Buying Online Businesses Podcast

What if you could buy a seven-figure business without putting down a huge pile of cash? Clayton Pritchard did exactly that. He wasn’t even looking to buy a business. Then the founder of Olivine Marketing asked him a simple question: “Would you like to buy it?” Instead of a massive upfront payment, Clayton structured the acquisition around a percentage of revenue. Low risk. Massive upside. But here’s the part that makes this deal really interesting. Before taking over, Clayton stepped in as CEO to prove he could actually grow the business. And within months, the company went from declining growth to tracking nearly 50% year-over-year growth. The business already had the assets: strong organic traffic, years of content, an established brand, and inbound leads. Clayton’s job was to unlock the value that was already there. In this episode, Jaryd sits down with Clayton to unpack how he acquired a seven-figure agency with no traditional cash-down deal, why the founders chose him over private equity, how he structured the revenue-based acquisition, what due diligence looked like from the inside, and how he turned better sales and conversion into rapid growth. They also get into how employees can turn their expertise into ownership, why buying an imperfect business can create more upside than buying a “perfect” one, and where AI fits into the future of product marketing. Because you don’t always need a giant bank account to buy a business. Sometimes, you need a relationship, a clear value-creation plan, and the courage to make the offer. 🎧 Hit play, this is how Clayton bought a seven-figure agency without putting millions on the line.   Episode Highlights 02:56 – How an Unexpected “Would You Like to Buy It?” Conversation Turned Into a Seven-Figure Agency Acquisition 08:28 – Why the Founders Turned Down Private Equity to Put the Business in the Hands of Someone They Trusted 09:35 – The Acting-CEO Test: How Clayton Proved He Could Reverse a Declining Business Before Taking Ownership 20:22 – The No-Money-Down Acquisition Structure: How Paying a Percentage of Revenue Made the Deal Extremely Low Risk 24:52 – The Due Diligence Advantage of Already Being Inside the Business, And the Red Flags Clayton Looked For 27:07 – Why He Chose Revenue Over Profit for the Deal Structure,  And How Buyers Can Protect Themselves From Manipulating Margins 29:06 – The Employee-to-Owner Playbook: How to Create Value First, Then Use That Value to Buy Into a Business Without Millions in Cash   Key Takeaways ➥ You don’t need millions in cash to buy a business. The right deal structure can turn a massive upfront payment into a low-risk, revenue-based acquisition. ➥ Your network can become your deal flow. Clayton wasn’t hunting for Olivine. Years of trust and staying connected brought the opportunity directly to him. ➥ Prove you can grow it before you buy it. Clayton stepped in as CEO first, tested his ability to move the business forward, and used the results to validate the acquisition. ➥ The biggest opportunity may be hiding inside a “declining” business. Olivine already had the brand, content, SEO, and inbound engine. Clayton didn’t need to rebuild it, he needed to unlock what was already there. ➥ Structure the deal so both sides win. Tying the sellers’ payout to revenue gave Clayton less downside while giving the founders a reason to keep helping the business grow. ➥ If you want ownership, start by creating value. Employees with deep knowledge of a business can identify what they would change, prove the impact, and potentially turn that leverage into equity or ownership. ➥ AI can make the work faster, but it can’t replace strategic judgment. Research and execution can be accelerated, but positioning, stakeholder alignment, and getting people to make decisions still require human expertise.   About Clayton Pritchard Clayton Pritchard is CEO and owner of Olivine Marketing, a B2B product marketing agency serving SaaS and tech companies from seed to post-IPO. A former marketer at Meta and LinkedIn, Clayton worked with Olivine as a contractor before leading the business on a trial basis in late 2025, then acquired it from the founders in April 2026. Under his ownership, Olivine is now growing at nearly double its original first-year target.   Connect with Clayton Pritchard ➥ https://www.linkedin.com/in/claytonpritchard/  ➥ https://www.olivinemarketing.com/     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   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 can kill a $10.5 million acquisition, and how can an experienced buyer spot a bad deal in the first 10 minutes? Neil Twa has reviewed 500+ businesses and learned that the biggest red flags often show up before serious due diligence even begins. Messy financials. AI-generated business plans. Numbers that collapse when checked against the actual bank, Stripe, and PayPal data. And sometimes, even when everything looks right, the deal still falls apart. In this episode, Jaryd sits down with Neil to unpack the deal that looked so good the seller decided not to sell, the business deal that ghosted him after six months of due diligence, and the $10.5M acquisition that came with SBA financing, retail complexity, and a partner trying to sabotage the transaction. Neil also reveals why his team changes almost nothing during the first 30 days after an acquisition, how they operate 30 brands with AI-powered systems, and why reputation can be worth more than any single deal. If you're buying online businesses, this is a masterclass in spotting problems early, surviving the surprises you can't see coming, and knowing when to walk away. 🎧 Hit play to learn what an experienced acquirer can see in the first 10 minutes that could save you months, and potentially millions.   Episode Highlights 03:32 – How Neil Reviewed 500+ Businesses to Find the Few Deals Worth Buying 06:45 – The First 10-Minute Deal Killers: Messy Financials, Missing Documents, and Disorganized Seller Packages 07:58 – The AI Due Diligence Trap: How Fake Business Plans and Unverified Numbers Fall Apart Under Scrutiny 12:50 – The Deal That Looked Too Good to Sell: Why the Seller Backed Out Just Before Signing the LOI 16:17 – The 6-Month Ghosting Nightmare: When a Seller Disappeared After Months of Due Diligence 22:55 – The $10.5M Acquisition: How Neil Navigated SBA Financing, Retail Complexity and a Deal That Nearly Fell Apart 37:09 – Why Reputation Beats Money: The Trust Principle That Becomes More Important the Higher You Go 38:17 – The First 90 Days After an Acquisition: Why Neil Says Change Nothing for 30 Days and Learn Before You Optimize   Key Takeaways ➥ The first 10 minutes can save you months of wasted due diligence. Messy financials, missing disclosures, disorganized seller packages, and numbers that don't reconcile are early signals to walk away, not problems to hope will magically improve. ➥ AI doesn't replace credibility. A polished, AI-generated business plan means nothing if the seller can't explain the business behind it. Buyers need to verify the numbers, assumptions, and documents, not simply trust what AI produces. ➥ A great-looking deal can still fall apart for reasons you can't model on a spreadsheet. Neil had a seller back out just before signing the LOI because the diligence process made him realize how valuable his own business was. ➥ Due diligence doesn't end when you find the numbers you expected. Hidden liabilities, undisclosed agreements, missing inventory costs, and other surprises can surface right before or even months after closing. Structure the deal with those risks in mind. ➥ The first 90 days after an acquisition should be about learning, not immediately changing everything. Neil's approach is simple: spend the first 30 days changing almost nothing, map the business and its people, then identify the highest-impact improvements before acting. ➥ Operational complexity can create the biggest opportunities. Neil turned acquisitions with Amazon and retail channels into broader omnichannel businesses by identifying unused growth channels, improving systems, and using data to understand where growth actually creates value. ➥ Reputation compounds and becomes more valuable as you move up. Deals, capital, and relationships increasingly depend on trust. Neil's acquisition philosophy is built around being a "kingmaker": helping operators succeed while protecting the reputation and relationships that took years to build.   About Neil Twa Neil Twa is the CEO and co-founder of Voltage Holdings, where he and his clients have generated over $100 million in ecommerce sales since 2012. A former IBM executive, Neil has launched, scaled, and exited multiple 8-figure brands and mentored over 1,000 operators using his Train-Equip-Activate framework. He now focuses on building "generative" businesses engineered for margin and exit-readiness from day one, and helps buyers spot the difference between a business that looks great and one that actually is.   Connect with Neil Twa  ➥https://info.voltagedm.com/podcast-free-book    ➥https://voltagedm.com  ➥https://www.linkedin.com/in/neiltwa/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   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.

Everyone wants to know how to buy a great business. Almost nobody talks about how great businesses quietly become bad deals. After more than 300 business transactions, Joe Burrill has seen it happen time and time again. Sellers mentally check out months before they list. Buyers obsess over valuations while missing the risks that actually matter. And now, with AI changing the way online businesses are built, bought, and grown, the gap between good buyers and great ones is only getting wider. So what should you actually be looking for? In this episode, Jaryd sits down with Joe to unpack the lessons he's learned from brokering hundreds of online business sales. They explore why the best deals aren't always the fastest-growing ones, how experienced buyers think about traffic, revenue diversification, and risk, and why a simple conversation between buyer and seller can be more valuable than another spreadsheet. They also dive into how AI is reshaping acquisitions. Why content businesses aren't dead. Why SEO still matters. And where new buyers are getting due diligence completely wrong by relying too heavily on AI instead of using it as a tool. If you're thinking about buying your first online business - or your next one - this episode will change the way you evaluate opportunities. Because finding a business to buy isn't the hard part. Knowing which one is actually worth owning is. 🎧 Hit play and learn what 300+ deals have taught Joe that most buyers never find out until it's too late.   Episode Highlights 03:32 – How Joe Turned One Website Into a Career—and Eventually 300+ Business Deals  08:31 – The #1 Mistake Sellers Make That Quietly Destroys Their Business Value Before an Exit  12:02 – The $15K Deal That Used a $2K Holdback to Get Both Buyer and Seller to Say Yes 18:24 – The New Rules for Buying Content Websites in an AI-First World  24:08 – Why AI Won't Replace SEO—and the Costly Mistake Buyers Keep Making During Due Diligence 29:18 – The $172K Valuation Error AI Completely Missed—and Why Human Judgment Still Wins 37:15 – If You Had $20K–$100K Today, Here's Exactly What Joe Would Look For in an Online Business    Key Takeaways ➥ The fastest way to kill your exit? Stop running the business before it's sold. Buyers don't buy potential—they buy momentum. ➥ Deals close on trust, not spreadsheets. Strong buyer-seller relationships solve problems that contracts can't. ➥ One traffic source is a liability. Diversification is a premium. The more ways a business earns traffic and revenue, the more valuable it becomes. ➥ AI is a powerful assistant—not your deal advisor. It can speed up due diligence, but it can't replace experience, judgment, or pattern recognition. ➥ Content websites aren't dead. Generic content is. The winners are building brands, authority, and original insights that AI can't replicate. ➥ Creative deal structures create better outcomes. Seller financing, holdbacks, and flexible terms often turn stalled negotiations into closed deals. ➥ Buy the business you're best positioned to grow—not just the cheapest one you can afford. Your competitive advantage matters more than the asking price.   About Seph Fontane Pennock Seph Fontane Pennock is a serial entrepreneur and 8-figure exit founder who built PositivePsychology.com from a personal blog into one of the world's most visited mental health platforms, serving over 19 million users. He grew it to a PE acquisition without spending a dollar on ads, relying purely on SEO-led content strategy. Post-exit, he co-founded the SaaS platform Quenza and has since launched Regenerated.com. Seph is now an active investor and builder.   Connect with Seph Fontane Pennock ➥ https://www.linkedin.com/in/seph-fontane-pennock-94666421/   ➥ https://psychology.com/     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   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 e-commerce brands are chasing AI the wrong way. They're publishing AI-generated blogs. Stuffing their sites with keywords. Obsessing over prompts. And wondering why nothing changes. Meanwhile, some brands are quietly growing their organic revenue by 30-40% year over year without relying on hacks or chasing the latest AI trend. The difference? They understand that AI hasn't replaced SEO. It's changed how people discover businesses. In this episode, Colin Ma breaks down the exact playbook he's using to grow established e-commerce brands through the combination of traditional SEO and Answer Engine Optimization (AEO). He explains why real customer questions are now one of the biggest competitive advantages, how a simple change to your collection pages can unlock entirely new traffic, and why optimizing your Google Merchant Center feed can drive thousands of additional clicks, often in just a couple of months. But the conversation goes well beyond rankings. Colin also shares how AI has completely transformed his workflow, allowing him to produce the work of an entire agency without sacrificing quality. From using Claude to analyze thousands of customer emails in minutes to building SEO assets that once took weeks, he reveals where AI actually creates leverage and where trusting it blindly can become an expensive mistake. If you're running an e-commerce brand, buying online businesses, or trying to figure out what SEO looks like in the AI era, this episode is packed with practical strategies you can apply immediately. 🎧 Hit play and discover why the future of SEO isn't about replacing the fundamentals. It's about using AI to execute them better than everyone else   Episode Highlights 05:00 - How Colin Is Driving 30-40% Year-on-Year SEO Growth for Household E-commerce Brands Using AI 08:10 - Why Real Customer Emails Beat SEO Tools Every Time When Optimizing for ChatGPT and AI Search 12:18 - The Collection Page Strategy That Most E-commerce Stores Miss and How It Unlocks More Organic Traffic 18:32 - How Optimizing Google Merchant Center Feeds Turned 200 Monthly Clicks Into Nearly 5,000 in Just Two Months 22:45 - Why Claude Has Made SEO Fun Again and the AI Workflow That Replaced Weeks of Manual Work 26:08 - The Dangerous Mistake Businesses Make by Trusting AI Blindly (And Why Colin Fired a Client Over It) 35:12 - Why Buying Pure Content Sites Is Riskier Than Ever and What Colin Would Look for Instead in the AI Era Key Takeaways ➥ SEO remains the foundation of AI search. Brands with strong SEO are far better positioned to appear in ChatGPT, Claude, and other AI-powered search platforms. ➥ Real customer questions outperform traditional keyword research. Mining support emails, live chats, and customer inquiries helps create content that matches how people actually search and how AI models understand intent. ➥ Better category pages create more growth opportunities. Expanding collection pages into more specific subcategories gives Google and AI search engines more relevant pages to rank. ➥ Optimizing your Google Merchant Center feed can generate fast wins. Richer product data improves visibility in Google's free listings while often boosting paid campaign performance as well. ➥ AI is a force multiplier, not a replacement for expertise. The biggest gains come from using AI to automate repetitive work so you can spend more time on strategy, analysis, and decision-making. ➥ Human judgment still matters. AI is incredibly powerful, but blindly accepting its recommendations without validating them can lead to costly mistakes. ➥ Sustainable growth comes from combining AI with genuine customer value. Businesses that solve real customer problems while using AI to execute faster will have the strongest competitive advantage in the years ahead.   About Colin Ma Colin Ma is a digital entrepreneur and SEO operator with over 10 years of experience building, buying, and selling online businesses. He's acquired, grown, and exited 15+ content and affiliate brands,  including multiple six-figure deals. Known for his data-driven, systems-first approach to SEO, Colin now manages a portfolio of large digital brands, using AI-powered workflows to drive 30–40% year-on-year growth with leaner, more consistent teams than ever before.   Connect with Colin Ma ➥ https://matchagrowth.com/ ➥https://www.linkedin.com/in/colinlma/     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence   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.