Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

Brian Lofrumento
  • 4.9 (155)
  • Marketing
  • Semiweekly

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.

  1. 2d ago

    1607: How have you put your entrepreneurial GHOSTS to rest!? (COLLAB EPISODE!)

    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 paysWhy how you treat the people building your business deserves as much attention as any strategy decisionHow to walk away from a growth path that’s out of alignment, even with funding on the tableWhy years of industry expertise don’t automatically make you good at pricing your own workHow to stay generous without letting people build on you instead of with youWhy turning off the marketing isn’t the same as killing your first businessWhy 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/

  2. 3d ago

    1606: This Educator-Turned-Founder is Saving Critical Thinking w/ Jordan Wolff

    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.comTry Typed by Me for freeConnect with Jordan on LinkedInFollow Typed by Hand on LinkedInFollow Typed by Hand on FacebookFollow Typed by Hand on Instagram

    1606: This Educator-Turned-Founder is Saving Critical Thinking w/ Jordan Wolff

  3. 4d ago

    1605: From Art Director to Tech CEO: The Power of Solving Your Own Problem w/ Rayne Chapman

    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.comConnect with Rayne on LinkedInFollow Neat Inspo on LinkedIn

    1605: From Art Director to Tech CEO: The Power of Solving Your Own Problem w/ Rayne Chapman

  4. 5d ago

    1604: This AI Assistant Knows Your Team Better Than You Do w/ Masumi Nakamura

    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.comConnect with Masumi on LinkedInFollow askMyu on LinkedIn

    1604: This AI Assistant Knows Your Team Better Than You Do w/ Masumi Nakamura

  5. 6d ago

    1603: Are You in the Weeds? How to Think Strategically + One Level Higher w/ Mark McSweeney

    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.coConnect with Mark on LinkedInFollow Envisioned Future LLC on LinkedIn

    1603: Are You in the Weeds? How to Think Strategically + One Level Higher w/ Mark McSweeney

  6. Oct 26

    1602: You'll get PUNISHED as the FINISHER... (AI took this episode over!)

    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 episodeGrab your copy of OPERATE: Escape the Finisher’s Trap and Build a Business That Runs Without YouConnect with Brian on Instagram @imetbrianShare this episode with a fellow entrepreneur who’s stuck being the hero of their own business

  7. Oct 23

    1601: Just when you think it FLOPPED, here's how it can work out... (COLLAB EPISODE!)

    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 businessWhy setting expectations up front matters most when you’re selling AIHow a failed contractor relationship can push you to build skills you never planned to learnWhy asking the right questions saves you time and moneyWhat “the deal dies in maybes” means for founders still building their sales muscleWhy 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/

  8. Oct 22

    1600: From Army Officer to AI Founder: A Masterclass in Mission-Driven Entrepreneurship w/ Nils Olsen

    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.aiConnect with Nils on LinkedInFollow Six Tango on LinkedIn

    1600: From Army Officer to AI Founder: A Masterclass in Mission-Driven Entrepreneurship w/ Nils Olsen
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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.

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