How I Built a Business That Gave Me Time & Financial Freedom - Tyler Jorgenson

Entrepreneurship is supposed to bring freedom—but too often, it does the opposite. In this episode, I dive into how I built a business that let me live on my terms. From learning to sail to getting my MBA and being fully present with my kids, I structured my company differently. I share the biggest mistake I made (not scaling fast enough) and the real reason most entrepreneurs get stuck. Plus, I break down the systems, mindset shifts, and strategies that helped me avoid the self-employed trap and truly own a business—not just a job. Key Takeaways Most entrepreneurs just trade a 9-to-5 for a 24/7 grind. Freedom requires intentional business design. Think like a business owner from day one. Structure your company to function without you. Premium customers = fewer headaches. Stop competing on price and attract buyers who value quality. Systemize everything. Email-based customer support, automated responses, and predefined contacts reduce friction. Don't wait to scale. If your offer is working, double down—before someone else does. Know your numbers. Customer acquisition cost (CAC) vs. lifetime value (LTV) can make or break you. An abundance mindset wins. Collaboration is more powerful than competition. Chapters 00:02 – The freedom trap: Why entrepreneurs stay stuck 01:28 – How I built a business that worked for me 02:51 – The cashflow quadrant: From self-employed to business owner 03:42 – Designing a business for lifestyle freedom 05:51 – Why I set up my business to look bigger than it was 08:21 – The cha-ching moment: Celebrating wins with my family 10:38 – My biggest mistake: Not scaling fast enough 12:55 – Understanding CAC vs. LTV: Why I left money on the table 14:58 – The power of mentorship and networking 16:02 – What's next: The biggest lessons I learned the hard way ----- Disclaimer: The information provided in this episode is for educational and informational purposes only. It should not be considered as financial advice or a recommendation to buy or sell any financial instrument or engage in any financial activity. The content presented here is based on the speaker's personal opinions and research, which may not always be accurate or up-to-date. Financial markets and investments carry inherent risks, and individuals should conduct their own research and seek professional advice before making any financial decisions.