Buying Online Businesses Podcast

Buying Online Businesses
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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. 2D AGO

    He's Done 200+ Acquisitions - Here's What The Online Business Acquisition Market Looks Like with Ace Chapman

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

    41 min

  2. APR 29

    Buying A Digital Agencies Nobody Else Wants And How To Scale Them with Karl Hughes

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

    42 min

  3. APR 22

    Successful Content Website HoldCo From Acquiring 5+ Businesses with Qayyum Rajan

    What if you could sell a business, get it handed back to you for $100, flip it again for a profit -and use that whole experience to build something even bigger? That's not luck. That's Qayyum Rajan. In this episode, Jaryd sits down with Qayyum -founder, developer, and holdco builder -who turned a single LinkedIn cold message into a PE exit, watched that same PE firm quietly forget his business existed, bought it back for $100, and relisted it on MicroAcquire while two buyers bid against each other in real time. But here's where it gets really interesting. After the exit, while everyone else was running away from content sites -Google had just torched their traffic with the helpful content update -Qayyum was running toward them. Buying burnt-out founders' blogs for $10K–$50K. Merging them. Building newsletters nobody had touched. Going faceless on YouTube. And quietly turning the whole thing into a cash-flowing media holdco that made back its entire investment in nine months. You'll learn how he evaluates and closes acquisitions in under 24 hours, why "domain authority and love" are his two non-negotiables, what it actually looks like to consolidate three sites under one domain without destroying the traffic -and why he thinks the biggest opportunity in content right now is hiding inside the businesses everyone else already walked away from. Most buyers wait for the perfect business. Qayyum just knows how to read the ones everyone else missed. 🎧 Hit play -this is what building a holdco from the wreckage actually looks like.   Episode Highlights 02:56 The LinkedIn Cold Message That Started a PE Exit Nobody Saw Coming 05:35 The $2,000 Credit Card Lien That Almost Blew Up a Million-Dollar Deal 12:02 Bought Back for $100: How Qayyum Got His Own Business Returned to Him 14:45 The MicroAcquire Bidding War -Two Buyers, Five Days, Real-Time Updates to His Wife 18:32 Why He Started Buying Content Sites Right When Google Was Destroying Them 28:52 Wealth Awesome -Buying a Finance Blog for 1x Revenue and Making It Back in Nine Months 38:22 The $20K Deal He Walked Away From -and Built Himself in a Week Instead   Key Takeaways ➥ You don't need a perfect business -you need an underutilized one. The real opportunity is in channels the previous owner never touched: newsletters, YouTube, social. That's where the upside is hiding. ➥ Domain authority and founder love are the two things worth paying a premium for. Everything else can be built. Backlinks and brand equity take years -you can't manufacture them overnight. ➥ When Google cuts your traffic, don't fight it -diversify around it. Bing, newsletters, YouTube Shorts, and faceless video are quietly outperforming SEO for content operators right now. ➥ Moving fast is a competitive advantage in small acquisitions. Most sellers aren't just looking for the best price -they want certainty. Close in 24 hours and you win deals slower buyers never even get to. ➥ A holdco only works if you're ruthless about focus. Shelve what isn't winning so you can double down on what is -spreading thin is how good acquisitions quietly die. ➥ Face-brand content sites are one of the most underpriced assets in the market right now. Use the dependency as a negotiation lever to lower the price, then go faceless and build something that can actually be sold. ➥ The exit multiple is everything -and it's timing. Qayyum sold at 20x earnings at the peak of the market. One year later, that same business lists for 4–5x. Getting out at the right moment matters as much as building the right thing.   About Qayyum Rajan Qayyum Rajan (known as 'Q') is a CFA Charterholder, former portfolio manager, and serial online business acquirer. He founded ESG Analytics in 2017 -sold it to PE, bought it back for next to nothing when the acquirer went under, and sold it again for six figures. He then built his own holdco, acquiring Wealth Awesome (a leading Canadian personal finance publication with 20,000+ readers) and Worqstrap, amalgamating two separate businesses into one. Based in British Columbia, he sits on the Fintech Advisory Committee for the BC Securities Commission.   Connect with Qayyum Rajan ➥ https://wealthawesome.com/ ➥https://www.linkedin.com/in/qayyumrajan/   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.

    51 min

  4. APR 15

    [Case Study] Red Vs Green Flags When Acquiring An Ecommerce Business with Jan

    What if the business everyone else passed on was actually the one? Most first-time buyers obsess over finding the perfect business - but the ones who actually close deals? They obsess over reading the business correctly. In this case study episode, Jaryd Krause sits down with Jan, a Buying Online Businesses graduate who went from consuming YouTube content and podcasts to acquiring a six-figure health and beauty e-commerce brand - and lived to tell the full, unfiltered story. Jan brought something most buyers don't: seven-plus years of digital marketing and DTC experience. And she used every bit of it to spot the green flags hiding inside what most buyers would have walked away from. You'll learn how Jan evaluated over 100 listings, deep-dived on 30 businesses before finding the one, negotiated inventory she didn't want out of the purchase price, and immediately unlocked growth through paid ads and an underutilized email list the previous owners barely touched. You'll also hear why red flags aren't dealbreakers - they're filters - and how the right background can flip a liability into your biggest competitive edge. If you're a first-time buyer trying to figure out what "good" actually looks like before you sign anything, hit the 🎧 Play button.   Episode Highlights 09:33 The Magic Number: How Many Businesses You Actually Need to Look at Before You Buy 12:22 Why Red Flags Are Just Green Flags in Disguise 15:40 The Inventory Negotiation Move That Saved Jan Thousands at Closing 19:16 The Untapped Email List That Was Sitting There Printing Money 22:00 Tariffs, Trouble, and Why Customer Diversity Saved This Business 28:31 The One Thing Jan Would Do Completely Differently on Her Next Acquisition   Key Takeaways ➥ Red flags aren't automatic dealbreakers - the right background turns someone else's liability into your biggest competitive advantage. ➥ An underutilized email list is cash sitting on the table - if the previous owner wasn't sending weekly, you're inheriting free revenue from day one. ➥ Negotiating out slow-moving inventory before closing isn't optional - it's one of the easiest ways to reduce your purchase price on the spot. ➥ Keeping previous owners involved beyond the handover isn't a weakness - it's the move experienced acquirers wish they'd made sooner. ➥ Waiting for the "perfect" market conditions before buying is the riskiest strategy of all - the real cost is the time, growth, and learning you never get back.   About Jan Patel Jan is a BuyingOnlineBusinesses.com graduate who went from digital marketing for large scale ecom brands in her day job. To now acquiring, owning and scaling her own ecommerce business.    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

  5. APR 8

    Micro SaaS Exits & Acquisitions From 20 Successful Deals with Stuart Faught

    What if you never needed to scale big - to sell big? Stuart Faught has done it 20 times. And he'll tell you - that's exactly the wrong way to think about it. Because what most SaaS founders don't realize… is that the real money isn't in building forever. It's in knowing exactly when to let go. Like the business he built, took to 100K ARR… and sold in 30 days flat. Or the deals where buyers showed up with zero-down offers and five-year payment plans… and got politely - but firmly - shown the door. Or the biggest mistake first-time SaaS buyers make - falling in love with the tech… when the only thing that actually grows the business is sales. In this episode, Jaryd Krause sits down with Stuart Faught - serial micro SaaS entrepreneur who has built and exited over 20 software businesses across verticals like dental, HVAC, med spas, and home care. All bootstrapped. All profitable. All sold. And this one gets real. Into why Stuart never scales past 100K ARR before selling - and why that's a feature, not a limitation. Into what he'd look for if he were buying a SaaS business tomorrow - and the red flags that would make him walk. Into why non-technical buyers are actually better positioned to grow software companies than most people think. But more importantly… Stuart breaks down the exact repeatable system behind 20 clean exits - what makes a deal close fast, what kills it dead, and why simplicity is the most powerful thing a seller can offer a buyer. No fluff. No theory. No "someday I'll do it big." Just 20 exits deep of hard proof - from someone who's figured out the game… and keeps winning it. 🎧 Hit play - this is what a real SaaS exit machine actually looks like.     Episode Highlights 02:40 The 50K–100K ARR Sweet Spot: Why Stuart Sells Before Most Founders Even Get Started 07:04 The 5X Formula: How Stuart Consistently Prices and Closes 20 SaaS Exits 10:54 The Deal Structure That Serious Buyers Use (And the One That Gets You Ghosted Immediately) 16:09 You Don't Need to Be Technical to Own a Tech Company - Here's What Actually Matters 18:51 How to Do Due Diligence on a SaaS Business Like Someone Who's Sold 20 of Them 21:04 The Secret to Growing Any Sub-$1M Business That Most Buyers Completely Overlook 23:08 Why First-Time Founders Make the Best Buyers - And How Stuart Finds Them Before Listing Key Takeaways ➥ You don't need to be technical to build, grow, or buy a SaaS business - sales and marketing skills matter far more. ➥ Targeting a 50K–100K ARR sweet spot before exiting allows for faster, cleaner deals without burnout or over-scaling. ➥ A 5X multiple on top-line revenue is a realistic and repeatable benchmark for micro SaaS exits in today's market. ➥ Keeping deal structures simple - at least 50% cash upfront with the remainder collected within 90 days - attracts serious buyers and closes deals faster. ➥ Talking to 3–5 customers during due diligence reveals more about a business's true health than financials alone ever will. ➥ Being an easy, honest, and respectful buyer is one of the most underrated competitive advantages in any acquisition process. ➥ Niching into a vertical SaaS doesn't trap you - adjacent markets and close-cousin industries create natural expansion paths when growth plateaus.   About Stuart Faught Stuart Faught is a serial SaaS entrepreneur who has built and sold 20+ micro-SaaS businesses across verticals including dental, orthodontics, HVAC, med spas, and home care. Known for his rapid exit strategy, Stuart closes most deals in 30-45 days by creating clean documentation and targeting niche markets. He's founded multiple companies including Praze, PatientSnap, Caddy, and Covington.ai. Stuart specializes in vertical SaaS solutions and teaches founders how to build for exits, not endless scaling.   Connect with Stuart Faught ➥ https://www.linkedin.com/in/stuart-faught-59a5a76b/   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.

    25 min

  6. APR 1

    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

  7. 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

  8. 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
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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
    Explicit
  • Copyright
    © 2026 Buying Online Businesses

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