Buying Online Businesses Podcast

Finding a great business is only half the battle. The harder part? Convincing a lender that you're the person who should own it. That's where most acquisitions quietly fall apart. In this episode, Jaryd is joined by Jared W. Johnson, the top individual SBA loan producer in the United States, who's helped fund more than $800 million worth of business acquisitions. But this isn't just another conver...

Everyone evaluating a business purchase today fixates on the same thing. Can this survive AI? Wrong lens. Wrong era. Wrong way to size up a deal. Tony Xu ran product and engineering at Flippa for five years before taking over as CEO. He's sat behind the scenes of thousands of transactions, tracked which categories exploded and which quietly faded, and seen firsthand what happens once AI actually t...

Most people trying to win at SEO are asking the wrong question. How do I get my traffic back? Wrong question. Wrong game. Wrong decade. Steve Wiideman has thirty years in this industry. He's seen every update, every panic, every agency pivot. And he'll tell you something most people charging you monthly retainers will never admit. The traffic isn't coming back. AI overviews are eating clicks befor...

Most people buying businesses are looking for the obvious. The obvious growth. The obvious profit. The obvious opportunity. That's exactly why they miss the best deals. Kyle Brown spent years in investment banking and private equity evaluating acquisitions before ever buying a business himself. And what he learned was simple: The businesses that look the safest aren't always the best investments....

Most people think the biggest risk in buying a business is overpaying. It's not. It's signing an LOI you don't fully understand. Moving fast because someone on the internet told you speed wins. Then finding yourself thirty, forty thousand dollars deep into a deal that was never going to close the way you structured it. Eric Hsu has seen it happen more times than he can count. Over 160 closed deals...

What if the way you've been thinking about buying a business has been costing you money before you've even made an offer? Not a little money. A lot. The kind of difference that turns a three-times multiple into a thirty-seven-times multiple. The kind of gap that separates someone who buys themselves a job from someone who builds a portfolio that works without them. Brad Sugars has been on the righ...

What if you attracted 50 buyers in two months - for a product you almost didn't list? That's not a marketing strategy. That's exactly what happened when 21-year-old Ovi Shekh posted Wisdomic AI on Acquire.com and watched his inbox fill up faster than he expected. Ovi is a CS student from Dhaka, Bangladesh. He's already exited two businesses before most people his age have submitted a single job ap...

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 sinc...

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...

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...

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 peopl...

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 exi...

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 hea...

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...

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&hel...

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...

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 finan...

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. Gua...

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 righ...

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...

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 acquisi...

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...

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 mark...

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 decade...

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 S...