Unstoppable: For leaders who refuse to settle.

Jana Axline
  • 5.0 (20)
  • Business
  • Updated Weekly

What separates leaders who plateau from those who become unstoppable? It isn’t motivation. It isn’t talent. It’s the principles that guide their decisions when the stakes are highest. Unstoppable explores the turning points, hard choices, and first principles behind exceptional leadership. Each episode examines the moment when the outcome was uncertain — when a leader had to make a decision that could change everything. Through candid conversations and strategic breakdowns, we uncover: • the decisions that defined careers • the principles leaders rely on under pressure • the mistakes that reshaped their thinking • the frameworks that guide extraordinary performance Hosted by entrepreneur and strategist Jana, the show blends deep interviews, first-principles thinking, and strategic case studies to reveal how exceptional leaders actually think. Because success isn’t accidental. It’s built on the principles behind the decisions.

  1. 12h ago

    The Risk of Staying in a Career You've Outgrown ft. Drea Lynn

    Send us Fan Mail On this week’s episode, Jana sits down with attorney, former COO, and executive leadership strategist Drea Lynn, who walked away from a successful corporate career at the exact moment when everything seemed to be going right, only to discover that becoming an entrepreneur required her to completely rethink what had made her successful in the first place. Drea takes us back to a moment when she was at the top of her corporate career. She was making more money than she ever had, leading a growing division, and had plenty of opportunity ahead of her. There was no crisis forcing her out. She wasn't unhappy with her company. She simply realized that something inside her had changed. The work that once energized her no longer carried the same sense of purpose, and she began feeling the pull toward something of her own. Even though she had spent her career building businesses for other people and had never considered herself an entrepreneur, she knew it was time to make a leap. What followed was not the smooth transition she had planned. Drea bought a coaching franchise because the structure felt like a safer way to enter entrepreneurship. She prepared financially, created an offboarding plan, and expected to have several months to transition out of her corporate role. Instead, her boss told her that Friday would be her last day. The plan changed immediately. And the challenges were just beginning. This episode breaks down: How to recognize when you've outgrown a successful careerWhy the skills that make you successful in corporate life don't always translate directly to entrepreneurshipHow preparation can reduce risk without eliminating uncertaintyWhy talking to people who have made a similar transition can reveal questions you don't know to askHow authenticity became the key to rebuilding Drea's confidence and growing her business Drea also shares how she initially tried to become what she thought an entrepreneur was supposed to look like, joining networking groups and forcing herself into activities that didn't fit her personality. It wasn't until she stopped trying to be an entrepreneur and started being herself that everything began to change. By analyzing where her first clients actually came from, experimenting with different approaches, and leaning into the relationships and activities she genuinely enjoyed, Drea discovered that her natural strengths were still there. She simply needed to apply them differently. Because at the end of the day, making a career leap isn't just about knowing when to leave. It's about having the courage to trust yourself enough to become who you're meant to be. Where to find Drea:  https://www.linkedin.com/in/drealynn/ https://www.howtosmartquit.com/ Where to find Jana: https://janaaxline.com/ https://www.linkedin.com/in/janaaxline/Instagram: @unstoppableleadersTikTok: @jana_axline

    The Risk of Staying in a Career You've Outgrown ft. Drea Lynn

  2. Sep 23

    The Decision That Saved Tesla and SpaceX

    Send us Fan Mail On this week’s solo episode, Jana explores one of the most consequential decisions of Elon Musk’s career, and the specific trap that even smart, disciplined leaders can fall into when resources run out. In December 2008, Musk was facing a crisis that looked almost impossible to survive. SpaceX had failed three consecutive rocket launches. Tesla was weeks away from missing payroll. The global financial crisis had effectively frozen the capital markets. And Musk had already committed nearly all of his personal fortune to both companies. The advice around him was simple. Pick one. Concentrate everything on the company with the highest probability of survival and let the other one die. But Musk recognized something his advisors were missing. These weren't two versions of the same bet. SpaceX and Tesla were both bets on entirely different futures, and killing either one would permanently close an option that could not easily be rebuilt. This episode breaks down: Why concentration is usually the right strategy, and when it can become the biggest riskThe difference between incremental bets and bets on a completely different futureWhy conviction can become a financing instrument when there is real skin in the gameHow to distinguish reversible pain from irreversible consequencesWhy keeping an option alive is different from simply being afraid to make a decision Jana also introduces a practical framework for recognizing when the traditional advice to "pick a lane" doesn't apply. By separating incremental opportunities from potential regime changes, evaluating what you can and cannot recover from, and identifying the specific signal you're waiting for, you can make better decisions without confusing avoidance with optionality. Because at the end of the day, the hardest decisions aren't always about choosing what to pursue. Sometimes they're about recognizing what you cannot afford to permanently give up. Where to find Jana: https://janaaxline.com/ https://www.linkedin.com/in/janaaxline/Instagram: @unstoppableleadersTikTok: @jana_axline

    The Decision That Saved Tesla and SpaceX

  3. Sep 16

    Why I Gave Up Control of My Own Nonprofit to Make It Bigger ft. Christopher Quigley

    Send us Fan Mail On this week’s episode, Jana sits down with interdisciplinary artist and executive director of Alchemia Art Workshop, Christopher Quigley, whose life changed dramatically after a near-fatal stroke forced him to confront his mortality and rethink what he wanted to leave behind. Christopher takes us back to the events that ultimately led him to create Transformation of Dangerous Spaces. After a woman named Elaine Mosher was murdered by her partner in the small town where Christopher lives, he felt compelled to do something. He initially tried to purchase and renovate the house where she was killed, with the goal of turning it into transitional housing for women leaving abusive relationships. That idea was rejected. But the rejection opened a different door. Instead, Christopher was asked to create a public art and education project focused on men's responsibility in intimate partner violence and gender based violence. What began as a response to one tragedy quickly became something much larger. Christopher realized the problem wasn't confined to one community. It was bigger than him. And that forced him to make a critical decision: keep the project under his own name and maintain complete control, or build an organization with governance, partnerships, accountability, and the ability to survive without him. This episode breaks down: Why understanding your own limitations can make you a stronger leaderThe difference between building something around yourself and building something that can outlive youHow rejection can redirect you toward an even greater opportunityWhy bringing people into the room who know more than you is a leadership advantageHow confronting mortality can change the way you think about purpose and impact Christopher also shares how his stroke in 2023 fundamentally changed the way he sees his life, giving him a renewed sense of urgency to use whatever time he has left to create meaningful change. Rather than seeking fame or recognition, he wants his work to influence people and continue making an impact even when he is no longer there to lead it. He also talks about embracing what he calls a "delusional sense of self-confidence," thinking bigger than seems reasonable, and building projects that create their own gravity by attracting the right people, opportunities, and conversations. Because at the end of the day, leadership isn't about making yourself indispensable. It's about building something that can survive without you. Where to find Christopher: https://www.linkedin.com/company/alchemia-art-workshop/?originalSubdomain=ca https://www.alchemiaartworkshop.org/ Where to find Jana: https://janaaxline.com/ https://www.linkedin.com/in/janaaxline/Instagram: @unstoppableleadersTikTok: @jana_axline

    Why I Gave Up Control of My Own Nonprofit to Make It Bigger ft. Christopher Quigley

  4. Sep 9

    Why Your Business Shouldn't Be Your Life ft. Cameron Herold

    Send us Fan Mail On this week’s episode, Jana sits down with entrepreneur, author, and founder of the COO Alliance, Cameron Herold, who has spent decades building companies, scaling businesses, and helping entrepreneurs create success without allowing their businesses to consume their lives. Cameron takes us back to when he was just 20 years old and made a decision that would shape the rest of his career. While walking through university, he found a flyer promising the opportunity to earn $10,000 by running his own business. He ended up borrowing money from his father, buying a beat-up van, signing a 67-page franchise agreement, and launching a College Pro Painters franchise. He was terrified. But his father gave him advice that stayed with him: there was never a better time to go bankrupt because he had almost nothing to lose. What Cameron didn't understand was just how hard running a business would actually be. He quickly discovered that entrepreneurship wasn't the glamorous lifestyle social media often portrays. It meant long days, financial uncertainty, hiring employees, finding customers, managing operations, and carrying the responsibility of making sure everyone got paid. But it also taught him something that would become central to his philosophy as a business leader. Your job as an entrepreneur isn't to do everything. It's to get results through other people. This episode breaks down: Why entrepreneurship is much harder than it looks from the outsideHow Cameron learned to delegate everything except his areas of geniusWhy protecting your hobbies, relationships, and personal life is essential to building a sustainable businessThe difference between being an entrepreneur and simply owning a businessHow to recognize when your strengths are no longer aligned with the stage of company you're leading Cameron also shares what happened when he became COO of 1 800 GOT JUNK and helped scale the company from $2 million to more than $100 million in revenue, only to eventually be told that he wasn't the right person to take the company to its next stage. That moment forced Cameron to confront how deeply he had allowed the company to become part of his identity. After leaving, he spent months doing almost nothing related to work. He played golf, spent time with his kids, traveled, cooked, and rediscovered the interests that existed outside of his career. That experience ultimately led him to build the business and coaching career he has today. Because at the end of the day, your business isn't supposed to be your entire life. You're here to enjoy the journey. And the death rate is still 100 percent. Where to find Cameron: https://www.linkedin.com/in/cameronherold/ https://cooalliance.com/ https://linktr.ee/cameronheroldWhere to find Jana: https://janaaxline.com/ https://www.linkedin.com/in/janaaxline/Instagram: @unstoppableleadersTikTok: @jana_axline

    Why Your Business Shouldn't Be Your Life ft. Cameron Herold

  5. Sep 2

    How to Rebuild Your Identity After Losing Your Job ft. Sean Pieri

    Send us Fan Mail On this week’s episode, Jana sits down with author and veteran executive Sean Pieri, who spent more than three decades building a successful career in institutional advancement and fundraising before an unexpected job loss forced him to confront a question he had never seriously considered: who are you when your career no longer defines you? Sean takes us back to August 14, 2018, the day he walked into a routine meeting and was handed a severance agreement. Despite strong performance reviews, a recent bonus, and a promising pipeline of future success, his career suddenly changed direction. What followed was more than a job search. It was an identity crisis. After spending decades equating success with job titles, performance, recognition, and climbing the career ladder, Sean struggled to understand what success meant when that ladder suddenly disappeared. It took him years to recognize that the problem wasn't simply finding the next job. He needed to redefine what he was actually climbing toward. That realization led to an unconventional New Year's resolution: call one person from his past every Thursday for an entire year. Fifty-two calls. What started as a personal experiment became a journey of reconnection, self-discovery, and unexpected stories that completely changed how Sean viewed success, relationships, and the life he wanted to build. This episode breaks down: Why losing your career can feel like losing part of your identityHow reconnecting with people from your past can reveal what actually mattersWhy success needs to be defined on your own termsThe difference between climbing the career ladder and building a meaningful lifeHow adversity can force you to discover a version of yourself you never knew existed Sean also shares some of the most powerful lessons he discovered through his 52 Thursdays, including the importance of living while you can, recognizing that tomorrow isn't guaranteed, and understanding that you have the agency to create your own definition of success. Because at the end of the day, success isn't necessarily the next promotion, the next title, or the next rung on the ladder. Sometimes, it's being home for the moments you spent your career climbing past. Where to find Sean:  https://www.linkedin.com/in/sean-pieri/ https://www.seanpieri.com/  Where to find Jana: https://janaaxline.com/ https://www.linkedin.com/in/janaaxline/Instagram: @unstoppableleadersTikTok: @jana_axline

    How to Rebuild Your Identity After Losing Your Job ft. Sean Pieri

  6. Aug 26

    The Decision That Created Nike

    Send us Fan Mail On this week’s solo episode, Jana explores one of the most pivotal decisions in business history, and why the greatest risk isn't always losing what you have. Sometimes it's becoming too dependent on it.  In 1971, Phil Knight had spent seven years building Blue Ribbon Sports into the dominant distributor of Tiger running shoes in the United States. The business was thriving, holding nearly 70 percent of the market. Then he discovered something that changed everything. The Japanese manufacturer supplying every product his company sold was quietly searching for another U.S. distributor. Suddenly, the business that looked successful from the outside was resting on a single relationship that could disappear overnight.  Phil Knight faced an impossible decision. He could protect the relationship that had built his company, or he could begin creating an alternative before he had permission, before he had certainty, and before he even knew if it would work. He chose to build anyway. What started as a defensive move became the foundation of one of the world's most recognizable brands. While Blue Ribbon Sports continued operating, Knight quietly developed a new company, a new logo, a new supply chain, and eventually a new future. That company became Nike.  This episode breaks down:  Why dependency is often the biggest hidden risk in business and leadership  How to recognize single points of failure before they become crises  Why the best time to build your next opportunity is while your current one is still working  The difference between protecting a relationship and creating leverage  How periods of uncertainty can become your greatest window for innovation Jana also shares three practical principles inspired by Phil Knight's decision, including how to identify critical dependencies, build alternatives before they're urgent, and use today's stability to create tomorrow's security.  Because at the end of the day, the strongest businesses aren't built by protecting what already exists. They're built by creating something no one else has the power to take away. Where to find Jana: https://janaaxline.com/ https://www.linkedin.com/in/janaaxline/Instagram: @unstoppableleadersTikTok: @jana_axline

    The Decision That Created Nike

  7. Aug 19

    How to Stay Relevant in the Age of AI ft. Wes Towers

    Send us Fan Mail On this week’s episode, Jana sits down with entrepreneur and founder of Uplift 360, Wes Towers, who spent more than two decades building a successful digital agency before realizing the rise of AI wasn't just another technology trend. It was a turning point that could either make his business obsolete or force it to evolve into something even more valuable.  Wes takes us back to the moment the warning became impossible to ignore. His agency was thriving. Revenue was strong, clients were loyal, and after 20 years in business, everything pointed toward continued success. Then, during a business valuation, he heard something that changed the way he looked at the future. Despite the company's strong financials, the uncertainty surrounding AI had already begun reducing the value of businesses across his industry. For the first time, the threat wasn't theoretical. It was measurable.  Instead of waiting to see what happened, Wes made a decision. He brought his entire team into the conversation, challenged every operating procedure they had built over two decades, experimented with emerging AI tools, and asked a much bigger question than simply how to automate work. Where does human value still matter? That question reshaped the future of the company. Rather than competing with AI, Wes shifted the business toward deeper consulting, stronger client relationships, and a philosophy he calls "human first," using technology to enhance expertise instead of replace it.  This episode breaks down:  Why waiting for certainty is the fastest way to become irrelevant  How to navigate massive industry change without abandoning your strengths  The difference between using AI as a tool and relying on it as a strategy  Why involving your team creates better decisions during periods of change  How putting people first becomes a competitive advantage in an AI-driven world Wes also shares how challenging long-standing processes, embracing small experiments, and freeing himself from day-to-day operations allowed his business to become more profitable than ever while creating space to deliver greater strategic value to clients.  Because at the end of the day, disruption isn't what puts businesses at risk. Standing still is. Where to find Wes:  https://www.linkedin.com/in/westowers/?skipRedirect=true https://uplift360.com.au/ Where to find Jana: https://janaaxline.com/ https://www.linkedin.com/in/janaaxline/Instagram: @unstoppableleadersTikTok: @jana_axline

    How to Stay Relevant in the Age of AI ft. Wes Towers

  8. Aug 12

    What It Takes to Lead the Blue Angels ft. Greg “Boss” Wooldridge

    Send us Fan Mail On this week’s episode, Jana sits down with former three-time commanding officer of the Blue Angels Greg 'Boss' Wooldridge, who was preparing to retire from the Navy when he received an unexpected call that would force him to choose between the future he had planned and a mission that needed him one more time.  Greg takes us back to one of the most consequential decisions of his military career. After leading the Blue Angels twice, he had spent more than two years away from high performance flying and was preparing for civilian life. Then everything changed. The team's commanding officer was unable to continue, and the Navy asked Greg to return for an unprecedented third tour. The opportunity came with enormous uncertainty. He hadn't flown a fighter jet in years. His family would have to relocate. His retirement plans would be delayed. And perhaps most importantly, he would have to earn the trust of an entirely new team in an environment where trust isn't just important. It's the difference between success and catastrophe.  For Greg, the decision wasn't ultimately about flying. It was about service. He knew that saying no wouldn't just change his future. It would impact the 140 men and women whose season depended on someone stepping forward to lead. This episode breaks down:  Why the greatest leadership decisions are driven by service, not status  How trust becomes the foundation for elite team performance  Why opportunities rarely arrive when the timing feels perfect  The power of choosing possibility over self-doubt  How vulnerability and accountability create high-performing cultures Greg also shares the leadership principles he carried beyond the cockpit, from building psychological safety through radical accountability to creating teams where people are free to acknowledge mistakes, learn quickly, and continuously raise their standard of performance.  Because at the end of the day, the greatest leaders aren't remembered for the opportunities they accepted. They're remembered for the people they chose to serve when it mattered most. Where to find Greg:  https://www.linkedin.com/in/greg-boss-wooldridge/https://johnfoleyinc.com/ Where to find Jana: https://janaaxline.com/ https://www.linkedin.com/in/janaaxline/Instagram: @unstoppableleadersTikTok: @jana_axline

    What It Takes to Lead the Blue Angels ft. Greg “Boss” Wooldridge
See All (26)

Ratings & Reviews

5
out of 5
20 Ratings

About

What separates leaders who plateau from those who become unstoppable? It isn’t motivation. It isn’t talent. It’s the principles that guide their decisions when the stakes are highest. Unstoppable explores the turning points, hard choices, and first principles behind exceptional leadership. Each episode examines the moment when the outcome was uncertain — when a leader had to make a decision that could change everything. Through candid conversations and strategic breakdowns, we uncover: • the decisions that defined careers • the principles leaders rely on under pressure • the mistakes that reshaped their thinking • the frameworks that guide extraordinary performance Hosted by entrepreneur and strategist Jana, the show blends deep interviews, first-principles thinking, and strategic case studies to reveal how exceptional leaders actually think. Because success isn’t accidental. It’s built on the principles behind the decisions.

Information