Libsyn Directory

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

Business Buying for Financial Independence

Release Date: 12/02/2025

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

More Episodes

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 acquisitions today.

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] Ali’s Unusual Background
Ali shares his journey as an academic and entrepreneur.
From laundromats to salons to tech companies — finding mismanaged opportunities.

[12:31 – 23:59] Lessons from Failure
Why his first ventures didn’t work out.
The importance of talking to customers before scaling ideas.

[24:00 – 39:47] The Campground Opportunity
Discovering a poorly run RV park in New York State.
Issues with outdated operations: missed calls, bad website, mispriced cabins.
Why Ali saw it as the perfect acquisition.

[39:48 – 53:21] Turning Things Around
Implementing modern booking systems, fixing pricing, adding amenities.
Examples of occupancy improving once small changes were made.

[53:22 – End] Abundance Mindset & Takeaways
Ali explains how abundance mindset drives his acquisitions.
Tim reflects on the importance of building partnerships and long-term wins.

Guest Bio
Ali Boolani is a first-generation immigrant, entrepreneur, and small business acquirer. From hustling as a teen in subsidized housing to buying and turning around a struggling campground, Ali’s journey highlights the grit, lessons, and mindset needed to succeed in business buying. He’s passionate about solving real operational problems and building businesses that create lasting impact.

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