Buying Online Businesses Podcast

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 diffe

In this episode of the Buying Online Businesses podcast, Jaryd Krause speaks with Jpaul, a graduate of the Buying Online Businesses community who recently purchased his very first ecommerce business. JPaul will take you through the entire journey, from deciding to invest in an online business to finally acquiring one worth $5,000 per month in just five months. JPaul candidly shares the ups and downs of his experience, offering valuable insights into the challenges and triumphs that come with buying an online business for the first time. He discusses why he chose this path, how long the process took, and how many businesses he evaluated before making the final decision. He also opens up about the influence of external opinions, how they affected his journey, and how he ultimately stayed focused on his goal. In this engaging conversation, JPaul and Jaryd discuss: Why JPaul wanted to buy an online business and what motivated him to take the plunge The detailed due diligence process and why some businesses didn&

In this episode of the Buying Online Businesses podcast, host Jaryd Krause speaks with Rafal Chomsky, a performance marketing expert known for helping brands double their revenue, without increasing ad spend. Rafal brings a wealth of experience in Meta Ads, Google Ads, SEO, and team-led digital strategies that have generated millions in client revenue. Together, they explore how Rafal has achieved results like turning $1,600 in ad spend into $10,000 in revenue within just three months, and how his clients have scaled from $50K to $100K revenue while maintaining the same ad budgets. The conversation dives into why most businesses are leaving money on the table by relying too heavily on AI-driven campaigns like Google Performance Max or Meta’s automated systems, and what can be done instead to take back control. This conversation delves into the key aspects of scaling online businesses through performance marketing, including: ✔️ Why “set and forget” ad strategies fail in today’s market✔

In this special episode of the Buying Online Businesses podcast, Jaryd Krause sits down with Michael Frew, M&A advisor at WebStreet (formerly Empire Flippers Capital), to answer those exact questions—and more. Michael’s journey is a masterclass in strategic growth: from buying his first Amazon affiliate site to managing a multi-eight-figure portfolio of digital businesses across SaaS, e-commerce, content, and ad-based models. With a background in business, economics, and over 20 years in software development, Michael brings a rare blend of technical and financial insight into what makes a great acquisition—and what to avoid at all costs. In this episode, you will learn: How do you assess your budget and decide the right entry point for buying a business? Why can some deal structures kill a deal, and what works better? What did Michael’s multiple acquisitions teach him about risk, leverage, and operational focus? The evolving role of AI in online business—and whether it&rsquo

What if the biggest business opportunity of the next decade wasn’t just about what you buy or sell… but how you do it? In this eye-opening episode of the Buying Online Businesses podcast, Jaryd Krause sits down with futurist, author, and AI evangelist Adam Boostrom to explore how artificial intelligence is not only revolutionizing online business—but completely transforming the way we buy, grow, and exit them. With degrees from the University of Chicago and UC Berkeley, Adam is no stranger to complex systems. He’s advised leaders, written bestselling sci-fi novels like Athena’s Choice, and now spends his time helping business owners reimagine what’s possible in the AI age. Together, Jaryd and Adam break down: How AI and AI agents can help you identify the right business to buy—faster and more accurately Ways to train AI tools to uncover financing options and analyze the perfect business size for your goals How to supercharge growth using AI-powered insights pulled d

When it comes to business, the goal isn’t just a big exit—it’s about building something so empowering that staying in or stepping away both feel like exciting options. In this episode, Jaryd Krause is joined by Raleigh Williams, a former Mergers & Acquisitions lawyer turned successful entrepreneur. Raleigh left his law career after just nine months to start an escape room business, which he scaled and sold for eight figures. Now a father of three and husband to a breast cancer survivor, Raleigh now helps entrepreneurs “take chips off the table” and reconnect with the creativity and joy that originally drove them into business. The conversation dives deep into Raleigh’s journey—from walking away from law, to building a multi-million-dollar company, to writing a powerful book that helps founders navigate the emotional rollercoaster of exits and acquisitions. For entrepreneurs wondering whether to sell, grow, or rediscover their passion for their business, this episo

In this special episode, Jaryd Krause sits down with Beau Eckstein to explore how aspiring entrepreneurs can buy a $1 million business with as little as $25,000 using SBA financing. Beau is a franchise and SBA loan expert, a seasoned business ownership coach, and the host of the Investor Financing podcast. With over 26 years of experience in lending, financing, and business acquisitions, he has helped thousands of entrepreneurs secure funding and successfully transition from employees to business owners. Throughout the episode, Beau shares his insights on navigating the SBA loan process—from understanding eligibility and repayment terms to exploring what kinds of businesses qualify. He and Jarrah also dive into creative deal structures that allow buyers to acquire businesses with minimal capital, the risks involved, and why commitment is essential when it comes to buying a business. Beau emphasizes building wealth through smart acquisitions and explains how owning multiple SBA-backed businesses can lead

Many business owners overlook a powerful strategy hiding in plain sight—using their marketing budget to fuel acquisitions and build a portfolio of successful businesses. In this episode of the Buying Online Businesses podcast, host Jaryd Krause speaks with Marty Fahncke, a seasoned marketer with over 30 years of experience in business growth and scaling. With more than two decades in mergers and acquisitions, Marty has helped businesses reach over a billion dollars in revenue and has executed more than $450 million in M&A transactions. This conversation delves into the key aspects of acquiring and selling online businesses, including: ✔️ The types and sizes of businesses that are ideal for acquisition✔️ Common mistakes sellers make and how to avoid them✔️ Strategies for bolting on businesses to an existing brand✔️ The process of identifying, acquiring, and financing the right business✔️ The "leaky bucket" problem and how businesses can save thousands of dollars per month For anyone looking to scale

In this episode, we feature a thought-provoking conversation with Michael Frankel, the founder and managing partner of Trajectory Capital. With decades of experience in corporate development, innovation strategy, and corporate ventures, Michael has held C-level roles at prominent companies like Deloitte, Lexis Nexis Group, GE Capital, and VeriSign. Having participated in over 110 deals throughout his career, he brings valuable insights to the table. They dive into the world of Mergers and Acquisitions (M&A), exploring why it can serve as a strategic "cheat code" for scaling businesses. However, as Frankel emphasizes, M&A isn't a one-size-fits-all solution. The discussion covers how business owners can evaluate whether acquisitions are the right growth strategy and what considerations are essential for success. Michael shares useful tips on: Developing a clear acquisition strategy that aligns with business goals Identifying suitable targets, whether for products, technology, talent, or market expansio

When acquiring an e-commerce business, conducting thorough legal due diligence is essential to mitigating risk and ensuring a sound investment. Overlooking critical legal aspects can lead to unforeseen liabilities, intellectual property disputes, or tax complications that may jeopardize the deal. In this episode, Jaryd Krause speaks with Paul Rafelson, a seasoned attorney with over 15 years of experience in corporate law, M&A, intellectual property, and tax matters. A highly regarded expert in the e-commerce space, Rafelson is frequently cited in major news outlets and was the most referenced source in the U.S. government’s investigation into Amazon’s business practices regarding third-party merchants. Before launching his private practice focused on e-commerce businesses, he held in-house legal positions at major corporations such as Microsoft, Walmart, and General Electric. This discussion explores the most common legal due diligence mistakes buyers make when acquiring an e-commerce business

How do you build a portfolio of businesses using the growth by acquisition method? For today’s episode of Buying Online Businesses podcast, Jaryd is joined by Link Moser—an accomplished marketing executive with over 25 years of experience in B2B digital marketing. Link has a proven track record in SEO, SEM, and PPC campaigns that drive online visibility, fuel revenue growth, and enhance business performance. He’s also an expert in UX-driven website development, leveraging mobile-first strategies to maximize ROI. Beyond marketing, Link is an entrepreneur who has successfully used the growth by acquisition model to expand his business portfolio. In this episode, they dive into how he transitioned from running a hosting business with strong recurring revenue to acquiring multiple businesses as a strategic way to scale. They discuss the types of businesses Link purchased, the deal structures, financing strategies, and the lessons he learned—both the wins and the challenges. Link also share

Acquiring and scaling an online business requires more than just financial investment—it demands the right mindset, strategic preparation, and a deep understanding of the evolving digital landscape. In this special episode of the Buying Online Businesses podcast, Jaryd Krause answers the most pressing questions submitted by his audience—questions they would ask during a one-on-one coaching session. From securing financing and selecting the right business model to navigating AI’s impact on online businesses, Jaryd provides in-depth insights, real-world examples, and practical strategies for sustainable growth. You will learn valuable knowledge on minimizing risks, leveraging AI for success, and developing the mindset needed to thrive in the online business space. This episode is designed to help entrepreneurs make confident, informed decisions on their journey to acquiring and scaling digital assets. Tune in now!     Episode Highlights 02:00 Do’s and Don’ts when acquirin

Many buyers overlook one of the most valuable yet intangible assets that come with acquiring an online business.  This episode features Ross Gerson, founder of DealSlide.com and a former broker at Empire Flippers. With extensive experience on both the buy and sell sides of online business acquisitions, Gerson shares key insights into the most frequent mistakes buyers and sellers make—and how to avoid them. The discussion covers several compelling topics, including Krause’s near-experience as a broker at Empire Flippers, a role Gerson had originally approached him for. Gerson also explains his transition into acquisition advising and consulting, detailing his work with WebStreet and his involvement in acquiring over 15 to 20 content sites. You will gain valuable insights into critical acquisition mistakes, such as the importance of direct communication with sellers, defining clear acquisition criteria, and navigating the transition period after a purchase. The conversation also highlights Deal

Many people want to buy an online business but feel unsure about legal fees, when to hire a lawyer, and what legal due diligence involves. This podcast episode answers those questions. In this episode of the Buying Online Businesses podcast, Jaryd Krause talks with business attorney Eric Hsu. Eric helps professionals leave corporate jobs and start their own businesses by buying existing ones. He focuses on business purchases, offering advice on deal structures, legal risks, and market trends. He also shares helpful content on X, LinkedIn, and his blog. Unlike many lawyers, Eric works only on the buyer’s side, which means he is fully focused on protecting buyers. Jaryd and Eric discuss key legal steps in buying a business, including when legal due diligence is needed, what it involves, and how much it costs for deals of different sizes. They also explain the legal work done for letters of intent (LOI), asset purchase agreements, and other contracts. The conversation covers how buyers can include legal fe

How much do software businesses sell for in the seven, eight, or even nine-figure range? This episode of the Buying Online Businesses Podcast dives into what it takes to sell or buy a SaaS company. Host Jaryd Krause speaks with Diamond Innabi, an expert in buying and selling software businesses. With over 10 years of experience, she has helped close successful deals in industries like energy, government, education, real estate, and technology. Diamond understands the challenges that come with selling a software company, from making sure sellers get full credit for their recurring revenue to explaining complex technology to buyers. She also knows how to position businesses with high customer concentration and other tricky factors in a way that attracts the right buyers. In this episode, listeners will learn: ✅ How long it takes to prepare a business for sale (sometimes up to two years!)✅ What needs to happen before a business is ready to sell✅ How software companies in the $15M - $150M range are valued✅ The bi

In this special episode, Jaryd Krause speaks with Michael Kerr, a seasoned small business advisor, business broker, and registered valuer. As the founder of Kerr Capital, Michael has spent over 20 years helping business owners increase their business value and sellability before exiting. He also provides expert guidance for owners who receive unexpected offers, ensuring they make informed decisions rather than rushing into a sale. Throughout the discussion, Michael shares essential strategies for a successful business exit, including the three critical questions every owner must ask before selling. He and Jaryd cover key topics such as: ✅ The timeline for selling a business and how to prepare in advance✅ The risks of signing an NDA too soon when approached by a buyer✅ Strategies to de-risk a business and secure a higher valuation✅ How investors and companies can approach business acquisitions with patience and the right timing. With extensive experience in banking, accounting, fund management, and tech startu

In this latest episode of the Buying Online Businesses podcast, Jaryd Krause, dives into the intricacies of online business acquisitions with guest Fiona Laidlaw. Fiona is a senior M&A broker and certified M&A advisor at Flippa.com, bringing over six years of experience and a track record of more than 100 successful deals. Specializing in high-value transactions, Fiona works with SaaS, e-commerce, and app-based businesses, often exceeding the seven-figure range, and focuses on clients across the APAC region. In this episode, Jaryd and Fiona explore the common pitfalls that can derail online business acquisitions, revealing unexpected mistakes made by both buyers and sellers. They discuss what it takes to become an attractive buyer or seller, the importance of relationship-building in transactions, and how trust can make or break a deal. The conversation also touches on navigating different deal structures, price ranges, and strategies for fostering collaboration between parties. With Jared’s ext

What if every business problem—whether it’s a lack of cash flow, resources, or room to grow—could be solved by buying another business? And what if the price or your current finances didn’t have to hold you back? On this episode of the Buying Online Business podcast, host Jaryd Krause talks with Tom Shipley, a seasoned entrepreneur, investor, and expert in mergers and acquisitions (M&A). Tom has built brands that generated over $2 billion in sales and raised more than $100 million for business acquisitions. He is also the co-founder and CEO of Ava, a company that specializes in helping businesses grow through acquisitions. In their conversation, Tom shares how he got started in acquisitions, including his first deal, which helped him triple his business in a short time. He explains when acquisitions make sense, when they don’t, and how to avoid deals that might drain a business’s resources. Listeners will also hear about: Simple strategies for financing and structuring

Valuing an online business can be a complex process, especially if you're navigating different business models, price ranges, and niches. How do you know what an eCommerce or SaaS business is really worth—and how do you avoid the pitfalls that both buyers and sellers often fall into? In today’s episode of the Buying Online Businesses Podcast, host Jaryd Krause sits down with Ryan Hutchins, a serial entrepreneur and business valuation expert. Ryan shares his experience as the owner of Peak Business Valuations and several other ventures, including plumbing companies, a multi-location bakery, a pizza restaurant chain, and even a stripping company. His unique background offers incredible insights into the world of business valuations, acquisitions, and investing. Together, Jaryd and Ryan dive deep into SBA acquisitions, exploring everything from common mistakes buyers and sellers make to the key differences between valuing eCommerce businesses and SaaS businesses. They discuss the importance of workin

In this episode of the Buying Online Businesses podcast, Jaryd Krause chats with Ben Dankiw about two exciting topics: the changing world of SEO with generative AI and what it’s like to sell a business and figure out what’s next. Ben is a PPC expert and even a mathematician, with over 12 years of experience helping big brands like Porsche and Canadian Tire succeed online. He shares his story of selling a big part of his agency, what that process was like, and how he’s planning his next steps. Jaryd also gives Ben tips on how to take time to relax, reset, and choose the right business model that fits his goals and lifestyle. They also dive into the future of SEO and ads. With Google no longer dominating search, platforms like Bing, Reddit, and others are changing the game. Ben and Jaryd talk about how businesses can keep their websites visible and what’s next for PPC ads, including trends for platforms like Meta in the coming years. If you own a website, are thinking about buying o