thinking, directly apply to running and growing your business.
What you’ll gain:
- Navigating uncertainty
- Preparing your business for sale: right buyer, ensuring “cash is king,” and creating systems
- Protecting your vitality while leading a team
- Real-life stories from Shelby’s personal journey, showing how resilience and adaptability win in both sailing and business
Whether you’re scaling, pivoting, or planning an exit, this conversation offers practical guidance and inspiration to help you steer your business, and your life, toward lasting success.
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Shelby Hacala is a seasoned entrepreneur, certified business coach, and co-founder of BOS360 Business Operating System.
For over 25 years, he has guided leadership teams and C-Suite executives across North America to find clarity, alignment, and lasting success.
Shelby’s entrepreneurial journey began in his twenties, when he founded and grew four companies, including one he successfully sold to a global aerospace firm.
Through YPO and EO, Shelby discovered his passion for coaching and quickly became a Certified Forum Facilitator. In 2014, he retired from aerospace and devoted himself fully to coaching, eventually leading more than 600 sessions as a Certified EOS Implementer.
By 2021, Shelby recognized the need for a more adaptive approach to today’s fast-changing business environment, which led him to co-found BOS360.
Today, Shelby helps entrepreneurs and leadership teams chart their course with clarity, execute with confidence, and thrive in even the most uncertain conditions, bringing the same resilience, adaptability, and teamwork he’s mastered as an ocean sailor.
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0:00 — Cold open: Shelby on sailing and business parallels
2:15 — Meeting Shelby at MMT and the shared love of the water
5:10 — Why sailing is the perfect metaphor for leadership
8:45 — What business leaders can learn about resilience from the open sea
12:20 — Shelby’s entrepreneurial journey: four companies and a global sale
16:05 — Discovering his passion for coaching through YPO & EO
20:30 — Lessons from leading 600+ EOS sessions with leadership teams
24:00 — Why Shelby co-founded BOS360 and how it evolved from EOS
28:40 — The must-haves when preparing your business for sale
32:00 — How leaders can protect their vitality and mental clarity
35:30 — Shelby’s final advice: adaptability wins in sailing and in business