Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

Latest Episodes:

1511: Scaling Remotely: The SOPs That Power a National Expert Network w/ Wendy Votroubek + Julie Davenport Jul 10, 2026

Show notes

Ever wondered if your professional expertise could become a thriving business? In this episode, we sit down with Wendy Votroubek and Julie Davenport, the powerhouse duo behind Integrity Legal Nurse Consulting PDX. Wendy, a nurse with over 30 years of experience, transformed her deep medical knowledge into a nationwide consulting firm that bridges the gap between medicine and law. This episode is a masterclass in turning a specialized skill into a scalable, remote-first business. Wendy and Julie pull back the curtain on how they built a rock-solid infrastructure using Standard Operating Procedures (SOPs), the power of investing in business coaches, and why doing "unscalable" things like sending handwritten notes is their secret to winning and keeping high-value clients. If you're looking to build a business with a strong foundation and scale your impact, this conversation is packed with actionable wisdom.

💡 What You'll Take Away For YOUR Business

Turn Your Expertise into a Business: Learn how Wendy leveraged 30+ years of nursing experience to create a unique and in-demand consulting service for attorneys.
The Power of SOPs for Scaling: Discover why creating detailed Standard Operating Procedures from day one is crucial for building a remote team and ensuring consistent, high-quality work.
Invest in Yourself to Grow: Hear why Wendy has hired a business coach since the very beginning and how investing in mentors, your team, and yourself is the fastest path to success.
Mastering Client Relationships: Learn why "old school" tactics like prompt email replies and handwritten thank you notes are non-negotiable for building loyalty and generating word-of-mouth referrals.
Building a Remote-First Team: Get an inside look at how to successfully onboard, mentor, and manage a nationwide network of subcontractors to serve clients across the country.
The 90-Day Sprint Strategy: Understand how setting intentional goals every quarter and practicing gratitude can transform your mindset and drive massive business growth.
Embracing an "It Takes a Village" Mentality: See why the most successful entrepreneurs shed their ego, hire people smarter than them, and build a team of experts to handle marketing, bookkeeping, and finance.

📝 About Wendy Votroubek + Julie Davenport

Wendy Votroubek is the founder of Integrity Legal Nurse Consulting PDX, a firm she started in 2010 to help attorneys nationwide build stronger cases through expert medical analysis. With over 30 years as a registered nurse and three published nursing textbooks, Wendy is a true expert at translating complex medical data into clear, compelling narratives. Julie Davenport brings 8+ years of clinical and leadership experience to her role as Operations Manager, where she helps scale the company’s systems and nationwide team. Together, they lead a team of nurses who provide invaluable insights for legal cases, demonstrating how deep professional expertise can be the foundation of a powerful and impactful business.

🎯 Wendy’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"Surround yourself by people who know more than you... I'm not worried about hiring nurses that are smarter than me. I embrace the fact that those nurses are intelligent in what they do."

🎯 Julie’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"I think ego or thinking that you know it all is the absolute downfall... Be humble and grateful when asking for that help because you can't do it all and it really takes a village."

📢 Memorable Quotes

"I think as business owners, we all think that it's all on our shoulders... When you expand your team and invest in yourself, you don't have to do it yourself. You have access to other people's brains.” – Wendy Votroubek
“Uncertainty is just a part of it. So then embracing the uncertainty and realizing that you can get to the other side of it.” – Wendy Votroubek
"...we do things like handwritten thank you cards, gifts for certain holidays for our clients to really maintain that, that relationship." – Julie Davenport
"The human element is still very important to us and very important to a lot of our clients. And as of now, AI is not permissible in the courtroom. So as far as our nurses that do expert work and give their opinions and actually testify in court, AI can't replace that." – Julie Davenport

💡 Actionable Takeaways

Systematize Your Core Processes: Start documenting your workflows today. Create Standard Operating Procedures (SOPs) for your most common tasks to ensure quality and make future hiring seamless.
Set 90-Day Goals: Ditch the overwhelming annual plan. Break your vision down into quarterly goals to create focus, build momentum, and track progress more effectively.
Do Something Unscalable: This week, send a handwritten thank you note or a thoughtful gift to a key client. Small, personal gestures build powerful, lasting relationships.
Identify Your Next Hire: Make a list of tasks you shouldn't be doing. Your next step is to find someone smarter than you at those tasks and bring them onto your team, whether as a contractor or employee.
Seek Out a Mentor: Find a business coach or a thought leader in your industry. As Wendy proves, investing in outside guidance is a shortcut to overcoming challenges and accelerating growth.

🔗 Links & Resources

1510: From Soldier to SpaceX to Solving a 100-Year-Old Problem w/ Kevin Damoa Jul 09, 2026

Show notes

In this powerful episode, we sit down with Kevin Damoa, a true force of entrepreneurial energy and innovation. Drawing from over two decades in high-stakes logistics—from combat tours in Iraq to managing flight modules at SpaceX—Kevin is now tackling one of the biggest challenges in modern freight. He founded Glīd Technologies to solve the century-old, broken handoff between road and rail, building an entire ecosystem of autonomous vehicles and AI software from the ground up. This episode is a masterclass in founder mentality, showing you how to identify and solve massive societal problems, integrate complex systems, and maintain unwavering focus on your mission. Tune in to learn how to think like an innovator, embrace failure as fuel, and build a business that truly moves humanity forward.

💡 What You'll Take Away For YOUR Business

How to identify and tackle a century-old problem with a first-principles approach, even when others say, "that's how it's always been done."
The power of integrating hardware, software, AND people to create a complete ecosystem solution that competitors can't touch.
Real-world lessons from bootstrapping for three years and how to navigate the "drought" before finding the right funding and partners.
How to adopt a military and SpaceX mindset to fail fast, learn from your losses, and continuously readjust your strategy to keep moving forward.
The critical importance of building for your community and why making them the first and last thing on your mind is key to long-term success.
Why waiting for perfection is the enemy of progress and how to find the courage to take action on your vision NOW.
How to stay focused on your core mission and see opportunity (tailwinds) even amidst macroeconomic turmoil and geopolitical tensions.

📝 About Kevin Damoa

Kevin Damoa is the founder and CEO of Glīd Technologies, a visionary company connecting the nation's roads and rails into a single, seamless logistics network. His journey began at age 17 when he enlisted in the US Army, completing two combat tours in Iraq specializing in railhead logistics. After 12 years in the military, he brought his expertise to the private sector, managing logistics for SpaceX's interplanetary ambitions and the F-35 program at Northrop Grumman. As the founder of a certified service-disabled veteran-owned small business and winner of the 2025 TechCrunch Disrupt Startup Battlefield, Kevin brings a unique, battle-tested perspective on solving massive problems with strategy, grit, and an unwavering commitment to moving the world forward.

🎯 Kevin’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

“Stop waiting for perfection to come and smack you in the head and say, 'hey, I'm here.' It'll never come... Trust that the vision and the mission that you've set out to do, now is the time to actually do it.”

📢 Memorable Quotes

“I remember at SpaceX, we used to celebrate every launch and every blowup because there's victories and losses that are embedded in the lessons that are taught.” – Kevin Damoa
“Pay rent for your work here on Earth to support your community by the works of your hands. And that's exactly what I do. I do it by the work of my hands in order to move humanity forward.” – Kevin Damoa

💡 Actionable Takeaways

Stop waiting for the "perfect time." Identify one small, immediate step you can take on your business idea today and execute it.
Re-evaluate your business model. Are you solving just one piece of the puzzle (hardware OR software) when you should be building an integrated ecosystem?
Embrace failure as a learning opportunity. The next time something goes wrong, document the lesson learned instead of just focusing on the loss.
Schedule daily "executive time" to assess your financial health, track your plan's relevance, and maintain a clear mind through reflection or meditation.
Define your business's core mission and how it serves a specific community. Make that the central focus of your strategy and decision-making.

🔗 Links & Resources

1509: The AI Execution Gap: Why Big Companies Fail at AI (And How Small Businesses Can Win) w/ Robert Toshiyuki Morrell Jul 08, 2026

Show notes

In a world buzzing with AI hype, most enterprise-level projects are quietly failing. Robert Toshiyuki Morrell, founder of ThreddSync and an AI expert since 2009, joins the show to pull back the curtain on why this is happening and what entrepreneurs can learn from it. He breaks down the critical "execution gap" between AI strategy and real-world results, revealing why simply giving your team access to AI tools—a practice he calls "token sprinkling"—is a recipe for wasted investment. This episode is a masterclass for any wantrepreneur or entrepreneur looking to move beyond surface-level AI use and build a truly intelligent, efficient, and scalable business. Robert provides a practical framework for integrating AI deep into your business functions for maximum ROI, while also addressing the risks, governance, and the future of work.

💡 What You'll Take Away For YOUR Business

The Intelligence Layer Ladder: Learn a step-by-step framework for successfully adopting AI, moving from individual productivity hacks to deep, enterprise-level integration.
Why “Token Sprinkling” Fails: Understand why giving everyone access to ChatGPT isn’t a real AI strategy and how to avoid this common, wasteful mistake.
From Cost Center to Profit Driver: Discover how to tie every AI initiative directly to your core business KPIs, ensuring you get a tangible return on your investment.
De-Risk Your AI Adoption: Uncover the critical importance of governance, guardrails, and compliance in making AI reliable and avoiding the high failure rates plaguing the industry.
The Future of Your Team: Get a forward-looking perspective on how AI creates new roles focused on management and judgment, rather than simply replacing jobs.
Capitalizing on Macro Trends: Learn how the rise of the gig economy and the AI talent gap creates massive opportunities for savvy entrepreneurs.
Build Your Own AI Solution: Hear about ThreadSync's plan to release its internal tech stack, Solidarity, to empower more entrepreneurs and developers to build credible AI tools.

📝 About Robert Toshiyuki Morrell

Robert Toshiyuki Morrell is the founder of ThreddSync, an operator-led firm that helps enterprises deploy, manage, and scale AI. With a background that began in mathematics before pivoting to technology, Robert has been deeply involved in AI and machine learning since his graduate studies in 2009—long before it became a mainstream buzzword. His extensive experience consulting for companies from startups to the Fortune 500 gave him a unique insight into the "execution gap" that plagues AI adoption. This led him to found ThreddSync, a company that uniquely combines high-level advisory with hands-on execution to ensure AI initiatives deliver real, measurable business outcomes.

🎯 Robert’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

“Don't listen to the media. Turn off social media... play with the actual tools because that's really going to inform you what's truth versus what's hype.”

📢 Memorable Quotes

"80-85% of pilots fail... throughout all this time, we have not been able to solve this problem. And so clearly there's an execution gap." – Robert Toshiyuki Morrell
"We can automate the tasks away that we do individually each day, but one thing that we can't automate just yet is our judgment, our expertise, our knowledge." – Robert Toshiyuki Morrell
"You shouldn't look at AI like a technology upgrade... what that's creating is compressed timeframes for when new innovation is going to come to market." – Robert Toshiyuki Morrell

💡 Actionable Takeaways

Schedule AI Playtime: Block off one hour this week to experiment with an AI tool you haven't used before. Don't try to solve a business problem; just learn its capabilities and limitations.
Identify One Core Process to Improve: Instead of thinking about small tasks to automate, identify one multi-step process in your business (e.g., client onboarding, content creation) and brainstorm how AI could streamline communication and collaboration within it.
Map AI to a KPI: Before investing time or money into a new AI tool, write down exactly which business Key Performance Indicator (KPI) it will improve and how you will measure that improvement.
Create a Simple Guardrail: If you or your team use AI for content creation, establish a simple rule, such as "All AI-generated text must be fact-checked and edited by a human for brand voice before publishing."

🔗 Links & Resources

1508: This Founder Runs His Entire Company on an Army of AI Agents w/ Drew Mehta Jul 07, 2026

Show notes

Tired of hearing about AI as a vague, futuristic concept? In this episode, we pull back the curtain on what it really looks like to build and run a business on a fleet of AI agents. Drew Mehta, founder of ThinkFraction, joins us to share how he went from managing products for Major League Baseball and a $750B asset management firm to launching his own AI-native company. He doesn't just talk the talk; his company’s content, outreach, and research are all powered by AI agents he designed, with him as the "human in the loop." This episode is a masterclass in strategic AI implementation, teaching you how to stop chasing buzzwords and start solving real, costly business problems. You'll learn how to identify the right opportunities for automation, why human judgment is more valuable than ever, and how to gain a massive competitive edge without being a tech genius.

💡 What You'll Take Away For YOUR Business

How to Build Your Own AI Team: Learn the structure behind Drew’s "fleet of agents" that ideates content, drafts posts, and runs research, so you can replicate it in your business.
The #1 Mistake Businesses Make with AI: Discover why starting with the problem, not the tool, is the key to a positive ROI and avoiding costly over-engineering.
The "Intern" Framework for AI Risk: A simple but powerful mental model for deciding which tasks are safe to fully automate and where you absolutely need a human in the loop.
Deterministic vs. Probabilistic AI: Understand the crucial difference and when to use simple automation versus complex AI agents to save money and get better results.
Turning Operations into an Advantage: Learn why your internal processes and bottlenecks are the biggest untapped opportunities for leveraging AI to become faster and leaner than your competition.
Enhancing the Customer Experience with AI: See how AI can handle administrative tasks to free you up, improve response times, and create a better experience that wins you more customers.

📝 About Drew Mehta
Drew Mehta is the founder of ThinkFraction and a 20-year veteran product manager who has built solutions for some of the biggest names in sports and finance, including Major League Baseball and the global asset management firm KKR. A problem-solver by nature, Drew became fascinated with AI's potential to solve complex business challenges. Instead of just advising from the sidelines, he built his entire company, ThinkFraction, on a foundation of AI agents he directs. This unique, hands-on experience gives him a practical and grounded perspective on how any business can leverage AI to operate more efficiently and effectively.

🎯 Drew’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"The biggest thing that stops you now is yourself. So don't let that be the reason why you don't take a risk."

📢 Memorable Quotes

“Everyone else grabs the tool and goes hunting for the problem, whereas I start with the problem.” – Drew Mehta
"You don't want to bring a machine gun to a pillow fight... Point AI at something a simple rule could have handled and you're paying a premium to do the job worse.” – Drew Mehta
"If you're not willing to let an intern do something, then I wouldn't let an AI do it either, especially with the stakes of your business." – Drew Mehta

💡 Actionable Takeaways

Identify Your Biggest Time Sink: For one week, track your tasks and identify the single most repetitive, time-consuming operational activity in your business. This is your first candidate for AI automation.
Apply the "Intern Test": Before automating a customer-facing or high-stakes process, ask, "Would I let a new intern handle this without my final approval?" Use the answer to decide where the "human in the loop" is non-negotiable.
Focus on a Workflow Problem First: Don't try to change your core product or service with AI. Instead, look for a workflow bottleneck, like lead intake or invoicing, and solve that first for a quick, measurable win.
Start with Simple Rules, Not Complex Agents: Before building an entire agentic system, see if a simple, rule-based automation (like an "if-then" workflow) can solve 80% of the problem.

🔗 Links & Resources

1507: This 14-Year-Old Founder is Making AI Accessible (and Bespoke!) for Your Small Business w/ Margo & Nate Shulman Jul 06, 2026

Show notes

In an era where AI can feel like a tool reserved for giant corporations, Margo and Nate Shulman are leveling the playing field. In this episode, the dynamic mother-son co-founding team behind NATEX AI pulls back the curtain on how they’re building truly bespoke AI solutions that deliver enterprise-level power to small and mid-sized businesses. They reveal why a "vertical" approach to solving industry-specific problems—from healthcare insurance denials to subcontractor workflows—is the key to creating massive value. This episode is a masterclass in how combining wildly different perspectives and skill sets can create an unstoppable entrepreneurial force, proving that you don't need a massive budget to harness the power of AI—you just need the right mindset.

💡 What You'll Take Away For YOUR Business

🚀 Why a "vertical" business model beats a "horizontal" one, allowing you to become an indispensable resource for a specific niche.
🤖 How to build truly bespoke AI solutions that address the unique DNA of your customers, creating immense value and loyalty.
🤝 The power of a co-founding team with complementary skills and diverse backgrounds to innovate and solve complex problems.
💰 How to identify and automate administrative pain points in any industry, freeing up resources to focus on growth and customer experience.
🧠 Why AI is a tool to enhance human capability, not replace it, and how to implement it in a way that is non-intrusive and highly effective.
💡 How to make cutting-edge technology accessible and affordable for smaller businesses, opening up a massive and underserved market.
📈 Why now is the time to start learning and implementing AI in your business, and how surprisingly easy it is to get started.

📝 About Margo & Nate Shulman

Margo and Nate Shulman are the brilliant co-founders of NATEX AI, a company on a mission to democratize artificial intelligence for small and mid-sized businesses. Margo is a world-class business attorney whose journey took her from being a professional flutist in Leningrad to the highest echelons of big law and the Big Four. Her immigrant mindset and deep analytical business expertise provide the strategic foundation for their work. Nate, at just 14 years old, is a prodigy in the AI space, having developed a deep, self-directed passion for technology and coding from a young age. Together, their unique blend of seasoned business acumen and cutting-edge technical skill allows them to create powerful, purpose-built AI solutions that solve real-world problems.

🎯 Margo’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"Allow yourself to think in ways that you may not have previously thought... Realize AI is not going anywhere, it's here to stay. How can I, as a professional, as a human being, utilize it to the best possible way for myself?"

🎯 Nate’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"AI is insanely easy to start... If you're not very well-versed in AI, you're going to start falling behind and nobody wants that. So I think that's the number one thing a lot of people should think about."

📢 Memorable Quotes

"If you're doing it really horizontally, you really don't have the resources to improve your product in a measurable way... it's that saying, jack of all trades, master of none." – Nate Shulman
"It's always human in the seat, meaning that all the judgmental decisions, all the final calls are done by humans. Especially in our product." – Margo Shulman
"Since AI is the future, you really got to figure out a way to implement it correctly or else you're kind of going to get outpaced." – Nate Shulman
"It's a tool... to make your life a little better, but not to take over your life, as with all the technologies." – Margo Shulman

💡 Actionable Takeaways

✅ Start today by experimenting with a free AI chat interface to understand its basic capabilities and how you can use it for simple tasks.
✅ Identify one major administrative bottleneck or repetitive task in your business that could potentially be automated with a simple AI workflow.
✅ Reframe your thinking about AI from a "job replacer" to a "human enhancer" that improves customer experience and employee efficiency.
✅ Seek out a business partner or collaborator whose skills are the polar opposite of yours. Combine your strengths to create something truly innovative.
✅ Talk to potential customers in a specific niche to uncover their biggest "pain points" and brainstorm how a focused, vertical solution could solve them.

🔗 Links & Resources

1506: The declaration did NOT come with independence... Jul 05, 2026

Show notes

Happy 4th of July! On this historic 250th anniversary of the United States, Brian Lofrumento shares a powerful and timely lesson for every entrepreneur and wantrepreneur. What if the most important part of the 4th of July story isn't the victory, but the declaration that came before it? In this Solo Sunday episode, Brian reveals a profound parallel between the Declaration of Independence and the entrepreneurial journey. He explores why true success doesn't start with results, but with a bold, public declaration of who you are and what you're building — long before the world agrees with you. This isn't just a history lesson; it's a call to action to stop waiting for proof and start declaring your own independence.

✨ Why This Matters for You

This mindset shift is the key to unlocking your entrepreneurial potential:

It frees you from the "tyranny of being picked" — no more waiting for a boss, a client, or an investor to give you permission.
It creates an identity shift, forcing you to act, decide, and commit like the founder you want to become.
It teaches you that commitment precedes results. The declaration is what fuels the fight, not the other way around.
It’s the ultimate antidote to imposter syndrome, because you're not trying to convince yourself; you're announcing who you already are.

📝 Key Takeaways

Declaration Precedes Independence. The Founding Fathers declared their independence while still in the middle of the fight. As an entrepreneur, you must declare your new identity before you see the results.
Pick Yourself. As author Seth Godin says, so much of life is about waiting to be picked. Entrepreneurship is the ultimate act of picking yourself.
Commitment, Not Consideration. Your journey doesn't start when you're "exploring" or "testing the waters." It starts with a definitive statement: "This is who I am now."
Announce Who You Already Are. A true declaration isn't about faking it. It’s about embodying the identity of an entrepreneur and letting your actions catch up to your commitment.
Celebrate the Declaration. We celebrate the day the declaration was made, not the day the war was won. This shows the immense power of that initial, committed choice.

🚀 Put It Into Action

This week, make your own Declaration of Independence:

Ask yourself Brian's question: "What declaration have you been postponing because you're waiting for proof?"
Write it down as a declarative statement. Not "I want to be..." but "I am a founder. I am a CEO. I am an entrepreneur."
Take one action today that aligns with that declaration. What would the person you just declared yourself to be do right now? Do that.

🔗 Stay Connected

Subscribe to the show so you never miss an episode.
Connect with Brian on Instagram @imetbrian.
Share this episode with a fellow entrepreneur who needs to stop waiting and start declaring their own vision for the future.

1505: Why This Top Engineer Says Your Business Isn't a Marathon w/ Maxim Kheyfets Jul 03, 2026

Show notes

In this episode, Brian sits down with Maxim Kheyfets, a brilliant founder with a rare blend of deep engineering expertise and a profound understanding of the human element in business. Maxim shares his journey from scaling major startups like Clear and Bread Finance to launching his own venture, AnyIntelli. He breaks down why process, not just technology, is the key to scalable growth in today's AI-driven world. This episode is a masterclass for any entrepreneur who wants to build resilient systems, foster effective teams, and adopt the long-term "infinite game" mindset required for sustainable success. Tune in to learn how to think like an engineer to build a business that lasts.

💡 What You'll Take Away For YOUR Business

🚀 Why focusing on process first allows you to scale your team, technology, and operations effectively when growth hits.
🤖 A refreshing perspective on AI: Why it’s an opportunity that enhances human expertise rather than a threat that replaces it.
⚙️ The "Execution as Code" methodology: How to build a practice around your business that makes onboarding and decision-making more efficient.
🧠 How to apply systems-thinking from engineering to create a more resilient and predictable business organization.
📈 The surprising limiting factor that holds most businesses back (Hint: It’s not access to technology or capital).
⏳ Why treating your business as an "infinite game" instead of a sprint is the key to avoiding burnout and achieving long-term vision.
💡 How to find massive opportunities by solving problems in established markets, inspired by the unlikely origin story of IKEA.

📝 About Maxim Kheyfets

Maxim Kheyfets is the founder of AnyIntelli, a practice focused on SaaS software automation and building elastic environments for digital ventures. With a distinguished career as a DevOps, software, and data engineer, Maxim played a pivotal role in scaling startups like Clear and Bread Finance into public companies. His expertise lies in building high-performance, secure, and scalable systems, but his unique perspective is his deep appreciation for the human dynamics and processes that make technology truly effective.

🎯 Maxim’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"Business is not even a marathon... It's an infinite game."

📢 Memorable Quotes

“In order to change and fulfill 1% which is left, you still need to understand well 100%, especially in those environments where you move money, where you are responsible for security, where you're responsible for the health of the patient.” – Maxim Kheyfets
“None of those companies can move forward without a group of 1, 2, 3 people who sit together, figure out how we all operate… and what is the next step to move forward.” – Maxim Kheyfets
“The largest limiting factor is knowing that problem exists, especially for software engineers.” – Maxim Kheyfets

💡 Actionable Takeaways

✅ Adopt an "infinite game" mindset to guide your daily decisions, focusing on sustainability over short-term sprints.
✅ Document your core business processes now, even if you’re a solo founder. This creates a foundation for your future team to improve upon, not invent from scratch.
✅ Instead of fearing AI, ask your team: "How can we use this tool to understand our core work better and solve bigger problems?"
✅ Identify your biggest challenge (like sales) and approach it like an engineering problem: break it down, learn the system, and build a process to solve it.

🔗 Links & Resources

1504: How to Vet a Business Like a Private Equity Pro (Before You Buy It) w/ Carter Micklem Jul 02, 2026

Show notes

Ever dreamed of buying a business but felt completely out of your depth? This episode is your masterclass in demystifying the world of business acquisition. Carter Micklem, a former private equity VP, pulls back the curtain on the due diligence process, sharing the exact strategies institutional investors use to vet a company—and how you can apply them to your first (or next) purchase. He breaks down the difference between buying a business and starting a franchise, the critical data points to analyze, and why understanding the seller’s day-to-day role is the most overlooked factor in any deal. This isn't just theory; Carter used this exact playbook to leave his high-powered finance job and acquire his own successful lawn equipment dealership, which ultimately inspired him to launch The Diligence Pros. Tune in to gain the confidence and competence to make the biggest investment of your life the right way.

💡 What You'll Take Away For YOUR Business

How to think like an institutional investor by starting with your criteria first, not the specific business.
The key difference between buying a business (instant cash flow) and buying a franchise (a starter pack with strings attached).
A breakdown of "operating due diligence" and why analyzing customer data, product margins, and employee roles is more important than just reviewing tax returns.
Creative deal structuring secrets, like seller notes and earnouts, that can lower your upfront cash investment.
Why the seller’s day-to-day involvement is the single biggest risk factor in a small business acquisition and how to properly assess it.
How to remove emotion from the buying process to make objective, data-driven decisions that protect your investment.
The step-by-step process for taking calculated risks, from starting a small side hustle to acquiring a multi-location business.

📝 About Carter Micklem

Carter Micklem is the founder of The Diligence Pros, a firm dedicated to helping entrepreneurs conduct institutional-grade due diligence when buying a business. He began his career in private equity, rising to Vice President where he led the investment and underwriting for numerous private companies. Feeling the entrepreneurial itch himself, Carter left the corporate world to acquire his own small business—a lawn equipment dealership in North Carolina. This firsthand experience of applying his high-level finance skills to a main-street business purchase gave him the unique perspective and inspiration to help other entrepreneurs navigate the acquisition process with confidence.

🎯 Carter’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

“Take the calculated risk. Do your research… but, you know, take the risk. I think getting out of the corporate world is night and day. Once you kind of make it to the other side, you can't imagine yourself going back.”

📢 Memorable Quotes

“Ultimately you're buying a business. Even if you're going to be the operator and it's your career, it's still the biggest investment you're ever going to make.” – Carter Micklem
“We're not here to look for smoking guns, skeletons in the closet, or a rocket ship that the seller doesn't know about... It's more of a mosaic, you know, a lot of little pieces. Ultimately, you zoom out and you see the whole picture.” – Carter Micklem
“You can't just trust because the bank approved you that you can afford that capital structure, or that that's a good idea to sign up for that.” – Carter Micklem

💡 Actionable Takeaways

If you're looking to buy a business, start networking with local business brokers in your target area instead of just browsing online marketplaces like BizBuySell.
When evaluating a business, go beyond the financials. Ask for operational data like customer lists, sales by product, and vendor agreements to analyze trends.
Before signing an LOI, spend significant time understanding the current owner’s daily tasks. Assess how much of the business's success is tied directly to them.
To de-risk your entrepreneurial journey, start a small-scale side business that requires a minimal investment to build your confidence and business acumen.

🔗 Links & Resources

1503: This Founder Turned Relationship Frustration Into a Wellness App Disrupting the Industry w/ Lisa Virginia Anderson Jul 01, 2026

Show notes

Ever felt like the thankless tasks you do for others go completely unnoticed? Lisa Virginia Anderson, a former senior director at Planned Parenthood and reality TV producer, turned that exact feeling into a disruptive tech company. In this episode, she shares the origin story of InvisiBILL, a subversive wellness app that uses AI to assign a real dollar value to the invisible and relational labor that keeps our lives running. This isn't just about getting credit; it's a masterclass in creating a new market category from a personal pain point. For any entrepreneur who's been told their idea is too “out there,” Lisa’s journey proves that the most disruptive solutions often start with a moment of frustration and the courage to build something the world has never seen before.

💡 What You'll Take Away For YOUR Business

How to transform a moment of personal frustration (the infamous “cat pee” incident) into a scalable and disruptive business concept.
The strategic power of leaning into a controversial word like “petty” to create an unforgettable brand that cuts through the noise.
Why assigning a quantifiable dollar value to an intangible concept can unlock an entirely new market and conversation.
How to use AI not just for efficiency, but to create a “story correction engine” that reframes value for your users.
The ultimate validation: Why building and shipping your product is the most effective way to silence doubters and attract your true audience.
How your product can evolve beyond your initial target demographic and find surprising use cases you never imagined.

📝 About Lisa Virginia Anderson

Lisa Virginia Anderson is the solo founder of InvisiBILL, a groundbreaking wellness app that quantifies invisible relational labor. With a dynamic background that spans from producing hit shows like Project Runway at Lifetime Television to serving as the Senior Director of Strategic Operations at Planned Parenthood Los Angeles, Lisa brings a unique blend of creative storytelling and social justice to the tech world. She is a true disruptor, driven by the belief that we need to fundamentally change the way society values the work that happens beyond the balance sheet.

🎯 Lisa’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"Understanding which feedback to listen to and which feedback is important and which feedback to disregard is… one of the biggest skills that you can learn."

📢 Memorable Quotes

“I privately call InvisiBILL a ‘story correction engine’ because what I really wanted to do is create a world where we assign value when you do things for other people, things that are beyond yourself.” – Lisa Virginia Anderson
“You have to be out of your f***ing mind. I can't send my husband an invoice for cleaning up cat pee. That's crazy.” – Lisa Virginia Anderson on the initial reaction to her idea
“Don't be deterred to build something and put it into the world because once you really build it and put it into the world… it's real and people start interacting with it. It's a real product and it's fantastic.” – Lisa Virginia Anderson

💡 Actionable Takeaways

Mine Your Frustrations: For the next week, keep a list of small, recurring annoyances or tasks you feel are undervalued in your life or work. Is there a potential business solution hidden in that list?
Embrace Your "Petty": Identify a word or concept in your industry that has negative connotations. Brainstorm ways you could flip it on its head and use it as a powerful, attention-grabbing part of your brand.
Build the "Crazy" Thing: Stop waiting for permission. Use no-code tools or hire a freelancer to create the simplest possible version of your idea and get it into the hands of a few potential users this month.
Practice Selective Listening: The next time you receive unsolicited advice about your business, consciously ask yourself: "Is this feedback from someone who understands my target user, or is it just their personal opinion?"

🔗 Links & Resources

1502: The "Bad Idea" That Birthed a $2M Supercar w/ Nikita Bridan Jun 30, 2026

Show notes

Nikita Bridan, co-founder and CEO of Oilstainlab, joins the show to share how he and his twin brother went from designing concept cars for major OEMs to building their own—the ones the big corporations were too scared to make. They call it building "the bad ideas," and it led them to create the Half-11: a stunningly raw, retro-futuristic supercar with a swappable EV or gas powertrain. This episode is a masterclass in visionary thinking, brand building, and outright industry disruption. For any entrepreneur who has ever been told their idea is too crazy, Nikita’s journey proves that the most "impossible" ideas are often the ones that create the most impact and attract a cult-like following.

💡 What You'll Take Away For YOUR Business

The “Bad Idea” Framework: How to find massive opportunities by building the products and services your competitors are too scared to touch.
Marketing for “Maniacs”: Learn how to attract your perfect customer and build a loyal tribe by unapologetically repelling everyone else.
The Cult Brand Strategy: How to build an inclusive community and a viral following around a high-ticket, exclusive product.
Category-Defining Innovation: Why you shouldn’t think in terms of “either/or.” Learn Nikita’s “and” thinking approach to merge opposite concepts (like analog feel and EV tech) to create something entirely new.
Disrupting Distribution: How to bypass traditional industry gatekeepers (like dealerships) to create a direct, experience-driven connection with your customers.
The Power of a Co-Founder: Why having an “enabler” who challenges your thinking is a startup superpower.

📝 About Nikita Bridan

Nikita Bridan is the co-founder and CEO of Oilstainlab, a boundary-pushing custom vehicle manufacturer based in Los Angeles. With over 15 years of experience as a car design strategist for world-renowned brands like GM, Toyota, and Lyft, Nikita grew frustrated with the corporate resistance to true innovation. He and his twin brother, Ilya, founded Oil Stain Lab as a playground to build the "bad ideas" and create vehicles that stir the soul. Their mission is to disrupt the automotive world with designs that are raw, visceral, and unapologetically extreme.

🎯 Nikita’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

“Just do it. And whatever you do, make sure it's different enough that it matters… Even if you hit the wrong note, hit it hard.”

📢 Memorable Quotes

"We build the bad ideas. Our whole premise is to build the things that no one else will for whatever reason, whether it's financial or regulatory or just, you know, people won't buy it." – Nikita Bridan
"Anytime you're building a business, you're in many ways, you're building a cult. You're asking people to believe in something that may not exist." – Nikita Bridan
"Like someone tells you 'no, that's impossible,' you just— that motivates you even more." – Nikita Bridan

💡 Actionable Takeaways

✅ Identify your "bad idea." What's a contrarian or unconventional approach you can take in your industry that incumbents are ignoring?
✅ Define your "maniac." Who is the super-fan you're building your product for, and how can you tailor your messaging to speak directly to them?
✅ Find your "enabler." Seek out a co-founder, mentor, or advisor who isn’t afraid to challenge your ideas and push you to be better.
✅ Separate your brand from your product. Think about how you can create content, merchandise, or a community that allows everyone to participate in your mission, even if they can't afford your core offering.
✅ Question the standard sales model in your industry. Is there a more direct, experience-driven way to connect with and sell to your customers?

🔗 Links & Resources

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