Buying Online Businesses Podcast

Buying Online Businesses
  • 4.9 (29)
  • BUSINESS
  • UPDATED WEEKLY

Jaryd Krause quit his plumbing job in 2015 by acquiring online businesses and never looked back. Now one of the world's leading Online Business M&A advisors, he's helped thousands of people acquire profitable businesses, made his clients millions, and scaled companies from 6 to 8 figures. The Buying Online Businesses Podcast cuts through the noise on acquisitions, M&A strategy, and building real wealth through buying already profitable online businesses. Whether you're looking to replace your income or build a portfolio that funds the life you actually want, this is your show!

  1. 12H AGO

    He Acquired 50 Saas Businesses & Warns You Of What Brokers Won’t Tell You with Kevin Peterson

    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.

    29 min

  2. MAR 25

    He Sold the World’s Most-Visited Site - The Hidden Exit Mistakes You Can’t Afford with Nathan Gwilliam

    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.

    42 min

  3. MAR 18

    Buying a Business While Working Full-Time & Raising 7 Kids (No Margin for Error) with Michael Simpson

    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.

    40 min

  4. MAR 11

    [Case Study] From 9–5 to Freedom: How Alan & Mel Acquire, Grow, and Sell Online Businesses

    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.

    48 min

  5. MAR 4

    AI Is Rewriting Due Diligence & How We Acquire Businesses - Here’s How Buyers Win or Lose with Haytham Allos

    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.

    41 min

  6. FEB 25

    How $10M - $100M Online Business Acquisitions Are Done with Emmet Kilduff

    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.

    30 min

  7. FEB 18

    Which Buyers Lose Deals & Which Win M&A Deals & Why with Ryan Condie

    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.

    42 min

  8. FEB 11

    From SEO to GEO: How to Get Found in an AI-First Internet with Rad Paluszak

    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.

    35 min
See All (100)

4.9
out of 5
29 Ratings

About

Jaryd Krause quit his plumbing job in 2015 by acquiring online businesses and never looked back. Now one of the world's leading Online Business M&A advisors, he's helped thousands of people acquire profitable businesses, made his clients millions, and scaled companies from 6 to 8 figures. The Buying Online Businesses Podcast cuts through the noise on acquisitions, M&A strategy, and building real wealth through buying already profitable online businesses. Whether you're looking to replace your income or build a portfolio that funds the life you actually want, this is your show!

Information

  • Creator
    Buying Online Businesses
  • Years Active
    2019 - 2026
  • Episodes
    100
  • Rating
    Clean
  • Copyright
    © 2026 Buying Online Businesses

You Might Also Like