Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

In this episode, serial entrepreneur Tess Michaels unveils the brilliant model behind Clasp, her venture-backed company that’s tackling the dual crisis of healthcare talent shortages and overwhelming student debt. Dubbed the "ROTC for healthcare," Clasp creates a powerful win-win by enabling employers to invest in future talent while they're still in school, helping repay their student loans in exchange for a multi-year work commitment. This episode is a masterclass in identifying a massive, systemic problem and building an elegant, scalable solution. For any entrepreneur looking to build a mission-driven company, Tess breaks down how to create a category, align incentives for all parties, and turn macro-economic headwinds into powerful tailwinds for growth.
💡 What You'll Take Away For YOUR Business
How to build a “win-win” business model that aligns the incentives of two distinct groups (in this case, employers and students).
Why being sector-specific is a superpower for your go-to-market strategy, creating follower effects and establishing you as an expert.
The strategy for repurposing "wasted dollars" in an industry (like sign-on bonuses with negative ROI) into a powerful, value-driven solution.
How to turn major industry changes and potential threats into massive opportunities that strengthen your company’s position.
Practical ways to embed an AI-first culture in your company, from "AI Champions" to dedicated labs, to boost efficiency and evolve your hiring.
The power of "no" and why turning down the wrong customers and hires, even in the early days, is critical for building a durable business.
📝 About Tess Michaels
Tess Michaels is the Founder and CEO of Clasp, a mission-driven, venture-backed company bridging the gap between education and employment in healthcare. A serial entrepreneur, Tess successfully exited her first company while earning her bachelor's degrees at the Wharton School before getting her MBA at Harvard Business School. Coming from a family of healthcare professionals, Tess combines a deep personal passion for the industry with sharp business acumen to solve one of its most pressing challenges: the critical shortage of clinical talent.
🎯 Tess’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"The biggest learning I've had in building a business is the power of no. Some of the smartest decisions we've made are the ones where saying yes would have been easier, but standing firm and saying no actually got us further."
📢 Memorable Quotes
"Startup years are like dog years. It is so true. Every single year feels like 7 years have gone by. You've lived a lifetime." – Tess Michaels
"You can always think about any change as a headwind. But the reality is how you react to it can really turn it or transform it into a tailwind." – Tess Michaels
"For every $10,000 you put in a sign-on bonus, you get $2,800 worth of value. So it's a negative 72% ROI, yet everyone does it because their peers do it." – Tess Michaels
💡 Actionable Takeaways
✅ Analyze your industry for "wasted dollars" (like inefficient bonuses or high agency fees) and brainstorm how to repurpose that capital into a retention-focused benefit.
✅ Implement a "character check" in your hiring process by having senior candidates interview with junior team members to see how they behave when they think no one is watching.
✅ Define your ideal customer profile beyond just revenue potential. Include values and cultural alignment to protect your brand and ensure you build healthy, long-term partnerships.
✅ Instead of trying to be everything to everyone, dominate a niche. Become an expert in one sector to build credibility, network effects, and a repeatable sales motion.
🔗 Links & Resources
Website: http://www.clasp.com/
Connect with Tess on LinkedIn
Follow Clasp on LinkedIn

Dr. Amanda Young joins the show to share her incredible journey from a PhD in Gerontology to founding MAL Consulting, a firm at the forefront of the booming aging-in-place industry. She breaks down how she turned deep frustration with her corporate role into the catalyst for launching a business that solves a massive societal need. This episode is a masterclass for any wantrepreneur or entrepreneur on how to leverage unique expertise, identify a scalable business model in an overlooked market, and embrace the critical "no margin, no mission" mindset required to build a sustainable and impactful company.
💡 What You'll Take Away For YOUR Business
🚀 How to turn deep industry expertise and a PhD into a highly specialized, in-demand consulting business.
💰 The “no margin, no mission” principle: Why profitability is essential for impact, even if you’re running a mission-driven or nonprofit-focused business.
🧠 Strategies for overcoming imposter syndrome, even when you are a top expert in your field with decades of experience.
📈 How to identify and capitalize on a massive, underserved market need driven by undeniable demographic shifts.
🗣️ The power of using data and case studies to sell a new, disruptive business model to risk-averse leadership and boards.
🔥 How frustration with your current job can be the ultimate fuel for launching your own successful venture.
📝 About Dr. Amanda Young
Dr. Amanda Young is the founder and CEO of MAL Consulting, a firm dedicated to helping nonprofit senior living organizations launch and operate Continuing Care at Home programs. With a PhD in Leadership in Gerontology and two decades of experience in aging services, she is a leading subject matter expert in her field. Dr. Amanda’s unique power comes from her hands-on experience building these programs from the ground up, giving her an unparalleled blend of operational know-how and strategic vision that she now uses to help organizations nationwide expand their mission.
🎯 Amanda’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"You have to understand how much your time and all of your proprietary information that you have in your head, that is worth something."
📢 Memorable Quotes
“If there's no margin, there's no mission. So just because organizations are nonprofit doesn't mean that they're not out there making a profit because they need to.” – Dr. Amanda Young
“I remember the second that I heard that at the board meeting after I got off, I literally filed my LLC that day and said, you know what, I can do this. I'm going to do it myself.” – Dr. Amanda Young
“We don't really ask the consumers themselves, you know, how do you want to be served? And I think that this model allows us to do that.” – Dr. Amanda Young
💡 Actionable Takeaways
✅ Assess Your "Proprietary Information": Take a moment to list the unique knowledge and skills you possess. How can you package this expertise to solve a specific, high-value problem for a niche audience?
✅ Embrace the "No Margin, No Mission" Mindset: Review your current pricing structure. Are you charging enough to not only survive but to thrive and reinvest in your business's growth and mission?
✅ Find Your Catalyst in Frustration: Identify a key frustration in your current job or industry. Instead of seeing it as a negative, use it as fuel to brainstorm a business that provides a better solution.
✅ Arm Yourself with Data: When pitching a new idea or service, especially to a skeptical audience, support your proposal with hard data, compelling case studies, and clear financial benefits.
🔗 Links & Resources
Website: https://www.malconsulting.co/
Connect with Amanda on LinkedIn
Follow MAL Consulting on LinkedIn

In a world of fragmented industries and complex problems, how can one entrepreneur bridge the gaps to create meaningful, systemic change? Robert Espinoza, founder of The CareWorks Project, joins us to share his incredible journey from navigating his parents' long-term care needs to launching a social enterprise that brings together the public, private, and philanthropic sectors. This episode is a masterclass in turning personal experience into a powerful mission and building a vehicle for tangible impact. Robert breaks down why the most effective solutions come from connecting disconnected groups and why “practical action” is the entrepreneur’s greatest superpower. Tune in to learn how to identify opportunities in market failures, leverage cross-sector collaboration for innovation, and find the courage to take the uncomfortable leap that separates wantrepreneurs from world-changers.
💡 What You'll Take Away For YOUR Business
🚀 How to transform a personal pain point into a scalable social enterprise that addresses a major market failure.
🤝 Why breaking down industry silos and bringing together diverse stakeholders (nonprofits, businesses, government) is the ultimate competitive advantage.
🧠 A powerful mindset shift: How to view your nonprofit or for-profit venture as a "social change organization" focused on sustainability and impact.
🤖 The entrepreneur's guide to AI: How to strategically implement technology to increase efficiency and enhance human-centric services, not just replace them.
🗺️ The "work backward" method: A practical framework for mapping out your business strategy by starting with your ultimate goal and building the steps to get there.
⚖️ The perfect balance for taking the leap: How to get comfortable enough to start and uncomfortable enough to truly innovate and succeed.
📝 About Robert Espinoza
Robert Espinoza is the founder and CEO of The CareWorks Project, a social enterprise dedicated to redesigning long-term care, caregiving, and workforce systems. With a rich background that includes roles as CEO of the National Skills Coalition and Executive Vice President of Policy at PHI, he is a nationally recognized strategist who operates at the intersection of the public, private, and philanthropic sectors. Robert’s unique perspective is shaped by both his professional expertise and his personal journey navigating the healthcare system, making him a powerful voice for creating practical, human-centered solutions to society's most complex challenges.
🎯 Robert’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"I needed to be both comfortable enough to take a step forward and uncomfortable enough to push myself to go even further... How comfortable do you have to be to move forward and how uncomfortable do you have to be to actually take the leap? That's the question."
📢 Memorable Quotes
"I think of an entrepreneur as somebody that can exist in any sector... but they're saying, 'Look, the status quo isn't exactly what's working.'... Let me imagine something that rattles the status quo." – Robert Espinoza
"We're all in this kind of mutually reinforcing web, and if you fix one part of it, you fix it for all of us." – Robert Espinoza
"There's nothing more frustrating to me than when I read a policy proposal that is completely out of tune with how a state's law or its systems work... The opposite, impractical, it's just a turnoff." – Robert Espinoza
💡 Actionable Takeaways
✅ Identify the "silos" in your industry. Make a list of stakeholders from different sectors (e.g., nonprofit, corporate, government, academia) who you could connect with to find new opportunities.
✅ Map your next major goal by working backward. Define the ultimate outcome you want to achieve, then outline the specific, practical steps required to get there.
✅ Audit your administrative tasks. Pinpoint 1-2 areas where AI tools could free up your time to focus on high-value, human-centric work like client relationships or strategic partnerships.
✅ Embrace the "uncomfortable leap." Identify one action you've been avoiding because it feels risky or uncertain, and commit to taking that step this week.
🔗 Links & Resources
Website: https://www.careworksproject.co
Substack: https://careactually.substack.com
Connect with Robert on LinkedIn
Follow The CareWorks Project on LinkedIn

Ever find yourself frustrated with how hard things feel in your business, constantly looking for a simpler path or an "easier" strategy? You're not alone. In this Solo Sunday episode, Brian Lofrumento tackles a seductive but dangerous concept that derails countless entrepreneurs: the idea of "easy." Drawing from a candid conversation with a friend, Brian breaks down why chasing what seems easier—whether it's a different target market, a lower price point, or a trendy business model like dropshipping—is a trap. He reveals why no path in business is truly easy and how embracing this reality can become your greatest source of focus and power.
✨ Why This Matters for You
This mindset shift is critical for building a sustainable business:
It frees you from "shiny object syndrome" and the constant temptation to pivot to something that only seems easier on the surface.
It gives you permission to pursue the business you're truly passionate about, even when it's challenging.
It helps you understand that difficulty isn't a sign you're on the wrong path; it's a non-negotiable part of the journey.
It leads to better, more committed decisions because you're no longer operating under the false assumption that an easy option exists.
📝 Key Takeaways
"Easy" Doesn't Exist. Brian argues that we should completely remove the word "easy" from our decision-making framework. Every business model, marketing channel, and target audience comes with its own unique set of difficulties.
The Pricing Fallacy. It’s not inherently easier to sell a $50 product than a $5,000 one. Both require the same foundational work: building know, like, and trust, strong messaging, and a solid sales process.
Every Market is Hard. Selling to enterprise clients involves bureaucracy and long sales cycles. Selling to solo founders involves budget and resource constraints. Neither is "easy," they're just different kinds of hard.
The Uninformed Optimism Trap. New ventures often seem easy because you don't know what you don't know. This "uninformed optimism" is why so many people jump into things they aren't passionate about, only to quit when reality hits.
Choose Your Hard. Since every path will be difficult, you might as well choose the one you genuinely care about. This acceptance is empowering and helps you commit for the long haul.
🚀 Put It Into Action
This week, conduct an "easy trap" audit on your business:
Where are you currently looking for an "easier" way out? Is it a new marketing channel, a different offer, or a whole new business idea?
Be honest: why does it seem easier? Is it because you're in a state of "uninformed optimism" about it? List the potential challenges of this new path that you might be ignoring.
Instead of chasing the illusion of easy, identify one difficult but important task on your current path and recommit to making progress on it this week.
🔗 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 to stop searching for the easy way out and commit to their path

In a world where DoorDash can optimize your burrito delivery to the second, why is it so hard to make data-driven decisions about critical public issues like healthcare and the economy? Shyamsunder Sriram, a data analytics veteran from tech giants like DoorDash and HubSpot, is tackling this massive problem head-on. He joins the show to discuss his new venture, Point Luna, an organization on a mission to centralize the entire world's public data and connect it to AI. This episode is a masterclass in identifying a colossal, overlooked problem and building a scalable, mission-driven tech solution. For any entrepreneur who wants to think bigger, Shyamsunder breaks down why current AI tools like ChatGPT are unreliable for serious analysis, how to build AI that fosters trust, and why democratizing data is one of the biggest opportunities of our time.
💡 What You'll Take Away For YOUR Business
How to Build Trust with AI: Discover why large language models are built for engagement, not accuracy, and how to create AI systems that provide sources and build user confidence.
The Untapped Value in "Dirty Data": Learn how the tedious work of cleaning and organizing scattered data (the "data janitorial work") can unlock immense value and create a powerful business moat.
A Modern Approach to Funding: Hear Shyamsunder’s strategy for using crowdfunding to build a community-backed company and advocate for a mission that serves the public good.
Turning a Societal Problem into a Startup: Get inspired to look for massive opportunities in fragmented systems and learn how to build a business that solves large-scale, meaningful problems.
Leveraging Agentic AI: Understand how to use AI agents to automate the most mind-numbing, repetitive tasks in your business, freeing up human talent for high-level analysis and strategy.
The Power of a Solid Foundation: Why building a clean, interoperable dataset is the critical first step before you can even think about applying sexy AI models or building complex dashboards.
📝 About Shyamsunder Sriram
Shyamsunder Sriram is the founder and CEO of Point Luna, the analytics organization for public good. With a rich background in data analytics at powerhouse tech companies like DoorDash, HubSpot, and Wayfair, Shyamsunder saw a massive disparity between the data capabilities of billion-dollar corporations and the public sector. Driven by a passion to solve ambiguous, large-scale problems, he launched PointLuna to centralize the world’s scattered public data, making it clean, interoperable, and accessible for researchers, students, and organizations working to make the world a better place.
🎯 Shyam's BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"I still think I'm a wantrepreneur. I'm probably going to be a wantrepreneur for the rest of my life, regardless of how successful this is... I want to connect with people who are better than I am in this and kind of work with them."
📢 Memorable Quotes
“If AI is the most powerful tool in human history today, I think it should be used for public good.” – Shyamsunder Sriram
“LLMs are engineered to just drive engagement. They're optimizing for the next answer. They're not optimizing on trust. And this is where PointLuna has a unique opportunity when you connect it to a dataset.” – Shyamsunder Sriram
“We should be fighting like hell to get the data... in a place where it can be connected to AI and it can be used for public good.” – Shyamsunder Sriram
💡 Actionable Takeaways
Audit Your Data Foundation: Before investing in advanced AI tools, evaluate the quality of your own business data. Is it clean, centralized, and easy to analyze? Fix the foundation first.
Build Trust into Your Tech: If you're building a tool that provides information, create a "trust-building step." Show users your sources and how you arrived at an answer.
Identify Fragmentation Opportunities: Look for industries or processes that are inefficient due to scattered information. Building a platform that centralizes and organizes it is a powerful business model.
Explore Mission-Driven Funding: If your startup has a strong social or public good component, consider crowdfunding as a way to not only raise capital but also build a loyal community of advocates.
🔗 Links & Resources
Website: https://pointluna.ai/
Connect with Shyam on LinkedIn
Follow Point Luna on LinkedIn