Business Buying for Financial Independence

In this episode, Tim breaks down an important distinction for business buyers: a distressed seller is not the same thing as a distressed business. A seller may simply be burned out, approaching retirement, dealing with changing priorities, or lacking a succession plan, while the underlying business remains profitable and healthy. Tim explains why those situations can create strong acquisition oppo...

Tom Larsen has spent decades building businesses, learning from mistakes, and turning those lessons into a long-running insurance career. In this episode, Tim and Tom walk through how Tom bought his first restaurant in his early twenties, used creative financing and seller notes to get deals done, expanded too quickly into a second restaurant, and ultimately filed for bankruptcy. Tom explains why...

In this solo episode Tim walks through the year leading up to his first business acquisition. He shares what life looked like before buying the store, why his remote job felt like it had a shelf life, how his savings were being depleted, and why he eventually shifted from "this would be nice to do" to "this is what we're going to do."  Tim T. Delaney is an entrepreneur who believes everyone should...

Anthony Lawson built his path from real estate investor to group home operator and debt fund leader by focusing on a niche most buyers overlook: group homes with government-backed contracts and healthcare-related operations. In this episode, Tim and Anthony walk through how Anthony went from buying a six-bedroom single-family home, learning the group home model from scratch, and creating housing f...

In this episode, Chris Larsen discusses why real estate should be viewed like a business, especially when it comes to controlling purchase price, increasing income, understanding net operating income, and using tax advantages strategically. Chris shares how his early experience house hacking a townhouse helped shape the way he thinks about assets, liabilities, and using income-producing property t...

In this episode, Brian Hulet shares why side hustles are not always the cleanest path out of a 9-to-5. He had previously started a private school and community center while still working full-time, but even the part that worked became incredibly time-consuming and was not enough to replace his day job. That experience helped him understand the difference between building from scratch and buying so...

In this episode, Tim goes solo to name the four fears that stop most people from ever buying a business, and gives a reframe and a real mitigation for each one.   It opens on a 2013 phone call. Tim had a business plan he believed in, money saved, and a wine and liquor store he wanted to buy. Then the banker asked what experience he had in the wine and liquor industry. The honest answer was none. T...

In this episode, Tim welcomes Zach Jones to the show to talk about buying businesses through the lens of AI, operator leverage, and creative deal-making. Zach is an Army veteran, husband, father, entrepreneur, and the founder of an AI-native holding company built around acquiring businesses and using AI tools to improve operations, data, workflows, and scale.  Tim is an entrepreneur who believes e...

In this episode, Tim sits down with Kevin Rapport to talk about self-storage acquisition, why self-storage operates like a business and not just a pure real estate play, and how investors can evaluate the opportunity if they want to buy into the space.  Tim is an entrepreneur who believes everyone should explore the opportunities that business and real estate can provide on the path to financial f...

In this episode, Tim sits down with Alan Underwood , a coach, speaker, investor, and entrepreneur, to talk about the seller side of small business transactions. Alan shares the story of building and selling a car dealership, including launching from a former junkyard, surviving a fire before opening, navigating the 2007 credit crunch, and eventually growing the business into a multi-location deale...

In this solo episode, Tim walks through how buying a small wine and liquor store outside Buffalo became the foundation for buying the commercial plaza where that store operated. He explains why he reinvested early profits back into inventory, systems, marketing, and customer loyalty instead of pulling cash out, and how opening a business line of credit before he needed it helped him move quickly w...

In this episode, Tim sits down with Ryan James , a successful business owner, real estate investor, and lifelong entrepreneur, to talk through the messy, real-world process of buying a business. Ryan shares why he shifted from starting businesses to buying an existing one, what he learned from a two-year search, why off-market deals are harder than they sound, and how the right broker can make or...

In this solo episode, Tim explains working capital as current assets minus current liabilities, including cash, accounts receivable, inventory, vendor bills, credit card bills, and other short-term obligations. He also shares why running out of working capital can quickly put a buyer in trouble after closing, especially if vendors need to be paid before customers have paid the business.  Tim also...

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,...