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