Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

In this special Collab Week episode of Wantrepreneur to Entrepreneur, eight founders come together to answer one deeply honest question:
Take us back to a lean season in your business. How did you get through it, and how do you prepare differently now?
Some are in a lean season right now. Some are still learning from their first one. Others have watched their busy seasons and slow seasons flip on them. It’s a wide-ranging episode about relationships, pipelines, cash, self-care, and why the best time to prepare for a lean season is before you’re in one.
For any wantrepreneur or entrepreneur wondering what to do when the pipeline goes quiet, or bracing for the next slow stretch, this episode is for you. You’ll walk away with practical ways to stay steady, stay visible, and keep building when business isn’t moving at the pace you want.
✨ What You’ll Take Away
In this episode, you’ll learn:
Why lean seasons can be financial, human, or about impact, and how self-care keeps you steady through all of them
Why doing more is the wrong instinct when cash gets tight, and how to decide what to cut before you have to
How to build relationships before you need them and use slow periods to reconnect and strengthen your processes
How to map your clients’ seasonal patterns so you can ramp up new channels before your own slow stretch
Why a single point of dependency is risky, and how low overhead buys you time to adapt
How to treat building the business as the work, even when the calendar is empty (or too full)
🎙️ Meet the Collab Week Contributors
Kacy Webster — Profit Quiver
Kacy Webster is a Business Transformation Strategist and Certified AI Consultant who helps leaders aim precisely at what matters most: people first, then technology. With 30+ years of executive leadership across higher education, workforce development, and enterprise transformation, she has held senior roles including Regional Market President, Campus Academic Dean, and Senior Director of Market Strategy & Insights for a nationally recognized assessment organization. Through Profit Quiver and The PrecisionX System, Kacy partners with leadership teams using her 12 Domains of Human-First AI Adoption, a framework that starts with culture, alignment, and readiness, not just technology.
Connect with Kacy: https://www.profitquiver.com/
Drew Dorenfest — Client Magnet CRM
Drew Dorenfest is a marketing expert who has worked with global brands such as Netflix, Apple, Warner Bros., and the NFL as a video editor. Today, through Client Magnet CRM, he helps small business owners get found online with SEO, GEO, and automation. That means more clients, more 5-star reviews, and more sales without having to create social content nonstop.
Connect with Drew: https://clientmagnetcrm.com/
Anne Gillaspie — Fix & Form
Anne Gillaspie is a global keynote speaker, truth disruptor, and creator of SHARE YOUR FEAR™, a movement making fear less scary and truth easier to tell. A 12-year entrepreneur, CEO and founder of Fix & Form Branding Firm, and host of the top-ranked OnlyFounders podcast, she’s also a brand therapist to founders and executives. Through provocative storytelling, unexpected dance, and radically human experiences, Anne helps audiences stop performing who they think they should be and start telling the truth about who they actually are.
Connect with Anne:
https://theannegillaspie.com/
https://fixandform.com/
Rami Akeela — Nera Systems
Rami Akeela is the founder of Nera Systems, a confidential AI company that helps enterprises use AI on their most sensitive data. With 20+ years at the intersection of hardware, software, and cryptography and PhDs in electrical and computer engineering, Rami is a deep-tech builder with a record of solving problems before the market knows it has them. He previously founded DZK, the first company to build zero-knowledge proof systems.
Connect with Rami: https://nera.systems/
Heather Waisanen — Coastal Maverick
Heather Waisanen is the founder of Coastal Maverick, a woman-owned, boutique out-of-home advertising agency helping brands stand out beyond the screen. With more than a decade of experience across the client, agency, and media owner sides of advertising, she launched Coastal Maverick after being laid off from her role as a senior media planner. Now in her fourth year of entrepreneurship, Heather leads nationwide campaigns while staying deeply involved in Jacksonville’s business community. She’s a JAX Chamber Small Business Leader of the Year and a member of the inaugural 2026 Visionaries 200 class.
Connect with Heather: https://www.coastalmaverick.com/
Drew Mehta — ThinkFraction
After 20+ years in corporate, Drew Mehta founded ThinkFraction to help owner-operated businesses fix the leaks in their back-end workflows and bring AI into their day-to-day in a practical way. His approach pairs advisory with implementation and education, with no hype, to grow revenue, lower costs, and improve quality. He’s also learning to be an entrepreneur himself, and he’s in his first full year of running his own business.
Connect with Drew:
https://www.linkedin.com/in/dhroovmehta/
Website: ThinkFraction.xyz
Sara Reece — Workmind
Sara Reece is the CEO and Co-Founder of Workmind, where she helps organizations use practical, operations-first automation to eliminate friction and grow without adding headcount at the same pace. Over the last seven years, she has designed and implemented automation with organizations ranging from nonprofits and small businesses to franchise systems and Fortune 500 enterprises. Her career has spanned journalism, television broadcasting, environmental research, and technology. Sara is the author of The Practical Path to Operational Automation and has appeared on Wantrepreneur to Entrepreneur, It Starts with Joy LIVE, and Level 10 Leadership. She has also presented at The Business Show Miami and Akerman’s Global Franchising Summit in Denver.
Connect with Sara:
https://workmind.cloud/
https://www.saralreece.com/
Mike Gross — Michael J. Gross LLC
Mike Gross is a trainer, training provider, consultant, and auditor who helps organizations make sense of ISO standards and apply them in a practical way. With over 35 years of experience, including steady growth into executive leadership roles, he focuses on building understanding through training first, then supporting organizations as they refine and improve their systems. He started Michael J. Gross LLC and Management System Certification Training Solutions about seven years ago after finishing his corporate career. As a committed solopreneur, his approach is straightforward: build on what already works, keep it practical, and leave people more capable than when he started.
Connect with Mike: https://mj-gross.com/

Ever frantically searched for your keys, wallet, or even your luggage at the airport? Daniel Daoura, the founder and CEO of Pebblebee, transformed that universal feeling of anxiety into a global tech company. Drawing on over a decade of experience developing tracking systems for military assets at Boeing, Daniel applied his deep expertise to solve an everyday problem. This episode is a masterclass in turning specialized knowledge into a consumer-focused brand, navigating the complexities of hardware manufacturing, and having the perseverance to build something truly innovative. You'll learn how Daniel led Pebblebee to become the first company to create a universal tracker that works seamlessly with both Apple and Google, and how his personal mission for his family's safety is now pushing the industry into its next frontier: personal safety devices.
💡 What You'll Take Away For YOUR Business
🚀 How to translate high-level enterprise or military-grade experience into a scalable consumer product.
🤝 The art of navigating partnerships with tech giants like Apple and Google to create a universally compatible product.
💡 Why your most personal pain points (like losing your keys or worrying about your family's safety) are often your most powerful business ideas.
📈 How to strategically expand your product line into new verticals that align with your core mission of providing value and peace of mind.
🧠 The founder's discipline: learning when to say "no" to good ideas to maintain focus and execute on the great ones.
🔋 How being the first to innovate with features like rechargeability can create a massive competitive advantage in a crowded market.
🌍 The gritty reality of building a global hardware company, from managing manufacturing and certifications to providing world-class customer support.
📝 About Daniel Daoura
Daniel Daoura is the Founder and CEO of Pebblebee, a visionary leader in the trackables and personal safety industry. His journey began with a focus on predicting satellite communication traffic for military asset tracking systems, which led him to a decade-long career at Boeing leading teams developing global tracking technology. Inspired by a personal moment of losing his keys, Daniel leveraged his immense experience to create Pebblebee, helping people track what matters most. With over 40 patents to his name, Daniel brings a unique perspective shaped by his technical genius, his personal experiences growing up in Beirut, and his dedication as a father.
🎯 Daniel’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Perseverance. Don't give up. When you believe in something, just continue to find ways to solve that challenge."
📢 Memorable Quotes
"What excites me is adding value in this economy and creating products that people really use and feel that is adding peace of mind to them." – Daniel Daoura
"A good idea is only the beginning, and especially in our space, since we do hardware. I mean, it requires patience, capital, certifications, and manufacturing." – Daniel Daoura
"Part of being a father—my daughter just started college... I want her to have a simple way to, you know, feel safe... That's why safety became a thing for Pebblebee." – Daniel Daoura
💡 Actionable Takeaways
✅ Solve Your Own Problem: Look at the daily frustrations and anxieties in your own life. Your most authentic and powerful business idea might be hidden there.
✅ Create Universal Value: Don't force your customers into one ecosystem. If you can, build products that offer flexibility and value to everyone, like Pebblebee did with Apple and Google compatibility.
✅ Reinvest in Innovation: Adopt a mindset of sustainable growth. Use profits to fuel R&D and stay ahead of the curve, rather than just maximizing cash reserves.
✅ Let Your Mission Guide Expansion: When considering a new product or service, ask if it truly aligns with your company's core mission. For Pebblebee, moving from tracking items to personal safety was a natural extension of providing "peace of mind."
✅ Don't Underestimate Perseverance: The next time you hit a wall, remember Daniel's advice. Give it time, break the problem down, and just keep taking the next step forward.
🔗 Links & Resources
Website: https://pebblebee.com
Connect with Daniel on LinkedIn
Follow Pebblebee on LinkedIn

In this episode, Brian sits down with Micah Alexander, the 22-year-old co-founder of Junior Innovators, a company revolutionizing entrepreneurship education in K-12 schools. Micah shares his powerful journey from launching teenage businesses like snow shoveling and t-shirt companies to building a national education venture that teaches students to do business, not just study it. This episode is a masterclass in the "ready, fire, aim" philosophy, emphasizing that the best way to learn entrepreneurship is by getting in the weeds, creating value, and embracing failure as a critical learning tool. For any wantrepreneur feeling stuck in the planning phase, Micah’s story and insights are the ultimate permission slip to stop waiting and start doing.
💡 What You'll Take Away For YOUR Business
🚀 Why "Ready, Fire, Aim" is a more effective startup strategy than endless planning and analysis.
💡 How to find a scalable business idea by focusing on solving one small problem, not trying to build a billion-dollar company from day one.
💰 The truth about startup capital: why creating value for a customer is the only thing you need to get started, even with $0.
🧠 How to reframe failure as a learning opportunity that is just as valuable (if not more so) than early success.
🗣️ The simple yet powerful strategy of talking to people to conduct real-world market research without even realizing it.
🔥 Why high school (or any early stage) is the perfect low-risk environment to experiment, fail, and build entrepreneurial muscle.
📈 The difference between learning business theory and actually doing business—and why the latter is the only path to real growth.
📝 About Micah Alexander
Micah Alexander is the co-founder of Junior Innovators, an education company dedicated to bringing hands-on entrepreneurship curriculum to K-12 schools. A serial entrepreneur since he was 16, Micah experienced firsthand the gap between academic business classes and the real-world action required to build a venture. Alongside his co-founder Logan, he bootstrapped Junior Innovators while still in college to give students the chance to fail, learn, and succeed by building real companies. His unique perspective as a young founder working with the next generation of innovators provides a fresh and urgent take on what it truly means to be an entrepreneur.
🎯 Micah’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Just try something. You can't come up with an idea unless you have a problem to solve... Entrepreneurship is one of those things that is for everybody and anyone can go out and try to create value for someone else."
📢 Memorable Quotes
“A lot of entrepreneurs, especially, think of a business idea as being this big thing. And they need all this funding to get started. Like you don't. You need to figure out a way to create value for someone.” – Micah Alexander
“If a student can clearly articulate why their business failed… that's just as good as someone who made $500 their first time. That is the same level of learning.” – Micah Alexander
“There are so many businesses that have solutions to nobody's problem. And a problem is the first thing that you have to figure out when you're trying to come up with a business idea.” – Micah Alexander
💡 Actionable Takeaways
Identify one problem in your immediate community or circle of friends this week. Don't think about the solution yet—just define the problem.
Talk to five people who experience this problem. Ask them questions to understand it at its core. This is your first step in market research.
Take one small, tangible step on your business idea today. Don't wait for permission. This could be creating a landing page, making one sales call, or designing a simple prototype.
Look back at a past "failure" in your career or business journey. Write down three specific lessons you learned from it that you still apply today.
🔗 Links & Resources
Website: https://junior-innovators.org
Connect with Micah on LinkedIn
Follow Junior Innovators LLC on LinkedIn

In this episode, Brian sits down with Matt Justice, a career finance expert turned AI founder who is revolutionizing how SaaS companies interact with their own numbers. Matt shares his journey from feeling the intense frustration of data wrangling in corporate finance to founding SMPL.ai, a platform that gives teams their time back and empowers them with true financial intelligence. This isn't just a talk about spreadsheets and compliance; it's a masterclass in shifting your mindset to see finance as a strategic tool for making faster, smarter decisions. For any wantrepreneur or entrepreneur tired of flying blind, Matt’s story and insights will show you how to connect the dots in your data, build a business founded on personal experience, and leverage AI to scale as a solo founder.
💡 What You'll Take Away For YOUR Business
Financial Truth vs. Financial Intelligence: Understand the crucial difference and why your business needs both to survive and thrive.
Connecting the Silos: Discover how to use AI to integrate your pipeline, bookings, revenue, and cash flow for a single, reliable source of truth.
The Power of Timely Data: Learn why having perfect information too late is useless (the "Titanic" principle) and how to get real-time insights for your business.
A Solo Founder’s MVP Strategy: Hear how Matt built a proof-of-concept in just a few days and used a "pre-dinner barbecue" to get brutally honest early feedback.
Milestones Over Timelines: Why focusing on achieving the next critical milestone is more effective than getting bogged down by rigid, long-term projections.
The Unbeatable Motivator: Learn how to ground your business idea in your own blood, sweat, and tears to create a vision so clear that motivation is never a question.
AI as Your Co-founder: See practical examples of how a solo founder uses AI as an extension of his team to manage everything from customer support to coding.
📝 About Matt Justice
Matt Justice is the founder of SMPL.ai, an AI-powered financial intelligence platform for growing SaaS companies. With a deep career spanning FP&A, accounting, and strategic finance, he has spent years in the trenches building the data systems and reporting infrastructure that finance teams rely on. Matt turned his professional frustration with disconnected systems and manual data wrangling into a powerful mission: to give finance professionals their time back and empower them to make better, faster decisions. His firsthand experience makes him a uniquely insightful guest on solving real-world business problems with technology.
🎯 Matt’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"When you go out and you start this, make sure that it's something founded in your experience and your beliefs...and then I think motivation never becomes a topic again."
📢 Memorable Quotes
"The Titanic had perfect information, it was just late." – Matt Justice
"The more you can stay down, it just means you're learning... the more lessons you can learn now, I guess the longer you stay in the highs." – Matt Justice
"I never thought in a million years creating a software platform was going to be the easy part." – Matt Justice
💡 Actionable Takeaways
✅ Audit Your Data's Timeliness: Ask yourself if your financial reports are helping you make decisions for next month or if they're just a history lesson. Identify the biggest bottleneck in getting timely information.
✅ Reconnect With Your "Why": Write down the personal frustration or experience that led you to start (or want to start) your business. Use this as your north star for all future decisions.
✅ Identify Your Next Milestone: Forget the 5-year plan for a moment. What is the single most important milestone you need to hit to move your business forward? Focus all your energy there.
✅ Delegate One Task to AI: Find one repetitive, time-consuming task in your day (writing email drafts, summarizing notes, troubleshooting code) and find an AI tool to handle it. Start building your "extra pair of arms."
🔗 Links & Resources
Website: https://www.smpl-ai.com
Connect with Matt on LinkedIn
Follow SMPL.ai on LinkedIn

What if you could condense weeks of expert-level analysis into just a few minutes? Former McKinsey Partner Raman Julka is doing exactly that. In this episode, he breaks down his journey from advising global corporations to building two AI-native companies, ValueChaser.ai and Chance-Me.ai, with a radically lean team. This conversation is a masterclass in how AI is shattering the traditional barriers to entry in business. You’ll learn why your human judgment, not coding skills, is your most valuable asset and how to leverage your unique expertise to build a scalable business in this new economic landscape.
💡 What You'll Take Away For YOUR Business
🚀 How to transform weeks of expert analysis into minutes of automated work using AI, freeing up your time for high-value strategic decisions.
🤖 Why your human judgment and industry experience are becoming your most critical assets in an AI-driven world.
💰 The new economics of entrepreneurship: Learn how to build an enterprise-grade business with a lean team and minimal coding knowledge.
📈 Why distribution and credibility are the new "moats" for your business when technology is no longer a barrier to entry.
🧠 How to leverage your existing domain expertise to build a scalable, AI-native product that solves a real-world problem.
🎯 The seismic shift from "brand name" to "guaranteed impact" and how you can compete with established giants as a small service provider.
🛠️ How to operate like a "human + AI" team to massively accelerate your path from idea to market.
📝 About Raman Julka
Raman Julka is an entrepreneur and former McKinsey partner who spent 13 years advising major companies on technology and large-scale transformations. He left his corporate career to pursue a powerful hypothesis: that AI could turn complex, expert-driven work into scalable, accessible products. As the founder and CEO of ValueChaser.ai and Chance-Me.ai, Raman is proving that very small teams can now build businesses that previously required large organizations, offering a unique perspective that blends high-level corporate strategy with scrappy, hands-on startup execution.
🎯 Raman’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Perfection is the enemy of getting it done."
📢 Memorable Quotes
 “For me, AI replaces the part that's repeatable, that's actually mundane, and it allows you to apply the human element in a much longer time frame in a much more effective way.” – Raman Julka
“As it becomes easier to build many businesses and ideas, what really differentiates is the distribution.” – Raman Julka
“How can I build a $100 million ARR business without requiring 100 additional people?” – Raman Julka
💡 Actionable Takeaways
✅ Identify the most mundane, repeatable tasks in your business this week and explore AI tools to automate them.
✅ Stop waiting for your idea to be perfect. Launch a minimum viable product (MVP) to a small group of pilot users this month to gather crucial feedback.
✅ Re-evaluate your business's "moat." If it's just your technology, start building your distribution channels and personal brand credibility now.
✅ Practice working with AI. Instead of just asking for answers, learn to provide deep context and use your expertise to guide AI tools toward superior outputs.
🔗 Links & Resources
ValueChaser.ai website: http://valuechaser.ai/
Chance-Me.ai website: http://Chance-Me.ai
Connect with Raman on LinkedIn
Follow ValueChaser.ai on LinkedIn