Buying Online Businesses Podcast

What if you could beat a higher offer without paying more? Justin Butlion knows how. He’s completed five micro SaaS acquisitions, built a 10-app portfolio, and spends roughly three hours a week managing it. His biggest deal? $98,000 with 50% seller financing. And that’s where this gets interesting. Justin isn’t trying to outbid everyone. He’s learning how to become the buyer sellers want to choose. Move fast. Understand the seller. Know the industry. Structure the deal so it works for both sides. And seller financing? Justin calls it a powerful weapon. He reveals how he negotiated deals with financing at under 2% interest, why developers often make surprisingly motivated sellers, and how the right terms can let you acquire more without putting all your cash on the line. But the real edge starts before you make an offer. Justin breaks down exactly what he looks for in a micro SaaS: B2B customers, sticky recurring revenue, low churn, simple tech, built-in distribution, and minimal operational risk. He also walks through how he analyzes the SaaS funnel to spot opportunities that the headline numbers might completely miss. Then there’s the part most acquisition conversations skip. What happens after you buy? Justin gets brutally honest about cash flow getting squeezed by seller payments, the hidden cost of managing multiple small businesses, his costly lessons with U.S. business structures, and why bigger acquisitions may ultimately make more sense. Because the goal isn't to own the most businesses. It’s to build the most valuable portfolio without giving up your life in the process. If you’re buying micro SaaS, negotiating acquisitions, or looking for ways to win deals without simply offering the highest price, this conversation is packed with strategies you can actually use. 🎧 Hit play and learn how to become the buyer sellers choose, even when your offer isn't the highest.   Episode Highlights 03:09 – How $98K in Cash Sitting Inside an Analytics Agency Sparked a Five-Deal Micro SaaS Acquisition Strategy 05:27 – The Micro SaaS Sweet Spot: Why Justin Buys Simple B2B Apps With Recurring Revenue, Low Risk, and Built-In Distribution 10:58 – The Due Diligence Advantage: Why 10+ Years of SaaS Experience Can Be the Difference Between a Great Deal and a Disaster 16:01 – The 1.7% Churn Discovery: How a SaaS With Weak Paid Conversion Revealed Massive Upside Through Its Existing Distribution 17:42 – The Seller Financing Playbook: How He Bought a $98K SaaS With 50% Seller Financing at Under 2% Interest 20:49 – How to Beat Higher Offers Without Paying More by Becoming the Buyer Sellers Trust Most 37:21 – The Bigger Acquisition Strategy: Why Justin Is Rethinking Small Deals, Raising Capital, and Building Toward a $20K MRR HoldCo  Key Takeaways ➥ Seller financing can be a powerful acquisition tool. Justin used it in three of his five deals, including his $98K acquisition with 50% seller financing, allowing him to preserve cash and continue building his portfolio. ➥ The best SaaS acquisition isn't necessarily the fastest-growing one. Justin prioritizes simple B2B SaaS, low churn, recurring revenue, built-in distribution, and low operational risk over aggressive growth. ➥ Distribution can be more valuable than the software itself. When buying SaaS, you're acquiring an existing audience, customer base, brand, and recurring revenue stream, not just a piece of code. ➥ Due diligence should go deeper than revenue. Justin analyzes the entire SaaS funnel, from installs and signups to activation, paid conversion, and churn, to understand how healthy the underlying business really is. ➥ You can win deals without being the highest bidder. Moving quickly, understanding the seller's motivation, demonstrating acquisition experience, and reducing the seller's perceived risk can make you a far more attractive buyer than someone simply offering more money. ➥ Seller financing can also become a cash-flow trap. Financing makes acquisitions easier to complete, but excessive monthly payments can consume the business's cash flow and leave little room for growth or unexpected expenses. ➥ The ultimate goal isn't owning more businesses, it's building wealth without sacrificing freedom. Justin's experience has pushed him toward larger, higher-leverage assets while carefully weighing growth, risk, capital, time, and the lifestyle he actually wants.   About Justin Butlion Justin Butlion is the founder of Hawkeye Ventures, a holding company that has acquired 10 micro SaaS apps generating over $93K ARR since 2022. After 7+ years working inside B2B SaaS companies as a marketer, product manager, and analyst, Justin turned to acquisitions instead of reinvesting his agency's marketing budget into ads. He writes SaaS Decoded, sharing deal breakdowns, due diligence lessons, and acquisition strategy for operators and buyers.   Connect with Justin Butlion ➥ https://www.linkedin.com/in/justin-butlion-54912129/   ➥ https://www.saasdecoded.com/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What can kill a $10.5 million acquisition, and how can an experienced buyer spot a bad deal in the first 10 minutes? Neil Twa has reviewed 500+ businesses and learned that the biggest red flags often show up before serious due diligence even begins. Messy financials. AI-generated business plans. Numbers that collapse when checked against the actual bank, Stripe, and PayPal data. And sometimes, even when everything looks right, the deal still falls apart. In this episode, Jaryd sits down with Neil to unpack the deal that looked so good the seller decided not to sell, the business deal that ghosted him after six months of due diligence, and the $10.5M acquisition that came with SBA financing, retail complexity, and a partner trying to sabotage the transaction. Neil also reveals why his team changes almost nothing during the first 30 days after an acquisition, how they operate 30 brands with AI-powered systems, and why reputation can be worth more than any single deal. If you're buying online businesses, this is a masterclass in spotting problems early, surviving the surprises you can't see coming, and knowing when to walk away. 🎧 Hit play to learn what an experienced acquirer can see in the first 10 minutes that could save you months, and potentially millions.   Episode Highlights 03:32 – How Neil Reviewed 500+ Businesses to Find the Few Deals Worth Buying 06:45 – The First 10-Minute Deal Killers: Messy Financials, Missing Documents, and Disorganized Seller Packages 07:58 – The AI Due Diligence Trap: How Fake Business Plans and Unverified Numbers Fall Apart Under Scrutiny 12:50 – The Deal That Looked Too Good to Sell: Why the Seller Backed Out Just Before Signing the LOI 16:17 – The 6-Month Ghosting Nightmare: When a Seller Disappeared After Months of Due Diligence 22:55 – The $10.5M Acquisition: How Neil Navigated SBA Financing, Retail Complexity and a Deal That Nearly Fell Apart 37:09 – Why Reputation Beats Money: The Trust Principle That Becomes More Important the Higher You Go 38:17 – The First 90 Days After an Acquisition: Why Neil Says Change Nothing for 30 Days and Learn Before You Optimize   Key Takeaways ➥ The first 10 minutes can save you months of wasted due diligence. Messy financials, missing disclosures, disorganized seller packages, and numbers that don't reconcile are early signals to walk away, not problems to hope will magically improve. ➥ AI doesn't replace credibility. A polished, AI-generated business plan means nothing if the seller can't explain the business behind it. Buyers need to verify the numbers, assumptions, and documents, not simply trust what AI produces. ➥ A great-looking deal can still fall apart for reasons you can't model on a spreadsheet. Neil had a seller back out just before signing the LOI because the diligence process made him realize how valuable his own business was. ➥ Due diligence doesn't end when you find the numbers you expected. Hidden liabilities, undisclosed agreements, missing inventory costs, and other surprises can surface right before or even months after closing. Structure the deal with those risks in mind. ➥ The first 90 days after an acquisition should be about learning, not immediately changing everything. Neil's approach is simple: spend the first 30 days changing almost nothing, map the business and its people, then identify the highest-impact improvements before acting. ➥ Operational complexity can create the biggest opportunities. Neil turned acquisitions with Amazon and retail channels into broader omnichannel businesses by identifying unused growth channels, improving systems, and using data to understand where growth actually creates value. ➥ Reputation compounds and becomes more valuable as you move up. Deals, capital, and relationships increasingly depend on trust. Neil's acquisition philosophy is built around being a "kingmaker": helping operators succeed while protecting the reputation and relationships that took years to build.   About Neil Twa Neil Twa is the CEO and co-founder of Voltage Holdings, where he and his clients have generated over $100 million in ecommerce sales since 2012. A former IBM executive, Neil has launched, scaled, and exited multiple 8-figure brands and mentored over 1,000 operators using his Train-Equip-Activate framework. He now focuses on building "generative" businesses engineered for margin and exit-readiness from day one, and helps buyers spot the difference between a business that looks great and one that actually is.   Connect with Neil Twa  ➥https://info.voltagedm.com/podcast-free-book    ➥https://voltagedm.com  ➥https://www.linkedin.com/in/neiltwa/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Everyone wants to know how to buy a great business. Almost nobody talks about how great businesses quietly become bad deals. After more than 300 business transactions, Joe Burrill has seen it happen time and time again. Sellers mentally check out months before they list. Buyers obsess over valuations while missing the risks that actually matter. And now, with AI changing the way online businesses are built, bought, and grown, the gap between good buyers and great ones is only getting wider. So what should you actually be looking for? In this episode, Jaryd sits down with Joe to unpack the lessons he's learned from brokering hundreds of online business sales. They explore why the best deals aren't always the fastest-growing ones, how experienced buyers think about traffic, revenue diversification, and risk, and why a simple conversation between buyer and seller can be more valuable than another spreadsheet. They also dive into how AI is reshaping acquisitions. Why content businesses aren't dead. Why SEO still matters. And where new buyers are getting due diligence completely wrong by relying too heavily on AI instead of using it as a tool. If you're thinking about buying your first online business - or your next one - this episode will change the way you evaluate opportunities. Because finding a business to buy isn't the hard part. Knowing which one is actually worth owning is. 🎧 Hit play and learn what 300+ deals have taught Joe that most buyers never find out until it's too late.   Episode Highlights 03:32 – How Joe Turned One Website Into a Career—and Eventually 300+ Business Deals  08:31 – The #1 Mistake Sellers Make That Quietly Destroys Their Business Value Before an Exit  12:02 – The $15K Deal That Used a $2K Holdback to Get Both Buyer and Seller to Say Yes 18:24 – The New Rules for Buying Content Websites in an AI-First World  24:08 – Why AI Won't Replace SEO—and the Costly Mistake Buyers Keep Making During Due Diligence 29:18 – The $172K Valuation Error AI Completely Missed—and Why Human Judgment Still Wins 37:15 – If You Had $20K–$100K Today, Here's Exactly What Joe Would Look For in an Online Business    Key Takeaways ➥ The fastest way to kill your exit? Stop running the business before it's sold. Buyers don't buy potential—they buy momentum. ➥ Deals close on trust, not spreadsheets. Strong buyer-seller relationships solve problems that contracts can't. ➥ One traffic source is a liability. Diversification is a premium. The more ways a business earns traffic and revenue, the more valuable it becomes. ➥ AI is a powerful assistant—not your deal advisor. It can speed up due diligence, but it can't replace experience, judgment, or pattern recognition. ➥ Content websites aren't dead. Generic content is. The winners are building brands, authority, and original insights that AI can't replicate. ➥ Creative deal structures create better outcomes. Seller financing, holdbacks, and flexible terms often turn stalled negotiations into closed deals. ➥ Buy the business you're best positioned to grow—not just the cheapest one you can afford. Your competitive advantage matters more than the asking price.   About Joe Burrill Joe Burrill started buying and selling websites in 2012 with a $700 acquisition. He's since closed over 300 transactions totalling more than $6.8M on Flippa, where he's been named the platform's most successful broker. As founder of Just Website Brokerage, Joe is the only Flippa broker to hold every badge the platform offers. He's the rare operator who's lived on both sides of the deal table many times over.   Connect with Joe Burrill ➥ https://www.justwebsitebrokerage.com/  ➥ justwebsitebrokerage.com/2026    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Everyone wants to know how to buy a great business. Almost nobody talks about how great businesses quietly become bad deals. After more than 300 business transactions, Joe Burrill has seen it happen time and time again. Sellers mentally check out months before they list. Buyers obsess over valuations while missing the risks that actually matter. And now, with AI changing the way online businesses are built, bought, and grown, the gap between good buyers and great ones is only getting wider. So what should you actually be looking for? In this episode, Jaryd sits down with Joe to unpack the lessons he's learned from brokering hundreds of online business sales. They explore why the best deals aren't always the fastest-growing ones, how experienced buyers think about traffic, revenue diversification, and risk, and why a simple conversation between buyer and seller can be more valuable than another spreadsheet. They also dive into how AI is reshaping acquisitions. Why content businesses aren't dead. Why SEO still matters. And where new buyers are getting due diligence completely wrong by relying too heavily on AI instead of using it as a tool. If you're thinking about buying your first online business - or your next one - this episode will change the way you evaluate opportunities. Because finding a business to buy isn't the hard part. Knowing which one is actually worth owning is. 🎧 Hit play and learn what 300+ deals have taught Joe that most buyers never find out until it's too late.   Episode Highlights 03:32 – How Joe Turned One Website Into a Career—and Eventually 300+ Business Deals  08:31 – The #1 Mistake Sellers Make That Quietly Destroys Their Business Value Before an Exit  12:02 – The $15K Deal That Used a $2K Holdback to Get Both Buyer and Seller to Say Yes 18:24 – The New Rules for Buying Content Websites in an AI-First World  24:08 – Why AI Won't Replace SEO—and the Costly Mistake Buyers Keep Making During Due Diligence 29:18 – The $172K Valuation Error AI Completely Missed—and Why Human Judgment Still Wins 37:15 – If You Had $20K–$100K Today, Here's Exactly What Joe Would Look For in an Online Business    Key Takeaways ➥ The fastest way to kill your exit? Stop running the business before it's sold. Buyers don't buy potential—they buy momentum. ➥ Deals close on trust, not spreadsheets. Strong buyer-seller relationships solve problems that contracts can't. ➥ One traffic source is a liability. Diversification is a premium. The more ways a business earns traffic and revenue, the more valuable it becomes. ➥ AI is a powerful assistant—not your deal advisor. It can speed up due diligence, but it can't replace experience, judgment, or pattern recognition. ➥ Content websites aren't dead. Generic content is. The winners are building brands, authority, and original insights that AI can't replicate. ➥ Creative deal structures create better outcomes. Seller financing, holdbacks, and flexible terms often turn stalled negotiations into closed deals. ➥ Buy the business you're best positioned to grow—not just the cheapest one you can afford. Your competitive advantage matters more than the asking price.   About Seph Fontane Pennock Seph Fontane Pennock is a serial entrepreneur and 8-figure exit founder who built PositivePsychology.com from a personal blog into one of the world's most visited mental health platforms, serving over 19 million users. He grew it to a PE acquisition without spending a dollar on ads, relying purely on SEO-led content strategy. Post-exit, he co-founded the SaaS platform Quenza and has since launched Regenerated.com. Seph is now an active investor and builder.   Connect with Seph Fontane Pennock ➥ https://www.linkedin.com/in/seph-fontane-pennock-94666421/   ➥ https://psychology.com/     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What actually causes most business acquisitions to fail? It usually isn't the price. Or the financing. Or even the due diligence. It's what happens after the deal closes. Too many buyers spend months negotiating the perfect acquisition, then expect two businesses, two teams, two cultures, and two sets of systems to magically become one. That's where things start to unravel. In this episode, Jaryd sits down with Julie Keyes, Certified Exit Planning Advisor, author of Poised for Exit, and host of the Poised for Exit podcast, to unpack why integration is the most overlooked part of buying a business and why it's often the difference between creating value and destroying it. They dive into the biggest red flags buyers should spot before making an offer, why customer concentration and owner dependency can quietly kill a deal, and the simple question every acquirer should answer before buying another company: "Why are we doing this?" Julie also shares why culture matters just as much as cash flow, how successful buyers prepare long before signing the paperwork, and why the smartest acquisitions aren't about buying revenue, they're about creating a stronger business for everyone involved. Because the best acquisitions don't end at closing. That's where the real work begins. 🎧 Hit play to learn how to avoid the mistakes that sink most acquisitions and build a business that's worth far more after the deal than before.   Episode Highlights 04:15 – The 4 Biggest Deal Killers Buyers Spot Immediately: Customer Concentration, Owner Dependency, Weak Cash Flow and One-Product Businesses 11:08 – Why Most M&A Integrations Fail Within the First 1–2 Years After Closing and How to Avoid Becoming Another Statistic 15:45 – How One Strategic Acquisition More Than Doubled a Global Health Business With 19 Patents 17:35 – The $3–4 Million Business That Never Sold Because the Owners Couldn't Let Go of Their Identity 20:02 – Why Chasing the Highest Sale Price Can Leave Sellers With Less Money After Taxes 21:18 – Earnouts Explained: Why Staying 1–2 Years After Selling Can Protect Both the Buyer and the Seller 24:42 – More Than 80% of Enterprise Value Comes From Intangibles The Hidden Assets Most Buyers and Sellers Undervalue   Key Takeaways ➥ The success of an acquisition isn't decided at closing, it's decided during integration. The biggest mistakes happen when buyers underestimate how long it takes to align teams, systems, technology, leadership, and culture. ➥ Before buying any business, ask one simple question: "Why?" The strongest acquisitions are driven by strategic fit, not ego, revenue growth, or the desire to simply own a bigger business. ➥ Customer concentration, owner dependency, unstable cash flow, and limited product diversity are major red flags. These risks can significantly reduce a company's value and make future growth much harder for a new owner. ➥ The best buyers plan for people, not just profits. Keeping key employees engaged, building trust early, and improving their day-to-day experience can create far more value than cutting costs after an acquisition. ➥ Many deals fail because owners aren't emotionally prepared to sell. Some overvalue their businesses based on personal attachment, while others back out entirely because they haven't planned what comes after business ownership. ➥ The highest purchase price doesn't always produce the best outcome. Smart deal structures, tax planning, earnouts, and payment terms often have a bigger impact on the wealth both parties ultimately keep. ➥ More than 80% of a company's value comes from intangible assets. Strong leadership, loyal customers, experienced employees, efficient systems, brand reputation, and company culture are often far more valuable than the physical assets on the balance sheet.   About Julie Keyes Julie Keyes is a Certified Exit Planning Advisor (CEPA), founder of KeyeStrategies, and author of Poised for Exit. With 30+ years as an entrepreneur, she's helped hundreds of private business owners build enterprise value and exit on their own terms. She's a two-time EPI Thought Leader of the Year, inducted into the Exit Planning Hall of Fame, and hosts the Poised for Exit podcast. Julie is EPI faculty and trains advisors and business owners across the country on exit strategy.   Connect with Julie Keyes ➥ https://www.linkedin.com/in/juliekeyes/  ➥ http://keyestrategies.com/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Most e-commerce brands are chasing AI the wrong way. They're publishing AI-generated blogs. Stuffing their sites with keywords. Obsessing over prompts. And wondering why nothing changes. Meanwhile, some brands are quietly growing their organic revenue by 30-40% year over year without relying on hacks or chasing the latest AI trend. The difference? They understand that AI hasn't replaced SEO. It's changed how people discover businesses. In this episode, Colin Ma breaks down the exact playbook he's using to grow established e-commerce brands through the combination of traditional SEO and Answer Engine Optimization (AEO). He explains why real customer questions are now one of the biggest competitive advantages, how a simple change to your collection pages can unlock entirely new traffic, and why optimizing your Google Merchant Center feed can drive thousands of additional clicks, often in just a couple of months. But the conversation goes well beyond rankings. Colin also shares how AI has completely transformed his workflow, allowing him to produce the work of an entire agency without sacrificing quality. From using Claude to analyze thousands of customer emails in minutes to building SEO assets that once took weeks, he reveals where AI actually creates leverage and where trusting it blindly can become an expensive mistake. If you're running an e-commerce brand, buying online businesses, or trying to figure out what SEO looks like in the AI era, this episode is packed with practical strategies you can apply immediately. 🎧 Hit play and discover why the future of SEO isn't about replacing the fundamentals. It's about using AI to execute them better than everyone else   Episode Highlights 05:00 - How Colin Is Driving 30-40% Year-on-Year SEO Growth for Household E-commerce Brands Using AI 08:10 - Why Real Customer Emails Beat SEO Tools Every Time When Optimizing for ChatGPT and AI Search 12:18 - The Collection Page Strategy That Most E-commerce Stores Miss and How It Unlocks More Organic Traffic 18:32 - How Optimizing Google Merchant Center Feeds Turned 200 Monthly Clicks Into Nearly 5,000 in Just Two Months 22:45 - Why Claude Has Made SEO Fun Again and the AI Workflow That Replaced Weeks of Manual Work 26:08 - The Dangerous Mistake Businesses Make by Trusting AI Blindly (And Why Colin Fired a Client Over It) 35:12 - Why Buying Pure Content Sites Is Riskier Than Ever and What Colin Would Look for Instead in the AI Era Key Takeaways ➥ SEO remains the foundation of AI search. Brands with strong SEO are far better positioned to appear in ChatGPT, Claude, and other AI-powered search platforms. ➥ Real customer questions outperform traditional keyword research. Mining support emails, live chats, and customer inquiries helps create content that matches how people actually search and how AI models understand intent. ➥ Better category pages create more growth opportunities. Expanding collection pages into more specific subcategories gives Google and AI search engines more relevant pages to rank. ➥ Optimizing your Google Merchant Center feed can generate fast wins. Richer product data improves visibility in Google's free listings while often boosting paid campaign performance as well. ➥ AI is a force multiplier, not a replacement for expertise. The biggest gains come from using AI to automate repetitive work so you can spend more time on strategy, analysis, and decision-making. ➥ Human judgment still matters. AI is incredibly powerful, but blindly accepting its recommendations without validating them can lead to costly mistakes. ➥ Sustainable growth comes from combining AI with genuine customer value. Businesses that solve real customer problems while using AI to execute faster will have the strongest competitive advantage in the years ahead.   About Colin Ma Colin Ma is a digital entrepreneur and SEO operator with over 10 years of experience building, buying, and selling online businesses. He's acquired, grown, and exited 15+ content and affiliate brands,  including multiple six-figure deals. Known for his data-driven, systems-first approach to SEO, Colin now manages a portfolio of large digital brands, using AI-powered workflows to drive 30–40% year-on-year growth with leaner, more consistent teams than ever before.   Connect with Colin Ma ➥ https://matchagrowth.com/ ➥https://www.linkedin.com/in/colinlma/     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

A business can look profitable. The broker can call it “SBA pre-qualified.” The numbers can seem solid. And the deal can still be a disaster waiting to happen. Because financing doesn’t just help you buy a business. Structured badly, it can trap you in a deal that should never have closed in the first place. Ami Kassar has seen what happens when buyers get this wrong. One e-commerce acquisition he discusses was built around a single product. Just weeks after the transaction closed, a better product hit the market. The business was dead. And that’s only one version of the risk. Buyers jump into industries they’ve never operated in. They rely too heavily on one product, one supplier, or one sales channel. They treat lender pre-qualifications like guarantees. They rush because a seller wants to close fast. Or they take expensive “easy money” because speed feels more important than structure. That’s where deals get dangerous. In this episode, Jaryd sits down with Ami Kassar to unpack what buyers need to understand before taking on acquisition debt — from why SBA pre-qualifications may mean far less than you think, to what lenders actually look for in you and the business you’re buying. They break down how to improve your fundability before the right deal appears, why post-close liquidity matters, when seller involvement can help get a transaction financed, and why working capital should be part of the conversation before you ever sign on the dotted line. But the bigger lesson goes beyond getting approved. Ami believes the smartest financing strategy is the one that gives you maximum flexibility — because the goal isn’t to build the biggest portfolio, take on the most leverage, or grow at a pace that destroys your sleep. It’s to structure a deal you can actually live with. 🎧 Hit play before you finance your first — or next — online business acquisition. This conversation could save you from the kind of deal that looks exciting at closing… and becomes expensive the moment reality hits.   Episode Highlights 03:16 - The Question Every Buyer Should Ask Before Taking on Acquisition Debt: What Could Bring This Business to Its Knees? 06:14 - Why an “SBA Pre-Qualified” Business May Not Be Financeable When a Real Buyer Shows Up 07:48 - The E-Commerce Risk That Can Kill an Acquisition Weeks After Closing: One Product, One Channel, No Backup 12:42 - Why the Lowest Monthly Payment Can Matter More Than the Lowest Interest Rate When Structuring a Deal 16:14 - The Fast-Close Financing Trap: Why a Seller Pushing to Close in Weeks Should Immediately Raise Questions 18:06 - What Lenders Actually Look at Before Funding You: Clean Books, Tax Returns, Credit and Your Existing Businesses 30:28 - The Predatory Lending Trap: How “Fast Money” Can Put a Stressed Business on a Treadmill That Kills It   Key Takeaways ➥ Ask what could bring the business to its knees before taking on acquisition debt. ➥ “SBA pre-qualified” does not mean guaranteed financing. The buyer, business, and lender appetite still matter. ➥ Lenders assess both the deal and the buyer—from industry experience to credit, tax returns, and financial discipline. ➥ The best financing structure creates flexibility through manageable payments, liquidity, and access to working capital. ➥ Rushing a deal can be costly. Fast closes, weak due diligence, and expensive short-term financing are major warning signs. ➥ Cash reserves matter after closing. Buyers need enough runway to handle setbacks without putting the business at risk. ➥ More debt and more acquisitions do not always mean more success. Build around your risk tolerance, lifestyle, and long-term goals.   About Ami Kassar Ami Kassar is the founder and CEO of MultiFunding and author of The Growth Dilemma. For over 25 years he's helped entrepreneurs across the US unlock creative, cost-saving financing solutions — from SBA loans to alternative debt structures — to grow companies, improve cash flow, and restructure debt responsibly. He advises the White House, Treasury Department, Congress, and the Federal Reserve Bank, and is frequently quoted in the Wall Street Journal, Forbes, and the New York Times. He writes a weekly column for 21 Hats   Connect with Ami Kassar ➥ MultiFunding LinkedIn  ➥ MultiFunding Facebook ➥ MultiFunding Instagram: @MultiFunding    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Finding a great business is only half the battle. The harder part? Convincing a lender that you're the person who should own it. That's where most acquisitions quietly fall apart. In this episode, Jaryd is joined by Jared W. Johnson, the top individual SBA loan producer in the United States, who's helped fund more than $800 million worth of business acquisitions. But this isn't just another conversation about lending. Jared has been on both sides of the table. He recently acquired a $600,000 eCommerce business himself. What caught his attention wasn't perfect systems or polished financials. It was the opposite. A business with outdated processes, inventory tracked entirely from memory, and obvious operational gaps that most buyers would see as red flags. He saw upside. Together, Jaryd and Jared unpack how the deal came together, why the business was relocated across states, how a 3PL simplified operations, and why keeping one long-term employee became one of the smartest decisions they made after the acquisition. They also pull back the curtain on how lenders really think. Why do buyers with strong incomes still get declined? What makes someone trustworthy in the eyes of a bank? Does your personal spending matter? And when a business has valuable assets like an email list, loyal customers, strong SEO, or a large social following, how much weight do lenders actually give them? Whether you're preparing to buy your first business or looking to finance your next acquisition, this episode gives you a clearer picture of what separates buyers who get approved from those who don't. The best deals don't always go to the highest bidder. They usually go to the buyer who's prepared. 🎧 Hit play and discover what lenders are really looking for before they ever approve a business acquisition loan.   Episode Highlights 04:14 - Inside Jared's $600K eCommerce Acquisition: Why He Bought a Business Most Buyers Would Walk Away From 12:36 - From California to Texas: How They Relocated the Business, Switched to a 3PL, and Kept Operations Running Smoothly 21:42 - The Top Reasons SBA Loans Get Declined - Even When the Business Looks Like a Great Deal 24:26 - How to Make Lenders Believe You're Ready to Buy Your First Business (Even Without Owning One Before) 27:45 - The "Leaky Bucket" Test: Why Your Personal Finances Can Make or Break an SBA Approval 31:09 - How Banks Really Value Email Lists, SEO, Social Media, and Other Intangible Business Assets 36:18 - The Simple Move That Can Turn a "Maybe" Into a Loan Approval When You're Short on Experience   Key Takeaways ➥ The best acquisitions often hide behind messy operations. What looks inefficient to most buyers can become an opportunity with the right systems and execution. ➥ Lenders don't just evaluate the business - they evaluate the buyer. Your experience, preparation, and financial discipline all influence loan approval. ➥ First-time buyers can still secure SBA financing by demonstrating industry knowledge, a clear plan, and the ability to operate the business successfully. ➥ Retaining experienced employees can be one of the smartest post-acquisition decisions. Institutional knowledge is often more valuable than documented processes. ➥ Your personal finances matter. Lenders view your spending habits, savings, and cash reserves as indicators of how you'll manage a business. ➥ Email lists, SEO, customer databases, and social media add value - but lenders focus on how they support consistent cash flow, not just their size. ➥ Buying the business is only the beginning. Long-term success comes from continuously improving operations, learning the business, and investing in the right people.   About Jared Johnson Jared W. Johnson is the biggest individual SBA producers in the United States, having closed over $800 million in SBA loans across his 15+ year career, the majority being M&A and business acquisition deals. As VP and Senior Business Development Officer at First Internet Bank, he's a two-time Coleman Publishing SBA BDO of the Year. He's also a business owner himself, having personally acquired and exited a manufacturing company. He hosts the Before You Buy or Sell a Business podcast.   Connect with Jared Johnson ➥ https://www.linkedin.com/in/jaredwjohnson/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Everyone evaluating a business purchase today fixates on the same thing. Can this survive AI? Wrong lens. Wrong era. Wrong way to size up a deal. Tony Xu ran product and engineering at Flippa for five years before taking over as CEO. He's sat behind the scenes of thousands of transactions, tracked which categories exploded and which quietly faded, and seen firsthand what happens once AI actually touches a working business. And he'll say something most of the doom content circulating right now won't. AI isn't hunting your business down. It's clearing out the grunt work inside it. Photo editing. Listing copy. Animation that used to demand a full production team. Rough drafts of ad creative. Tasks that used to consume a founder's entire week now take minutes. Treating that as a threat misses what it really is. A head start. But here's the part almost nobody admits out loud. Nothing essential has changed. Who you reach. What people remember about your brand. Whether your customers stick around. Claude can write your listing copy. It can't earn you a decade-long relationship that gets your product onto a shelf. It's not handling your cash flow. It's not securing your credit line. It's not the reason someone buys from you twice. The businesses pulling ahead right now aren't the ones hiding from AI. They're run by people who know precisely where its usefulness ends and the real value begins. In this episode, Jaryd talks with Tony about what's really moving inside Flippa's marketplace. Why $250K to $5M has become the sweet spot for the sharpest buyers. How specialist operators are walking into neglected businesses and multiplying category growth in a matter of months. The difference between a roll-up play and a specialist play. And why chasing "AI-proof" is precisely the wrong instinct to bring into diligence. They also break down the two warning signs that should end a deal immediately. How a buyer's own comfort with AI can cut a year-long ramp-up down to half that. And why the businesses that seem the most behind the curve might actually be the cheapest assets on the whole platform. The buyers nervous about AI aren't wrong to be paying attention. They're just tracking the wrong risk. Tony isn't. 🎧 Hit play. Straight from the person who built the platform. No hype, no scare tactics, just where the real opportunity is sitting.   Episode Highlights 02:55 - Inheriting the Throne: Taking Over as Flippa CEO After Eight Years of Blake's Leadership 04:05 - The Globalization of Flippa: Why 60% of European Businesses Are Now Being Bought by Americans 05:26 - Multi-Currency, AI Translation, and 158 Payment Options: The Infrastructure Behind Flippa's Cross-Border Boom 06:59 - From Sub-$10K Domains to $250K-$5M Deals: How the Sweet Spot of Flippa Acquisitions Has Shifted Over a Decade 08:49 - Why E-Commerce Remains the Gold Standard for First-Time Buyers and How to Pick the Right Vertical 11:30 - The 450,000-Buyer Marketplace: How AI Recommendations and Watchlists Make an Overwhelming Number of Listings Feel Personal 14:55 - From the Serbian DJ's 140-Business Roll-Up to Specialist Buyers Who Bring Their Own Distribution Network 22:10 - Tony's Contrarian Take on AI: Why It's Not a Strategy, Just an Operational Tool Everyone Will Eventually Use 26:40 - The K-Shaped Productivity Curve: Why AI Makes the Best Operators Two to Three Times More Effective 29:40 - What AI Still Can't Touch: Why Distribution, Brand, and Customer Trust Remain the Real Choke Points of Value 36:43 - Tony's First-Time Buyer Checklist: Distribution, Brand Personality, and Operational Soundness Before You Sign Anything 38:25 - The Two Dealbreakers: Regulatory Red Flags and Why You Need a Real Handover Plan With the Founder 40:49 - Flippa's New AI-Powered P&L Builder and Data Room: What's Coming Next for Sellers and Buyers   Key Takeaways ➥ AI isn't a strategy. It's just the next operational tool everyone adopts within months, the same way FBA and 3PLs did. Whatever edge it gives you today gets competed away fast. ➥ The best operators are now two to three times more productive than they were a year ago. AI doesn't replace the founder, it supercharges them. That turns a twelve-month turnaround into six. ➥ Nobody's handing Claude their ad budget and walking away. Distribution, customer trust, cash on the balance sheet, the real choke points of value are still completely untouched by AI. That gap is where the money is. ➥ Specialists beat generalists every time. Flippa's fastest-growing categories are led by people with niche expertise, not just capital. Find the vertical your skills can supercharge. ➥ You don't have to love the product to love the deal. Plenty of buyers acquire businesses they have zero personal interest in because they're hooked on the operations, the numbers, and the upside. ➥ Two things kill a deal fast: regulatory landmines and no handover plan. No license compliance or no founder transition period are both deal-breakers worth walking away from. ➥ AI is a tailwind for content, a wash for e-commerce, and a coin flip for SaaS. It all comes down to execution speed. Ship faster, cut churn, win. Sit still, and AI just made your competitor's job easier too.   About Tony Xu Tony Xu is the CEO of Flippa - the world's #1 marketplace for buying and selling online businesses. With a background spanning economics, accounting, and a CPA qualification, Tony spent years as Flippa's Head of Product and Engineering, architecting the platform tools that have powered hundreds of thousands of digital business transactions. He's led the development of game-changing innovations including LaurenAI (Flippa's AI-powered deal sourcing engine), the Buyer Directory, and Flippa's AI-driven valuation tools - making institutional-grade M&A accessible to everyday entrepreneurs.   Connect with Tony Xu ➥ Flippa.com (affiliate link, not for Eden) ➥ https://www.linkedin.com/in/tony-x-62037498/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Most people trying to win at SEO are asking the wrong question. How do I get my traffic back? Wrong question. Wrong game. Wrong decade. Steve Wiideman has thirty years in this industry. He's seen every update, every panic, every agency pivot. And he'll tell you something most people charging you monthly retainers will never admit. The traffic isn't coming back. AI overviews are eating clicks before you even show up. Agentic commerce means people are buying inside ChatGPT and YouTube without ever touching your website. Zero-click isn't coming. It's here. It's done. It's the new normal. And most agencies are still selling you 2019 with a new logo. But here's the thing nobody's saying out loud. The fundamentals never broke. The shortcuts did. Content farms. AI-generated blog factories. Link blasters. Agencies who promised more content meant more traffic. Google's March update didn't come out of nowhere. It was a warning that had been building for years. And it landed hard. In this episode, Jaryd sits down with Steve to talk about what's actually happening. Why the businesses winning right now stopped chasing rankings entirely. How one sentence in a Google Maps review took a brand new burger joint to number one in two days. What agentic commerce means for your revenue model. And why single-source dependency on Google is the single biggest risk any online business is carrying right now. They also get into why twenty real brand fans beat an entire link-building team. How to build content in a shrinking-click world. And the mindset shift separating businesses that are growing from the ones watching their dashboards collapse. The agencies lying to you about AI aren't villains. They just don't know what else to sell you. Steve does. 🎧 Hit play. Thirty years of SEO truth. No fluff. No spin. Just the conversation your agency should have been having with you a long time ago.   Episode Highlights 03:01 - Why Google's Latest Updates Actually Confirm That Nothing Fundamental Has Changed About Great SEO 05:53 - The Zero-Click Reality: Why Your Lost Traffic Isn't Coming Back and What to Do Instead 07:49 - EEAT, AI Content, and the March Update: What Google Is Really Saying to Content Site Owners Right Now 08:53 - The Multimodal Content Approach: How Smart Brands Are Scaling Blogs Beyond Just Written Articles 13:21 - Why Blasting Your Brand Across Every Platform Is a Trap and the Two to Three Platform Rule That Actually Works 17:50 - The Hard Truth About Traffic: Why Chasing Old Click Numbers Is the Wrong Game Entirely 24:26 - Agentic Commerce and the Future of Google: How People Will Buy Without Ever Visiting Your Website Again   Key Takeaways ➥ The traffic isn't coming back. Full stop. The businesses winning right now accepted that early and stopped wasting energy trying to recapture something that no longer exists. They moved on. You should too. ➥ SEO was never about gaming Google. It was always about people. If ten results show up in a search, the brand that earns the click, delivers something real, and gets remembered wins. That hasn't changed. It never will. ➥ Seventy percent or more of your traffic from one source isn't a business. It's a bet. And right now that bet is paying out less than it ever has. Single-source dependency on Google is the biggest hidden risk sitting inside most content businesses today. ➥ One authentic sentence in a Google Maps review took a brand new restaurant to number one in two days. That's not luck. That's semantic triples working exactly as intended. What other platforms say about you in real conversations on real pages matters more than most people realize - to Google and to every LLM pulling citations. ➥ Publishing great content and moving on is the old game. The new game is lighting a fire around every piece you create. Get it in front of real people fast. The speed of early engagement signals more than most SEOs will ever tell you. ➥ People are already buying inside ChatGPT and YouTube without ever visiting a website. Agentic commerce isn't coming. It's here. And if your business isn't set up to sell where your customers already are, you're invisible at the moment that matters most. ➥ Traffic was never the point. Revenue was. Clicks don't pay bills. Customers do. The fastest mindset shift any online business owner can make right now is stopping the obsession with the dashboard and starting to measure what actually matters - people buying, returning, and telling others.   About Steve Wiideman Steve Wiideman - known as "SEO Steve" - is the founder of Wiideman Consulting Group and co-author of SEO: Strategy & Skills, a college textbook used at universities across the US. With nearly 30 years in search, he's helped brands like Disney, Skechers, Public Storage, and Honda dominate organic traffic. A practitioner, scientist, and adjunct professor at UCSD and CSUF, Steve specialises in multi-location and e-commerce SEO and is one of the most trusted voices on navigating SEO in the era of AI search.   Connect with Steve Wiideman ➥ https://www.wiideman.com/ ➥ https://www.stevewiideman.com/ ➥ https://www.linkedin.com/in/seoexpert/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Most people buying businesses are looking for the obvious. The obvious growth. The obvious profit. The obvious opportunity. That's exactly why they miss the best deals. Kyle Brown spent years in investment banking and private equity evaluating acquisitions before ever buying a business himself. And what he learned was simple: The businesses that look the safest aren't always the best investments. And the businesses that look broken aren't always broken. When Kyle came across an ecommerce business that was barely breaking even, most buyers would have walked away. Declining performance. Frustrated owners. Uncertain future. On paper, it looked risky. But Kyle wasn't looking at the same things everyone else was. In this episode, Jaryd sits down with Kyle to unpack how investment bankers evaluate opportunities, how private equity investors think about risk, and how to value a business when traditional formulas stop working. They discuss why so many buyers become obsessed with multiples, how distressed businesses can create outsized returns, and the operational changes that helped turn a struggling acquisition back into a profitable company. But perhaps the biggest lesson is this: Buying a business isn't about finding perfection. It's about seeing something everyone else has missed. Most buyers never learn how to do that. Kyle did. 🎧 Hit play to discover what investment bankers know about buying businesses that regular buyers will never figure out exists.   Episode Highlights 03:36 - How a Kid From an 800-Person Farming-Town High School Broke Into Investment Banking and Private Equity 07:03 - The $1M-$3M EBITDA Businesses His Family Office Targeted — And Why HVAC Became Their Favorite Acquisition Category 08:29 - The 25-Year-Old Who Took Over a Newly Acquired Ecommerce Business Just 30 Days After the Seller Walked Away 12:12 - How an 8-Year-Old Relationship Led to an Off-Market Acquisition Opportunity Nobody Else Saw 16:09 - The Break-Even Business Dilemma: How He Valued a 7-Figure Revenue Company When EBITDA Was Essentially Zero 20:14 - Why a Business That Once Generated $500K+ in Earnings Could Suddenly Be Worth Just 1x SDE 26:00 - The Turnaround Strategy: How Adding Customer Service, Sales Processes, and Accountability Took the Business Back to Profitability 30:14 - Why He Refuses to Build a Fund, Raise Millions, or Chase a Big Exit Despite Having the Background to Do It   Key Takeaways ➥ The best acquisition opportunities rarely look perfect. Kyle bought a business that was essentially breaking even because he focused on what it could become, not just what it looked like on closing day. ➥ Investment bankers don't just analyze numbers - they analyze risk. Revenue, profit, and multiples matter, but understanding why a business is struggling is often far more valuable than the financial statements themselves. ➥ A declining business gets discounted twice. First through lower earnings, and then through a lower valuation multiple. That's why turnarounds can create outsized returns for buyers who know how to fix the underlying problems. ➥ Relationships create opportunities that search never will. Kyle wasn't actively looking to buy a business when the deal appeared. An eight-year relationship and a consulting conversation led to an off-market acquisition most buyers would never have seen. ➥ You cannot improve a business you don't understand. Before hiring people or changing processes, Kyle answered customer calls himself, learned the products, and got into the weeds of the operation. The best operators understand the front lines before they build systems. ➥ Most struggling businesses don't need a miracle. They need execution. Answering the phone, following up with customers, building a sales process, improving accountability, and fixing neglected marketing channels can have a bigger impact than any growth hack. ➥ Buying a business can feel like buying yourself a job at first. The goal isn't to avoid work on day one. The goal is to build systems, people, and processes that eventually give you the freedom to work on the business instead of being trapped inside it. ➥ Not every acquisition needs to lead to a fund, a roll-up, or a massive exit. Sometimes the smartest strategy is to buy a good business, improve it, enjoy the cash flow, and let future opportunities emerge naturally rather than forcing the next deal.   About Kyle Brown Kyle Brown is a Michigan State graduate who spent 5+ years in investment banking and private equity in Chicago before making the leap to operator. He ran an eCommerce HVAC distribution portfolio company from 2017–2020, discovered his passion for the business, and went on to acquire and exit industrial and eCommerce distribution businesses. Today he's the CEO of 1877ForParts.com — a niche HVAC parts eCommerce distributor with over 1 million parts in stock, applying institutional deal discipline to real-world small business ownership.   Connect with Kyle Brown ➥ 1877ForParts: https://www.1877forparts.com/  ➥ LinkedIn: https://www.linkedin.com/in/msukylebrown/  ➥ X: https://x.com/MSUKyleBrown    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Most people think the biggest risk in buying a business is overpaying. It's not. It's signing an LOI you don't fully understand. Moving fast because someone on the internet told you speed wins. Then finding yourself thirty, forty thousand dollars deep into a deal that was never going to close the way you structured it. Eric Hsu has seen it happen more times than he can count. Over 160 closed deals as an M&A attorney who exclusively represents buyers. And the pattern almost always starts at the LOI - that document most first-time buyers treat like a formality. AI can hand you twenty questions to ask a seller. It can flag risk, validate numbers, model theory. It's genuinely useful. And genuinely dangerous when you don't know what you're actually looking at. Because AI can't read why a seller gets vague about their Google Ads account in a way that means something. It can't tell you that annual subscription revenue the seller just collected isn't really theirs yet - and your client inherits every obligation to fulfil it. It doesn't understand deal psychology. It can't sit across from someone who built their business over thirty years and feel where the resistance is coming from. That's pattern recognition. That's what 160 closed deals actually buys you. In this episode, Jaryd and Eric pull apart exactly where AI helps, where it quietly misleads you, and where it has no business making the call. You'll learn: Why the LOI is the single most expensive legal mistake first-time buyers make - and what stress-testing one actually looks like before you sign The working capital trap that kills deals mid-diligence and leaves buyers choosing between injecting $100K cash or walking away with nothing How SBA lending rules have shifted since mid-2025 - and why brokers now favour cash buyers who show up lender-ready from day one What AI genuinely cannot replicate: pattern recognition, human behaviour, and the deal empathy that holds negotiations together The holdco structure Eric recommends for portfolio buyers - when to set it up, why before your first SBA close, and what it actually costs Why integrity issues during diligence are non-negotiable walk-aways - and the dating analogy that explains exactly why The glue of the deal is the relationship. The trust. The ability to get both sides on a call and actually work something out. AI can model the numbers. It can't do that. 🎧 Hit play - the most expensive legal mistake in your deal is the one you didn't know you were making.   Episode Highlights 03:32 - The Single Biggest Legal Mistake First-Time Buyers Make That Costs Them the Most Money 07:20 - The Working Capital Trap: How Buyers End Up $100K Apart From Sellers Halfway Through a Deal 13:43 - Why the Cheapest Time to Ask Questions Is Before the LOI - And How Most Buyers Get This Completely Backwards 19:50 - What AI Cannot Replicate in an M&A Deal: Pattern Recognition, Human Behaviour and Deal Empathy 23:30 - HoldCo Structures Explained: How to Set Up Your Portfolio the Right Way Before Your First SBA Close 35:39 - The Google Ads Red Flag: How a Seller Called Declining Traffic "Stable" and What It Really Meant 41:29 - Deal Psychology: Why the Glue of Every Deal Is the Relationship, Not the Data   Key Takeaways ➥ The LOI is not a formality - it's the foundation. Everything that goes wrong mid-deal or at closing can almost always be traced back to something that wasn't properly thought through before that document was signed. ➥ Speed without preparation isn't a competitive advantage. It's how you become the buyer who gets the door slammed in their face after wasting thirty thousand dollars in sunk costs. ➥ Working capital is not a detail to sort out later. If you don't align on it at LOI, you'll be renegotiating it under pressure - and that's when deals die or buyers get burned. ➥ AI is a tool, not a practitioner. It can hand you a checklist. It cannot tell you how this deal is going to play out, why the seller is hesitating, or what that vague answer about the Google Ads account actually means. ➥ Seller integrity during diligence is the single clearest signal you'll get. If they're not being straight with you when they want the money, they won't be straighter after they have it. ➥ Set up your HoldCo before your first SBA close if you plan to buy more than one business. Restructuring ownership after the fact means going back to the bank for permission. Getting it right once upfront costs less than fixing it later. ➥ The relationship is the deal. You cannot negotiate working capital, resolve diligence issues, or survive a hard conversation with data alone. Trust is built human to human - and no amount of AI can replace what happens when both sides get on a phone call and actually work it out together.   About Eric Hsu Eric Hsu is a business acquisition attorney and the founder of Clear Focus Law and SMB Law Group, specializing in M&A for small and medium-sized businesses. Recognized as a Rising Star in Mergers & Acquisitions by Super Lawyers, Eric works exclusively on the buyer's side, helping self-funded entrepreneurs negotiate, structure, and close deals - including SBA-financed acquisitions. With clients across the US, he's known for transparent pricing, deep SBA expertise, and helping corporate professionals achieve freedom through acquisition.   Connect with Eric Hsu ➥ https://www.linkedin.com/in/lawyer4smbs/   ➥ https://lawyer4smbs.com/   ➥ https://buyersblackbook.com/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What if the way you've been thinking about buying a business has been costing you money before you've even made an offer? Not a little money. A lot. The kind of difference that turns a three-times multiple into a thirty-seven-times multiple. The kind of gap that separates someone who buys themselves a job from someone who builds a portfolio that works without them. Brad Sugars has been on the right side of that gap for thirty years. Founder of ActionCoach - the world's number one business coaching franchise across 80 countries. Over a million business owners coached. Sixteen books written. And a personal acquisition track record built on one thing most buyers never develop: a framework. He once paid double what every other bidder offered. And still got the business for ten percent of what he knew it was actually worth. Because he could see value nobody else was looking at. That's not luck. That's a system. In this episode, Jaryd sits down with Brad to unpack the acquisition philosophy that the top one percent use - and almost nobody at entry level even knows exists. You'll learn: The difference between a job buyer, financial buyer, and strategic buyer - and why most people are stuck in the wrong category their entire career Why 60% of businesses listed for sale never sell, and how to exploit that fact The 50-10-3-1 rule every serious buyer needs to understand before looking at a single listing How to use vendor financing, share swaps, and capital injection to acquire without a war chest Why Brad asks "are you looking for investors?" instead of "are you looking to sell?" - and why that one shift changes everything The three things to audit the moment you take ownership - and why missing one will bleed you dry The due diligence mistakes that kill deals, crater offers, and send serious buyers running And the one line that should be on every buyer's wall: The deal of the century comes along every week. Don't fall in love with the business. Fall in love with the deal. Most buyers skip the process, buy the dream, and wonder why the numbers never add up. This episode is the antidote. 🎧 Hit play - this is thirty years of buying, selling, and coaching condensed into one conversation that hands you the whole playbook.   Episode Highlights 05:40 - Why Strategic Acquisitions Beat Financial Ones  09:07 - Goals Before Deals 13:21 - The Business Brad Paid Double For That Was Still Only 10% of What It Was Actually Worth 17:09 - The Japanese Coffee Company That Bought a Cleaning Business Just to Get to Its Customers 21:36 - How Brad Does Deals Nobody Else Is Bidding On  30:13 - The Three Things to Audit the Moment You Take Over Any Business  31:37 - The One Mistake That Kills Most Exits Before They Even Start  37:42 - The Client Who Came In at an Eight-Times Multiple and Left With Thirty-Seven  40:46 - How Brad Resets an Offer After Finding Skeletons in Due Diligence    Key Takeaways ➥ Know your goals and your rules before you look at a single listing. Without them, every decision you make will be emotional. And emotional decisions in acquisitions are expensive ones. ➥ There are three types of buyers - job buyer, financial buyer, strategic buyer. Most people spend their whole career in the wrong one. The money lives in strategic, where your acquisition solves a problem your existing business already has. ➥ Don't just value the EBITDA. Trademarks, licenses, intellectual property, trading rights - these are assets most sellers never quantify and most buyers never ask about. That gap is where the real deals are made. ➥ Sixty percent of businesses listed for sale never sell. The person across the table from you is more motivated than they're letting on. Patience and preparation are your biggest negotiating tools - not tactics or pressure. ➥ Vendor financing, share swaps, and capital injection are how serious acquirers move without needing a pile of cash. A bank will lend you money to buy a profitable company. They won't lend you money to run a marketing campaign. Use that. ➥ The moment you find something in due diligence that doesn't match what you were told, go back immediately. Not as a ploy. Not as a tactic. Because the numbers you built your offer on are no longer real - and pretending otherwise only hurts you later. ➥ Fall in love with the deal, not the business. If you can't brag about the structure, the multiple, the terms - it's probably not the right transaction at this point in time. The deal of the century comes along every week. Wait for one worth bragging about.   About Brad Sugars Brad Sugars is the founder, chairman, and president of ActionCOACH,  the world's number one business coaching franchise with 1,000+ offices in 80 countries. A self-made multi-millionaire from Brisbane, Australia, Brad started his first business at university, became known as "The Turnaround Kid," and has since coached over a million business owners worldwide. Author of 16 books including Billionaire in Training and Buying Customers, Brad's entire philosophy centres on one principle: a true business is a commercial, profitable enterprise that works without you.   Connect with Brad Sugars ➥ https://www.actioncoach.com/ ➥https://www.linkedin.com/in/bradsugars/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What if you attracted 50 buyers in two months - for a product you almost didn't list? That's not a marketing strategy. That's exactly what happened when 21-year-old Ovi Shekh posted Wisdomic AI on Acquire.com and watched his inbox fill up faster than he expected. Ovi is a CS student from Dhaka, Bangladesh. He's already exited two businesses before most people his age have submitted a single job application. His first exit came almost by accident - a COVID-era grocery delivery startup, quietly acquired after the buyer tracked him down on Instagram. His second was Wisdomic AI. An AI-powered academic research tool he'd spent eight months building. Ten thousand signups. Nineteen hundred active users. Fifty-plus universities. And a product he genuinely didn't want to let go of. But he listed it anyway. Just to see. Fifty-two inquiries later, he had a signed LOI with his chosen buyer. And then a better offer showed up. More money. Different vision. And Ovi walked away from it. Because here's the thing most first-time sellers never think to use as a dealbreaker - vision alignment. Not the highest number. Not the cleanest terms. Whether the buyer actually believes in what you built and will carry it forward the right way. That was the filter. That was the whole decision. The buyer Ovi chose went on to raise $700,000 using the asset Ovi sold him. Let that sit for a second. In this episode, Jaryd sits down with Ovi to unpack how a 21-year-old from Bangladesh navigated two exits, turned down a better offer on purpose, and figured out the rules of the acquisition game earlier than almost anyone around him. How he valued an eight-month-old SaaS with no ARR and a niche user base that didn't behave like typical consumers. Why he applied to Y Combinator eight times, got rejected every single time, and what that finally told him about where his leverage actually lived. And the one thing he says nobody tells you when you're building - that you don't get rich owning a startup. Only selling one. Most founders fall in love with their product and never let go. Ovi fell in love with his, listed it just to see what would happen, and walked away with a lesson worth more than the exit itself. 🎧 Hit play - this is what acquisition-minded thinking looks like when it starts at 21.   Episode Highlights 00:55 - Why Ovi Listed Wisdomic AI And Got 52 Inquiries Almost Immediately 02:55 - The Moment a Better Offer Arrived After the LOI Was Signed - And Why He Turned It Down Anyway 06:43 - How You Value an Eight-Month-Old SaaS With No ARR and a Niche User Base That Doesn't Behave Like Normal Consumers 09:36 - The COVID Grocery Startup, the Hub and Spoke Model, and the Instagram DM That Turned a Shutdown Into His First Exit 12:33 - Eight YC Rejections, a Grant But No Funding, and the Moment He Realized Bangladesh Was the Ceiling 18:04 - What He Told His University Audience About Leverage, Product Market Fit, and Finding a Buyer With Complementary Skills 22:12 - The One Piece of Advice That Has Nothing to Do With Business - And Everything to Do With Why You're Building   Key Takeaways ➥ Vision alignment beats the highest offer. Price gets you to the table. The right buyer gets your product to where it was always supposed to go. Know the difference before you sign anything. ➥ Your unfair advantage is the thing you build from. Ovi could code. His co-founder could market. Know what you bring that nobody else in the room has - and build your exit strategy around it. ➥ A low churn rate is a valuation argument. Researchers don't bounce like casual app users. When your user base is sticky by nature, that's a story worth telling every buyer in the room. ➥ You don't get rich owning a startup. Only selling one. Building is how you create the asset. The exit is how you actually collect. Most founders confuse the two until it's too late. ➥ An MVP with product market fit is worth more than a perfect product nobody's using. Acquirers and investors are buying traction, not polish. Ship it, prove it sticks, then have the valuation conversation. ➥ Retaining a small equity slice post-exit is insurance, not greed. Five percent of something that raises $700K is a very different number than 100 percent of something you can no longer scale alone. ➥ Time is the one thing money cannot buy back. Twelve-hour days in Claude Code mean nothing if nobody's waiting for you when you close the laptop. Build the business. But don't lose the life funding it.   About Ovi Shekh Ovi Shekh is a 21-year-old entrepreneur and CS student from Bangladesh who has already exited two businesses. He co-founded GetGroceryBD during COVID - an on-demand grocery delivery platform acquired by Bponi in 2023. He then built Wisdomic AI, an AI-powered academic research tool that grew to 1,900+ users and 50+ universities before attracting 50+ buyers on Acquire.com and successfully exiting. Now building Arklab AI and actively investing in small businesses, Ovi represents a new generation of acquisition-minded founders.   Connect with Ovi Shekh ➥ https://www.ovishekh.com/➥ linkedin.com/in/ovishkh    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.  See omnystudio.com/listener for privacy information.

What does it actually look like to buy 10 online businesses over 14 years - and still be standing? Not the highlight reel. The chargebacks, the 95% traffic drops, the seller-financed deal you hand back four months in because you simply can't make it work. The slow, painful realization that passive income was never really the point - ownership was. Brock Yates has been buying online businesses since 2012, starting with a $3,000 turtle website he found on Flippa with zero SEO knowledge and zero plan. By the time he quit his day job in Switzerland to go full-time, he had a portfolio of content sites generating more than his salary. Then the Google Helpful Content Update hit. And then ChatGPT changed everything. In this episode, Brock doesn't just share what went wrong - he shares what he actually did to crawl back, adapt, and build something more resilient on the other side.   In this episode, you'll learn: Why Brock handed a $220K–$280K e-commerce acquisition back to the seller after four months - and what he'd do completely differently today The one thing every first-time buyer underestimates: the seller's institutional knowledge and what disappears the moment they walk out the door How a 95% traffic drop forced him to rethink content sites entirely - and why the turtle website outlasted everything else in his portfolio The WooCommerce vs. Shopify decision that's shaping his entire content-to-commerce strategy now How he used ChatGPT to build a free tool in 20 minutes that took a brand-new GM vehicle site from zero to 1,000 email subscribers - and counting Why buying a business to "own for 10 years" changes every decision you make from day one The niche-selection mistake that kills most content sites before they ever have a chance to grow Whether you're sitting on a content site wondering what to do next, or you're a first-time buyer trying to avoid the mistakes most people only learn the hard way - this conversation is one of the most honest, practical accounts of what building an online portfolio actually looks like across a decade. 🎧 Hit play - this is what 10 acquisitions of real-world experience sounds like when someone's willing to tell you all of it. Episode Highlights 03:29 - How a $3K Turtle Website Turned Into His First Online Business and Had Its Money Back Within 12 Months 08:24 - The Vegas Breakfast Deal: Why It Became His Most Expensive Education 11:49 - The Real Cost of Skipping Due Diligence on a $250K Acquisition 15:26 - Why Handing the Business Back to the Seller Was the Best Decision Available 17:43 - How the Google Helpful Content Update Wiped Out a Portfolio He'd Spent Years Building - Right After He Quit His Day Job 24:31 - Why the One Property He Built Survived the Crash While Every Listicle-Only Site Quietly Died 31:45 - The 20-Minute ChatGPT Tool That Beat Months of Pinterest Ad Spend   Key Takeaways ➥ The seller's knowledge is part of the asset - and it walks out with them. Before you close, map every decision that still lives inside the founder's head. ➥ Due diligence isn't verifying numbers - it's finding costs that aren't on the P&L yet. Chargebacks. Expiring inventory. Hidden fees. The surprises that break deals hide in the operational layer. ➥ Seller financing only works as well as the relationship behind it. When Brock couldn't make payments, a real relationship meant a clean exit, not a lawsuit. ➥ The sites you focus on survive. The ones you abandon don't. In a portfolio, attention is the most important thing you allocate. ➥ Thin content was never a business, it was a bet on Google never changing the rules. Build for the reader. The algorithm catches up eventually. ➥ If your content site has traffic, it has buying intent. Capture it. WooCommerce on the root domain. Google Merchant Center. Set it up before you think you need it. ➥ The best tool to build is the one you were frustrated you couldn't find yourself.   About Brock Yates Brock Yates is an independent publisher behind GMT Central and AllTurtles, where he builds practical content brands for enthusiast audiences. His work focuses on SEO, content strategy, and adapting niche websites to major changes in search.   Connect with Brock Yates ➥https://gmtcentral.com/ ➥https://www.allturtles.com/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What if the biggest risk right now isn’t a bad deal - but doing nothing? While most buyers wait for the AI dust to settle, the ones who understand what’s happening are quietly buying assets at discounts that won’t exist a year from now. The shift isn’t theoretical. Digital Trends lost 90% of its Google traffic - from 8.5M clicks to 65K. HubSpot lost nearly half its organic traffic in two months. Atlassian dropped 35% as enterprise usage declined. Salesforce fell 28%. And Monday.com replaced a 24-person sales team with AI in minutes. This has already happened. So the real question isn’t if AI is reshaping the market - it’s whether you know which businesses are still worth buying, how to price the risk, and when to walk away. In this episode, Jaryd breaks down how to spot hidden value in “declining” assets, why some SaaS models are collapsing, and how AI risk can be used as leverage - not fear. Because the buyers winning right now aren’t panicking or waiting. They’re moving with a strategy. 🎧 Hit play - this is your edge in an AI-disrupted market.   Episode Highlights 00:47 - A practical guide to which business models are winning vs. losing in the AI era. 04:06 - Can AI cheaply replace this business’s core value? 06:21 - Digital Trends (-90% traffic) and HubSpot (major drop) show the new reality for content sites. 09:19 - SaaS shake-up: Atlassian, Salesforce decline; Monday.com replaces sales with AI. 16:42 - Branded e-commerce with real equity is the most AI-resistant play. 21:31 - AI-hit businesses = best deals if you use risk to negotiate, not walk away. 26:52 - Klarna shows AI can replace support at scale -cutting costs post-acquisition.   Key Takeaways ➥ Always ask: Can AI replace this business cheaply? If yes, don’t walk - reprice and structure with earnouts. ➥ Single-source traffic (like Google) is now a dealbreaker. Value current performance and build growth outside SEO. ➥ Use AI risk as leverage - lower the price and tie payments to future performance. ➥ AI-resistant businesses have proprietary data, a strong brand, and real customer relationships. ➥ Distressed, AI-hit businesses are undervalued - but only if you have a clear turnaround plan.   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Most people think buying businesses is a numbers game. Ace Chapman has done 200+ acquisitions - and he'll tell you the numbers are almost never the point. Ace has been in this game since the dot-com bubble. He almost sold a stock market simulator to a little Nebraska company called Omaha Securities - before it became Ameritrade. He got out of a real estate business right before 2008 hit. He's not lucky. He's built a framework for thinking about business ownership that most acquisition guys never arrive at, no matter how many deals they close. But here's where it gets interesting. Right now, while everyone else is hunting online businesses in the U.S., Ace is doing something completely different - buying offline deals in Latin America, where business brokers don't exist and most owners don't even know selling is an option. Hotels. Spas. Mental health clinics. Panama. Colombia. Argentina. He walked into a hotel recently and heard the front desk pitch his own spa to a guest checking in. In this episode, Jaryd sits down with Ace to unpack why he thinks every business is just inventory - and why holding on too long is the real risk most buyers never talk about. How he structures equity deals so he never has to build anything from scratch. And what a real portfolio actually looks like when you stop confusing operating businesses with wealth. Most buyers are waiting for the market to calm down before they make a move. Ace just went and found a completely different market - one where nobody else is even looking. 🎧 Hit play - this is what 200 acquisitions of hard-won experience actually sounds like in practice.   Episode Highlights [03:33] - Ace explains why retirement is the riskiest first-timer move most people ever make - and why most people don't realize it until it's too late. [11:38] - The mindset shift that changed everything: why buying a business to grow it actually defeats the whole purpose of buying in the first place. [15:45] - Ace reveals why he's moved almost entirely into offline, international deals - and why Latin America is where the real opportunity gap exists right now. [26:00] - The tanning salon roll-up story: how Ace transferred managers between two businesses to fix operations and marketing - without hiring a single new person. [31:00] - The "Chairman Strategy" explained: why Ace treats every business need as an acquisition problem, not a hiring problem. [37:27] - Why every business is going to fail eventually - and why the most rational thing you can do is always be working toward the exit. [39:09] - Ace's reframe that changes how you hold a portfolio: businesses aren't assets to protect. They're inventory.   Key Takeaways ➥ Every business will eventually go out of business - even the best ones. 99% of the original S&P 500 companies are gone. The only question is whether you exit on your terms or theirs. ➥ The real portfolio isn't operating businesses - it's what you build outside them. Royalties, equity positions, brokerage accounts. Ace took a group of royalties public. That's the game after the game. ➥ Stop hiring. Start acquiring. Ace transferred one manager between two tanning salons instead of hiring twice. When he needed marketing, he bought social media accounts in the niche. You don't build what you can buy. ➥ Timing the exit matters as much as building the business. Ace nearly missed the Ameritrade deal in 2001 and almost held through the 2008 real estate crash. After 200+ acquisitions, his rule is simple - you're always working toward the exit. ➥ Go where the buyers aren't. In the U.S., acquisition culture is loud and crowded. In Panama, Colombia, and Argentina, business brokers don't exist. Sellers don't know "multiples" is even a word. That gap is the opportunity.   About Ace Chapman Ace Chapman has been in Micro Private Equity for decades! Buying his first business at 19 with just $3,000, leveraging it into a $70,000 acquisition. Over 25+ years he has personally completed 200+ acquisitions across online and offline businesses, and built a 6-figure monthly income from his portfolio. Founder of Partners Equity Fund and author of The Ace Formula, Ace now consults founders and investors on building wealth through strategic business acquisitions. He's based in South America and coaches clients globally.   Connect with Ace Chapman ➥https://www.linkedin.com/in/ace-chapman/ ➥http://www.acechapman.com/  Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What if the best acquisition you'll ever make is the one nobody else bothered to look at? That's not a rhetorical question. That's exactly how Karl Hughes bought his first agency. While every other buyer was refreshing broker listings and fighting over the same tired deals, Karl built a spreadsheet, started cold DM-ing podcast production founders on LinkedIn, and had fifty conversations most people would've deleted without a second thought. No broker. No bidding war. No competing offers. Just Karl, a thesis, and the patience to work a room that nobody else had walked into yet. One of those conversations turned into a sub-million-dollar acquisition at 2.7x SDE -a healthy, cash-flowing business with clients who'd been around for five-plus years. The seller had never seen a competitor's P&L in his life. Karl had seen twenty before he ever made the call. But here's where it gets interesting. That deal was just the beginning. Since then, Karl has been quietly building a portfolio of niche marketing agencies -the kind that are too small for private equity, too owner-dependent for most buyers, and too overlooked for anyone to notice the opportunity hiding inside them. Financing deals creatively. Targeting founders who are ready to move on. And figuring out in real time what it actually takes to merge two similar agencies without torching the clients that made them worth buying in the first place.  In this episode, Jaryd sits down with Karl to unpack why small agencies rarely get a real exit -and why that's the opportunity. How Karl showed a seller the actual debt math before making an offer and closed with trust instead of pressure. And what he'd do completely differently if he had to start the integration process over again from day one. Most buyers wait for a clean deal to fall into their lap. Karl just built his own pipeline and went to find it. 🎧 Hit play - this is what a quiet, deliberate acquisition strategy actually looks like in practice.   Episode Highlights 03:30 -Why Small Agencies Never Get a Real Exit -And Why That's Your Opportunity 09:29 -The LinkedIn Cold DM Strategy That Found a Deal Nobody Else Was Looking At 17:00 -The P&L Advantage: How Karl Saw 20 Competitor Financials Before Making a Single Offer 21:20 -Showing the Seller the Debt Math: The Transparency Move That Closed the Deal 33:28 -Karl Flips the Script and Asks Jaryd the Question Every First-Time Buyer Is Afraid To Ask 37:00 -Debt vs Equity: What Structure Actually Makes Sense for Small Agency Deals 39:00 -Never Buy a Distressed Agency First -Unless This One Condition Is Already Met Key Takeaways ➥ Being an operator is your unfair advantage. Karl didn't walk in as a finance guy with a briefcase. He walked in as someone already running a real agency. That credibility alone got doors open that cold outreach never could. ➥ Off-market deals aren't found -they're built. Karl spent months talking to founders who had no intention of selling. Some came back a year later. Patient relationship-building in one vertical is how you end up as the only offer on the table. ➥ See more P&Ls than anyone else in the room. Karl reviewed 20 competitor financials before making a single offer. The seller had seen zero. That knowledge gap isn't an edge you stumble into -it's one you build deliberately. ➥ Transparency closes deals faster than pressure ever will. Karl showed sellers the actual debt math behind his offer price. Not to impress them -to build enough trust to close without a broker, a bidding war, or months of back and forth. ➥ Shadow the team before you ever think about cutting it. The most valuable things a client-facing employee does are invisible until they're gone. Let both teams learn from each other first. The redundancies will surface on their own.   About Karl Hughes Karl Hughes is a former CTO turned serial agency acquirer. He founded Draft.dev in 2020 -a technical content marketing agency -and scaled it to $2.5M in revenue before stepping back from day-to-day operations. In 2023, he partnered with a co-buyer to acquire The Podcast Consultant without a broker, sourcing the deal directly via LinkedIn outreach after reviewing 200+ agencies. He now hosts the Retained Trust podcast and is actively building a portfolio of niche digital service businesses in the $1M–$5M revenue range.   Connect with Karl Hughes ➥ https://www.karllhughes.com/   ➥https://www.linkedin.com/in/karllhughes/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.