Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

Are you constantly pushing forward, convinced that stopping means failing? In this episode, we tackle the silent killer of entrepreneurial dreams: burnout. Nate Hebbert, founder of Selfware Consulting, shares his harrowing journey from a top-tier software engineer to being completely debilitated by burnout, and how he fought his way back. This isn't your typical "take a vacation" advice. Nate reveals a powerful framework for managing your energy, not just your time, so you can beat burnout without ever having to press pause on your ambitions. For any entrepreneur who feels like they're running on fumes, this conversation provides a practical, actionable roadmap to reclaim your energy, find joy in your work again, and build a sustainable path to success.
💡 What You'll Take Away For YOUR Business
Energy Management Over Time Management: Learn why the key to productivity isn't cramming more into your day, but identifying and cultivating activities that give you energy back.
The "Addition" Principle: Discover the counterintuitive strategy of adding energizing activities (like hobbies) to your life to prevent burnout, rather than cutting things out.
Optimize Your Drains: Get actionable tips on how to transform energy-draining tasks (like managing your inbox) into neutral or even energizing activities using frameworks like "What would this look like if it were fun?"
Early Warning Signs: Understand the subtle but critical symptoms of burnout—like chronic exhaustion and mental distance—so you can course-correct before it's too late.
The "Sharpen the Saw" Mentality: Reframe rest and personal projects not as distractions, but as essential maintenance required to achieve your biggest business goals.
Environment as an Energy Source: Realize how your physical surroundings (your home, your office) are constantly draining or fueling your energy, and how to optimize them.
📝 About Nate Hebbert 
Nate Hebbert is the founder and CEO of Selfware Consulting, an organization that empowers tech companies and entrepreneurs to beat burnout without sacrificing momentum. A former software engineer for giants like 3M and KPMG, Nate experienced a severe, career-halting burnout that forced him to re-evaluate everything. This personal crisis became his professional mission. Combining his analytical engineering mindset with a deep understanding of personal development, Nate developed a unique system of "energy management" to help high-performers thrive sustainably.
🎯 Nate’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs 
"You need to redefine the word 'important' in your life."
📢 Memorable Quotes
“It's if I don't do all of these things that are really bringing the energy in my life, then I might burn out. So it's almost the opposite.” – Nate Hebbert
“For any activity, ask yourself: What would this look like if it were fun?” – Nate Hebbert
"The people that we care about in our lives, that's the tree. And our jobs that we really want to succeed in, that's the tree... The activities that we do like going to the gym or playing a video game or reading a book, that's sharpening the saw." – Nate Hebbert
🔗 Links & Resources
Visit Selfware Consulting’s website
Connect with Nate on LinkedIn
Follow Selfware Consulting on LinkedIn
Follow Selfware Consulting on YouTube

In a special episode recorded on the move in a Cybertruck, Brian is joined by his friend and founder of Arrowhead Strategy Group, Jarome McKenzie. Jarome shares the powerful entrepreneurial mindset he demonstrated during a 2.5-hour tennis match where he lost every single set 6-0, yet grew more confident with every game. This conversation is a masterclass in resilience, revealing how to find breakthroughs in failure and why the most important work you do happens before your business day even starts. For any entrepreneur feeling stuck or afraid of setbacks, Jarome’s insights on preparation, reflection, and "keeping the ball in play" provide a game-changing perspective on building a sustainable and successful business.
💡 What You'll Take Away For YOUR Business
🎾 The "Keep The Ball in Play" Strategy: Discover why consistent, steady effort in your business is more effective than constantly chasing huge, risky “winners” like viral posts or massive product launches.
🧠 How to Gain Confidence from Failure: Learn the mental framework that allows you to see every setback not as a loss, but as a lesson that builds your confidence and skill set for the next challenge.
⚾️ Stealing Genius from Other Fields: Understand how to borrow lessons and strategies from completely unrelated areas of your life (like sports or hobbies) to innovate and solve problems in your business.
☀️ Winning Before the Day Begins: Unpack the immense value of morning reflection and visualization, and why your preparation is the single most important input for your business outcomes.
📈 The Power of Small, Intentional Tweaks: See how focusing on making 1% improvements and being intentional with every action can lead to massive growth over time.
💪 From Brute Force to Smart Strategy: Hear the story of shifting from trying to hit home runs to capitalizing on your opponent’s (or the market’s) mistakes through patience and smart positioning.
📝 About Jarome McKenzie
Jarome McKenzie is the founder of Arrowhead Strategy Group, an agency dedicated to helping entrepreneurs find clarity, answers, and hidden growth opportunities within their business numbers and finances. A former college baseball player, Jarome brings a unique, athletic-minded discipline and a deeply reflective nature to the world of business. He excels at breaking down complex challenges into their core components and applying universal principles of success, making him a brilliant strategist for any entrepreneur looking to master the fundamentals and achieve sustainable growth.
📢 Memorable Quotes
“I actually got more confident each time I lost… each game, each set, I learned something and got a little better each time.” – Jarome McKenzie
“If you're not growing, you're dying… and that is something that I believe for business, life, everything.” – Jarome McKenzie
"The most important input that I do every day… is not anything to do with what I do during the business day. It's all in the mornings before any of that starts." – Jarome McKenzie
🔗 Links & Resources
Website: arrowheadstrategygroup.com
LinkedIn: Connect with Jarome on LinkedIn. He loves connecting with and serving fellow entrepreneurs

In an era dominated by AI hype, how do you move from simply talking about AI to securely and profitably implementing it? This episode tackles that exact question with Evan Glaser, founder of Alongside AI and an expert at the intersection of AI, cybersecurity, and business strategy. Evan demystifies the world of powerful AI agents, explaining both their groundbreaking potential and the critical security risks they pose. This isn't just a theoretical discussion; it's a practical guide for entrepreneurs who want to leverage cutting-edge AI without compromising their data, their customers, or their company's future. Tune in to learn how to bridge the gap between AI experimentation and real-world, production-ready systems that give you a competitive edge.
💡 What You'll Take Away For YOUR Business
How to safely experiment with powerful new AI agents without exposing your sensitive business data.
Why the barrier to entry for building software and applications has never been lower (and how to leverage it even if you can't code).
The crucial difference between AI hype and production-ready systems that deliver real business value.
What "Responsible AI" actually means and why it's a critical framework for protecting your company and your customers.
How to think like a cybersecurity expert when adopting new AI tools to avoid common (and costly) mistakes.
A glimpse into the future of AI hardware and how it will fundamentally change the way we interact with technology and each other.
Why waiting for a major AI "disaster" to take security seriously is a losing strategy for any business.
📝 About Evan Glaser 
Evan Glaser is the founder and CEO of Alongside AI, a firm dedicated to helping organizations implement AI securely and effectively. With a rich background in cybersecurity, AI governance, and enterprise consulting, Evan specializes in bridging the gap between technical execution and business strategy. His unique expertise allows him to guide leadership teams in reducing AI-related risks while accelerating real adoption. Evan brings a practical, security-first perspective to the AI conversation, making him an essential voice for any entrepreneur looking to innovate responsibly.
🎯 Evan’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs 
"The barrier to accomplishing different tasks has never been lower. If you have a vision for a product or a service... that you have been limited in doing based on your skill set... I would really urge you to revisit them."
📢 Memorable Quotes
"With great power comes great responsibility, and I think that some of us who have spent more time and energy in these security, data privacy, and AI governance domains, maybe some of those risks become more evident." – Evan Glaser
"You can't, in my experience, ever draw a firm line in the sand and say, 'This facet of technology will never work.' ...it really pays to be willing to revisit your priors." – Evan Glaser
"AI is not coming. It's already here. These tools have really changed the way I live and changed the way I'm able to conduct business." – Evan Glaser
🔗 Links & Resources
Visit Alongside AI’s website
Connect with Evan on LinkedIn
Follow Alongside AI, LLC on LinkedIn

In an era of shiny objects and AI shortcuts, 25-year marketing veteran Scott Orth joins the show to bring us back to the fundamentals that actually grow a business. This episode is a masterclass in building a holistic digital presence, proving that a solid foundation in SEO and strategic paid ads will always outperform chasing the latest trend. Scott breaks down why simply being on Google isn't enough; you need to dominate it from every angle—organic results, maps, and ads—to truly capture your audience.
This episode is invaluable for any entrepreneur tired of marketing strategies that don't move the needle. You'll learn how to transform your website from a static brochure into a lead-capturing machine, the right way to leverage AI as an assistant (not a replacement for human creativity), and how a powerful CRM can automate your follow-up so you never lose a potential customer again. Scott’s deep experience provides a clear, actionable roadmap for increasing visibility and driving real growth.
💡 What You'll Take Away For YOUR Business
🚀 The Modern "Omnipresence" Strategy: Why showing up in organic search, paid ads, and maps simultaneously is the new "TV, radio, and billboard" for dominating your market.
📝 Content That Converts: Learn why a blog is non-negotiable in 2026 and how to use it to answer long-tail search queries that your competitors are ignoring.
🤖 AI as Your Assistant, Not Your Author: Discover the right way to use AI for content creation—to build frameworks and generate ideas—and why 100% AI-generated posts fail to rank.
🤝 The Powerful Marriage of Paid & Organic: Understand how to use paid ads to fill the gap while your SEO builds momentum, creating a two-pronged attack for consistent lead flow.
⚙️ Why a CRM is Your Business's Central Hub: Learn how a CRM combined with automation can capture missed calls, instantly follow up with inquiries, and keep you from losing leads to competitors.
📝 About Scott Orth
Scott Orth is an SEO and digital growth expert with 25 years of hands-on experience in the trenches of online marketing. As the founder of Thrive Business Marketing and the creator of Surge by Thrive, he has mastered the art of combining timeless marketing fundamentals with cutting-edge technology. Scott got his start back in 1999, paying for clicks when they were a penny apiece, and has since evolved into a full-stack marketing authority who helps businesses build a powerful, holistic online presence that drives measurable results.
🎯 Scott’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Things don't have to be perfect. Get out there, get it done. You're going to learn as you go."
📢 Memorable Quotes
“You've got to have posts that are written, I say for a human, by a human... a search engine is going to pick up on that and rank you better for that than if you just grab an AI post and throw it on your blog.” – Scott Orth
"How much more likely are you as a business going to get that lead or that sale than your competitor who maybe only shows up in one of those places? You're at least four times more likely because you're showing up four times instead of one.” – Scott Orth
🔗 Links & Resources
Visit Thrive Business Marketing’s website
Visit Surge’s website
Connect with Scott on LinkedIn
Follow Thrive Business Marketing on LinkedIn
Follow Surge by Thrive on LinkedIn

In this episode, Connor O'Hearn completely reframes how entrepreneurs should view artificial intelligence. He introduces the game-changing concept of AI as a "navigation system for business"—a dynamic, layered GPS that guides you through complex decisions, rather than just being another static tool. For wantrepreneurs and entrepreneurs, this episode is a masterclass in leveraging AI to fill skill gaps, process overwhelming amounts of data, and make smarter, faster decisions. Connor’s unique journey from sales and geography to co-founding an AI strategy firm gives him a powerful perspective on how technology can enhance human intuition and democratize the tools previously reserved for massive corporations.
💡 What You'll Take Away For YOUR Business
The "Business GPS" Mindset: Learn to view AI not as a chatbot, but as a strategic navigation system that synthesizes data layers to show you the best path forward.
Bridge Your Skill Gaps Instantly: Discover how AI can act as your personal expert in areas you’re weak in—from financial modeling to coding—allowing you to operate like a multi-talented founder from day one.
Capitalize on the "Silver Tsunami": Understand the historic opportunity to acquire and modernize small businesses from the retiring baby boomer generation, using AI as your unfair advantage.
Enhance, Don't Replace, Your Intuition: Find out how to use AI as a "thought partner" to validate your gut feelings with data, empowering you to make bolder, more informed bets.
Achieve Presence and Build Better Relationships: Learn how simple tools like AI note-takers can free your mind during meetings, allowing you to be fully present and build deeper connections with clients and partners.
Compete with Giants on a Startup Budget: See how a small team can now achieve what once required tens of thousands of dollars and a large staff, simply by using the right AI tools.
📝 About Connor O'Hearn
Connor O'Hearn is the co-founder of an AI strategy firm dedicated to helping business leaders navigate increasingly complex decisions. With a diverse background spanning business, entrepreneurship, aviation, and even geography, Connor brings a uniquely human-centric approach to the world of technology. His experience in an early-stage startup, where he helped lead a strategic partnership with Microsoft's co-pilot ecosystem, gave him a front-row seat to the AI revolution. Today, he channels that expertise into building a true "navigation system for business," empowering entrepreneurs to turn data chaos into clear, actionable strategy.
🎯 Connor’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
Know what you're really good at, double down on that strength, and then use AI without fear to fill in all the gaps and deficiencies you have as an entrepreneur.
📢 Memorable Quotes
“That nurture folder is where deals go to die.” – Connor O'Hearn
“When you leave a meeting, it takes like one hour later, you've lost 50% of the memory of that conversation. And it just continues to degrade. If you wait 24 hours to go make those notes, you're down to like 10 or 5% of the actual conversation.” – Connor O'Hearn
“Don't get too comfortable because the chaos of how fast everything is changing. You can either look at it as chaos or I think start to see the patterns in it.” – Connor O'Hearn
🔗 Links & Resources
Visit Maai’s website
Connect with Connor on LinkedIn
Follow Maai on LinkedIn