Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

In this game-changing episode, Leila Kaneda, a former professional musician turned AI expert, reveals how to harness artificial intelligence with purpose and intention. She shares her incredible journey from music to machine learning and explains why your unique, non-linear background is your greatest asset in business. This episode is a masterclass for any entrepreneur feeling overwhelmed by the AI hype. You'll learn how to move beyond generic tools like ChatGPT, avoid common pitfalls that damage your brand, and implement AI in a way that saves you time and cognitive energy without losing the human touch. Leila's "teach you to fish" philosophy is designed to empower you to build and maintain your own AI-driven solutions, making this a must-listen for founders who want to innovate sustainably.

💡 What You'll Take Away For YOUR Business

• 🚀 How to leverage your non-linear career path as a unique superpower in your business.
• 🧠 The critical mindset shift required to move from AI user to AI innovator and open the "floodgates" of ideas.
• 🤖 A step-by-step breakdown of how to intentionally integrate AI into your social media workflow to save time without sacrificing brand authenticity.
• 💰 Why the most effective AI strategy isn't about replacing humans, but about augmenting their skills to achieve 100x results.
• 🛠️ How to identify the right places to insert AI into your business for maximum ROI and where to avoid it.
• 🤝 Why you should seek consultants who empower you to be independent, not lock you into expensive long-term retainers.
• 🎉 The power of "playing" with AI on personal projects to rewire your brain and spark game-changing business ideas.

📝 About Leila Kaneda

Leila Kaneda is the founder of Kaneda Consulting, an AI education and strategic consulting firm. With a Master's in AI and Machine Learning and a background as a professional musician, Leila brings a uniquely creative and human-centered approach to the world of technology. She specializes in cutting through the hype and fear around AI, teaching entrepreneurs how to leverage this powerful technology in ways that align with their values. Her mission is to empower business owners with the knowledge to implement and maintain their own AI solutions, fostering true independence and innovation.

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

"Always figure out what you want to do and why, and make sure that whatever that is, is something that you are excited about and really care about. And then once you have that identified, do everything in your power to make that happen."

📢 Memorable Quotes

• "AI at its core is really a tool... behind all of these things, no matter what it looks like, it's just an algorithm. And the more that we can remember that, the more we can take that step back and say, okay, intentionally, what am I trying to do with my business?" – Leila Kaneda
• "When you're in the field of AI... it's a mindset shift more than anything... And so once you learn enough to shift your mind, it's like the floodgates open." – Leila Kaneda
• "If what you're trying to do is as important to you as you think it is, it'll be equally as important and infectious to the rest of the world. That's what we can do to make a difference." – Leila Kaneda

💡 Actionable Takeaways

• ✅ Audit Your Workflow Intentionally: Pick one repetitive task in your business (like social media content creation) and map out your current process. Identify where AI can assist with research or drafting, not replace your final, human touch.
• ✅ Schedule "AI Playtime": Dedicate one hour this week to using an AI tool for a fun, non-business project. Build a trivia game, plan a dream vacation, or write a song. The goal is to learn the tool's capabilities in a low-pressure environment.
• ✅ Define Your Core Mission: Before you invest in any new technology, write down the core mission of your business and what excites you most about it. Ensure any tool you adopt serves that mission directly.
• ✅ Empower, Don't Depend: When hiring a consultant or expert, ask them how they plan to transfer their knowledge to you and your team. Prioritize partners who aim to make themselves obsolete.

🔗 Links & Resources

• Website: https://www.kaneda-consulting.com
• Connect with Leila on LinkedIn
• Follow Kaneda Consulting on LinkedIn
• Follow Kaneda Consulting on Instagram
• Follow Kaneda Consulting on TikTok
• Follow Kaneda Consulting on Facebook
• Follow Kaneda Consulting on YouTube

In a world saturated with forgettable digital ads, how do you create a brand experience that people talk about for weeks? Alejandro Guzman of Azul Marketing reveals how he combines behavioral economics, world-class creativity, and the power of gamification to craft truly memorable moments for brands like Coca-Cola. This episode is a masterclass in thinking differently, showing how your unique curiosities—from video games to psychology—can become your greatest business assets. Tune in to learn how to surprise and delight your audience, leverage AI as a creative superpower, and design marketing that makes a lasting impact.

💡 What You'll Take Away For YOUR Business

• The Gamification Goldmine: Learn how to apply game mechanics to real-world business scenarios (like turning a corporate convention into a viral trading card game) to drive unprecedented engagement and connection.
• AI as Your Creative Exoskeleton: Discover why AI isn't a threat but an incredible tool that augments your abilities, allowing you to prototype, brainstorm, and execute ambitious ideas faster than ever before.
• The Power of Being a Generalist: Understand why exploring diverse interests (like Roger Federer did with multiple sports) can give you a broader toolkit and a more innovative approach to problem-solving than hyper-focused specialists.
• Reverse-Engineer Your Marketing: Learn how to start with the end-user's psychology and work backward to craft messages and experiences that resonate deeply and drive action.
• Escaping "Hedonic Adaptation": Get strategies to combat the natural tendency for audiences to get bored, and learn how to consistently create surprising, memorable moments that stand out.
• Marketing Beyond the Screen: Hear a powerful case for why experiential, in-person marketing creates a stickiness and a human connection that digital ads simply can't replicate.

📝 About Alejandro Guzman

Alejandro Guzman is a creative force with over 18 years of experience working with world-class brands and agencies. As the founder of Azul Marketing, he specializes in creative direction, graphic design, and crafting unique engagement tools. With a Master's in Sustainable Design and a deep curiosity for human behavior and gamification, Alejandro brings a refreshingly different perspective to marketing, transforming standard corporate events and campaigns into unforgettable, immersive experiences.

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

"Go work through your ideas, be creative, soak yourself with multiple things... the more concepts you have to you, the more creative you can be."

📢 Memorable Quotes

• "AI is just an augmentator of our capacities. So if you're a creative person, AI is just like having an exoskeleton in the space. You have superpowers." – Alejandro Guzman
• "You can spend the dollar and having nobody remember what you did the next minute or spend the same dollar and having somebody talking about it to their friends in a week... the second dollar is very well spent." – Alejandro Guzman
• "I cannot be creative in a world that I don't know. So the same thing applies for everything. You need to go and test and taste all the foods, taste all the flavors so you can be the best chef ever." – Alejandro Guzman

💡 Actionable Takeaways

• Brainstorm a "Gamification" Element for Your Business: Identify one customer touchpoint (e.g., onboarding, a live event, a loyalty program) and think of one way you could introduce a game-like mechanic to make it more engaging.
• Use AI for a "What If" Scenario: Spend 30 minutes with an AI tool like ChatGPT or Midjourney to prototype a wild idea you've had. Ask it to generate concepts, visuals, or copy to see how it can accelerate your creative process.
• Schedule "Curiosity Time": Block 1-2 hours on your calendar this week to learn about a topic completely unrelated to your work. Watch a documentary, read a book, or listen to a podcast from a different field.
• Map Your Customer Experience: Think about a recent brand interaction you had that was truly memorable. What made it special? Now, analyze your own customer journey and identify one opportunity to surprise and delight them.

🔗 Links & Resources

• Website: https://www.azulmarketing.co
• Connect with Alejandro on LinkedIn
• Follow Azul Marketing NA on LinkedIn

As November kicks off and we enter the month of giving thanks, who’s the one person you’ve been forgetting to thank? Your entrepreneurial journey will be filled with people: friends and family, clients, partners, and even a few internet trolls. But only one person will be there for every up, every down, every moment of self-doubt, and every crazy idea. In this Solo Sunday episode, Brian turns a viral social media post into a powerful reminder that you are that person. Drawing on his conversations with thousands of entrepreneurs, he shares why the happiest and most successful founders are always on their own side, and why your high standards can coexist with being gentle, gracious, and kind to yourself.

✨ Why This Matters for You

Being your own biggest champion is a game-changer for entrepreneurs because:

• You’re the only person who will experience every moment of your journey.
• Not everyone will celebrate your wins, so you need to know how to celebrate them yourself.
• Your highest standards don’t have to come at the expense of your self-belief.
• Self-kindness gives you a steadier foundation for handling losses, setbacks, and self-doubt.
• Happiness is the most important metric of all, and it starts with being on your own side.

📝 Key Takeaways

• You’re the Only Constant. Parents, kids, partners, and friends can’t be there for your entire life. You’re the only person who’s there for all of it.
• Be the Person You Want in Your Corner. Give yourself what you’d want from someone else: celebration during the highs and encouragement during the lows.
• High Standards and Self-Kindness Must Coexist. You can hold yourself accountable and still be your biggest cheerleader. Be gracious with yourself as you pursue your goals.
• Your Wins Reveal Who’s Really with You. It’s easy for people to show up during your lows, but your highs can put their own lives under the microscope. Don’t rely on everyone else to celebrate your success.
• Self-Belief Takes Practice. Being your own champion doesn’t happen by mistake. You build that belief through how you respond to each win and each loss.

🚀 Put It Into Action

This week, practice being on your own side:

• Carve out some time to reconnect with why you believe in yourself and why you started this journey.
• Pick one recent win and allow yourself to truly celebrate it.
• Think back on a recent loss and tell yourself what you’d want to hear from someone in your corner: “We are doing our best, we are learning, and we are moving forward.”
• Make a list of the things you’re thankful to yourself for, including the effort and energy you’ve put into your entrepreneurial journey.

🔗 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 a reminder to be kinder to themselves

In this special Collab Week episode of Wantrepreneur to Entrepreneur, 10 founders come together to answer one deeply personal question:

Tell us about a decision or mistake that haunted you, and how you finally put that ghost to rest.

The ghosts in this episode include a strategy deck that walked out the door, funding turned down at the finish line, a six-figure funnel kept running out of attachment, and friendships that made hard calls even harder. It’s a wide-ranging, refreshingly honest episode, and it’s a reminder that the mistake itself rarely haunts us for long. What haunts us is a lesson we haven’t put into practice yet.

For any wantrepreneur or entrepreneur still replaying a decision they wish they could take back, this episode is proof that you’re not alone. Every founder carries a few ghosts, and the ones who grow are the ones who turn those ghosts into guardrails, boundaries, and better instincts.

✨ What You’ll Take Away

In this episode, you’ll take away:

• How the “first big check” can cost you far more than it pays
• Why how you treat the people building your business deserves as much attention as any strategy decision
• How to walk away from a growth path that’s out of alignment, even with funding on the table
• Why years of industry expertise don’t automatically make you good at pricing your own work
• How to stay generous without letting people build on you instead of with you
• Why turning off the marketing isn’t the same as killing your first business
• Why every founder’s ghost can become the foundation for how they lead next

🎙️ Meet the Collab Week Contributors

Renée Holder — Janus Management Group

Renée Holder is the Founder, President, and Principal Consultant of Janus Management Group, a New York-based firm specializing in organizational change management strategy, training, and transformation support. A certified change management professional with more than 20 years of experience, Renée helps organizations and their people navigate technology, HR, and ERP transformations, including large-scale systems like SAP, with confidence and success.

Connect with Renée:

https://www.janusmanagementgroup.com/

William McCumber — Rowan Elder Productions & Applied Erudition

William McCumber is the founder of two ed-tech companies, Rowan Elder Productions and Applied Erudition. Rowan Elder is an async faculty development program that upskills professors to build studio-quality online lectures that feel more like YouTube than a lecturer reading slides at the front of the room. Applied Erudition is a platform that measures real capability rather than seat time.

Connect with William:

https://www.rowanelder.com/

https://appliederudition.com/

Sara Reece — Workmind

Sara Reece is the CEO and Co-Founder of Workmind, where she helps organizations use practical, operations-first automation to eliminate friction and grow without increasing headcount at the same pace. For the last seven years, she has designed and implemented automation with organizations ranging from nonprofits and small businesses to franchise systems and Fortune 500 enterprises. Her unconventional career spans journalism, television broadcasting, environmental research, and technology, and she is the author of The Practical Path to Operational Automation.

Connect with Sara:

https://workmind.cloud/

https://www.saralreece.com/

Drew Mehta — ThinkFraction

After more than 20 years in corporate, Drew Mehta founded ThinkFraction to help owner-operated businesses integrate AI into their everyday workflows and processes in a practical, hype-free way. He helps owner-operators grow revenue, lower costs, and improve quality by fixing leaks in their back-end workflows. ThinkFraction pairs advisory with hands-on implementation and education, and Drew teaches clients how AI fits into their business while learning the entrepreneurial ropes himself.

Connect with Drew:

https://thinkfraction.xyz/

Janice Kephart — ZipID

Janice Kephart is a lawyer, identity expert, and the founder of ZipID. She drafted the federal identity theft criminal statute for the U.S. Senate Judiciary Committee, served on the 9/11 Commission, helped architect both REAL ID and the nation’s biometric border entry-exit system, and later developed biometric workflows at MorphoTrak (now Idemia). ZipID brings real biometric identity verification to the Form I-9 process so employers can meet federal requirements with confidence, and Janice is now building ZipID’s ID Fraud Forensic Dashboard for banks, credit unions, casinos, and any business that needs to know an ID is legitimate.

Connect with Janice:

https://www.zipidapp.com/

Anne Gillaspie — Fix & Form

Anne Gillaspie is a global keynote speaker, truth disruptor, and creator of SHARE YOUR FEAR™, a movement that makes fear less scary and truth easier to tell. A 12-year entrepreneur, she is the CEO and founder of Denver-based Fix & Form Branding Firm, host of the top-ranked OnlyFounders podcast, and a brand therapist to founders and executives. Through storytelling, unexpected dance, and radically human experiences, Anne challenges audiences to stop performing and start telling the truth about who they are.

Connect with Anne:

https://theannegillaspie.com/

https://fixandform.com/

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 advertising strategy, media planning and buying, negotiation, and campaign execution. With more than a decade of experience across the client, agency, and media owner sides of the industry, she launched Coastal Maverick after being laid off from her role as a senior media planner. Now in her fourth year of entrepreneurship, Heather was recognized as a JAX Chamber Small Business Leader of the Year and is a member of the inaugural 2026 Visionaries 200 class.

Connect with Heather:

https://www.coastalmaverick.com/

Kacy Webster — Profit Quiver

Kacy Webster is a Business Transformation Strategist and Certified AI Consultant with 30+ years of executive leadership across higher education, workforce development, and enterprise transformation. Through Profit Quiver and The PrecisionX System, she partners with mid-market manufacturers, B2B leadership teams, colleges, and workforce organizations to adopt AI in a way their people can actually 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 before technology.

Connect with Kacy:

https://www.profitquiver.com/

Erik Berglund — The Language of Leadership & Loominary

Erik Berglund is the founder of The Language of Leadership and Loominary, and host of the I Have Some Questions podcast. His companies help people practice difficult conversations before they have to have them in real life. The Language of Leadership offers a framework for leadership communication, and Loominary builds custom skill simulation systems that give businesses a way to reinforce those skills across their teams.

Connect with Erik:

https://www.languageofleadership.io/

https://www.loominary.io

Jane Alexander — Emma Advisor

Jane Alexander is the founder and CEO of Emma Advisor, an AI platform that helps students and families navigate the path from high school to college with more clarity, strategy, and confidence. Her own path was unconventional: she was homeschooled in rural Idaho, started at community college, transferred to a private university, completed graduate work at Harvard, and spent more than a decade advising leaders at over 200 colleges and universities. She built Emma Advisor so that opportunity doesn’t depend on social capital, connections, or the ability to hire expensive consultants.

Connect with Jane:

https://emmaadvisor.ai/

In a world grappling with the rise of AI, how do we protect the invaluable human skills of critical thinking, creativity, and authenticity? Jordan Wolff, a former educator turned founder, is tackling this challenge head-on. In this episode, Jordan shares his journey from the classroom to launching Typed by Hand, an EdTech company designed to champion authentic student work, not police it. This isn't just a conversation about education; it's a masterclass in building a purpose-driven, bootstrapped, and globally-distributed company. For any entrepreneur passionate about solving real-world problems, Jordan’s story provides a powerful blueprint for turning deep industry expertise into a thriving business that values humanity over automation.

💡 What You'll Take Away For YOUR Business

• 🌍 How to successfully build and manage a global team by leaning into trust, delegation, and a shared mission.
• 👨‍🏫 Why the skills honed as a teacher—managing chaos, wearing multiple hats, and staying calm under pressure—are a secret weapon for entrepreneurs.
• 🤝 How to build customer relationships based on partnership and trust, rather than an adversarial "policing" model.
• 💪 The strategic advantages of bootstrapping your startup to maintain your mission and avoid the pressures of VC funding that can dilute your vision.
• ❤️ Why embedding "pride" and "humanity" into your product can be a powerful differentiator in an increasingly automated world.
• 🎯 How to leverage your deep industry experience to identify and solve a critical problem that others overlook.

📝 About Jordan Wolff

Jordan Wolff is the CEO and founder of Typed by Hand, an education technology company focused on protecting authentic student writing in the age of AI. Before launching his company, Jordan spent over a decade as an ELA teacher, school leader, and consultant across the United States and internationally. His hands-on experience in the classroom shaped his powerful belief that the future of integrity isn't about policing students, but about empowering them to take pride in their own work. Jordan brings a unique and essential perspective, blending the heart of an educator with the strategic mind of a global entrepreneur.

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

"Keep calm and cool." In entrepreneurship, you are constantly putting out fires. A teacher’s ability to calmly manage a chaotic classroom—whether it's kids fighting or a mouse in the corner—is the same skill set needed to navigate the daily challenges of a startup.

📢 Memorable Quotes

• “It's not always the outcome. It's also the process, the beautifully ugly process that we have to value and, you know, what it means to be human.” – Jordan Wolff
• “Teachers, I mean, these are intelligent human beings that studied how to teach other human beings. They know when someone is a fake.” – Jordan Wolff
• “I think we all need to take a second to breathe. We need to embrace moments of reflection and relaxing and, you know, appreciate ourselves.” – Jordan Wolff

💡 Actionable Takeaways

• ✅ Identify a problem in your own industry that you understand better than anyone else. Your insider knowledge is your greatest competitive advantage.
• ✅ When building a remote team, make your company’s mission the central pillar of your culture to keep everyone aligned and motivated across time zones.
• ✅ Instead of trying to "catch" customers or users doing something wrong, build systems that encourage and reward authenticity and trust.
• ✅ Before seeking outside funding, explore bootstrapping to prove your concept and retain full control over your company's direction and values.
• ✅ Acknowledge your ability to handle pressure. The next time you face a "fire" in your business, channel the calm composure of a seasoned teacher.

🔗 Links & Resources

• Website: https://www.typedbyhand.com
• Try Typed by Me for free
• Connect with Jordan on LinkedIn
• Follow Typed by Hand on LinkedIn
• Follow Typed by Hand on Facebook
• Follow Typed by Hand on Instagram

Rayne Chapman, a creative director turned tech founder, joins the show to share how she transformed a personal frustration—the lack of a good way to save online inspiration—into a thriving business called Neat. This episode is a masterclass in building a product with deep intentionality, driven by genuine user needs rather than just adding features for the sake of it. For any entrepreneur or wantrepreneur, this conversation is packed with insights on how to leverage your unique background, use customer feedback to build a better product, and embrace the often-scary but magical process of building a company from the ground up.

💡 What You'll Take Away For YOUR Business

• 🚀 How to turn your own professional frustration into a scalable business idea.
• 🗣️ Simple, effective strategies for gathering user feedback that actually shapes your product roadmap (hint: it's not just NPS scores).
• 🤖 Why AI is a powerful augmentation tool for creativity and productivity, not a replacement for human vision.
• 🧠 The power of cross-industry inspiration (like a bullet train inspired by a bird) to solve complex business problems.
• 🎨 How to build a brand that empowers your users' unique vision instead of imposing your own aesthetic.
• 🧘‍♀️ Why embracing the "process" over instant gratification is the key to building a sustainable and impactful business.

📝 About Rayne Chapman

Rayne Chapman is the Founder and CEO of Neat, an innovative platform for saving and organizing creative inspiration. With a rich background as an agency art director and creative director at places like Meta, she experienced firsthand the problem of wrangling inspiration from endless online sources. Rayne brings a unique, creative-first perspective to the world of tech entrepreneurship, focusing on building tools that are intentional, user-centric, and designed to enhance human creativity.

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

Don't underestimate the power of the process; the magic is in the day-to-day journey of building, not just in reaching the destination.

📢 Memorable Quotes

• “Building something that actually helps people and is really intentional, I think, is kind of that human superpower we want to hold on to.” – Rayne Chapman
• “I actually think the magic is in the process... the inspiration is where you start, but like the happy accident or the things or the challenges along the way are what that's going to make that end product feel really unique and ownable to you.” – Rayne Chapman
• “You can find inspiration that's completely unrelated to something that you're doing and it can help you solve a problem.” – Rayne Chapman

💡 Actionable Takeaways

• ✅ Start your own inspiration board today. Use a tool like Neat to save ideas from different sources—websites, images, links—and see what new connections you can make.
• ✅ Actively seek user feedback. Instead of a generic survey, send a personal email or text to a few key users and ask, "What's one thing that would make this more useful for you?"
• ✅ Look for inspiration outside your industry. Spend 30 minutes this week exploring a topic completely unrelated to your business (like nature, architecture, or sports) and see what ideas it sparks.
• ✅ Experiment with an AI tool to augment a task you dislike. Use something like Gamma AI for presentations or another tool to help with note-taking, and see how it can free up your time for more creative work.

🔗 Links & Resources

• Website: https://neatinspo.com
• Connect with Rayne on LinkedIn
• Follow Neat Inspo on LinkedIn

In a world buzzing with AI advancements, Masumi Nakamura is focused on the one thing technology often overlooks: the people. After 25 years as a top engineering leader at giants like Cisco and PayPal, Masumi realized the biggest challenges weren't in the code, but in the complex human dynamics of a team. In this episode, he introduces askMyu, his private AI assistant designed to navigate the "people side" of work. This isn't about replacing jobs; it's about enhancing our most human skills. For any wantrepreneur or entrepreneur building a team, this episode is a masterclass in leveraging AI to foster better communication, navigate career growth, and solve the interpersonal issues that truly define a company's success, all while prioritizing individual privacy.

💡 What You'll Take Away For YOUR Business

• Why the most critical business challenges are often human-related, not technical, and how AI can help bridge the gap.
• How to build a company culture where technology enhances human skills like decision-making and relationship-building, rather than replacing them.
• The crucial role of privacy and end-to-end encryption when integrating AI tools into your team's workflow to build trust.
• How an AI assistant can gather context from emails, calendars, and messages to help you prepare for meetings and understand team dynamics.
• A forward-thinking perspective on how AI will increase the importance of human interaction and systemic thinking in the workplace.
• Actionable insights on how to guide your team through the AI revolution by focusing on addition and augmentation, not fear and subtraction.

📝 About Masumi Nakamura

Masumi Nakamura is the co-founder and CEO of askMyu, a private AI assistant for the people side of work. With a storied 25-year career as an engineer and engineering leader, Masumi has been at the forefront of innovation at companies like Cisco, PayPal, and Mercari US, where he served as VP of Engineering. He discovered that across every team, the engineering was the easy part; the human element was the real challenge. This insight, combined with his experience mentoring founders at Techstars, led him to build a tool that helps professionals navigate their careers and relationships at work.

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

"No matter what, it's about the people. If you fundamentally think about what a company is, at the end of the day, it's a grouping of people and resources to get some goal done... The more you understand your relationships, the more you build on it, the better you will be."

📢 Memorable Quotes

• “The engineering, the building, that's the easy stuff. It was the people side that often is the issue.” – Masumi Nakamura
• “You end up having to pay a lot more attention to what's not said as well as what is said.” – Masumi Nakamura
• “The bigger troubling thing that's actually happening is the amount of load is increasing on the person... what humans need to do elevates up. You need to have a better sense of system thinking. You're going to have to interact with more people, actually.” – Masumi Nakamura

💡 Actionable Takeaways

• ✅ Audit your own "people problems." Identify where communication breakdowns or relationship friction are holding your business back.
• ✅ When evaluating AI tools, make privacy your top priority. Ensure any new technology protects individual data and builds trust within your team.
• ✅ Shift your focus from automating tasks to augmenting human capabilities. Use AI to free up time for strategic thinking, creativity, and relationship-building.
• ✅ Encourage your team to develop elevated skills like systems thinking, complex decision-making, and interpersonal communication—these are the skills that will be amplified, not replaced, by AI.

🔗 Links & Resources

• Website: https://www.askmyu.com
• Connect with Masumi on LinkedIn
• Follow askMyu on LinkedIn

Mark McSweeney, a 30-year veteran of the association and nonprofit world, shares powerful insights on governance, strategy, and leadership that apply to any business. He reveals the universal patterns of success he's observed across countless organizations and breaks down why even the most unique businesses face similar challenges. This episode is a masterclass in strategic thinking, teaching you how to get out of the "weeds," facilitate better conversations, and ask the kind of questions that lead to breakthrough solutions. Tune in to learn how to shift from a tactical operator to a visionary leader in your own venture.

💡 What You'll Take Away For YOUR Business

• 🚀 Why "nonprofit is a tax status, not a business strategy" and how to apply this mindset to your own company's growth.
• 🧠 The critical difference between governance and management, and how to adopt a "nose in, fingers out" approach to leadership.
• ❓ A powerful framework for asking "one level higher" to ensure you're solving the right problems, not just the most immediate ones.
• 🤝 The art of facilitation and how to lead your team, clients, and partners to better solutions by asking questions instead of giving answers.
• 📈 How to intentionally carve out time for strategic thinking and escape the "weedy" operational mindset that holds so many entrepreneurs back.
• 💡 The surprising power of associations and why joining one could be the secret to your professional and business growth.
• 🎯 How the E-Myth principle of "technician vs. owner" applies to every stage of the entrepreneurial journey.

📝 About Mark McSweeney

Mark McSweeney is a governance strategist, facilitator, and the founder of Envisioned Future. With over 30 years of experience in the association and nonprofit sectors, including serving as an association CEO at just 27, he brings a unique perspective on leadership. Mark specializes in helping boards and leadership teams think strategically, navigate change, and make better decisions about their future. His genius lies in asking the questions that help leaders get out of their own way and see their challenges from a higher, more impactful vantage point.

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

Before you rush into finding a better answer, make sure you're asking a better question. His advice is to "always ask one level higher" to shift your perspective from immediate problem-solving to true strategic thinking.

📢 Memorable Quotes

• “Nonprofit is a tax status, not a business strategy.” – Mark McSweeney
• “Sometimes the very things that made us successful can also get in the way of where we need to go next.” – Mark McSweeney
• “Before you rush into a better answer, make sure you're asking a better question.” – Mark McSweeney

💡 Actionable Takeaways

• ✅ Schedule dedicated "strategic thinking" time each week. Get out of your usual environment to force your brain out of its operational rut.
• ✅ The next time your team faces a problem, stop them and ask, "What's the bigger question behind the question we're trying to answer?"
• ✅ Practice a "nose in, fingers out" leadership style. Understand what's happening in your business without micromanaging the day-to-day operations.
• ✅ Research and identify a professional association in your industry. Explore joining to tap into a community of peers for networking and growth.
• ✅ Re-evaluate your business model with the mindset that you are a business first, regardless of your mission or tax status.

🔗 Links & Resources

• Website: https://envisionedfuture.co
• Connect with Mark on LinkedIn
• Follow Envisioned Future LLC on LinkedIn

Every entrepreneur loves the superhero story: the founder who swoops in at midnight to fix the crashed server, write the perfect sales copy, and hold the whole business together. But what if that superhero is actually trapped in a cage built from their own competence? In this special Solo Sunday, Brian is unplugged and spending time with his family, so two AI hosts take over the feed. Nobody on Brian’s team prompted or directed them. They chose to turn the microphone around and dissect Brian’s own book, OPERATE: Escape the Finisher’s Trap and Build a Business That Runs Without You. They cover the stories behind it, including a Christmas Eve drive through a snowstorm to fix a client’s email server, a roast beef shop owner asking “what’s next?”, and a dorm room TV playing Google Analytics 24/7. They also break down all seven pillars of the OPERATE Framework, which helps you stop being the bottleneck and build a business that runs beautifully without you.

✨ Why This Matters for You
The OPERATE Framework is a game-changer for entrepreneurs because:

• It names the “operator ceiling,” the point where your own ability to get things done is what stops your business from growing.
• It moves you from finisher to architect, so you design the systems others use to finish the work.
• It ends the feast-or-famine cycle by making visibility a constant current instead of a light switch.
• It shows how automation can protect the human touch instead of replacing it.
• It gives you practical tools for handing over real decisions to your team, including decision thresholds and the 4 D’s.

📝 Key Takeaways

• Be the Architect, Not the Finisher. A founder is like a rocket’s booster stage: essential to get off the ground, but dead weight if it never detaches. Your highest value is designing the systems, not finishing every task.
• Become a Lighthouse, Not a Lifeboat. Good work doesn’t market itself. Brian’s Outreach Equation is Message × Medium × Motion, and motion is what keeps your message going out while you sleep or deliver client work.
• Pipelines Are Relationship Journeys. Capture, nurture, convert. Automation doesn’t replace empathy. It makes sure empathy happens consistently, which is how Brian earned a “your timing is spooky” reply from a prospect.
• Delivery Runs on Clarity, Cadence, and Capacity. Hustle hides broken systems. Retention then runs on Experience, Engagement, and Evolution, and continuity offers give clients a systematized bridge to their next level.
• Leverage Beats Efficiency. Efficiency gets today’s tasks done. Leverage changes what you’re capable of for the next decade. Brian’s AI teammates, Micaela and Andrew, handle the mechanical work so the humans can do the meaningful work.
• Respect the Empathy Line. Never automate hiring decisions, creative reviews, apologies, or gratitude. Automation handles the movement of data, not the meaning of the relationship.
• Track All Three Layers of Telemetry. Operational (the daily pulse), performance (the scoreboard), and personal (your energy, sleep, and team morale). Don’t track vanity metrics.
• Mistakes Are Tuition. Use Brian’s enablement trifecta of Empowerment, Education, and Environment, and follow the 4 D’s: Document → Delegate → Develop → Disappear (then distribute decisions). Set decision thresholds, like the Ritz-Carlton’s $2,000 rule, scaled to your business.

🚀 Put It Into Action
This week, don’t try to build all seven pillars at once. Pick one friction point and build one system:

• Block off one hour in your calendar.
• Name the single biggest bottleneck in your business. Is it a leaky pipeline, feast-or-famine outreach, or a team that waits on you for every decision?
• Write down every step you take to handle that bottleneck manually.
• Turn that document into a system. Automate the data movement, delegate the execution, or set a decision threshold (e.g., “If it costs under $200 to fix, you have the authority to decide”).
• Then ask yourself the episode’s closing question: when your business no longer needs you to be the hero, what will you do with your life?

🔗 Stay Connected

• Subscribe to the show so you never miss an episode
• Grab your copy of OPERATE: Escape the Finisher’s Trap and Build a Business That Runs Without You
• Connect with Brian on Instagram @imetbrian
• Share this episode with a fellow entrepreneur who’s stuck being the hero of their 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

As Q4 kicks into high gear, the pressure is on to launch new products, create flashy promos, and find new customers to finish the year strong. But what if your biggest opportunities aren't in what’s new, but in what’s old? In this Solo Sunday episode, Brian shares his all-time favorite, most effective, and deceptively simple strategy for generating massive momentum: the reactivation campaign. Forget overcomplicating things. Brian breaks down why reaching out to past prospects—even the ones who ghosted you or said no—is the single most powerful move you can make right now. This is the exact tactic he uses across all his businesses and with his clients to turn forgotten conversations into closed deals.

✨ Why This Matters for You

The reactivation campaign is a game-changer for entrepreneurs because:

• It’s a low-cost, high-return strategy that doesn't require a big ad budget.
• It leverages your most valuable asset: the list of people who already know you exist.
• It reframes rejection. A "no" is rarely permanent; it's usually just "not now."
• It simplifies your marketing by focusing on warm leads instead of constantly chasing cold ones.
• It generates quick wins and tangible results, building the momentum you need to crush your end-of-year goals.

📝 Key Takeaways

• Reactivate > Chase. Your old leads, proposals, and conversations are a goldmine. The easiest path to revenue is often through reconnecting, not just prospecting.
• "No" Often Means "Not Now." Don't be afraid to follow up with people who rejected you, went with someone else, or ghosted you. Circumstances change, and your check-in might be perfectly timed.
• Conversation Before Conversion. The goal of a reactivation email isn't to make a hard sale. It’s simply to restart the conversation, see where they are, and understand their current needs.
• Systemize Your Past. Go through your emails, calendar, and CRMs to build a master list of every prospect you didn't get to work with. AI tools can make this process faster than ever.
• Simplicity Wins. In business, it’s often the boring, fundamental actions that produce the best results. Stop overcomplicating your strategy and focus on what works.

🚀 Put It Into Action

This week, schedule your own reactivation campaign:

• Block off one hour in your calendar.
• Go through your sent emails, old proposals, and calendar invites from the past 1-2 years.
• Create a simple list of at least 10 people who showed interest but never moved forward.
• Draft a short, non-salesy email checking in. Ask how their year has been and if they ever solved the problem you originally discussed. Send it and see what conversations bubble up.

🔗 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 a simple, powerful way to boost their Q4 revenue

In this special Collab Week episode of Wantrepreneur to Entrepreneur, eight founders come together to answer one deeply honest question:

Take us back to a lean season in your business. How did you get through it, and how do you prepare differently now?

Some are in a lean season right now. Some are still learning from their first one. Others have watched their busy seasons and slow seasons flip on them. It’s a wide-ranging episode about relationships, pipelines, cash, self-care, and why the best time to prepare for a lean season is before you’re in one.

For any wantrepreneur or entrepreneur wondering what to do when the pipeline goes quiet, or bracing for the next slow stretch, this episode is for you. You’ll walk away with practical ways to stay steady, stay visible, and keep building when business isn’t moving at the pace you want.

✨ What You’ll Take Away

In this episode, you’ll learn:

• Why lean seasons can be financial, human, or about impact, and how self-care keeps you steady through all of them
• Why doing more is the wrong instinct when cash gets tight, and how to decide what to cut before you have to
• How to build relationships before you need them and use slow periods to reconnect and strengthen your processes
• How to map your clients’ seasonal patterns so you can ramp up new channels before your own slow stretch
• Why a single point of dependency is risky, and how low overhead buys you time to adapt
• How to treat building the business as the work, even when the calendar is empty (or too full)

🎙️ Meet the Collab Week Contributors

Kacy Webster — Profit Quiver

Kacy Webster is a Business Transformation Strategist and Certified AI Consultant who helps leaders aim precisely at what matters most: people first, then technology. With 30+ years of executive leadership across higher education, workforce development, and enterprise transformation, she has held senior roles including Regional Market President, Campus Academic Dean, and Senior Director of Market Strategy & Insights for a nationally recognized assessment organization. Through Profit Quiver and The PrecisionX System, Kacy partners with leadership teams using her 12 Domains of Human-First AI Adoption, a framework that starts with culture, alignment, and readiness, not just technology.

Connect with Kacy: https://www.profitquiver.com/

Drew Dorenfest — Client Magnet CRM

Drew Dorenfest is a marketing expert who has worked with global brands such as Netflix, Apple, Warner Bros., and the NFL as a video editor. Today, through Client Magnet CRM, he helps small business owners get found online with SEO, GEO, and automation. That means more clients, more 5-star reviews, and more sales without having to create social content nonstop.

Connect with Drew: https://clientmagnetcrm.com/

Anne Gillaspie — Fix & Form

Anne Gillaspie is a global keynote speaker, truth disruptor, and creator of SHARE YOUR FEAR™, a movement making fear less scary and truth easier to tell. A 12-year entrepreneur, CEO and founder of Fix & Form Branding Firm, and host of the top-ranked OnlyFounders podcast, she’s also a brand therapist to founders and executives. Through provocative storytelling, unexpected dance, and radically human experiences, Anne helps audiences stop performing who they think they should be and start telling the truth about who they actually are.

Connect with Anne:

• https://theannegillaspie.com/
• https://fixandform.com/

Rami Akeela — Nera Systems

Rami Akeela is the founder of Nera Systems, a confidential AI company that helps enterprises use AI on their most sensitive data. With 20+ years at the intersection of hardware, software, and cryptography and PhDs in electrical and computer engineering, Rami is a deep-tech builder with a record of solving problems before the market knows it has them. He previously founded DZK, the first company to build zero-knowledge proof systems.

Connect with Rami: https://nera.systems/

Heather Waisanen — Coastal Maverick

Heather Waisanen is the founder of Coastal Maverick, a woman-owned, boutique out-of-home advertising agency helping brands stand out beyond the screen. With more than a decade of experience across the client, agency, and media owner sides of advertising, she launched Coastal Maverick after being laid off from her role as a senior media planner. Now in her fourth year of entrepreneurship, Heather leads nationwide campaigns while staying deeply involved in Jacksonville’s business community. She’s a JAX Chamber Small Business Leader of the Year and a member of the inaugural 2026 Visionaries 200 class.

Connect with Heather: https://www.coastalmaverick.com/

Drew Mehta — ThinkFraction

After 20+ years in corporate, Drew Mehta founded ThinkFraction to help owner-operated businesses fix the leaks in their back-end workflows and bring AI into their day-to-day in a practical way. His approach pairs advisory with implementation and education, with no hype, to grow revenue, lower costs, and improve quality. He’s also learning to be an entrepreneur himself, and he’s in his first full year of running his own business.

Connect with Drew:

• https://www.linkedin.com/in/dhroovmehta/
• Website: ThinkFraction.xyz

Sara Reece — Workmind

Sara Reece is the CEO and Co-Founder of Workmind, where she helps organizations use practical, operations-first automation to eliminate friction and grow without adding headcount at the same pace. Over the last seven years, she has designed and implemented automation with organizations ranging from nonprofits and small businesses to franchise systems and Fortune 500 enterprises. Her career has spanned journalism, television broadcasting, environmental research, and technology. Sara is the author of The Practical Path to Operational Automation and has appeared on Wantrepreneur to Entrepreneur, It Starts with Joy LIVE, and Level 10 Leadership. She has also presented at The Business Show Miami and Akerman’s Global Franchising Summit in Denver.

Connect with Sara:

• https://workmind.cloud/
• https://www.saralreece.com/

Mike Gross — Michael J. Gross LLC

Mike Gross is a trainer, training provider, consultant, and auditor who helps organizations make sense of ISO standards and apply them in a practical way. With over 35 years of experience, including steady growth into executive leadership roles, he focuses on building understanding through training first, then supporting organizations as they refine and improve their systems. He started Michael J. Gross LLC and Management System Certification Training Solutions about seven years ago after finishing his corporate career. As a committed solopreneur, his approach is straightforward: build on what already works, keep it practical, and leave people more capable than when he started.

Connect with Mike: https://mj-gross.com/

Ever frantically searched for your keys, wallet, or even your luggage at the airport? Daniel Daoura, the founder and CEO of Pebblebee, transformed that universal feeling of anxiety into a global tech company. Drawing on over a decade of experience developing tracking systems for military assets at Boeing, Daniel applied his deep expertise to solve an everyday problem. This episode is a masterclass in turning specialized knowledge into a consumer-focused brand, navigating the complexities of hardware manufacturing, and having the perseverance to build something truly innovative. You'll learn how Daniel led Pebblebee to become the first company to create a universal tracker that works seamlessly with both Apple and Google, and how his personal mission for his family's safety is now pushing the industry into its next frontier: personal safety devices.

💡 What You'll Take Away For YOUR Business

• 🚀 How to translate high-level enterprise or military-grade experience into a scalable consumer product.
• 🤝 The art of navigating partnerships with tech giants like Apple and Google to create a universally compatible product.
• 💡 Why your most personal pain points (like losing your keys or worrying about your family's safety) are often your most powerful business ideas.
• 📈 How to strategically expand your product line into new verticals that align with your core mission of providing value and peace of mind.
• 🧠 The founder's discipline: learning when to say "no" to good ideas to maintain focus and execute on the great ones.
• 🔋 How being the first to innovate with features like rechargeability can create a massive competitive advantage in a crowded market.
• 🌍 The gritty reality of building a global hardware company, from managing manufacturing and certifications to providing world-class customer support.

📝 About Daniel Daoura

Daniel Daoura is the Founder and CEO of Pebblebee, a visionary leader in the trackables and personal safety industry. His journey began with a focus on predicting satellite communication traffic for military asset tracking systems, which led him to a decade-long career at Boeing leading teams developing global tracking technology. Inspired by a personal moment of losing his keys, Daniel leveraged his immense experience to create Pebblebee, helping people track what matters most. With over 40 patents to his name, Daniel brings a unique perspective shaped by his technical genius, his personal experiences growing up in Beirut, and his dedication as a father.

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

"Perseverance. Don't give up. When you believe in something, just continue to find ways to solve that challenge."

📢 Memorable Quotes

• "What excites me is adding value in this economy and creating products that people really use and feel that is adding peace of mind to them." – Daniel Daoura
• "A good idea is only the beginning, and especially in our space, since we do hardware. I mean, it requires patience, capital, certifications, and manufacturing." – Daniel Daoura
• "Part of being a father—my daughter just started college... I want her to have a simple way to, you know, feel safe... That's why safety became a thing for Pebblebee." – Daniel Daoura

💡 Actionable Takeaways

• ✅ Solve Your Own Problem: Look at the daily frustrations and anxieties in your own life. Your most authentic and powerful business idea might be hidden there.
• ✅ Create Universal Value: Don't force your customers into one ecosystem. If you can, build products that offer flexibility and value to everyone, like Pebblebee did with Apple and Google compatibility.
• ✅ Reinvest in Innovation: Adopt a mindset of sustainable growth. Use profits to fuel R&D and stay ahead of the curve, rather than just maximizing cash reserves.
• ✅ Let Your Mission Guide Expansion: When considering a new product or service, ask if it truly aligns with your company's core mission. For Pebblebee, moving from tracking items to personal safety was a natural extension of providing "peace of mind."
• ✅ Don't Underestimate Perseverance: The next time you hit a wall, remember Daniel's advice. Give it time, break the problem down, and just keep taking the next step forward.

🔗 Links & Resources

• Website: https://pebblebee.com
• Connect with Daniel on LinkedIn
• Follow Pebblebee on LinkedIn

In this episode, Brian sits down with Micah Alexander, the 22-year-old co-founder of Junior Innovators, a company revolutionizing entrepreneurship education in K-12 schools. Micah shares his powerful journey from launching teenage businesses like snow shoveling and t-shirt companies to building a national education venture that teaches students to do business, not just study it. This episode is a masterclass in the "ready, fire, aim" philosophy, emphasizing that the best way to learn entrepreneurship is by getting in the weeds, creating value, and embracing failure as a critical learning tool. For any wantrepreneur feeling stuck in the planning phase, Micah’s story and insights are the ultimate permission slip to stop waiting and start doing.

💡 What You'll Take Away For YOUR Business

• 🚀 Why "Ready, Fire, Aim" is a more effective startup strategy than endless planning and analysis.
• 💡 How to find a scalable business idea by focusing on solving one small problem, not trying to build a billion-dollar company from day one.
• 💰 The truth about startup capital: why creating value for a customer is the only thing you need to get started, even with $0.
• 🧠 How to reframe failure as a learning opportunity that is just as valuable (if not more so) than early success.
• 🗣️ The simple yet powerful strategy of talking to people to conduct real-world market research without even realizing it.
• 🔥 Why high school (or any early stage) is the perfect low-risk environment to experiment, fail, and build entrepreneurial muscle.
• 📈 The difference between learning business theory and actually doing business—and why the latter is the only path to real growth.

📝 About Micah Alexander

Micah Alexander is the co-founder of Junior Innovators, an education company dedicated to bringing hands-on entrepreneurship curriculum to K-12 schools. A serial entrepreneur since he was 16, Micah experienced firsthand the gap between academic business classes and the real-world action required to build a venture. Alongside his co-founder Logan, he bootstrapped Junior Innovators while still in college to give students the chance to fail, learn, and succeed by building real companies. His unique perspective as a young founder working with the next generation of innovators provides a fresh and urgent take on what it truly means to be an entrepreneur.

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

"Just try something. You can't come up with an idea unless you have a problem to solve... Entrepreneurship is one of those things that is for everybody and anyone can go out and try to create value for someone else."

📢 Memorable Quotes

• “A lot of entrepreneurs, especially, think of a business idea as being this big thing. And they need all this funding to get started. Like you don't. You need to figure out a way to create value for someone.” – Micah Alexander
• “If a student can clearly articulate why their business failed… that's just as good as someone who made $500 their first time. That is the same level of learning.” – Micah Alexander
• “There are so many businesses that have solutions to nobody's problem. And a problem is the first thing that you have to figure out when you're trying to come up with a business idea.” – Micah Alexander

💡 Actionable Takeaways

• Identify one problem in your immediate community or circle of friends this week. Don't think about the solution yet—just define the problem.
• Talk to five people who experience this problem. Ask them questions to understand it at its core. This is your first step in market research.
• Take one small, tangible step on your business idea today. Don't wait for permission. This could be creating a landing page, making one sales call, or designing a simple prototype.
• Look back at a past "failure" in your career or business journey. Write down three specific lessons you learned from it that you still apply today.

🔗 Links & Resources

• Website: https://junior-innovators.org
• Connect with Micah on LinkedIn
• Follow Junior Innovators LLC on LinkedIn

In this episode, Brian sits down with Matt Justice, a career finance expert turned AI founder who is revolutionizing how SaaS companies interact with their own numbers. Matt shares his journey from feeling the intense frustration of data wrangling in corporate finance to founding SMPL.ai, a platform that gives teams their time back and empowers them with true financial intelligence. This isn't just a talk about spreadsheets and compliance; it's a masterclass in shifting your mindset to see finance as a strategic tool for making faster, smarter decisions. For any wantrepreneur or entrepreneur tired of flying blind, Matt’s story and insights will show you how to connect the dots in your data, build a business founded on personal experience, and leverage AI to scale as a solo founder.

💡 What You'll Take Away For YOUR Business

• Financial Truth vs. Financial Intelligence: Understand the crucial difference and why your business needs both to survive and thrive.
• Connecting the Silos: Discover how to use AI to integrate your pipeline, bookings, revenue, and cash flow for a single, reliable source of truth.
• The Power of Timely Data: Learn why having perfect information too late is useless (the "Titanic" principle) and how to get real-time insights for your business.
• A Solo Founder’s MVP Strategy: Hear how Matt built a proof-of-concept in just a few days and used a "pre-dinner barbecue" to get brutally honest early feedback.
• Milestones Over Timelines: Why focusing on achieving the next critical milestone is more effective than getting bogged down by rigid, long-term projections.
• The Unbeatable Motivator: Learn how to ground your business idea in your own blood, sweat, and tears to create a vision so clear that motivation is never a question.
• AI as Your Co-founder: See practical examples of how a solo founder uses AI as an extension of his team to manage everything from customer support to coding.

📝 About Matt Justice

Matt Justice is the founder of SMPL.ai, an AI-powered financial intelligence platform for growing SaaS companies. With a deep career spanning FP&A, accounting, and strategic finance, he has spent years in the trenches building the data systems and reporting infrastructure that finance teams rely on. Matt turned his professional frustration with disconnected systems and manual data wrangling into a powerful mission: to give finance professionals their time back and empower them to make better, faster decisions. His firsthand experience makes him a uniquely insightful guest on solving real-world business problems with technology.

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

"When you go out and you start this, make sure that it's something founded in your experience and your beliefs...and then I think motivation never becomes a topic again."

📢 Memorable Quotes

• "The Titanic had perfect information, it was just late." – Matt Justice
• "The more you can stay down, it just means you're learning... the more lessons you can learn now, I guess the longer you stay in the highs." – Matt Justice
• "I never thought in a million years creating a software platform was going to be the easy part." – Matt Justice

💡 Actionable Takeaways

• ✅ Audit Your Data's Timeliness: Ask yourself if your financial reports are helping you make decisions for next month or if they're just a history lesson. Identify the biggest bottleneck in getting timely information.
• ✅ Reconnect With Your "Why": Write down the personal frustration or experience that led you to start (or want to start) your business. Use this as your north star for all future decisions.
• ✅ Identify Your Next Milestone: Forget the 5-year plan for a moment. What is the single most important milestone you need to hit to move your business forward? Focus all your energy there.
• ✅ Delegate One Task to AI: Find one repetitive, time-consuming task in your day (writing email drafts, summarizing notes, troubleshooting code) and find an AI tool to handle it. Start building your "extra pair of arms."

🔗 Links & Resources

• Website: https://www.smpl-ai.com
• Connect with Matt on LinkedIn
• Follow SMPL.ai on LinkedIn

What if you could condense weeks of expert-level analysis into just a few minutes? Former McKinsey Partner Raman Julka is doing exactly that. In this episode, he breaks down his journey from advising global corporations to building two AI-native companies, http://ValueChaser.ai and http://Chance-Me.ai, with a radically lean team. This conversation is a masterclass in how AI is shattering the traditional barriers to entry in business. You’ll learn why your human judgment, not coding skills, is your most valuable asset and how to leverage your unique expertise to build a scalable business in this new economic landscape.

💡 What You'll Take Away For YOUR Business

• 🚀 How to transform weeks of expert analysis into minutes of automated work using AI, freeing up your time for high-value strategic decisions.
• 🤖 Why your human judgment and industry experience are becoming your most critical assets in an AI-driven world.
• 💰 The new economics of entrepreneurship: Learn how to build an enterprise-grade business with a lean team and minimal coding knowledge.
• 📈 Why distribution and credibility are the new "moats" for your business when technology is no longer a barrier to entry.
• 🧠 How to leverage your existing domain expertise to build a scalable, AI-native product that solves a real-world problem.
• 🎯 The seismic shift from "brand name" to "guaranteed impact" and how you can compete with established giants as a small service provider.
• 🛠️ How to operate like a "human + AI" team to massively accelerate your path from idea to market.

📝 About Raman Julka

Raman Julka is an entrepreneur and former McKinsey partner who spent 13 years advising major companies on technology and large-scale transformations. He left his corporate career to pursue a powerful hypothesis: that AI could turn complex, expert-driven work into scalable, accessible products. As the founder and CEO of http://ValueChaser.ai and http://Chance-Me.ai, Raman is proving that very small teams can now build businesses that previously required large organizations, offering a unique perspective that blends high-level corporate strategy with scrappy, hands-on startup execution.

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

"Perfection is the enemy of getting it done."

📢 Memorable Quotes

• “For me, AI replaces the part that's repeatable, that's actually mundane, and it allows you to apply the human element in a much longer time frame in a much more effective way.” – Raman Julka
• “As it becomes easier to build many businesses and ideas, what really differentiates is the distribution.” – Raman Julka
• “How can I build a $100 million ARR business without requiring 100 additional people?” – Raman Julka

💡 Actionable Takeaways

• ✅ Identify the most mundane, repeatable tasks in your business this week and explore AI tools to automate them.
• ✅ Stop waiting for your idea to be perfect. Launch a minimum viable product (MVP) to a small group of pilot users this month to gather crucial feedback.
• ✅ Re-evaluate your business's "moat." If it's just your technology, start building your distribution channels and personal brand credibility now.
• ✅ Practice working with AI. Instead of just asking for answers, learn to provide deep context and use your expertise to guide AI tools toward superior outputs.

🔗 Links & Resources

• http://ValueChaser.ai website: http://valuechaser.ai/
• http://Chance-Me.ai website: http://Chance-Me.ai
• Connect with Raman on LinkedIn
• Follow ValueChaser.ai on LinkedIn