Brian Lofrumento reveals everything you need to go from wantrepreneur – or someone who WANTS to own their own business – to a money-making, action-taking entrepreneur. Discover exactly how to start a business and build a raving audience of fans and customers who want to buy your stuff, and learn exactly how to best serve your customers and clients by building a customer-centric line of products and services. Brian has built multiple six-figure businesses, including a six-figure SEO agency at the age of 24, and now helps thousands of entrepreneurs from around the world grow, automate, and scale their businesses by implementing high-converting marketing strategies and systems into their businesses. Visit the show online and get a free copy of the book, Wantrepreneur to Entrepreneur, at TheWantrepreneurShow.com. Our show is made possible by the financial, time, and knowledge contributions of our amazing guests. Together with the Wantrepreneur to Entrepreneur host and team, our guests believe in the power of entrepreneurs lifting up other entrepreneurs, and their contributions make it possible for us to reach wantrepreneurs and entrepreneurs all over the world ad-free.
Site
RSS
Apple
Data updated on 05/11/2026
Recent rankings
Latest chart positions across Apple Podcasts and Spotify rankings.
Shared links between episodes and podcasts
Links found in episode descriptions and other podcasts that share them.
1611: Your Team is Stuck? You Might Be the Problem (Here's How to Fix It) w/ LaToshia Ngu
Wednesday, November 4, 2026 • Duration 31:58
Are you a leader, or just in a leadership role? In this powerful episode, we sit down with Army veteran and brand strategist LaToshia Ngu to dismantle the myth of the "natural-born leader." LaToshia shares her journey from the military to entrepreneurship, revealing how her experiences taught her that true leadership is a learned skill rooted in listening, adapting, and empowering others. This episode is a must-listen for any entrepreneur who wants to build a thriving company culture, whether you're a solopreneur or leading a growing team. LaToshia breaks down complex leadership challenges into simple, actionable steps, showing you how to fix bottlenecks, build trust, and ultimately create a business that leaves a legacy.
💡 What You'll Take Away For YOUR Business
🚀 The "Stop, Look, Listen" Framework: A simple yet powerful method to effectively assess and lead in any new business situation or role.
💪 How to Build a Culture of Accountability: Learn why creating a safe space for mistakes is the fastest way to foster innovation and growth.
🔑 Why Admitting "You Are the Problem" is Your Greatest Strength: Discover how radical accountability can unlock solutions to your biggest business challenges.
📈 Practical Strategies for Leading Remote Teams: Learn how to keep your team aligned and motivated by focusing on a crystal-clear mission, vision, and values.
🌱 How Solopreneurs Can Build Leadership Skills from Day One: Get ahead of the curve by developing crucial leadership habits before you even make your first hire.
🏆 How to Define Success on Your Own Terms: Escape the comparison trap and build a business that truly aligns with your personal and professional goals.
📝 About LaToshia Ngu
LaToshia Ngu is the founder of LoveBug Branding, where she helps growing businesses build leaders, not bottlenecks. As an 8-year Army veteran, wife, and homeschooling mother, she brings a unique and powerful perspective to the world of brand strategy and organizational development. LaToshia’s zone of genius is making complicated problems simple, with a special knack for identifying where teams are stuck and providing the clarity needed to move forward. Her approach is grounded in real-world experience, proving that great leadership isn’t about having all the answers, but about knowing how to listen, learn, and empower your people.
🎯 LaToshia’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Define success for yourself."
In a world filled with noise telling you what you should be doing, LaToshia’s most powerful advice is to create your own definition of success and get tunnel vision on achieving it.
📢 Memorable Quotes
“Being in a leadership role does not make you a leader.” – LaToshia Ngu
“Sometimes the leader, you are the problem, and it's hard to see that. But when you see that you're the problem, you have to be willing and able and acceptable to change things for the betterment of your company and the people under you.” – LaToshia Ngu
“You can wake up in the morning, and sometimes success for me is simply, I wrote a new copy. Whoo! Well, got that done. That was success for me for that day.” – LaToshia Ngu
💡 Actionable Takeaways
✅ Implement the "Stop, Look, and Listen" practice this week. Before making your next big decision, pause to observe the situation, look at what’s working (and what's not), and intentionally listen to feedback from your team or customers.
✅ Define what success means for YOU. Write down 3-5 metrics for success that have nothing to do with what you see online (e.g., freedom of time, impact on one client, learning a new skill).
✅ Review your company's mission, vision, and values. Ask yourself: Are these clear? Does my team (or do my clients) understand them? Are my daily actions aligned with them?
✅ Practice proactive encouragement. This week, publicly praise a team member, collaborator, or even a client for a specific achievement using your primary communication channel.
1610: The #1 Mindset Shift to Unlock AI's True Potential for Your Business w/ Leila Kaneda
Tuesday, November 3, 2026 • Duration 32:58
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.
1609: Stop Boring Marketing: How Gamification Turned 300 Executives Into Kids w/ Alejandro Guzman
Monday, November 2, 2026 • Duration 34:30
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.
1608: Do NOT take this person for granted!
Monday, November 2, 2026 • Duration 12:07
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:
1607: How have you put your entrepreneurial GHOSTS to rest!? (COLLAB EPISODE!)
Friday, October 30, 2026 • Duration 35:09
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.
1606: This Educator-Turned-Founder is Saving Critical Thinking w/ Jordan Wolff
Thursday, October 29, 2026 • Duration 33:29
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
1605: From Art Director to Tech CEO: The Power of Solving Your Own Problem w/ Rayne Chapman
Wednesday, October 28, 2026 • Duration 32:44
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
1604: This AI Assistant Knows Your Team Better Than You Do w/ Masumi Nakamura
Tuesday, October 27, 2026 • Duration 30:42
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
1603: Are You in the Weeds? How to Think Strategically + One Level Higher w/ Mark McSweeney
Monday, October 26, 2026 • Duration 34:05
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
1602: You'll get PUNISHED as the FINISHER... (AI took this episode over!)
Monday, October 26, 2026 • Duration 21:08
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.
🎯 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.
🎯 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.
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
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.
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.
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.
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.
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.
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.
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.
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.
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.
"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.
“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.
"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.
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.
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
Related Shows Based on Content Similarities
Discover shows related to Wantrepreneur to Entrepreneur | Start and Grow Your Own Business, based on actual content similarities. Explore podcasts with similar topics, themes, and formats, backed by real data.
