Everyone wants to know how to buy a great business.

Almost nobody talks about how great businesses quietly become bad deals.

After more than 300 business transactions, Joe Burrill has seen it happen time and time again. Sellers mentally check out months before they list. Buyers obsess over valuations while missing the risks that actually matter. And now, with AI changing the way online businesses are built, bought, and grown, the gap between good buyers and great ones is only getting wider.

So what should you actually be looking for?

In this episode, Jaryd sits down with Joe to unpack the lessons he's learned from brokering hundreds of online business sales. They explore why the best deals aren't always the fastest-growing ones, how experienced buyers think about traffic, revenue diversification, and risk, and why a simple conversation between buyer and seller can be more valuable than another spreadsheet.

They also dive into how AI is reshaping acquisitions. Why content businesses aren't dead. Why SEO still matters. And where new buyers are getting due diligence completely wrong by relying too heavily on AI instead of using it as a tool.

If you're thinking about buying your first online business - or your next one - this episode will change the way you evaluate opportunities.

Because finding a business to buy isn't the hard part.

Knowing which one is actually worth owning is.

🎧 Hit play and learn what 300+ deals have taught Joe that most buyers never find out until it's too late.

 

Episode Highlights

03:32 – How Joe Turned One Website Into a Career—and Eventually 300+ Business Deals 

08:31 – The #1 Mistake Sellers Make That Quietly Destroys Their Business Value Before an Exit 

12:02 – The $15K Deal That Used a $2K Holdback to Get Both Buyer and Seller to Say Yes

18:24 – The New Rules for Buying Content Websites in an AI-First World 

24:08 – Why AI Won't Replace SEO—and the Costly Mistake Buyers Keep Making During Due Diligence

29:18 – The $172K Valuation Error AI Completely Missed—and Why Human Judgment Still Wins

37:15 – If You Had $20K–$100K Today, Here's Exactly What Joe Would Look For in an Online Business 

 

Key Takeaways

➥ The fastest way to kill your exit? Stop running the business before it's sold. Buyers don't buy potential—they buy momentum.

➥ Deals close on trust, not spreadsheets. Strong buyer-seller relationships solve problems that contracts can't.

➥ One traffic source is a liability. Diversification is a premium. The more ways a business earns traffic and revenue, the more valuable it becomes.

➥ AI is a powerful assistant—not your deal advisor. It can speed up due diligence, but it can't replace experience, judgment, or pattern recognition.

➥ Content websites aren't dead. Generic content is. The winners are building brands, authority, and original insights that AI can't replicate.

➥ Creative deal structures create better outcomes. Seller financing, holdbacks, and flexible terms often turn stalled negotiations into closed deals.

➥ Buy the business you're best positioned to grow—not just the cheapest one you can afford. Your competitive advantage matters more than the asking price.

 

About Seph Fontane Pennock

Seph Fontane Pennock is a serial entrepreneur and 8-figure exit founder who built PositivePsychology.com from a personal blog into one of the world's most visited mental health platforms, serving over 19 million users. He grew it to a PE acquisition without spending a dollar on ads, relying purely on SEO-led content strategy. Post-exit, he co-founded the SaaS platform Quenza and has since launched Regenerated.com. Seph is now an active investor and builder.

 

Connect with Seph Fontane Pennock

➥ https://www.linkedin.com/in/seph-fontane-pennock-94666421/  

➥ https://psychology.com/  

 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Online Business Due Diligence Services -https://buyingonlinebusinesses.com/duediligence

 

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.

Everyone wants to know how to buy a great business.
Almost nobody talks about how great businesses quietly become bad deals.
After more than 300 business transactions, Joe Burrill has seen it happen time and time again. Sellers mentally check out months before they list. Buyers obsess over valuations while missing the risks that actually matter. And now, with AI changing the way online businesses are built, bought, and grown, the gap between good buyers and great ones is only getting wider.
So what should you actually be looking for?
In this episode, Jaryd sits down with Joe to unpack the lessons he's learned from brokering hundreds of online business sales. They explore why the best deals aren't always the fastest-growing ones, how experienced buyers think about traffic, revenue diversification, and risk, and why a simple conversation between buyer and seller can be more valuable than another spreadsheet.
They also dive into how AI is reshaping acquisitions. Why content businesses aren't dead. Why SEO still matters. And where new buyers are getting due diligence completely wrong by relying too heavily on AI instead of using it as a tool.
If you're thinking about buying your first online business - or your next one - this episode will change the way you evaluate opportunities.
Because finding a business to buy isn't the hard part.
Knowing which one is actually worth owning is.
🎧 Hit play and learn what 300+ deals have taught Joe that most buyers never find out until it's too late.
&nbsp;
Episode Highlights
03:32 &ndash; How Joe Turned One Website Into a Career&mdash;and Eventually 300+ Business Deals&nbsp;
08:31 &ndash; The #1 Mistake Sellers Make That Quietly Destroys Their Business Value Before an Exit&nbsp;
12:02 &ndash; The $15K Deal That Used a $2K Holdback to Get Both Buyer and Seller to Say Yes
18:24 &ndash; The New Rules for Buying Content Websites in an AI-First World&nbsp;
24:08 &ndash; Why AI Won't Replace SEO&mdash;and the Costly Mistake Buyers Keep Making During Due Diligence
29:18 &ndash; The $172K Valuation Error AI Completely Missed&mdash;and Why Human Judgment Still Wins
37:15 &ndash; If You Had $20K&ndash;$100K Today, Here's Exactly What Joe Would Look For in an Online Business&nbsp;
&nbsp;
Key Takeaways
➥ The fastest way to kill your exit? Stop running the business before it's sold. Buyers don't buy potential&mdash;they buy momentum.
➥ Deals close on trust, not spreadsheets. Strong buyer-seller relationships solve problems that contracts can't.
➥ One traffic source is a liability. Diversification is a premium. The more ways a business earns traffic and revenue, the more valuable it becomes.
➥ AI is a powerful assistant&mdash;not your deal advisor. It can speed up due diligence, but it can't replace experience, judgment, or pattern recognition.
➥ Content websites aren't dead. Generic content is. The winners are building brands, authority, and original insights that AI can't replicate.
➥ Creative deal structures create better outcomes. Seller financing, holdbacks, and flexible terms often turn stalled negotiations into closed deals.
➥ Buy the business you're best positioned to grow&mdash;not just the cheapest one you can afford. Your competitive advantage matters more than the asking price.
&nbsp;
About Seph Fontane Pennock
Seph Fontane Pennock is a serial entrepreneur and 8-figure exit founder who built PositivePsychology.com from a personal blog into one of the world's most visited mental health platforms, serving over 19 million users. He grew it to a PE acquisition without spending a dollar on ads, relying purely on SEO-led content strategy. Post-exit, he co-founded the SaaS platform Quenza and has since launched Regenerated.com. Seph is now an active investor and builder.
&nbsp;
Connect with Seph Fontane Pennock
➥ <a href="https://www.linkedin.com/in/seph-fontane-pennock-94666421/">https://www.linkedin.com/in/seph-fontane-pennock-94666421/</a> &nbsp;
➥ <a href="https://psychology.com/">https://psychology.com/</a>&nbsp;&nbsp;
&nbsp;
Resource Links
➥ Connect with Jaryd here -<a href="https://www.linkedin.com/in/jarydkrause"> https://www.linkedin.com/in/jarydkrause</a>
➥ FREE Download the Due Diligence Framework - <a href="https://buyingonlinebusinesses.com/freeresources/">https://buyingonlinebusinesses.com/freeresources/ </a>➥ Buying Online Businesses Website -<a href="https://buyingonlinebusinesses.com/"> https://buyingonlinebusinesses.com</a>
➥ Online Business Due Diligence Services -<a href="https://buyingonlinebusinesses.com/ads-services/"> </a>https://buyingonlinebusinesses.com/duediligence
&nbsp;
Buy &amp; Sell Online Businesses Here (Top Website Brokers We Use) 🔥
➥ Empire Flippers -<a href="https://bit.ly/3RtyMkE"> https://bit.ly/3RtyMkE</a>
➥ Flippa -<a href="https://bit.ly/3wGa8r5"> https://bit.ly/3wGa8r5</a>
➥ Motion Invest -<a href="https://bit.ly/3YmJAmO"> https://bit.ly/3YmJAmO </a>➥ Investors Club -<a href="https://bit.ly/3ZpgioR"> https://bit.ly/3ZpgioR</a>
*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.

Jaryd Krause quit his plumbing job in 2015 by acquiring online businesses and never looked back. Now one of the world's leading Online Business M&A advisors, he's helped thousands of people acquire profitable businesses, made his clients millions, and scaled companies from 6 to 8 figures.

The Buying Online Businesses Podcast cuts through the noise on acquisitions, M&A strategy, and building real wealth through buying already profitable online businesses. Whether you're looking to replace your income or build a portfolio that funds the life you actually want, this is your show!

Jaryd Krause quit his plumbing job in 2015 by acquiring online businesses and never looked back. Now one of the world's leading Online Business M&amp;A advisors, he's helped thousands of people acquire profitable businesses, made his clients millions, and scaled companies from 6 to 8 figures.
The Buying Online Businesses Podcast cuts through the noise on acquisitions, M&amp;A strategy, and building real wealth through buying already profitable online businesses. Whether you're looking to replace your income or build a portfolio that funds the life you actually want, this is your show!

Buying Online Businesses Podcast

Hosted by Jaryd Krause who went from plumber to creating an online business empire through buying websites for passive income. 

This podcast will unfold his secrets as you explore the highs, lows and light bulb moments of his personal journey in each episode. He will show you that no matter where you are in life an alternate lifestyle is more than possible. You will gain the knowledge you need to start buying online businesses yourself and live a fulfilling lifestyle.