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0023 - The Hard Truth About Buying Businesses: Cash Flow, Red Tape, and Doing the Work

Business Buying for Financial Independence

Release Date: 11/25/2025

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Business Buying for Financial Independence

In this solo episode, Tim breaks down what buyers should focus on immediately after first learning about buying a business. From casually reviewing listings and building savings, to positioning yourself with brokers and professionals, Tim explains why early exposure and preparation matter far more than rushing into a deal. 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...

info_outline 0032 - Why a $280K Fashion Brand Looked Like a Great Deal… Until It Didn’t show art 0032 - Why a $280K Fashion Brand Looked Like a Great Deal… Until It Didn’t

Business Buying for Financial Independence

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...

info_outline 0031 - ROI Explained: Why Buying a Small Business Beats Stocks, 401(k)s, and Waiting 30 Years show art 0031 - ROI Explained: Why Buying a Small Business Beats Stocks, 401(k)s, and Waiting 30 Years

Business Buying for Financial Independence

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...

info_outline 0030 - How to Build a Business to Sell: Systems, People, and Clean Financials show art 0030 - How to Build a Business to Sell: Systems, People, and Clean Financials

Business Buying for Financial Independence

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...

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Business Buying for Financial Independence

In this episode, Tim breaks down a real-world post about a struggling food business where the seller is trying to recover build-out costs despite little to no profit and a long-term, expensive lease. Tim explains why this situation is a textbook example of the sunk cost fallacy, why buyers often confuse assets with value, and how leases, franchises, and zero cash flow can quietly turn a “deal” into a long-term financial burden. He also discusses the difference between running a healthy business and trying to turn around a failing one—and why most buyers underestimate that gap. Tim...

info_outline 0028 - A 25-Year Employee’s Path to Ownership: Overpaying on Purpose Using None Of His Own Money show art 0028 - A 25-Year Employee’s Path to Ownership: Overpaying on Purpose Using None Of His Own Money

Business Buying for Financial Independence

In this episode, Tim talks with Mike Webster, an operator-turned-owner who spent years working inside a company before eventually buying it himself. Mike shares how his time as an employee shaped his understanding of the business, what he saw behind the scenes that made him consider ownership, and the complicated emotions that come with transitioning from worker to buyer. He also opens up about evaluating whether growth is worth the cost, dealing with burnout, and the mindset shift required to separate personal identity from the business you run. Tim is an entrepreneur who believes everyone...

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Business Buying for Financial Independence

Ian Joseph is the owner and operator of Branch Hospitality Group, a hospitality venture that balances design, experience, and real business fundamentals. In this episode, he shares the journey of stepping into the hospitality industry, learning operations from scratch, and transforming an aging property into a destination that reflects both community and creativity. He talks about the realities of buying an existing motel and restaurant business, and the staffing challenges, margins, customer expectations that came with it. He also talks about the less glamorous side of what it takes to run a...

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Business Buying for Financial Independence

In this episode, Tim talks with Anthony Atiase, husband, father, serial entrepreneur, and co-owner of a janitorial company in South Carolina. Anthony shares how his upbringing across Ethiopia and Ghana shaped his entrepreneurial spirit, why he and his wife pursued business ownership while keeping their day jobs, and how they bought and financed a recession-resistant cleaning company. He also opens up about the search process, negotiating with brokers and sellers, and how creative financing (including investors and seller financing) made the acquisition possible. Tim is an entrepreneur who...

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Business Buying for Financial Independence

  Merchant cash advances (MCAs) are marketed as a quick fix for business owners in need of fast funding — no credit checks, no waiting, and no collateral. But beneath the convenience lies a dangerous financial trap. These advances often come with sky-high effective interest rates and aggressive repayment schedules that can strangle your cash flow. In this episode, Tim breaks down exactly how these offers work, why they’re so tempting, and what smarter, safer alternatives exist for small business owners. Tim Delaney is an entrepreneur who believes everyone should explore the...

info_outline 0024 - Solving Real Problems, Not Chasing Home Runs: Ali Boolani on Business, Failure, and an RV Park Turnaround show art 0024 - Solving Real Problems, Not Chasing Home Runs: Ali Boolani on Business, Failure, and an RV Park Turnaround

Business Buying for Financial Independence

In this episode, Tim talks with Ali Boolani, an entrepreneur and first-generation immigrant whose path from hustling floppy disks in middle school to buying a struggling campground is packed with lessons on persistence, failure, and reinvention. Ali shares how losing his first business forced him to rethink his approach, why listening to customers matters more than chasing the “next big idea,” and how he turned around a mismanaged campground by fixing pricing, modernizing bookings, and focusing on the customer experience. He also opens up about the abundance mindset that guides his...

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More Episodes

In this episode, Tim talks with Jerry Brazie, an entrepreneur and investor who brings a pragmatic, no-nonsense lens to building and buying businesses. Jerry shares why he values fundamentals over hype, how he approaches risk and resilience, and what he’s learned from both successes and setbacks. He also dives into why character matters more than spreadsheets, and the mindset shifts that can carry you through uncertain markets.

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.

[00:00 – 16:45] Fundamentals First

Jerry’s early entrepreneurial journey.
Why discipline beats hype when evaluating opportunities.
Lessons from mistakes that built resilience.

[16:46 – 34:20] Risk, Recessions & Resilience

What Jerry looks for when assessing risk.
Why tough markets are a test of character.
The difference between numbers on paper and reality in practice.

[34:21 – 52:05] People Over Spreadsheets

Why strong operators and relationships matter more than projections.
Stories of deals that worked because of people, not just math.
How to build trust in acquisitions.

[52:06 – End] Lasting Mindset Shifts

Jerry’s takeaways on building businesses that survive downturns.
The importance of clarity, focus, and long-term thinking.
Final advice for first-time buyers navigating uncertainty.

Guest Bio

Jerry Brazie is an entrepreneur and investor known for his straightforward approach to business buying and building. With experience spanning multiple industries, Jerry focuses on fundamentals, resilience, and the people behind the numbers. His perspective challenges listeners to think beyond spreadsheets and pay attention to character and execution.

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 Jerry Brazie:

Connect with Tim and the community on social media for more tips and updates:

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

Tweetable Quotes

“If your entire plan only works in good times, then it’s not really a plan.” – Jerry Brazie
“Numbers matter, but the people behind the numbers matter more.” – Jerry Brazie
“Every market shift exposes who was swimming naked.” – Jerry Brazie