Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

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