Business Buying for Financial Independence

In this episode, Tim talks with Aubrey Fitzloff about how she went from a temp-to-hire administrative role at an insurance agency to becoming the owner of that same business. Aubrey shares how the original owner transitioned responsibilities to her over time, why the deal was built on trust and seller financing, and how she later used an SBA loan to make a balloon payment and buy out the remaining...

In this episode, Tim talks with Alex Pardo about why self-storage can be a powerful business to buy, how he moved from corporate America into real estate, and why he eventually shifted into self-storage investing. Alex shares how he became "unemployable" after his first real estate deal, why a $51,000 loss became one of the best lessons of his career, and how paying for coaches, mentors, and the r...

In this solo episode, Tim breaks down why most buyers stall before closing. It's usually not because of deal flow, financing, or timing. More often, the real issue is internal: the buyer hasn't fully made the decision yet. Tim shares three reasons buyers tend to hesitate, including waiting to "feel ready," trying to eliminate risk, and failing to make the identity shift from someone exploring busi...

In this episode, Tim talks with Mike Wilson about how he went from a childhood shaped by financial instability, into the Air Force, then into law enforcement, and eventually into business ownership. Mike shares how he bought Blue Mint Thai using equity from his rental properties and a 0% owner-financed note, why he originally expected the restaurant to be a hands-off investment, and how the busine...

In this episode, Tim T. Delaney sits down with Elvon Bowman to unpack how a military servicemember with no deep operating background in self-storage went from studying deals to buying a facility in Florida. Elvon shares how he and his wife first looked at multifamily, why he pivoted into self-storage, what he learned from walking away from an earlier deal, and how repeated analysis built the confi...

In this solo episode, Tim explains why buyers who focus only on price, terms, and financials often miss what actually drives a seller's decision. Using two personal examples: a pet store deal he did not close and the wine and liquor store he ultimately bought, Tim shows how seller motivations can include legacy, community relationships, customers, employees, vendors, and personal fit just as much...

In this repeat-guest episode, Tim welcomes Jimmy Feeman back to the show after Jimmy successfully closed on a subcontracting business in Montana. They dig into what actually happened between "I want to buy a business" and "I finally bought one". The conversation also explores how Jimmy evaluated the deal, why he brought in a partner, what he is changing first, and why persistence matters more than...

Tim talks with Jeremy Hans about the messy reality behind buying, operating, and exiting a business. Jeremy shares how he went from Navy helicopter pilot to real estate investor to business owner, how a botched acquisition process still led to a successful deal, what he learned from scaling Velocity from a small team into a much larger operation, and why his current search for the next business ha...

In this solo episode, Tim provides a comprehensive guide to writing effective Letters of Intent (LOIs) for business acquisitions. Tim T. Delaney breaks down the key components, common mistakes, and strategic tips to help buyers structure LOIs that save time, reduce risks, and facilitate smoother deals. Tim T. Delaney is an entrepreneur who believes everyone should explore the opportunities that bu...

In this solo episode, Tim introduces the BUYBOX framework, a six-part method for getting more specific about what kind of business you actually want to buy. He argues that many buyers stay stuck because they search too broadly, get excited about random deals, and never take the time to define their desired outcome, constraints, role, budget, no-go industries, and search criteria. The more clearly...

In this solo episode, Tim breaks down when buying a second business can accelerate growth faster than building everything organically. He explains how acquisitions can increase revenue, add staff, bring in technology or equipment, reduce competition, and create economies of scale, while also warning about integration problems, cultural mismatch, and distractions that can hurt the core business if...

Tim talks with  Bethany LaFlam , a securities and business attorney, real estate investor, and entrepreneur whose work sits at the intersection of capital raising, acquisitions, burnout prevention, and intentional wealth-building. They also get into her framework of "Other People's Everything," raising money the right way, structuring friends-and-family capital carefully, buying a hotel in Belize,...

In this solo episode, Tim takes on a debate he constantly sees online: is a W-2 job at a large corporation or government role really more secure than owning an established small business? He breaks down why "business failure" statistics can be misleading, why established businesses are different from fragile startups, how layoffs and hiring slowdowns weaken the usual case for job security, and why...

In this episode, Tim talks with Sarah Bratcher , a CPA, real estate investor, and founder of REI Accounting Solutions, about buying a laundromat after years in real estate and finance. The conversation also expands into the difference between building a business from scratch versus buying an established one, how Sarah is thinking about acquiring a bookkeeping firm next, and why knowing your number...

In this episode, Tim talks with Tijera Wright, founder of Board and Bougee, about what it actually looks like to go from being interested in buying a business to owning one. Tijera brings the perspective of an entrepreneur who already built her own business from scratch. The conversation stays beginner-friendly while still getting into the real mechanics behind buying a small business.  Tim is an...

In this solo episode, Tim breaks down the real pros and cons of working with business brokers from both the buyer and seller side. He explains why brokers are often unavoidable in small business acquisitions, where their incentives can create friction, how they can still add real value in valuation, privacy, deal flow, and negotiation.  Tim Delaney is an entrepreneur who believes everyone should e...

In this episode, Tim sits down with James Smith , a cabinetry-and-design business owner who bought his way into an established operation instead of starting from scratch. James breaks down what the transition actually felt like after closing—learning the real workload behind the "owner isn't super involved" story, building relationships fast, and navigating the practical risks that show up when yo...

Tim breaks down a real NEMT (non-emergency medical transportation) listing and shows how to pressure-test the "recurring revenue" claim without getting hypnotized by the headline numbers. He walks through who pays, what operational load really looks like at scale (vehicles + staff), and the unsexy checks that decide whether this business fits your life... or eats it. Tim Delaney is an entrepreneur...

Buying a business isn't just about "finding a deal." It's about building the structure that lets you grow without burning out time, partnerships, and the financial plan underneath the whole thing. In this episode, Tim talks with Daniel Schlein about what changes when you shift from "doing everything yourself" to building a real operating machine; and how smart partnerships + smart planning can kee...

In this episode, Tim talks with Ashley Coates , a real estate investor, broker, and operator who has built multiple businesses across real estate, restaurants, and residential care. Ashley shares how she started in real estate at a young age, lessons from buying and operating different businesses, and how she turns properties into scalable residential care facilities with systems and leadership in...

In this solo episode, Tim breaks down the industries buyers keep asking about for 2026; and why the industry itself matters far less than fit, fundamentals, and execution. He walks through healthcare-adjacent services, in-person service businesses, experience-driven companies, B2B opportunities, and niche manufacturing, while cautioning against chasing trends or buying something you'll hate operat...

Starting a business from scratch sounds exciting until you experience the steep learning curve, operational headaches, and financial uncertainty that come with it. In this episode, Tim sits down with  Joe Trotto to talk about the realities of launching versus buying a business, why Joe pivoted toward acquisition, and what he learned while pursuing a deal in the marine tourism space. From evaluatin...

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 opp...

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 e...

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,...