![Leadership Journeys [248] - Ryan Howsam -"With structure and the right direction, success becomes inevitable."](https://img.transistor.fm/4A1LKcjdmVjHZMgabBRhTitDv0pXsawW37k7qdr1Zvw/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8wOWM4/MzEyYzI1ZTQ0ZWI2/ZjMyM2JmZjIxM2Q3/MzkwNy5wbmc.jpg "Leadership Journeys [248] - Ryan Howsam -\"With structure and the right direction, success becomes inevitable.\"")
Leadership Journeys [248] - Ryan Howsam -"With structure and the right direction, success becomes inevitable."
Description
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."
![Leadership Journeys [247] - Jag Dhanda - "Great teams grow from passion, clear vision, and strong communication."](https://img.transistor.fm/RdiPXydzcfIabALXVkcCAEjKjVUxa4cBILb0RcjnOQg/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9iMWFj/NTcyNDExNDZjNTI5/N2EwZjRmNDAyNTMx/NmFlZC5wbmc.jpg "Leadership Journeys [247] - Jag Dhanda - \"Great teams grow from passion, clear vision, and strong communication.\"")
![Leadership Journeys [246] - Tom Gegax - "The consultant said the problem was me—and after cancer, divorce, and a failing business, I was finally ready to hear it."](https://img.transistor.fm/lAfZmrFxMzFagWoFY1FjhOAShtVFt44nIF0EZis1WpU/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS80MzEx/OTM4OWNhNGJjY2U0/NjI0MWUyOTBjZjY5/NWQ0OS5wbmc.jpg "Leadership Journeys [246] - Tom Gegax - \"The consultant said the problem was me—and after cancer, divorce, and a failing business, I was finally ready to hear it.\"")
![Leadership Journeys [245] - Syed Ahmed - "What people wouldn't know around me is i prefer solitude"](https://img.transistor.fm/ZmhcEmdpgOaFyFva-eD4ce81M0BLY20X6SqFo0TViaM/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9iYjkw/ZmNiMzExY2JlMWVi/ZmQxODZhY2MwMWQ1/NTNiYS5wbmc.jpg "Leadership Journeys [245] - Syed Ahmed - \"What people wouldn't know around me is i prefer solitude\"")
![Leadership Journeys [244] - Conor McGowan Smyth - "I have a deep hunger to explore—both the world and my spiritual side."](https://img.transistor.fm/8xAmTkTdD9eWE60sQXznHk4WTjOee9834JKVT0en90g/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8xZGM1/M2Y1OWQ1MTNjMThm/NmVlZDFlOTcxYzQ0/ODMxMC5wbmc.jpg "Leadership Journeys [244] - Conor McGowan Smyth - \"I have a deep hunger to explore—both the world and my spiritual side.\"")
![Leadership Journeys [243] - Gillian-Alexandre Huart - "When I was in Belgium, I was called French. When I was in France, I was called Belgian."](https://img.transistor.fm/bo9sMSvxFRmkLfnBXe5KEWTcv0hSrMjd18U382RVftk/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS83Y2M1/ODM5NDE0ZDEyNjY5/Y2Q0NTBlZWI2MGJk/ODJmMi5wbmc.jpg "Leadership Journeys [243] - Gillian-Alexandre Huart - \"When I was in Belgium, I was called French. When I was in France, I was called Belgian.\"")
![Leadership Journeys [242] - Kahraman Yigit - "The best manager is the one who replaces himself"](https://img.transistor.fm/-goeVUziLCXOJ_KBEeWVxqkNdiaGG2uzjRWbjf2Mq7A/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8xMDVl/MjgyZTNhNTI2NjYy/OWFjNzdlYWIzNWIw/MzEyMi5wbmc.jpg "Leadership Journeys [242] - Kahraman Yigit - \"The best manager is the one who replaces himself\"")
![Leadership Journeys [241] - Zach Smith - "Connection through new cultures or places can spark powerful inner growth."](https://img.transistor.fm/mfYnAQgs35kK1fwUEDrOKhtyRaVdYGdcczd_uG71HLw/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS82NjAw/ZWQyNDdjNTEyYTlh/YWRjODJhZDNkNjM3/MDdkNS5wbmc.jpg "Leadership Journeys [241] - Zach Smith - \"Connection through new cultures or places can spark powerful inner growth.\"")
![Leadership Journeys [240] - Jonne Välilä - "Most things—whether in life or business—just aren't worth the stress."](https://img.transistor.fm/bxt0qCadFEMSAbgTkrWQZkU1GPn22bp_HJyoOEpNZEg/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8xMGE2/YmRlODg0MjIxNGI2/MmVhMzgxNzIzNTQz/YmJhYS5wbmc.jpg "Leadership Journeys [240] - Jonne Välilä - \"Most things—whether in life or business—just aren't worth the stress.\"")
![Leadership Journeys [239] - Steven Meersman - " You can never achieve balance because then you're standing still and you die"](https://img.transistor.fm/9jPa_cyhVaOJiZXD8ap4EV0rMPusWoK3RdESibGuRYs/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8wODgz/NjM1MGE3NDc4ZDVh/YzQ5YWUyODVmMjky/OTAwYy5wbmc.jpg "Leadership Journeys [239] - Steven Meersman - \" You can never achieve balance because then you're standing still and you die\"")
![Leadership Journeys [238] - Saasha Celestial-One - "Every dollar that you spend is a vote for the world that you wanna live in"](https://img.transistor.fm/H_c33kKzNvBbxAukJJm2rvfALHASgx1EJOyh2ScRs2o/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9hOWQw/MThmOTY2YTBjMTM0/MWVlMDE1ODBiZjA5/Yjc4Yi5wbmc.jpg "Leadership Journeys [238] - Saasha Celestial-One - \"Every dollar that you spend is a vote for the world that you wanna live in\"")
![Leadership Journeys [237] - Anant Agarwal - " Sales is vanity. Profit is sanity, and cash is reality. "](https://img.transistor.fm/vxexrYvqejzGqcd_mCt8TligJzFExKvlEN72K8SvKZA/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9jNzMz/MzljMjY2OGVkMTAz/MjVmOGU4Mzc3M2Ni/MzA2My5wbmc.jpg "Leadership Journeys [237] - Anant Agarwal - \" Sales is vanity. Profit is sanity, and cash is reality. \"")
![Leadership Journeys [236] - Jason Foster - "People do their best work when they feel safe to disagree."](https://img.transistor.fm/qgcNAcAVvWHR3LqZ9jDn9Iyrf6nW5qrlI0ceU7PFBtg/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9mMjE5/MDk0ZmQyMWM4Njg2/NDEzZTA0ZTliYTJm/NWZkYy5wbmc.jpg "Leadership Journeys [236] - Jason Foster - \"People do their best work when they feel safe to disagree.\"")
![Leadership Journeys [235] - Jonathan Brun - "Anything valuable and lasting takes time to build."](https://img.transistor.fm/i2b0ZLHYL1nPoTCjKasmajMoUbjeJbwaGI0FnwMwYfQ/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9jN2I3/YTNhYTJlZTU0MTcw/MmQ5NjgyZTIzZGMx/NGMxNS5wbmc.jpg "Leadership Journeys [235] - Jonathan Brun - \"Anything valuable and lasting takes time to build.\"")
![Leadership Journeys [234] - Siddhi Joshi - "Being a CEO & the only female employee was adventurous"](https://img.transistor.fm/I0vp5AS_bOXE8g-Prkxyw3cjV1mFWGqdOmS0m7oagmg/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9lZDNh/OGJlZGFjNGU4N2Nm/ZWY1NDQ5ODlmNzEy/N2ZlNC5wbmc.jpg "Leadership Journeys [234] - Siddhi Joshi - \"Being a CEO & the only female employee was adventurous\"")
![Leadership Journeys [233] - Bidhan Baruah - " I spend 70% of my time in one-on-ones with my teams"](https://img.transistor.fm/KdUf35cYLMjpFpsvxln2N3OFQ0BuGIxTY1PTQhyEX1o/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9kNWUx/MWVjOWM0NDBlODY0/MjdlYWY5ZDgwZDll/NTI2Yi5wbmc.jpg "Leadership Journeys [233] - Bidhan Baruah - \" I spend 70% of my time in one-on-ones with my teams\"")
![Leadership Journeys [232] - Craig Dunham - " You can be direct and transparent without being mean."](https://img.transistor.fm/7A1bw0wHNx6Q01xHC0ZLcHujtTTjqJct_Vw3Amik3us/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS83NDE4/ODE2YzZkOGFkYzNm/OWY1NWMwOGRmMDUz/NDNkNS5wbmc.jpg "Leadership Journeys [232] - Craig Dunham - \" You can be direct and transparent without being mean.\"")
![Leadership Journeys [231] - Crafting a Meaningful Legacy: KK Gupta's Leap into Entrepreneurship](https://img.transistor.fm/fcWFG64xOtliULUF11gGBQ1quCTQ_Xeu_21aCBcG2v0/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8wMTkx/MzVmYzU5MmVhZGE5/NjlhOTJhMGNmYzk1/MTliNy5wbmc.jpg "Leadership Journeys [231] - Crafting a Meaningful Legacy: KK Gupta's Leap into Entrepreneurship")
![Leadership Journeys [230] - Puneet Shivam - "Every critical choice is the beginning of an action set."](https://img.transistor.fm/iV_yjslcI2i6ZXcbxEvgW4NSBEnMdyf7Apd4pJYlDiE/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS80MDNk/OWUyMzk0NTEzYzY2/NzgwY2Q2Yjg4N2Qw/NjIxZC5wbmc.jpg "Leadership Journeys [230] - Puneet Shivam - \"Every critical choice is the beginning of an action set.\"")
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