In this episode, Tim talks with Milan Nolen, an entrepreneur and business buyer who shares a transparent look at evaluating risk, recognizing red flags, and knowing when not to do a deal. Milan walks through her transition from employee to founder mindset, the early mistakes she made by moving too quickly, and the moments that forced her to slow down and reassess what she was really buying.

She explains how ignoring basic math and operational realities nearly pulled her into a bad acquisition, why non-operating businesses carry hidden danger, and how learning to walk away became one of the most valuable skills she developed as a buyer.

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.

Milan describes the mindset shift required to move from employee thinking to ownership, and why she didn't fully grasp that transition until she was already deep into the process.

How moving too fast, skipping the numbers, and relying on optimism created blind spots that could have led to a costly mistake.

Milan breaks down the moment she realized the deal might be a "dumpster fire," and how recognizing operational and structural issues changed her approach.

Why buying a business that isn't actively operating introduces a completely different risk profile — and why that realization became a turning point.

The emotional and strategic challenge of stepping back from a deal, even when the desire to buy is strong.

Milan's key takeaways for buyers evaluating their first acquisition, including patience, discipline, and respecting what the numbers are telling you.

Milan Nolen is an entrepreneur and business buyer who focuses on disciplined deal evaluation, risk awareness, and long-term sustainability. Through her experience navigating potential acquisitions, she emphasizes the importance of math, operational clarity, and the confidence to walk away from deals that don't make sense.

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: @milanterez
TikTok: @milanterez
Website: milantereznolen.com

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"Either this is a complete dumpster fire, or there's a deeper reason here." – Milan

"I still want to buy a business — I just don't think this is the one to do it with." – Milan

Return on investment (ROI) is often treated like a simple spreadsheet calculation — but in small business acquisitions, it's much more than just a number. In this episode, Tim breaks down the real difference between ROI and cash-on-cash return, how leverage changes outcomes, and why focusing only on percentages can lead buyers to make bad decisions. Using practical examples, Tim explains how time, effort, risk, and financing all factor into evaluating whether a deal is actually worth pursuing.

Tim Delaney 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.

[00:00 – 02:30] ROI Is More Than a Spreadsheet

Tim explains why ROI shouldn't be viewed as just a financial formula, but as a broader measure of freedom, risk, and opportunity cost.

[02:31 – 06:15] What ROI Really Measures

Breaking down how ROI is calculated, what it includes, and why purchase price matters more than most buyers realize.

[06:16 – 12:45] Cash-on-Cash Return Explained

How cash-on-cash return works, why leverage dramatically changes outcomes, and how financing can increase early returns.

[12:46 – 18:30] Leveraged vs. Unleveraged Returns

Comparing all-cash purchases to financed deals and explaining why cash-on-cash returns are often much lower in pure cash acquisitions.

[18:31 – 26:40] Real-World Business Example

Walking through how owner pay, debt paydown, and equity growth affect actual cash coming back to the buyer.

[26:41 – 34:50] Comparing ROI Across Investments

How small business returns stack up against stocks, bonds, and real estate — and why business ownership should demand higher returns.

[34:51 – 42:30] Time, Effort, and Risk

Why there is no universal "good" ROI number, and how stability, workload, and industry risk should shape return expectaions.

[42:31 – End (~45:00)] Final Thoughts

Why ROI is only one part of the decision-making process and how buyers can avoid chasing.

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.

Connect with Tim and the community:
Website: https://www.powerofbiz.com
YouTube: https://www.youtube.com/@powerofbiz
Instagram: @timtdelaney
Threads: https://www.threads.com/@timtdelaney
LinkedIn: linkedin.com/in/timothytdelaney
Facebook: facebook.com/timtdelaney

Tweetable Quotes:

"ROI isn't just a spreadsheet formula — it's also a freedom calculation." – Tim Delaney

"Cash flow and profit are not the same thing, especially when debt is involved." – Tim Delaney

"There is no single ROI number that works for every business or every buyer." – Tim Delaney

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
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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