Leadership Journeys [248] - Ryan Howsam -"With Structure And The Right Direction, Success Becomes Inevitable." Choosing Leadership With Sumit Gupta podcast

Leadership Journeys [248] - Ryan Howsam -"With structure and the right direction, success becomes inevitable."

6d ago 38:29

Content provided by Sumit Gupta. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Sumit Gupta or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

This is the Leadership Journey series on the Choosing Leadership Podcast.

I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name.

Ryan Howsam’s entrepreneurial journey is a masterclass in resilience, focus, and bold decision-making.

In this candid conversation on the Choosing Leadership podcast, Ryan shares how he rebuilt his life after a crushing business collapse, turning setbacks into stepping stones.

He reveals the lessons behind scaling Staysure, building teams that thrive without you, and why health and mindfulness are just as critical as strategy.

This isn’t just a success story—it’s a roadmap for leaders who want to stay sharp, avoid burnout, and create lasting impact.

If you’ve ever wondered how to turn adversity into your greatest advantage, this episode is for you.

You can find Ryan Howsam at the below links

In the interview, Ryan shares

"Leadership isn’t about content—it’s about choosing a context that drives bold decisions."
"Resilience is built when you’re knocking on doors, not when everything is going your way."
"A financial collapse taught me more about risk than any business school ever could."
"Focus on mastering one thing—people underestimate what they can achieve in ten years."
"Money doesn’t make you successful; learning to manage it does."
"A great business is one that doesn’t fall apart when you step away."
"Health isn’t optional for leaders—your body is the engine of your ambition."
"Scaling is about empowering capable leaders, not clinging to control."
"Setbacks aren’t failures—they’re invitations to rebuild stronger and smarter."
"The future of entrepreneurship will be fueled by AI and human resilience working together."

287 episodes