My guest for Episode #306 of the My Favorite Mistake podcast is Betsy Pepine, a serial entrepreneur in real estate and the founder of Pepine Realty. Betsy leads a top-producing real estate team consistently recognized by The Wall Street Journal and has built a family of companies that includes a property management firm, title company, real estate school, and a nonprofit.

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She’s also the author of the 2024 book Breaking Boxes: Dismantling the Metaphorical Boxes That Bind Us, which explores the limiting labels and roles we assign ourselves—and how to break free from them.

Betsy’s favorite mistake was starting her brokerage with no clear plan. What began as a solo effort out of her home unexpectedly turned into a team, and eventually a company—but without intentional structure or culture. That all came to a head when her trusted assistant resigned right before a long-overdue family vacation. Her assistant’s honest feedback—about the lack of family, growth, and purpose—was a painful but pivotal wake-up call. Betsy responded not by retreating, but by reading leadership books on her cruise, hiring a coach, and reinventing her company with clear values and a defined mission.

In our conversation, Betsy shares how she rebuilt Pepine Realty around core values like family, impact, and growth. She talks about initiatives like creating a nonprofit to address housing affordability and designing career paths that include a rare salaried-agent model in real estate. We also discuss the power of learning from mistakes—including how her team shares “learnings” each week in a psychologically safe environment that accelerates growth and prevents repeated errors.

Betsy’s story is about far more than real estate—it’s about leadership, self-awareness, and responding to failure with action. Her perspective will resonate with anyone building a team or culture where people feel seen, supported, and inspired to improve.

• What’s your favorite mistake?
• What did your assistant say when she resigned—and how did that become a turning point for you?
• How did you respond to that feedback, and what changes did you make in your business?
• What were the first steps you took to start shaping your company culture?
• Did you create your mission and core values on your own at first?
• How did you define and build a “sense of family” inside your business?
• What inspired you to create a nonprofit—and how does it fit into your overall mission?
• What’s the purpose behind your unique salaried agent role?
• How do you help team members shift roles if they’re not in the right seat?
• What’s the weekly “learnings” segment in your team meeting—and how does it support growth?
• How do you balance encouraging learning from mistakes without being careless?
• Do you use checklists or systems to help prevent mistakes?
• What prompted you to write Breaking Boxes, and what’s the core message of the book?
• How do we recognize when we’re stuck in a metaphorical box—and how do we step out of it?
• What are the main fears that keep people in those boxes?
• Can you share how fear of failure has influenced your thinking over time?
• What does it take to build resilience to change?
• What’s your approach to managing fear of loss—especially status or social connections?
• How did your connection with Barbara Corcoran come about?
• What lessons have you learned from Barbara as a mentor?
• What advice would you give someone thinking of starting a business without a clear plan?
• What do you think are the best reasons for someone to get into real estate?
• How do you view the role of a real estate agent during high-stress life transitions?
• How do you create consistency in values across your family of companies?
• How do you support women reentering society after incarceration—and what’s the deeper “why” behind that work?

My guest for Episode #305 of the My Favorite Mistake podcast is John Willson, Executive Director of SOAR, the world’s premier outdoor adventure program serving youth with ADHD and learning disabilities.

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With over 30 years of experience, John is a passionate advocate for experiential education and life skills development through structured, strengths-based environments. SOAR, which stands for Success Oriented Achievements Realized, supports young people ages 8 to 25 through summer camps, boarding schools, and gap year programs focused on building confidence and resilience.

John’s favorite mistake took place on Mount Katahdin, the northern end of the Appalachian Trail, where he unknowingly summited a false peak in poor weather conditions. Faced with a difficult decision—turn back through a dangerous route he already knew or forge ahead into unknown terrain—he pressed on despite worsening conditions. Although it was arguably the “wrong” decision in the moment, it led to a powerful sense of accomplishment and a safer descent than expected. John describes this as a “happy mistake” that taught him about risk, perseverance, and the sometimes unexpected rewards of pressing forward.

In our conversation, John shares how this philosophy of “failing forward” underpins SOAR’s mission. He explains how their structured programs help kids with ADHD and learning differences build critical life skills, develop self-awareness, and form friendships—often for the first time. We also explore the importance of creating environments where neurodiverse individuals are supported, understood, and encouraged to take safe risks, with a strong network behind them.

John and I also discuss the evolving understanding of ADHD, the challenges of diagnosis, and how labels matter less than building strategies that work. He shares practical advice for parents and adults alike, emphasizing the role of support systems, coaching, and compassion. Whether you’re a parent, educator, or someone navigating your own neurodiversity, this episode offers insights into how mistakes—when supported by reflection and community—can lead to breakthroughs.

• What’s your favorite mistake?
• Is it true that one of your most common mistakes is people misspelling your last name?
• Did you go back and climb Mount Katahdin again on a clearer day?
• What do you mean by “summit fever”?
• If that decision had led to a bad outcome, would it change how you reflect on it?
• What lessons did you take away from that pattern of decision-making?
• What are some ways the SOAR summer camp is tailored for kids with ADHD or learning disabilities?
• How much of the benefit comes from being with other kids who share similar strengths and challenges?
• How does being in that kind of environment help kids feel more accepted?
• How does SOAR help kids who struggle to make friends build relationships?
• When were you diagnosed with ADHD?
• How did that diagnosis shape your connection to SOAR and the work you do?
• How many SOAR staff members also have ADHD, versus being trained to support it?
• What kind of person tends to thrive on your staff?
• What’s your take on people wondering if they have ADHD or if it’s anxiety or something else?
• What matters more—getting a diagnosis or developing the right coping strategies?
• What advice would you give someone recently diagnosed with ADHD—or who suspects they might have it?
• Can you talk about the role of support systems in success for neurodiverse individuals?
• What’s your view on younger people being more open about neurodiversity in the workplace?
• Can you share some practical first steps after receiving an ADHD diagnosis?
• Why is identifying your support network such a crucial part of success?

My guest for Episode #304 of the My Favorite Mistake podcast is Dr. Tia Warrick, a clinical research leader, epidemiologist, author, and entrepreneur who has spent nearly a decade working in the pharmaceutical and biotech industries.

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She’s the founder of Lesous Consulting, a firm dedicated to supporting clinical research professionals and organizations through education, business analytics, and strategic consulting. With a strong academic background—including a doctorate in health science and clinical health education—Dr. Warrick is committed to empowering the next generation of researchers and bringing more awareness to the vast career opportunities within clinical research.

In this episode, Dr. Warrick shares her "favorite mistake"—not speaking up for herself early in her career. She candidly reflects on a time when she took on significantly more responsibilities than her job description called for but hesitated to advocate for a promotion or raise. Her story highlights how staying silent led to missed opportunities and feelings of frustration. But more importantly, she explains how learning to take accountability and find her voice ultimately fueled her confidence, career progression, and entrepreneurial path.

We also explore the broader challenges and opportunities within the clinical research industry, especially for early-career professionals who may not realize the variety of roles available. Dr. Warrick discusses the importance of mentorship, the need for greater visibility into clinical research career paths, and her motivation for writing Burst the Bubble, a book designed to inform and inspire future talent in the pharmaceutical world. She also touches on how she now teaches others to confidently advocate for themselves—whether during salary negotiations or while shaping their career direction.

• What’s your favorite mistake, and what did you learn from it?
• Was your early role as a clinical research coordinator before or after your advanced degrees?
• When did you realize you should have spoken up for yourself sooner?
• Was there a mentor or moment that helped you come to that realization?
• After receiving a small raise, did you try to advocate for more or take another path?
• Do you share this lesson with students or early-career professionals you mentor?
• How do you coach others on negotiating compensation and advocating for themselves?
• Why is it especially important to speak up early in your career?
• What are some misconceptions people have about roles in clinical research?
• How do you raise awareness about the breadth of opportunities in the field?
• How strong is the job outlook in clinical research, and how might AI impact it?
• What was the inspiration behind founding Lesous Consulting?
• What leadership lessons have you learned so far as a new entrepreneur?
• How do you create a culture where people feel safe to speak up and share feedback?
• What does psychological safety look like in your company and classroom?
• Can you tell us about the AI platform you’re developing and how it supports clinical research?