In this episode, Tim talks with Tiffany Kao, an entrepreneur and creator who shares a candid look at what it really takes to bet on yourself, and the mistakes that come with it. Tiffany opens up about quitting her job early in her journey, the pressure to "burn the boats," and how that decision forced her to learn hard lessons about sustainability, timing, and resilience. She reflects on how her definition of success has evolved, why confidence without preparation can be dangerous, and how experience reshaped the way she approaches risk, growth, and long-term stability.

Tim is an entrepreneur who believes everyone should explore the opportunities that business and real estate can provide on the path to financial freedom. He owns and operates a wine & liquor store, a software startup, a consulting company, and a growing portfolio of commercial and residential real estate.

Tim's passion for independent business has led him to support dozens of other business owners. For over a decade, he has worked with businesses on strategy, processes, finances, and marketing. These experiences, along with analyzing dozens of other businesses for potential acquisition, have provided Tim with an immense knowledge base to pull from.

Tim has appeared on multiple top-tier podcasts in the financial space, such as Bigger Pockets Money and The Freedom Chasers Podcast.

Tiffany shares why she quit her job early, the mindset behind "burning the boats," and why she now believes timing and preparation matter just as much as courage.

The realities of entrepreneurship after leaving a steady paycheck, early missteps, and how pressure can accelerate growth — or expose cracks fast.

Why believing in yourself isn't always enough, how overconfidence can backfire, and the systems Tiffany wishes she had built sooner.

How Tiffany's view of freedom, income, and sustainability evolved as she gained experience — and why stability matters more than proving a point.

Tiffany's advice for anyone considering quitting too early, what she'd do differently now, and how to approach risk with clearer eyes.

Tiffany Kao is an entrepreneur and creator who shares honest insights about the realities of self-employment, risk-taking, and personal growth. Through her experiences leaving traditional work and navigating entrepreneurship, she emphasizes thoughtful decision-making, resilience, and redefining success on your own terms.

If you found value in today's show, make sure to subscribe so you never miss an episode packed with insights to help you buy and grow a business that creates real financial freedom.

Instagram: https://www.instagram.com/tiffany_on_the_go_/

Website: https://www.powerofbiz.com
YouTube: https://www.youtube.com/@powerofbiz
Instagram: https://www.instagram.com/timtdelaney/
Threads: https://www.threads.com/@timtdelaney
LinkedIn: https://www.linkedin.com/in/timothytdelaney/
Facebook: https://www.facebook.com/timtdelaney

"I promptly quit my job — which, by the way, is highly not recommended — but I was young and strong-headed, and somebody had given me the speech about how you need to burn your boats." – Tiffany Kao

"Confidence without preparation can put you in a really tough spot." – Tiffany Kao

"Looking back, I would've timed my leap very differently." – Tiffany Kao