Anything But Typical

Gary Frey & Ben McDonald
  • 5.0 (23)
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Gary Frey & Ben McDonald host round table conversations discussing entrepreneurship, leadership, and success on your own terms.

  1. MAY 19

    169: The Journey of Leadership, Growth, and Culture at One Digital with Mark McLean

    Discover the story of Mark McLean’s impressive journey from early influences to leading a multi-billion-dollar company. Learn how culture, relationships, humility, and strategic growth propel organizations through transitions and challenges.   Main topics: Building a career in insurance and financial services, rooted in mentorship and family lessons Navigating growth: from founding to billion-dollar company, merger, and acquisitions The importance of company culture, relationships, and core values in long-term success Personal resilience through life's challenges including health, family, and entrepreneurial pivots   Timestamps: 00:00 - Defining what takes Mark McLean out in public   00:29 - Interests beyond work: sports, golf, and family   01:54 - The role of sports and family fun in shaping his values   02:40 - Favorite golf locations and social activities   03:10 - Humble introduction and the significance of titles   04:13 - Career overview: from Senior Managing Principal to Senior VP   06:46 - The importance of faith, family, and friendships in reputation   07:49 - The influence of Jeff Warner and mentorship connections   08:42 - Early motivations: lessons from family and mentors   09:30 - Growing up in Florence, South Carolina, and early career influences   11:12 - College journey, changing majors, and love for insurance   12:42 - Industry insights: relationship building, trust, and reputation   15:36 - Industry trends, industry change, and mentorship in risk management   17:45 - Industry challenges, trust, and business growth   20:04 - Licensing, early sales experiences, and building business foundations   22:02 - The role of creativity and relationship management in success   23:11 - Industry evolution and personal insights into trend anticipation   24:46 - Handling life’s challenges, family, and career pivots   25:36 - The importance of good culture and team alignment   27:24 - Transition from employment to entrepreneurship: the leap into owning and growing businesses   32:51 - Building Turnkey Benefits, sale, and subsequent ventures   36:16 - Growth from 25 to 170 employees, industry innovation   40:54 - Navigating partnership changes, relationships, and success   44:11 - Transition into digital organizations, culture, and values   50:46 - Building a unified message, controlling quality and trust   54:45 - Personal experiences: family, loss, and professional resilience   56:55 - Adapting to industry and market changes post-Obamacare   58:26 - Balancing growth, personal life, and company focus   62:22 - About joining One Digital, the corporate culture, and long-term vision   66:00 - The role of private equity, strategic capital, and maintaining independence   70:01 - The secret sauce: company culture as a competitive advantage   73:51 - Leadership values: integrity, humility, and people first   77:08 - The importance of intentional culture, talented leadership, and long-term vision   78:45 - Family, blended families, and parenting insights about nurturing strong values   79:03 - Final thoughts — being discerning, strategic, and building legacy   Resources: Connect with Mark McLean OneDigital

    1h 15m

  2. MAY 5

    168: Embracing Authenticity, Branding, and Referrals with Stacey Brown Randall

    In this episode, Stacey Brown Randall shares her inspiring journey from business failures to becoming a trusted referral expert, emphasizing the importance of authenticity and intentional branding. Discover her tactics for building meaningful relationships, protecting your IP in the age of AI, and shifting the traditional mindset around referrals.   Key topics: Stacey’s entrepreneurial journey: from failed startups to strategic branding The significance of being intentional about brand consistency, especially with signature colors How understanding your “why” fuels resilience through business setbacks Reevaluating success: shifting from financial milestones to personal fulfillment Practical strategies for generating referrals without asking Distinction between word-of-mouth, introductions, and true referrals How building relationships with referral sources differs from prospecting and marketing Adapting business models over time based on market shifts and personal life changes Protecting intellectual property in a rapidly evolving AI landscape The impact of consistent content like books and podcasts on long-term trust-building   Timestamps:   00:00 – Welcome & Stacey’s background: from embarrassment to branding 02:07 – What others might say about Stacey at her kids’ baseball game 03:29 – The importance of being on brand and intentional with style choices 04:34 – Stacey’s book: Generating Business Referrals Without Asking & Referable Client Experience 05:49 – The pivotal moment: learning from her first business failure 06:46 – The evolution from corporate America back to entrepreneurship 07:16 – Why entrepreneurship is in her blood and the desire for control and freedom 08:32 – How Stacey’s lifestyle aligns with her brand values 09:23 – Defining success beyond revenue: family, fulfillment, and authenticity 10:13 – The yearly reset ritual to realign goals and priorities 11:12 – How setbacks and life surprises shape her resilience and business approach 12:26 – The importance of understanding your true “why” 13:51 – Navigating businessduring life changes and market shifts 14:19 – Developing her core strategies: referrals, client experience, and new client acquisition 15:50 – Lessons from her first HR consulting firm & the value of scaling 16:47 – Why she returned to corporate America before launching her second business 17:13 – Recognizing opportunity in necessity & the power of strategic niche selection 18:55 – Building a productivity coaching business through genuine relationships 20:19 – Transitioning into her current focus: referral systems and relationship building 22:08 – Overcoming the early hype and misconceptions around referrals 23:29 – The three-legged stool approach: referrals as a separate, relationship-based pillar 24:54 – Humanizing referral conversations and avoiding gimmicks 26:16 – Tracking referral sources accurately and avoiding self-referrals 27:57 – Finding your niche and leveraging your personal network for referrals 29:26 – Creating scalable programs that meet clients where they are 30:56 – Adjusting business models based on market preferences 32:41 – Protecting your IP in a digital age & AI considerations 36:46 – Authentic connection strategies: permission, intentionality, and specificity 38:19 – The evolution of her business offerings & online vs. in-person strategies 41:23 – Teaching clients how to get referrals without asking directly 44:47 – Moving away from traditional “ask for referrals” tactics 47:31 – Reframing referrals as part of the core relationship-building process 49:35 – The “Go-Giver” mindset & serving genuinely for the long term results 51:52 – Strategic introductions & the importance of context & permission 54:36 – How true referrals differ from word-of-mouth buzz or accidental introductions 56:08 – The importance of data in understanding referral dynamics 57:23 – Overcoming objections to referral strategies and unlearning misconceptions 58:52 – The influence of books and podcasts on long-term trust-building 62:19 – Planning future content and strategic themes for ongoing growth 63:21 – The process of writing her latest book & foundational referral strategies 66:01 – Combining book, podcast, and relationship-building for sustained growth 67:32 – Diversifying client acquisition channels to reduce risk 68:22 – The “why” behind her entrepreneurial drive: from freedom to meaningful impact 70:49 – Lessons from setbacks: blessings in disguise and resilience 73:00 – Protecting your business in the AI era: authentic human connection matters 76:21 – Ensuring confidentiality & IP protection in today’s digital world 77:55 – The future of AI: leveraging tools without compromising core values 78:48 – The irreplaceable role of human emotion & intuition 79:33 – Final thoughts & how to connect with Stacey   Resources & Links: Generating Business Referrals Without Asking by Stacey Brown Randall Referable Client Experience by Stacey Brown Randall Roadmap to Referrals Podcast Stacey Brown Randall on LinkedIn Stacey’s Website

    1h 20m

  3. APR 21

    167: Building a Business Rooted in Love, Not Profit with Stephen Phelan

    In this episode, hosts sit down with Stephen Phelan, Chief Spiritual Integration Officer at Faith-Driven Entrepreneur, to unpack a powerful idea: what if business wasn’t just about profit—but about people? Stephen shares the story behind Movement Mortgage and how a bold vision during the 2008 financial crisis led to a company built on love, purpose, and impact. From redefining leadership to transforming communities through education and service, this conversation challenges the way we think about success in business. If you’ve ever wondered how faith, purpose, and entrepreneurship can actually work together—this one hits deep. Core Takeaways Love can be operationalized in business — it’s not just a feeling, it’s systems and structure Great companies meet human needs, not just market needs Purpose scales culture faster than profit ever will You don’t have to separate faith and business—but you also don’t force it Real leadership development happens outside comfort zones Generosity + boundaries (financial finish lines) unlock impact The 4 Needs of the Human Heart (Framework) Help in crisis – People want support when life hits hard Friends at work – Belonging and relationships matter Purpose – People want their life and work to mean something Faith / deeper meaning – An opportunity to explore something bigger Notable Quotes “We exist to love and value people.” “If your teammates thrive, your business will thrive.” “Don’t run from broken systems—redeem them.” “Set a financial finish line. Decide what ‘enough’ looks like.” “Put people on a plane. That’s the best leadership development.” Calls to Action Reflect: What’s your business really built on—profit or people? Identify one way you can serve your local community this month Share this episode with another entrepreneur or leader Leave a rating/review if this conversation impacted you

    1h 13m

  4. APR 7

    166: Leadership, Humility & the Journey from Farm Fields to Global Business with Jamie Ledford

    Brief summary of show: Jamie Ledford, President of Golf Pride, shares his journey from growing up in Walla Walla, Washington, to leading a global brand. Through stories of farm life, mentorship, international experiences, and career pivots, Jamie reflects on leadership, humility, and the importance of people in shaping both personal and professional success. This episode explores how life’s unexpected turns often lead to the most meaningful opportunities.   Key topics discussed & time stamps: • Early life in Walla Walla and farm influences (00:08) • Lessons from Jamie’s grandfather and work ethic (00:10) • Leadership mindset and desire to lead (00:22) • Career pivots and unexpected opportunities (00:25) • International experience in Italy and global perspective (00:32) • Consulting, Starbucks, and business growth strategies (00:38) • Transition into Callaway and Golf Pride (00:45)   List of resources mentioned in episode: • Golf Pride • AT Kearney Consulting • Johns Hopkins SAIS   Calls to action: • Follow the Anything But Typical Podcast • Share this episode with a friend or colleague

    1h 15m

  5. MAR 24

    165: From Navy SEAL to CEO with Tim CruickShank

    Brief summary of show: What can Navy SEAL training teach you about leadership, business, and life? In this episode of Anything But Typical, Gary and Ben sit down with retired Navy SEAL Lieutenant Commander Tim Cruickshank, founder of Bone Frog Coffee Company, to break down the mindset, discipline, and team-first philosophy that shaped his journey. Tim shares how elite military training—including BUD/S and combat deployments—built the mental toughness and adaptability he now uses as an entrepreneur. More importantly, he reveals how his business was born out of a deeper mission: honoring fallen teammates and supporting Gold Star families. This episode is a powerful conversation on leadership, resilience, entrepreneurship, and what it truly means to put others first—in business, family, and life. Key topics discussed: 00:01:00 – The “heartbeat question” and defining your legacy 00:05:00 – Military upbringing and lessons in integrity and trust 00:09:00 – How Tim decided to become a Navy SEAL 00:18:00 – What BUD/S training is really like (mental + physical) 00:29:00 – Building mental toughness: “30 seconds at a time” mindset 00:33:00 – Combat lessons: adaptability, leadership, and trust 00:38:00 – Transitioning from military to entrepreneurship 00:39:00 – The origin story of Bone Frog Coffee Company 00:41:00 – Starting a business with no experience + finding mentors 00:47:00 – Building during COVID and learning from customers 00:49:00 – Leadership lessons from Navy SEAL training applied to business 00:54:00 – Scaling impact and giving back to Gold Star families Key takeaways: Leadership starts with serving others first, not yourself Mental toughness is built through small, repeatable wins under pressure The best teams are built on trust, accountability, and shared hardship Entrepreneurship requires adaptability, humility, and constant learning Purpose-driven businesses create deeper loyalty and long-term impact Surrounding yourself with mentors accelerates growth significantly Common questions answered in this episode: What is BUD/S training like? BUD/S (Basic Underwater Demolition/SEAL training) is one of the most intense military training programs in the world, designed to push candidates mentally and physically. It focuses heavily on teamwork, resilience, and mental endurance, with extremely high attrition rates. How do Navy SEALs build mental toughness? Navy SEALs develop mental toughness by breaking overwhelming challenges into smaller time increments (like 30 seconds at a time), controlling their mindset, and learning to operate under extreme stress and discomfort. What leadership lessons come from Navy SEAL training? Key leadership lessons include: Put your team before yourself Adapt quickly under pressure Communicate clearly in chaos Earn trust through consistency and action How do you start a business with no experience? Tim’s approach: Surround yourself with experts and mentors Start small and iterate quickly Listen to customer feedback Stay consistent and adaptable What makes a purpose-driven business successful? A purpose-driven business builds deeper customer loyalty by aligning its mission with impact. In this case, giving back to Gold Star families and honoring fallen heroes creates emotional connection and long-term brand trust. Keywords: Navy SEAL mindset, leadership lessons, mental toughness, entrepreneurship journey, purpose-driven business, startup advice, team culture, business leadership, resilience training, Bone Frog Coffee, veteran-owned business Resources mentioned: Bone Frog Coffee Company – https://www.bonefrogcoffee.com GovX (military & first responder discounts) Calls to action: Visit: https://www.bonefrogcoffee.com Get 10% off your first order Military & first responders: 20% off via GovX Support a mission that gives back to Gold Star families Follow Anything But Typical for more real conversations on leadership & business Social handles: Instagram: @trustbgw Facebook: BGW CPA, PLLC TikTok: @bgw.advisors LinkedIn: https://www.linkedin.com/company/trustbgw/

    1h 3m

  6. MAR 10

    164: The Power of Relationships in Business and Life with Ashley Tison

    Episode live date: March 10 Name of show: Anything But Typical Podcasts Episode number and title: Episode 164: The Power of Relationships in Business and Life with Ashley Tison Brief summary of show: What if the most important business question has nothing to do with business? In this episode, Ashley Tison shares the powerful question he returns to over and over again: “If I were given six months to live, what would be my regrets?” Through years of walking alongside entrepreneurs navigating growth, exits, and major life transitions, Ashley has seen how success often gives way to a deeper realization — that time, relationships, and meaning matter more than most people expect. This conversation explores the tension between building something significant and not losing your life in the process. Bullet points of key topics discussed & time stamps: 0:00 – Opening reflection: the question that changes everything 1:12 – Why entrepreneurs eventually start asking deeper questions 2:48 – The hidden cost of building, growing, and chasing success 4:15 – Why founders often realize too late what mattered most 5:42 – Family, experiences, and meaning in the next chapter 7:03 – How the “six months to live” question reframes priorities 8:21 – Why the next chapter people want is often the one they’ve delayed 9:37 – Closing thought: sometimes business conversations become life conversations List of resources mentioned in episode (including sponsors): OZ Pros OZPros.com Annie Dillard quote: “How we spend our days is, of course, how we spend our lives.” Calls to action: Learn more at OZPros.com Visit trustbgw.com Follow Anything But Typical and BGW on social media: Instagram: @anythingbuttypical LinkedIn: BGW CPA, PLLC

    1h 3m

  7. FEB 24

    163: Doing Business the Right Way with Joe III, Joe IV, & Ben Cherry

    “It’s not about us.” – Joe Cherry IV Long before Cherry & Associates was a three-man team, it was a father at 39, staring down the risk of starting over. New city. Commission-only real estate sales. Kids who could sense that the math at the kitchen table didn’t quite add up. Joe Cherry III’s sons didn’t understand spreadsheets or market cycles. But they knew this: there were opportunities that would have paid well — and their dad said no. They heard late conversations about faith & risk. About whether protecting a client’s long-term future mattered more than protecting their family’s short-term comfort. About what it means to live with your name on the door. And they saw what conviction costs: Discount groceries. Honest family meetings. The quiet weight of doing the right thing. Then they left. One entered Ranger School. The other commanded tanks. Different arenas. Same refining fire. When they came back, it wasn’t to inherit something easy. It was to join something tested. Today, when the three of them sit across from a client, the conversation doesn’t sound like three salesmen competing for airtime. It sounds like three men asking what’s right for the client — & then doing the work to make it happen.   To learn more, visit CherryAssociates.com.

    1h 15m

  8. FEB 11

    162: Behavioral Performance In Business with Cathy Maday

    “I’ve been poor before. That doesn’t bother me.” – Cathy Maday Cathy didn’t grow up around startup jargon or leadership books. She grew up on the Bad River Indian Reservation in northern Wisconsin. Work wasn’t a phase. It was how you made things possible. You did chores, took odd jobs, & learned early that no one was coming to rescue you. There was freedom in that. By 12, Cathy was holding her first paper paycheck. She hasn’t stopped working since — not always because she had to, but because work meant agency. Motion. A steady sense of “I can handle what’s next.” That assurance followed her from childhood into college, into technology, & into corporate environments where she saw it clearly: systems weren’t failing. The people inside them were carrying too much, alone. Eventually, Cathy did what entrepreneurs do. She chose the harder path & built the solution — Wingspan — from the same instinct that had always guided her: if you want options, you create them. This episode isn’t about hustle or reinvention. It’s about knowing when the instincts that made you strong are asking for something completely new. To learn more, connect with her at WingspanPerformance.com. Entrepreneurship isn’t about escaping where you come from. It’s about carrying what made you — and knowing what to set down. As Wendell Berry wrote, “It may be that when we no longer know what to do, we have come to our real work.”

    1h 15m
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5
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About

Gary Frey & Ben McDonald host round table conversations discussing entrepreneurship, leadership, and success on your own terms.

Information

  • Creator
    Gary Frey & Ben McDonald
  • Years Active
    2019 - 2026
  • Episodes
    169
  • Rating
    Clean
  • Copyright
    © Copyright 2026. All rights reserved.
  • Show Website
    Anything But Typical