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He bought a SaaS business for $3,000. It had zero revenue. No payment gateway. Barely any real traffic. And some of the traffic being reported? It was basically the founder testing his own site. 18 months later, that same business was doing $3,000 a month in revenue. So what changed? Steven Macdonald didn't throw money at ads or try to monetize everything on day one. He knew the market, listened to customers, went all-in on SEO, and turned original research into a growth engine. He surveyed 200+ startups. Published the data. Started ranking for major OKR keywords. Built backlinks. Generated thousands of monthly visits. And kept improving the product based on what customers actually wanted. But the most interesting part might be what he didn't do. He didn't rush. Steven gave himself eight to ten years to build the business. That long-term mindset completely changed how he approached growth, product decisions, and even monetization. In this episode, Jaryd sits down with Steven to break down the $3K acquisition, how he took a zero-revenue SaaS to $3K/month, why knowing the market can matter more than the size of the deal, and how original research and AI are helping him compound organic growth. If you're thinking about buying a small SaaS, or wondering what can happen when you give a tiny business enough time to grow, this one is worth hearing. 🎧 Hit play. The acquisition cost $3K. The lessons are worth a lot more.   Episode Highlights 05:32 – The $3K Flippa Bid That Beat an $8K Asking Price, And Got Accepted the Next Day 07:54 – Buying a SaaS With $0 Revenue, No Payment Gateway, and Almost No Real Traffic 12:57 – The 8–10 Year Vision That Changed How He Approached Growth, Risk, and Patience 19:39 – How 30 Pieces of Content a Month and One 200+ Startup Research Study Started Driving Organic Growth 27:40 – From $0 to $3K/Month: The Simple SaaS Pricing Model Behind the Growth 30:58 – The Acquisition Lesson That Matters Most: Buy What You Actually Understand 33:53 – How He Uses AI + Original Research to Scale Content Without Publishing Generic AI Articles   Key Takeaways ➥ Buy what you understand. Knowing the market and customer pain points gave Steven confidence to act when he found OKRsTool.com. ➥ Small acquisitions can have big upside. A $3K purchase with zero revenue became a $3K/month business in 18 months. ➥ Learn before you monetize. Steven focused first on customers, feedback, and product improvements instead of chasing immediate revenue. ➥ Original research creates leverage. Surveying 200+ startups produced unique data that drove traffic, backlinks, and signups. ➥ SEO rewards patience. Steven kept publishing and improving while organic traffic gradually compounded into thousands of monthly visits. ➥ AI needs original insight. AI can scale content, but proprietary research and real expertise are what make that content valuable. ➥ Long-term thinking changes everything. An 8–10 year vision gave Steven room to experiment, learn, and let the business compound.   About Steven Macdonald Steven Macdonald is an SEO entrepreneur and SaaS founder based in Tallinn, Estonia. In early 2025 he acquired OKRs Tool, a lightweight OKR platform for startups, and grew it through SEO, product-led content, and AI search optimization instead of rebuilding the product. He previously founded Kingspoint, a SaaS-focused content marketing agency that scaled organic growth for clients like VWO, Hiver, SimCorp, and GetAccept. Steven turns overlooked SaaS businesses into search-dominant, demand-generating companies.   Connect with Steven Macdonald ➥ https://www.linkedin.com/in/steven-l-macdonald/  ➥ https://www.okrstool.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.

Buying your first business is exciting. Buying six more before you’ve figured out how to run the first one is where things get interesting. Dev Shah discovered acquisitions through Acquire.com and quickly went from being fascinated by the idea of buying businesses to actually building a portfolio of them. His first deal was Sourcely AI, a student research tool he bought for just $4,000 while it was making around $500 a month. A year and a half later, he had grown it to more than $5,000 in monthly recurring revenue and sold it for a low six-figure exit. But along the way, Dev acquired six other micro-businesses, all for less than $10,000 each, using the cash flow from his original acquisition. And that's where he learned one of the biggest lessons of his acquisition journey: just because you can buy another business doesn't mean you should. He couldn't integrate them as effectively as he expected. Some were sold. Some were shut down. Others continued running. Today, Dev has taken those lessons into a much bigger world of acquisitions. He runs a buy-side advisory firm helping search funds, startups, and other buyers source deals, conduct due diligence, negotiate, and get acquisitions across the finish line. And he's seen plenty go wrong. Sellers who disappear after an LOI. Businesses with information that turns out to be fake. Owners claiming revenue that can't actually be verified. Deals that look attractive until you start pulling apart the numbers. In this episode, Jaryd sits down with Dev to unpack what buying seven businesses taught him about moving too fast, how to build a buy box around your own skills and competitive advantages, and why serious buyers need to spend time in the market before they ever make an offer. Dev also breaks down his approach to due diligence, why you should treat those 30 days as if you're already taking over the business, how to avoid becoming emotionally attached to a deal, and why your relationship with the seller can be just as important as the numbers on the spreadsheet. From $4,000 micro-acquisitions to sourcing deals for buyers with millions of dollars behind them, Dev has seen both sides of the acquisition process. If you're thinking about buying an online business, especially for $100K or less, this conversation is full of lessons that could save you from making the same mistakes. 🎧 Hit play to hear what Dev would do differently if he could go back to his first acquisition.   Episode Highlights 05:04 – The $4K Sourcely AI Acquisition: How Dev Turned $500 MRR Into $5K+ MRR and Sold It for a Low Six-Figure Exit 06:24 – He Bought 6 More Businesses Under $10K Each: Why Acquiring Too Fast Became His Biggest Lesson 10:21 – Online vs. Offline Acquisitions: Why Stripe Makes Due Diligence Easier and How “Unofficial Revenue” Can Destroy a Deal 15:07 – The Deals He Walked Away From: Fake Information, Ghosting Sellers, and Red Flags That Changed Everything 18:16 – Why Dev Still Believes SaaS Is the Best Business Model, Even After AI Sent Smaller SaaS Multiples Nosediving 27:04 – The 200 Seller Calls Before His First Acquisition: Why Your Buy Box Should Start With Your Own Skills, Network, and Interests 31:44 – The 30-Day Due Diligence Test: Why You Should Approach Every Deal Like You're Taking Over the Business Tomorrow   Key Takeaways ➥ $4K can be enough to start. Dev turned his first $4,000 acquisition into a low six-figure exit in about 18 months. ➥ Six acquisitions in 18 months taught him to slow down. Buying businesses faster than he could integrate them created unnecessary complexity. ➥ 200 seller conversations built his acquisition edge. Dev spoke with roughly 200 sellers before closing his first deal. ➥ Your buy box should go beyond price and MRR. Skills, interests, networks, and competitive advantages should shape what you buy. ➥ 30 days of diligence can expose a bad deal. Dev recommends starting from a blank slate and examining every number, customer, and red flag. ➥ 50–70% upfront cash changes the risk. Dev typically structures deals so the seller retains meaningful financial incentive after closing. ➥ The seller can be valuable long after the deal closes. A strong relationship can make the first 90 days of ownership much easier.   About Dev Shah Dev Shah is a micro private equity investor and founder of Pocket Fund, a holding company built without outside capital. He started in 2023 by acquiring Sourcely.ai for $4,000, growing it into a business valued at $150,000 before exiting at a 37.5x return. Since then he's built a portfolio of SaaS, newsletter, and app acquisitions, and now helps search funds and private equity firms source and close deals in the $250K to $2M range.   Connect with Dev Shah ➥ https://www.linkedin.com/in/devlikesbizness/   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 happens when you buy a SaaS business for $5,000… only to discover the deal comes with a $12,000 security bill, a mountain of technical work, and a newborn baby? Andrew Kamphey was the number one user of Pigeon, a tiny SaaS app built inside Gmail that he genuinely loved. Then the founder announced he was shutting it down. So Andrew bought it. There was just one problem. The business was already making $0. And within days of sending the $5,000 payment, Andrew found out he was about to become a dad. A week later, his son was born prematurely and spent three days in the NICU. Meanwhile, Andrew was waking up every few hours to care for his newborn and sometimes restart the servers. Then came the $12,000 Google-required penetration test. What started as a tiny acquisition quickly became a crash course in what actually happens after you buy an online business. Technical headaches. Unexpected costs. Customer recovery. Infrastructure. And the reality that owning a business isn't always about growth charts and big wins. Sometimes it's just figuring out which fire to put out next. But Andrew didn't walk away empty-handed. After roughly six months, he had reduced the infrastructure costs, brought back paying users, improved the product, and eventually sold Pigeon for just over $30,000. And that's only part of the story. Andrew has also built and sold an industry newsletter with 15,000 subscribers, experimented with strategic acquisitions, and built Better Sheets into a business around Google Sheets, tools, templates, tutorials, and some seriously unconventional products. In this episode, Jaryd sits down with Andrew to unpack what his strangest acquisition taught him about buying businesses with little capital, why strategic value can matter more than traditional valuation multiples, what makes a small online business worth acquiring, and why simply asking an owner if they'd sell can open doors you never expected. Because sometimes the best acquisition isn't the one with the biggest revenue. It's the one you actually know how to make better. 🎧 Hit play - this is what a $5K SaaS acquisition, a $12K surprise bill, and a newborn baby can teach you about buying online businesses.   Episode Highlights 02:11 – Why Andrew Bought a SaaS He Was the #1 User Of After the Founder Announced It Was Shutting Down 05:12 – The $5K Acquisition With $0 Revenue: Why Traditional Valuation Multiples Didn't Make Sense 06:49 – The $12K Google Pen Test Nobody Expected: How One Compliance Cost Nearly Made the Tiny SaaS Impossible to Run 10:41 – From Acquisition to Fatherhood: How Andrew Found Out He Was Becoming a Dad 2 Days After Buying the Business 13:06 – The 6-Month Turnaround: Cutting Server Costs, Bringing Back Paying Users, and Selling the SaaS for $30K+ 20:41 – Why Andrew Keeps Building Weird Side Projects That Don't Make Money Yet - And Why That's Still Valuable 24:57 – The $36K Newsletter Exit: How a 15K, Subscriber Industry Audience Became a Strategic Acquisition Worth 3X Revenue   Key Takeaways ➥ Strategic value can beat revenue. Andrew bought Pigeon for $5K because he was its #1 user and understood its potential, even though it had $0 revenue. ➥ Cheap deals can hide expensive problems. The $5K purchase came with a $12K Google pen test, technical issues, and ongoing infrastructure costs. ➥ Ownership means owning every problem. Servers, security, APIs, compliance, and unexpected fires became Andrew's responsibility after the acquisition. ➥ Energy and focus matter more than time. Andrew eventually understood why the original owner walked away: sometimes another opportunity simply deserves your attention more. ➥ Small acquisitions can still create real returns. After about six months of improvements and cost-cutting, Andrew sold Pigeon for $30K+. ➥ Buy where you have an advantage. Knowing the product, customer, or market deeply can reveal opportunities that traditional numbers miss. ➥ Sometimes the best deal starts with asking. Andrew found opportunities through relationships, Twitter, and direct outreach,not just acquisition marketplaces.   About Andrew Kamphey Andrew Kamphey is the founder of Better Sheets, a Google Sheets tools and training platform he built in 24 hours and grew into a 4,000+ member business. A serial acquirer, Andrew has bought and exited multiple digital products, including Pigeon, an email CRM he rescued from shutdown and later resold on MicroAcquire. With a background spanning cruise ships, LA television, and indie newsletters, Andrew brings a scrappy, buyer-first approach to building a portfolio of small, profitable online assets. Connect with Andrew Kamphey ➥ https://www.linkedin.com/in/andrewkamphey/  ➥ https://bettersheets.co/  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.

AI might be one of the biggest reasons to buy an online business right now. Sounds crazy, right? Most buyers are doing the opposite. They’re seeing AI disruption and running for the exits. But that fear is creating something interesting: undervalued businesses that other buyers are too scared to touch. And not every online business is equally exposed. A generic SEO site? Dangerous. A content business selling information AI can generate for free? Huge red flag. But a sticky niche SaaS with recurring revenue, customer data and integrations? A physical-product e-commerce brand? A community people actually want to belong to? That’s a very different story. In this episode, Jaryd breaks down which online businesses AI could destroy, which ones could become dramatically more valuable because of it, and the exact things buyers should look for during due diligence. He also explains why ugly, outdated software might actually have a stronger moat than the shiny new AI tools everyone is talking about, and why customer inertia, switching costs and retention can matter more than how modern a business looks. Because the biggest AI risk might not be buying the wrong business. It might be being too scared to buy one at all. 🎧 Hit play — and find out where the real opportunities are hiding in the AI disruption.     Episode Highlights 00:42 – Why AI Fear Is Making Buyers Walk Away From Great Deals, And How That Fear Can Become Your Sourcing Strategy 03:01 – The AI Exposure Test: Which Online Businesses Are Most Vulnerable, And Which Ones Are Surprisingly AI-Resistant 07:30 – Why Niche SaaS With Sticky Customers, Data & Integrations Could Be Some of the Best Acquisitions Right Now 09:41 – The Physical-Product Advantage: Why E-Commerce Brands Can Use AI to Become Cheaper, Faster & More Profitable Without Being Replaced 14:20 – The 3.9x SaaS Opportunity: How Buyers Can Find Cash-Flowing, Recurring-Revenue Businesses Under $200K 16:37 – The 5 Due Diligence Questions That Reveal Whether AI Will Enhance or Destroy a Business 21:10 – Why the Ugliest, Most Outdated SaaS Businesses Can Have the Strongest Moats, And How Low Churn + Customer Inertia Creates Hidden Value 23:10 – The Mindset Shift Buyers Need: Why AI Should Be a Leverage Tool, Not a Reason to Sit on the Sidelines     Key Takeaways ➥ AI disruption doesn't automatically mean an online business is a bad acquisition. The real question is whether AI replaces what the business sells, or makes the business cheaper, faster, and better to operate. ➥ Information businesses are the most exposed. Generic content sites, SEO-dependent businesses, simple research tools, scraping services, and basic content creation can be vulnerable because AI can increasingly deliver the same information without requiring a click. ➥ Sticky businesses have a powerful moat. Niche SaaS with recurring revenue, customer data, integrations, workflow dependence, and low churn can remain highly resilient, even when the software looks outdated or clunky. ➥ Physical-product businesses have a major AI advantage. E-commerce brands selling real products can't simply be replaced by an AI model. Instead, AI can improve customer service, marketing, product descriptions, inventory forecasting, and operations. ➥ Customer switching costs matter more than a polished interface. A business with years of customer data and established workflows can be far more defensible than it looks. Ugly software with low churn can be an opportunity, not a warning sign. ➥ Due diligence needs an AI lens. Look at the traffic source, revenue model, content dependency, switching costs, and whether AI is an enabler or a competitor. And don't confuse “AI can replace this” with “AI will replace this.” ➥ The biggest opportunity may be the buyer who knows how to use AI. When a seller isn't leveraging AI, the right buyer can acquire the business and create value through automation, customer support, marketing, forecasting, analysis, and better systems, turning AI fear into acquisition leverage. 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 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 if you could beat a higher offer without paying more? Justin Butlion knows how. He’s completed five micro SaaS acquisitions, built a 10-app portfolio, and spends roughly three hours a week managing it. His biggest deal? $98,000 with 50% seller financing. And that’s where this gets interesting. Justin isn’t trying to outbid everyone. He’s learning how to become the buyer sellers want to choose. Move fast. Understand the seller. Know the industry. Structure the deal so it works for both sides. And seller financing? Justin calls it a powerful weapon. He reveals how he negotiated deals with financing at under 2% interest, why developers often make surprisingly motivated sellers, and how the right terms can let you acquire more without putting all your cash on the line. But the real edge starts before you make an offer. Justin breaks down exactly what he looks for in a micro SaaS: B2B customers, sticky recurring revenue, low churn, simple tech, built-in distribution, and minimal operational risk. He also walks through how he analyzes the SaaS funnel to spot opportunities that the headline numbers might completely miss. Then there’s the part most acquisition conversations skip. What happens after you buy? Justin gets brutally honest about cash flow getting squeezed by seller payments, the hidden cost of managing multiple small businesses, his costly lessons with U.S. business structures, and why bigger acquisitions may ultimately make more sense. Because the goal isn't to own the most businesses. It’s to build the most valuable portfolio without giving up your life in the process. If you’re buying micro SaaS, negotiating acquisitions, or looking for ways to win deals without simply offering the highest price, this conversation is packed with strategies you can actually use. 🎧 Hit play and learn how to become the buyer sellers choose, even when your offer isn't the highest.   Episode Highlights 03:09 – How $98K in Cash Sitting Inside an Analytics Agency Sparked a Five-Deal Micro SaaS Acquisition Strategy 05:27 – The Micro SaaS Sweet Spot: Why Justin Buys Simple B2B Apps With Recurring Revenue, Low Risk, and Built-In Distribution 10:58 – The Due Diligence Advantage: Why 10+ Years of SaaS Experience Can Be the Difference Between a Great Deal and a Disaster 16:01 – The 1.7% Churn Discovery: How a SaaS With Weak Paid Conversion Revealed Massive Upside Through Its Existing Distribution 17:42 – The Seller Financing Playbook: How He Bought a $98K SaaS With 50% Seller Financing at Under 2% Interest 20:49 – How to Beat Higher Offers Without Paying More by Becoming the Buyer Sellers Trust Most 37:21 – The Bigger Acquisition Strategy: Why Justin Is Rethinking Small Deals, Raising Capital, and Building Toward a $20K MRR HoldCo  Key Takeaways ➥ Seller financing can be a powerful acquisition tool. Justin used it in three of his five deals, including his $98K acquisition with 50% seller financing, allowing him to preserve cash and continue building his portfolio. ➥ The best SaaS acquisition isn't necessarily the fastest-growing one. Justin prioritizes simple B2B SaaS, low churn, recurring revenue, built-in distribution, and low operational risk over aggressive growth. ➥ Distribution can be more valuable than the software itself. When buying SaaS, you're acquiring an existing audience, customer base, brand, and recurring revenue stream, not just a piece of code. ➥ Due diligence should go deeper than revenue. Justin analyzes the entire SaaS funnel, from installs and signups to activation, paid conversion, and churn, to understand how healthy the underlying business really is. ➥ You can win deals without being the highest bidder. Moving quickly, understanding the seller's motivation, demonstrating acquisition experience, and reducing the seller's perceived risk can make you a far more attractive buyer than someone simply offering more money. ➥ Seller financing can also become a cash-flow trap. Financing makes acquisitions easier to complete, but excessive monthly payments can consume the business's cash flow and leave little room for growth or unexpected expenses. ➥ The ultimate goal isn't owning more businesses, it's building wealth without sacrificing freedom. Justin's experience has pushed him toward larger, higher-leverage assets while carefully weighing growth, risk, capital, time, and the lifestyle he actually wants.   About Justin Butlion Justin Butlion is the founder of Hawkeye Ventures, a holding company that has acquired 10 micro SaaS apps generating over $93K ARR since 2022. After 7+ years working inside B2B SaaS companies as a marketer, product manager, and analyst, Justin turned to acquisitions instead of reinvesting his agency's marketing budget into ads. He writes SaaS Decoded, sharing deal breakdowns, due diligence lessons, and acquisition strategy for operators and buyers.   Connect with Justin Butlion ➥ https://www.linkedin.com/in/justin-butlion-54912129/   ➥ https://www.saasdecoded.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 Joe Burrill Joe Burrill started buying and selling websites in 2012 with a $700 acquisition. He's since closed over 300 transactions totalling more than $6.8M on Flippa, where he's been named the platform's most successful broker. As founder of Just Website Brokerage, Joe is the only Flippa broker to hold every badge the platform offers. He's the rare operator who's lived on both sides of the deal table many times over.   Connect with Joe Burrill ➥ https://www.justwebsitebrokerage.com/  ➥ justwebsitebrokerage.com/2026    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.

What actually causes most business acquisitions to fail? It usually isn't the price. Or the financing. Or even the due diligence. It's what happens after the deal closes. Too many buyers spend months negotiating the perfect acquisition, then expect two businesses, two teams, two cultures, and two sets of systems to magically become one. That's where things start to unravel. In this episode, Jaryd sits down with Julie Keyes, Certified Exit Planning Advisor, author of Poised for Exit, and host of the Poised for Exit podcast, to unpack why integration is the most overlooked part of buying a business and why it's often the difference between creating value and destroying it. They dive into the biggest red flags buyers should spot before making an offer, why customer concentration and owner dependency can quietly kill a deal, and the simple question every acquirer should answer before buying another company: "Why are we doing this?" Julie also shares why culture matters just as much as cash flow, how successful buyers prepare long before signing the paperwork, and why the smartest acquisitions aren't about buying revenue, they're about creating a stronger business for everyone involved. Because the best acquisitions don't end at closing. That's where the real work begins. 🎧 Hit play to learn how to avoid the mistakes that sink most acquisitions and build a business that's worth far more after the deal than before.   Episode Highlights 04:15 – The 4 Biggest Deal Killers Buyers Spot Immediately: Customer Concentration, Owner Dependency, Weak Cash Flow and One-Product Businesses 11:08 – Why Most M&A Integrations Fail Within the First 1–2 Years After Closing and How to Avoid Becoming Another Statistic 15:45 – How One Strategic Acquisition More Than Doubled a Global Health Business With 19 Patents 17:35 – The $3–4 Million Business That Never Sold Because the Owners Couldn't Let Go of Their Identity 20:02 – Why Chasing the Highest Sale Price Can Leave Sellers With Less Money After Taxes 21:18 – Earnouts Explained: Why Staying 1–2 Years After Selling Can Protect Both the Buyer and the Seller 24:42 – More Than 80% of Enterprise Value Comes From Intangibles The Hidden Assets Most Buyers and Sellers Undervalue   Key Takeaways ➥ The success of an acquisition isn't decided at closing, it's decided during integration. The biggest mistakes happen when buyers underestimate how long it takes to align teams, systems, technology, leadership, and culture. ➥ Before buying any business, ask one simple question: "Why?" The strongest acquisitions are driven by strategic fit, not ego, revenue growth, or the desire to simply own a bigger business. ➥ Customer concentration, owner dependency, unstable cash flow, and limited product diversity are major red flags. These risks can significantly reduce a company's value and make future growth much harder for a new owner. ➥ The best buyers plan for people, not just profits. Keeping key employees engaged, building trust early, and improving their day-to-day experience can create far more value than cutting costs after an acquisition. ➥ Many deals fail because owners aren't emotionally prepared to sell. Some overvalue their businesses based on personal attachment, while others back out entirely because they haven't planned what comes after business ownership. ➥ The highest purchase price doesn't always produce the best outcome. Smart deal structures, tax planning, earnouts, and payment terms often have a bigger impact on the wealth both parties ultimately keep. ➥ More than 80% of a company's value comes from intangible assets. Strong leadership, loyal customers, experienced employees, efficient systems, brand reputation, and company culture are often far more valuable than the physical assets on the balance sheet.   About Julie Keyes Julie Keyes is a Certified Exit Planning Advisor (CEPA), founder of KeyeStrategies, and author of Poised for Exit. With 30+ years as an entrepreneur, she's helped hundreds of private business owners build enterprise value and exit on their own terms. She's a two-time EPI Thought Leader of the Year, inducted into the Exit Planning Hall of Fame, and hosts the Poised for Exit podcast. Julie is EPI faculty and trains advisors and business owners across the country on exit strategy.   Connect with Julie Keyes ➥ https://www.linkedin.com/in/juliekeyes/  ➥ http://keyestrategies.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.

A business can look profitable. The broker can call it “SBA pre-qualified.” The numbers can seem solid. And the deal can still be a disaster waiting to happen. Because financing doesn’t just help you buy a business. Structured badly, it can trap you in a deal that should never have closed in the first place. Ami Kassar has seen what happens when buyers get this wrong. One e-commerce acquisition he discusses was built around a single product. Just weeks after the transaction closed, a better product hit the market. The business was dead. And that’s only one version of the risk. Buyers jump into industries they’ve never operated in. They rely too heavily on one product, one supplier, or one sales channel. They treat lender pre-qualifications like guarantees. They rush because a seller wants to close fast. Or they take expensive “easy money” because speed feels more important than structure. That’s where deals get dangerous. In this episode, Jaryd sits down with Ami Kassar to unpack what buyers need to understand before taking on acquisition debt — from why SBA pre-qualifications may mean far less than you think, to what lenders actually look for in you and the business you’re buying. They break down how to improve your fundability before the right deal appears, why post-close liquidity matters, when seller involvement can help get a transaction financed, and why working capital should be part of the conversation before you ever sign on the dotted line. But the bigger lesson goes beyond getting approved. Ami believes the smartest financing strategy is the one that gives you maximum flexibility — because the goal isn’t to build the biggest portfolio, take on the most leverage, or grow at a pace that destroys your sleep. It’s to structure a deal you can actually live with. 🎧 Hit play before you finance your first — or next — online business acquisition. This conversation could save you from the kind of deal that looks exciting at closing… and becomes expensive the moment reality hits.   Episode Highlights 03:16 - The Question Every Buyer Should Ask Before Taking on Acquisition Debt: What Could Bring This Business to Its Knees? 06:14 - Why an “SBA Pre-Qualified” Business May Not Be Financeable When a Real Buyer Shows Up 07:48 - The E-Commerce Risk That Can Kill an Acquisition Weeks After Closing: One Product, One Channel, No Backup 12:42 - Why the Lowest Monthly Payment Can Matter More Than the Lowest Interest Rate When Structuring a Deal 16:14 - The Fast-Close Financing Trap: Why a Seller Pushing to Close in Weeks Should Immediately Raise Questions 18:06 - What Lenders Actually Look at Before Funding You: Clean Books, Tax Returns, Credit and Your Existing Businesses 30:28 - The Predatory Lending Trap: How “Fast Money” Can Put a Stressed Business on a Treadmill That Kills It   Key Takeaways ➥ Ask what could bring the business to its knees before taking on acquisition debt. ➥ “SBA pre-qualified” does not mean guaranteed financing. The buyer, business, and lender appetite still matter. ➥ Lenders assess both the deal and the buyer—from industry experience to credit, tax returns, and financial discipline. ➥ The best financing structure creates flexibility through manageable payments, liquidity, and access to working capital. ➥ Rushing a deal can be costly. Fast closes, weak due diligence, and expensive short-term financing are major warning signs. ➥ Cash reserves matter after closing. Buyers need enough runway to handle setbacks without putting the business at risk. ➥ More debt and more acquisitions do not always mean more success. Build around your risk tolerance, lifestyle, and long-term goals.   About Ami Kassar Ami Kassar is the founder and CEO of MultiFunding and author of The Growth Dilemma. For over 25 years he's helped entrepreneurs across the US unlock creative, cost-saving financing solutions — from SBA loans to alternative debt structures — to grow companies, improve cash flow, and restructure debt responsibly. He advises the White House, Treasury Department, Congress, and the Federal Reserve Bank, and is frequently quoted in the Wall Street Journal, Forbes, and the New York Times. He writes a weekly column for 21 Hats   Connect with Ami Kassar ➥ MultiFunding LinkedIn  ➥ MultiFunding Facebook ➥ MultiFunding Instagram: @MultiFunding    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.

Finding a great business is only half the battle. The harder part? Convincing a lender that you're the person who should own it. That's where most acquisitions quietly fall apart. In this episode, Jaryd is joined by Jared W. Johnson, the top individual SBA loan producer in the United States, who's helped fund more than $800 million worth of business acquisitions. But this isn't just another conversation about lending. Jared has been on both sides of the table. He recently acquired a $600,000 eCommerce business himself. What caught his attention wasn't perfect systems or polished financials. It was the opposite. A business with outdated processes, inventory tracked entirely from memory, and obvious operational gaps that most buyers would see as red flags. He saw upside. Together, Jaryd and Jared unpack how the deal came together, why the business was relocated across states, how a 3PL simplified operations, and why keeping one long-term employee became one of the smartest decisions they made after the acquisition. They also pull back the curtain on how lenders really think. Why do buyers with strong incomes still get declined? What makes someone trustworthy in the eyes of a bank? Does your personal spending matter? And when a business has valuable assets like an email list, loyal customers, strong SEO, or a large social following, how much weight do lenders actually give them? Whether you're preparing to buy your first business or looking to finance your next acquisition, this episode gives you a clearer picture of what separates buyers who get approved from those who don't. The best deals don't always go to the highest bidder. They usually go to the buyer who's prepared. 🎧 Hit play and discover what lenders are really looking for before they ever approve a business acquisition loan.   Episode Highlights 04:14 - Inside Jared's $600K eCommerce Acquisition: Why He Bought a Business Most Buyers Would Walk Away From 12:36 - From California to Texas: How They Relocated the Business, Switched to a 3PL, and Kept Operations Running Smoothly 21:42 - The Top Reasons SBA Loans Get Declined - Even When the Business Looks Like a Great Deal 24:26 - How to Make Lenders Believe You're Ready to Buy Your First Business (Even Without Owning One Before) 27:45 - The "Leaky Bucket" Test: Why Your Personal Finances Can Make or Break an SBA Approval 31:09 - How Banks Really Value Email Lists, SEO, Social Media, and Other Intangible Business Assets 36:18 - The Simple Move That Can Turn a "Maybe" Into a Loan Approval When You're Short on Experience   Key Takeaways ➥ The best acquisitions often hide behind messy operations. What looks inefficient to most buyers can become an opportunity with the right systems and execution. ➥ Lenders don't just evaluate the business - they evaluate the buyer. Your experience, preparation, and financial discipline all influence loan approval. ➥ First-time buyers can still secure SBA financing by demonstrating industry knowledge, a clear plan, and the ability to operate the business successfully. ➥ Retaining experienced employees can be one of the smartest post-acquisition decisions. Institutional knowledge is often more valuable than documented processes. ➥ Your personal finances matter. Lenders view your spending habits, savings, and cash reserves as indicators of how you'll manage a business. ➥ Email lists, SEO, customer databases, and social media add value - but lenders focus on how they support consistent cash flow, not just their size. ➥ Buying the business is only the beginning. Long-term success comes from continuously improving operations, learning the business, and investing in the right people.   About Jared Johnson Jared W. Johnson is the biggest individual SBA producers in the United States, having closed over $800 million in SBA loans across his 15+ year career, the majority being M&A and business acquisition deals. As VP and Senior Business Development Officer at First Internet Bank, he's a two-time Coleman Publishing SBA BDO of the Year. He's also a business owner himself, having personally acquired and exited a manufacturing company. He hosts the Before You Buy or Sell a Business podcast.   Connect with Jared Johnson ➥ https://www.linkedin.com/in/jaredwjohnson/    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 evaluating a business purchase today fixates on the same thing. Can this survive AI? Wrong lens. Wrong era. Wrong way to size up a deal. Tony Xu ran product and engineering at Flippa for five years before taking over as CEO. He's sat behind the scenes of thousands of transactions, tracked which categories exploded and which quietly faded, and seen firsthand what happens once AI actually touches a working business. And he'll say something most of the doom content circulating right now won't. AI isn't hunting your business down. It's clearing out the grunt work inside it. Photo editing. Listing copy. Animation that used to demand a full production team. Rough drafts of ad creative. Tasks that used to consume a founder's entire week now take minutes. Treating that as a threat misses what it really is. A head start. But here's the part almost nobody admits out loud. Nothing essential has changed. Who you reach. What people remember about your brand. Whether your customers stick around. Claude can write your listing copy. It can't earn you a decade-long relationship that gets your product onto a shelf. It's not handling your cash flow. It's not securing your credit line. It's not the reason someone buys from you twice. The businesses pulling ahead right now aren't the ones hiding from AI. They're run by people who know precisely where its usefulness ends and the real value begins. In this episode, Jaryd talks with Tony about what's really moving inside Flippa's marketplace. Why $250K to $5M has become the sweet spot for the sharpest buyers. How specialist operators are walking into neglected businesses and multiplying category growth in a matter of months. The difference between a roll-up play and a specialist play. And why chasing "AI-proof" is precisely the wrong instinct to bring into diligence. They also break down the two warning signs that should end a deal immediately. How a buyer's own comfort with AI can cut a year-long ramp-up down to half that. And why the businesses that seem the most behind the curve might actually be the cheapest assets on the whole platform. The buyers nervous about AI aren't wrong to be paying attention. They're just tracking the wrong risk. Tony isn't. 🎧 Hit play. Straight from the person who built the platform. No hype, no scare tactics, just where the real opportunity is sitting.   Episode Highlights 02:55 - Inheriting the Throne: Taking Over as Flippa CEO After Eight Years of Blake's Leadership 04:05 - The Globalization of Flippa: Why 60% of European Businesses Are Now Being Bought by Americans 05:26 - Multi-Currency, AI Translation, and 158 Payment Options: The Infrastructure Behind Flippa's Cross-Border Boom 06:59 - From Sub-$10K Domains to $250K-$5M Deals: How the Sweet Spot of Flippa Acquisitions Has Shifted Over a Decade 08:49 - Why E-Commerce Remains the Gold Standard for First-Time Buyers and How to Pick the Right Vertical 11:30 - The 450,000-Buyer Marketplace: How AI Recommendations and Watchlists Make an Overwhelming Number of Listings Feel Personal 14:55 - From the Serbian DJ's 140-Business Roll-Up to Specialist Buyers Who Bring Their Own Distribution Network 22:10 - Tony's Contrarian Take on AI: Why It's Not a Strategy, Just an Operational Tool Everyone Will Eventually Use 26:40 - The K-Shaped Productivity Curve: Why AI Makes the Best Operators Two to Three Times More Effective 29:40 - What AI Still Can't Touch: Why Distribution, Brand, and Customer Trust Remain the Real Choke Points of Value 36:43 - Tony's First-Time Buyer Checklist: Distribution, Brand Personality, and Operational Soundness Before You Sign Anything 38:25 - The Two Dealbreakers: Regulatory Red Flags and Why You Need a Real Handover Plan With the Founder 40:49 - Flippa's New AI-Powered P&L Builder and Data Room: What's Coming Next for Sellers and Buyers   Key Takeaways ➥ AI isn't a strategy. It's just the next operational tool everyone adopts within months, the same way FBA and 3PLs did. Whatever edge it gives you today gets competed away fast. ➥ The best operators are now two to three times more productive than they were a year ago. AI doesn't replace the founder, it supercharges them. That turns a twelve-month turnaround into six. ➥ Nobody's handing Claude their ad budget and walking away. Distribution, customer trust, cash on the balance sheet, the real choke points of value are still completely untouched by AI. That gap is where the money is. ➥ Specialists beat generalists every time. Flippa's fastest-growing categories are led by people with niche expertise, not just capital. Find the vertical your skills can supercharge. ➥ You don't have to love the product to love the deal. Plenty of buyers acquire businesses they have zero personal interest in because they're hooked on the operations, the numbers, and the upside. ➥ Two things kill a deal fast: regulatory landmines and no handover plan. No license compliance or no founder transition period are both deal-breakers worth walking away from. ➥ AI is a tailwind for content, a wash for e-commerce, and a coin flip for SaaS. It all comes down to execution speed. Ship faster, cut churn, win. Sit still, and AI just made your competitor's job easier too.   About Tony Xu Tony Xu is the CEO of Flippa - the world's #1 marketplace for buying and selling online businesses. With a background spanning economics, accounting, and a CPA qualification, Tony spent years as Flippa's Head of Product and Engineering, architecting the platform tools that have powered hundreds of thousands of digital business transactions. He's led the development of game-changing innovations including LaurenAI (Flippa's AI-powered deal sourcing engine), the Buyer Directory, and Flippa's AI-driven valuation tools - making institutional-grade M&A accessible to everyday entrepreneurs.   Connect with Tony Xu ➥ Flippa.com (affiliate link, not for Eden) ➥ https://www.linkedin.com/in/tony-x-62037498/    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 people trying to win at SEO are asking the wrong question. How do I get my traffic back? Wrong question. Wrong game. Wrong decade. Steve Wiideman has thirty years in this industry. He's seen every update, every panic, every agency pivot. And he'll tell you something most people charging you monthly retainers will never admit. The traffic isn't coming back. AI overviews are eating clicks before you even show up. Agentic commerce means people are buying inside ChatGPT and YouTube without ever touching your website. Zero-click isn't coming. It's here. It's done. It's the new normal. And most agencies are still selling you 2019 with a new logo. But here's the thing nobody's saying out loud. The fundamentals never broke. The shortcuts did. Content farms. AI-generated blog factories. Link blasters. Agencies who promised more content meant more traffic. Google's March update didn't come out of nowhere. It was a warning that had been building for years. And it landed hard. In this episode, Jaryd sits down with Steve to talk about what's actually happening. Why the businesses winning right now stopped chasing rankings entirely. How one sentence in a Google Maps review took a brand new burger joint to number one in two days. What agentic commerce means for your revenue model. And why single-source dependency on Google is the single biggest risk any online business is carrying right now. They also get into why twenty real brand fans beat an entire link-building team. How to build content in a shrinking-click world. And the mindset shift separating businesses that are growing from the ones watching their dashboards collapse. The agencies lying to you about AI aren't villains. They just don't know what else to sell you. Steve does. 🎧 Hit play. Thirty years of SEO truth. No fluff. No spin. Just the conversation your agency should have been having with you a long time ago.   Episode Highlights 03:01 - Why Google's Latest Updates Actually Confirm That Nothing Fundamental Has Changed About Great SEO 05:53 - The Zero-Click Reality: Why Your Lost Traffic Isn't Coming Back and What to Do Instead 07:49 - EEAT, AI Content, and the March Update: What Google Is Really Saying to Content Site Owners Right Now 08:53 - The Multimodal Content Approach: How Smart Brands Are Scaling Blogs Beyond Just Written Articles 13:21 - Why Blasting Your Brand Across Every Platform Is a Trap and the Two to Three Platform Rule That Actually Works 17:50 - The Hard Truth About Traffic: Why Chasing Old Click Numbers Is the Wrong Game Entirely 24:26 - Agentic Commerce and the Future of Google: How People Will Buy Without Ever Visiting Your Website Again   Key Takeaways ➥ The traffic isn't coming back. Full stop. The businesses winning right now accepted that early and stopped wasting energy trying to recapture something that no longer exists. They moved on. You should too. ➥ SEO was never about gaming Google. It was always about people. If ten results show up in a search, the brand that earns the click, delivers something real, and gets remembered wins. That hasn't changed. It never will. ➥ Seventy percent or more of your traffic from one source isn't a business. It's a bet. And right now that bet is paying out less than it ever has. Single-source dependency on Google is the biggest hidden risk sitting inside most content businesses today. ➥ One authentic sentence in a Google Maps review took a brand new restaurant to number one in two days. That's not luck. That's semantic triples working exactly as intended. What other platforms say about you in real conversations on real pages matters more than most people realize - to Google and to every LLM pulling citations. ➥ Publishing great content and moving on is the old game. The new game is lighting a fire around every piece you create. Get it in front of real people fast. The speed of early engagement signals more than most SEOs will ever tell you. ➥ People are already buying inside ChatGPT and YouTube without ever visiting a website. Agentic commerce isn't coming. It's here. And if your business isn't set up to sell where your customers already are, you're invisible at the moment that matters most. ➥ Traffic was never the point. Revenue was. Clicks don't pay bills. Customers do. The fastest mindset shift any online business owner can make right now is stopping the obsession with the dashboard and starting to measure what actually matters - people buying, returning, and telling others.   About Steve Wiideman Steve Wiideman - known as "SEO Steve" - is the founder of Wiideman Consulting Group and co-author of SEO: Strategy & Skills, a college textbook used at universities across the US. With nearly 30 years in search, he's helped brands like Disney, Skechers, Public Storage, and Honda dominate organic traffic. A practitioner, scientist, and adjunct professor at UCSD and CSUF, Steve specialises in multi-location and e-commerce SEO and is one of the most trusted voices on navigating SEO in the era of AI search.   Connect with Steve Wiideman ➥ https://www.wiideman.com/ ➥ https://www.stevewiideman.com/ ➥ https://www.linkedin.com/in/seoexpert/    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.