Buying Online Businesses Podcast

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

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

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