Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

In this special Collab Week episode of Wantrepreneur to Entrepreneur, 8 founders come together to answer one deceptively powerful question:
Think back to a flop or failure you’ve had in your business. How did it end up feeding something that worked?
This episode covers ad campaigns that flopped, teams scaled too fast, AI projects that got ahead of the technology, a contractor who never delivered, an expo full of the wrong audience, a deal lost on the two-yard line, and a lot more. Together, the answers show that the failure itself rarely matters most. What matters is what you do with it next.
For any wantrepreneur or entrepreneur still stinging from something that didn’t work, or wondering whether you’re “failing too much,” this episode is a reminder that every founder you admire has a story like yours. You’ll hear how each one turned a setback into better data, sharper focus, new skills, and a stronger business.
✨ What You’ll Take Away
In this episode, you’ll learn:
How scaling your team before you understand your operations can almost sink your business
Why setting expectations up front matters most when you’re selling AI
How a failed contractor relationship can push you to build skills you never planned to learn
Why asking the right questions saves you time and money
What “the deal dies in maybes” means for founders still building their sales muscle
Why saying no to the wrong opportunities makes room for the right ones
🎙️ Meet the Collab Week Contributors
Sara Reece — Workmind
Sara Reece is the CEO and Co-Founder of Workmind, where she helps organizations use practical, operations-first automation to remove friction and grow without increasing headcount at the same pace. Over the last seven years, she has designed and implemented automation for nonprofits, small businesses, franchise systems, and Fortune 500 enterprises, drawing on a career that spans journalism, television broadcasting, environmental research, and technology. Sara is the author of The Practical Path to Operational Automation and speaks regularly on practical automation, AI, leadership, and sustainable growth.
Connect with Sara:
Website: https://workmind.cloud/
Jaimz Hodge — Cart Catalyst
Jaimz Hodge is the owner of Cart Catalyst, a Missoula, Montana agency that helps Shopify brands convert more customers by removing the hidden friction in their buying experience. From the first ad click to checkout, Jaimz and his team improve both the website and the Google Ads behind it so ecommerce businesses can scale to the next level.
Connect with Jaimz:
Website: https://www.cartcatalyst.com/
Julie Silvestri — Inside Out Box
Julie Silvestri is the founder and CEO of Inside Out Box, which builds custom software and AI tools, starting with how a company’s data is designed and organized. After studying theoretical math at Harvard, Julie spent more than a decade at startups in finance and edtech, where she managed cross-national software development teams. For more than four years, Inside Out Box has served a broad range of mid-sized companies.
Connect with Julie:
Website: https://www.insideoutbox.com/
Jane Alexander — Emma Advisor
Jane Alexander is the founder and CEO of Emma Advisor, an AI platform that helps families get from high school to college with more clarity, strategy, and confidence. Homeschooled in rural Idaho, Jane went from community college to a private university and later did graduate work at Harvard, then spent more than a decade advising leaders at over 200 colleges and universities. She built Emma Advisor on the belief that opportunity shouldn’t depend on connections or expensive consultants.
Connect with Jane:
Website: https://emmaadvisor.ai/
Felix Vicknair — United Business Works
Felix Vicknair is an executive business advisor and the founder of United Business Works, based in Chattanooga, Tennessee. He provides cost optimization services that help small businesses, nonprofits, and healthcare practices reduce expenses and run leaner, both locally and across the US.
Connect with Felix:
Website: https://unitedbusinessworks.com/
Kacy Webster — Profit Quiver
Kacy Webster is a Business Transformation Strategist, Certified AI Consultant, and the founder of Profit Quiver, based in Minburn, Iowa. With more than 30 years of executive leadership in higher education, workforce development, and enterprise transformation, she helps colleges, nonprofits, and organizations adopt AI in ways their people can trust. Her framework, the 12 Domains of Human-First AI Adoption, gives leaders a structured path to transformation that starts with culture, alignment, and readiness rather than the technology itself.
Connect with Kacy:
Website: https://www.profitquiver.com/
Drew Mehta — ThinkFraction
Drew Mehta is the founder of ThinkFraction, which helps owner-operated businesses build practical AI into their everyday workflows to grow revenue, lower costs, and improve quality. After more than 20 years in corporate, much of it in product management, Drew now combines advisory, implementation, and education to fix the leaks in his clients’ back-end operations, and he’s open about learning the entrepreneurial journey as he goes.
Connect with Drew:
Website: https://thinkfraction.xyz/
Heather Waisanen — Coastal Maverick
Heather Waisanen is the founder of Coastal Maverick, a woman-owned boutique out-of-home advertising agency in Jacksonville, Florida that helps brands nationwide with strategy, media planning, buying, negotiation, and campaign execution. After being laid off from her role as a senior media planner, she launched the agency, drawing on more than a decade of experience across the client, agency, and media owner sides of the industry. Now in her fourth year in business, Heather was named a JAX Chamber Small Business Leader of the Year and is a member of the inaugural 2026 Visionaries 200 class.
Connect with Heather:
Website: https://www.coastalmaverick.com/

Nils Olsen, a former Airborne Infantry Officer, is rewriting the rules of defense technology with his AI-powered startup, Six Tango. In this episode, Nils shares his incredible journey from the front lines to founder, revealing how he took a problem he experienced firsthand in the military and turned it into a groundbreaking business. He unpacks the "Moneyball for the military" strategy, showing how data can uncover hidden opportunities in any industry. This episode is a must-listen for any entrepreneur who wants to build a lean, mission-driven company, leverage AI to do more with less, and find the courage to take the leap into a venture they truly believe in.
💡 What You'll Take Away For YOUR Business
🚀 How to translate skills from a non-business background (like the military) into a powerful founder's toolkit for leadership, planning, and execution.
🤖 Why AI is a game-changer for solo founders and small teams, allowing you to build a functional MVP in days and automate operations from the start.
📊 The "Moneyball" Mindset: How to identify and build the data layer in your industry to uncover overlooked drivers of performance and create a massive competitive advantage.
🎯 How to build a truly user-centric product by getting "in the trenches" with your customers to solve the problems they actually have, not the ones you assume they do.
👨‍👩‍👧 The Founder-Parent Playbook: Actionable strategies for structuring your time to build a high-growth startup while remaining a present and engaged parent.
💡 The crucial difference between "deliberate preparation" and "general preparation," and why you need to invest in both to seize unforeseen opportunities.
💪 Why anchoring your business in a personal mission makes the entrepreneurial journey easier, especially when facing the inevitable risk of failure.
📝 About Nils Olsen
Nils Olsen is the founder and CEO of Six Tango, an innovative company building AI-powered mission planning software for frontline military leaders. Before launching his venture, Nils served for nine years as an Airborne Infantry Officer in the U.S. Army, where he experienced firsthand the technology gaps he is now working to solve. His unique perspective as both the end-user and the founder gives him a powerful advantage in the defense tech space, allowing him to build a product that is not just technologically advanced, but deeply practical and designed for the people who need it most.
🎯 Nils’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
“Identify something that you care about, identify something you're willing to fight for, someone you're willing to fight for, and then spend your time doing that because I think that's going to be time well spent.”
📢 Memorable Quotes
“No plan survives first contact. No, everyone has a plan until they get punched in the face.” – Nils Olsen
“If I fail, I'm failing in pursuit of trying to deliver for people I care about and a product that I completely believe in.” – Nils Olsen
“We're trying to build something that comes out of the box...when they open it, they say, 'this is exactly how I would have designed it myself.'" – Nils Olsen
💡 Actionable Takeaways
✅ Identify a problem you wish was solved for you in a previous career; this is often the most powerful source for a business idea.
✅ Experiment with AI code assistants to build a rapid MVP of your idea, even if you don't have a technical background.
✅ Block out non-negotiable personal or family time on your calendar first, then build your work schedule around those "glass balls."
✅ Establish a "battle rhythm" for your week with dedicated blocks for deep work, calls, and strategic planning to maintain focus and momentum.
✅ Go talk to your potential users. Get "wet and dirty" to understand their real-world pain points before you write a single line of code.
🔗 Links & Resources
Website: https://sixtango.ai
Connect with Nils on LinkedIn
Follow Six Tango on LinkedIn

Overwhelmed by a daily flood of 100+ emails, Curtis Boortz decided to solve his own problem by building a custom AI tool. That tool evolved into ForthWrite, an AI platform that drafts emails in your authentic voice, directly within your inbox. In this episode, Curtis shares his incredible journey from finance professional to solo tech founder, revealing how he transformed a personal pain point into a scalable SaaS business. This episode is a masterclass for any entrepreneur looking to leverage AI not just as a chatbot, but as a deeply integrated tool to save time, enhance client communication, and free yourself up to do the work that truly matters.
💡 What You'll Take Away For YOUR Business
🚀 How to turn a personal business frustration into a sellable software product.
🤖 The step-by-step process for training AI to write in your unique voice, moving beyond generic, cookie-cutter responses.
workflow integration, and why the best AI tools are the ones you don't have to think about using.
💡 How to strategically target a niche industry (like finance or accounting) by building solutions for their biggest compliance and efficiency challenges.
🤝 Why AI is the ultimate co-founder for solopreneurs, helping with everything from business strategy to product development.
🧠 The critical difference between simply using AI (like ChatGPT) and truly implementing AI workflows to automate and scale your operations.
💰 How to augment your team with AI to free up human capital for high-value tasks, rather than replacing them.
📝 About Curtis Boortz
Curtis Boortz is the founder of ForthWrite, an AI email tool, and an AI implementation consultant. With a background in SMB lending, Curtis experienced firsthand how client emails could consume the entire workday. Instead of accepting the status quo, he taught himself how to build an AI solution that drafted emails in his own voice, which became the foundation for Fourthrite. Today, he helps professionals and firms integrate AI into their core operations, proving that the future of business isn't about replacing humans, but augmenting them with intelligent, personalized technology.
🎯 Curtis’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"AI looks complicated on the surface, but it's really not as complicated as you think if you start to just spend time with the tools. Get in there, start using it, get your hands dirty, and see what you can do."
📢 Memorable Quotes
“AI automation, I don't believe should replace employees. I think it should augment them, free them up to do more important tasks.” – Curtis Boortz
“I didn't want to do the tab switching that eats more time than you think, that distracts your focus more than you think. ForthWrite lives directly in the inbox.” – Curtis Boortz
“If it wasn't for AI, I probably wouldn't be here today. AI has made the entire journey from the start to where I am now possible.” – Curtis Boortz
💡 Actionable Takeaways
✅ Audit your inbox. Identify the top 3-5 types of emails you write repeatedly and use them as a starting point to create a "voice profile" for an AI tool.
✅ Instead of just copying and pasting into ChatGPT, explore an AI tool that integrates directly into your existing software (email, CRM, project management).
✅ Challenge an AI with a business idea. Go to a tool like Claude and ask it for critical feedback on a strategy, encouraging it to be less agreeable and more analytical.
✅ Dedicate 30 minutes this week to "get your hands dirty." Pick one manual, repetitive task in your business and research how an AI tool could automate it.
🔗 Links & Resources
Website: https://www.forthwrite.ai
Connect with Curtis on LinkedIn
Follow ForthWrite on LinkedIn
Follow Curtis on Instagram

Are you tired of feeling like your team is constantly distracted, solving the same problems over and over? In this powerful episode, former C-suite executive Rachel Honoway reveals how to break the cycle of "creative avoidance" and rewire your organization for true alignment and explosive growth. She shares why most leadership teams aren't nearly as aligned as they think and provides a simple exercise to expose the gaps immediately. For any wantrepreneur or entrepreneur who wants their team to move faster, make better decisions, and execute without constant hand-holding, this conversation is a masterclass in getting to the root of what truly matters. Rachel’s experience as a CEO, CMO, and certified ‘Why’ coach provides a unique framework for building a business that wins on purpose, not just price or speed.
💡 What You'll Take Away For YOUR Business
How to Stop Chasing Symptoms & Solve the Real Problem: Learn to identify and address the root cause of recurring issues (like employee attendance) instead of getting distracted by surface-level fixes.
The Ultimate 2-Minute Alignment Test: Discover a simple exercise to instantly gauge if your leadership team is actually on the same page about company goals—or just thinks they are.
Using Marketing Psychology for Internal Leadership: Understand how to apply the principles of a sales funnel to communicate with your team, manage up, and get buy-in for your most important initiatives.
Why Authenticity is Your Greatest Competitive Advantage in the AI Era: Rachel explains why speed and low cost are becoming commodities and how building a brand on authentic trust is the only sustainable way to win.
Unlock Your ‘Why’ Beyond the Buzzword: Move past the surface-level "purpose" to uncover the deep-seated drivers for you and your team, creating unshakeable motivation and clarity.
The Power of Proactive Internal Communication: Learn why you need to communicate with your team consistently—not just during big wins or major crises—to build a unified, mission-driven culture.
📝 About Rachel Honoway
Rachel Honoway is a "recovering corporate executive" who spent 25 years in the business world, with over half of that time in the C-suite as a CEO, CMO, and CPO. Having lived the constant tug-of-war between supporting her team and driving business growth, she now helps leaders rewire how their organizations make decisions. Through her advisory firm, Delta Catalyst Lab, she works with executives to align on purpose, set clear priorities, and empower their teams to stop escalating problems and start executing on what matters most.
🎯 Rachel’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"You have to know who you are and what you want... If I said to anybody right now, 'What do you really want?' they struggle with the answer to that question. So I would say that you need to figure out the answer to that question... and then figure out how you're going to get it."
📢 Memorable Quotes
“People get so distracted by the downstream impacts, by the symptoms, that you miss what's really happening. Why are we here? What are we really trying to do here? And if you can stop and solve for that, then everything else just falls into place.” – Rachel Honoway
“With AI, all of those things are commodities. Everybody can go fast. Everybody can produce more... You're not going to win on those things anymore. What you're going to win on is why your customers are going to buy from the people they want to buy from... and the companies that they trust.” – Rachel Honoway
“Discovering your actual why and getting the words for it... is one of those things that when you see it, you can't unsee it. So all of a sudden, that clarity comes and everything else starts to just get a little bit more in focus.” – Rachel Honoway
💡 Actionable Takeaways
Run the Alignment Test: This week, gather your leadership team (even if it's just you and a co-founder) and have everyone silently write down the top 3 company goals for the quarter. Compare notes and see where the gaps are.
Start an Internal Communication Rhythm: Don't wait for a crisis or a huge announcement. Set up a simple weekly email, Slack update, or short video to share what’s on your mind as a leader and reinforce the company’s purpose.
Question Your "Urgent" Problems: The next time a painful, recurring issue lands on your desk, stop and ask: "What is the real reason this keeps happening?" Focus on the root cause, not the immediate symptom.
Ask Yourself "The Question": Set aside 30 minutes of uninterrupted time to answer Rachel’s prompt: "What do I really want?" Write it down and be brutally honest with yourself.
🔗 Links & Resources
Website: http://www.deltacatalystlab.com
Connect with Rachel on LinkedIn
Follow Delta Catalyst Lab on LinkedIn

Feeling stuck, burned out, or hitting the same revenue wall year after year? This episode is your permission slip to stop searching for the next "perfect" strategy. We sit down with Shervon Laurice, a licensed psychotherapist and transformational coach who reveals why your biggest business breakthroughs have nothing to do with your marketing plan or sales funnel. She explains that real, sustainable growth comes from developing your inner world—regulating your nervous system, consciously shaping your identity, and building the capacity to hold the discomfort that comes with expansion. For wantrepreneurs and entrepreneurs tired of the hustle, this conversation is a masterclass in building a business that feels aligned, expansive, and truly successful from the inside out.
💡 What You'll Take Away For YOUR Business
The Entrepreneurial Mindset Shift: Discover the critical difference between being an employee in your own business versus being a true entrepreneur who works on the business.
Break Through Your Plateaus: Learn why simply changing your strategy isn't enough when you're stuck, and how to use Shervon's "pause and regulate" method to diagnose the real root of the problem.
Beyond Awareness: Understand why awareness alone isn’t enough for change and how to move from intellectual understanding to embodied action that actually drives results.
Nervous System as a Business Tool: Learn how to regulate your nervous system to build capacity for more success, handle risk, and make decisions from a place of clarity instead of fear.
Identity as Your Foundation: Uncover how your current identity—shaped by family, community, and past experiences—might be holding your business back and how to consciously build a new one.
Become Irreplaceable in the Age of AI: Get a powerful framework for shifting your perspective on disruptive technologies, focusing on where your human expertise provides irreplaceable value.
📝 About Shervon Laurice
Shervon Laurice is a licensed psychotherapist, transformational coach, and psycho-spiritual guide with over 23 years of experience helping people create profound change. She is the founder of Restore Tranquility, a psychotherapy practice, hosts The Expansion Room podcast, and created ELEVATE, her 90-day coaching experience for soul-led entrepreneurs. Shervon’s unique power lies in her ability to merge deep therapeutic knowledge with practical coaching, guiding leaders to understand that real change lives in the body, not just the mind. She helps founders stop working against themselves and start building from a place of true alignment and inner power.
🎯 Shervon’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Develop your inner world... Entrepreneurship is a spiritual practice."
📢 Memorable Quotes
“You can be an employee in your own business because you still have employee mindset, or you can be an entrepreneur who works on your business and looks at expansion always as your option.” – Shervon Laurice
“Entrepreneurship is not for the faint of heart. And so you've really got to build a foundation so that you can move forward consciously.” – Shervon Laurice
“Most of us are moving through our businesses dysregulated and we don't even know it.” – Shervon Laurice
💡 Actionable Takeaways
Conduct an Identity Audit: Ask yourself, "Who am I being in my business right now?" and "Is this the identity of the person who can achieve my biggest goals?" If not, start defining who you need to become.
Practice the Pause: The next time you feel stuck or hit a wall, resist the urge to immediately find a new strategy. Instead, take time to sit with the discomfort and ask what it's trying to teach you about your inner state.
Identify Your Nervous System Triggers: Pay attention to what situations in your business cause you to feel fear, anxiety, or shutdown. Awareness is the first step to learning how to regulate through them.
Reframe Your Value: In the face of changes like AI, shift your focus from what you do to how you think. Your judgment, historical context, and ability to be the "bridge" are skills that cannot be automated.
🔗 Links & Resources
Website: https://restoretranquility.org
Personal website: https://shervonlaurice.com/assessment
Connect with Shervon on LinkedIn
Follow Restore Tranquility, LLC on LinkedIn
Check out The Expansion Room Podcast