Buying Online Businesses Podcast

What does it actually look like to buy 10 online businesses over 14 years - and still be standing? Not the highlight reel. The chargebacks, the 95% traffic drops, the seller-financed deal you hand back four months in because you simply can't make it work. The slow, painful realization that passive income was never really the point - ownership was. Brock Yates has been buying online businesses since 2012, starting with a $3,000 turtle website he found on Flippa with zero SEO knowledge and zero plan. By the time he quit his day job in Switzerland to go full-time, he had a portfolio of content sites generating more than his salary. Then the Google Helpful Content Update hit. And then ChatGPT changed everything. In this episode, Brock doesn't just share what went wrong - he shares what he actually did to crawl back, adapt, and build something more resilient on the other side. In this episode, you'll learn: Why Brock handed a $220K–$280K e-commerce acquisition back to the seller after four months - and what he'd do completely differently today The one thing every first-time buyer underestimates: the seller's institutional knowledge and what disappears the moment they walk out the door How a 95% traffic drop forced him to rethink content sites entirely - and why the turtle website outlasted everything else in his portfolio The WooCommerce vs. Shopify decision that's shaping his entire content-to-commerce strategy now How he used ChatGPT to build a free tool in 20 minutes that took a brand-new GM vehicle site from zero to 1,000 email subscribers - and counting Why buying a business to "own for 10 years" changes every decision you make from day one The niche-selection mistake that kills most content sites before they ever have a chance to grow Whether you're sitting on a content site wondering what to do next, or you're a first-time buyer trying to avoid the mistakes most people only learn the hard way - this conversation is one of the most honest, practical accounts of what building an online portfolio actually looks like across a decade.

What if the biggest risk right now isn’t a bad deal - but doing nothing? While most buyers wait for the AI dust to settle, the ones who understand what’s happening are quietly buying assets at discounts that won’t exist a year from now. The shift isn’t theoretical. Digital Trends lost 90% of its Google traffic - from 8.5M clicks to 65K. HubSpot lost nearly half its organic traffic in two months. Atlassian dropped 35% as enterprise usage declined. Salesforce fell 28%. And Monday.com replaced a 24-person sales team with AI in minutes. This has already happened. So the real question isn’t if AI is reshaping the market - it’s whether you know which businesses are still worth buying, how to price the risk, and when to walk away. In this episode, Jaryd breaks down how to spot hidden value in “declining” assets, why some SaaS models are collapsing, and how AI risk can be used as leverage - not fear. Because the buyers winning right now aren’t panicking or waiting. They’re moving with a strategy.

Most people think buying businesses is a numbers game. Ace Chapman has done 200+ acquisitions - and he'll tell you the numbers are almost never the point. Ace has been in this game since the dot-com bubble. He almost sold a stock market simulator to a little Nebraska company called Omaha Securities - before it became Ameritrade. He got out of a real estate business right before 2008 hit. He's not lucky. He's built a framework for thinking about business ownership that most acquisition guys never arrive at, no matter how many deals they close. But here's where it gets interesting. Right now, while everyone else is hunting online businesses in the U.S., Ace is doing something completely different - buying offline deals in Latin America, where business brokers don't exist and most owners don't even know selling is an option. Hotels. Spas. Mental health clinics. Panama. Colombia. Argentina. He walked into a hotel recently and heard the front desk pitch his own spa to a guest checking in. In this episode, Jaryd sits down with Ace to unpack why he thinks every business is just inventory - and why holding on too long is the real risk most buyers never talk about. How he structures equity deals so he never has to build anything from scratch. And what a real portfolio actually looks like when you stop confusing operating businesses with wealth. Most buyers are waiting for the market to calm down before they make a move. Ace just went and found a completely different market - one where nobody else is even looking.

What if the best acquisition you'll ever make is the one nobody else bothered to look at? That's not a rhetorical question. That's exactly how Karl Hughes bought his first agency. While every other buyer was refreshing broker listings and fighting over the same tired deals, Karl built a spreadsheet, started cold DM-ing podcast production founders on LinkedIn, and had fifty conversations most people would've deleted without a second thought. No broker. No bidding war. No competing offers. Just Karl, a thesis, and the patience to work a room that nobody else had walked into yet. One of those conversations turned into a sub-million-dollar acquisition at 2.7x SDE -a healthy, cash-flowing business with clients who'd been around for five-plus years. The seller had never seen a competitor's P&L in his life. Karl had seen twenty before he ever made the call. But here's where it gets interesting. That deal was just the beginning. Since then, Karl has been quietly building a portfolio of niche marketing agencies -the kind that are too small for private equity, too owner-dependent for most buyers, and too overlooked for anyone to notice the opportunity hiding inside them. Financing deals creatively. Targeting founders who are ready to move on. And figuring out in real time what it actually takes to merge two similar agencies without torching the clients that made them worth buying in the first place. In this episode, Jaryd sits down with Karl to unpack why small agencies rarely get a real exit -and why that's the opportunity. How Karl showed a seller the actual debt math before making an offer and closed with trust instead of pressure. And what he'd do completely differently if he had to start the integration process over again from day one. Most buyers wait for a clean deal to fall into their lap. Karl just built his own pipeline and went to find it.

What if you could sell a business, get it handed back to you for $100, flip it again for a profit -and use that whole experience to build something even bigger? That's not luck. That's Qayyum Rajan. In this episode, Jaryd sits down with Qayyum -founder, developer, and holdco builder -who turned a single LinkedIn cold message into a PE exit, watched that same PE firm quietly forget his business existed, bought it back for $100, and relisted it on MicroAcquire while two buyers bid against each other in real time. But here's where it gets really interesting. After the exit, while everyone else was running away from content sites -Google had just torched their traffic with the helpful content update -Qayyum was running toward them. Buying burnt-out founders' blogs for $10K–$50K. Merging them. Building newsletters nobody had touched. Going faceless on YouTube. And quietly turning the whole thing into a cash-flowing media holdco that made back its entire investment in nine months. You'll learn how he evaluates and closes acquisitions in under 24 hours, why "domain authority and love" are his two non-negotiables, what it actually looks like to consolidate three sites under one domain without destroying the traffic -and why he thinks the biggest opportunity in content right now is hiding inside the businesses everyone else already walked away from. Most buyers wait for the perfect business. Qayyum just knows how to read the ones everyone else missed.

What if the business everyone else passed on was actually the one? Most first-time buyers obsess over finding the perfect business - but the ones who actually close deals? They obsess over reading the business correctly. In this case study episode, Jaryd Krause sits down with Jan, a Buying Online Businesses graduate who went from consuming YouTube content and podcasts to acquiring a six-figure health and beauty e-commerce brand - and lived to tell the full, unfiltered story. Jan brought something most buyers don't: seven-plus years of digital marketing and DTC experience. And she used every bit of it to spot the green flags hiding inside what most buyers would have walked away from. You'll learn how Jan evaluated over 100 listings, deep-dived on 30 businesses before finding the one, negotiated inventory she didn't want out of the purchase price, and immediately unlocked growth through paid ads and an underutilized email list the previous owners barely touched. You'll also hear why red flags aren't dealbreakers - they're filters - and how the right background can flip a liability into your biggest competitive edge. If you're a first-time buyer trying to figure out what "good" actually looks like before you sign anything, hit the

What if you never needed to scale big - to sell big? Stuart Faught has done it 20 times. And he'll tell you - that's exactly the wrong way to think about it. Because what most SaaS founders don't realize… is that the real money isn't in building forever. It's in knowing exactly when to let go. Like the business he built, took to 100K ARR… and sold in 30 days flat. Or the deals where buyers showed up with zero-down offers and five-year payment plans… and got politely - but firmly - shown the door. Or the biggest mistake first-time SaaS buyers make - falling in love with the tech… when the only thing that actually grows the business is sales. In this episode, Jaryd Krause sits down with Stuart Faught - serial micro SaaS entrepreneur who has built and exited over 20 software businesses across verticals like dental, HVAC, med spas, and home care. All bootstrapped. All profitable. All sold. And this one gets real. Into why Stuart never scales past 100K ARR before selling - and why that's a feature, not a limitation. Into what he'd look for if he were buying a SaaS business tomorrow - and the red flags that would make him walk. Into why non-technical buyers are actually better positioned to grow software companies than most people think. But more importantly… Stuart breaks down the exact repeatable system behind 20 clean exits - what makes a deal close fast, what kills it dead, and why simplicity is the most powerful thing a seller can offer a buyer. No fluff. No theory. No "someday I'll do it big." Just 20 exits deep of hard proof - from someone who's figured out the game… and keeps winning it.

Most people think buying a business is just about finding a “good deal.” Kevin Peterson has done over 50 acquisitions - and he’ll tell you that’s exactly how people lose money. Because what brokers don’t tell you… is that the real risk isn’t the numbers? It’s what’s missing behind them. Like the SaaS deal that looked perfect on paper… until the entire team walked out right after closing. Or the “growth opportunity” that was actually just an audience no one had ever monetized. Or the biggest trap of all - buying a business without a clear thesis… and hoping it works out later. In this episode, Jaryd sits down with Kevin - founder of Webfolio Management - who’s spent the last 12+ years acquiring, operating, and scaling digital businesses across SaaS, content, and eCommerce. And this one goes deep. Into the real due diligence signals most buyers miss. Into how AI is quietly changing what businesses are worth buying - and which ones are becoming obsolete. Into the hidden risks inside “easy wins” like audience monetization and roll-ups. But more importantly… Kevin breaks down the exact thinking behind building a portfolio that doesn’t just grow - but actually survives. No hype. No shortcuts. No theory. Just hard-earned lessons from someone who’s done the deals, made the mistakes… and kept going anyway.

Most founders think selling a business is about getting the highest offer. Nathan Gwilliam spent 30 years learning why that belief is exactly what destroys exits. Three businesses built. Three exits are closed. And a front-row seat to some of the most painful – and profitable – lessons the entrepreneurial world rarely talks about out loud. Like the time Disney came knocking... and his partner wouldn't even let them see the financials. Or the earn-out that looked like a windfall on paper - until someone else was making all the decisions. Or the phone call on a Sunday morning, right before church, that changed everything about why he sold Adoption.com. In this episode, Jaryd sits down with Nathan – the founder behind the most visited adoption platform in the world – for one of the most honest, human, and genuinely surprising conversations we've had on this show. Because yes, you'll get the tactics. The roll-up acquisition strategy that turned his biggest competitor into his biggest asset. The 50/50 partnership trap that quietly kills deals before they ever start. The exact moment a founder should seriously consider selling – even if the timing feels wrong. But this one goes somewhere most business podcasts are too scared to go. Into the Sunday morning phone calls. Into making decisions from love instead of fear. Into what it actually costs – emotionally, financially, spiritually – to build something real and then let it go. Nathan doesn't dress it up. He doesn't hide the mistakes. And he doesn't pretend the journey was clean. And that's exactly what makes this one unmissable.

What does it actually look like to buy a business with zero margin for error? No safety net. No backup plan. A full-time military career, seven kids at home, and a lender who pulled out mid-deal. That's exactly where Michael Simpson found himself. In this episode, Jaryd Krause sits down with Michael Simpson - a National Guard serviceman who bought an 18-year-old e-commerce business using SBA financing, survived a near-collapse due diligence process, and came out the other side with a real, running business. But he's not here to tell you it was amazing. He's here to tell you the truth. Here's what's covered:

What if the thing standing between you and total lifestyle freedom… was just one business acquisition? A former respiratory therapist and a software developer – no entrepreneurial experience, no roadmap, no idea what they were doing – decided to bet on themselves anyway. And now? They're running a lean team of 11 VAs from wherever in the world they feel like being that week. Guatemala last month. St. Kitts for their anniversary. Belize next. You get the picture. In this episode, Jaryd Krause sits down with Alan and Mel, a husband-and-wife duo who tried every side hustle in the book – financial lending, credit repair, online teaching – before discovering that buying an existing online business was the shortcut they'd been exhausting themselves looking for. They used SBA financing to acquire a $1.2M business with just $65K out of pocket. They inherited 2 VAs and a chaotic operation. They were working 60-hour weeks at the start. And then – systematically, strategically – they rebuilt it, scaled it, and sold it. Profitably. Now they're already under LOI for their next deal. Here's what makes their story different though. Neither of them had ever owned a business before. One was in healthcare. One was in tech but still didn't think you could buy something you couldn't physically touch. They were scared, skeptical, and figuring it out in real time. Sound familiar? If you've ever wondered whether someone like YOU could actually pull this off – this episode is your answer. Hit play. You'll want to hear this one.

Most buyers are still doing due diligence like it's 2015. And the ones who know how to use AI? They're finding better deals, faster, and you'd never even know they were looking. In this episode, Jaryd sits down with Haytham Allos, M&A strategist, AI specialist, and one of the minds behind one of the world's first AI-powered law firms, to pull back the curtain on what's actually happening right now at the intersection of artificial intelligence and buying businesses. And it gets wild. We're talking AI agents that evaluate deals. Smart contracts that close them. Fractionalised ownership that lets someone invest in a business for as little as $50. A future where your AI agent negotiates with the seller's AI agent, and a human just says yes or no at the end. But before we get there? Haytham breaks down what's happening right now. Why most buyers are still flying blind, why AI without the right prompting is actually dangerous in a deal, and the one thing that kills more mergers than bad financials ever will. You'll discover why prompt engineering is the most underrated skill in acquisitions today, how to use AI to get an unfair edge in due diligence without replacing your gut instinct, and exactly where the smart money is already moving. This isn't theory. This is where M&A is heading, and the buyers who understand it now are going to own the next decade. Hit play. Your competition probably already has.

Buying a $10M–$100M online business isn’t just about having capital. It’s about relationships, structure, leverage, and knowing how the game is really played behind closed doors. In this episode, Jaryd Krause sits down with Emmet Kilduff, founder of The Fortia Group and former investment banker at Morgan Stanley, to unpack how serious online acquisitions actually get done in the $10M to $100M range. After 25 years in M&A, Emmet pulls back the curtain on what separates institutional buyers from everyday acquirers, and why trying to “figure it out yourself” is one of the most expensive mistakes you can make. You’ll learn: The 3-stage “Flirt, Date, Marry” framework elite dealmakers use to build acquisition relationships years before a deal closes Why the best buyers pitch sellers, and how to create a buyer deck that makes founders want you The real funding structures used by strategics, private equity, aggregators, and search funds What’s changed since the 2021 acquisition boom, and why 100% upfront deals are basically extinct The truth about earn-outs (and why most are designed for buyers, not sellers) Why recurring revenue businesses command premium multiples, and how valuation arbitrage actually works How to transition from operator to owner so you can think strategically and fund bigger moves This is not theory. This is how real capital allocators think. If you want to understand how serious acquirers finance deals, structure terms, protect downside, and build relationships that lead to eight- and nine-figure exits, this episode is your behind-the-scenes briefing. If you’re planning to buy, sell, or scale an online business and want to understand how institutional-level M&A actually works, hit the “Play” button. Episode Highlights 03:12 Why Even $10M Buyers Shouldn’t Go It Alone 05:08 The “Flirt, Date, Marry” Framework for Closing Bigger Deals 08:41 How Smart Buyers Pitch Sellers (And Win Trust Fast) 12:06 The Truth About Earn-Outs (And Why Sellers Should Be Careful) 18:47 The Three Types of Institutional Buyers in the $10M–$100M Range 23:55 Why Recurring Revenue Changes Everything in Valuation 28:36 The Strategic Conversations That Should Happen Before Price Is Discussed 35:44 From Operator to Owner: Making the Shift to Strategic Thinking 40:27 Building an Advisory Board That Actually Moves the Needle Key Takeaways ➥ Buying a $10M–$100M online business is as much about relationships and strategy as it is about money. ➥ Use the “Flirt, Date, Marry” framework: build trust early, share information progressively, and finalize only when both sides are aligned. ➥ Strong buyers actively pitch sellers—your experience, vision, and team matter just as much as your capital. ➥ Typical deal structures include 60–80% upfront with the balance via earn-outs, equity rollover, or milestone-based deferred payments. ➥ Structuring earn-outs around revenue, not profit, reduces disputes and protects long-term relationships. ➥ Recurring revenue businesses (SaaS, subscriptions, memberships) command higher multiples and offer more predictable financing. ➥ Advisory panels and mentors accelerate decision-making, reduce risk, and boost credibility with sellers. ➥ Transitioning from operator to owner requires delegation, trust, and strategic focus over day-to-day management. ➥ Patience, preparation, and network-building are the hidden factors that make or break acquisition success. About Emmet Kilduff Emmet Kilduff is the Founder of The Fortia Group, an M&A advisory firm specializing in the sale of eCommerce brands and digital agencies. With a background at leading Wall Street investment banks including Morgan Stanley, Emmet brings institutional-level M&A, valuation, and deal-structuring expertise to small and mid-market online businesses. Through Fortia, he has advised founders, buyers, and investors on acquisitions across the UK, US, and international markets, helping them navigate financing, positioning, and exits with professional rigor. On this episode of the Buying Online Businesses Podcast, Emmet shares how sophisticated buyers think about funding acquisitions, structuring deals, and avoiding the common mistakes that derail first-time online business buyers. Connect with Emmet Kilduff ➥ https://www.linkedin.com/in/emmettkilduff/ ➥ https://thefortiagroup.com/ Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ Buy & Sell Online Businesses Here (Top Website Brokers We Use)

Online business acquisitions aren’t won by the highest bidder - and they’re definitely not lost for the reasons most buyers think. In this episode of the BOB Podcast, Jaryd Krause sits down with Ryan Condik - serial entrepreneur, M&A advisor at Quiet Light, and founder of Let’s Buy a Business - to unpack what actually determines who wins (and who loses) in competitive acquisition processes. Most buyers assume it all comes down to price. Just offer more and you win, right? Not exactly. In real-world M&A, things like certainty, speed, positioning, and creativity often matter more than a bigger number. Ryan shares behind-the-scenes stories from competitive deals, including why some buyers lost over small term differences, how one buyer won simply by building a genuine relationship with the seller, and why “certainty of close” can be far more powerful than offering an extra 10%. You’ll learn: Why sellers often choose lower offers - and what they’re really evaluating How certainty, speed, and clean deal structures give buyers a serious edge Why trust and relationships can outweigh valuation The common buyer mistakes that quietly kill deals How creative structuring (including equity rollovers) can change the outcome Why knowing your value-add before submitting an LOI shifts the entire negotiation Whether you’re buying your first online business or competing for premium assets in a crowded market, this episode breaks down what separates serious acquirers from hopeful bidders. In M&A, price gets attention - but certainty wins deals.

The internet isn’t being searched the same way anymore—and most businesses haven’t caught up. In this episode of the BOB Podcast, Jaryd Krause welcomes back Rad Paluszak to explore the transition from SEO to GEO (Generative Engine Optimization) and what it means for founders, operators, and investors navigating an AI-driven world. Instead of ranking pages, AI answer engines are ranking entities, brands, and trust. Rad explains why traditional SEO playbooks are breaking down, how AI engines source and rotate answers, and why brand mentions across the web now matter more than links ever did. You’ll learn: Why AI engines rarely repeat the same sources—and how that changes traffic forever How brand authority is built through mentions, associations, and personal brands Why being listed alongside established brands can instantly elevate visibility The growing role of Reddit, social platforms, and communities in AI discovery How to structure content for AI without sacrificing real users What businesses should stop obsessing over—and what actually moves the needle Whether you run content-heavy sites, ecommerce brands, SaaS, or are evaluating businesses to buy, this episode offers a practical framework for adapting to AI without panic—or guesswork. AI is coming either way.The question is whether your brand will be visible when it does.

Getting finance to buy an online business is no longer just about ticking boxes or relying on outdated bank formulas. Today, lenders are looking forward. They want to understand your assumptions, your go-to-market strategy, and how the business performs once capital is deployed. In this special episode, Jaryd Krause speaks with Ciaran Burke, COO and co-founder of Swoop, a global SME funding marketplace helping buyers access debt, equity, and grant funding across the UK, Australia, the US, and Canada. Ciaran has helped thousands of businesses secure funding by unlocking options traditional banks often miss. You’ll learn how buyers are funding ecommerce, SaaS, and media acquisitions, what lenders really care about beyond the numbers, and why acquisition finance is now easier to access in markets like Australia and the UK. If you are planning to buy an online business and want to understand how deals are being funded right now, hit the “Play” button! BONUS: Explore Swoop’s free funding platform and see if your next acquisition qualifies. Episode Highlights 06:00 Funding Options for Acquiring Online Businesses 09:02 Understanding Deposit Requirements for Acquisitions 12:05 Setting Up a Business Entity for Acquisition Financing 15:03 Navigating Interest Rates and Loan Terms 18:02 Refinancing and Its Importance for Business Owners 21:02 Key Requirements for Loan Approval 24:38 Navigating the Financing Landscape 30:00 Preparing for Acquisition: Key Documentation 36:03 Understanding the Acquisition Process 40:01 Exploring Financing Options and Strategies 43:53 The Importance of Credit and Sector Awareness Key Takeaways ➥ The Australian market was targeted for expansion during COVID due to its strong SME financing landscape. ➥ Deposits for acquisitions can vary significantly based on the business type and trading history. ➥ New investors may need to provide a higher deposit compared to those with established businesses. ➥ A solid business plan and financial model are crucial for securing financing. ➥ Interest rates and loan terms can vary widely based on market conditions and business performance. ➥ Refinancing options can improve cash flow and reduce interest rates over time. Understanding personal credit scores is essential for first-time investors. About Ciaran Burke Ciarán Burke is the COO & Co-Founder of Swoop, a global SME funding marketplace that helps businesses discover debt, equity, and grant options using integrated business data.He co-founded Swoop after a career at KPMG and building the creative network Hiive, and now leads the product & operations work that matches businesses with suitable finance solutions across multiple territories. Swoop’s platform has helped hundreds of thousands of businesses access funding and simplify options that traditional banks often miss, making it a powerful route for buyers who need acquisition capital. Ciarán frequently speaks about debt, equity, and grants to fund acquisitions in the UK, Australia, and the US. Join Swoop Funding for free; ➥ https://swoopfunding.com/au/buying_online_businesses Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ Buy & Sell Online Businesses Here (Top Website Brokers We Use)

In this solo episode, Jaryd Krause dives into a topic that quietly shapes success more than most people realize: relationships. While many know him for his business insights, fewer are aware of how deeply spiritual his personal development journey has been and how much those “non-traditional” practices have contributed to his financial and professional success. With nearly three decades of inner work and growth behind him, Jaryd shares what he typically teaches behind closed doors to paid clients. Lately, one theme has been impossible to ignore: the profound impact relationships have on wealth, confidence, and expansion. He explores how most people have three to five close relationships: family, partners, friends, or colleagues that unintentionally stifle their growth. Check out the full episode to uncover the relationship dynamics that may be quietly holding you back—and learn how to break free from them. Episode Highlights 02:44 The Impact of Relationships on Wealth 05:41 Family Dynamics and Financial Mindsets 07:54 Navigating Friendships and Financial Advice 10:44 The Role of Intimate Relationships in Personal Growth 21:34 The Impact of Relationships on Personal Growth 26:46 Navigating Friendships and Family Dynamics 32:20 Auditing Relationships for Abundance 37:29 Re-engineering Identity Through Social Circles 42:21 Actionable Steps for Relationship Management Key Takeaways ➥ Spiritual practices contribute significantly to business success. ➥ Relationships can unconsciously stifle personal growth and abundance. ➥ Family conditioning often instills a scarcity mindset. ➥ It's crucial to audit your relationships regularly. ➥ Intimate partners can influence your ambition and success. ➥ Friendships should be evaluated based on their alignment with your goals. Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ Buy & Sell Online Businesses Here (Top Website Brokers We Use)

What does it really take to acquire 26 SaaS businesses—and keep them growing? In this episode, Jaryd Krause sits down with SaaS M&A professional Guillaume Lussato for a behind-the-scenes look at how successful software acquisitions actually happen. Guillaume breaks down his unconventional path from software sales at a cybersecurity company to sourcing and closing deals at Constellation Software, one of the most disciplined acquirers in the SaaS world. Guillaume reveals why the best SaaS acquisitions aren’t rushed deals but relationships built over years. He shares how patience, credibility, and consistent founder outreach led to his first acquisition at SaaS Group—a low-profile digital calendar tool called DacBoard—and why targeting under-the-radar SaaS companies can unlock outsized opportunities. The conversation dives deep into today’s hyper-competitive M&A environment, including how to stand out when every founder is being pitched. Guillaume unpacks the red flags most buyers miss, from risky customer concentration to weak net dollar retention, and explains SaaS Group’s clear acquisition framework—capital-efficient, product-led growth businesses with strong fundamentals. The episode wraps with a powerful discussion on how to balance organic growth with acquisitions, avoid overextension, and make smarter strategic decisions when scaling a portfolio of software companies. If you’re serious about SaaS acquisitions, this episode is a must-watch. Click through and watch the full video to learn exactly how Guillaume evaluates, sources, and scales SaaS businesses. Episode Highlights 02:52 Transition from Sales to M&A Origination 05:52 The Art of Deal Sourcing 09:04 Evaluating Founders and Their Businesses 11:47 Understanding Acquisition Criteria 15:10 Growth Strategies: M&A vs. Organic Growth 18:00 Identifying Red Flags in Due Diligence 21:06 Navigating Operational Complexity 23:57 AI Risks and Opportunities in Software 27:06 Balancing Capital Allocation and Diversification Key Takeaways ➥ You need to build relationships, build trust, build credibility. ➥ It can take a really long time to acquire a business. ➥ We try to identify red flags as early as possible. ➥ We don't manage our portfolio through spreadsheets; we're not finance people. ➥ Should we buy it? Why? For how much? About Guillaume Lussato Guillaume Lussato is a senior business development and M&A professional at saas.group, where he helps identify, acquire and scale profitable B2B SaaS companies. He hosts discussions on SaaS M&A, growth, and founder transitions and frequently speaks at industry events about how to grow without VC and what makes SaaS acquisitions succeed or fail. Guillaume focuses on sourcing deals, operational playbooks for scaling post-acquisition, and practical insights that matter to anyone buying online businesses to replace income, scale a portfolio, or prepare for exits. Connect with Guillaume Lussato ➥ https://www.linkedin.com/in/guillaumelussato/ Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ Buy & Sell Online Businesses Here (Top Website Brokers We Use)

What happens when a seasoned real estate investor steps away from physical property and into the world of digital acquisitions? In this episode, we sit down with Julien Jacques, who made the bold transition from building a real estate portfolio to acquiring online businesses—uncovering both the opportunities and the unexpected mistakes along the way. Julien shares his transparent journey, including his non-traditional Canadian financing strategies, the specific digital business models he targets, and the hard-earned “humble realist” lessons that came from both successful acquisitions and costly missteps. Whether you’re managing rental properties, exploring your first acquisition, or curious about “online real estate,” this conversation delivers a grounded, experience-driven look at what it truly takes to scale in the digital business landscape. Ready to rethink how you build wealth beyond physical assets? Watch the full episode now! Episode Highlights 10:51 Lessons Learned in Acquisition 13:28 The Importance of Relationships in Business 16:16 Structuring the Deal 21:01 Navigating Business Financing and Debt 22:11 The Dangers of Overdue Diligence 25:25 Making Decisions with Incomplete Information 29:45 Lessons from a Business Acquisition Failure 36:12 The Importance of Leadership and Networking 40:41 The Journey of an Entrepreneur: Risks and Rewards Key Takeaways ➥ Real estate can provide passive income but requires management. ➥ Buying an existing business can be less risky than starting from scratch. ➥ Due diligence is important but can be misleading if overanalyzed. ➥ Networking is crucial for entrepreneurial success. ➥ Entrepreneurship requires resilience and adaptability. About Julien Jacques Julien Jacques is a former real-estate investor and entrepreneur who pivoted into buying online businesses after a year-and-a-half of searching across franchises, retail, and other opportunities. He now owns Rocket Powered Sound, a digital products e-commerce business selling sample packs to music producers, and has firsthand experience in financing, acquiring, and scaling an online company in Canada. Julien’s practical transition from physical assets to “online real estate” gives him a unique perspective on acquisition due diligence, margin dynamics in digital products, and how to turn acquisition opportunities into reliable income streams. Connect with Julien Jacques ➥ https://www.linkedin.com/in/juljacques/ Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ Buy & Sell Online Businesses Here (Top Website Brokers We Use)

What really kills business deals—without anyone noticing? Not the obvious red flags.Not the spreadsheets.But the quiet mistakes buyers make the moment they think they’ve already won. In this episode, Jaryd Krause sits down with John Martinka (aka The Escape Artist), who’s spent 25+ years advising buyers and sellers across 150+ real acquisitions. No theory. Just what actually happens in deals. You’ll hear why first-time buyers fall in love too fast, how stopping your search early weakens your position, and why relationships matter more than price once negotiations get serious. John also reveals how “great on paper” deals quietly turn into long-term stress, and what to do instead. Plus, what happens after the deal closes: how one small shift helped a buyer grow a business by 75% in under a year, and why growth often fixes problems faster than perfection ever will. If you’re buying a business (or even thinking about it), this episode will change how you see deals before it’s too late.

Most people don’t fail at buying a business because they’re not smart enough.They fail because—without realizing it—they’re setting themselves up to lose before they even begin. In this solo episode of the BOB podcast, Jaryd Krause goes off-script and gets brutally honest about the real reasons people struggle to acquire online businesses, and why these same patterns show up in money, business, and life. This isn’t a tactical “how-to” episode.It’s a mindset reset. Jaryd breaks down the five biggest reasons people fail at buying a business, drawing from his own journey, his work with buyers around the world, and the patterns he sees repeatedly derail otherwise capable people. You’ll learn: Why you don’t need to know how to run or buy a business before acquiring one How “good” advice becomes dangerous when you treat general guidance as personal truth Why most people are mentally unprepared for the acquisition process—even when they have the money How impatience and unrealistic timelines quietly sabotage deals The uncomfortable truth about why wanting a business isn’t enough—and when change only happens out of necessity Jaryd also dives into cultural differences, ambition, pain as a driver of success, and why some people push through every obstacle while others stall indefinitely. This episode is raw, reflective, and unapologetically real.

How far can $100,000 really take you in business acquisitions? One deal?A small portfolio?Or a scalable acquisition machine? In this episode, Jaryd Krause sits down with SBA Business Development Officer Glenn Giro to break down the real math behind buying businesses with SBA financing, and why there’s technically no cap on how many businesses you can acquire, as long as you understand the rules that actually stop most buyers. They unpack how entrepreneurs are using up to 90% SBA financing, long 10-year terms, and no prepayment penalties to build portfolios most people assume are out of reach. You’ll discover: How $100,000 in cash can unlock a $1M+ acquisition The $5M SBA cap per NAICS code and how it impacts serial buyers Why banks love SBA loans (and why that matters to you) The real fees lenders don’t explain upfront How cash flow and debt service coverage are actually calculated What changes when you go from your first deal to your second, third, or fifth When 100% financing is possible and when it’s not Why do some high-multiple digital businesses get rejected The timeline lenders expect before approving your next acquisition If you’re serious about buying your first digital business or turning one deal into a portfolio of cash-flowing assets, this episode will completely reframe how you think about capital, leverage, and scale. Watch the full video to see the numbers, strategies, and acquisition pathways most buyers never learn about. Episode Highlights 02:55 – Why a “simple” 10% down payment can still kill your SBA deal if you don’t understand total project costs. 05:08 – The harsh truth: why $100K is often not enough to safely buy a $1M business. 10:52 – How SBA’s 75% loan guarantee unlocks 90% financing—and why banks are eager to lend. 12:57 – The hidden cost most buyers miss: $20K–$30K in SBA fees on a $1M acquisition. 15:16 – The real reason most buyers can’t buy a second business right after their first. 23:59 – The quiet rule that caps portfolios at $5M per NAICS code—and how it blocks long-term scaling. Key Takeaways ➥ SBA financing allows buyers to acquire businesses with as little as 10% down, but cash reserves and liquidity matter more than purchase price alone. ➥ The SBA’s 75% government guarantee reduces bank risk and unlocks long-term, high-leverage financing for profitable online businesses. ➥ Seller financing can help bridge equity gaps, but new rules requiring 10-year standby make it rare in competitive acquisitions. ➥ Most buyers need 6–12 months of successful operations before qualifying for a second SBA-backed acquisition—proof of execution accelerates approvals. ➥ Each business must support its own debt service; strong cash flow in one acquisition won’t compensate for a weak second deal. ➥ NAICS code limits quietly shape acquisition strategy—buyers who plan ahead can scale portfolios faster and avoid unexpected financing caps. About Glenn Giro Glenn Giro is a seasoned SBA business development officer and acquisition financing expert who helps entrepreneurs buy and grow businesses using strategic SBA-backed loans. He hosts “SBA University,” a training series for business owners and aspiring acquirers, and regularly speaks about acquisition financing and business ownership strategies. Connect with Glenn Giro ➥ https://www.linkedin.com/in/glenn-giro/➥ https://www.youtube.com/@SBAUniversity Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ Buy & Sell Online Businesses Here (Top Website Brokers We Use)

In this episode of the BOB Podcast, Jaryd Krause chats with David C. Barnett—author, educator, and all-around small-business acquisition pro. David’s spent 11 years making straightforward videos about buying, selling, and running small businesses, and he’s seen it all. They dive into what most first-time buyers totally miss—like how a “simple” service business pulling in $300–400k a year can still hit you with $10k in unexpected repairs, or how a business that seems hands-off can take up way more mental energy than you expect. You’ll hear things like:

He’s bought over 15 digital businesses—and learned some lessons the hard way. In this episode of the BOB Podcast, Jaryd Krause sits down with Yury Byalik, a seasoned growth marketer, acquisitions strategist, and digital-business investor who has spent over 15 years building, buying, and scaling profitable online companies. Currently serving as Head of Strategy & Acquisitions at Onfolio Holdings, Yury has mastered the art of spotting opportunities, structuring deals, and growing digital businesses into high-performing assets. But here’s the thing: acquisitions aren’t as simple as signing papers. Mistakes happen—and they can cost you time, money, and growth. Yury shares exactly what to avoid and what strategies actually work. In this episode, you’ll learn:

In this episode of the BOB Podcast, Jaryd Krause sits down with Nick Bradley, a world-renowned author, speaker, and business growth expert known for helping entrepreneurs, business leaders, and investors build, scale, and sell high-value companies. Nick brings more than a decade of Private Equity experience to the conversation. Throughout his career, he has completed over 50 acquisitions, sold 26 businesses, created over $5 billion in value, and played key roles in three exits exceeding $1 billion each. His expertise offers a rare, behind-the-scenes look at what it truly takes to buy, integrate, grow, and exit companies at scale. In this episode, listeners will learn:

Think a million-dollar online business is out of reach? The real barrier isn’t the price—it’s everything you don’t see coming before you even sign. In this solo episode, Jaryd Krause pulls back the curtain on the part of buying a 7-figure business that almost nobody talks about—the real costs, the real timelines, the real competition, and the parts of the process that can quietly wreck your deal long before you ever get to the closing table. Most people assume a $1M acquisition is simple math:Find the business, put down the deposit, sign some papers, done. But behind every one of those deals are fees, structures, advisors, lenders, deadlines, and expectations that—if you’re not prepared—will eat your budget and your sanity alive. Here’s what Jaryd gets into:

What if the one thing stopping you from owning a thriving online business isn’t money… but what you don’t know about SBA financing? In this episode, Jaryd Krause chats with Ray Drew—aka SBA Ray—host of The Art of SBA Lending, the #1 podcast that pulls back the curtain on how SBA loans really work. Ray is the Managing Director at Truliant Federal Credit Union, a deal closer with hundreds of successful SBA-financed businesses under his belt, the man behind millions in SBA-backed deals, and the architect of SBA success stories nationwide. He’s seen everything—the smooth wins, the total nightmares, and the deals that fell apart days before closing. Most people think an SBA loan is simple: apply, get approved, buy the business, boom—you’re a CEO. But the truth? There are traps hidden in plain sight. And missing just one could cost you the deal—or tens of thousands in wasted time and fees. Here’s what Ray and Jaryd dive into:

Most people guess marketing tricks—but Andri Sadlik knows the shortcuts, the pitfalls, and the moves nobody talks about. In this episode, Jaryd Krause sits down with Andri Sadlik, a pro at scaling SaaS, AI, and e-commerce businesses. Andri launched his first business and exited successfully. After that, he scaled multiple Amazon FBA brands from $100K a year up to $1M, and finally over $10M. No gimmicks, no luck—just carefully built systems, a strategy that makes sense, and teams that execute like clockwork. He’s also the co-founder of ProductPinion, a SaaS company he’s planning to exit, and has been featured in top media outlets for his expertise in scaling businesses. In this conversation, you’ll hear how he:

What if you could turn a $5K/month business into $80K/month in under a year? That’s exactly what Chan Yuenenyi did. In this episode, Jaryd Krause chats with the founder and CEO of EssayGrader AI—the world’s leading AI grading platform trusted by over 100,000 educators. When Chan bought the business, it was generating only $5,000 per month. Fast-forward less than a year later, and he’d scaled it to $80,000/month, hitting $1M in annual recurring revenue. But here’s the twist: Chan didn’t chase shiny tactics or massive ad budgets.He used precision. Systems. Deep understanding of what users actually need. Before founding EssayGrader AI, Chan managed a billion-dollar product line at OpenText. So, he knew one thing most first-time buyers miss—buying a business is easy. Growing one takes vision. In this conversation, you’ll discover how he:

It’s not the numbers that make a business thrive—it’s the people, the trust, and the purpose behind it. In this revealing episode, Jaryd Krause sits down with Antoine Minoux, Principal Product Designer at Yelp and a serial entrepreneur who has founded, grown, and sold multiple successful SaaS ventures, including Improvmx and VoilaNorbert. Together, they unpack what really happens behind the scenes of buying, scaling, and selling online businesses—and the emotional intelligence required to do it right. Antoine shares his candid reflections on navigating acquisitions, from spotting undervalued opportunities to balancing multiple ventures and knowing when it’s time to sell. They explore how trust and transparency form the foundation of any successful deal, why valuation isn’t just about numbers, and how emotional awareness can be the difference between a smooth exit and a painful one. Through Antoine’s firsthand experiences, this conversation provides a roadmap for entrepreneurs looking to grow not just through innovation but through strategic acquisition and authentic relationships. Together, they explore: ✔️ Why buying an existing business can be less risky than starting from scratch✔️ The emotional and relational side of business acquisitions most founders overlook✔️ How to balance multiple ventures without losing clarity or momentum✔️ The right way to approach valuation and negotiation in SaaS deals✔️ Lessons learned from multiple exits—and why selling doesn’t always mean letting go Whether you’re an aspiring acquirer, a seasoned founder, or somewhere in between, this episode will challenge how you think about growth, exits, and the role of trust in entrepreneurship.

Business success isn’t just about buying the right company—it’s about building the right foundation. In this insight-packed episode, Jaryd Krause sits down with Brian and John, two entrepreneurs who’ve mastered the art of acquiring and scaling online businesses through mentorship, strategic planning, and sustainable growth. From their first steps into e-commerce to managing complex acquisitions, Brian and John share how having the right mentor, team, and financial structure can make or break a deal. They pull back the curtain on what it really takes to grow an online business—revealing how patience, education, and teamwork pave the way for long-term success in a fast-changing digital economy. Together, they unpack: ✔️ The role of mentorship in accelerating business growth and confidence✔️ How to build diverse revenue streams that stabilize your portfolio✔️ Financial planning fundamentals every buyer needs before acquisition✔️ Why a strong team and legal support system are non-negotiable✔️ The mindset shift from “buying a job” to “owning a business”✔️ How customer feedback fuels innovation and operational improvement✔️ Building systems that scale—and keep your business sustainable Through candid reflections and hard-won lessons, Brian and John offer a blueprint for entrepreneurs who want to expand strategically while avoiding the burnout and chaos that often follow growth. Whether you’re an aspiring buyer or already running multiple online ventures, this episode will equip you with the mindset and structure to scale with confidence.

Buying a business is one thing—but knowing how to actually grow it is where the real challenge (and opportunity) begins. In this episode, Jaryd Krause chats with Matthew Person, a corporate strategist, investor, and M&A expert who’s mastered the art of scaling through acquisition. With experience across investment banking, corporate development, and private equity, Matthew knows what it takes to turn good businesses into great ones. He’s the mind behind the Square Management System, a framework built to help entrepreneurs align culture, structure, and strategy so growth happens seamlessly—not chaotically. In this episode, you’ll learn: ✔️ Why understanding customer lifetime value is more important than acquisition cost✔️ How pricing and packaging decisions influence business scalability✔️ What makes the Square Management System a powerful tool for growth✔️ The critical role of cultural fit in M&A integration✔️ How to manage different revenue types and their impact on valuation✔️ Why boring businesses often yield the best returns✔️ The common integration challenges—and how to plan for them✔️ What successful portfolio builders do differently from the rest Jaryd and Matthew break down the real drivers of business success, from understanding customer lifetime value and pricing strategy to building systems that make integration smooth and scalable. Whether you’re eyeing your first acquisition or managing a growing portfolio, this episode shows you how to scale smarter, not harder.

Success in business isn’t just about strategy—it’s about mindset. In this performance-driven episode, Jaryd Krause sits down with Itamar Marani, one of the world’s leading high-performance mindset coaches, to unpack why so many entrepreneurs unknowingly sabotage their own success when buying, growing, or scaling online businesses. A former Israeli Special Forces operative, the youngest federal agent and air marshal in Israel’s history, and a Brazilian Jiu-Jitsu black belt, Itamar has coached hundreds of six to nine-figure entrepreneurs, executives, and elite athletes to break through mental barriers, eliminate self-sabotage, and operate at their peak under pressure. His clients have exited companies for nine figures, raised hundreds of millions in capital, and ranked among the top performers in their industries. Together, Jaryd and Itamar dive deep into the psychology of performance, exploring: ✔️ The three biggest bottlenecks holding entrepreneurs back from success✔️ How to identify the most direct path to your goals—and stay on it✔️ The top three performance traps that stop business owners from scaling✔️ Why even experienced buyers struggle after acquisition—and how to fix it Through real-world examples from Itamar’s military and coaching experience, you’ll discover how to spot the patterns of self-sabotage that quietly derail deals, limit growth, and block financial freedom. Whether you’re preparing to buy your first online business, scale an existing one, or build a portfolio, this episode reveals the mindset frameworks that separate high performers from those stuck in perpetual struggle.

Scaling an e-commerce business from six to seven figures is an exciting milestone—but it’s also where many founders hit costly roadblocks. In this insightful episode, Jaryd Krause sits down with award-winning e-commerce mentor Jodie Minto, founder of the seven-figure fashion brand iland co., host of the Online Store Success podcast, and certified digital marketer, Meta Ads specialist, and life coach. Jodie built her global fashion label from scratch while raising a young family, working full-time, and living in the Middle East—before scaling it to seven figures with customers and stockists around the world. Together, they dive deep into what it really takes to grow an e-commerce business beyond six figures, avoid the biggest pitfalls along the way, and prepare for a successful exit. Jodie shares her unfiltered journey of scaling and then strategically de-scaling her brand, the lessons from her first failed exit attempt on Flippa, and how she ultimately secured an all-cash sale to an outside buyer. You’ll learn: ✔️ The two biggest mistakes brands make when trying to jump from six to seven figures✔️ Why scaling too fast can backfire—and how to know when to pull back✔️ The mindset traps that lead to burnout and how to avoid them✔️ What to expect when selling your business (and how to recover if a deal falls through)✔️ How to align business growth with life goals for long-term fulfillment Whether you’re scaling toward seven figures, planning for an exit, or simply want a healthier approach to growth, this episode is packed with practical insights from someone who’s been through it all.

Get ready to discover a whole new way for people to find your business online at the forefront of the AI revolution in this insight-packed episode. Joining the conversation is Dom Wells, Founder & CEO of Onfolio Holdings (NASDAQ: ONFO), a public holding company for profitable online businesses. After acquiring an SEO agency, Dom turned it into a smart new service called Generative Engine Optimization (GEO) — helping businesses show up inside answers, tips, and conversations from tools like ChatGPT, Bing Copilot, and Claude. GEO is changing how brands get noticed in 2025 and beyond. Instead of just showing links, AI tools give people clear answers. GEO makes sure your business is part of those answers, so you’re seen where customers are already looking. In this episode, you’ll find out: How GEO is different from old-school SEO. Why AI search feels more helpful and personal than regular search engines. Simple ways to check and boost your visibility in tools like ChatGPT and Bing Copilot. Real stories of businesses getting fast results with GEO — plus how to grab free audits and tips shared during the show.

This episode is an eye-opening case study where Jaryd Krause sits down with AJ, a Buying Online Businesses graduate who made the leap from running a large IT team at a global bank to building an online business portfolio. AJ shares how he went from launching a failing startup to successfully acquiring a $50,000 media and membership business that now generates $2,000 net profit per month—all within just six months. Inside this conversation, you’ll know: ✔️ Why AJ abandoned the startup path in favor of buying an existing business✔️ The exact business model he chose—and why it stood out among the rest✔️ How he saved money on the acquisition price (including what multiple he actually paid)✔️ The due diligence steps he took to minimize risk before signing the deal✔️ The hardest part of buying a business (his answer may surprise you)✔️ His best advice for first-time buyers—and what’s next as he builds his portfolio Packed with lessons from someone who’s navigated the challenges and emerged profitable, this episode is a must-listen whether you’re planning your first business acquisition or aiming to master your due diligence process

In this power-packed episode, Jaryd Krause sits down with serial founder and dealmaker Anthony Franco, a man who knows exits inside and out. Having built and sold seven companies—six of them successfully, including two to publicly listed firms—Anthony brings rare, battle-tested wisdom to the table. Together, they dig into what it really takes to engineer a successful exit in the $5M–$50M range. From preparing your business to maximize valuation, to structuring deals that minimize risk for both buyers and sellers, Anthony shares the strategies he’s used to navigate countless transactions. He doesn’t sugarcoat it either—every deal has “hair” on it, and this conversation unpacks exactly how to handle those messy, unexpected challenges that can tank a deal if you’re not prepared. You’ll learn:✔️ How to structure an exit so you walk away with more security and better terms✔️ Why taking your foot off the gas before closing can destroy your valuation✔️ How buyers can avoid catastrophic mistakes by spotting risk early✔️ What makes a business truly attractive to both strategic and financial buyers✔️ The evolving role of AI in business growth, exits, and even the future of work Whether you’re eyeing a future sale, planning to acquire, or just want to build a business that’s more valuable and resilient, this episode is a masterclass in deal-making straight from someone who’s been through it all.

In this raw and eye-opening episode, Jaryd Krause chats with Matthew Tse—a former Big Tech software engineer who ditched the corporate grind to buy his way into freedom through online business. Today, he runs ImprovMX.com, a SaaS business he acquired after sifting through countless deals, failed startup attempts, and plenty of trial and error. Matthew doesn’t sugarcoat it. He shares the highs, the mistakes, and the exact process that helped him land the right acquisition to replace his income and build a life on his own terms. In this no-BS conversation, you’ll discover: ✔️ How many businesses do you really need to analyze before finding “the one”✔️ The critical mindset shifts that help you push through failed deals and land a winner✔️ Why chasing small, cheap businesses can actually cost you more in the long run✔️ The price range Matthew now recommends for friends looking to buy online✔️ His top growth levers for scaling SaaS—starting with retention before expansion If you’ve ever wondered how long it actually takes to buy an online business—or what it feels like to transition from employee to owner—this episode pulls back the curtain on the entire journey.

In this sharp and savvy episode, host Jaryd Krause welcomes M&A heavyweight Michael Vann—President of the Vann Group and Principal at Eaton Square—for a deep dive into the brilliant… and brutally expensive mistakes entrepreneurs make when trying to grow through acquisition. With 25+ years of deal-making, scaling, and succession planning, Michael’s been in the trenches guiding businesses to multi-million dollar exits across industries from manufacturing to online empires. He’s seen it all—and he’s here to share what not to do when chasing growth. Spoiler: Buying three businesses in six months with zero integration strategy? That’s not scaling. That’s self-sabotage. In this no-fluff convo, you’ll learn: ✔️ The explosive difference between a strategic buyer and a chaotic cowboy ✔️ Why some acquisitions implode and drain value instead of adding it ✔️ How to prep your current business to absorb acquisitions without blowing it up ✔️ The secret to thinking beyond the buy—to integration and exit strategy ✔️ How to build a business so irresistible that even your competitors want to buy it If you’ve ever thought, “Maybe I’ll just buy another business and double my revenue,” you need to hear this.

Exiting a business can be one of the most rewarding moments of an entrepreneur’s journey—or one of the most costly mistakes if handled poorly. Many sellers unknowingly leave hundreds of thousands, even millions of dollars, on the table simply because they aren’t prepared for the exit process. Jaryd Krause speaks with Domenic Rinaldi, a seasoned M&A advisor and owner of Sun Acquisitions, who has successfully guided over 500 business transactions. As the founder of K2 Advisor, Domenic specializes in helping business owners understand exactly what it takes to execute a profitable and stress-free exit. Together, they break down the biggest mistakes sellers make when exiting their businesses and how to avoid them. You’ll discover: ✔️ How owner involvement and single-source dependencies can destroy your business valuation ✔️ Why many sellers are blindsided by market shifts, tariffs, and environmental changes ✔️ The critical role of value drivers and how to identify them before going to market ✔️ What can go catastrophically wrong during a deal—and how the right advisory team can prevent it ✔️ Why you should always be “exit ready,” even if selling isn’t on your immediate horizon If you’re preparing to sell your business—or simply want to protect the value you’ve built—this episode is packed with actionable insights to help you exit on top.

Running a business is about building something that works without you, not just putting in the hours. But far too many entrepreneurs stay stuck in the weeds, overwhelmed by daily tasks and unclear on how to truly scale. That’s where systems—and now, AI—change everything. In this conversation, Jaryd Krause is joined by David Jenyns, founder of Systemology and author of SYSTEMology and The Systems Champion, to unpack how smart systems combined with the power of AI are transforming the way online businesses grow. David has built and sold multiple companies, helped hundreds of business owners systemize their operations, and now leads the conversation on how AI can be used not just to support teams, but to replace certain roles altogether. You’ll learn: ✔️ How to use AI to build and improve systems in your business✔️ Why experienced talent plus AI is replacing the traditional VA model✔️ How to step back from your business without losing momentum✔️ Real-life examples of AI replacing inefficiencies and boosting profits When it comes to growing your business, reclaiming your time, and creating something that endures, this episode is packed with useful strategies and steps to follow.

Understanding the fine print that could make or break your deal is just as important when purchasing a business with SBA financing as it is when obtaining a loan. All too frequently, buyers lose out on opportunities or become mired in transactions that don't fit the program because they are unaware of the nuances of SBA regulations. The CEO of SBA Loan Group, Yankie Markowitz, sits down with Jaryd Krause in this episode to discuss his extensive knowledge of SBA loans and how he has facilitated more than $1 billion in SBA and real estate transactions. Yankie explains which business categories are eligible for SBA financing, what has changed recently, and how to handle the complex world of debt ratios, deal structures, and cash requirements. You’ll learn: ✔️ Which businesses can—and can’t—be acquired with SBA loans ✔️ How much cash do you need to qualify ✔️ Why e-commerce fits well with SBA financing, and where it falls short ✔️ The ins and outs of seller notes, holdbacks, and loan terms ✔️ Real-world lessons from deals that worked—and ones that didn’t This episode provides useful, straightforward advice from one of the most seasoned SBA specialists in the industry, regardless of whether you're prepared to purchase your first company or want to improve your acquisition approach.

Buying or selling a business isn’t just a transaction — it’s a turning point. But too often, what buyers think they want and what sellers believe they deserve don’t line up with reality. The result? Stalled deals, missed opportunities, and plenty of frustration on both sides. In this episode, Jaryd Krause sits down with Matt Frisca, owner of Transworld Business Advisors of La Grange and Tinley Park, to unpack the biggest reasons deals fail—and what it really takes to make them work. With 20+ business sales closed annually and 50+ active listings, Matt shares real-world insights from both sides of the table. You’ll learn: ✔️ Why sellers struggle to exit cleanly✔️ Common mistakes buyers make (and how to avoid them)✔️ The truth about SBA financing and “no money down” deals✔️ What due diligence really looks like in today’s market Whether you're buying, selling, or just curious, this episode delivers raw advice and actionable strategies from a dealmaker who knows the game.

Let’s be real — buying or selling a business is one of the biggest decisions you’ll ever make. Get it right, and it could be life-changing. Get it wrong… and the fallout could be brutal. That’s exactly why this week’s episode is a must-listen. Jaryd Krause sits down with Katarina Strandberg, a powerhouse Swedish business lawyer with deep expertise in venture capital, scale-ups, and M&A. She’s worked with founders, investors, and SME leaders across Europe, and brings not only legal chops but also perspective as an angel investor, published author, and university lecturer. Katarina has seen it all — and she’s here to share the real stories, the hard truths, and the clever strategies that can make or break your deal. In this episode, you’ll learn: ✔️ The biggest risks buyers face (and how to avoid stepping on legal landmines)✔️ What really happens during legal due diligence — and why it’s more than just paperwork✔️ How to deal with “deal fatigue” and who should keep cool when emotions run high✔️ Jaw-dropping stories of deals gone wrong — and the legal moves that could’ve saved them✔️ Clever deal structures and funding options that most people never think about✔️ How to avoid surprise legal bills (yes, it’s possible!)✔️ Why skipping legal help might be the most expensive mistake you ever make If you’ve ever felt overwhelmed by contracts, confused by due diligence, or just unsure about when to bring a lawyer in, this episode is your roadmap.

Strap in for a brutally honest conversation as Jaryd Krause sits down with none other than Elliot Holland, a Harvard Business School alum, seasoned entrepreneur, and strategic founder. Elliot runs a seven-figure due diligence firm that performs "mini audits" on businesses, helping investors avoid being misled by clever sellers and slick brokers. With nearly 20 years of experience in small business acquisitions, Elliot has seen it all—and then some. From hidden red flags in financials to smoke-and-mirrors marketing metrics on Amazon and SEO-driven sites, he shares exactly where buyers get it wrong—and how those mistakes can cost you hundreds of thousands, or worse, your entire investment. This episode will pull back the curtain on how unsuspecting buyers get swindled into buying dud deals, all because they skipped real due diligence. Highlight the critical considerations buyers often miss in the acquisition process: ✔️ The most common (and costly) mistakes buyers make in due diligence✔️ Why relationships with sellers matter—and how they can go sideways fast✔️ How sellers can mislead or manipulate the narrative to close a deal✔️ Financial vs. marketing due diligence—what most acquirers overlook✔️ The frameworks Elliot uses to assess businesses like an expert This is not just theory—Elliot has personally helped countless clients dodge bad deals and secure multi-million-dollar wins, all by demystifying the due diligence process. With his signature humor, straight talk, and lived experience, he makes complex business buying principles not only clear but actionable. Whether you're a first-time acquirer or scaling your portfolio, this episode will save you more than money—it could save your sanity. Don’t even think about buying a business until you listen to this conversation. Episode Highlights 04:15 – Red flags usually show as many small issues rather than one big problem 10:30 – Verifying seller’s time commitment by reviewing task lists and holding strategy meetings 18:45 – Wanting shortcuts in due diligence can lead to costly mistakes 23:00 – Sellers often resist reasonable buyer requests like strong non-competes and management interviews 26:10 – Negotiation is a strategic dance where sellers test buyer strength 29:15 – Cheaper advisors often bring higher risks and lower value on seven-figure deals Key Takeaways ➥ Red flags are subtle and require a sharp, skeptical mindset to detect ➥ Sellers use stories and distractions instead of admitting flaws outright ➥ Due diligence takes time and can be uncomfortable but shortcuts are costly ➥ Experienced advisors are critical for high-value deals to avoid disaster ➥ Buyers need to be ready to walk away if sellers are not transparent or cooperative ➥ Emotional detachment helps buyers make better decisions and negotiate smarter About Elliot Holland Elliott Holland is a Harvard Business School alum, former business acquirer & OG in small business acquisitions. He runs TheBusinessBuyingMasterclass.com and a 7-figure business that does "mini audits" on businesses before clients acquire them to be sure they're not swindled. With nearly two decades of experience, Elliott empowers everyday investors to acquire million-dollar businesses because he's been in their shoes and offers insight others cannot. Elliott simplifies complex small business buying concepts with humor so that everyday investors can understand. With over 100 podcast appearances and speaking engagements at top business schools, Elliott shares expertise on entrepreneurship, investing, and business buying. Connect with Elliot Holland ➥ https://www.linkedin.com/in/elliottholland/ Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH

In this compelling episode, Jaryd Krause is joined by seasoned dealmaker and legal expert Jerome Fogel, partner at Fogel & Potamianos LLP, a boutique law firm specializing in high-stakes mergers, acquisitions, and capital raises. With a client list that spans venture funds, emerging tech companies, and elite athletes, Jerome offers a rare behind-the-scenes look at what it takes to structure smart, safe, and scalable business deals. Unpack the most critical questions aspiring buyers need to ask before acquiring an online business: ✔️ What are the hidden risks in buying or selling?✔️ How can poor team dynamics tank a deal?✔️ Should you use financing to buy a business—and what’s the best way to structure it?✔️ Where are the most promising online businesses being acquired today? Dive deep into the importance of due diligence, the common pitfalls buyers fall into, and how Jerome has helped high-profile clients—both on Wall Street and in the sports world—navigate complex transactions and build generational wealth. Whether you're looking to buy your first online business, scale your portfolio, or just want a masterclass in deal-making from someone who lives and breathes it, this episode delivers powerful insights and practical strategies. Don’t miss this one—it’s packed with value from start to finish. Episode Highlights 04:45 – Current valuations explained, covering how tariffs and supply chain issues impact multiples and buyer decisions. 07:20 – Typical ways buyers finance acquisitions, including credit lines, SBA loans, equity rollovers, and search funds. 10:55 – Major mistake buyers make by rushing post-acquisition integration without building trust within the team. 12:45 – What successful acquisitions have in common by retaining key team members and valuing the founder’s knowledge. 24:10 – Key risk prevention strategies involving thorough reps and warranties, clear earnout terms, strong IP protections, and precise legal language. 26:30 – Why clear definitions around risk and performance clauses are vital. Key Takeaways ➥ M&A valuations currently range from 3–8x EBITDA for traditional companies and 10–15x for platform tech businesses, influenced heavily by tariffs and market uncertainty. ➥ Buyers typically operate in the $2M to $25M+ EBITDA range and rely on strong banking relationships, SBA loans, or creative financing like equity rollovers. ➥ Structuring deal terms clearly—especially reps and warranties and material adverse effect clauses—is critical to managing risk in acquisitions. ➥ Post-acquisition integration is one of the toughest challenges; involving existing teams and respecting founders’ knowledge leads to smoother transitions. ➥ Restrictive covenants are essential to prevent sellers from competing after the sale and protect buyer investments. ➥ Every deal is unique and requires customized, creative solutions; cookie-cutter approaches don’t work in M&A. About Jerome Fogel Jerome Fogel is known as a dealmaker and innovator in the legal community. He is a partner with Fogel & Potamianos LLP and represents successful venture and hedge funds, corporations, and sports superstars.Fogel & Potamianos LLP is a boutique transactional firm that provides sophisticated counsel for buy-and-sell side mergers and acquisitions, fund formation, capital raises, and off-field sports transactions.Jerome has a 360-degree view of dealmaking, as he represents emerging companies raising capital, venture funds deploying capital, advisors and investors, and private companies in mergers and acquisitions.Jerome began his career in real estate finance at GE Capital. He is a graduate of the Haas School of Business (BS) and New York University School of Law (JD). Connect with Jerome Fogel ➥ https://www.linkedin.com/in/jeromefogel/ ➥ www.fpgeneralcounsel.com Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH

What if you could skip the struggle of starting a business from scratch—and step straight into profit? In this solo episode, Jaryd Krause pulls back the curtain on everything you need to know before buying your first (or next) profitable online business. No guest this time—just Jaryd, and over ten years of real-world experience helping thousands of people build financial freedom through smart acquisitions. This episode is a deep dive inspired by Jaryd’s most-watched YouTube content and the questions he hears constantly from aspiring buyers: Why should you buy a profitable business? How much should you invest? Should you use your cash or finance the deal? And where are people buying these businesses today? Get ready for a no-fluff breakdown of: ✔️ Why buying a profitable online business can fast-track your path to income and freedom✔️ How much capital do you need to get started (spoiler: it’s not always as much as you think)✔️ The truth about financing a deal—and what creative structures work✔️ Where to find legitimate, vetted businesses for sale right now✔️ The rookie mistakes that could cost you thousands—and how to avoid them This isn’t financial advice—but it is packed with insights from someone who’s helped people go from browsing listings to building six- and seven-figure digital business portfolios. If you’re ready to move from dreaming to doing, this episode will show you exactly what to consider, what to avoid, and where the real opportunities are in 2025’s online business marketplace. Hit play and take notes—this one’s loaded. Episode Highlights 04:17 – Why buying a profitable online business is better than starting one from scratch? 07:38 – The ideal type of online business to acquire as a beginner. 13:24 – How much money should you invest when buying your first business? 18:43 – Why must you understand the ROI beyond just net profit? 27:46 – Myths around no-money-down deals and what real financing looks like. 31:22 – Where to find online businesses for sale: brokers vs. off-market deals? Key Takeaways ➥ Buying an existing online business is less risky and faster than starting fresh, as you inherit proven systems, traffic, and revenue, reducing trial and error. ➥ “No money down” deals are rare and mostly involve distressed or declining businesses; most require some cash upfront. ➥ Acquisitions usually need a mix of cash, lender, and seller financing, with 10-20% cash upfront to show commitment. ➥ Reliable marketplaces like Empire Flippers, Quiet Light, and Flippa are great starting points for sourcing online businesses. ➥ Sellers often move on not because their business is failing but because of personal reasons like boredom or lifestyle changes, emphasizing the importance of proper due diligence before buying. Connect with Jaryd Krause ➥https://www.linkedin.com/in/jarydkrause ➥ $240K Income When Buying An Online Business - https://www.youtube.com/watch?v=G3yja-KnZzA&t=105s ➥Why Size Matters When Buying An Online Business - https://www.youtube.com/watch?v=7OWdl_n9rZI Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx

Buckle up for an eye-opening episode where Jaryd Krause is joined by powerhouse entrepreneur and investor Justin Williams—a man who’s navigated everything from crippling six-figure debt to building and selling a multimillion-dollar business. Justin’s journey is far from ordinary. After dropping out of college, he and his wife, Tara, left their careers to pursue financial freedom. Their first business left them $120,000 in debt, living in a shared house with a newborn. Instead of quitting, they shifted to real estate, flipping over 100 houses a year and launching House Flipping HQ, a real estate education company that helped thousands succeed. Justin revealed how he sold his real estate education business for over $3.5 million—covering the why, when, and how. They dive into the unconventional yet strategic deal structure when selling to an operator already in the business. Then he delved into wealth building through business and real estate. Justin explains if he’d buy an online business, how he’d finance it, and the math behind buying a $2M business, hiring an operator, and earning $300K net profit annually without running it himself. Gain insights on: ✔️ When is the right time to sell your business?✔️ The differences between investing in real estate vs. digital businesses✔️ How to build sustainable wealth without burning out✔️ And most powerfully—how Justin got through the lowest points of his journey. If you're looking for real talk about business, money, mindset, and freedom, this is the episode for you. Don’t miss this raw, high-energy conversation that’s packed with strategy, real numbers, and heart. Whether you're planning your first acquisition, prepping for a sale, or just needing motivation to keep pushing, this one will hit home. Episode Highlights 03:00 – The journey to selling a $3.5M+ online business and lessons learned 08:20 – Using SBA loans to buy businesses vs. buying without them – pros, cons, and examples 10:50 – Buying businesses you don’t operate: how Justin makes it work and what to look for 17:35 – How Justin handled $120K in debt and overcame early financial struggles 23:40 – Managing expectations: The reality behind case studies and quick success stories 28:20 – Balancing ambition with lifestyle: Prioritizing family, health, and business growth 38:50 – Building habits and mentality for consistent progress versus just grinding Key Takeaways ➥ Everyone’s journey is different—don’t let case studies make you feel behind. ➥ Selling his $3.5M business was a strategic move to gain freedom and shift into a new season of life. ➥ A clean, simple business model and solid financials were critical in structuring a successful sale. ➥ SBA loans can be powerful tools for acquiring businesses, but creative financing is often just as effective. ➥ You don’t always have to operate the businesses you buy—systems, leadership, and delegation are key. ➥ Real estate offers stability while business offers higher returns—knowing when to lean into each is crucial. ➥ Long-term vision and emotional resilience helped Justin overcome $120K in debt and build real wealth. About Justin Williams Justin Williams dropped out of college with a bold vision, convincing his wife, Tara, to leave her teaching job so they could start their first business. But their million-dollar dream quickly turned into a $120,000 debt nightmare. Determined to turn things around, they hustled out of debt and pivoted to real estate, eventually flipping 100 houses a year. Their success led them to launch House Flipping HQ, helping others build thriving real estate businesses. After selling the company, they took time off to focus on investments and new ventures.Now, as the founders of Millionaire University, their mission is simple: help people "graduate rich, NOT broke." With over 600,000 monthly podcast downloads, MU is transforming how entrepreneurs learn, grow businesses, and create wealth. Connect with Justin Williams ➥ https://www.millionaireuniversity.com/ Resource Links ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx

Get ready for a powerhouse episode as Jaryd Krause sits down with Andy Allaway, CEO of Empire Flippers—the leading platform for buying and selling online businesses. Andy brings nearly a decade of experience in the digital acquisition space, having both bought and sold businesses himself before joining Empire Flippers. With a background in scaling lean, remote-first teams and a passion for empowering global leadership, Andy shares his perspective on how the landscape of online business acquisitions has transformed over the years. Get a front-row seat to a conversation that spans from the early days of online business trading to today’s ever-evolving market. Andy and Jaryd explore how multiples have shifted, the role macroeconomic trends play in valuations, and what’s driving buyer and seller behavior in 2025. They unpack lessons from 2020’s acquisition boom, the downturn of 2023, and what savvy investors should prepare for in the years ahead. Deep dive into:✔️ How Empire Flippers has grown and adapted in a changing market✔️ Why multiples are where they are now—and what to expect next✔️ Financing six- and seven-figure deals (and what you need to know)✔️ The critical role of buyer-seller relationships in successful transactions✔️ New tariffs affecting e-commerce deals and how to navigate them✔️ The rise and fall of popular business models✔️ How AI is reshaping the acquisition game—for better and worse Plus, Andy offers actionable insights into which business models are thriving right now and shares real-world examples of where deals succeed or fall apart—and why. Whether you're preparing to buy, gearing up to sell, or simply want to understand how the digital business market is evolving, this conversation is a must-listen. Tune in to learn from one of the top minds in the space and gain clarity on where online business acquisitions are heading. Episode Highlights 04:12 – What key metrics buyers look for when evaluating online businesses 10:05 – The importance of business simplicity and clean financials for buyers 13:20 – Different types of online business models currently in demand 16:45 – Strategies for improving business value before selling 23:50 – Challenges buyers face when scaling newly acquired online businesses 27:15 – The role of due diligence in successful business acquisitions 31:40 – Key trends shaping the future of buying and selling online businesses 35:05 – Advice for entrepreneurs considering acquisition as a growth strategy Key Takeaways ➥ Buyers prioritize clear, consistent financials and simplicity when evaluating online businesses to reduce risk and ensure scalability. ➥ Post-acquisition challenges often include scaling the business efficiently and managing growth without sacrificing quality. ➥ Market trends indicate increasing competition but also more opportunities for entrepreneurs leveraging online business acquisitions. ➥ Strategic acquisitions can accelerate growth for buyers, but understanding the nuances of each business model is essential. ➥ The exit process has evolved, with greater emphasis on protecting seller value through careful timing and market awareness. About Andy Allaway Andy Allaway is the CEO of Empire Flippers, the #1 place to buy and sell online businesses. With deep expertise in sales, operations, and leadership in remote settings, Andy builds lean, execution-driven remote companies that scale fast, deliver results, and give employees the freedom to live unconventional, high-impact lives. Passionate about empowering remote leaders, Andy is also the creator and host of "The Leader Sip," a YouTube channel dedicated to distilling practical insights from the best business and leadership books, tailored specifically for remote executives. Connect with Andy Allaway ➥ https://bit.ly/3RtyMkE➥https://www.youtube.com/@theleadersip Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx

In this value-packed episode, Jaryd Krause speaks with Jon Elder, an Amazon veteran who has sold over $10 million worth of products and successfully exited five private label brands for $5 million. Now a strategic consultant at Black Label Advisor and the force behind Amazon Insiders—the fastest-growing newsletter for Amazon sellers—Jon brings years of hands-on experience and a deep understanding of what makes an Amazon business truly scalable. This conversation is valuable for anyone interested in acquiring and growing Amazon-based businesses. Jon breaks down what a great Amazon business looks like—from the product catalog to innovation levels and inventory management. He highlights the red flags buyers should avoid and the markers of long-term potential that smart investors should prioritize. Gain insight into:✔️ The difference between average and investable Amazon businesses✔️ Why product innovation matters more than ever in a saturated marketplace✔️ What “good” vs “bad” inventory management looks like✔️ How to scale an Amazon business post-acquisition using smart strategies✔️ When and how to turn on Amazon PPC ads for maximum impact✔️ How to get quality reviews and leverage Amazon tools for viral visibility✔️ Risks Amazon sellers must navigate—and how to stay compliant Jon also shares thoughts on emerging platforms like Root, the social media space designed specifically for Amazon brands, and how to use them as growth levers. Whether you're a seasoned investor or exploring your first acquisition, this episode delivers tactical advice from one of the most respected voices in the Amazon FBA world. Don’t miss it. Episode Highlights 04:10 – Key metrics buyers look for in an Amazon business 05:35 – Two categories of Amazon businesses that are highly desirable 12:45 – Why buyers want simplicity and clear financials 17:00 – Using PPC to build momentum early in a product launch 19:30 – How to leverage Amazon Vine for hundreds of quality reviews 22:15 – Building long-term brand credibility through authentic influencer gifting Key Takeaways ➥ Amazon businesses with $1M–$5M in annual revenue are the sweet spot for buyers, especially aggregators and private equity. ➥ Clean financials and simple operations make your business significantly more attractive to acquirers. ➥ Having a hero product is fine—but not at the expense of diversification and risk management. ➥ Amazon Vine and influencer gifting are powerful tools for building credibility and organic momentum. ➥ Starting with a smart launch strategy—using PPC and early reviews—can create a lasting flywheel effect. About Jon Elder Jon Elder is an Amazon veteran. He first started selling on the platform in 2014 and sold over $10 million until he sold all 5 of his private label brands in 2019 for $5 million. Now he works as a strategic consultant at Black Label Advisor. He also runs the fastest growing Amazon seller focused newsletter in the world called Amazon Insiders. He has one passion: seeing Amazon native brands crush it on Amazon. Connect with Jon Elder ➥ https://www.blacklabeladvisor.com/ ➥ https://blacklabeladvisor.kit.com/amazon-insiders ➥ https://x.com/blacklabeladvs Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx

In this episode of the Buying Online Businesses podcast, host Jaryd Krause sits down with Shlomo Freund, an author, speaker, digital marketer, and experienced online business buyer. Shlomo has built a portfolio of online businesses using a growth-by-acquisition strategy, and today, he’s sharing the highs, the lows, and the lessons learned along the way. Ever wondered how to keep going after a business acquisition doesn’t pan out the way you planned? Shlomo knows firsthand what it’s like to face challenges and bounce back. You’ll hear about the types of businesses he’s bought, including his very first acquisition, how he structured his second purchase, and how he’s successfully partnered with others to grow his portfolio. Plus, Shlomo reveals how he brings people into his team, the roles they take on, and how he structures incentives—whether it’s through wages, equity, or both. You’ll also get an honest look at his biggest mistakes, what he’d do differently, and his top tips for anyone thinking about buying an online business. And here’s a twist—Shlomo turns the tables and asks Jaryd about building the Buying Online Businesses community, something he’s looking to replicate with his own ventures. It’s an insightful conversation that shows just how important community can be in the world of online business. If you’re interested in acquiring online businesses, growing your portfolio, or just learning from someone who’s been through it all, this episode is a must-listen. Tune in—you’re going to love it! Episode Highlights 08:30 Identifying and adapting to changes in online business strategies. 10:00 Off-market deals vs. brokered deals - Finding the best opportunities. 12:00 Challenges with content websites and adapting to market changes. 14:00 Combining e-commerce with content sites - Building a resilient business model. 16:00 The importance of partnerships in scaling digital assets. 18:00 Building a portfolio of sub-$100K online businesses. 21:00 Community building tips and the power of consistency. Key Takeaways ➥ Growth through acquisition requires not only buying businesses but also enhancing existing assets through strategic partnerships. ➥ Building a portfolio of smaller businesses under $100K can be a strategic way to minimize risk and explore diverse income streams. ➥ Diversifying income sources within acquired businesses, like adding e-commerce to content websites, can stabilize revenue. ➥ Showing up consistently and providing value is essential for building a strong and engaged community. About Shlomo Freund Shlomo Freund is an author, speaker and digital marketer. He helps ecommerce brands scale by building strong marketing channels outside of just paid ads. He’s also acquired businesses himself and used the growth by acquisition strategy to build a portfolio of online businesses. Connect with Shlomo Freund ➥ https://assetbolt.com/ ➥ https://www.linkedin.com/in/shlomofreund/ Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx