Buying Online Businesses Podcast

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. 🎧 Tune in to learn how to design your business for growth, master your numbers, and build a team that frees you to focus on your next big move.   Episode Highlights 05:31 – Navigating acquisitions: lessons learned from evaluating, negotiating, and structuring successful deals. 08:26 – Building your inner circle: why legal, financial, and operational support are essential for scaling. 11:23 – Overcoming acquisition hurdles: managing uncertainty, setbacks, and the emotional rollercoaster of business buying. 22:39 – Planning ahead: aligning goals, systems, and strategy for sustainable expansion. 34:30 – Systems thinking: creating repeatable processes that build resilience and scalability. 35:19 – The power of partnership: how trust and complementary skills strengthen business outcomes. 38:25 – Hard-won wisdom: advice for first-time buyers on patience, preparation, and perspective. 41:00 – Education as an edge: how continuous learning fuels smarter investments and growth. 48:12 – The road ahead: building a sustainable, diversified business portfolio with long-term impact.   Key Takeaways ➥ Mentorship accelerates mastery. The right guidance can save years of trial and error. ➥ Understand your numbers. Financial clarity is the foundation of every successful acquisition. ➥ Build systems, not chaos. A strong operational structure allows growth without burnout. ➥ Customer feedback is your compass. Listening to your audience drives smarter innovation. ➥ Teamwork scales success. A capable team frees you from the daily grind and fuels sustainable growth. ➥ Stay curious. A beginner’s mindset keeps you adaptable in an evolving e-commerce landscape.   About John & Brian John & Brian are BuyingOnlineBusinesses.com graduates, online business owners, and acquisition entrepreneurs. They have a high 7-figure ecommerce business and also acquired another 7-figure online business with Jaryd Krause as their M&A advisor to add to their portfolio of businesses. They are achieving great things and have even bigger goals that they are well on their way to achieving through business acquisition and growth.    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ 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/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Buying 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. 🎧 Tune in to learn how to build, buy, and scale businesses the smart way—through systems, strategy, and structure.   Episode Highlights 09:17 – The Square Management System: Matthew’s proven framework for scaling businesses through structure, culture, and alignment. 14:10 – Lessons from investment banking: insights on spotting hidden value and capturing upside in every deal. 18:52 – Smarter deal structures: balancing growth potential with risk mitigation to protect your investment. 21:15 – The magic of recurring revenue: how predictable income streams boost valuation and stability. 23:38 – The art of integration: navigating the human and operational challenges that make or break acquisitions. 29:05 – Culture as the glue: why cultural fit is essential for seamless post-acquisition success. 33:37 – Scaling through systems: how effective management systems create control, consistency, and scalability. 37:38 – Portfolio builders’ mindset: the habits and principles of investors who consistently grow thriving portfolios. Key Takeaways ➥ Growth by acquisition starts with deep customer and market understanding, not spreadsheets. ➥ Retention drives profitability—a loyal customer base is the real engine of value. ➥ A clear pricing strategy can multiply growth potential without new customers. ➥ Culture eats strategy for breakfast—successful integrations start with people, not processes. ➥ Investment banking experience gives you the lens to structure smarter, safer deals. ➥ Different revenue types (recurring, transactional, hybrid) shape how your business is valued and scaled. ➥ The Square Management System offers a blueprint for scaling operations across multiple brands.   About Matt Person Matt Person is a seasoned corporate strategist, investor, and M&A expert with over 25 years of experience helping companies build and capture enterprise value. Currently SVP of Corporate Development at Quickbase (a Vista Equity-backed SaaS platform), he also founded Town Square Advisors, where he created the Square Management System: a proprietary framework that drives high performance through alignment, culture, and organizational design built on constrained independence.  Prior, he led global corporate development, deal execution, and growth strategy for enterprise SaaS firms like IDG and Green Street Advisors, as well as worked in investment banking and strategy consulting. Matt combines deep technical and financial expertise with operational leadership and a passion for building winning teams. On this episode of the Buying Online Businesses Podcast, he shares how you can not only buy and scale online businesses, but also structure them and your own mindset to replace your income and craft a life of freedom.   Connect with Matt Person  ➥ www.townsquare-advisors.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ 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/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

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. 🎧 Tune in to learn how to master your mental game, eliminate hidden obstacles, and finally unlock the success that’s been just one step away.   Episode Highlights 02:41 – The most direct path to success: identifying high-leverage actions instead of chasing complexity or distractions. 08:12 – Common success killers: self-sabotage, procrastination, and the subtle traps that derail high performers. 13:51 – The fear of not being ready: unpacking the mindset that stops many entrepreneurs from taking bold action. 24:26 – Balancing emotional comfort with the uncertainty of growth and why detachment is a key entrepreneurial skill. 30:08 – Performance traps: the myth of “working harder” and how the go-harder mentality leads to burnout. 37:41 – Strategic approaches to business growth: recognizing emotional bottlenecks that limit scale.  48:08 – The mindset mastery framework: practical tools to overcome internal blocks and build resilience.   Key Takeaways ➥ The biggest limiting belief in business is the “I’ll be ready once…” mindset. You already have what you need to take the next step. ➥ Identify your most direct path to success by asking, “What would someone else—less skilled or experienced—need to do to achieve this goal?” ➥ Emotional detachment is a superpower; it helps you make clear decisions without fear or bias clouding judgment. ➥ Seeking approval is deeply human, but when unmanaged, it leads to poor negotiations, people-pleasing, and self-sabotage. ➥ Performance traps like “just push harder” often backfire. Sustainable success requires rest, recovery, and self-awareness. ➥ Self-sabotage isn’t a flaw—it’s a signal. The key is understanding which mental model or emotional loop is driving your decisions.   About Itimar Marani Itamar Marani Itamar Marani is regarded as one of the top performance and mindset coaches in the world. He’s a former Israeli Special Forces operative, the youngest federal agent and air marshal in Israel’s history, a Brazilian Jiu-Jitsu black belt who’s competed at a world-class level, and a mentee of the Mossad’s chief psychologist.  He has since coached hundreds of 6–9 figure entrepreneurs, executives, traders, and pro athletes to break through performance plateaus, eliminate mental drag, and operate at their highest level under pressure. His clients have exited companies for nine figures, raised hundreds of millions of dollars, and entered top ten rankings in the world, among other results.   Connect with Itamar Marani  ➥ https://itamarmarani.com ➥ https://itamarmarani.com/book ➥https://buyingonlinebusinesses.com/ep-240-how-emotional-intelligence-is-your-secret-weapon-to-unlocking-your-greatest-potential-in-business-with-itamar-marani/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ 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/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

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.  🎧 Tune in to discover how to scale smarter, sidestep common mistakes, and set your business up for lasting success.   Episode Highlights 05:15 – The early challenges of manufacturing, distribution, and scaling operations in the fashion e-commerce space. 09:14 – Burnout, exhaustion, and the difficult decision to sell her business despite years of effort and growth. 25:06 – The costly mistakes founders make when scaling—such as overcommitting to leases, staff, or luxury expenses. 29:18 – Building systems that allow freedom: how to design businesses that thrive without the founder’s constant presence. 31:00 – Paid ads as gasoline on what already works, and why they can’t fix fundamental conversion problems. 34:35 – How to improve conversion rates by simplifying “click, click, buy” and removing common objections like unclear shipping, returns, or sizing. 38:00 – Product-market fit: why proven, desirable products should be prioritized before scaling ad spend.   Key Takeaways ➥ Building an e-commerce business requires patience, adaptability, and resilience—especially when scaling introduces new operational challenges. ➥ Burnout can be a signal that it’s time to reassess or even exit; knowing when to let go is as important as knowing when to push forward. ➥ Scaling too quickly with fixed overheads like leases, staff, or luxury purchases can cripple profitability; stay lean and flexible. ➥ Effective paid ads amplify what already works—they’re not a fix for poor products, broken websites, or unclear messaging. ➥ Strong ad creative is crucial; speak directly to customer benefits rather than product features to cut through the noise.   About Jodie Minto Jodie Minto is an award-winning e-commerce mentor, founder of a seven-figure fashion brand, iland co., podcast host, and speaker based on Australia's Central Coast of NSW. Jodie is also a certified Digital Marketer, Meta Ads Specialis,t and Life Coach. Jodie started her online fashion store from scratch while working full-time, juggling young kids, and living in the Middle East. Today, that business, iland co., is a seven-figure online brand with stockists and customers worldwide. Jodie sold that business in 2023 and now supports other women in growing their e-commerce businesses through her coaching programs. Jodie also hosts the popular e-commerce podcast Online Store Success, which reached number 2 in marketing podcasts in Australia for two weeks straight and frequently sits in the top 30 in Australia, Europe, the Middle East, and the United States.   Connect with Jodie Minto  ➥ https://www.jodieminto.com/  ➥ https://www.instagram.com/iamjodieminto/     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ 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/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

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. 🎧 Tune in to explore how mastering GEO can position your business ahead of the competition and right into the spotlight of AI-driven discovery.   Episode Highlights 09:05 – Why GEO matters in 2025: AI assistants are replacing search engines as the go-to for answers and recommendations. 13:25 – How ChatGPT, Bing Copilot, and other LLMs weigh authority and context differently from Google’s link-based rankings. 22:30 – Building credibility for GEO: why brand mentions, authentic discussions, and trusted sources matter more than backlinks. 33:35 – Case studies reveal GEO’s speed: top AI recommendations and tripled Reddit traffic achieved in just weeks. 41:14 – Matching platforms to your niche—Reddit, Wikipedia, or forums—improves relevance in generative search results. 42:23 – Looking ahead: how GEO will evolve as AI search expands, and why staying agile keeps brands visible.   Key Takeaways ➥ Generative Engine Optimization is essential for brands that want to appear in AI-generated answers, not just search listings. ➥ Large language models reward credibility, context, and recency, creating new levers for visibility beyond backlinks. ➥ Auditing how AI tools surface your brand helps pinpoint weaknesses and uncover fast growth opportunities. ➥ Engagement on high-trust platforms—Reddit, Wikipedia, or niche forums—can strongly influence recommendations from ChatGPT and similar tools. ➥ GEO delivers results quickly, making it a valuable complement to SEO’s slower, compounding gains.   About Dom Wells Dom Wells is the founder and CEO of Onfolio Holdings, Inc. (Nasdaq: ONFO), a public holding company of small profitable online businesses.   Connect with Dom Wells ➥ Free Audit! - https://pacegenerative.com/prtnr/2538/➥ Onfolio.co    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ 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/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

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 🎧 Tune in to learn how AJ turned a $50K deal into a reliable income stream—and how you can apply the same strategies to your own acquisition journey.   Episode Highlights 09:47 – Llearning how to properly evaluate businesses instead of jumping straight into a deal. 13:38 – Defining non-negotiables: valuing time, lifestyle, and family more than owning a “sweet deal.” 18:22 – How looking at hundreds of businesses sharpened AJ’s ability to spot red flags and opportunities. 21:14 – There are no unicorns—every business has cons; it’s about choosing what risks you can manage. 26:55 – Why the decision to “pull the trigger” is the hardest part of the acquisition journey. 35:52 – Advice for first-time buyers: don’t skip the learning stage—education reduces fear and regret. 41:55 – The difference between being a business operator and becoming a true owner with leverage. Key Takeaways ➥ There’s no such thing as a perfect business. Every deal has risks; the key is knowing which ones you can live with and mitigate. ➥ Start with education. Skipping the learning phase leads to regret; preparation makes the acquisition less scary and more strategic. ➥ Taking the leap is the hardest part. Eventually you must stop analyzing and trust your due diligence to move forward. ➥ Aim to work on the business, not in it. Leveraging teams and managers turns you from operator into true owner. ➥ Bigger opportunities become realistic after the first acquisition. The initial win builds confidence to pursue larger, even debt-financed, deals. About AJ AJ is a BuyingOnlineBusinesses.com graduate who went from being a corporate employee running a large IT team for a global bank. To now an online business owner and building a portfolio of businesses.    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ 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/ ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

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. 🎧 Tune in now to hear how to prepare, structure, and execute smarter exits.   Episode Highlights 04:50 – Clean books, systems, and reduced key-person dependency: the essentials for any exit. 06:50 – Why every exit is messy—buyers always renegotiate during LOI. 08:30 – Sophisticated vs. inexperienced buyers: how the right questions signal experience. 09:35 – Knowing what really matters in due diligence vs. what’s just “wonky” small-business noise. 11:20 – Why trust and fairness between buyer and seller are critical when numbers vary near close. 12:50 – Sellers must keep operating like they won’t exit—taking the foot off the gas can kill deals. 18:00 – Why tax planning is just as important as negotiating the sale price. 25:40 – Selling fast matters—waiting too long risks copycat competitors and valuation drops. 27:40 – Regulation, trucking, and AI adoption: why safety perception, not data, drives adoption speed.   Key Takeaways ➥ Prepare early. Clean financials, diversified revenue streams, and reduced key-person dependency are critical to maximizing valuation. ➥ Buyers are risk-averse. Expect tough questions in due diligence—not personal attacks. Sophisticated buyers ask the right way, but all buyers are trying to mitigate risk. ➥ Deal structures matter. Cash is king for sellers. Earn-outs, seller notes, and rollover equity all come with risks—align them with your personal life stage and goals. ➥ Don’t take your foot off the gas. Deals can drag on for months. Keep running your business as though it won’t sell; growth during due diligence strengthens your negotiating power. ➥ Surround yourself with the right advisors. A good CPA and financial advisor can save millions in taxes and structure your exit properly. ➥ AI is changing the game. It will automate “crappy work,” commoditize parts of business, and put greater emphasis on distribution, brand, and audience trust. ➥ Faster is better. Once you decide to sell, speed matters—because markets and competitors don’t wait.   About Anthony Franco Anthony Franco is a seasoned founder, operator, and dealmaker who’s built and sold seven companies—six of them successfully, including two to publicly listed firms.  After working closely with the team at OneReach.ai, he realized traditional frameworks like Lean and Agile just don’t cut it in today’s fast-moving, AI-driven world. That insight led to the creation of the WISER Method—a new approach that helps founders build smarter, scale faster, and exit more strategically. He’s also a licensed business broker, and on his own podcast How to Founder, he shares real-world strategies for building businesses that are easier to operate and more valuable to sell. Connect with Anthony Franco ➥ https://www.linkedin.com/in/anthonyfranco/ ➥ https://www.aifirstprinciples.org/ Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ 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/ ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

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. 🎧 Tune in now and learn what it really takes to replace your income with a SaaS acquisition.   Episode Highlights 09:21 – Learning from others’ success can inspire acquiring an existing business instead of starting from scratch. 14:16  – Defining an ideal business model and price range narrows the search effectively. 17:11 – Focusing on businesses aligned with personal strengths leads to better outcomes than chasing every opportunity. 20:35 – Studying case studies and industry insights accelerates learning and reduces mistakes. 26:37 – Audience trust and built-in channels are more valuable than the product itself. 43:20 – Avoiding small deals and aligning acquisitions with lifestyle and skills improves success. 47:38 – Buying the right SaaS can replace traditional income while leveraging personal strengths effectively.   Key Takeaways ➥ Acquisitions can accelerate entrepreneurship—buying an existing business allows leveraging capital and skills to bypass the hardest startup challenges. ➥ Understanding your strengths and weaknesses is essential to narrowing search criteria and finding the right business model and price range. ➥ True value lies in the audience, reputation, and established distribution channels—not just the product or code. ➥ Preparation and research, including learning from others’ experiences and industry content, reduce risk and improve outcomes. ➥ Mindset, persistence, and patience are critical when evaluating hundreds of businesses to find the right fit. ➥ Post-acquisition growth is most effective when leveraging existing channels, retention strategies, and organic traffic. ➥ Being selective and strategic—rather than opportunistic—ensures acquisitions provide both ROI and lifestyle freedom.   About Matthew Tse Matthew Tse was a career software engineer in big tech & quant finance. He decided he wanted a more free & fulfilling life, and eventually stumbled his way into acquiring improvmx.com, which he's now running and growing.   Connect with Matthew Tse ➥https://www.linkedin.com/in/matthew-t-15565736/ ➥matthewtse.com ➥https://buyingonlinebusinesses.com/ep-212-how-to-start-buying-flipping-small-saas-businesses-with-andrew-pierno/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ 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/ ➥ GoDaddy (Website Hosting) - https://bit.ly/3YiRkWV ➥ Rank Math (WordPress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

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. 🎧 Tune in now to learn how to grow through acquisition… without blowing up your business in the process.   Episode Highlights 06:30 – The importance of understanding the buyer’s mindset, especially when preparing to exit your business. 08:45 – Common reasons businesses fail to sell — including overvaluation, poor documentation, and lack of transferable leadership. 11:20 – Why “deal fever” can cloud entrepreneurs’ judgment and lead to bad acquisitions. 14:10 – Cultural fit and leadership alignment: often the real reasons integrations fail after a deal. 22:50 – Lessons learned from failed deals and red flags to look out for before signing. 26:30 – Strategic vs. opportunistic acquisitions — why clarity in intent is key. 28:45 – How to prepare your business for exit years in advance, including systemization and leadership planning.   Key Takeaways ➥ Being selective is critical—just because an opportunity arises doesn’t mean it’s the right fit for your business or your life. ➥ The buyer’s perspective matters—sellers must see their business through the lens of the acquirer: is it transferable? sustainable? well-documented? ➥ Leadership and culture are make-or-break factors in post-acquisition integration. Without the right leadership in place, the acquired business often struggles. ➥ Deal fever is real—don’t let excitement override discipline. Stick to your acquisition criteria and due diligence process. ➥ Exiting a business is a long game—the most successful exits come from those who plan years, building systems and leadership teams that can thrive without the founder. ➥ Avoiding mistakes means preparation, patience, and perspective—take your time, ask the right questions, and align your acquisitions with long-term strategy.   About Michael Vann Michael Vann is the President of The Vann Group, a family-owned firm that provides strategic consulting and transactional advisory services to privately held businesses. With over 25 years of experience, Michael helps owners scale, plan for succession, and maximize value. He’s also a principal at Eaton Square, a global investment banking firm, and a certified Predictable Success Scale Architect. Michael has advised on deals up to $50 million across industries like manufacturing, services, construction, and hospitality. He’s the co-author of Buying Out the Boss and the forthcoming High Performing Value, and frequently speaks on value building and business transitions. Michael lives in South Hadley, Massachusetts, with his wife, two daughters, and one unruly pup.   Connect with Michael Vann ➥https://www.linkedin.com/in/michaelvann/  ➥www.vann-group.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ 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/ ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

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. 🎧 Listen now and learn how to exit your business the smart way. Episode Highlights 02:18 – Why most sellers leave money on the table when exiting their business 05:42 – How owner dependence and single-source revenue can destroy valuation 08:15 – Common risks in the current market, including tariffs and environmental changes 11:35 – Value drivers Domenic looks for when assessing a business for sale 14:50 – The importance of due diligence and how small oversights can become costly 17:30 – Why sellers must always be “exit-ready,” even if they’re not planning to sell soon 20:10 – Choosing the right advisory team: lawyers, accountants, and M&A experts who can make or break your exit Key Takeaways ➥ Seller mistakes are costly. Failing to prepare for an exit can result in leaving hundreds of thousands—or even millions—of dollars on the table. ➥ Owner dependency kills value. Businesses overly reliant on the owner, single customers, or single traffic sources are heavily discounted by buyers. ➥ Market conditions matter. External factors like tariffs, environmental shifts, or regulatory changes can impact valuation. Smart sellers plan for these contingencies in advance. ➥ Value drivers determine your sale price. Revenue diversity, strong cash flow, and documented systems all increase buyer confidence and the multiple you can command. ➥ Due diligence is non-negotiable. Small errors or overlooked liabilities can derail a deal. A proactive approach prevents last-minute surprises. ➥ Always be exit-ready. Even if you’re not planning to sell, setting up your business for a smooth exit ensures you’re prepared for unexpected life events or market opportunities. ➥ The right team is critical. Experienced lawyers, accountants, and M&A advisors can prevent deal disasters and protect your financial outcome.   About Domenic Rinaldi A seasoned M&A adviser, Domenic Rinaldi is the Owner and Managing Partner of the firm, Sun Acquisitions. He also founded K2Adviser to educate business owners on the requirements for a successful exit, acquisition, or scaling process.     Connect with Domenic Rinaldi ➥https://buyingonlinebusinesses.com/ep-087-why-you-need-seasoned-vets-on-your-team-when-buying-selling-businesses/ ➥www.sunacquisitions.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ 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/ ➥ GoDaddy (Website Hosting) - https://bit.ly/3YiRkWV ➥ Non Agency (SEO Audit) - https://bit.ly/3EPd7OZ ➥ Market Muse (Content Marketing Software) - https://bit.ly/3Me39L0   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.