Untrapped Entrepreneur

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You’re the CEO. So Why Are You Still Doing Everyone Else’s Job? with Derek Fredrickson

Ben Davis — Thu, 22 Oct 2026 22:15:55 GMT

What if the CEO’s job isn’t to run the company?

In this episode of The Untrapped Entrepreneur, Derek Fredrickson, founder and CEO of The COO Solution, challenges one of the most common assumptions entrepreneurs make as their businesses grow: that because they can do everything, they should keep doing everything.

Derek explains why founders should spend more time thinking and less time doing, why entrepreneurs often become trapped as the operator inside their own company, and how getting out of the day-to-day can unlock greater clarity, confidence, growth, and freedom.

We also discuss Derek’s journey from fractional COO to founder and CEO, how he built a seven-figure business in his first year, why he had to overcome his own resistance to sales, and the mindset shift that allowed him to step out of the room and trust his team to deliver results without him.

Thank you to our sponsor Forja:

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(Host): https://www.linkedin.com/in/untrapped-entrepreneur/

Did You Buy a Business… or Just Buy Yourself a Job? with Greg Mohr

Ben Davis — Thu, 15 Oct 2026 20:34:51 GMT

Buying a business is supposed to create freedom. But what happens when you spend your money, take the risk, and end up creating another job for yourself?

In this episode of The Untrapped Entrepreneur, Greg Mohr, founder of Franchise Maven and bestselling author of Real Freedom, breaks down one of the most common traps he sees franchise owners and entrepreneurs fall into: doing everything themselves.

Greg has helped hundreds of people invest in franchise territories, but he has also helped thousands realize that franchise ownership was not the right fit for them at that point in their lives. In this conversation, he explains the difference between a founder and a franchisee, how to evaluate whether a franchise actually fits your skills and goals, and why following a proven system matters.

Thank you to our sponsor Forja:

The “Not Enough” Trap Every Entrepreneur Needs to Escape with Steve Barton

Ben Davis — Thu, 08 Oct 2026 20:06:31 GMT

What happens when you achieve the success you thought would make you happy, and it still doesn’t feel like enough?

In this episode of The Untrapped Entrepreneur, Steve Barton, founder of Steve Barton Coaching and creator of the Game of Ten, shares lessons from more than four decades in business, including growing his family’s floral company from $200,000 to more than $2 million in annual revenue before moving into leadership and performance coaching.

Steve breaks down some of the most common beliefs he sees holding entrepreneurs and high achievers back: “I’m not good enough,” “I don’t do enough,” and “I don’t have enough.” We explore why successful people can become trapped chasing more, what happens when your business or achievements become your identity, and why reaching the next financial or professional milestone may not solve the underlying problem.

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(Host): https://www.linkedin.com/in/untrapped-entrepreneur/

Build a Business That Gives You Your Life Back with Kenneth Kollasch

Ben Davis — Thu, 01 Oct 2026 16:57:23 GMT

Entrepreneurs often start businesses to create more freedom, only to end up with less time, more stress, and a company that depends on them for everything.

In this episode of The Untrapped Entrepreneur, third-generation entrepreneur and business coach Kenneth Kollasch breaks down what he calls the “someday fallacy,” the belief that you’ll finally have time for your spouse, family, friendships, and the life you want once the business reaches the next milestone.

Kenneth explains why founders need to move through three distinct stages of business, starting, scaling, and stabilizing, and why skipping the stabilization stage can lead to burnout and even damage the business you’re trying to build.

Thank you to our sponsor Forja:

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(Host): https://www.linkedin.com/in/untrapped-entrepreneur/

7 Words Made Her $3 Million in One Week with Aurora Winter

Ben Davis — Thu, 17 Sep 2026 18:51:34 GMT

Can seven words really change the trajectory of a business?

Aurora Winter says yes. After struggling to sell what she knew was a million-dollar idea, one change in messaging helped generate $3 million in sales in a single week. The product, price, and team stayed the same. The words changed.

In this episode of The Untrapped Entrepreneur, Aurora shares what that experience taught her about messaging, storytelling, entrepreneurship, and the power of saying the right thing at the right time. She also opens up about losing her husband and business partner, rebuilding her life after tragedy, and how that journey eventually led her into film, television, publishing, and helping others turn their stories into opportunity.

Thank you to our sponsor Forja:

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(Host): https://www.linkedin.com/in/untrapped-entrepreneur/

Why Growing Too Fast Can Destroy Your Business with Kalanithi Venkatesan

Ben Davis — Tue, 08 Sep 2026 22:30:00 GMT

Growing fast sounds like every entrepreneur’s dream, but scaling before your leadership, cash flow, and sales infrastructure are ready can become one of the most dangerous traps in business.

In this episode, entrepreneur and strategic advisor Kalanithi Venkatesan shares lessons from building and successfully exiting his professional services company, including why he planned his exit years in advance, how he increased the value of the business beyond revenue, the hiring mistakes that cost them money, why cash flow matters more than many founders realize, and the three things every company should have in place before pursuing aggressive growth.

If you’re building, scaling, funding, or preparing to sell a business, this conversation offers practical lessons from someone who has experienced the entire entrepreneurial cycle.

Thank you to our sponsor Forja:

The Legal Mistake That Can Destroy Your Business with Matthew Fornaro

Ben Davis — Wed, 05 Aug 2026 23:29:30 GMT

Starting a business is exciting, but moving too fast can create expensive legal and operational problems later. In this episode of The Untrapped Entrepreneur, business attorney and entrepreneur Matthew Fornaro explains why filing an LLC is only the beginning, which contracts and protections founders often overlook, how AI is changing legal work, and why every AI-generated document still needs professional review.

He also shares lessons from building his own law firm, developing business knowledge outside the legal profession, protecting intellectual property early, avoiding costly marketing mistakes, and building a trusted network of professionals. This conversation is essential for entrepreneurs, small business owners, and founders who want to build on a strong foundation and avoid preventable mistakes..

Thank you to our sponsor Forja:

Stop Chasing AI Features. Start Solving Real Problems with Jamarri Jones

Ben Davis — Thu, 16 Jul 2026 17:30:00 GMT

AI has made building products easier than ever, but it has also created a new generation of entrepreneurs chasing features instead of solving real problems.

In this episode of The Untrapped Entrepreneur, Ben Davis sits down with Jamarri Jones, founder of Klyno AI, to discuss what it actually takes to build a business in the AI era. They explore why execution matters more than ideas, how bad partnerships derail promising companies, why customer obsession beats feature obsession, and how entrepreneurs can use AI without becoming dependent on it.

From Dyslexia to CEO: The Trap That Almost Broke Him with Travis Hollman

Ben Davis — Fri, 03 Jul 2026 21:30:00 GMT

Travis Hollman, CEO of Hollman Inc. and founder of MeSpace, joins the podcast to share the entrepreneurial lessons he learned through childhood adversity, dyslexia, business success, painful mistakes, and the trap of ego.

In this episode, Travis opens up about being forced out of his family business, chasing ventures outside of his expertise, losing $600K in the music business, and eventually learning why entrepreneurs need to lean into what naturally makes sense to them. He also shares the story behind MeSpace, his adaptive workstation designed to help neurodiverse professionals focus, thrive, and work in environments built around how their brains actually operate.

Thank you to our sponsor The Gents Place:

The Hard Truth: A Great Product Doesn’t Mean a Great Business with Nik Hall

Ben Davis — Tue, 24 Mar 2026 20:30:00 GMT

A great product is not enough if the business model does not work. In this episode, Nik Hall shares the hard lessons he learned from building, scaling, and selling a consumer brand, then launching an Amazon growth agency with a much simpler business model. We get into one of the biggest traps entrepreneurs face: confusing passion for a product with a business that actually makes money.

Nik also opens up about faith, family, priorities, relationships over transactions, and why long-term success depends on more than just chasing revenue. This conversation is for founders, operators, and ambitious builders who want to grow the right business, with the right values, in the right order.

Thank you to our sponsor The Gents Place:

This Startup Mistake Kills Great Ideas Before They Ever Work | Dennis R. Mortensen

Ben Davis — Thu, 12 Mar 2026 21:00:00 GMT

Most founders do not fail because they lack ambition. They fail because they fall in love with the technology instead of the actual problem. In this episode, Dennis R. Mortensen breaks down one of the most dangerous traps in entrepreneurship: building around something exciting, innovative, or technically impressive before proving that the pain is real, urgent, and worth solving.

He shares how he stress tests ideas before committing years of work, why he believes founders should be loyal to the problem rather than the product, how to stay focused when customers ask for adjacent features, and why saying no is often the most strategic move a startup can make. This is a sharp, practical conversation for founders, operators, and ambitious builders who want to create products that solve something real, not just something cool.

Thank you to our sponsor The Gents Place:

3 Startup Traps That Kill Founders (From a 4x Entrepreneur) with David T. Scott

Ben Davis — Thu, 05 Mar 2026 17:00:00 GMT

Most founders think the first step to growth is raising money and spending on marketing. According to serial entrepreneur and pioneering marketer David T. Scott, that mindset can quietly destroy your startup before it ever finds product-market fit. In this episode of The Untrapped Entrepreneur, David shares the three traps he sees founders fall into again and again: spending capital too fast, chasing customer acquisition before understanding the funnel, and assuming you are your own customer.

Drawing on experience from multiple startups, leadership roles at companies like Amazon Web Services and Twitter, and the sale of his comedy streaming platform to Kevin Hart and Lionsgate, David breaks down practical lessons about cash discipline, product-market fit, and truly understanding the customer journey. If you're building a startup, raising capital, or trying to scale your first product, this conversation will help you avoid some of the most common and costly mistakes founders make.

Thank you to our sponsor The Gents Place:

He Built a $150M Business...Then Lost 80% Overnight with Vincent Matranga

Ben Davis — Tue, 24 Feb 2026 22:00:00 GMT

What happens when your company is flying high, then loses 80% of revenue in a single week? In this episode, Vincent Yang shares the full arc of building and scaling Cheetah past $150M in annualized sales, the brutal COVID collapse that melted demand overnight, and the operational decisions required to survive when everything turns into a wartime scenario.

We get into the real founder traps: hypergrowth addiction, scaling the physical world faster than your systems, burnout that turns a mission into “just a job,” and why bad hires are almost always the founder’s fault. Vincent also breaks down the mindset shift that saved him, focusing only on what you can control, building contingency plans, and managing your energy because your team mirrors your nervous system.

The Truth About Pitch Decks (Most Founders Learn This Too Late) - Eric Harris

Ben Davis — Thu, 05 Feb 2026 20:00:00 GMT

Most founders and leaders think they have a communication problem, but it’s usually a clarity problem. In this episode, Eric Harris, founder of GatherRound and creator of the Campfire Method, breaks down why slide decks quietly sabotage leadership, culture, and buy-in, especially in high-stakes moments like strategy rollouts, investor conversations, and company change.

We unpack the real traps that pull entrepreneurs off-mission (validation, comfort, money), why “send me the deck” can be a giant red flag, and how the best leaders learn to make their message stick without hiding behind slides. If you want your strategy understood, your culture stronger, and your ideas to move faster through people, this one’s for you.

Teacher to Founder to Fund Manager: Miriam-Altman Reyes’ Playbook

Ben Davis — Thu, 22 Jan 2026 20:00:00 GMT

In this episode, Miriam Altman Reyes shares with Ben Davis how her time as a public high school teacher led her to tackle chronic absenteeism, build an EdTech company, and eventually sell it, then turn that experience into Brass Ring Ventures, where she now backs founders building the future of learning and work.

You will hear the traps she sees all the time: chasing hot trends without lived experience, pitching what investors want instead of what customers want, hiring the wrong “big company” talent too early, and mismanaging cash when markets tighten. She also breaks down how to protect your people and legacy when selling, including how to build buyer relationships early and how to get the real story from founders who have already been acquired.

How to Lead Remote Teams Like a Coach, Not a Cop - Geoff McQueen

Ben Davis — Fri, 09 Jan 2026 19:00:00 GMT

In this episode of the Untrapped Entrepreneur Show, host Ben Davis speaks with serial tech entrepreneur Geoff McQueen about his journey through multiple startups and the challenges of managing remote teams. They discuss the importance of maintaining visibility and engagement in a remote work environment, the pitfalls of over-monitoring employees, and the impact of side hustles on performance.

Geoff shares insights on how his latest venture, Team Score, aims to provide managers with the tools they need to foster a high-performance culture without resorting to invasive monitoring techniques. The conversation emphasizes the need for effective leadership and the balance between trust and accountability in remote work settings.

Thank you to our sponsor The Gents Place:

http://tgpfranchising.com