Anything But Typical

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

  1. 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

  2. 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

  3. 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

  4. JAN 27

    161: Breaking Out of Sleepwalking At Work To Succeed On Your Own with Lauren Goodell

    “I closed the biggest deal of my life playing Candy Crush on my phone over Zoom… I could do this in my sleep at this point.” — Lauren Goodell One moment, Lauren Goodell was operating at the highest level — thriving in corporate tech, leading the room, closing deals most people never touch. And then, something became clear. The work wasn’t hard anymore. The risk was gone. The challenge had faded. What once demanded everything she had now required very little. In that moment, her future shifted. Not because she failed — but because she succeeded. And she knew that mastery without growth is just another form of standing still. So, she walked away. What followed wasn’t instant clarity. It was friction. Failure. Momentum earned the hard way. Today, Lauren is building technology that handles the prep work she got bored of — so people can focus on the conversations that actually matter. That moment — the quiet realization — is where her story really begins. Connect with her on LinkedIn & learn more at getZinnia.ai Success doesn’t always signal arrival. Sometimes, it’s the cue to begin again. Anaïs Nin said it best: “And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.”

    1h 3m

  5. JAN 13

    160: How a $5 Gift Card Led to Starting His Own Business with George El-Hage

    “I’d like people to say this guy lived life with no regrets.” – George El-Hage There are moments in life when something small reveals something big. For George, it was a note on his desk praising his performance… along with a $5 Tim Hortons gift card. It wasn’t the amount that bothered him. It was the message underneath. Years of effort reduced to something transactional. Something polite. Something small. That’s when he knew. Not that he needed a new job — but that he needed a different path, one that matched how he works, how he connects, & how he shows up every day. That recognition became direction. What emerged was Wave, a digital business card platform — not just another cool tech tool, but an answer to connections that deserved more than a polite exchange, a quick goodbye — or a toss in the trash. Turns out, George’s “no regrets” isn’t just about risking everything. It’s about paying attention — and taking action — when the truth shows up quietly. To learn more, head to wavecnct.com. Wayne Dyer once said, “Don’t die with your music still in you.” George won’t.

    1 hr

  6. 2025-12-30

    159: When Your Passion Project Becomes More Successful Than Most Small Businesses with Daniel Hearl

    “It’s the fleeting moments of bliss — being connected to your family in a real, meaningful way.” – Daniel Hearl Dan has a big job. Really big. He leads a 300+ person sales organization inside a Fortune 100 company. It’s not what he talks about most. In fact, he rarely talks about titles, quarters, or wins at all. What he talks about is time — with his kids, with his family, & in life outside the day-to-day grind. It’s not by accident. Dan grew up watching his parents work hard to provide, doing everything right but often letting work take over the life they were trying to build. What he learned wasn’t to chase more. It was to guard the moments work can quietly steal. So he’s intentional about where his energy goes, who gets it, & how not to let “success” quietly replace presence. Because in the end, there are only a few relationships that truly shape a life. And you don’t protect those casually. You give them everything you’ve got. To learn more, connect with him on LinkedIn. Not all legacies are loud. Some are built quietly — right where you are. As Audrey Hepburn once said, “The best thing to hold onto in life is each other.”

    1h 3m

  7. 2025-12-17

    158: The Journey From Never Walking Again to Running a Half Marathon with Dean Otto

    “Belief isn’t a feeling — it’s a decision.” – Dean Otto One moment, Dean Otto was living life on his terms — an avid cyclist, athlete, & high-achieving leader. And then, everything changed. On what should have been a routine morning bike ride, an F-150 — a truck weighing more than two tons — struck him from behind. The impact shattered his spine. Doctors gave him a 1–2% chance of ever walking again. In that instant, his future was rewritten. Not by the accident — but by the decision he made next. Dean didn’t put his faith in percentages. He put it in belief — in himself & what persistence could unlock. Months of grueling rehab followed. Pain. Setbacks. Uncertainty. And then, miraculously, steps. One year later, Dean crossed a half-marathon finish line. Not alone, but alongside two unlikely partners: the surgeon who helped him walk again & the driver who hit him. Together, they raised nearly $100,000 for spinal cord injury patients — turning trauma into hope & recovery into something bigger than self. Dean could have stopped at survival. Instead, he chose impact. Connect with him at DeanOttoSpeaking.com Strength doesn’t always look like winning. Sometimes, it looks like getting back up — and bringing others with you. As Albert Camus wrote, “In the depth of winter, I finally learned that within me there lay an invincible summer.”

    1h 7m

  8. 2025-12-02

    157: Solving The Ugly Problems Nobody Wants with Kenneth Lopez

    “I like to solve problems, & I never give up.” – Martin Kenneth Lopez Most founders talk tough. Kenneth grew up in a place that required it. Lima, Peru — beautiful on the surface, unforgiving underneath. Corruption. Precarity. An environment built to break entrepreneurs. There’s no help desk in a place like that. You either solve problems… or you get swallowed. That wiring became his operating system. So, when he launched his first company in his early 20s, he didn’t seek the easy path — he sought a bigger arena. “Forget local,” he said. “I’m building for the U.S.” No connections. No warm introductions. Just hunger, a laptop, & LinkedIn. And his pitch wasn’t polite — it was legendary: “Give me the project nobody wants. The ugly, neglected, impossible one. If I don’t deliver, you don’t pay me.” All the risk on him. All the upside for them. That’s how a kid from Lima ended up solving Perl script nightmares for Bank of America… & earning a reputation as the one-man A-team you call when everyone else slinks away. Today at Equals 11, the stakes are higher — Salesforce chaos, global teams, stalled initiatives — but Kenneth’s ethos hasn’t budged: Run toward the hard. De-risk it for the client. Solve — don’t whine. If you’re the kind of person who gets stronger when the work gets messy, this episode is for you. Connect with him through Equals 11. Kenneth doesn’t quote Churchill — he proves him right: “Difficulties mastered are opportunities won.”

    52 min
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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
    164
  • Rating
    Clean
  • Copyright
    © Copyright 2026. All rights reserved.
  • Show Website
    Anything But Typical