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Before You Invest, Ask “Who Actually Wants This?”

Episode XXX
October 21, 2026

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Hosted By

Dan Sullivan, Co-Founder of Strategic Coach® Dan Sullivan
Jeffrey Madoff Jeffrey Madoff

How do you tell a real opportunity from an expensive distraction? Dan Sullivan and Jeffrey Madoff explore why big ideas like Segway and Quibi fell short despite big-name backers and huge budgets, and explain how to look past the hype, ask better questions, and focus on what your customers actually want.

 

Show Notes:

 

Even in a good year, only a small share of IPOs turn out to be good investments.

 

Some investors aren’t betting that an idea will work—they’re betting they can get out before everyone else realizes it won’t.

 

Sometimes, the promise of what a product could do is easier to sell than something that already works.

 

Quibi had big names and plenty of money behind it, but it was solving a problem people didn’t have.

 

If you’re doing something new, there may not be credentials for it yet, but customers who keep paying you are a good sign.

 

The entertainment business is all guesses and bets, and past success doesn’t guarantee the next hit.

 

For every invention that takes off, there are plenty that don’t.

 

Sometimes, people try to sell you on who else has invested rather than on the idea itself.

 

A great demo gets people excited, but a lasting business needs customers who keep coming back.

 

Before you put your money in, ask who gets paid even if the idea doesn’t work.

 

Resources:

 

Most companies hire to fill jobs. The best leaders cast to build greatness. Casting Not Hiring offers a new way to build a team that performs together rather than a collection of people who simply function on their own. Order Casting Not Hiring now. 

 

Learn more about Jeffrey Madoff

 

Dan Sullivan and Strategic Coach®

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