Show Notes
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. 🎧 Listen in—and ask yourself whether you’re setting yourself up for success… or failure.
Episode Highlights 01:00 – Why most people unknowingly set themselves up for failure before they even start 06:55 – Myth-busting: Why you don’t need to know how to run or buy a business before acquiring one 10:45 – The danger of “bad” advice and why most guidance is general, not personal 13:55 – Why copying someone else’s timeline almost guarantees failure 18:30 – How unrealistic goals quietly destroy confidence and momentum 20:45 – The mental reality of buying a business and why most people aren’t prepared 24:30 – Patience vs. pressure: why counting inputs matters more than counting time 28:20 – Want vs. necessity: the single biggest reason people fail to follow through 32:40 – How pain, fear, and discomfort actually drive ambition and success
Key Takeaways ➥ You don’t need experience to get started. Most successful buyers had never run or bought a business before their first acquisition. Skills are built during the process—not before it. ➥ General advice becomes dangerous when taken as personal truth. What worked for someone else may not work for you due to differences in time, resources, credit, life stage, and risk tolerance. ➥ Unrealistic timelines create avoidable failure. Comparing your progress to others—or forcing artificial deadlines—leads to disappointment, self-doubt, and unnecessary quitting. ➥ Mental readiness matters more than capital. Buying a business requires patience, resilience, and the ability to handle rejection, uncertainty, and long stretches without visible progress. ➥ Preparation is psychological, not just financial. Due diligence, deal flow, and negotiations are mentally taxing—especially at lower price points where fewer systems and advisors exist. ➥ Stop measuring success by time. Measure inputs instead. Track actions like deals reviewed, conversations held, and due diligence completed. Progress compounds through consistent inputs, not arbitrary deadlines. ➥ Setting the bar too high too early damages confidence. Low, achievable goals build momentum. Repeated “missed” goals—even small ones—erode belief and motivation over time. ➥ Wanting a better life isn’t enough—necessity creates action. True follow-through happens when change becomes non-negotiable, not optional. ➥ Pain and discomfort are powerful drivers, not problems. Ambition is often fueled by frustration, fear, or dissatisfaction. Learning to harness that energy is key to long-term success.
Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause
➥ Buying O
More from Buying Online Businesses Podcast
In this episode of the Buying Online Businesses podcast, host Jaryd Krause interviews Lisa Williams, CEO of Hello Again, a women’s wellness e-commerce brand. Lisa shares her journey of transitioning from running a marketing agency to acquiring a brand in 2024 with zero prior M&A experience and no outside capital. She dives into how she discovered the product during her own menopause journey, structured the deal to finance it herself, navigated complex legal challenges, reformulated and rebranded the products, and scaled the business through organic growth and content creation. If you're looking to buy your first business without relying on outside investors, this episode is a masterclass in creative deal-making. Click the ‘Play’ button to get started!
In this episode of the Buying Online Businesses podcast, Jaryd Krause interviews David Barnett, an author, educator, and former business broker with over 20 years of experience buying, selling, financing, and managing small businesses. They explore concepts from David's 11th book, Business and Asset Values, diving into how opinions, personal situations, and emotions influence how people value businesses. The discussion highlights strategies for becoming an "unfocused" buyer to avoid costly emotional mistakes, objectively assessing a business's build-versus-buy replacement costs, navigating competition from strategic buyers or private equity firms, and using a sales mindset to help buyers secure better terms. Check out this video to learn how to win deals without overpaying! Link here: _____
What actually keeps someone in the game when the business fails, the money disappears, and the strategy stops working? Joe Burrell knows that feeling. His first business cost him $700 and didn’t work out. Years later, he’s been involved in 300+ transactions worth nearly $7 million. But the interesting part isn’t the acquisitions. It’s what happened in between them. In this episode, Joe and Jaryd unpack the mindset behind staying the course - why the hardest part of entrepreneurship is often the dip, how belief is built through action rather than motivation, and why constantly chasing the next opportunity can quietly destroy the compounding effect of sticking with one thing. They also break down a simple but powerful progression: desire → vision → courage → belief. Because you don't need to feel confident before you start. Sometimes confidence is what you earn by refusing to stop. 🎧 Hit play — this one is about what happens when you stay in the game long enough to get good at it.
He bought a SaaS business for $3,000. It had zero revenue. No payment gateway. Barely any real traffic. And some of the traffic being reported? It was basically the founder testing his own site. 18 months later, that same business was doing $3,000 a month in revenue. So what changed? Steven Macdonald didn't throw money at ads or try to monetize everything on day one. He knew the market, listened to customers, went all-in on SEO, and turned original research into a growth engine. He surveyed 200+ startups. Published the data. Started ranking for major OKR keywords. Built backlinks. Generated thousands of monthly visits. And kept improving the product based on what customers actually wanted. But the most interesting part might be what he didn't do. He didn't rush. Steven gave himself eight to ten years to build the business. That long-term mindset completely changed how he approached growth, product decisions, and even monetization. In this episode, Jaryd sits down with Steven to break down the $3K acquisition, how he took a zero-revenue SaaS to $3K/month, why knowing the market can matter more than the size of the deal, and how original research and AI are helping him compound organic growth. If you're thinking about buying a small SaaS, or wondering what can happen when you give a tiny business enough time to grow, this one is worth hearing. 🎧 Hit play. The acquisition cost $3K. The lessons are worth a lot more.
Buying your first business is exciting. Buying six more before you’ve figured out how to run the first one is where things get interesting. Dev Shah discovered acquisitions through Acquire.com and quickly went from being fascinated by the idea of buying businesses to actually building a portfolio of them. His first deal was Sourcely AI, a student research tool he bought for just $4,000 while it was making around $500 a month. A year and a half later, he had grown it to more than $5,000 in monthly recurring revenue and sold it for a low six-figure exit. But along the way, Dev acquired six other micro-businesses, all for less than $10,000 each, using the cash flow from his original acquisition. And that's where he learned one of the biggest lessons of his acquisition journey: just because you can buy another business doesn't mean you should. He couldn't integrate them as effectively as he expected. Some were sold. Some were shut down. Others continued running. Today, Dev has taken those lessons into a much bigger world of acquisitions. He runs a buy-side advisory firm helping search funds, startups, and other buyers source deals, conduct due diligence, negotiate, and get acquisitions across the finish line. And he's seen plenty go wrong. Sellers who disappear after an LOI. Businesses with information that turns out to be fake. Owners claiming revenue that can't actually be verified. Deals that look attractive until you start pulling apart the numbers. In this episode, Jaryd sits down with Dev to unpack what buying seven businesses taught him about moving too fast, how to build a buy box around your own skills and competitive advantages, and why serious buyers need to spend time in the market before they ever make an offer. Dev also breaks down his approach to due diligence, why you should treat those 30 days as if you're already taking over the business, how to avoid becoming emotionally attached to a deal, and why your relationship with the seller can be just as important as the numbers on the spreadsheet. From $4,000 micro-acquisitions to sourcing deals for buyers with millions of dollars behind them, Dev has seen both sides of the acquisition process. If you're thinking about buying an online business, especially for $100K or less, this conversation is full of lessons that could save you from making the same mistakes. 🎧 Hit play to hear what Dev would do differently if he could go back to his first acquisition.