Buying Online Businesses Podcast

Most people think buying a business is just about finding a “good deal.” Kevin Peterson has done over 50 acquisitions - and he’ll tell you that’s exactly how people lose money. Because what brokers don’t tell you…  is that the real risk isn’t the numbers? It’s what’s missing behind them. Like the SaaS deal that looked perfect on paper… until the entire team walked out right after closing. Or the “growth opportunity” that was actually just an audience no one had ever monetized. Or the biggest trap of all - buying a business without a clear thesis… and hoping it works out later. In this episode, Jaryd sits down with Kevin - founder of Webfolio Management - who’s spent the last 12+ years acquiring, operating, and scaling digital businesses across SaaS, content, and eCommerce. And this one goes deep. Into the real due diligence signals most buyers miss. Into how AI is quietly changing what businesses are worth buying - and which ones are becoming obsolete. Into the hidden risks inside “easy wins” like audience monetization and roll-ups. But more importantly… Kevin breaks down the exact thinking behind building a portfolio that doesn’t just grow - but actually survives. No hype. No shortcuts. No theory. Just hard-earned lessons from someone who’s done the deals, made the mistakes… and kept going anyway. 🎧 Hit play - this is what buying businesses really looks like.   Episode Highlights 02:27 The Career Pivot That Changed Everything – From 20 Years in Consulting to Buying Online Businesses 03:36 From $50K Deals to 7-Figure Acquisitions – How Kevin Built a 50+ Deal Track Record 06:08 The Hidden Value Most Buyers Miss – Untapped Audiences That Can Instantly Increase Revenue 09:22 The Deal That Looked Perfect… Until the Entire Team Walked Out After Closing 11:36 SaaS Due Diligence Simplified – The 4 Metrics That Actually Matter 17:01 The KPI That Signals It’s Time to Sell (Before the Business Declines) 22:14 What NOT to Buy in the Age of AI – And Where the Real Moats Still Exist   Key Takeaways ➥ The best deals aren’t found - they’re filtered. Without a clear acquisition thesis, you’ll chase instead of build. ➥ If the business can’t run without the founder, you didn’t buy an asset - you bought a job. ➥ The real cost isn’t the purchase price. It’s the capital required to grow the business after you own it. ➥ Conversion rate and churn will tell you the truth before revenue ever does - watch them closely. ➥ AI is lowering the barrier to entry. If your business can be easily copied, it’s already at risk. ➥ The biggest hidden upside in acquisitions is often an under-monetized audience. ➥ Most founders sell too late. The right time to exit is before growth starts getting harder.   About Kevin Peterson Kevin Petersen is a serial entrepreneur and founder of WebFolio Management, a portfolio vehicle that acquires and operates small SaaS companies on behalf of investors and himself.  Since getting started in the web-business market he has acquired dozens of internet businesses (including Picreel) and refined a deliberate, metrics-driven approach to sourcing, cleaning financials, and scaling recurring-revenue products.  Kevin focuses on building investor-grade units with clean books and repeatable growth processes, then deciding whether to hold, scale, or exit.  He frequently coaches other buyers and investors on building SaaS portfolios, and his playbook centers on deliberate deal selection, clean financial segmentation, and operational systems that allow multiple assets to be managed without chaos.    Connect with Kevin Peterson ➥ https://www.linkedin.com/in/kevinpetersen1/ ➥saastermind.net 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 founders think selling a business is about getting the highest offer. Nathan Gwilliam spent 30 years learning why that belief is exactly what destroys exits. Three businesses built. Three exits are closed. And a front-row seat to some of the most painful – and profitable – lessons the entrepreneurial world rarely talks about out loud. Like the time Disney came knocking... and his partner wouldn't even let them see the financials. Or the earn-out that looked like a windfall on paper - until someone else was making all the decisions. Or the phone call on a Sunday morning, right before church, that changed everything about why he sold Adoption.com. In this episode, Jaryd sits down with Nathan – the founder behind the most visited adoption platform in the world – for one of the most honest, human, and genuinely surprising conversations we've had on this show. Because yes, you'll get the tactics. The roll-up acquisition strategy that turned his biggest competitor into his biggest asset. The 50/50 partnership trap that quietly kills deals before they ever start. The exact moment a founder should seriously consider selling – even if the timing feels wrong. But this one goes somewhere most business podcasts are too scared to go. Into the Sunday morning phone calls. Into making decisions from love instead of fear. Into what it actually costs – emotionally, financially, spiritually – to build something real and then let it go. Nathan doesn't dress it up. He doesn't hide the mistakes. And he doesn't pretend the journey was clean. And that's exactly what makes this one unmissable. 🎧 Hit play. This is the exit conversation nobody else is having. BONUS: Get a free 30-day trial of Nathan's all-in-one podcasting platform at PodUp, or head to podallies.com to book a free 45-minute podcast strategy session – directly with Nathan himself.     Episode Highlights 07:08 The $100 Million Yahoo Offer That Got Turned Down – And the Company That Was Dead 12 Months Later 10:31 The Sunday Morning Phone Call That Changed Everything About Why He Sold Adoption.com 15:00 How Nathan Bought His Biggest Competitor Without a Single Dollar Down 18:21 Built From Scratch in 24 Months – Then Disney Tried to Buy It 23:06 The Earn-Out Trap: Why Nathan Would Walk Away From Millions Before He'd Ever Sign One Again 27:17 The 18x EBITDA Offer a Partner Killed Before Negotiations Even Started 27:52 Why a 50/50 Partnership Is Quietly the Most Dangerous Deal Structure in Business 34:00 Love-Based vs Fear-Based Decisions – The Framework That Changed How Nathan Runs Everything 37:02 How Nathan Turned His Biggest Competitor Into His Biggest Asset (Without Paying Upfront) Key Takeaways ➥ When your business is worth more to someone else than it is to you - that's your signal to sell. ➥ Never sign an earn-out where the buyer makes all the decisions. You're handing them your money and your future in the same handshake. ➥ A 50/50 partnership sounds fair until you need to make a decision that actually matters. ➥ Your biggest competitor might be your best acquisition – buy them, absorb their traffic, and stop splitting the market. ➥ The best acquisitions don't require a big upfront payment – structure it right and the asset pays for itself. ➥ Businesses don't always go up. The founders who wait for the perfect moment often end up selling at the worst one. ➥ Brokers create competition. Competition creates leverage. Never negotiate a major exit one-on-one if you can avoid it. ➥ Lead with genuine value and build revenue around it – the freemium model is still one of the most powerful plays in digital business. ➥ The best business decisions aren't made from fear. They're made from love – for your partners, your customers, and the impact you're trying to create.     About Nathan Gwilliam Nathan Gwilliam is a serial entrepreneur who has created and sold three digital ventures, including Adoption.com, the world’s most visited adoption platform. He grew major online communities and digital properties, and later sold Adoption.com to the Gladney Center for Adoption. Today he leads PodUp, an all-in-one podcasting platform that recently raised significant funding. Nathan’s unique journey – building, scaling, selling and reinventing digital businesses – gives him deep insight into acquisitions, growth strategy, and what it REALLY takes to exit for maximum value.   Connect with Nathan Gwilliam ➥ https://podup.com/  ➥ https://podallies.com/    ➥ https://www.linkedin.com/in/nathangwilliam/    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 does it actually look like to buy a business with zero margin for error? No safety net. No backup plan. A full-time military career, seven kids at home, and a lender who pulled out mid-deal. That's exactly where Michael Simpson found himself. In this episode, Jaryd Krause sits down with Michael Simpson - a National Guard serviceman who bought an 18-year-old e-commerce business using SBA financing, survived a near-collapse due diligence process, and came out the other side with a real, running business. But he's not here to tell you it was amazing. He's here to tell you the truth. Here's what's covered: 🏦 How he lost his SBA lender mid-transaction - and saved the deal in 48 hours 💀 The post-closing liquidity trap that blindsides almost every first-time buyer 😬 Why buying slightly bigger might have changed everything 📈 The unglamorous growth playbook keeping a 20-year-old business moving forward This isn't a success story wrapped in a bow. It's something far more valuable - an honest account of what buying a business really costs you. In money, stress, and lessons you can't learn anywhere else. If you're thinking about buying your first business, this might be the most important episode you listen to all year. 🎧 Hit play. Real talk only.   Episode Highlights 13:32 The SBA Pre-Approval Myth That Almost Derailed the Deal 16:15 Lender Drops Out Mid-Deal - How Michael Scrambled and Saved It in 48 Hours 19:48 The $10,000 Non-Refundable Move That Kept the Seller at the Table 21:25 The 100-Hour Business Plan That Stunned Bankers on Million-Dollar Deals 27:58 The $30,000 Tech Migration Mistake That Still Haunts Him 33:45 The Post-Closing Liquidity Trap That Catches First-Time Buyers Off Guard 35:49 Why He Had to Stop Paying Himself -  And Go Back to Work Anyway 36:27 The Brutal Truth About Buying Too Small (And What He'd Do Differently)   Key Takeaways ➥ "SBA pre-approved" listings are a marketing tactic - the real approval depends on YOU as the buyer, not just the business. ➥ Losing a lender mid-deal isn't fatal - having two banks compete for your business can actually get you a better outcome. ➥ A non-refundable deposit signals serious intent and can keep a seller loyal to you when the deal gets rocky. ➥ Post-closing liquidity is the number most first-time buyers forget - 10% down is just the starting line, not the finish. ➥ Buying too small is a trap - if the business can't cover debt service, pay for growth, AND pay you, you'll end up working for free. ➥ A obsessively detailed business plan doesn't just impress lenders - it becomes your single biggest competitive advantage in a crowded deal. ➥ Technical debt is invisible until you own it - always pressure-test the tech stack before you sign, not after. ➥ Boring, stable, decades-old businesses with loyal customer bases consistently outperform shiny, high-growth ones for first-time buyers. ➥ The real cost of buying a business isn't the purchase price - it's everything that comes after the wire transfer hits.   About Michael Simpson Michael Simpson is a business owner, acquisition entrepreneur, and National Guard serviceman who successfully bought a business using SBA financing while balancing a full-time military role and raising seven children.  His acquisition journey included a near-deal-ending due diligence process and the challenge of replacing his SBA lender mid-transaction. Michael brings a rare, real-world perspective on resilience, risk management, and executing an acquisition under extreme personal and financial pressure.   Connect with Michael Simpson ➥ https://x.com/Michael_in_biz    ➥ https://www.discountcatholicproducts.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 thing standing between you and total lifestyle freedom… was just one business acquisition? A former respiratory therapist and a software developer – no entrepreneurial experience, no roadmap, no idea what they were doing – decided to bet on themselves anyway. And now? They're running a lean team of 11 VAs from wherever in the world they feel like being that week. Guatemala last month. St. Kitts for their anniversary. Belize next. You get the picture. In this episode, Jaryd Krause sits down with Alan and Mel, a husband-and-wife duo who tried every side hustle in the book – financial lending, credit repair, online teaching – before discovering that buying an existing online business was the shortcut they'd been exhausting themselves looking for. They used SBA financing to acquire a $1.2M business with just $65K out of pocket. They inherited 2 VAs and a chaotic operation. They were working 60-hour weeks at the start. And then – systematically, strategically – they rebuilt it, scaled it, and sold it. Profitably. Now they're already under LOI for their next deal. Here's what makes their story different though. Neither of them had ever owned a business before. One was in healthcare. One was in tech but still didn't think you could buy something you couldn't physically touch. They were scared, skeptical, and figuring it out in real time. Sound familiar? If you've ever wondered whether someone like YOU could actually pull this off – this episode is your answer. Hit play. You'll want to hear this one.🎧   Episode Highlights 06:09 The $0 Down Deal Structure Most Buyers Don't Even Know Is Possible 15:13 How They Bought a $1.2M Business With Just $65K Out of Pocket 18:26 Why Taking 6 Months to Close Was the Smartest Thing They Ever Did 24:09 From 60-Hour Weeks to 5: The Exact Strategy They Used to Replace Themselves 29:00 The Layoff That Forced Them All In – And Accidentally Changed Their Lives Forever 33:33 They Sold the Business… and Got Bored in Two Months. Here's Why They're Back 35:33 The Raw Truth About Mindset That Most Business Coaches Are Too Polished to Say 42:12 The Wealth Loop Nobody Talks About: How One Business Funded an Entire Real Estate Portfolio   Key Takeaways ➥ You don't need industry experience to acquire a business – the learning happens after you buy, not before. ➥ SBA financing can get you into a $1.2M business with as little as $0 down if you negotiate the deal structure right. ➥ The fastest way to scale an acquisition is to document every bottleneck, then hire to eliminate them one by one. ➥ A longer closing timeline isn't a red flag – it's free due diligence that lets you watch the business perform before you own it. ➥ The moment you stop working IN the business and start building a team around it, everything changes. ➥ Buying a business where the owner is burned out is a hidden goldmine – lower price, massive upside, ready to scale. ➥ Online businesses have no glass ceiling – unlike physical businesses, growth isn't limited by location, rooms, or geography. ➥ Business cash flow funds real estate. Real estate equity funds the next acquisition. That loop, repeated, builds serious wealth. ➥ Mindset isn't a buzzword here – it's the actual difference between people who pull the trigger and people who stay stuck researching forever. ➥ Freedom isn't something you find after you build the business. It's something you design into the business from the start.   About Alan & Mel Alan and Mell are a husband-and-wife duo who’ve turned online business acquisitions into a lifestyle of freedom and adventure. Alan, with a background in education and technology, and Mel, a former respiratory therapist with an MBA from Ohio State’s Fisher College of Business, combined their skills to acquire three online businesses—recently exiting one successfully. Their profits helped them purchase two Airbnb properties and build a third in Belize. Thanks to the flexibility of their online ventures, they recently spent a month in Guatemala and El Salvador with their daughters for a World School program. Now, they’re under LOI for their next deal and on track to acquire three new deals within the next year.   Connect with Alan & Mel ➥ https://risingphoenixfund.org/home ➥ AI content creation platform: https://wordgenius.ai/   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 buyers are still doing due diligence like it's 2015. And the ones who know how to use AI? They're finding better deals, faster, and you'd never even know they were looking. In this episode, Jaryd sits down with Haytham Allos, M&A strategist, AI specialist, and one of the minds behind one of the world's first AI-powered law firms, to pull back the curtain on what's actually happening right now at the intersection of artificial intelligence and buying businesses. And it gets wild. We're talking AI agents that evaluate deals. Smart contracts that close them. Fractionalised ownership that lets someone invest in a business for as little as $50. A future where your AI agent negotiates with the seller's AI agent, and a human just says yes or no at the end. But before we get there? Haytham breaks down what's happening right now. Why most buyers are still flying blind, why AI without the right prompting is actually dangerous in a deal, and the one thing that kills more mergers than bad financials ever will. You'll discover why prompt engineering is the most underrated skill in acquisitions today, how to use AI to get an unfair edge in due diligence without replacing your gut instinct, and exactly where the smart money is already moving. This isn't theory. This is where M&A is heading, and the buyers who understand it now are going to own the next decade. Hit play. Your competition probably already has. 🎧   Episode Highlights 05:45 The Chainsaw Analogy: Why AI Without Experience Is Genuinely Dangerous in a Deal 09:08 The Hallucination Problem: Why AI Can Lie to You During a Deal and How to Stop It 13:57 Where AI Creates the Biggest Unfair Advantage in the Acquisition Process Right Now 16:43 Prompt Engineering: The Most Underrated Skill Every Serious Buyer Needs to Master 19:44 The Rise of Agent-First Companies: What Cursor AI's $2 Billion Valuation Tells Us About the Future 22:31 The Mindset Shift Every Business Owner Must Make or Get Left Behind 28:16 AI Agents Buying From AI Agents: The Future of M&A Is Closer Than You Think 31:12 Smart Contracts, Crypto Wallets and the Death of Bureaucratic Deal Making 35:43 Fractionalised Business Ownership: How Anyone Could Invest in a Business for $50   Key Takeaways ➥ AI without experience is like handing a chainsaw to someone who's never cut down a tree. Powerful tool. Dangerous hands. ➥ AI will hallucinate during your due diligence. If you don't know how to configure it correctly, it will confidently lie to you about the business you're about to buy. ➥ Prompt engineering is the most underrated skill in acquisitions right now. The quality of your questions determines the quality of your deal. ➥ The number one reason mergers fail isn't bad financials. It's people, politics, and ego. AI is quietly removing all three from the equation. ➥ We are shifting from AI that answers questions to AI that takes actions. The buyers who understand that difference right now will have an unfair advantage for the next decade. ➥ Smart contracts, crypto wallets, and blockchain are about to collapse the layers of bureaucracy that slow every deal down. The merger process, as we know it is on borrowed time. ➥ Fractionalised ownership is coming to business acquisitions. You won't need six figures to get into a deal. You'll need the right agent and the right wallet. ➥ The future of M&A is two AI agents negotiating a deal, presenting it to their humans, and closing it on the blockchain before a bank even answers the phone.   About Haytham Allos Haytham Allos is an M&A and AI strategist focused on how artificial intelligence is transforming the buy-side deal process. He works at the intersection of technology, data, and acquisitions, helping investors and acquirers use AI to enhance due diligence, identify hidden risks, and make better capital allocation decisions.  Haytham specializes in applying AI tools across deal sourcing, financial analysis, operational review, and post-acquisition decision-making.   Connect with Haytham Allos ➥ https://vikk.ai/ ➥ https://finance.yahoo.com/news/vikk-ai-selected-prestigious-aws-141700773.html?guccounter=1   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.

Buying a $10M–$100M online business isn’t just about having capital. It’s about relationships, structure, leverage, and knowing how the game is really played behind closed doors. In this episode, Jaryd Krause sits down with Emmet Kilduff, founder of The Fortia Group and former investment banker at Morgan Stanley, to unpack how serious online acquisitions actually get done in the $10M to $100M range. After 25 years in M&A, Emmet pulls back the curtain on what separates institutional buyers from everyday acquirers, and why trying to “figure it out yourself” is one of the most expensive mistakes you can make. You’ll learn: The 3-stage “Flirt, Date, Marry” framework elite dealmakers use to build acquisition relationships years before a deal closes Why the best buyers pitch sellers, and how to create a buyer deck that makes founders want you The real funding structures used by strategics, private equity, aggregators, and search funds What’s changed since the 2021 acquisition boom, and why 100% upfront deals are basically extinct The truth about earn-outs (and why most are designed for buyers, not sellers) Why recurring revenue businesses command premium multiples, and how valuation arbitrage actually works How to transition from operator to owner so you can think strategically and fund bigger moves This is not theory. This is how real capital allocators think. If you want to understand how serious acquirers finance deals, structure terms, protect downside, and build relationships that lead to eight- and nine-figure exits, this episode is your behind-the-scenes briefing. If you’re planning to buy, sell, or scale an online business and want to understand how institutional-level M&A actually works, hit the “Play” button.   Episode Highlights 03:12 Why Even $10M Buyers Shouldn’t Go It Alone 05:08 The “Flirt, Date, Marry” Framework for Closing Bigger Deals 08:41 How Smart Buyers Pitch Sellers (And Win Trust Fast) 12:06 The Truth About Earn-Outs (And Why Sellers Should Be Careful) 18:47 The Three Types of Institutional Buyers in the $10M–$100M Range 23:55 Why Recurring Revenue Changes Everything in Valuation 28:36 The Strategic Conversations That Should Happen Before Price Is Discussed 35:44 From Operator to Owner: Making the Shift to Strategic Thinking 40:27 Building an Advisory Board That Actually Moves the Needle Key Takeaways ➥ Buying a $10M–$100M online business is as much about relationships and strategy as it is about money. ➥ Use the “Flirt, Date, Marry” framework: build trust early, share information progressively, and finalize only when both sides are aligned. ➥ Strong buyers actively pitch sellers—your experience, vision, and team matter just as much as your capital. ➥ Typical deal structures include 60–80% upfront with the balance via earn-outs, equity rollover, or milestone-based deferred payments. ➥ Structuring earn-outs around revenue, not profit, reduces disputes and protects long-term relationships. ➥ Recurring revenue businesses (SaaS, subscriptions, memberships) command higher multiples and offer more predictable financing. ➥ Advisory panels and mentors accelerate decision-making, reduce risk, and boost credibility with sellers. ➥ Transitioning from operator to owner requires delegation, trust, and strategic focus over day-to-day management. ➥ Patience, preparation, and network-building are the hidden factors that make or break acquisition success.   About Emmet Kilduff Emmet Kilduff is the Founder of The Fortia Group, an M&A advisory firm specializing in the sale of eCommerce brands and digital agencies. With a background at leading Wall Street investment banks including Morgan Stanley, Emmet brings institutional-level M&A, valuation, and deal-structuring expertise to small and mid-market online businesses.  Through Fortia, he has advised founders, buyers, and investors on acquisitions across the UK, US, and international markets, helping them navigate financing, positioning, and exits with professional rigor.  On this episode of the Buying Online Businesses Podcast, Emmet shares how sophisticated buyers think about funding acquisitions, structuring deals, and avoiding the common mistakes that derail first-time online business buyers.   Connect with Emmet Kilduff ➥ https://www.linkedin.com/in/emmettkilduff/ ➥ https://thefortiagroup.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.

Online business acquisitions aren’t won by the highest bidder - and they’re definitely not lost for the reasons most buyers think. In this episode of the BOB Podcast, Jaryd Krause sits down with Ryan Condik - serial entrepreneur, M&A advisor at Quiet Light, and founder of Let’s Buy a Business - to unpack what actually determines who wins (and who loses) in competitive acquisition processes. Most buyers assume it all comes down to price. Just offer more and you win, right? Not exactly. In real-world M&A, things like certainty, speed, positioning, and creativity often matter more than a bigger number. Ryan shares behind-the-scenes stories from competitive deals, including why some buyers lost over small term differences, how one buyer won simply by building a genuine relationship with the seller, and why “certainty of close” can be far more powerful than offering an extra 10%. You’ll learn: Why sellers often choose lower offers - and what they’re really evaluating How certainty, speed, and clean deal structures give buyers a serious edge Why trust and relationships can outweigh valuation The common buyer mistakes that quietly kill deals How creative structuring (including equity rollovers) can change the outcome Why knowing your value-add before submitting an LOI shifts the entire negotiation Whether you’re buying your first online business or competing for premium assets in a crowded market, this episode breaks down what separates serious acquirers from hopeful bidders. In M&A, price gets attention - but certainty wins deals. 🎧 Hit play to learn how to position yourself as the buyer sellers actually want to choose.   Episode Highlights 02:53 Why Chasing Billions Is a Trap (And What Actually Builds Freedom) 12:42 The “Seasons of Life” Framework for Smarter Entrepreneurship 18:02 The Two-Way Door Rule: How Elite Entrepreneurs Make Fast, Confident Decisions 20:17 Why Most Aspiring Entrepreneurs Fail Before They Even Start 24:34 The #1 Mistake Buyers Make When Acquiring a Business 26:24 Why Most Buyers Lose Deals (And Don’t Even Know Why) 28:46 The $400 Move That Won a Multi-Million Dollar Deal 30:45 How Relationships Beat Higher Offers in Competitive M&A 32:04 The 10% Lower Offer That Still Won the Deal 35:45 SBA Buyers vs. Serious Buyers: What Sellers Actually Want 37:38 When Paying MORE Is the Smartest Financial Decision 40:01 How to Know When You’ve Found “The One” (And Go All In) 43:00 AI, Adaptation & Why Average Operators Will Get Left Behind   Key Takeaways ➥ Traditional SEO is still the foundation—AI and GEO optimization enhance it rather than replace it. ➥ Strong brand presence and mentions across multiple platforms are now more important than backlinks for AI visibility. ➥ Being associated with reputable brands or industry leaders boosts authority and trust in AI-driven results. ➥ Content hubs and semantically related pages improve AI discoverability more than focusing on keywords alone. ➥ Social media, forums, and niche communities (Reddit, Medium, Facebook Groups) contribute to AI recognition. ➥ Balance is key: optimize for AI while maintaining usability and experience for human visitors. ➥ AI content generators can efficiently create research-backed, brand-aligned, and contextually rich content.   About Ryan Condie Ryan Condie is a serial entrepreneur, M&A advisor and founder behind Let’s Buy a Business. He has built, bought, and sold multiple digital ventures including RentLingo via a successful acquisition. He now helps founders master deals, due diligence and exits. Ryan also serves as an advisor at Quiet Light Brokerage, where he guides buyers and sellers through evaluations, negotiations and growth opportunities that maximize exit value. His experience blends real-world deal execution with deep strategic insight.    Connect with Ryan Condie ➥ https://ryancondie.com/ ➥ https://www.letsbuyabusiness.com/   Other podcasts with Ryan; https://buyingonlinebusinesses.com/ep-149-why-buy-a-profitable-online-business-instead-of-staring-one-with-ryan-condie-part-1/ https://buyingonlinebusinesses.com/ep-150-title-how-to-get-started-buying-profitable-online-business-with-ryan-condie-part-2/   https://www.youtube.com/watch?v=hRv7UHDUjYA     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.

The internet isn’t being searched the same way anymore—and most businesses haven’t caught up. In this episode of the BOB Podcast, Jaryd Krause welcomes back Rad Paluszak to explore the transition from SEO to GEO (Generative Engine Optimization) and what it means for founders, operators, and investors navigating an AI-driven world. Instead of ranking pages, AI answer engines are ranking entities, brands, and trust. Rad explains why traditional SEO playbooks are breaking down, how AI engines source and rotate answers, and why brand mentions across the web now matter more than links ever did. You’ll learn: Why AI engines rarely repeat the same sources—and how that changes traffic forever How brand authority is built through mentions, associations, and personal brands Why being listed alongside established brands can instantly elevate visibility The growing role of Reddit, social platforms, and communities in AI discovery How to structure content for AI without sacrificing real users What businesses should stop obsessing over—and what actually moves the needle Whether you run content-heavy sites, ecommerce brands, SaaS, or are evaluating businesses to buy, this episode offers a practical framework for adapting to AI without panic—or guesswork. AI is coming either way.The question is whether your brand will be visible when it does. 🎧 Hit play and learn how to stay visible before the rules change completely.     Episode Highlights 03:10 Pivoting from SEO to GEO: How AI is Changing the Search Landscape 06:00 The Growing Importance of Brand Mentions and Broad Visibility 10:00 Leveraging Listicles, Social Media, and Mentions for Authority 14:00 Optimizing Websites for AI Agents vs. Human Users 18:00 Content Strategy for AI: Hubs, Semantic Relevance, and Queries 22:00 Auditing Your Site and Competitors for AI Visibility 24:00 Using AI Tools: Visibility Reports and Content Generators 29:00 Incorporating Brand Voice, Contextual Images, and Internal Linking 32:57 Scaling Your Business with AI-Driven Content Strategies   Key Takeaways ➥ Traditional SEO is still the foundation—AI and GEO optimization enhance it rather than replace it. ➥ Strong brand presence and mentions across multiple platforms are now more important than backlinks for AI visibility. ➥ Being associated with reputable brands or industry leaders boosts authority and trust in AI-driven results. ➥ Content hubs and semantically related pages improve AI discoverability more than focusing on keywords alone. ➥ Social media, forums, and niche communities (Reddit, Medium, Facebook Groups) contribute to AI recognition. ➥ Balance is key: optimize for AI while maintaining usability and experience for human visitors. ➥ AI content generators can efficiently create research-backed, brand-aligned, and contextually rich content.   About Rad Paluszak Rad Paluszak is a digital marketing and SEO strategist focused on AI search, Generative Engine Optimization (GEO), and brand visibility in an AI-first internet. He helps businesses adapt beyond traditional rankings by optimizing for brand authority, entity mentions, and AI discovery across Google, ChatGPT, and social platforms. Rad specializes in visibility audits, content strategy, and future-proofing brands for generative search   Resource Links ➥ Ordering PROMO content packages (1 Free + 10 articles with images, internal linking and brand voice included): https://order.non.agency/content?referral_code=Buying_Online_Businesses ➥ Free AI Visibility Report: https://non.agency/en/service/ai-search-optimization-aio/?referral_code=Buying_Online_Businesses#ai_visibility ➥ 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.

Getting finance to buy an online business is no longer just about ticking boxes or relying on outdated bank formulas. Today, lenders are looking forward. They want to understand your assumptions, your go-to-market strategy, and how the business performs once capital is deployed. In this special episode, Jaryd Krause speaks with Ciaran Burke, COO and co-founder of Swoop, a global SME funding marketplace helping buyers access debt, equity, and grant funding across the UK, Australia, the US, and Canada. Ciaran has helped thousands of businesses secure funding by unlocking options traditional banks often miss. You’ll learn how buyers are funding ecommerce, SaaS, and media acquisitions, what lenders really care about beyond the numbers, and why acquisition finance is now easier to access in markets like Australia and the UK. If you are planning to buy an online business and want to understand how deals are being funded right now, hit the “Play” button!  BONUS: Explore Swoop’s free funding platform and see if your next acquisition qualifies.   Episode Highlights 06:00 Funding Options for Acquiring Online Businesses 09:02 Understanding Deposit Requirements for Acquisitions 12:05 Setting Up a Business Entity for Acquisition Financing 15:03 Navigating Interest Rates and Loan Terms 18:02 Refinancing and Its Importance for Business Owners 21:02 Key Requirements for Loan Approval 24:38 Navigating the Financing Landscape 30:00 Preparing for Acquisition: Key Documentation 36:03 Understanding the Acquisition Process 40:01 Exploring Financing Options and Strategies 43:53 The Importance of Credit and Sector Awareness   Key Takeaways ➥ The Australian market was targeted for expansion during COVID due to its strong SME financing landscape. ➥ Deposits for acquisitions can vary significantly based on the business type and trading history. ➥ New investors may need to provide a higher deposit compared to those with established businesses. ➥ A solid business plan and financial model are crucial for securing financing. ➥ Interest rates and loan terms can vary widely based on market conditions and business performance. ➥ Refinancing options can improve cash flow and reduce interest rates over time. Understanding personal credit scores is essential for first-time investors.   About Ciaran Burke Ciarán Burke is the COO & Co-Founder of Swoop, a global SME funding marketplace that helps businesses discover debt, equity, and grant options using integrated business data.He co-founded Swoop after a career at KPMG and building the creative network Hiive, and now leads the product & operations work that matches businesses with suitable finance solutions across multiple territories. Swoop’s platform has helped hundreds of thousands of businesses access funding and simplify options that traditional banks often miss, making it a powerful route for buyers who need acquisition capital. Ciarán frequently speaks about debt, equity, and grants to fund acquisitions in the UK, Australia, and the US.   Join Swoop Funding for free; ➥ https://swoopfunding.com/au/buying_online_businesses   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.

In this solo episode, Jaryd Krause dives into a topic that quietly shapes success more than most people realize: relationships. While many know him for his business insights, fewer are aware of how deeply spiritual his personal development journey has been and how much those “non-traditional” practices have contributed to his financial and professional success. With nearly three decades of inner work and growth behind him, Jaryd shares what he typically teaches behind closed doors to paid clients. Lately, one theme has been impossible to ignore: the profound impact relationships have on wealth, confidence, and expansion. He explores how most people have three to five close relationships: family, partners, friends, or colleagues that unintentionally stifle their growth. Check out the full episode to uncover the relationship dynamics that may be quietly holding you back—and learn how to break free from them.   Episode Highlights 02:44 The Impact of Relationships on Wealth 05:41 Family Dynamics and Financial Mindsets 07:54 Navigating Friendships and Financial Advice 10:44 The Role of Intimate Relationships in Personal Growth 21:34 The Impact of Relationships on Personal Growth 26:46 Navigating Friendships and Family Dynamics 32:20 Auditing Relationships for Abundance 37:29 Re-engineering Identity Through Social Circles 42:21 Actionable Steps for Relationship Management   Key Takeaways ➥ Spiritual practices contribute significantly to business success. ➥ Relationships can unconsciously stifle personal growth and abundance. ➥ Family conditioning often instills a scarcity mindset. ➥ It's crucial to audit your relationships regularly. ➥ Intimate partners can influence your ambition and success. ➥ Friendships should be evaluated based on their alignment with your goals. 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 does it really take to acquire 26 SaaS businesses—and keep them growing? In this episode, Jaryd Krause sits down with SaaS M&A professional Guillaume Lussato for a behind-the-scenes look at how successful software acquisitions actually happen. Guillaume breaks down his unconventional path from software sales at a cybersecurity company to sourcing and closing deals at Constellation Software, one of the most disciplined acquirers in the SaaS world. Guillaume reveals why the best SaaS acquisitions aren’t rushed deals but relationships built over years. He shares how patience, credibility, and consistent founder outreach led to his first acquisition at SaaS Group—a low-profile digital calendar tool called DacBoard—and why targeting under-the-radar SaaS companies can unlock outsized opportunities. The conversation dives deep into today’s hyper-competitive M&A environment, including how to stand out when every founder is being pitched. Guillaume unpacks the red flags most buyers miss, from risky customer concentration to weak net dollar retention, and explains SaaS Group’s clear acquisition framework—capital-efficient, product-led growth businesses with strong fundamentals. The episode wraps with a powerful discussion on how to balance organic growth with acquisitions, avoid overextension, and make smarter strategic decisions when scaling a portfolio of software companies. If you’re serious about SaaS acquisitions, this episode is a must-watch. Click through and watch the full video to learn exactly how Guillaume evaluates, sources, and scales SaaS businesses.   Episode Highlights 02:52 Transition from Sales to M&A Origination 05:52 The Art of Deal Sourcing 09:04 Evaluating Founders and Their Businesses 11:47 Understanding Acquisition Criteria 15:10 Growth Strategies: M&A vs. Organic Growth 18:00 Identifying Red Flags in Due Diligence 21:06 Navigating Operational Complexity 23:57 AI Risks and Opportunities in Software 27:06 Balancing Capital Allocation and Diversification   Key Takeaways ➥ You need to build relationships, build trust, build credibility. ➥ It can take a really long time to acquire a business. ➥ We try to identify red flags as early as possible. ➥ We don't manage our portfolio through spreadsheets; we're not finance people. ➥ Should we buy it? Why? For how much?   About Guillaume Lussato Guillaume Lussato is a senior business development and M&A professional at saas.group, where he helps identify, acquire and scale profitable B2B SaaS companies. He hosts discussions on SaaS M&A, growth, and founder transitions and frequently speaks at industry events about how to grow without VC and what makes SaaS acquisitions succeed or fail. Guillaume focuses on sourcing deals, operational playbooks for scaling post-acquisition, and practical insights that matter to anyone buying online businesses to replace income, scale a portfolio, or prepare for exits.   Connect with Guillaume Lussato ➥ https://www.linkedin.com/in/guillaumelussato/   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 happens when a seasoned real estate investor steps away from physical property and into the world of digital acquisitions? In this episode, we sit down with Julien Jacques, who made the bold transition from building a real estate portfolio to acquiring online businesses—uncovering both the opportunities and the unexpected mistakes along the way. Julien shares his transparent journey, including his non-traditional Canadian financing strategies, the specific digital business models he targets, and the hard-earned “humble realist” lessons that came from both successful acquisitions and costly missteps. Whether you’re managing rental properties, exploring your first acquisition, or curious about “online real estate,” this conversation delivers a grounded, experience-driven look at what it truly takes to scale in the digital business landscape. Ready to rethink how you build wealth beyond physical assets?  Watch the full episode now!   Episode Highlights 10:51 Lessons Learned in Acquisition 13:28 The Importance of Relationships in Business 16:16 Structuring the Deal 21:01 Navigating Business Financing and Debt 22:11 The Dangers of Overdue Diligence 25:25 Making Decisions with Incomplete Information 29:45 Lessons from a Business Acquisition Failure 36:12 The Importance of Leadership and Networking 40:41 The Journey of an Entrepreneur: Risks and Rewards   Key Takeaways ➥ Real estate can provide passive income but requires management. ➥ Buying an existing business can be less risky than starting from scratch. ➥ Due diligence is important but can be misleading if overanalyzed. ➥ Networking is crucial for entrepreneurial success. ➥ Entrepreneurship requires resilience and adaptability.   About Julien Jacques Julien Jacques is a former real-estate investor and entrepreneur who pivoted into buying online businesses after a year-and-a-half of searching across franchises, retail, and other opportunities. He now owns Rocket Powered Sound, a digital products e-commerce business selling sample packs to music producers, and has firsthand experience in financing, acquiring, and scaling an online company in Canada. Julien’s practical transition from physical assets to “online real estate” gives him a unique perspective on acquisition due diligence, margin dynamics in digital products, and how to turn acquisition opportunities into reliable income streams.   Connect with Julien Jacques ➥ https://www.linkedin.com/in/juljacques/    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 really kills business deals—without anyone noticing? Not the obvious red flags.Not the spreadsheets.But the quiet mistakes buyers make the moment they think they’ve already won. In this episode, Jaryd Krause sits down with John Martinka (aka The Escape Artist), who’s spent 25+ years advising buyers and sellers across 150+ real acquisitions. No theory. Just what actually happens in deals. You’ll hear why first-time buyers fall in love too fast, how stopping your search early weakens your position, and why relationships matter more than price once negotiations get serious. John also reveals how “great on paper” deals quietly turn into long-term stress, and what to do instead. Plus, what happens after the deal closes: how one small shift helped a buyer grow a business by 75% in under a year, and why growth often fixes problems faster than perfection ever will. If you’re buying a business (or even thinking about it), this episode will change how you see deals before it’s too late. 👉 Watch the full video now and get tips most buyers only learn the hard way.   Episode Highlights 02:45 – Buyer fever explained: why first-time buyers knowingly overpay—and how emotional attachment kills financing and post-close cash flow. 04:10 – Why stopping your search early weakens leverage, increases emotional risk, and makes buyers over-commit before a deal is real. 05:58 – A real $6M deal case study: how choosing the highest offer over the right buyer led to 12+ months of post-close disputes and massive stress costs. 10:05 – Why most deals do close after LOI—and the specific conditions that still quietly cause failures during diligence. 11:20 – Add-backs red flags: why too many adjustments signal risk, credibility issues, and potential tax exposure. 18:10 – Seller priorities revealed: why 90%+ of sellers care more about employee outcomes and legacy than price alone. 21:40 – Earn-outs unpacked: why earn-outs fail when used to justify overpricing—and when they actually make sense. 28:30 – How one compensation change drove 75% revenue growth in under 12 months after acquisition.   Key Takeaways ➥ Don’t fall in love with a business before due diligence. Emotional attachment (“buyer fever”) can lead to overpaying and unrealistic expectations. ➥ Keep your options open. Continuing your search until closing strengthens negotiating power and reduces risk. ➥ Choose the right buyer or seller over the highest price. Alignment of values, motivation, and vision prevents long-term disputes and stress. ➥ Customer concentration risk: Businesses with 2 customers generating ~60% of revenue are extremely vulnerable—loss of one client can collapse cash flow and valuation. ➥ Owner dependency is a hidden risk: Owners working 30–40+ hours per week without robust systems increase acquisition risk; businesses are more valuable when the owner can step away without disruption. ➥ Employee incentives drive growth. Strategic compensation and bonuses can unlock rapid revenue growth without heavy structural changes. ➥ Seller priorities often extend beyond money: Over 90% of sellers care about employee outcomes and business legacy as much—or more—than the final sale price.   About John Martinka John Martinka, known as The Escape Artist®, is a veteran M&A advisor and business strategist. As Co-Founder and Managing Member of Nokomis Advisory Services and Martinka Consulting, he’s guided over 150 business buy-sell transactions and analyzed more than 1,000 companies.  With more than 25 years of experience, John helps executives “escape” the corporate grind by buying businesses the right way, and he also coaches business owners to exit their companies with style, grace, and maximum value. He’s a prolific author (four business books) and speaker, passionate about reducing owner dependency, building systems, and setting up companies to scale or exit profitably.   Connect with John Martinka ➥ https://www.linkedin.com/in/johnmartinka/    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 don’t fail at buying a business because they’re not smart enough.They fail because—without realizing it—they’re setting themselves up to lose before they even begin. In this solo episode of the BOB podcast, Jaryd Krause goes off-script and gets brutally honest about the real reasons people struggle to acquire online businesses, and why these same patterns show up in money, business, and life. This isn’t a tactical “how-to” episode.It’s a mindset reset. Jaryd breaks down the five biggest reasons people fail at buying a business, drawing from his own journey, his work with buyers around the world, and the patterns he sees repeatedly derail otherwise capable people. You’ll learn: Why you don’t need to know how to run or buy a business before acquiring one How “good” advice becomes dangerous when you treat general guidance as personal truth Why most people are mentally unprepared for the acquisition process—even when they have the money How impatience and unrealistic timelines quietly sabotage deals The uncomfortable truth about why wanting a business isn’t enough—and when change only happens out of necessity Jaryd also dives into cultural differences, ambition, pain as a driver of success, and why some people push through every obstacle while others stall indefinitely. This episode is raw, reflective, and unapologetically real. 🎧 Listen in—and ask yourself whether you’re setting yourself up for success… or failure.   Episode Highlights 01:00 – Why most people unknowingly set themselves up for failure before they even start 06:55 – Myth-busting: Why you don’t need to know how to run or buy a business before acquiring one 10:45 – The danger of “bad” advice and why most guidance is general, not personal 13:55 – Why copying someone else’s timeline almost guarantees failure 18:30 – How unrealistic goals quietly destroy confidence and momentum 20:45 – The mental reality of buying a business and why most people aren’t prepared 24:30 – Patience vs. pressure: why counting inputs matters more than counting time 28:20 – Want vs. necessity: the single biggest reason people fail to follow through 32:40 – How pain, fear, and discomfort actually drive ambition and success   Key Takeaways ➥ You don’t need experience to get started. Most successful buyers had never run or bought a business before their first acquisition. Skills are built during the process—not before it. ➥ General advice becomes dangerous when taken as personal truth. What worked for someone else may not work for you due to differences in time, resources, credit, life stage, and risk tolerance. ➥ Unrealistic timelines create avoidable failure. Comparing your progress to others—or forcing artificial deadlines—leads to disappointment, self-doubt, and unnecessary quitting. ➥ Mental readiness matters more than capital. Buying a business requires patience, resilience, and the ability to handle rejection, uncertainty, and long stretches without visible progress. ➥ Preparation is psychological, not just financial. Due diligence, deal flow, and negotiations are mentally taxing—especially at lower price points where fewer systems and advisors exist. ➥ Stop measuring success by time. Measure inputs instead. Track actions like deals reviewed, conversations held, and due diligence completed. Progress compounds through consistent inputs, not arbitrary deadlines. ➥ Setting the bar too high too early damages confidence.  Low, achievable goals build momentum. Repeated “missed” goals—even small ones—erode belief and motivation over time. ➥ Wanting a better life isn’t enough—necessity creates action. True follow-through happens when change becomes non-negotiable, not optional. ➥ Pain and discomfort are powerful drivers, not problems. Ambition is often fueled by frustration, fear, or dissatisfaction. Learning to harness that energy is key to long-term success.  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.

How far can $100,000 really take you in business acquisitions? One deal?A small portfolio?Or a scalable acquisition machine? In this episode, Jaryd Krause sits down with SBA Business Development Officer Glenn Giro to break down the real math behind buying businesses with SBA financing, and why there’s technically no cap on how many businesses you can acquire, as long as you understand the rules that actually stop most buyers. They unpack how entrepreneurs are using up to 90% SBA financing, long 10-year terms, and no prepayment penalties to build portfolios most people assume are out of reach. You’ll discover: How $100,000 in cash can unlock a $1M+ acquisition The $5M SBA cap per NAICS code and how it impacts serial buyers Why banks love SBA loans (and why that matters to you) The real fees lenders don’t explain upfront How cash flow and debt service coverage are actually calculated What changes when you go from your first deal to your second, third, or fifth When 100% financing is possible and when it’s not Why do some high-multiple digital businesses get rejected The timeline lenders expect before approving your next acquisition If you’re serious about buying your first digital business or turning one deal into a portfolio of cash-flowing assets, this episode will completely reframe how you think about capital, leverage, and scale. Watch the full video to see the numbers, strategies, and acquisition pathways most buyers never learn about.   Episode Highlights 02:55 – Why a “simple” 10% down payment can still kill your SBA deal if you don’t understand total project costs. 05:08 – The harsh truth: why $100K is often not enough to safely buy a $1M business. 10:52 – How SBA’s 75% loan guarantee unlocks 90% financing—and why banks are eager to lend. 12:57 – The hidden cost most buyers miss: $20K–$30K in SBA fees on a $1M acquisition. 15:16 – The real reason most buyers can’t buy a second business right after their first. 23:59 – The quiet rule that caps portfolios at $5M per NAICS code—and how it blocks long-term scaling.   Key Takeaways ➥ SBA financing allows buyers to acquire businesses with as little as 10% down, but cash reserves and liquidity matter more than purchase price alone. ➥ The SBA’s 75% government guarantee reduces bank risk and unlocks long-term, high-leverage financing for profitable online businesses. ➥ Seller financing can help bridge equity gaps, but new rules requiring 10-year standby make it rare in competitive acquisitions. ➥ Most buyers need 6–12 months of successful operations before qualifying for a second SBA-backed acquisition—proof of execution accelerates approvals. ➥ Each business must support its own debt service; strong cash flow in one acquisition won’t compensate for a weak second deal. ➥ NAICS code limits quietly shape acquisition strategy—buyers who plan ahead can scale portfolios faster and avoid unexpected financing caps.   About Glenn Giro Glenn Giro is a seasoned SBA business development officer and acquisition financing expert who helps entrepreneurs buy and grow businesses using strategic SBA-backed loans. He hosts “SBA University,” a training series for business owners and aspiring acquirers, and regularly speaks about acquisition financing and business ownership strategies.   Connect with Glenn Giro ➥ https://www.linkedin.com/in/glenn-giro/➥ https://www.youtube.com/@SBAUniversity     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.

In this episode of the BOB Podcast, Jaryd Krause chats with David C. Barnett—author, educator, and all-around small-business acquisition pro. David’s spent 11 years making straightforward videos about buying, selling, and running small businesses, and he’s seen it all. They dive into what most first-time buyers totally miss—like how a “simple” service business pulling in $300–400k a year can still hit you with $10k in unexpected repairs, or how a business that seems hands-off can take up way more mental energy than you expect. You’ll hear things like: 💡 Why lifestyle buyers often crash and how to avoid turning your dream into a money trap⚠️ Even with a manager, some problems are just going to end up on your desk🔧 How one dry-cleaning shop kept a family afloat but still drained the owner mentally😬 What constant staff turnover really means—and the mindset that separates the quitters from the winners🧠 Why corporate experience doesn’t prepare you for small-business chaos📈 Why flipping businesses usually fails, but holding one for 5–6 years can pay off big🤝 Why you need real business friends, not just LinkedIn highlight reels David shares stories from owners who were totally blindsided by the day-to-day reality—turning neglected businesses into assets, and surviving the crazy, unexpected stuff along the way. 🎧 If you want the raw truth about buying a business—no fluff, just lessons you actually need—this episode’s for you.   Episode Highlights 07:07 – How overpaying and operational surprises can sink a business deal. 11:22 – The danger of buying based on emotion, not strategy. 15:30 – How “time on your side” strengthens your acquisition position. 20:15 – Fixing the “leaky bucket” of household finances before buying. 35:56 – Understanding your emotional drivers: lifestyle vs. self-actualization. 43:34 – Buying dreams vs. buying businesses: the B&B cautionary tale. 47:01 – Why running a business is harder than it looks: expectations vs. reality. 51:15 – The real value of small businesses is in long-term ownership, not flipping. 55:04 – Lessons from real owners: hiring struggles and the mindset of persistence.   Key Takeaways ➥ Know your motivation. Buying a business without understanding your emotional drivers — lifestyle, status, or security — can lead to overpaying or making misaligned choices. ➥ Cashflow and leverage are critical. Overpaying or using high leverage without accounting for operational costs and capital expenditure can sink even profitable businesses. ➥ Time is your ally. Build financial strength and patience first. A strong savings habit and a clear understanding of deals over time make you a stronger, less impulsive buyer. ➥ Due diligence saves you. Verify revenue, costs, and seller claims. Skipping checks or relying on emotion leads to costly mistakes. ➥ Lifestyle vs. business reality. Owning a business provides freedom and income, but it always carries operational burdens. Expect hands-on involvement, even with managers in place. ➥ Start with experience. Before buying a business in a new industry, work in it part-time. Real exposure prevents costly surprises. ➥ Value is in ownership, not flipping. Profit comes from running a business over years, not quick resale. Systems, marketing, and management improve long-term returns. ➥ Network with real business owners. Observing how experienced owners handle hiring, challenges, and growth teaches lessons no podcast or post can convey. About David Barnett David C. Barnett is a seasoned business broker, advisor, and educator who has helped aspiring entrepreneurs buy and sell small-to mid-sized businesses since 2009. He is the founder of the Business Buyer Advantage program—a comprehensive training system that guides buyers through finding, analysing, offering on, financing, and integrating a business. David’s background includes business valuation, deal structuring, and a passion for helping people escape the 9-to-5 by owning cash-flowing businesses.   Connect with David Barnett ➥ https://www.businessbuyeradvantage.com ➥ https://www.linkedin.com/in/davidbarnettmoncton    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.

He’s bought over 15 digital businesses—and learned some lessons the hard way. In this episode of the BOB Podcast, Jaryd Krause sits down with Yury Byalik, a seasoned growth marketer, acquisitions strategist, and digital-business investor who has spent over 15 years building, buying, and scaling profitable online companies. Currently serving as Head of Strategy & Acquisitions at Onfolio Holdings, Yury has mastered the art of spotting opportunities, structuring deals, and growing digital businesses into high-performing assets. But here’s the thing: acquisitions aren’t as simple as signing papers. Mistakes happen—and they can cost you time, money, and growth. Yury shares exactly what to avoid and what strategies actually work. In this episode, you’ll learn:💡 How Yury evaluates a digital business before buying🔧 The most common mistakes first-time acquirers make—and how to sidestep them📈 The growth strategies that turn a purchased business into a profitable, scalable asset🧠 The mindset needed to build a successful acquisition portfolio🤝 Practical tips on integration, operations, and making your acquisitions work together Whether you’re considering your first digital business purchase or looking to scale an existing portfolio, this episode is packed with actionable insights and real-world lessons from someone who’s actually done it—15 times over. 🎧 Plug in and get ready to avoid costly mistakes while accelerating your acquisition journey.   Episode Highlights 07:07 – Why a strong team and legal safeguards can make or break a deal. 09:06 – A shocking story of hidden fraud and non-disclosure. 15:05 – Roll-Up vs. Independent Growth: Yuri shares his selective approach to merging acquisitions 19:00 – Why high‑volume acquisition strategies (e.g., Amazon roll‑ups) often fail. 20:54 – Why waiting 1–3 months can save millions before scaling. 29:41 – How AI commoditization is reshaping valuations across industries.   Key Takeaways ➥ Due diligence is non‑negotiable. Many sellers omit or misrepresent critical information (clients leaving, illegal kickbacks, contract terms). Without a strong legal and analysis team, even “profitable” businesses can become liabilities post-acquisition. ➥ Diversification of traffic and revenue matters. Businesses dependent on a single channel (SEO, ads, Amazon, Google Adsense) are exposed to high risk — a single algorithm or platform change can destroy value. ➥ AI has fundamentally changed valuations. With AI tools reducing the uniqueness of content, and enabling rapid replication of SaaS ideas, multiples on content- or software-based businesses have dropped significantly. That means both risk and opportunity for buyers. ➥ Patience and strategic focus beat volume-based roll-ups. Instead of snapping up every deal, it’s smarter to take time, understand what works inside the business, and selectively scale what’s already strong — especially if you plan to operate (not flip) long-term. ➥ Passion and niche alignment improve acquisition success. Businesses tied to hobbies, communities, or long-term interests tend to perform better when buyers are genuinely invested, because passion translates to better stewardship and resilience through ups and downs. ➥ In attractive niches, speed is everything. When a good business hits the market (clean model, diversified traffic, good margins), multiple buyers are often ready — meaning you need clear, fast decision-making if you want to win the deal.   About Yury Byalik Yury Byalik is a seasoned growth marketer, acquisitions strategist, and digital-business investor with over 15 years of experience building, buying, and scaling profitable online businesses. Currently, he serves as Head of Strategy & Acquisitions at Onfolio Holdings, a public company that acquires and operates a diversified portfolio of digital assets. Before that, Yury worked across digital marketing, SEO, and business law, giving him a unique blend of operational, legal, and deal-sourcing expertise. He is a recognized speaker and contributor on topics such as deal sourcing, acquisition evaluation, and value creation in the online business space.   Connect with Yury Byalik ➥ https://levelfield.io/ ➥https://bridgethegap.ai/   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.

In this episode of the BOB Podcast, Jaryd Krause sits down with Nick Bradley, a world-renowned author, speaker, and business growth expert known for helping entrepreneurs, business leaders, and investors build, scale, and sell high-value companies. Nick brings more than a decade of Private Equity experience to the conversation. Throughout his career, he has completed over 50 acquisitions, sold 26 businesses, created over $5 billion in value, and played key roles in three exits exceeding $1 billion each. His expertise offers a rare, behind-the-scenes look at what it truly takes to buy, integrate, grow, and exit companies at scale. In this episode, listeners will learn: 💡 The criteria first-time acquirers should focus on 🔧 Nick’s Squared Management System—the four pillars and 40 essential elements that create a solid management foundation 🤝 How to merge two businesses, how long integration takes, and the steps involved in acquiring for growth 🧠 The mindset required for those building a portfolio through acquisition 📈 The characteristics of successful portfolio builders, including why “boring” businesses often become the most profitable For anyone considering growth through acquisition or curious about how seasoned investors strategically scale companies, this episode provides the insights and frameworks needed to navigate the world of M&A with confidence.   Episode Highlights 02:10 –  Why Founders Struggle? 04:41 – Strategic vs. Financial Value: Understanding "The Buyer’s Math"  07:00 – Build Your Business To Be Sellable 09:21 – What PE Firms Do Differently: Discipline, Detachment & Focus   Key Takeaways ➥ Most founders misunderstand what truly drives business value. They tend to focus on revenue or profit, but in reality, those are only about 40% of the valuation—60% comes from operational, strategic, and structural factors that founders often overlook. ➥ Sophisticated buyers play a different game. Private equity firms and large acquirers buy and sell companies constantly. They know the rules, the metrics, and the process far better than most founders who are going through a once-in-a-lifetime sale. ➥ Value is based on the buyer’s math, not the seller’s. Strategic buyers care about customer bases, distribution, systems, capability, geographies, and integration potential, not just financial performance. Founders must understand what their business is worth to the buyer. ➥ A business should always be built to be sellable—even if you never sell. A well-built business creates freedom, independence, and optionality. When a sale opportunity comes, you’ll be in the best position to maximize value. ➥ Private equity excels because of emotional detachment and absolute focus. PE firms operate with military-level discipline—no emotional decision-making, full clarity on end goals, and a strict focus on executing a plan that increases value fast. This contrasts with founders who are often emotionally attached to their business.   About Nick Bradley Nick Bradley is a world-renowned author, speaker, and business growth expert who works with entrepreneurs, business leaders, and investors to build, scale, and sell high-value companies. After spending a decade in Private Equity, Nick has seen the ups and downs of business growth and the key challenges that impact business performance. During that time, he completed over 50 acquisitions, sold 26 businesses, and created over $5bn in value. He has personally been involved in 3x exits valued at over $1bn each. Nick believes that scaling and eventually selling your business isn’t a “game of chance”. With guidance and support, your business can navigate the complexities of markets, scale efficiently, attain business goals that match your vision, and achieve an outstanding exit that reflects the hard work you have invested in your journey. He also believes in leveling the playing field with sophisticated buyers, such as Private Equity, equipping business owners with the strategies and tools to compete in the fierce world of M&A … and win the game.   Connect with Nick Bradley ➥Nick’s LinkedIn: linkedin.com/in/realnickbradley ➥ Exit Your Business For Millions - Download This Guide: https://go.highvalueexit.com/opt-in    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.

Think a million-dollar online business is out of reach?  The real barrier isn’t the price—it’s everything you don’t see coming before you even sign. In this solo episode, Jaryd Krause pulls back the curtain on the part of buying a 7-figure business that almost nobody talks about—the real costs, the real timelines, the real competition, and the parts of the process that can quietly wreck your deal long before you ever get to the closing table. Most people assume a $1M acquisition is simple math:Find the business, put down the deposit, sign some papers, done. But behind every one of those deals are fees, structures, advisors, lenders, deadlines, and expectations that—if you’re not prepared—will eat your budget and your sanity alive. Here’s what Jaryd gets into: 📌 The actual line-item expenses of buying a 7-figure business (legal, advisors, due diligence,  escrow, lender fees—yes, all of it) 📌Why doing a smaller deal doesn’t necessarily make anything easier and why some “cheap” deals cost more in mistakes 📌How the right deal structure can turn upfront costs into credits that reduce what you owe at closing 📌 The role of buyer-side advisors —what they charge, what they’re worth, and when you shouldn’t hire one 📌 The hidden criteria lenders use to judge your deal that most buyers don’t even know they’re being evaluated on 📌 Why timelines are never linear and competition is always sharper at the top 📌 The mindset traps that sabotage buyers and how patience becomes the most profitable strategy you have   Jaryd doesn’t dress it up. He walks you through the real picture—what it costs, what’s negotiable, what’s risky, and what will give you an edge when everyone else is rushing and guessing. If you’ve ever wondered whether you can actually afford a million-dollar acquisition, consider this your roadmap—and your reality check. 🎧 Plug in. This one will change the way you look at buying a business.     Episode Highlights 01:15 – Differences between sub-$500K deals vs seven-figure acquisitions 02:24 – Key costs when buying a seven-figure business 04:52 – Why do you need a specialized M&A lawyer? 07:13 – How to structure legal packages for letters of intent, asset purchase agreements, and contract due diligence 16:56 – Why larger businesses can be easier to acquire despite higher costs, and how cash flow impacts returns 19:22 – How long it can take to close a seven-figure business deal and factors affecting timing 21:40 – Cash vs. financed deals: the impact on negotiation power and deal structure 23:55 – Setting realistic expectations and why compounding small wins builds confidence in acquisitions 26:17 –  Why do you need to work with experts?     Key Takeaways ➥ Legal fees for M&A lawyers usually run 1–2% of the deal, and using an experienced online business acquisition lawyer is essential. ➥ Finance broker fees range from $5K–$10K, with SBA or lender fees around 3.5–3.75% of the financed amount, often rolled into the loan. ➥ Buyer-side advisors (3–8% of deal size) can review due diligence, advise on deal structure, negotiate, and sometimes source pre-vetted businesses. ➥ Due diligence packages ($5K–$40K) and escrow (~1% of acquisition) are key costs, but many upfront fees can be credited toward your deposit. ➥ With smart planning, many upfront costs—legal, advisor, and broker fees—can be credited toward your deposit, allowing acquisition with just 10% cash down. ➥ The larger the business, the more leverage you have, and the more stable the cash flow. Entry costs scale, but ROI potential often increases with size. ➥ Acquisition timelines vary widely—sometimes months, years—depending on market availability, acquisition criteria, and competition. Patience is key. ➥ Set realistic expectations. Overly ambitious goals or standards can harm mindset and decision-making. Compounding small wins builds confidence and sustainable success.  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/3YmJAm ➥ 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 one thing stopping you from owning a thriving online business isn’t money… but what you don’t know about SBA financing?  In this episode, Jaryd Krause chats with Ray Drew—aka SBA Ray—host of The Art of SBA Lending, the #1 podcast that pulls back the curtain on how SBA loans really work. Ray is the Managing Director at Truliant Federal Credit Union, a deal closer with hundreds of successful SBA-financed businesses under his belt, the man behind millions in SBA-backed deals, and the architect of SBA success stories nationwide. He’s seen everything—the smooth wins, the total nightmares, and the deals that fell apart days before closing. Most people think an SBA loan is simple: apply, get approved, buy the business, boom—you’re a CEO.  But the truth?  There are traps hidden in plain sight. And missing just one could cost you the deal—or tens of thousands in wasted time and fees. Here’s what Ray and Jaryd dive into: 🔥 The hidden misconceptions that trip up first-time buyers (even the smart ones)🔥 Why your “perfect” deal structure could actually kill your loan approval🔥 The truth about interest rates, balloon payments, and seller financing nobody tells you🔥 What really happens behind the scenes when lenders assess your deal🔥 The surprising reason your loan might get rejected even if you’re qualified 🔥 How long does the process really take—and what delays can quietly blow up your timeline🔥 Why the right M&A attorney can save your deal when everything’s on the line Ray doesn’t sugarcoat it—he breaks down exactly what’s going wrong in the SBA space and what you need to know before you sign anything. If you’ve ever dreamed of acquiring an online business but didn’t know how to fund it, this is your reality check and your roadmap. Because when it comes to SBA lending, it’s not just about money… It’s about knowing the game before you play it. 🎧 Grab your headphones. This one could save your next deal.   Episode Highlights 01:12 – What SBA lending is and why it’s a game-changer for business buyers 06:40 – Why buying a business often beats starting from scratch 09:24 – The most common misconceptions about SBA loans 12:10 – Key factors lenders look for before approving a deal 15:32 – The #1 mistake buyers make during the SBA loan process 18:46 – How to choose the right lender and build a strong relationship 21:55 – Real stories from hundreds of SBA-financed deals—the smooth, the messy, and the ones that fell apart 25:08 – How does the deal structure and negotiation impact loan approval 28:26 – Why preparation is the real secret to fast, successful closings 31:47 – Ray’s process for evaluating if a business is truly financeable 34:15 – Lessons from deals that went wrong—and how to avoid the same pitfalls 37:28 – What every buyer should do 6–12 months before applying for an SBA loan 39:52 – Ray’s best advice for entrepreneurs who want to acquire a business in 2025   Key Takeaways ➥ SBA financing is one of the most powerful yet misunderstood tools for buying a business—it lets entrepreneurs acquire profitable companies with as little as 10% down. ➥ Preparation is everything. Clean financials, accurate tax returns, and a solid business plan can drastically increase your chances of getting approved. ➥ The right lender matters more than most realize. Experienced SBA lenders can structure deals creatively, solve problems quickly, and close with confidence. ➥ Not all deals are created equal—lenders look for stable cash flow, strong management transitions, and businesses with proven profitability. ➥ Expect surprises. Even well-structured deals can fall apart near closing, so patience, flexibility, and expert guidance are essential. ➥ Buying a business with SBA financing isn’t just about getting a loan—it’s about acquiring a long-term wealth vehicle that can transform your financial future. ➥ Execution beats theory. Ray’s track record proves that the best buyers are those who take action, learn from each deal, and build relationships with trusted lenders.   About Ray Drew Ray Drew is the SBA Managing Director at Truliant Federal Credit Union, where he helps entrepreneurs buy businesses through SBA financing. With over a decade in the industry, Ray has closed hundreds of deals and is widely regarded as one of the leading voices in SBA lending today. He is also the host of the #1 podcast in the SBA lending industry, The Art of SBA Lending.   Connect with Ray Drew ➥ www.sbaray.com ➥ https://www.youtube.com/@SBA_Ray    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.