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.

🎧 Hit play - this is what buying businesses really looks like.

Episode Highlights

02:27 The Career Pivot That Changed Everything – From 20 Years in Consulting to Buying Online Businesses

03:36 From $50K Deals to 7-Figure Acquisitions – How Kevin Built a 50+ Deal Track Record

06:08 The Hidden Value Most Buyers Miss – Untapped Audiences That Can Instantly Increase Revenue

09:22 The Deal That Looked Perfect… Until the Entire Team Walked Out After Closing

11:36 SaaS Due Diligence Simplified – The 4 Metrics That Actually Matter

17:01 The KPI That Signals It’s Time to Sell (Before the Business Declines)

22:14 What NOT to Buy in the Age of AI – And Where the Real Moats Still Exist

Key Takeaways

➥ The best deals aren’t found - they’re filtered. Without a clear acquisition thesis, you’ll chase instead of build.

➥ If the business can’t run without the founder, you didn’t buy an asset - you bought a job.

➥ The real cost isn’t the purchase price. It’s the capital required to grow the business after you own it.

➥ Conversion rate and churn will tell you the truth before revenue ever does - watch them closely.

➥ AI is lowering the barrier to entry. If your business can be easily copied, it’s already at risk.

➥ The biggest hidden upside in acquisitions is often an under-monetized audience.

➥ Most founders sell too late. The right time to exit is before growth starts getting harder.

About Kevin Peterson

Kevin Petersen is a serial entrepreneur and founder of WebFolio Management, a portfolio vehicle that acquires and operates small SaaS companies on behalf of investors and himself. 

Since getting started in the web-business market he has acquired dozens of internet businesses (including Picreel) and refined a deliberate, metrics-driven approach to sourcing, cleaning financials, and scaling recurring-revenue products. 

Kevin focuses on building investor-grade units with clean books and repeatable growth processes, then deciding whether to hold, scale, or exit. 

He frequently coaches other buyers and investors on building SaaS portfolios, and his playbook centers on deliberate deal selection, clean financial segmentation, and operational systems that allow multiple assets to be managed without chaos. 

Connect with Kevin Peterson

➥ https://www.linkedin.com/in/kevinpetersen1/

➥saastermind.net

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) 🔥

➥ 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.

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.

🎧 Hit play. This is the exit conversation nobody else is having.

BONUS: Get a free 30-day trial of Nathan's all-in-one podcasting platform at PodUp, or head to podallies.com to book a free 45-minute podcast strategy session – directly with Nathan himself.

Episode Highlights

07:08 The $100 Million Yahoo Offer That Got Turned Down – And the Company That Was Dead 12 Months Later

10:31 The Sunday Morning Phone Call That Changed Everything About Why He Sold Adoption.com

15:00 How Nathan Bought His Biggest Competitor Without a Single Dollar Down

18:21 Built From Scratch in 24 Months – Then Disney Tried to Buy It

23:06 The Earn-Out Trap: Why Nathan Would Walk Away From Millions Before He'd Ever Sign One Again

27:17 The 18x EBITDA Offer a Partner Killed Before Negotiations Even Started

27:52 Why a 50/50 Partnership Is Quietly the Most Dangerous Deal Structure in Business

34:00 Love-Based vs Fear-Based Decisions – The Framework That Changed How Nathan Runs Everything

37:02 How Nathan Turned His Biggest Competitor Into His Biggest Asset (Without Paying Upfront)

Key Takeaways

➥ When your business is worth more to someone else than it is to you - that's your signal to sell.

➥ Never sign an earn-out where the buyer makes all the decisions. You're handing them your money and your future in the same handshake.

➥ A 50/50 partnership sounds fair until you need to make a decision that actually matters.

➥ Your biggest competitor might be your best acquisition – buy them, absorb their traffic, and stop splitting the market.

➥ The best acquisitions don't require a big upfront payment – structure it right and the asset pays for itself.

➥ Businesses don't always go up. The founders who wait for the perfect moment often end up selling at the worst one.

➥ Brokers create competition. Competition creates leverage. Never negotiate a major exit one-on-one if you can avoid it.

➥ Lead with genuine value and build revenue around it – the freemium model is still one of the most powerful plays in digital business.

➥ The best business decisions aren't made from fear. They're made from love – for your partners, your customers, and the impact you're trying to create.

About Nathan Gwilliam

Nathan Gwilliam is a serial entrepreneur who has created and sold three digital ventures, including Adoption.com, the world’s most visited adoption platform. He grew major online communities and digital properties, and later sold Adoption.com to the Gladney Center for Adoption. Today he leads PodUp, an all-in-one podcasting platform that recently raised significant funding. Nathan’s unique journey – building, scaling, selling and reinventing digital businesses – gives him deep insight into acquisitions, growth strategy, and what it REALLY takes to exit for maximum value.

Connect with Nathan Gwilliam

➥ https://podup.com/ 

➥ https://podallies.com/   

➥ https://www.linkedin.com/in/nathangwilliam/ 

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) 🔥

➥ 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.

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:

🏦 How he lost his SBA lender mid-transaction - and saved the deal in 48 hours

💀 The post-closing liquidity trap that blindsides almost every first-time buyer

😬 Why buying slightly bigger might have changed everything

📈 The unglamorous growth playbook keeping a 20-year-old business moving forward

This isn't a success story wrapped in a bow. It's something far more valuable - an honest account of what buying a business really costs you. In money, stress, and lessons you can't learn anywhere else.

If you're thinking about buying your first business, this might be the most important episode you listen to all year.

🎧 Hit play. Real talk only.

Episode Highlights

13:32 The SBA Pre-Approval Myth That Almost Derailed the Deal

16:15 Lender Drops Out Mid-Deal - How Michael Scrambled and Saved It in 48 Hours

19:48 The $10,000 Non-Refundable Move That Kept the Seller at the Table

21:25 The 100-Hour Business Plan That Stunned Bankers on Million-Dollar Deals

27:58 The $30,000 Tech Migration Mistake That Still Haunts Him

33:45 The Post-Closing Liquidity Trap That Catches First-Time Buyers Off Guard

35:49 Why He Had to Stop Paying Himself -  And Go Back to Work Anyway

36:27 The Brutal Truth About Buying Too Small (And What He'd Do Differently)

Key Takeaways

➥ "SBA pre-approved" listings are a marketing tactic - the real approval depends on YOU as the buyer, not just the business.

➥ Losing a lender mid-deal isn't fatal - having two banks compete for your business can actually get you a better outcome.

➥ A non-refundable deposit signals serious intent and can keep a seller loyal to you when the deal gets rocky.

➥ Post-closing liquidity is the number most first-time buyers forget - 10% down is just the starting line, not the finish.

➥ Buying too small is a trap - if the business can't cover debt service, pay for growth, AND pay you, you'll end up working for free.

➥ A obsessively detailed business plan doesn't just impress lenders - it becomes your single biggest competitive advantage in a crowded deal.

➥ Technical debt is invisible until you own it - always pressure-test the tech stack before you sign, not after.

➥ Boring, stable, decades-old businesses with loyal customer bases consistently outperform shiny, high-growth ones for first-time buyers.

➥ The real cost of buying a business isn't the purchase price - it's everything that comes after the wire transfer hits.

About Michael Simpson

Michael Simpson is a business owner, acquisition entrepreneur, and National Guard serviceman who successfully bought a business using SBA financing while balancing a full-time military role and raising seven children. 

His acquisition journey included a near-deal-ending due diligence process and the challenge of replacing his SBA lender mid-transaction. Michael brings a rare, real-world perspective on resilience, risk management, and executing an acquisition under extreme personal and financial pressure.

Connect with Michael Simpson

➥ https://x.com/Michael_in_biz   

➥ https://www.discountcatholicproducts.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) 🔥

➥ 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.

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.🎧

Episode Highlights

06:09 The $0 Down Deal Structure Most Buyers Don't Even Know Is Possible

15:13 How They Bought a $1.2M Business With Just $65K Out of Pocket

18:26 Why Taking 6 Months to Close Was the Smartest Thing They Ever Did

24:09 From 60-Hour Weeks to 5: The Exact Strategy They Used to Replace Themselves

29:00 The Layoff That Forced Them All In – And Accidentally Changed Their Lives Forever

33:33 They Sold the Business… and Got Bored in Two Months. Here's Why They're Back

35:33 The Raw Truth About Mindset That Most Business Coaches Are Too Polished to Say

42:12 The Wealth Loop Nobody Talks About: How One Business Funded an Entire Real Estate Portfolio

Key Takeaways

➥ You don't need industry experience to acquire a business – the learning happens after you buy, not before.

➥ SBA financing can get you into a $1.2M business with as little as $0 down if you negotiate the deal structure right.

➥ The fastest way to scale an acquisition is to document every bottleneck, then hire to eliminate them one by one.

➥ A longer closing timeline isn't a red flag – it's free due diligence that lets you watch the business perform before you own it.

➥ The moment you stop working IN the business and start building a team around it, everything changes.

➥ Buying a business where the owner is burned out is a hidden goldmine – lower price, massive upside, ready to scale.

➥ Online businesses have no glass ceiling – unlike physical businesses, growth isn't limited by location, rooms, or geography.

➥ Business cash flow funds real estate. Real estate equity funds the next acquisition. That loop, repeated, builds serious wealth.

➥ Mindset isn't a buzzword here – it's the actual difference between people who pull the trigger and people who stay stuck researching forever.

➥ Freedom isn't something you find after you build the business. It's something you design into the business from the start.

About Alan & Mel

Alan and Mell are a husband-and-wife duo who’ve turned online business acquisitions into a lifestyle of freedom and adventure. Alan, with a background in education and technology, and Mel, a former respiratory therapist with an MBA from Ohio State’s Fisher College of Business, combined their skills to acquire three online businesses—recently exiting one successfully. Their profits helped them purchase two Airbnb properties and build a third in Belize. Thanks to the flexibility of their online ventures, they recently spent a month in Guatemala and El Salvador with their daughters for a World School program. Now, they’re under LOI for their next deal and on track to acquire three new deals within the next year.

Connect with Alan & Mel

➥ https://risingphoenixfund.org/home

➥ AI content creation platform: https://wordgenius.ai/

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) 🔥

➥ 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.

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. 🎧

Episode Highlights

05:45 The Chainsaw Analogy: Why AI Without Experience Is Genuinely Dangerous in a Deal

09:08 The Hallucination Problem: Why AI Can Lie to You During a Deal and How to Stop It

13:57 Where AI Creates the Biggest Unfair Advantage in the Acquisition Process Right Now

16:43 Prompt Engineering: The Most Underrated Skill Every Serious Buyer Needs to Master

19:44 The Rise of Agent-First Companies: What Cursor AI's $2 Billion Valuation Tells Us About the Future

22:31 The Mindset Shift Every Business Owner Must Make or Get Left Behind

28:16 AI Agents Buying From AI Agents: The Future of M&A Is Closer Than You Think

31:12 Smart Contracts, Crypto Wallets and the Death of Bureaucratic Deal Making

35:43 Fractionalised Business Ownership: How Anyone Could Invest in a Business for $50

Key Takeaways

➥ AI without experience is like handing a chainsaw to someone who's never cut down a tree. Powerful tool. Dangerous hands.

➥ AI will hallucinate during your due diligence. If you don't know how to configure it correctly, it will confidently lie to you about the business you're about to buy.

➥ Prompt engineering is the most underrated skill in acquisitions right now. The quality of your questions determines the quality of your deal.

➥ The number one reason mergers fail isn't bad financials. It's people, politics, and ego. AI is quietly removing all three from the equation.

➥ We are shifting from AI that answers questions to AI that takes actions. The buyers who understand that difference right now will have an unfair advantage for the next decade.

➥ Smart contracts, crypto wallets, and blockchain are about to collapse the layers of bureaucracy that slow every deal down. The merger process, as we know it is on borrowed time.

➥ Fractionalised ownership is coming to business acquisitions. You won't need six figures to get into a deal. You'll need the right agent and the right wallet.

➥ The future of M&A is two AI agents negotiating a deal, presenting it to their humans, and closing it on the blockchain before a bank even answers the phone.

About Haytham Allos

Haytham Allos is an M&A and AI strategist focused on how artificial intelligence is transforming the buy-side deal process. He works at the intersection of technology, data, and acquisitions, helping investors and acquirers use AI to enhance due diligence, identify hidden risks, and make better capital allocation decisions. 

Haytham specializes in applying AI tools across deal sourcing, financial analysis, operational review, and post-acquisition decision-making.

Connect with Haytham Allos

➥ https://vikk.ai/

➥ https://finance.yahoo.com/news/vikk-ai-selected-prestigious-aws-141700773.html?guccounter=1

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) 🔥

➥ 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 $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) 🔥

➥ 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.

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.

🎧 Hit play to learn how to position yourself as the buyer sellers actually want to choose.

Episode Highlights

02:53 Why Chasing Billions Is a Trap (And What Actually Builds Freedom)

12:42 The “Seasons of Life” Framework for Smarter Entrepreneurship

18:02 The Two-Way Door Rule: How Elite Entrepreneurs Make Fast, Confident Decisions

20:17 Why Most Aspiring Entrepreneurs Fail Before They Even Start

24:34 The #1 Mistake Buyers Make When Acquiring a Business

26:24 Why Most Buyers Lose Deals (And Don’t Even Know Why)

28:46 The $400 Move That Won a Multi-Million Dollar Deal

30:45 How Relationships Beat Higher Offers in Competitive M&A

32:04 The 10% Lower Offer That Still Won the Deal

35:45 SBA Buyers vs. Serious Buyers: What Sellers Actually Want

37:38 When Paying MORE Is the Smartest Financial Decision

40:01 How to Know When You’ve Found “The One” (And Go All In)

43:00 AI, Adaptation & Why Average Operators Will Get Left Behind

Key Takeaways

➥ Traditional SEO is still the foundation—AI and GEO optimization enhance it rather than replace it.

➥ Strong brand presence and mentions across multiple platforms are now more important than backlinks for AI visibility.

➥ Being associated with reputable brands or industry leaders boosts authority and trust in AI-driven results.

➥ Content hubs and semantically related pages improve AI discoverability more than focusing on keywords alone.

➥ Social media, forums, and niche communities (Reddit, Medium, Facebook Groups) contribute to AI recognition.

➥ Balance is key: optimize for AI while maintaining usability and experience for human visitors.

➥ AI content generators can efficiently create research-backed, brand-aligned, and contextually rich content.

About Ryan Condie

Ryan Condie is a serial entrepreneur, M&A advisor and founder behind Let’s Buy a Business. He has built, bought, and sold multiple digital ventures including RentLingo via a successful acquisition.

He now helps founders master deals, due diligence and exits. Ryan also serves as an advisor at Quiet Light Brokerage, where he guides buyers and sellers through evaluations, negotiations and growth opportunities that maximize exit value. His experience blends real-world deal execution with deep strategic insight. 

Connect with Ryan Condie

➥ https://ryancondie.com/

➥ https://www.letsbuyabusiness.com/

Other podcasts with Ryan;

https://buyingonlinebusinesses.com/ep-149-why-buy-a-profitable-online-business-instead-of-staring-one-with-ryan-condie-part-1/

https://buyingonlinebusinesses.com/ep-150-title-how-to-get-started-buying-profitable-online-business-with-ryan-condie-part-2/  

https://www.youtube.com/watch?v=hRv7UHDUjYA  

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) 🔥

➥ 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.

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.

🎧 Hit play and learn how to stay visible before the rules change completely.

Episode Highlights

03:10 Pivoting from SEO to GEO: How AI is Changing the Search Landscape

06:00 The Growing Importance of Brand Mentions and Broad Visibility

10:00 Leveraging Listicles, Social Media, and Mentions for Authority

14:00 Optimizing Websites for AI Agents vs. Human Users

18:00 Content Strategy for AI: Hubs, Semantic Relevance, and Queries

22:00 Auditing Your Site and Competitors for AI Visibility

24:00 Using AI Tools: Visibility Reports and Content Generators

29:00 Incorporating Brand Voice, Contextual Images, and Internal Linking

32:57 Scaling Your Business with AI-Driven Content Strategies

Key Takeaways

➥ Traditional SEO is still the foundation—AI and GEO optimization enhance it rather than replace it.

➥ Strong brand presence and mentions across multiple platforms are now more important than backlinks for AI visibility.

➥ Being associated with reputable brands or industry leaders boosts authority and trust in AI-driven results.

➥ Content hubs and semantically related pages improve AI discoverability more than focusing on keywords alone.

➥ Social media, forums, and niche communities (Reddit, Medium, Facebook Groups) contribute to AI recognition.

➥ Balance is key: optimize for AI while maintaining usability and experience for human visitors.

➥ AI content generators can efficiently create research-backed, brand-aligned, and contextually rich content.

About Rad Paluszak

Rad Paluszak is a digital marketing and SEO strategist focused on AI search, Generative Engine Optimization (GEO), and brand visibility in an AI-first internet. He helps businesses adapt beyond traditional rankings by optimizing for brand authority, entity mentions, and AI discovery across Google, ChatGPT, and social platforms. Rad specializes in visibility audits, content strategy, and future-proofing brands for generative search

Resource Links

➥ Ordering PROMO content packages (1 Free + 10 articles with images, internal linking and brand voice included): https://order.non.agency/content?referral_code=Buying_Online_Businesses

➥ Free AI Visibility Report: https://non.agency/en/service/ai-search-optimization-aio/?referral_code=Buying_Online_Businesses#ai_visibility

➥ 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) 🔥

➥ 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.

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) 🔥

➥ 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 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) 🔥

➥ 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.

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) 🔥

➥ 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.