Buying or selling a business isn’t just a transaction — it’s a turning point. But too often, what buyers think they want and what sellers believe they deserve don’t line up with reality. The result? Stalled deals, missed opportunities, and plenty of frustration on both sides.

In this episode, Jaryd Krause sits down with Matt Frisca, owner of Transworld Business Advisors of La Grange and Tinley Park, to unpack the biggest reasons deals fail—and what it really takes to make them work. With 20+ business sales closed annually and 50+ active listings, Matt shares real-world insights from both sides of the table.

You’ll learn:
 ✔️ Why sellers struggle to exit cleanly
✔️ Common mistakes buyers make (and how to avoid them)
✔️ The truth about SBA financing and “no money down” deals
✔️ What due diligence really looks like in today’s market

Whether you're buying, selling, or just curious, this episode delivers raw advice and actionable strategies from a dealmaker who knows the game.

🎧 Listen now and get the inside track on what actually moves the needle in business acquisitions.

 





Episode Highlights


12:40 – Importance of motivated sellers and avoiding lead oversaturation

15:45 – The three biggest reasons businesses fail to sell: lack of motivation, messy financials, and unrealistic pricing

19:30 – Recent SBA lending rule changes and fees

22:45 – Why “no money down” deals are unrealistic

24:40 – Risks of inexperienced buyers buying big businesses

28:10 – How to be an attractive, prepared buyer

33:15 – Balancing due diligence and trust to avoid “paralysis by analysis”


 

Key Takeaways

➥ Motivated sellers, clean financials, and realistic prices are crucial.
➥ Content marketing is replacing paid ads due to cost hikes.
➥ Seller equity rollovers now carry higher risk for sellers.
➥ “No money down” deals rarely work; buyers need funds and experience.
➥ Private equity adds competition for deals under $5M.
➥ Prepared buyers with financing and clear plans succeed more.
➥ Avoid overanalyzing—take calculated risks to close deals.

 


About Matt Frisca

Matt Friscia runs and owns the Transworld Business Advisors of La Grange and Tinley Park with his team of 9 agents and one administrative assistant, focusing on main street and lower mid-market business brokerage. 

Their office handles over 20 successful closes a year, and they typically are working 50+ business for sale listings at any given time. Before joining Transworld, Matt worked in media sales for 15 years. Ten of those years were with the Disney company within their ESPN, ABC, and Radio Disney brands. He bought his first business, which was a franchise in the senior care field, back in 2016. He successfully grew that company and ultimately sold it five years later with Transworld Business Advisors.  

His passion is helping small business owners with their business exit transactions while helping to super serve the underserved community of small businesses. Besides having played music professionally for the past 28 years, he enjoys watching his two children play sports, traveling and learning languages.

 

Connect with Matt Frisca

➥ https://www.tworld.com/ 

 

Resource Links

➥ 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/

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

➥ Cloud Ways (Website Hosting) -https://bit.ly/40tjyjG

➥ Link Whisper (SEO tool for internal linking on websites) -https://bit.ly/3l7K7Ld

➥ Convert Kit (Email Software Provider) -https://bit.ly/3o10Xgx

 

🔥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.

Buying or selling a business isn&rsquo;t just a transaction &mdash; it&rsquo;s a turning point. But too often, what buyers think they want and what sellers believe they deserve don&rsquo;t line up with reality. The result? Stalled deals, missed opportunities, and plenty of frustration on both sides.
In this episode, Jaryd Krause sits down with Matt Frisca, owner of Transworld Business Advisors of La Grange and Tinley Park, to unpack the biggest reasons deals fail&mdash;and what it really takes to make them work. With 20+ business sales closed annually and 50+ active listings, Matt shares real-world insights from both sides of the table.
You&rsquo;ll learn: ✔️ Why sellers struggle to exit cleanly ✔️ Common mistakes buyers make (and how to avoid them) ✔️ The truth about SBA financing and &ldquo;no money down&rdquo; deals ✔️ What due diligence really looks like in today&rsquo;s market
Whether you're buying, selling, or just curious, this episode delivers raw advice and actionable strategies from a dealmaker who knows the game.
🎧 Listen now and get the inside track on what actually moves the needle in business acquisitions.
&nbsp;
 
Episode Highlights
 12:40 &ndash; Importance of motivated sellers and avoiding lead oversaturation
15:45 &ndash; The three biggest reasons businesses fail to sell: lack of motivation, messy financials, and unrealistic pricing
19:30 &ndash; Recent SBA lending rule changes and fees
22:45 &ndash; Why &ldquo;no money down&rdquo; deals are unrealistic
24:40 &ndash; Risks of inexperienced buyers buying big businesses
28:10 &ndash; How to be an attractive, prepared buyer
33:15 &ndash; Balancing due diligence and trust to avoid &ldquo;paralysis by analysis&rdquo; 
&nbsp;
Key Takeaways
➥ Motivated sellers, clean financials, and realistic prices are crucial. ➥ Content marketing is replacing paid ads due to cost hikes. ➥ Seller equity rollovers now carry higher risk for sellers. ➥ &ldquo;No money down&rdquo; deals rarely work; buyers need funds and experience. ➥ Private equity adds competition for deals under $5M. ➥ Prepared buyers with financing and clear plans succeed more. ➥ Avoid overanalyzing&mdash;take calculated risks to close deals.
&nbsp;
 About Matt Frisca
Matt Friscia runs and owns the Transworld Business Advisors of La Grange and Tinley Park with his team of 9 agents and one administrative assistant, focusing on main street and lower mid-market business brokerage. Their office handles over 20 successful closes a year, and they typically are working 50+ business for sale listings at any given time. Before joining Transworld, Matt worked in media sales for 15 years. Ten of those years were with the Disney company within their ESPN, ABC, and Radio Disney brands. He bought his first business, which was a franchise in the senior care field, back in 2016. He successfully grew that company and ultimately sold it five years later with Transworld Business Advisors.&nbsp; His passion is helping small business owners with their business exit transactions while helping to super serve the underserved community of small businesses. Besides having played music professionally for the past 28 years, he enjoys watching his two children play sports, traveling and learning languages.
&nbsp;
Connect with&nbsp;Matt Frisca
➥ <a href="https://www.tworld.com/">https://www.tworld.com/</a>&nbsp;
&nbsp;
Resource Links
➥ Buying Online Businesses Website -<a href="https://buyingonlinebusinesses.com/"> https://buyingonlinebusinesses.com</a>
➥ Sell your business to us here -<a href="https://buyingonlinebusinesses.com/sell-your-business/"> https://buyingonlinebusinesses.com/sell-your-business/</a>
➥ Download the Due Diligence Framework -<a href="https://buyingonlinebusinesses.com/freeresources/"> https://buyingonlinebusinesses.com/freeresources/</a>
➥ Google Ads Service -<a href="https://buyingonlinebusinesses.com/ads-services/"> https://buyingonlinebusinesses.com/ads-services/</a>
➥ Connect with Jaryd here -<a href="https://www.linkedin.com/in/jarydkrause"> https://www.linkedin.com/in/jarydkrause</a>
➥ Cloud Ways (Website Hosting) -<a href="https://bit.ly/3HUqW0s"> </a><a href="https://bit.ly/40tjyjG">https://bit.ly/40tjyjG</a>
➥ Link Whisper (SEO tool for internal linking on websites) -<a href="https://bit.ly/3lINGaV"> </a><a href="https://bit.ly/3l7K7Ld">https://bit.ly/3l7K7Ld</a>
➥ Convert Kit (Email Software Provider) -<a href="https://bit.ly/3o10Xgx"> </a><a href="https://bit.ly/3o10Xgx">https://bit.ly/3o10Xgx</a>
&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>
&nbsp;
*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.

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.