The Art of Angel Investing: How Tony Wilkins Went from Chrysler Layoff to Financial Freedom

What happens when everything you were told to do stops working — and you have to figure it out at 23? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Tony Wilkins, Northwestern and University of Chicago Booth graduate, longtime angel investor, executive coach, cancer survivor, and author of The Art of Angel Investing. Tony grew up as the oldest of six boys, built his career as an electrical engineer at Chrysler Corporation in 1979, and was laid off after just one year, along with 300 others. At 23, with everything he thought he had figured out suddenly gone, he made a decision that would shape the rest of his life — stop solving for a job and start solving for financial independence. From there, he went on to earn his MBA at Booth, build a career in high-level banking and finance, become a founding member of Hyde Park Angels in Chicago, and invest in early-stage companies like Spot Hero (acquired by Uber), Cameo, and Nutrasense. This conversation is about more than investing. Tony and Trent dig into what it really means to be the CEO of yourself — knowing what you are solving for, being ruthless about what you can control, and letting go of what you can't. Tony shares how the layoff that shattered his plans at 23 was actually the best thing that ever happened to him, why he secretly applied to Harvard Business School nine months into his dream job, and how a mentee half his age gave him one of the most powerful leadership phrases he's ever heard: "I am firm in my mission and flexible in my methods." This episode is a reminder that winners are not people who never face setbacks. Winners are the ones who learn, adjust, lead, and find a way. In This Episode, We Discuss: How getting laid off at 23 became Tony's most important life lesson Why you must know what you are really solving for — not just what you want right now The CEO of your mindset and owning your results completely Being ruthless about what you can control and letting go of everything you can't How to get started as an angel investor — even without Silicon Valley connections The concept of "triumph or tuition" and why every investment teaches you something How change, AI, and the next generation will shape the future of leadership Key Takeaways ✨ Know what you're really solving for It's not enough to want a good job or a big title. Tony asks every client: "What are you really solving for?" Keep asking why — five times if you have to — until you get to the truth beneath the surface answer. ✨ Be the CEO of yourself You are responsible for your results. No one is coming to save you. Tony learned this at 23 when Chrysler cut 300 people without warning. The sooner you take full ownership of your direction, the sooner your life changes. ✨ Be ruthless about what you can control Tony's rule: be ruthless about what you can control and ruthlessly ignore everything you can't. Gravity exists. Corporate layoffs happen. AI is here. Your energy goes toward what you can actually move. ✨ Triumph or tuition — just get in the water You cannot learn to swim from a book. You cannot become an angel investor without writing a check. Every investment either gives you a triumph or pays your tuition. Either way, you are learning. The key is to start. ✨ Firm in your mission, flexible in your methods A young mentee said this to Tony at the end of a coaching call, and it stopped him cold. Your mission is the non-negotiable. How do you get there? That can evolve. The best leaders hold both at once. Resources Mentioned The Art of Angel Investing by Tony Wilkins Hyde Park Angels — Chicago-based angel investing group Spot Hero — parking app, acquired by Uber Cameo — celebrity video platform Nutrasense — glucose monitoring and quantified self-tracking Connect with Tony Wilkins Instagram: @TonyWilkinChicago LinkedIn: Tony Wilkins 76 Connect with Trent M. Clark Trent M. Clark is the CEO of Leadershipity, President of EOS Michigan, a global speaker, former Major League Baseball coach, and the author of Leading Winning Teams. Website: https://www.trentmclark.com/ Leadershipity: https://www.leadershipity.com/ YouTube: https://www.youtube.com/@Leadershipity LinkedIn: https://www.linkedin.com/in/trentmclark/ Facebook: https://www.facebook.com/TrentMClark Instagram: https://www.instagram.com/trentmclark/ Book: Leading Winning Teams — https://leadingwinningteams.trent-clark.com/bookrecording79 Listen & Subscribe Listen to Winners Find A Way every week on YouTube and all major podcast platforms for conversations with leaders, athletes, entrepreneurs, and high performers who know what it means to overcome adversity and keep finding a way.