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 place.

She breaks down what it takes to remove yourself from day‑to‑day operations, how to evaluate owner‑dependent businesses, and why hiring, systems, and feedback loops are critical to scaling without becoming the bottleneck.

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 – 01:20] Intro & Ashley's background

[01:20 – 05:18] Early start in real estate and taking responsibility young

[05:18 – 08:55] Mindset around risk, fear, and learning through mistakes

[08:55 – 11:55] First business acquisitions and lessons from laundromats

[11:55 – 17:05] Entering residential care facilities and identifying opportunity

[17:05 – 21:05] Systems, scaling, and removing owner dependency

[21:05 – 24:50] Hiring, leadership, and building strong teams

[24:50 – 30:40] EOS, structure, and operational discipline

[30:40 – 35:16] Buying and systematizing a restaurant business

[35:16 – 38:36] Technology, data, and operational efficiency

[38:36 – 41:07] Growth strategy for residential care facilities

[41:07 – 43:15] Feasibility, market demand, and evaluating opportunities

[43:15 – 46:02] Mentorship, masterminds, and accelerating growth

[46:02 – End] Final advice for business buyers and operators

Guest Bio

Ashley Coates is a real estate investor, broker, and operator with over two decades of experience across real estate, business acquisitions, and operations. She specializes in converting residential properties into licensed care facilities and building scalable, system‑driven businesses that run without day‑to‑day owner involvement. Ashley is also the founder of Residential Care Collective, where she helps investors and operators build and grow residential care businesses.

Connect with Ashley:

Instagram: https://www.instagram.com/mikeandashleycoates/

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

"Every lesson was very expensive — and I learned it three times." – Ashley Coates

"You have to understand the owner dependency before buying any business." – Ashley Coates

"Systems and leadership are what allow a business to scale without you." – Ashley Coates

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 operating.

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 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 – 00:30] Context: Industries vs. Fit Tim introduces the topic of "top industries" and explains why the industry itself isn't what determines success.

[00:31 – 01:40] You Don't Have to Love It—But You Can't Hate It Why personal alignment with the business matters more than chasing a trending category.

[01:41 – 03:10] Healthcare-Adjacent Opportunities Housing, elderly services, non-emergency transport, equipment servicing, billing, and wellness businesses positioned for growth as populations age.

[03:11 – 05:10] Service Businesses That Must Be Done In-Person Cleaning, landscaping, cooking, and location-dependent services that are harder to outsource and more resistant to automation.

[05:11 – 06:20] Skilled Trades: Opportunity With Caution HVAC, electrical, plumbing, and roofing—great businesses, but often require licensing and operational experience.

[06:21 – 07:25] Experience-Based Businesses Escape rooms, fitness studios, kids' activity centers, and experiential services built around memory-driven spending.

[07:26 – 08:50] Business-to-Business (B2B) Services Parking lot sweeping, shredding, data backup, pest control, and other "invisible" businesses that quietly power local economies.

[08:51 – 10:20] Niche & Light Manufacturing Small manufacturers producing specialized parts within established supply chains—often owned by founders approaching retirement.

[10:21 – 11:50] Words of Caution Avoid trendy spikes, highly owner-dependent operations, and businesses with weak fundamentals regardless of industry hype.

[11:51 – 13:20] The Real Filter: Lifestyle, Cash Flow, Risk The best business is the one aligned with your life and financial goals—not the one on a "top industries" list.

[13:21 – End] Final Takeaway & CTA Start evaluating opportunities through fit and fundamentals, not headlines. Subscribe and continue learning through upcoming episodes.

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:

"A bad business is not going to be fixed by just the fact that the industry is taking off right now." - Tim Delaney

"You don't have to love it—but you can't hate it. If you hate doing that type of business, it will not be successful".- Tim Delaney

"The person makes the business, the cashflow makes the business, the structure makes the business." - Tim Delaney

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 evaluating listings and working with brokers to navigating financial surprises and confidence hurdles, Joe shares the honest, in-progress journey of becoming a first-time buyer.

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 – 02:20] Why Starting From Scratch Isn't Always the Answer

Joe reflects on the learning curve of launching a business and why buying an existing operation can be a smarter path.

[02:21 – 05:30] Joe's Background & Motivation

Balancing a demanding corporate career while pursuing financial independence through business ownership.

[05:31 – 09:10] From Gym Owner to Business Buyer

Lessons from Joe's first venture and why he shifted toward acquisition instead of another startup.

[09:11 – 13:00] Finding a Target Business

How conversations with family led to exploring boat tour companies and the process of searching listings.

[13:01 – 18:20] Outreach, Brokers & First Steps

Signing NDAs, reviewing CIMs, and navigating the early stages of evaluating a real opportunity.

[18:21 – 24:30] Financial Surprises & Deal Breakdown

How updated numbers changed the valuation and ultimately caused the deal to stall.

[24:31 – 33:40] Rethinking the Approach

What Joe learned from the failed deal and how it reshaped his acquisition criteria.

[33:41 – 44:50] Building Buyer Confidence

Mentorship, community, and why first-time buyers struggle with taking action.

[44:51 – 53:30] What Joe Is Looking For Now

Operational simplicity, remote ownership potential, and long-term financial independence goals.

[53:31 – End (~57:00)] Final Takeaways

Lessons for aspiring buyers and the mindset required to pursue acquisition instead of starting from zero.

Guest Bio

Joe Trotto serves as Director of Field Services at GE Vernova, where he leads teams and operations within the power generation industry. Outside of his corporate role, he's a husband and father of three who brings an optimistic, people-first mindset to everything he does. Joe is currently exploring business acquisition as a path toward long-term financial independence and greater control over his time and future.

Connect with Joe:

LinkedIn: https://www.linkedin.com/in/joetrotto/

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 pain associated with the learning curve of figuring out the nuts and bolts of an operation are not something I wanted to do." - Joe Trotto

"But even if something is struggling, it's easier to take something that's struggling and prop it up than to dig and lay the foundation anew." - Joe Trotto

"There is a learning curve associated with starting from zero." - Joe Trotto

"I want to have some sort of platform, some sort of foothold to go from so I don't have to start from scratch." - Joe Trotto

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 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 – 01:15] You've Heard About Buying a Business—Now What?

Tim opens by addressing the moment most people are in when they first discover business acquisition and aren't sure what to do next.

[01:16 – 03:00] Start Looking Before You're Ready

Why reviewing business listings early—without pressure to buy—helps build intuition and confidence.

[03:01 – 03:55] The Reality of "No Money Down" Deals

Breaking down why most buyers still need some form of capital, even when creative financing is involved.

[03:56 – 05:45] Building Capital Early

How saving money, improving cash flow, and preparing financially gives buyers more leverage later.

[05:46 – 06:45] Eliminate Before You Specialize

Why narrowing down what you don't want is often more helpful than chasing the perfect business.

[06:46 – 07:05] When to Be More Aggressive

How buyers with capital or experience should move differently and focus their efforts.

[07:06 – 08:05] Why Brokers Forget Generic Buyers

Why vague buyers don't get remembered—and how specificity makes brokers think of you when deals come up.

[08:06 – 08:45] Be Proactive With Brokers and Advisors

Why reaching out consistently matters more than waiting for opportunities to land in your inbox.

[08:46 – 09:40] Finding Opportunities Outside Listings

How networking, referrals, and local connections uncover deals that never hit marketplaces.

[09:41 – 10:30] Exposure Is the Real Win Early On

Why learning and seeing deals is more valuable than closing one too fast.

[10:31 – 11:15] You Don't Need Millions to Start

Tim explains why most people underestimate how accessible business acquisition really is.

[11:16 – End (~12:00)] Final Thoughts

Encouragement to start now—build knowledge, relationships, and momentum before trying to buy.

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 don't have to be ready to buy to start learning." – Tim Delaney

"If you're too generic, you're not going to stand out." – Tim Delaney

"You don't need millions." – Tim Delaney

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 most valuable skills she developed as a buyer.

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 – 08:20] From Employee to Founder

Milan describes the mindset shift required to move from employee thinking to ownership, and why she didn't fully grasp that transition until she was already deep into the process.

[08:21 – 16:20] Early Assumptions & Missed Math

How moving too fast, skipping the numbers, and relying on optimism created blind spots that could have led to a costly mistake.

[16:21 – 24:00] Red Flags & Reality Checks

Milan breaks down the moment she realized the deal might be a "dumpster fire," and how recognizing operational and structural issues changed her approach.

[24:01 – 36:30] Non-Operating Business Risk

Why buying a business that isn't actively operating introduces a completely different risk profile — and why that realization became a turning point.

[36:31 – 49:00] Knowing When to Walk Away

The emotional and strategic challenge of stepping back from a deal, even when the desire to buy is strong.

[49:01 – End] Lessons for First-Time Buyers

Milan's key takeaways for buyers evaluating their first acquisition, including patience, discipline, and respecting what the numbers are telling you.

Guest Bio

Milan Nolen is an entrepreneur and business buyer who focuses on disciplined deal evaluation, risk awareness, and long-term sustainability. Through her experience navigating potential acquisitions, she emphasizes the importance of math, operational clarity, and the confidence to walk away from deals that don't make sense.

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 Milan:

Instagram: @milanterez TikTok: @milanterez Website: milantereznolen.com

Connect with Tim and the community on social media for more tips and updates:

Website: https://www.powerofbiz.comYouTube: 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

"Either this is a complete dumpster fire, or there's a deeper reason here." – Milan

"I still want to buy a business — I just don't think this is the one to do it with." – Milan

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 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 – 02:30] ROI Is More Than a Spreadsheet

Tim explains why ROI shouldn't be viewed as just a financial formula, but as a broader measure of freedom, risk, and opportunity cost.

[02:31 – 06:15] What ROI Really Measures

Breaking down how ROI is calculated, what it includes, and why purchase price matters more than most buyers realize.

[06:16 – 12:45] Cash-on-Cash Return Explained

How cash-on-cash return works, why leverage dramatically changes outcomes, and how financing can increase early returns.

[12:46 – 18:30] Leveraged vs. Unleveraged Returns

Comparing all-cash purchases to financed deals and explaining why cash-on-cash returns are often much lower in pure cash acquisitions.

[18:31 – 26:40] Real-World Business Example

Walking through how owner pay, debt paydown, and equity growth affect actual cash coming back to the buyer.

[26:41 – 34:50] Comparing ROI Across Investments

How small business returns stack up against stocks, bonds, and real estate — and why business ownership should demand higher returns.

[34:51 – 42:30] Time, Effort, and Risk

Why there is no universal "good" ROI number, and how stability, workload, and industry risk should shape return expectaions.

[42:31 – End (~45:00)] Final Thoughts

Why ROI is only one part of the decision-making process and how buyers can avoid chasing.

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:

"ROI isn't just a spreadsheet formula — it's also a freedom calculation." – Tim Delaney

"Cash flow and profit are not the same thing, especially when debt is involved." – Tim Delaney

"There is no single ROI number that works for every business or every buyer." – Tim Delaney

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 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 – 11:40] Burning the Boats

Tiffany shares why she quit her job early, the mindset behind "burning the boats," and why she now believes timing and preparation matter just as much as courage.

[11:41 – 24:55] Learning the Hard Way

The realities of entrepreneurship after leaving a steady paycheck, early missteps, and how pressure can accelerate growth — or expose cracks fast.

[24:56 – 38:10] Confidence vs. Readiness

Why believing in yourself isn't always enough, how overconfidence can backfire, and the systems Tiffany wishes she had built sooner.

[38:11 – 45:30] Redefining Success

How Tiffany's view of freedom, income, and sustainability evolved as she gained experience — and why stability matters more than proving a point.

[45:31 – End] Lessons for the Leap

Tiffany's advice for anyone considering quitting too early, what she'd do differently now, and how to approach risk with clearer eyes.

Guest Bio

Tiffany Kao is an entrepreneur and creator who shares honest insights about the realities of self-employment, risk-taking, and personal growth. Through her experiences leaving traditional work and navigating entrepreneurship, she emphasizes thoughtful decision-making, resilience, and redefining success on your own terms.

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 Tiffany:

Instagram: https://www.instagram.com/tiffany_on_the_go_/

Connect with Tim and the community on social media for more tips and updates:

Website: https://www.powerofbiz.comYouTube: 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

"I promptly quit my job — which, by the way, is highly not recommended — but I was young and strong-headed, and somebody had given me the speech about how you need to burn your boats." – Tiffany Kao

"Confidence without preparation can put you in a really tough spot." – Tiffany Kao

"Looking back, I would've timed my leap very differently." – Tiffany Kao

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 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 – 02:15] Is a $200K Build-Out Still Worth $200K? Tim opens with a simple but critical question: if a business isn't profitable, does the money spent building it out matter at all?

[02:16 – 05:00] Breaking Down the Original Deal Reviewing the details of the post: a struggling food business, $6,000 monthly rent, long-term lease, franchise involvement, and no meaningful profit.

[05:01 – 06:45] You're Not Buying a Business Why this deal is really about taking over a lease and a space—not acquiring a functioning business.

[06:46 – 08:30] The Sunk Cost Fallacy Explained What sunk costs are, why sellers fixate on them, and why buyers should never pay for money that's already gone.

[08:31 – 10:20] Lease Risk and Personal Guarantees How long-term leases, rent obligations, and personal guarantees can quietly become the biggest threat to a buyer.

[10:21 – 12:30] What Is This Business Actually Worth? Why a business with zero cash flow has little to no value, and why used restaurant equipment usually sells for pennies on the dollar.

[12:31 – 14:40] Franchise and Legal Red Flags Potential issues with rebranding, franchise agreements, and trademark risks that buyers often overlook.

[14:41 – 16:30] Don't Pay for Someone Else's Mistakes Why turning around a failed business requires a very different skill set—and why confidence alone isn't enough.

[16:31 – End] Final Thoughts Cash flow is king. Without it, even a "great location" and expensive build-out can't justify a bad 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.comYouTube: https://www.youtube.com/@powerofbiz Instagram: @timtdelaneyThreads: https://www.threads.com/@timtdelaney LinkedIn: linkedin.com/in/timothytdelaney Facebook: facebook.com/timtdelaney

Tweetable Quotes:

"Money already spent does not equal value." – Tim Delaney

"If a business has no cash flow, it isn't a business—it's a liability." – Tim Delaney

"Confidence doesn't fix bad numbers." – Tim Delaney

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 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.

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:

"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

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 successful business. From understanding what guests actually value to maintaining a brand that feels authentic, Ian offers a grounded look at what ownership really means beyond the aesthetics.

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 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 BiggerPockets Money, BiggerPockets Rookie Real Estate and The Freedom Chasers Podcast.

[00:00 – 15:20] From Curiosity to Ownership

Ian shares how he got involved with Billy Motels and why hospitality appealed to him. What he learned early about renovating, rebranding, and creating guest experiences. The transition from employee to full owner and what that meant in real terms.

[15:21 – 32:45] The Reality of Running a Hospitality Business

Daily challenges of operations: staff management, turnover, and systems. How design, service, and customer experience work together. Learning to balance authenticity with profitability.

[32:46 – 47:30] Growth, Brand, and Balance

The philosophy behind Billy Motels — simple, intentional, and rooted in community. How Ian learned to separate his personal taste from what guests actually want. What it takes to build culture and consistency without losing creativity.

[47:31 – End] Ownership Lessons

What surprised him most about being a hospitality entrepreneur. Why ownership is more about people and mindset than spreadsheets. Advice for anyone wanting to buy or operate a hospitality business.

Guest Bio Ian Joseph is the co-owner of Billy Motels, a hospitality brand known for its thoughtful design and community-driven approach. With a background outside of traditional hospitality, Ian brings a unique perspective to ownership — focused on operations, culture, and learning by doing.

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Connect with Ian Joseph: Instagram: instagram.com/ijoseph09/

instagram.com/staywithbranch/

instagram.com/billymotel/

instagram.com/theishkitchen/

Website: https://staywithbranch.com/

https://www.thebillymotel.com/

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 don't really know what it's like until you're the one signing the checks." – Ian Joseph

"Every mistake teaches you more than any course ever could." – Ian Joseph

"Good systems fix bad habits." – Ian Joseph

"The goal isn't to make it look easy — it's to make it work." – Tim Delaney