Latest Updates

Monday, August 11, 2025

When to Sell Your Business--Before It's Too Late

Posted By: George Deeb - 8/11/2025

As a founding entrepreneur, it is hard not to always be "in love" with "your baby". You created something from nothing, ...


As a founding entrepreneur, it is hard not to always be "in love" with "your baby". You created something from nothing, you nurtured it along the way, and you built something really great. Until the point "your baby" stops growing, your profitability falls with increased competition, and the roller coaster starts picking up speed in the wrong direction, with revenues going down, not up as before.  It is very easy to want to "stay the course" and hope for things to get better in the future. Depending on the root cause of the fall, like a temporary decline in the economy, it very well could rebound. But, there are times when the root cause cannot be fixed, or worse yet, will continue to "snowball" in the wrong direction.  In those scenarios, you need to know when to pull the "ripcord" to save whatever value you have left before your business is worth zero. This post will help you identify what to look for and how to get you and your shareholders a "soft landing" when things start to turn south.

Read the rest of this post in Entrepreneur, which I guest authored this week.

For future posts, please follow me on Twitter at: @georgedeeb.



[VIDEO] The Four Pillars of Equity Distribution For Startups

Posted By: George Deeb - 8/11/2025

I was recently interviewed by  ASBN , an online "television network" serving the small business community, about how best to split...


I was recently interviewed by ASBN, an online "television network" serving the small business community, about how best to split-up the equity between cofounders of a startup.  This video will help you learn how to handle all the key drivers here, like if the cofounder is investing cash, if they are deferring salary, their role in the company and more.  I thought this video turned out great, and I wanted to share it with all of you to make sure all cofounders are being treated fairly upfront, so there are no debates about equity interests in the future. I hope you like it!!



The embedded video player didn't give me the option to change the size of this video.  But, if you want to see a bigger version, simply click the expand size button in the player above.

Thanks again to Jim Fitzpatrick, Shyann Malone and the ASBN team for having me on the show.  I look forward to our next interview together.


For future posts, please follow me on Twitter at: @georgedeeb.


Wednesday, July 30, 2025

Lesson #374: The Top 5 Reasons Why People Buy a Business

Posted By: George Deeb - 7/30/2025

  Many entrepreneurs go down the path of buying a business to help jump start their business building efforts.  But oftentimes, they don’t g...


 

Many entrepreneurs go down the path of buying a business to help jump start their business building efforts.  But oftentimes, they don’t give enough thought to WHY they are buying the business, and their long term goals they are hoping to accomplish from this investment.  Unless they are 100% clear on the “end game”, they could get themselves into a situation that is not what they intended, and it could be too late to fix it once they close on the purchase.  This post will help you assess your acquisition goals before you get started hunting for targets, so you don’t repeat the mistakes that many other entrepreneurs have made by not doing sufficient homework upfront.

Let’s talk through the various reasons why people buy companies:

1.  You Need a High Return on Investment

Like any other investment, you want it to be worth as much as possible at the time you are ready to sell it.  This path most typically involves buying a business at a low price, increasing its value over the next 5-10 years through increased sales and marketing efforts or other margin enhancement techniques, and then selling it for a much higher value down the road.  And that higher value typically comes from two sources:  the higher profits of the bigger business and the higher sale multiple of earnings, as bigger companies are typically sold at higher sale multiples than smaller companies.  But the intent here is to buy and sell the business—that is the intent from day one.  And it may or may not require you raising outside capital to assist you with the purchase or your scaling efforts.  If all goes well, you sell the business at 5x-10x the price you purchased it, and that is when you get your “big payday” as a shareholder.

2.  You Need Current Recurring Cashflow  

In this category, it is less about growing a business, and more about “milking it” for recurring cash flow from whatever size the business is today.  Here it is less about shooting for the highest long-term ROI possible, and more about driving the highest near-term annual return on invested capital.  These investments can be things like buying a car wash, a strip mall to rent, or a restaurant franchise where you are hoping to drive 10-20% annual returns on your investment.  This is basically a more hands-on alternative to investing in the stock market or other more traditional investment vehicles.  It may or may not require an investor partner, like a family office, that is also looking for current recurring cashflow.  This path is preferred if you need current cash and are not planning to reinvest annual profits into the future growth of the business, as you were doing in the first category.

3.  You Are Creating a Family Legacy

In this category, there is simply one goal: owning and operating a family run business that you can hand off to future generations.  It could come in the form of either of the first two categories above, with one primary difference:  you would not want to take any outside investors, as they will require an exit strategy down the road, and may require you to sell the company to achieve that goal, which defeats of the whole purpose of ending up with a business you can hand off to your family members.  The other major difference here is now there may be multiple opinions around the family dinner table in terms of what types of business they would enjoy operating.  So be sure to toss around those mutually acceptable ideas as a group, before you get started, so there are high odds the next generation will enjoy working in the business and will want to take it over when the older generation retires.

4.   You Need Passive Income   

Another type of business you can buy is one that comes with very little work required by buyers in terms of operating the company.  Businesses that basically “run themselves”.  This could be things like buying a parking garage, or a business that places vending machines in retail locations, or a business that comes with a general manager that will be doing the majority of the work.  So, as you are assessing which business to buy, figure out how much time you want to personally be investing in it, as there is a wide range from 5 hours a week to 50+ hours a week, depending on which business you end up buying.

5.  You Simply Need a Job

This last category is one of necessity. Sometimes people have a hard time getting hired into a job and they need a salary with which to live.   Oftentimes their solution to that is buying a company that is large enough to afford them a salary or other annual distributions that can cover the costs of lliving.  It may or may not involve having investor partners, depending on the size of the company.  But if you take on investors, just remember, you may be looking for another business to buy in 5-10 years, after your investors require you to sell the business to enable their exit down the road. If you don’t want that risk, don’t take on new investors.

Closing Thoughts

So, as we have discussed, there are many different reasons for buying a business. Make sure you are 100% clear on the reasons you are buying a business, and incorporate the learnings above during your evaluation process, to prevent you from getting into a situation that you did not fully understand the consequences when you started.  Good luck and happy hunting!


For future posts, please follow me on Twitter at: @georgedeeb.




Monday, July 14, 2025

Why Sharing the CEO Title Usually Doesn't Work

Posted By: George Deeb - 7/14/2025

  Oftentimes, two co-founders think it is a good idea to share CEO responsibilities as co-CEOs. The logic is that they can separate their ro...

 


Oftentimes, two co-founders think it is a good idea to share CEO responsibilities as co-CEOs. The logic is that they can separate their roles and responsibilities, with one person leading certain departments (e.g., sales and marketing) and the other person leading other departments (e.g., technology and operations). The reality is, this is a pretty bad idea.  The business should only have one leader at a time who can "lead the ship" and make sure everything is perfectly coordinated across the entire company. This article will teach you the potential pitfalls of a co-CEO strategy.

Read the rest of this post in Entrepreneur, which I guest authored this week.

For future posts, please follow me on Twitter at: @georgedeeb.



Friday, June 27, 2025

Lesson #373: When to Fire Yourself as CEO?

Posted By: George Deeb - 6/27/2025

  Most CEOs don’t usually think about putting themselves up on the firing block, but there any many instances where you as the CEO of the bu...

 


Most CEOs don’t usually think about putting themselves up on the firing block, but there any many instances where you as the CEO of the business may be holding your business back.  You need to be honest in your assessment of yourself as CEO, to make sure you are in fact the right person for the job.  This post will help you identify certain scenarios where a CEO change may be necessary, even if it means you firing yourself from the job.

You No Longer Have the Right Skillsets

Most entrepreneurs are very good at taking a “piece of paper” idea, productizing it, taking it to market and getting initial traction for the business up to the first $10MM in revenues of the company’s growth curve.  That is not an easy feat, and you should be very proud of that accomplishment.  But as the company then needs to scale from $10MM to $50MM in revenues for the next phase of its growth, that typically requires a very different skillset.  Now you are talking about launching new products, new markets, international expansion, mergers and acquisitions, and other techniques that may be unfamiliar to you.

If you suddenly find yourself drowning with the new challenges of your later-stage growth, it may be the right time to find your replacement that already has those proven skills.  And you shouldn’t feel embarrassed about admitting this—you should feel empowered that you were actually smart enough to assess the situation and how best to resolve it.  You still have your equity ownership, and wouldn’t you want your stock price growth to have the highest chance for success as a shareholder?  Sometimes, that could be in the hands of somebody other than yourself.

You Have Run Out of Ideas

If your business is struggling and you have tried everything you possibly could to “right the ship”, it may simply be a function of “you don’t know, what you don’t know”.  You are only as smart as your own education and experience has made you.  But sometimes a “fresh set of eyes” is exactly what the business needs to turn it around.  That new CEO may see some easy fix, based on their past education and experiences, that was simply in your blind spot.  So, if you often find yourself scratching your head without the right answers to your business’s challenges, maybe it is time for a new CEO.

You No Longer Have the Passion For the Business

An equally important part of being successful as a CEO is having the right “fire in your belly” to succeed at all costs, no matter what challenges get thrown your way.  If you find yourself losing that passion or getting bored with the business (which can easily happen the longer you are there), it is very easy to lose focus and basically “go through the motions”, with the business “coasting” based on historical efforts and not “accelerating” with new ideas and efforts.  You are not doing your shareholders (including yourself) any favors by sticking around in this scenario.  Be smart enough to know when you have “mentally checked out” and find your replacement that is as excited about your business and its potential, as you were when you first started.

You Are Not Getting Along With Your Team

Being a successful CEO requires building a great team that is gelling well with each other.  Just like in any marriage, sometimes relationships can sour over time.  Maybe it is your fault, and you are ruffling everyone’s feathers.  Maybe its your colleagues fault, and every word out of their mouth drives you crazy.  Whatever the situation is, a business won’t thrive if the team cannot get along with each other.  Either they need to go, or you need to go, to find team members that will actually respect each other and enjoy each other’s company when “slogging through the mud” together.

You Have Lost the Confidence of Your Colleagues

Maybe you feel you are doing a good job as CEO, but if your fellow employees, partners or investors don’t think you are doing a good job.  In this scenario, maybe it is time for you to go.  This can be a really bitter pill to swallow.  You look in the mirror and see success, and your colleagues look at you and see short fallings.  But if the team has lost confidence in you, it is time to show yourself to the exit, as the team will not follow a leader that they do not think is leading them in the right direction.  And it could be better for you to step down on your own terms, than wait to get fired by your board when they have seen enough (which will be a lot harder to explain to your new employers).

Closing Thoughts

Hopefully, this post helped you complete your own self-evaluation in your role as CEO.  After reading this post, do you still think you are the right person for the job?  If so, great, it’s full steam ahead.  But if anything in this post resonated with you as “striking a chord”, it may be time to have that very difficult conversation with yourself.  Your business, team and shareholders (including yourself) will thank you!!


For future posts, follow me on Twitter at: @georgedeeb.




Thursday, June 12, 2025

5 Good Reasons Why People Buy a Business

Posted By: George Deeb - 6/12/2025

Many entrepreneurs go down the path of buying a business to help jump-start their business-building efforts. But oftentimes, they don't ...


Many entrepreneurs go down the path of buying a business to help jump-start their business-building efforts. But oftentimes, they don't give enough thought to "why" they are buying the business, and the long-term goals they are hoping to accomplish from this investment. Unless they are 100% clear on the "end game", they could get themselves into a situation that is not what they intended, and it could be too late to fix it once they close on the purchase. These five reasons will help you assess your acquisition goals before you get started hunting for targets, so you don't repeat the mistakes that many other entrepreneurs have made by not doing sufficient homework upfront.

Read the rest of this post in Entrepreneur, which I guest authored this week.

For future posts, please follow me on Twitter at: @georgedeeb.



Strategy

General Business

Marketing

Sales

Fund Raising

Red Rocket is a featured contributor on entrepreneurship for many trusted business sites:

Copyright 2011- Red Rocket Partners, LLC