#378 Alison Stewart: The LinkedIn DM That Launched a Startup—Part One
Chief Change Officer™: EnsembleShow Notes
Not all career changes are dramatic. Some are deeply deliberate—and a little serendipitous. In Part One, Alison Stewart, COO of Overalls, walks us through her transition from 10+ years in the financial sector to co-founding a startup she discovered on LinkedIn. With two kids at home and a stable job in a Fortune 100 company, Alison didn’t jump recklessly. Instead, she asked the hard questions: Am I fulfilled? What do I want next? And how much risk am I really willing to take? This episode unpacks what happens when you combine career intuition with operational precision—and how a well-timed DM can change everything.
Key Highlights of Our Interview: From Corporate Climb to Personal Wake-Up Call “Time started blending together during the pandemic. I had to ask: Am I actually happy? Or just coasting in a cycle of constant resets?” The Treadmill of Big Company Life “With every leadership change, we took ten steps back before we moved one forward. I was learning—but I wasn’t growing.” Childhood Moves, Adult Adaptability “Moving five times by age 14 taught me to see change as an opportunity. That mindset still guides me today.” The Pregnancy + Merger Combo “Just weeks before giving birth to my second child, my business unit was sold. The uncertainty could’ve been paralyzing—but I chose to treat it as a new beginning.” Risk—But Not Reckless: Mapping a Smarter Pivot “I didn’t quit cold. I asked: What am I good at? What fulfills me? What can my family support? I gave myself permission to explore—and permission to say no.” The Non-Obvious Job Search Strategy “Instead of applying for jobs I knew I could do, I reverse-engineered what I wanted: values, pace, purpose. I wasn’t chasing a title—I was chasing a fit.” The Moment Overalls Popped Off the Screen “When I read about Overalls, something clicked. I didn’t even know if they were hiring. I just knew I had to reach out.” Why LinkedIn Isn’t Just Noise “It wasn’t a random scroll. I used LinkedIn intentionally—to research, reflect, and eventually connect. That DM changed everything.” Communicating Across Industries “Moving out of insurance meant translating my skill set. I had to show how what I did mapped onto what I wanted to do.” Community + Clarity = Career Confidence “A networking group of MBA alumni helped me spot my own excitement. They said, ‘This one lights you up. Go for it.’ That feedback made all the difference.” ____________________ Connect with us: Host: Vince Chan | Guests: Alison Stewart
--Chief Change Officer-- Change Ambitiously. Outgrow Yourself. Open a World of Expansive Human Intelligence for Transformation Gurus, Black Sheep, Unsung Visionaries & Bold Hearts. EdTech Leadership Awards 2025 Finalist. 20 Million+ All-Time Downloads. 80+ Countries Reached Daily. Global Top 1% Podcast. Top 5 US Business. Top 1 US Careers. >>>180,000+ are outgrowing. Act Today.<<<
More from Chief Change Officer™: Ensemble
Waverly Deutsch doesn’t just coach entrepreneurs—she translates English to English, reframes stories with strategy, and helps even the most logic-trained professionals tap into their conviction. In this three-part series, we walk through her unusual path from consulting to Chicago Booth to founding WyseHeart, her pitch strategy firm.
Waverly Deutsch doesn’t just coach entrepreneurs—she translates English to English, reframes stories with strategy, and helps even the most logic-trained professionals tap into their conviction. In this three-part series, we walk through her unusual path from consulting to Chicago Booth to founding WyseHeart, her pitch strategy firm.
Waverly Deutsch doesn’t just coach entrepreneurs—she translates English to English, reframes stories with strategy, and helps even the most logic-trained professionals tap into their conviction. In this three-part series, we walk through her unusual path from consulting to Chicago Booth to founding WyseHeart, her pitch strategy firm.
In Part Two, Brian opens up about what it really cost him to tell the truth inside a political system built on avoidance. From surviving misinformation attacks to refusing to play nice for the sake of power, he reflects on the risks and responsibilities that come with using your platform when it might backfire. We also hear how he rebuilt after the storm—why starting over matters, and what he’s doing differently this time around.
In Part One, Brian walks us through the pivotal moments that shaped his path—from coming out as a college athlete to confronting power structures as a civil rights lawyer. He shares how being raised by military parents shaped his moral compass, how football taught him about leadership under pressure, and why he believes his queerness has made him a better, sharper advocate. This is the story of a public servant forged in fire—and not afraid to stay loud.