Uploaded June 2026 | Updated September 2026, 3 hours ago
It’s better to ask forgiveness than permission.
Entrepreneurial leadership requires a frame of mind that embraces failure. Because failure is the fastest way to learn.
Jon Sockell (MBA ‘12) isn’t afraid of failing, and that’s maybe the key component to his success. His leadership philosophy boils down to asking forgiveness rather than permission, a philosophy shaped by a career spent inside fast-moving companies, where planning is important, but action is essential. In this episode with Taiwo Olawehinmi, Jon delves into the leadership lessons he’s learned on trust, avoiding bottlenecks at the top, and leaving people free to swim in their own lane.
Willingness to fail is key, but it’s also about finding your passion. Because when you follow your own interests, everything is more likely to work out in the end. These are ideas that Jon formed after years in the startup trenches, where he also learned that feedback is a gift, and that it’s essential to think deeply about your customer.
If you’re wondering how to build and foster a startup culture that moves forward without fear, and that leads by action rather than academics, this episode is a must listen. Jon offers insight on not only how to embrace failure, but also on how to find a good work-life balance, and why being the first company in any new space is something he’d rather avoid.
This is leadership with intention, reflection, and heart. Listen in!
Remember to subscribe now so you never miss an episode.
Learn more about us: https://business.vanderbilt.edu/
It’s better to ask forgiveness than permission.
Entrepreneurial leadership requires a frame of mind that embraces failure. Because failure is the fastest way to learn.
Jon Sockell (MBA ‘12) isn’t afraid of failing, and that’s maybe the key component to his success. His leadership philosophy boils down to asking forgiveness rather than permission, a philosophy shaped by a career spent inside fast-moving companies, where planning is important, but action is essential. In this episode with Taiwo Olawehinmi, Jon delves into the leadership lessons he’s learned on trust, avoiding bottlenecks at the top, and leaving people free to swim in their own lane.
Willingness to fail is key, but it’s also about finding your passion. Because when you follow your own interests, everything is more likely to work out in the end. These are ideas that Jon formed after years in the startup trenches, where he also learned that feedback is a gift, and that it’s essential to think deeply about your customer.
If you’re wondering how to build and foster a startup culture that moves forward without fear, and that leads by action rather than academics, this episode is a must listen. Jon offers insight on not only how to embrace failure, but also on how to find a good work-life balance, and why being the first company in any new space is something he’d rather avoid.
This is leadership with intention, reflection, and heart. Listen in!
Remember to subscribe now so you never miss an episode.
Learn more about us: https://business.vanderbilt.edu/
