1335: He Mortgaged His House 3 Times to Build His Business! Here’s Why w/ David Frederiksen

In this powerhouse episode, Brian sits down with David Frederiksen, a seasoned CEO who has lived through the entrepreneurial gauntlet and emerged with a playbook for massive growth. David shares the raw, unfiltered story of scaling his healthcare company to over $250 million in receivables, including mortgaging his house three times and raising $16 million from angel investors (a move he surprisingly advises against). This isn't just theory; it's a masterclass in the realities of scaling, packed with hard-won lessons on fundraising, execution, and team alignment. If you're tired of hearing the word "scale" as a buzzword and want to understand the strategic decisions that truly drive growth, this episode will give you the clarity and conviction to build a business—and a life—you love.

💡 What You'll Take Away For YOUR Business

• 🍕 The "Two Pizza Rule": A simple yet profound way to know exactly when you need to change your systems, communication, and processes as you grow.
• 💰 Fundraising Red Flags: Why raising $16M from angel investors can be a strategic mistake and when you should pull the trigger on institutional capital instead.
• 🚀 Need vs. Demand: Learn the critical difference between a market that needs your product and one that is willing to pay for it—a lesson David learned from a multi-billion dollar business venture.
• 🔥 How to Execute a 90-Day Sprint: A step-by-step guide to breaking down your biggest goals into granular, actionable tasks that guarantee progress every single quarter.
• 🛠️ The Coach, Build, Transfer Model: Discover a unique methodology for getting expert help to build scalable systems and then seamlessly transferring ownership back to your team.
• 🤯 The Entrepreneur's Mindset: Why you must believe in your vision "like gravity" and drive full-speed towards the cliff, trusting that your car will either fly or land safely.
• ⚖️ The Speed, Cost, & Quality Triangle: Understand the trade-offs you're making in execution and how to consciously choose which two you will prioritize to achieve your goals.

📝 About David Frederiksen 

David Frederiksen is a seasoned CEO, entrepreneur, and executive coach with over 25 years of experience scaling businesses in healthcare, finance, and technology. He is the founder of Tobias Advisors, where he helps leadership teams execute with clarity and grow smarter. As a former CEO, David built and exited a healthcare company after raising $16 million and scaling it to over $250 million in receivables. His unique, hands-on experience gives him a rare perspective on what it truly takes to navigate the chaos of growth and build not just a scalable company, but a sustainable life.

🎯 David’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs 

"It's really, really important to distinguish the difference between need and demand... Demand is taking that same need, but there are customers willing to take out their wallets and pay. Those are fundamentally different things."

📢 Memorable Quotes

• "Entrepreneurs... they drive full speed towards the edge of the cliff with every ounce of conviction that either the car is going to fly or there will be something to drive on." – David Frederiksen
• "Every time your team grows to the point where you need two more pizzas to feed your team, you've got to do things differently. You've got to communicate differently, you've got to solve problems differently." – David Frederiksen

🔗 Links & Resources

• Visit Tobias Advisors’ website
• Connect with David on LinkedIn
• Follow Tobias Advisors LLC on LinkedIn