Trailer | Why Am I Doing This?

Alice Rolli made a truly bold vocational bet in 2023: with no prior experience in elected office, she ran for mayor of Nashville, a major metropolitan city. With an MBA and a background in high growth firms, this was a significant departure, and we talked about her reasons for getting into the race and what she learned along the way. A few insights:1. The person stopping you is probably youI asked her what holds most people back from making a change when they are unhappy. She described what it was like to be outspent 10-to-1 and find a way to keep going. “The big shots can’t elect you, but they can defeat you. If you spend your time listening to people who say you can’t win, you’ll convince yourself never to do it.”2. Imposter syndrome lies about who belongsEarly in the campaign at a public forum, Alice sat on stage with city council members, state senators, candidates writing seven-figure checks. That unhelpful inner voice whispered: I don’t belong here.Her childhood friend watched from the audience, knowing nothing about Nashville politics. After the event she told Alice, “You’re so much more qualified than all these other people.”The encouragement of people close to her, reminding her what she was capable of during times of self doubt, pushed her to keep going and keep taking risks.3. Nine nos get you to one yesShe often heard in early donor pitch meetings: “I’m supporting someone else.” “Come back when you have more traction.” “I don’t think I’m gonna get involved.”Alice borrowed the Mary Kay principle: you need nine nos to get a yes.Her response: “I appreciate your loyalty. Can I be your first second choice?”Three months after former Senate Majority Leader Bill Frist said no, he texted: “I’m going to send you some money. I want to host an event.”The no meant “not today, not “not ever.”4. Public failure is more rewarding than private safetyAfter the election, she felt like she’d let supporters down, all the people who invested hours and money and belief.But then she’d encounter people around the city: strangers at Costco, health clinics, football games. They shared messages like, “I voted for you. Don’t give up.”People admire people who stand up for what they believe in. They don’t reject failure.Now Alice leads the Children's Hospital Alliance of Tennessee, advocating for health policy to support non-profit children's hospitals in the state. It’s a role that opened because she was “very publicly unemployed” and willing to take the leap.5. Operate with singular focusAlice’s husband Michael, a combat veteran, helped her focus by likening the campaign to a combat deployment: “Right now you are deployed. You are not here. You have no responsibilities here [at home]. Go.”It's a worthwhile principle for startups. Companies with founders who have no backup plan get further than those operating with “if this doesn’t work in six weeks, I’ll just drop out.”If you’re stuck where you are, are you operating as if you’re living your backup plan? Where are you hedging?

Entrepreneur Kristen Nicholson left a 22-year corporate career to build Urban Sweat, a luxury wellness studio offering infrared sauna, red light therapy, and cold plunge.The decision built over years. What pushed her over the edge was when in 2022, "I heard three times in one day that I should bet on myself.”She later acquired a multi-site sauna studio and also co-founded Comfort Imaging, a center delivering non-compression, gravity-based breast CT for pain-free, high-clarity imaging. We discuss the emotional rollercoaster of entrepreneurship (why it feels like a cold plunge), the discipline and meaning that replaced her old “safe” paycheck, and how she hires, empowers, and leads. We dig into sleep as a keystone for health, proactive wellness vs. sick-care, and why she’s betting big on a more dignified approach to women’s imaging.Mentions- Urban Sweat — infrared sauna, red light, cold plunge: https://urban-sweat.squarespace.com/    - Comfort Imaging (Breast CT) — non-compression, gravity-based imaging: comfortimagingtn.com    - EO (Entrepreneurs’ Organization) & Catalyst (Nashville Entrepreneur Center) — peer forums & accountability    - The E-Myth Revisited (Michael Gerber) — on working on vs. in the business    - EMDR & binaural beats — mentioned as tools for anxiety regulation and perspective    

If you lead teams in messy, growing companies, you will find refreshing, practical execution wisdom in this interview. We cover the five jobs of leadership, balancing this week vs. the next 90 days, turning field shadowing into product improvements, and keeping your compass true at work and in art.Frazer argues great operators are “born with an operator brain,” but the muscle is honed by doing five jobs relentlessly: hire great people, set strategy, monitor behaviors, measure results, and model culture. He shows how to split attention between the here and now and a 90-day horizon, why iteration beats ideation once you’ve found a promising arc (from ~25% to ~80% maturity), and how to build a culture of risk-free candor so problems surface fast and get fixed. We also dig into his unexpected right-brain practice: making sculpture and canvas works from creek limestones—how “flow” keeps the work and the person honest.Timestamps00:00 – Operator DNA & the 5 jobs of leadership03:00 – Two horizons: this week vs the next 90 days (and how to allocate time)04:30 – KPIs, reviews, and the operating cadence05:30 – Shadowing the field: product fixes you only see on the front line08:00 – Building risk-free candor so problems surface fast11:00 – “No plan survives first contact”—why conference rooms lie13:00 – Shiny objects vs focus; iteration > ideation; the 25% → 80% arc18:00 – ELT composition, offsites, and a living North Star20:00 – Change your environment to think better (and schedule deep work)24:00 – Paper before PowerPoint (story first, slides later)27:00 – Why growth companies > big-company optimization28:30 – Aligning clinicians and business around the patient33:00 – Frazer’s art: limestone sculptures and stone-on-canvas42:00 – Flow state, imposter feelings, and keeping the work honest52:00 – The career funnel & becoming the most prepared candidate55:00 – The three-circle target for a satisfying career56:30 – What’s next in art; where to see his work

An introduction to the podcast.