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In this episode, Tim challenges the assumption that staying in the same job, career, or situation is automatically safer than making a change. He shares examples of experienced professionals who were laid off despite years of loyalty and strong performance, then struggled to find comparable work afterward. The goal is not to argue that everyone should immediately quit their job. It is to recognize that standing still has a cost too. Whether it is a job, a city, a career path, or another commitment that no longer makes sense, Tim encourages listeners to evaluate the risks of staying with the same seriousness they would evaluate the risks of moving forward.  Tim T. 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 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 – 01:10] The Hidden Risk of Staying Put [01:10 – 02:13] Why We Analyze Change but Ignore Staying Still [02:13 – 03:41] Risk #1: Layoffs and False Job Security [03:41 – 05:34] Risk #2: Your Job Can Change Without You [05:34 – 06:59] Risk #3: The Time You Can't Get Back [06:59 – 08:14] Risk #4: Getting Trapped by Your Career Identity [08:14 – 08:55] Standing Still Has a Price Too [08:55 – 09:22] What Are You Calling "Safe"?   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 Tim and the community: Website:     https://www.powerofbiz.com YouTube:    https://www.youtube.com/@powerofbiz Instagram:   @timtdelaney Threads:      https://www.threads.com/@timtdelaney LinkedIn:      linkedin.com/in/timothytdelaney Facebook:    facebook.com/timtdelaney   Tweetable Quotes: "The company doesn't owe you anything beyond what they've already paid you."  — Tim T. Delaney "That time you're giving to your current situation, you're never able to get back."   — Tim T. Delaney "Standing still and staying put has a price as well."  — Tim T. Delaney

Daniella Devine went from working inside her family's third-generation flooring company to leaving the business, building a career in commercial real estate, and ultimately returning to buy the company from her father. In this episode, Tim and Daniella unpack what that acquisition actually looked like behind the scenes, including the emotional side of buying from a longtime owner, negotiating with family, inheriting relationships that did not always survive the transition, and discovering that a decades-old business still needed to be rebuilt operationally.  Tim T. 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 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 – 02:44] Daniella Devine and Buying a "Heart Asset" [02:44 – 08:26] Buying the Third-Generation Family Business [08:26 – 15:24] From Flooring Retail to Commercial Contracts [15:24 – 21:40] Family Succession and the Emotional Side of Selling [21:40 – 28:08] Seller Trust, Financing, and Understanding the Owner [28:08 – 36:20] Leaving the Family Business and Finding Her Way Back [36:20 – 46:20] Relationships, Working Capital, and Acquisition Mistakes [46:20 – 51:56] Expensive Debt, the Failed SBA Takeout, and the Turnaround [51:56 – 59:20] Masterminds, Strategic Planning, and Using AI in Operations [59:20 – 01:04:20] Pairing Business Income With Commercial Real Estate Guest Bio Daniella Devine is an entrepreneur and operational strategist who serves as president and CEO of her family's commercial flooring company. After years working inside the third-generation business, Daniella moved into commercial real estate before eventually returning to acquire the company from her father.    Connect with Daniella: Instagram:        instagram.com/thedanielladevine/  Website:           thedanielladevine.com    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 "This is not a hard asset. It's a heart asset." — Daniella Devine  "Buy slow, operate fast." — Daniella Devine  "When both people are uncomfortable and close, it's a good deal because both had to compromise." — Daniella Devine

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 opportunities when the buyer focuses on a fair, ethical, win-win transition rather than trying to exploit the seller's circumstances. He also shares examples from his own liquor store acquisition and discusses how seller motivation can influence price, terms, and transition timelines. Tim T. 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 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 – Distressed Seller vs. Distressed Business 00:36 – What Makes a Seller Distressed? 01:40 – What Makes a Business Distressed? 02:10 – Why the Difference Matters 04:00 – Finding an Ethical Win-Win Deal 05:11 – Understanding the Seller's Motivation 05:47 – Burnout, Retirement, and Succession Planning 07:26 – Signs of a Distressed Business 08:40 – Gross Profit and Increasing Debt 10:22 – Why Distressed Businesses Are Risky for First-Time Buyers 11:39 – Ethical Acquisitions and the Ripple Effect 12:39 – The Best Type of Distressed Deal   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 Tim and the community: Website: https://www.powerofbiz.com YouTube: https://www.youtube.com/@powerofbiz Instagram: @timtdelaney Threads: https://www.threads.com/@timtdelaney LinkedIn: linkedin.com/in/timothytdelaney Facebook: facebook.com/timtdelaney   Tweetable Quotes: "Distressed sellers are not the same as distressed businesses."  — Tim T. Delaney "There are millions of small business owners out there that have no idea what they're going to do with their business when they're ready to retire."   — Tim T. Delaney "Distressed sellers with healthy businesses create the best win-win deals." — Tim T. Delaney

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 the first business worked while the second struggled from the start, how bankruptcy reshaped the way he thinks about credit and risk, and how he later rebuilt his career by betting on himself, developing a niche, and building relationships without relying on pushy sales tactics. Tim T. 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 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 – 01:17] Tom Larsen's Business Story and the Cost of Starting From Scratch [01:17 – 07:42] Buying a Building, Seller Financing, and Starting an Insurance Agency [07:42 – 17:44] Buying a Duplex and a Restaurant in His Early Twenties [17:44 – 22:25] The Second Restaurant, Bankruptcy, and Rebuilding Credit [22:25 – 29:20] Lessons From Failure and Returning to the Insurance Business [29:20 – 35:21] Commission-Only Sales, Multiple Income Streams, and Starting Over [35:21 – 43:42] Entrepreneur Groups, Masterminds, and Lifelong Learning [43:42 – 50:21] Cyber Coverage, Workers' Comp, Umbrella Policies, and Insurance Due Diligence [50:21 – 56:44] Helping Instead of Selling and Staying Top of Mind Guest Bio Tom Larsen is the owner of Larsen Insurance Agency and has worked in the insurance industry for more than three decades. Before starting his own agency, Tom owned restaurants and invested in real estate, experiences that gave him firsthand lessons in entrepreneurship, financing, risk, bankruptcy, and rebuilding. Today, he continues to operate his insurance agency, participate in entrepreneur and real estate communities, and share practical advice drawn from decades of business experience.    Connect with Tom:   Instagram:        instagram.com/the_insurance716/ Facebook:         facebook.com/tom.larsen.9066/ LinkedIn:           linkedin.com/in/larseninsurance/   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 "You never know until you ask." — Tom Larsen  "I believe learning never ends." — Tom Larsen  "When you're truthful with people, it ends up coming back to you." — Tom Larsen

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 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 – The Year Before the Deal 01:10 – Life Before Buying the Store 02:37 – Rethinking Business Ownership 03:21 – The Job Had a Shelf Life 04:24 – Savings and the Ticking Clock 05:48 – Searching for a Business 07:26 – Getting Ready to Be Ready 09:15 – The Liquor Store Opportunity 10:28 – Setting a Deadline 12:00 – Accountability and Taking Action    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 Tim and the community: Website: https://www.powerofbiz.com YouTube: https://www.youtube.com/@powerofbiz Instagram: @timtdelaney Threads: https://www.threads.com/@timtdelaney LinkedIn: linkedin.com/in/timothytdelaney Facebook: facebook.com/timtdelaney   Tweetable Quotes: "We weren't necessarily ready to buy the wine and liquor store, but we were ready to be ready."  — Tim T. Delaney "There was a real ticking time bomb that I needed to pull the trigger on before we had not enough money to do this."  — Tim T, Delaney "Make sure you set some goals, some accountability, and some deadlines for yourself."  - Tim Delaney

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 for veterans, to acquiring existing facilities with staff, licenses, contracts, and real estate already in place.  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 – 01:49] Anthony Lawson and the Debt Fund Mission [01:49 – 06:07] Turning a First Property Into Veteran Housing [06:07 – 09:24] OpCo/PropCo and Operating Group Homes [09:24 – 17:50] Creative Scaling, Seller Calls, and Rental Arbitrage [17:50 – 23:00] Seller Financing and Partnership Structure [23:00 – 29:07] Halfway Houses, Nonprofits, and Buying Existing Facilities [29:07 – 45:08] The First Existing Group Home Acquisition [45:08 – 52:23] Systems, Speed, and Building the Debt Fund [52:23 – 01:05:00] Debt vs. Equity, Investor Protection, and Final Advice Guest Bio Anthony Lawson is a seasoned real estate investor with more than 10 years of experience and a former United States Army veteran. He leads a debt fund focused on delivering fixed returns to investors by acquiring group homes with government contracts and healthcare businesses.    Connect with Anthony:   Instagram:     instagram.com/anthony_theinvestor/ Facebook:     facebook.com/anthony.lawson.90829 Website:       www.globalinvestmentcapitalgroup.com LinkedIn:       linkedin.com/in/anthony-lawson-a2b924163 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 you feel like you don't know enough, it's okay."  — Anthony Lawson "When you buy something long distance, it forces you to create a system."  — Anthony Lawson "If you're using other people's money, make sure you're talking to the right professionals."  — Anthony Lawson

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 to create more freedom.  The conversation also covers Chris's "family bank" strategy, where cash value life insurance policies created liquidity that could be used to fund a car wash down payment. Chris explains how the policy loan gave him access to hundreds of thousands of dollars within 24 hours, and how the car wash then paid that loan back with interest and profit.  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 – 01:49] Using a Family Bank to Buy a Car Wash [01:49 – 06:47] Chris's Background and Real Estate Mindset [06:47 – 12:16] House Hacking, Assets, and Financial Independence [12:16 – 18:15] Buying Car Washes and Evaluating Deals [18:15 – 24:40] Underwriting, AI, and Discounted Opportunities [24:40 – 29:47] Car Washes, Equipment, and Tax Advantages [29:47 – 34:07] Business Ownership, Real Estate, and Tax Strategy [34:07 – 37:19] Policy Loans, Liquidity, and the Family Bank [37:19 – 44:45] Entity Structure, Roll-Ups, and Thinking Bigger Guest Bio Chris Larsen is the founder and principal of Next Level Income. He has been investing in and managing real estate for more than 20 years, beginning with his first rental property at age 21. Since then, Chris has expanded into development, private lending, distressed debt, commercial offices, commercial real estate syndications, and active business ownership.    Connect with Chris:   YouTube:      @thenextlevelincomeshow Website:        www.nextlevelincome.com Book :            NextLevelIncome.com/financialfreedombook  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 "Seek to own assets and rent liabilities."   — Chris Larsen "Get really clear on what you want before you start looking at deals."   — Chris Larsen "If you don't have the strength to operate the business, partner with somebody who does."   — Chris Larsen

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 something that already has customers, employees, and momentum.  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 – 03:40] Brian's Background and Why He Wanted to Buy [03:40 – 08:59] Side Hustle Lessons and the Cost of Starting From Scratch [08:59 – 14:20] M&A Experience, Coaching, and Making the First Calls [14:20 – 22:43] Hiring a Coach and Getting Comfortable Spending Money [22:43 – 33:57] Choosing the Sporting Goods Store and Building Seller Trust [33:57 – 41:35] SBA Financing, HELOC, and Finding the Cash [41:35 – 47:20] First Six Months and Inventory Challenges [47:20 – 55:50] Retail Lessons, Store Focus, and Gradual Improvements [55:50 – 59:48] Giving Back and Supporting Local Businesses    Guest Bio Brian Hulet is a father, volunteer, and the owner of Sports Exchange in Mesa, Arizona. After a 20-year career in health care administration, Brian bought the business and now focuses on local community partnerships and making sports equipment more accessible.    Connect with Brian:   LinkedIn:         linkedin.com/in/brian-hulet  Website:          SportsXchangeAZ.com    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 "Everybody who has ever bought a business had to ask somebody for the first time."  — Brian Hulet "If you are trying to replace your 9-to-5, a side hustle can be a long, slow path." — Brian Hulet "Buying a business is all about building a relationship."  — Brian Hulet

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. The deal got funded anyway, and that store has since paid for a plaza and a portfolio of apartments.   The four fears are looking stupid, losing the money, feeling trapped, and failing where everyone can see it. All four are legitimate. None of them is a reason. Tim walks through what actually shrinks each one, including the deal structures that make the money question smaller than people think, the industry-job test almost nobody runs before they buy, and the reason buying an established business is the risk mitigation rather than the risk.   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 – 01:11] "What Experience Do You Have?" I Said None [01:11 – 02:19] Fear #1: The Fear of Looking Stupid [02:19 – 03:09] Peace Corps to Ethiopia: Where Self-Belief Actually Comes From [03:09 – 05:20] The Rooms That Made Buying a Business Feel Normal [05:20 – 07:35] Fear #2: Losing the Money, and the Math on 10% Down [07:35 – 09:01] The Risk of Staying Put Is a Number Nobody Writes Down [09:01 – 11:08] Fear #3: Feeling Trapped, and the Test Almost Nobody Runs [11:08 – 13:22] Fear #4: Failing Where Everyone Can See It [13:22 – 14:46] Why the Right Room Beats Willpower [14:46 – 15:50] Stop Asking "Can I?" and Start Asking "How Can I?"   Key Takeaways   The fear of looking stupid has no shortcut. You feel it, you do the thing anyway, and it shrinks with reps. Analyzing more businesses is the rep that makes seller and banker conversations easier. Price is one term out of many. Seller financing, SBA guarantees, a working capital cushion and escrow holdbacks are what decide whether a slow quarter is a problem or an emergency. Buyers who lose everything almost always skipped the structure. Standing still is a position and it has risk. If you get laid off next quarter, the down payment you were protecting becomes six months of living expenses instead. You are not stuck. You bought it, you can sell it. Inside year one it probably costs you money. Two or three years in, you have paid down debt and you likely clear a profit. Test the industry before you own it. Take a job in it, or adjacent to it, even at a small pay cut. Six months of that is cheaper than any diligence you will ever pay for. Buying established is the risk mitigation. A business that has run 20 or 30 years takes real effort to break in the first couple of years if you run it roughly the way it has been run. The room does the work. Tim had no coach or formal mastermind in 2013. He had rooms full of people who thought buying a business was a normal thing to do, and the fear got quieter because it stopped being reinforced.   Resources Mentioned   The Buyer's Profile, a short assessment that shows you which parts of buying a business you are already strong in and which parts are actually in the way: powerofbiz.com/buyers-profile-survey   The Buyers Table, Tim's mastermind for people actively working toward buying a business.   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   "The only way to get past it is to just do the thing. There's no magic bullet other than feeling stupid for a little while." — Tim Delaney   "There are risks associated with not investing your money into yourself, and you should really be weighing those." — Tim Delaney   "Buying an established business helps mitigate the risk of failure, and therefore the risk of public failure." — Tim Delaney   "Don't just say I can't. Say how can I." — Tim Delaney

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 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 – 00:42] What Is an AI-Native Holding Company? [00:42 – 05:36] From Army Officer to AI Entrepreneur [05:36 – 09:55] Buying a Liquor Store by Walking In and Asking [09:55 – 12:23] Structuring a Low-Cash, Value-Add Deal [12:23 – 15:35] Turning AI Consulting Into Acquisition Flow [15:35 – 20:09] PE, Family Offices, and the Future of the HoldCo [20:09 – 23:45] The Biggest Tech Gaps in Small Businesses [23:45 – 28:29] Using AI Without Removing Human Judgment [28:29 – 35:38] Fit, Risk, Seller Financing, and Betting on Yourself   Guest Bio Zach Jones is an Army veteran, husband, father, and entrepreneur based in Augusta, Georgia. After serving as a commissioned Army officer for more than ten years, Zach began building AI tools and micro-SaaS products before moving into the intersection of AI and small business operations.    Connect with Zach:   Threads:         threads.com/@notindyjones Website:         gowaffl.com 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 you could do the same amount with less, then you should be able to do more with more." — Zach Jones  "You don't know what opportunities are out there unless you just go and start having conversations." — Zach Jones  "Fail forward instead of being stagnant." — Zach Jones

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 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 – 00:32] The Math Didn't Math [00:32 – 06:03] Kevin's Path from Residential to Self-Storage [06:03 – 09:01] Why Self-Storage Beat Tenant Problems [09:01 – 13:57] Coaching, Confidence, and Taking the First Jump [13:57 – 18:20] Trading a Sixplex for a Storage Facility [18:20 – 23:25] Finding the Deal and Making the Offer [23:25 – 30:00] Due Diligence and Boots on the Ground [30:00 – 42:55] Remote Operations, CapEx, and Financing Options [42:55 – 55:29] Buy Box, Hard Money, Coaching, and Going All In   Guest Bio Kevin Rapport is a self-storage investor, hard money lender, and coach for investors looking to get into self-storage. He started investing in residential real estate in 2009 while attending the University of Arizona, buying houses near campus and renting them to college students.  After building experience in residential rentals, small multifamily, construction, property management, and lending, Kevin transitioned into industrial and self-storage. Today, he invests in and operates self-storage facilities across multiple states, focuses on mom-and-pop facilities in tertiary markets, and helps other investors understand how to find, evaluate, finance, close, and operate self-storage deals.   Connect with Kevin: X:         @storage_venture Email:   [email protected] Websites:   www.myfoundingcapital.com / www.storageventure.com 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 "So the math—the math didn't math, right?" — Kevin Rapport  "If you never make the offer, you're never going to buy the thing, right?" — Kevin Rapport  "Most people build wealth becoming an expert in 1 or 2 things. They don't build wealth by becoming good at 15 things." — Kevin Rapport

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 dealership doing roughly $16 million in annual revenue. 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. Content note: This episode includes discussion of grief, depression, PTSD, and suicidal ideation.    00:00 – 01:34 | The Burning Junkyard and Seller Perspective 01:34 – 03:02 | The Car Dealership Alan Sold 03:02 – 08:15 | Choosing Ownership Over Security 08:15 – 13:21 | Launching From a Junkyard on Fire 13:21 – 18:38 | Learning Business Through Pizza and Systems 18:38 – 27:18 | Growing Through Financing, Customers, and Process 27:18 – 34:30 | Why Alan Decided to Sell 34:30 – 40:09 | Understanding the Seller's True Situation 40:09 – 50:51 | Healing, Coaching, and Final Lessons   Guest Bio Alan Underwood is a coach, speaker, investor, and entrepreneur who has built and sold multiple businesses, including pizza restaurants and a car dealership. His car dealership grew to two locations, earned strong customer reviews, built a major local following, and reached approximately $16 million in annual revenue.    Connect with Alan:   Instagram: instagram.com/thealanunderwood/   Facebook: facebook.com/alan.underwood.54   Website: thealanunderwood.com/   LinkedIn: linkedin.com/in/the-alan-underwood   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 "Pray hard, work hard, and treat people right." — Alan Underwood  "A business can be financially valuable and personally crushing at the same time."  — Alan Underwood  "The number on the offer sheet does not always tell the whole seller story." — Tim Delaney

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 when a high-margin inventory opportunity appeared.  Tim T. 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 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 – 01:39] Buying a Wine and Liquor Store [01:39 – 03:19] Reinvesting Instead of Pulling Cash Out [03:19 – 04:51] The Myth of Overnight Success [04:51 – 06:43] Opening a Line of Credit Before It Was Needed [06:43 – 08:33] Building the Relationship With the Landlord [08:33 – 09:57] Seller Financing and Negotiating Terms [09:57 – 10:56] Finding the Down Payment [10:56 – 12:50] The Roof Problem and Why Cash Flow Mattered [12:50 – 14:57] How One Business Can Change Your Life      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 Tim and the community: Website: https://www.powerofbiz.com YouTube: https://www.youtube.com/@powerofbiz Instagram: @timtdelaney Threads: https://www.threads.com/@timtdelaney LinkedIn: linkedin.com/in/timothytdelaney Facebook: facebook.com/timtdelaney   Tweetable Quotes: "You should have a plan to grow the business right from the start."  — Tim T. Delaney "The best time to ask a bank for credit is when you don't need it."  — Tim T. Delaney "A cash-flowing business can give you the confidence to take on the next asset." — Tim T. Delaney

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 break a transaction.  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 – 03:07 | Why Ryan Chose Buying Over Starting 03:07 – 07:27 | The Two-Year Business Search 07:27 – 14:29 | Ryan's Entrepreneurial Background 14:29 – 18:34 | Defining the Acquisition Criteria 18:34 – 27:36 | Off-Market Search and Broker Relationships 27:36 – 38:06 | Deals That Fell Apart 38:06 – 43:44 | The Distribution Business Opportunity 43:44 – 54:45 | Valuation, SDE, and Deal Structure 54:45 – 01:10:02 | SBA Financing, Closing, and Final Lessons   Guest Bio Ryan James is a successful business owner, real estate investor, and entrepreneur with experience across banking, wealth management, financial planning, public insurance adjusting, virtual assistant recruiting, and business acquisition. Ryan has started multiple businesses throughout his life, including a public adjusting company and a VA recruiting company that connects Filipino virtual assistants with U.S. businesses.    Connect with Ryan:   Email: [email protected]    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 "You're never going to have it all. If you have just enough, you'll figure everything else out." — Ryan James  "There's a million and one different ways you can structure a deal." — Ryan James  "Getting the reps in is important, but eventually you need to take that plunge." — Tim Delaney

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 discusses seasonality, vendor terms, industry differences, and the key question every buyer should ask a seller early in the process: what working capital target are you delivering at close, and how did you calculate it?  Tim T. 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 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 – 00:46] Why Working Capital Can Derail a Deal [00:46 – 02:24] What Working Capital Actually Means [02:24 – 03:40] Tim's Wine and Liquor Store Example [03:40 – 05:09] Working Capital Pegs in Larger Acquisitions [05:09 – 06:08] Seasonality and Month-to-Month Cash Needs [06:08 – 07:26] AR, AP, and Smaller Asset Purchases [07:26 – 09:13] Why Smaller Deals Still Need Working Capital [09:13 – 11:27] Real Buyer Examples: Cash Shortages and Bank Requirements [11:27 – 15:05] Industry Benchmarks and the Question to Ask Sellers   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 Tim and the community: Website: https://www.powerofbiz.com YouTube: https://www.youtube.com/@powerofbiz Instagram: @timtdelaney Threads: https://www.threads.com/@timtdelaney LinkedIn: linkedin.com/in/timothytdelaney Facebook: facebook.com/timtdelaney   Tweetable Quotes: "Most buyers and sellers are initially so focused on the purchase price or sometimes the terms."   — Tim T. Delaney "Don't get caught off guard at closing."  — Tim T, Delaney "If you buy a business and you don't have enough working capital right from the start, you can easily be out of business in just weeks."  - Tim Delaney