0028 - A 25-Year Employee’s Path to Ownership: Overpaying on Purpose Using None Of His Own Money
Business Buying for Financial Independence
Release Date: 12/30/2025
0033 - Want to Buy a Business? START Here!
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...
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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...
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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...
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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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0029 - Valuing a Business With High Buildout Cost and No Profit
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...
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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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0027 - Scaling Through Small Town Hospitality, Revitalization & Development
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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0026 - Buying a Business With No Industry Knowledge
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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0025 - The Tough Reality of Merchant Cash Advances
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...
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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...
info_outlineIn 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 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 – 12:30] The Growth Dilemma & Becoming a Key Operator
Mike explains the contradiction of growing the business even though it would raise the price he’d eventually have to pay for it, and how he became the de facto operator running the company day to day.
[12:31 – 25:00] Early Career, Sales, and Learning the Business
Mike shares how he got into the industry, his early sales experience, the mentors who pushed him forward, and how he learned the operational side from the inside.
[25:01 – 38:00] Friction With the Owner & Stepping Into Leadership
How responsibilities shifted as the business grew, the strain of carrying more weight without ownership benefits, and the point where Mike realized he needed to make a move.
[38:01 – 52:00] Preparing for a Buyout & Understanding Real Valuation
Mike breaks down the moment he recognized he was effectively running the business, how he evaluated its value, and the internal debate over whether growth was worth it.
[52:01 – End] Burnout, Identity, and Deciding What Comes Next
What Mike learned about separating himself emotionally from the business, avoiding burnout, and how he approached the decision of whether to buy the company he helped run.
Guest Bio
Mike Webster is an experienced operator who deeply understands the challenges of running and scaling a business from the inside. After years of managing day-to-day operations, he began evaluating whether purchasing the company he worked for made strategic and personal sense. His journey highlights the realities of growth, burnout, valuation, and the mindset shifts required when transitioning from employee to prospective owner.
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.
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Website: https://www.powerofbiz.com
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Tweetable Quotes:
“Am I really going to grow something… just so I can pay more for it?” – Mike Webster
“You can’t let the business define who you are — that’s when everything starts feeling heavier than it should.” – Mike Webster
“Sometimes the best decision isn’t scaling — it’s stepping back to understand what you actually want.” – Mike Webster