The Entrepreneur DNA

Eric Winegard’s story is not the polished founder myth. Before he became CEO and co-founder of Rare Blue Moon Marketing, he was a kid raised by a single mother on welfare, a teenager experimenting with drugs, and a young man who realized no one was coming to save him.

In this episode of Entrepreneur DNA, Justin Colby sits down with Eric to unpack how he went from 17 years in a W-2 sales role to building an $18 million marketing business in just three years.

What You’ll Learn in This Episode

In this episode I sat down with Kristian Mtetwa, a wealth advisor who leads Synergy Private, a multifamily office serving athletes, entertainers, entrepreneurs, and executives. We start by busting the biggest myth about the rich: they aren’t hoarding money, they’re obsessed with adding value because that’s the only way to keep it. Kristian explains what a family office actually does, why giving anyone power of attorney over your money is a massive liability, and the numbers ($10M liquid net worth or $1M in annual income) where it starts to make sense. We dig into ambition vs. envy...

Your operator strengths might be the very thing holding you back. Gary Vaynerchuk shares a hard financial realization.

Gary Vaynerchuk is known for spotting internet trends years before they happen. But even with that foresight, he faced a brutal reality in 2026. Sometimes, the skills that get you to a certain level of business growth are the exact same habits that prevent you from scaling further.

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In this episode, I sat down with my GOAT, Gary Vaynerchuk, and he did not hold back. Gary broke down his entire empire, from VaynerX and VeeFriends...

Everyone wants to talk about AI, but my guest this week would rather talk about people. Heather Simpson spent years in real estate building brokerages and personal brands for agents before making a hard pivot to build something for women entrepreneurs specifically. Today she runs Her Connection Hub, a coworking and community space in the Pacific Northwest, and she is expanding into Northern California. We got into why she thinks too many people are outsourcing their thinking, the gap she saw between hustle culture and the "make a million from the beach" crowd, and what actually separates the women...

AI is all anyone can talk about right now, but most of us are just getting started with it while the giants have been building it for two decades. In this episode I sat down with Sneha Shah, CEO and co-founder of Hazel AI, who spent nearly 20 years at Amazon and Google as the engineer behind the scenes. She was on the team that built Amazon same-day delivery and scaled it to ten countries, then went to Google as a founding engineer on Cloud Spanner, the global database that powers companies like Deutsche Bank and Nintendo, before building Vertex...

In this episode I sit down with Kevin C. Roy, CEO of GreenBanana SEO, who's spent the last 15 years mastering search engine optimization and is now at the forefront of how AI is completely rewriting the rules of how businesses get found online. Kevin walks me through his wild entrepreneurial journey, from getting laid off and going door to door offering free websites, to bringing on a 50/50 business partner that nearly sank everything, to surviving a lawsuit from a sales partner who tried to put him out of business entirely. We get real about why most business partnerships fail...

In this episode, I sit down with Christina Deering, energy and intuition coach and host of the You Unlimited podcast, to talk about something I think about constantly: how the energy you bring to your business matters just as much as the strategy. Christina walks us through the difference between wishing for something and actually being aligned with it, why so many business owners build something they don't even want and end up wanting to burn it down, and how to use your body to tell whether you're in the right lane. She opens up about going through four...

In this episode, I sit down with Austin Armstrong, bestselling author of Virality! and founder of Syllaby, to nerd out on everything happening in AI and content right now. We get into how fast AI video and image generation is moving, why it's getting harder to know what's even real online anymore, and what that means for creators and business owners. Austin breaks down his thesis of being a business owner who creates content instead of a content creator chasing views, how to use keyword research tools to find exactly what your audience is searching for, why faceless content...

In this episode, I sit down with Ilhiana Rojas, who climbed the corporate ladder to become a senior Fortune 500 executive in just 12 years — often the only woman, and the youngest, in the boardroom. But somewhere along the way, chasing the version of success she thought she was supposed to have, she lost herself so completely that she burned out and fell into deep depression. We talk about what it actually looks like to reconnect with who you are after you've lost your voice, why building the right circles of people around you is one of the most important things yo...

Want help turning your story into a book? Book a free call with Chandler's team to map out your book: selfpublishing.com/justin

I sat down with my friend Chandler Bolt, who built self-publishing.com into an 8-figure company (north of $80 million in sales) by his early thirties, and we got into exactly how he did it. We talked about the mindset that separated him from guys like me in our twenties, why he scaled almost entirely without social media by leaning into SEO, content, and business development partnerships instead, and the "thank you card challenge" and...

In this episode, I sit down with Tiffany Ward, founder and CEO of Human Creative, the company behind Certified Human Content, a service that live-monitors the entire writing and creative process to prove a piece of work was made without generative AI. We get into just how much of what we read today (emails, resumes, social captions, even "motivational" posts) is quietly AI-generated, and why that's eroding trust across education, journalism, hiring, and the creator economy. I share my own story of getting caught plagiarizing my senior year at UCLA, long before AI existed, and we talk about how...

Book a free 15-minute consultation at manifesttherapy.com.

Nathaniel Cilley is a licensed mental health counselor, psychedelic therapist, and manifestation coach based in New York City, and he's joining our School.kol.com community to help entrepreneurs work through fear and mental roadblocks.

In this episode we cover:

FREE RESOURCE FROM BRAD SUGARS DM Brad on Instagram @BradleySugars the word "PLAYBOOK" and he'll send you his free business playbook on how to succeed in business. ---

In this episode, I sit down with Brad Sugars — the Founder and Chairman of ActionCOACH, the world's #1 business coaching firm with over 1,000 offices in 85 countries — to break down exactly what separates the entrepreneurs who scale from the ones who stay stuck. Brad calls out what he sees as the biggest epidemic in business right now: wimpy goals.

We dig into the three stages of business growth (0 to $1M, $1M to $...

Get your free copy of Allison's book 'Scale or Fail' - https://pinnacleglobalnetwork.com/dna

In this episode I sit down with Allison Maslan, founder and CEO of Pinnacle Global Network and Wall Street Journal bestselling author of Scale or Fail, who has personally built ten companies and helped her team mentor over 150,000 founders. We talk about why the business owner is so often the thing standing in the way of their own growth, and Allison walks me through her five phases of scaling, from the seeker all the way through what she calls the ringleader phase...

Are you ready to stop treating your startup like a side project and start building a scalable business? In this episode, Dr. Michael Burcham shares the hard-earned wisdom of a veteran who has transitioned from a physical therapist to a multi-million dollar private equity investor.

We dive deep into the mindset shifts required to go from a day job to a full-time founder, the critical importance of customer discovery, and why most investors won't touch your project until you have skin in the game. Michael breaks down the common mistakes technical founders make and how to navigate...

Get Mauricio's book 'Tackling Toxicity' on Amazon here: https://a.co/d/08uHkZag

In this episode I sit down with Mauricio Velasquez, a worldwide conflict resolution and emotional intelligence consultant who has trained in over seventy five countries, from Guantanamo Bay to the White House to professional sports organizations like the MLS. We get into why most people are conflict averse and what happens when you ignore toxic behavior instead of addressing it. Mauricio breaks down the difference between reacting and responding, how to spot your own triggers before they take over, and the exact language he...

In this episode I sit down with Brett Gilliland, founder and CEO of Elite Entrepreneurs, who has spent the last fourteen years helping business owners make the leap from hustler to real CEO. We dig into why so many founders get stuck right before the ten million dollar mark, and why it almost always comes down to control. Brett walks me through the four systems his company teaches to build a business that doesn't depend on the founder for everything, what a CEO's real job becomes once a leadership team is in place, and how to know when you're...

What does it really take to walk away from a seventeen-year corporate career and build an $18 million marketing agency in just three years? In this episode, Eric Winegard shares the mindset, discipline, and relentless commitment that helped him go from a troubled childhood and military structure to becoming the CEO of Rare Blue Moon Marketing.

We dive into the realities of entrepreneurship, the difference between paid ads and organic content, and why most businesses fail before marketing even begins. Eric breaks down the importance of networking without an agenda, building a real personal brand online, and why...

Free consultation / website: www.assetprotectionattorneys.com — Hillel offers to send complimentary copies of his latest books to anyone who mentions The Entrepreneur DNA.

In this episode, I sit down with Hillel Presser, a nationally recognized asset protection attorney who's helped protect over $11 billion in client assets and written six books on the subject. We get into why "it's not what you make, it's what you keep," and unpack the exact strategies the ultra-wealthy use to become "uncollectible" — from owning nothing and controlling everything through LLCs and limited partnerships, to the real difference between revocable and irre...

I sat down with Ian Watts, a workforce transformation specialist who's spent two decades helping companies fix what most of them get wrong about their people. Ian's story starts on the east side of Detroit, growing up on welfare, and it's what drove him to chase becoming a millionaire by 30 — which he hit almost four years early, right before his first business completely collapsed in 2006. That season is where he found his real why: building businesses that bless the world by taking care of the humans inside them. We got into why employee engagement is at some of the lo...

I sat down with Jon Ostenson, a two-time Inc. 5000 founder and the top 1% franchise consultant behind FranBridge Consulting, to break down everything most people get wrong about franchising. We talked about why "non-food franchising" is such an underrated path to business ownership, how to actually evaluate a franchise opportunity instead of just chasing passion, what it really costs and how long it really takes to get one off the ground, and why following the system matters more than being the smartest person in the room.

Jon also walked me through what it takes to scale into multiple...

Are you ready to stop treating your startup like a side project and start building a scalable business? In this episode, Dr. Michael Burcham shares the hard-earned wisdom of a veteran who has transitioned from a physical therapist to a multi-million dollar private equity investor.

We dive deep into the mindset shifts required to go from a day job to a full-time founder, the critical importance of customer discovery, and why most investors won't touch your project until you have skin in the game. Michael breaks down the common mistakes technical founders make and how t...

FREE RESOURCE FROM BRAD SUGARS DM Brad on Instagram @BradleySugars the word "PLAYBOOK" and he'll send you his free business playbook on how to succeed in business. ---

In this episode, I sit down with Brad Sugars — the Founder and Chairman of ActionCOACH, the world's #1 business coaching firm with over 1,000 offices in 85 countries — to break down exactly what separates the entrepreneurs who scale from the ones who stay stuck. Brad calls out what he sees as the biggest epidemic in business right now: wimpy goals.

We dig into the three stages of business growth (0 to $1M, $1M to $...

What does it really take to walk away from a seventeen-year corporate career and build an $18 million marketing agency in just three years? In this episode, Eric Winegard shares the mindset, discipline, and relentless commitment that helped him go from a troubled childhood and military structure to becoming the CEO of Rare Blue Moon Marketing.

We dive into the realities of entrepreneurship, the difference between paid ads and organic content, and why most businesses fail before marketing even begins. Eric breaks down the importance of networking without an agenda, building a real personal brand online, and why...

Exclusive listener discount: Use code ATTEND25 for 25% off your registration! Register here: sarahgibbons.com/shop/p/when-effort-stops-working

Join Sarah for a 75-minute virtual live workshop on Wednesday, June 3rd at 12 PM PT. This is the second in a series of four workshops and is designed for leaders who sense that the problem isn’t motivation — it’s the system they’re operating from. You’ll learn to work with capacity, timing, and internal alignment instead of against yourself.

In 75 minutes, you’ll identify:

Get your FREE copy of Tim's book 'Money, Your Friend' here: https://www.radicalcounselor.com/money-book

In this episode, I sit down with Tim Grimes—radical counselor, somatic coach, and bestselling author of Money, Your Friend—to tackle the side of entrepreneurship nobody puts on their Instagram highlight reel: the internal pressure, money shame, and chronic overthinking that silently sabotage even the most driven business owners. Tim breaks down why so many of us started this journey craving freedom but ended up more stressed than ever, and he shares the daily 10–15 minute practice from his book that helps...

Are you pushing yourself to the brink of burnout in pursuit of the superhuman entrepreneur ideal? In this episode of The Entrepreneur DNA, host Justin Colby sits down with behavioral health specialist Rachel Harvest to break down the toxic side of perfectionism and how to find true balance.

Throughout this deep dive, Rachel explains why high achievers often fall into the trap of extreme dieting, caffeine dependency, and emotional suppression. You will learn about the wise mind, a powerful combination of logic and emotion that allows for better decision making and sustainable growth. The conversation covers everything...

In this episode, I sit down with tax strategist David A. Perez, who has helped his clients save over $1 BILLION in taxes. We break down the fundamental difference between how wealthy people and broke people think about taxes, and David reveals specific strategies that anyone can use—from early-stage entrepreneurs making their first $50K to 7-figure earners looking to pay zero in taxes legally. We dive into depreciation strategies, the Augusta Rule, employing your children, turnkey investment opportunities, and why most CPAs aren't equipped to help high-income earners. David also explains the real reason people like Grant Cardone buy je...

Book a 30 min. consultation with Dr. Andrea: https://drandreawieland.youcanbook.me

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Get Dr. Andrea’s Book:

The Confident Performer: Rethinking Mental Performance for Athletes, Coaches and Parents https://www.amazon.com/s?k=The+Confident+Performer+Andrea+Wieland

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In this episode, I sit down with Dr. Andrea Wieland — an Olympic athlete, licensed psychologist, and elite performance coach — to unpack what it really takes to perform at the highest levels of sport, business, and life. Andrea shares her remarkable story of being cut from the US Olympic team eight times before final...

Sweet Addison's — Better-for-you, gourmet gluten-free and dairy-free desserts shipped nationwide. Get yours today! Go to - sweetaddisons.com

In this episode, I sit down with Addison LaBonte — former Division I college soccer player, ultra marathoner, and the founder of Sweet Addison's — to unpack one of the most raw and relatable entrepreneurial journeys I've had the pleasure of sharing on the show. Addison walks us through the identity crisis she faced after leaving college athletics, the shocking medical diagnosis of compartment syndrome that threatened to end her running career, and how sw...

Get Jen's book 'Lifting Up' and 'Showing Up' on Amazon today!

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In this episode, I sit down with Jen Marr — Human Disruption Specialist, author of Lifting Up and Showing Up, and founder of the organization Showing Up — who brings one of the most extraordinary and hard-earned perspectives on leadership I've ever encountered. Jen shares how being just 700 yards from the finish line during the 2013 Boston Marathon bombing, combined with her frontline support work after the Sandy Hook school shooting, gave her a transformational understanding of how humans navigate disruption, trauma, and change — and how those...

GET JOSH'S BOOK

If this episode resonated with you, grab Josh's book — it's the full playbook behind everything discussed today.

People Matter at Work by Josh Block Available now at Amazon, Barnes & Noble, Books-A-Million, and wherever books are sold.

 
In this episode, I sit down with Josh Block — a man who at just 29 years old was handed the reins to his family's healthcare imaging company, Block Imaging, which was generating $30 million in revenue at the time. Over the next 15 years, Josh scaled it to $215 million and orchestrated a landmark acquisition by a joint...

Take the 5 minute Get a GRIP Leadership Assessment today! Go to: https://www.reworkit.co/grip 

In this episode, I sat down with Jess Wass to break down what it really means to build a business and life that actually aligns with who you are. We talked about her “Managing 360” framework, why so many entrepreneurs feel stuck or overwhelmed, and how most of us are chasing success based on what we think we “should” want instead of what truly matters to us. We got into values, decision-making, comparison, and even when quitting is the right move. This episode i...

If you want to improve your leadership and identify your blind spots, take Kristiana’s free leadership audit here: https://worthytolead.co/audit

In this episode, I sit down with Kristiana Corona to unpack what real leadership actually looks like as you grow your business. We talk about the blind spots that hold leaders back, why your team might not be telling you the truth, and how ego can quietly limit your growth. I share my own experiences in leadership, and we break down simple frameworks you can use immediately to become more self-aware, build trust with yo...

In this episode, I sat down with Dr. Pam Theriot to break down something I didn’t even realize was affecting my performance—my eyesight. We talked about how screen time is crushing our productivity, causing brain fog, and even impacting our mental health. I learned that something as simple as blinking, taking short breaks, and managing screen exposure can dramatically improve focus and energy. If you’re an entrepreneur who spends hours in front of a screen and feels drained, this conversation might completely change how you approach your day.

‍️ About Dr. Pam Theriot

Dr. Pamela...

In this episode, I sat down with Josh Troy to break down what actually scales a business beyond just “getting better at sales.” We dive into why most entrepreneurs stay stuck in founder-led sales, how systems and operations are the real drivers of growth, and the exact metrics and frameworks you need to build a scalable sales team. Josh also shares how AI is changing the game in sales operations and how to think about hiring, efficiency, and profitability at a much higher level. If you want to move from hustling for deals to building a true revenue machine, this...

If you’re a small to mid-sized business and you’re serious about growing, go check out https://www.sparomarketing.com and connect with Molly directly.

n this episode of Entrepreneur DNA, I sit down with Molly Lopez, founder of Sparrow Marketing, to break down what actually works in advertising today and what most business owners are getting completely wrong.

Molly shares her journey from working with massive brands like Royal Caribbean and Lennar to building an agency that helps small and mid-sized businesses access big-budget marketing strategies without the massive spend.

We dive...

In this episode, Justin sits down with visionary founder Paul Allen, the mind behind Ancestry.com, to unpack the real lessons behind building, scaling, and exiting a billion-dollar company—and why the future of entrepreneurship will be radically different.

Paul shares his unconventional journey from academia to entrepreneurship, revealing how a background in education and information systems led him to build one of the most recognizable platforms in the world. He dives into the early days of digitizing knowledge before Google existed, the creation of Ancestry.com, and the overlooked opportunity of MyFamily.com—a platform that coul...

Get Glenn’s book Now What?, follow the Now What? Podcast on Apple, Spotify, and YouTube, and learn more through Sharp Leadership Development. https://a.co/d/0cZgPkLx

In this episode, I sit down with Glenn Sharp, founder of Sharp Leadership Development, to discuss how entrepreneurs can achieve greater business success. We explore essential leadership skills and strategies for improving efficiency within organizations. Glenn shares insights from his work with over 20,000 managers, providing valuable professional development advice for anyone looking to refine their management skills and leadership training.

About Glenn Sharp:

Glenn has ne...

In this episode, I sit down with CPA CJ Tarantino to break down how entrepreneurs and high-income earners can use real estate and smart tax strategies to legally reduce what they owe. We get into depreciation, cost segregation, and how bonus depreciation can create massive write-offs in year one. We also talk about the difference between passive and active income, how short-term rentals can unlock tax advantages, and why most people are overpaying simply because they aren’t planning ahead. If you’re serious about keeping more of what you make, this is a conversation you need to hear.