Buying Online Businesses Podcast

50+ Buyers In 2 Months - The Micro-SaaS Exit Strategy Most Sellers Never Think To Use with Ovi Shekh

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

10 Small Biz Acquisitions & Content Website Recovery Strategies with Brock Yates

What does it actually look like to buy 10 online businesses over 14 years - and still be standing? Not the highlight reel. The chargebacks, the 95% traffic drops, the seller-financed deal you hand back four months in because you simply can't make it work. The slow, painful realization that passive income was never really the point - ownership was. Brock Yates has been buying online businesses since 2012, starting with a $3,000 turtle website he found on Flippa with zero SEO knowledge and zero plan. By the time he quit his day job in Switzerland to go full-time, he had a portfolio of content sites generating more than his salary. Then the Google Helpful Content Update hit. And then ChatGPT changed everything. In this episode, Brock doesn't just share what went wrong - he shares what he actually did to crawl back, adapt, and build something more resilient on the other side.   In this episode, you'll learn: * Why Brock handed a $220K–$280K e-commerce acquisition back to the seller after four months - and what he'd do completely differently today * The one thing every first-time buyer underestimates: the seller's institutional knowledge and what disappears the moment they walk out the door * How a 95% traffic drop forced him to rethink content sites entirely - and why the turtle website outlasted everything else in his portfolio * The WooCommerce vs. Shopify decision that's shaping his entire content-to-commerce strategy now * How he used ChatGPT to build a free tool in 20 minutes that took a brand-new GM vehicle site from zero to 1,000 email subscribers - and counting * Why buying a business to "own for 10 years" changes every decision you make from day one * The niche-selection mistake that kills most content sites before they ever have a chance to grow Whether you're sitting on a content site wondering what to do next, or you're a first-time buyer trying to avoid the mistakes most people only learn the hard way - this conversation is one of the most honest, practical accounts of what building an online portfolio actually looks like across a decade. 🎧 Hit play - this is what 10 acquisitions of real-world experience sounds like when someone's willing to tell you all of it. Episode Highlights 03:29 - How a $3K Turtle Website Turned Into His First Online Business and Had Its Money Back Within 12 Months 08:24 - The Vegas Breakfast Deal: Why It Became His Most Expensive Education 11:49 - The Real Cost of Skipping Due Diligence on a $250K Acquisition 15:26 - Why Handing the Business Back to the Seller Was the Best Decision Available 17:43 - How the Google Helpful Content Update Wiped Out a Portfolio He'd Spent Years Building - Right After He Quit His Day Job 24:31 - Why the One Property He Built Survived the Crash While Every Listicle-Only Site Quietly Died 31:45 - The 20-Minute ChatGPT Tool That Beat Months of Pinterest Ad Spend   Key Takeaways ➥ The seller's knowledge is part of the asset - and it walks out with them. Before you close, map every decision that still lives inside the founder's head. ➥ Due diligence isn't verifying numbers - it's finding costs that aren't on the P&L yet. Chargebacks. Expiring inventory. Hidden fees. The surprises that break deals hide in the operational layer. ➥ Seller financing only works as well as the relationship behind it. When Brock couldn't make payments, a real relationship meant a clean exit, not a lawsuit. ➥ The sites you focus on survive. The ones you abandon don't. In a portfolio, attention is the most important thing you allocate. ➥ Thin content was never a business, it was a bet on Google never changing the rules. Build for the reader. The algorithm catches up eventually. ➥ If your content site has traffic, it has buying intent. Capture it. WooCommerce on the root domain. Google Merchant Center. Set it up before you think you need it. ➥ The best tool to build is the one you were frustrated you couldn't find yourself.   About Brock Yates Brock Yates is an independent publisher behind GMT Central and AllTurtles, where he builds practical content brands for enthusiast audiences. His work focuses on SEO, content strategy, and adapting niche websites to major changes in search.   Connect with Brock Yates ➥https://gmtcentral.com/ [https://gmtcentral.com/] ➥https://www.allturtles.com/ [https://www.allturtles.com/]   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause [https://www.linkedin.com/in/jarydkrause]➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com [https://buyingonlinebusinesses.com/] ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ [https://buyingonlinebusinesses.com/freeresources/]➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ [https://buyingonlinebusinesses.com/sell-your-business/] ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ [https://buyingonlinebusinesses.com/ads-services/]   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE [https://bit.ly/3RtyMkE] ➥ Flippa - https://bit.ly/3wGa8r5 [https://bit.ly/3wGa8r5] ➥ Motion Invest - https://bit.ly/3YmJAmO [https://bit.ly/3YmJAmO]➥ Investors Club - https://bit.ly/3ZpgioR [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 [https://omnystudio.com/listener] for privacy information.

Beware AI Is Quietly Killing These Online Business Models - Don’t Buy These, Unless… with Jaryd Krause

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 [https://www.linkedin.com/in/jarydkrause]➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com [https://buyingonlinebusinesses.com/] ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ [https://buyingonlinebusinesses.com/freeresources/]➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ [https://buyingonlinebusinesses.com/sell-your-business/] ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ [https://buyingonlinebusinesses.com/ads-services/]   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE [https://bit.ly/3RtyMkE] ➥ Flippa - https://bit.ly/3wGa8r5 [https://bit.ly/3wGa8r5] ➥ Motion Invest - https://bit.ly/3YmJAmO [https://bit.ly/3YmJAmO]➥ Investors Club - https://bit.ly/3ZpgioR [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 [https://omnystudio.com/listener] for privacy information.

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/ [https://www.linkedin.com/in/ace-chapman/] ➥http://www.acechapman.com/ [http://www.acechapman.com/]  Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause [https://www.linkedin.com/in/jarydkrause]➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com [https://buyingonlinebusinesses.com/] ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ [https://buyingonlinebusinesses.com/freeresources/]➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ [https://buyingonlinebusinesses.com/sell-your-business/] ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ [https://buyingonlinebusinesses.com/ads-services/]   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE [https://bit.ly/3RtyMkE] ➥ Flippa - https://bit.ly/3wGa8r5 [https://bit.ly/3wGa8r5] ➥ Motion Invest - https://bit.ly/3YmJAmO [https://bit.ly/3YmJAmO]➥ Investors Club - https://bit.ly/3ZpgioR [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 [https://omnystudio.com/listener] for privacy information.

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.karllhughes.com/]   ➥https://www.linkedin.com/in/karllhughes/ [https://www.linkedin.com/in/karllhughes/]    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause [https://www.linkedin.com/in/jarydkrause]➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com [https://buyingonlinebusinesses.com/] ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ [https://buyingonlinebusinesses.com/freeresources/]➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ [https://buyingonlinebusinesses.com/sell-your-business/] ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ [https://buyingonlinebusinesses.com/ads-services/]   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE [https://bit.ly/3RtyMkE] ➥ Flippa - https://bit.ly/3wGa8r5 [https://bit.ly/3wGa8r5] ➥ Motion Invest - https://bit.ly/3YmJAmO [https://bit.ly/3YmJAmO]➥ Investors Club - https://bit.ly/3ZpgioR [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 [https://omnystudio.com/listener] for privacy information.