One of the most common discussions I have as a franchise coach is about timing—and more specifically, when the timing is right to start a business. And I’ll be honest: I stongly believe two completely opposite things about this topic.
On one hand, I firmly believe that the timing has to be right to become a business owner. On the other hand, I just as strongly believe that the timing is never right.
Yes—those two beliefs directly contradict each other. And yet, both are true. Let me explain.
The Case for “The Timing Has to Be Right”
There are legitimate reasons why the timing simply isn't right to start a business.
In these situations, jumping into business ownership could do more harm than good. It’s not just about excitement or dreams; it’s also about capacity, stability, and attention.
So yes—timing matters.
But here’s the catch…
The Case for “The Timing is Never Right”
Even when your life is relatively stable, there will always be a reason to wait.
These are the more subtle, less obvious timing excuses. And the truth is, if you’re waiting for the perfect moment—you’ll be waiting forever.
The “perfect time” is a myth. Life doesn’t deliver neatly wrapped windows of opportunity. Instead, it gives you messy moments of possibility that require courage to act on.
The Magic Happens in the Middle
So here’s the question: If the timing must be right—but the timing is never right—how does anyone ever start a business?
The answer is simple but profound:
The timing has to be right enough.
It doesn’t have to be perfect. It just has to be possible.
It doesn’t require zero risk. It requires enough readiness and the willingness to move forward despite uncertainty.
Think of it like a Venn diagram:
One circle is Life Readiness—logistics, finances, support.
The sweet spot is the overlap.
It’s the space where things aren’t perfect, but they’re good enough to begin.
So What Does “Right Enough” Look Like?
You have a clear interest in owning a business—and you're not running away from something.
That’s right enough.
It’s not a guarantee of success—but it’s the starting line of a serious
journey.
Final Thought: Readiness is a Decision
Most people who start successful businesses didn’t do it because the timing was perfect.
So if you’re wondering whether the timing is right—ask yourself:
If you're ready enough, that's all you need.
Recently a good friend of mine, Jacki Dezelski, was honored as the recipient of the 2025 Kent C. Schulz Award. As someone who has dedicated her career to improving our community, Jacki is a truly exceptional choice. Jacki is also a top ranked local tennis player and her acceptance speech used tennis as a metaphor providing both guidance and inspiration, as follows... Enjoy
“My Best Tennis Is Still Ahead of Me”
What an honor—truly. And a bit of a role reversal, since I’m usually the one handing out the awards! To join the list of past recipients is deeply meaningful, and also a little surreal.
Let’s talk about Coach Bernie, who always tells me, “Your best tennis is still ahead of you.” That phrase has stuck with me—so much so that I’ve adopted it as a guiding metaphor. For you, it might not be tennis. Maybe it’s your business, your leadership journey, your family, your faith, or your purpose. Whatever your “tennis” is—substitute it right in.
To believe my best tennis is still ahead of me...
…I had to start playing.
That meant picking up the racquet. It required courage, commitment, and saying yes to opportunity—sometimes without knowing where it would lead.
For me, that racquet was a help wanted ad in the Bradenton Heraldback in 1996. That part-time job became a career, a calling, and a community. The Chamber has been my tennis court ever since.
And I’ll always be grateful to the early coaches who believed in me when I was still learning the game.
To keep playing my best tennis...
…I have to show up. Again and again.
That means putting in the work, listening to coaches, and learning from the greats. The best players never stop practicing—and neither can we. That includes adapting our strategies when things change, staying focused in high-pressure moments, and growing from both wins and losses.
Some of the proudest moments of my career have come in the hardest matches:
These weren’t easy rallies. But they shaped me into the player I am today.
To play better tennis…
…I have to challenge myself by stepping onto courts where the players are faster, smarter, stronger.
You don’t grow by playing it safe. You grow by taking the hard shot, reaching the tough ball, adjusting your footwork—and sometimes by losing, learning, and coming back stronger.
That’s how I view leadership. That’s how I view life.
And most importantly… to play my best tennis…
…I have to believe I can.
Belief is the foundation. Without it, there’s no drive to improve, no energy to serve again, no reason to chase the line shot.
So that’s my commitment to you: I believe. I believe my best tennis is still ahead of me. And I believe yours is too—whatever your version of “tennis” may be.
Now let’s get back on the court and play the next match—together.
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Hope you enjoyed Jacki's message as much as I did. Wishing you success!
Back in June, I wrote about the financial milestones of business ownership, and it got me reflecting on the early conversations I have with new entrepreneurs—those exciting first steps when someone decides to pursue business ownership for the very first time.
One of the first exercises I walk people through is a visioning exercise. It's meant to help us get clear on long-term goals. Often, people start with something like:“I want to start a business.”
This kind of thinking is admirable. It’s what we call a BHAG—a Big Hairy Audacious Goal—and I absolutely respect people who are bold enough to aim high. But I also remind them: while it’s important to have a big vision, achieving it happens in steps.
Entrepreneurship Isn’t Genetic
Let’s start with the basics. No one is born with the skills to be a successful entrepreneur. Business ownership isn’t something you're either naturally good at or not. It’s a skill—something learned, practiced, and refined over time.
Even the best franchise in the country can’t guarantee your success. What it can do is give you the tools. But you have to use them. You have to show up, put in the work, make mistakes, and learn as you go.
The Baseball Metaphor
Starting a business is a lot like learning to play baseball. Image stepping up to the plate for the first time. The odds of hitting a home run on your first swing? Pretty slim. Your coach is probably telling you to focus on contacting the ball.
Same goes for your first year in business. Swinging for the fences might feel exciting, but it's often not realistic. Instead, focus on getting on base. A single, or even a stand-up double, is a huge win when you’re just starting out.
Focus on the Fundamentals
Your first year in business is all about learning the fundamentals:
These aren’t glamorous skills, but they’re essential. Mastering them sets the foundation for long-term success.
Over time, you’ll gain experience, confidence, and a better understanding of what you enjoy and what you're good at. Maybe after a few years, you’ll decide to open a second or third business—one that builds on everything you’ve learned and brings you even closer to your big vision.
Grow Step by Step
So, here’s the takeaway: hitting a home run is great, but not always necessary—or even wise—in your first year. Focus on steady progress. Build your skills. Learn the game. And give yourself time.
If you do that, your chances of eventually reaching every goal in your vision—and possibly going even further—go way up.
The dream is real. The path just takes patience, practice, and persistence.
Wishing you success on your entrepreneurial journey!
When I talk to aspiring business owners about their financial goals, many express a desire to replace their current income as quickly as possible. While this might seem like a reasonable objective, it doesn’t truly address the financial milestones necessary for building a successful business. After all, your previous salary was an arbitrary figure set by an employer—it has little relevance to your entrepreneurial journey.
To set yourself up for long-term success, there are three essential financial numbers every business owner must understand:
1. Total Initial Investment
The first critical number is the total cost to launch and operate your business. In the world of franchising, we call this the Item 7 Total Initial Investment—the amount required to open your business and sustain operations. Before taking the leap, you must ensure you can afford this investment and have a clear financial strategy in place.
2. Cash Flow Break-Even Point
The second key financial metric is understanding how long it will take for your business to reach cash flow break-even—the point where your business generates enough revenue to cover its expenses but not yet provide financial benefit to you as the owner. During this period, it’s essential to have a plan to cover your personal living expenses since the business won’t be able to support you just yet.
3. Personal Income Replacement Timeline
The third milestone is determining when your business will generate enough profit to cover your personal living expenses. For example, if you require $5,000 per month ($60,000 annually) to sustain your lifestyle, how long will it take before your business can reliably provide that level of income?
While every entrepreneur dreams of maximizing profits, reaching this third stage means achieving financial freedom—where your business generates enough income to support your lifestyle. At this point, you’re no longer dependent on an employer. Instead, you own an asset that provides financial stability, allowing you to make strategic decisions about future growth rather than operating from a place of financial pressure.
Once your business covers your personal expenses, the next step is achieving time freedom—where your income-producing assets generate wealth without requiring all of your time and energy. This is the ultimate level of entrepreneurial success, but it’s a discussion for another time.
This approach may seem simple, but it’s the exact strategy my wife and I used when we started our business 23 years ago. The goal was never just to replace my salary—it was to achieve financial freedom, and then, eventually, time freedom. Achieving these simple goals give us the ability to live life on our terms.
Wishing you success on your entrepreneurial journey!
When I work with individuals who wish to explore franchising, one of the questions we explore is – ‘What advice would you give to a young person regarding how to live a fulfilling life’. I have received many answers to this question over the years, but Jon L’s response last month was truly exceptional. With Jon’s permission, I am republishing his answer – Enjoy -
Exercise 1.5: My Life's Insights. (The Franchisee Playbook)
During My Life I learned-
I think I would borrow a page from Charlie Munger and tell you that I can't tell you what to do to live a successful and happy life, but I can tell you the things to do to make yourself miserable.
By Jon L.
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After reading that, all I could say was - wow! We spend so much time thinking about what we should do, and so little time thinking about what we should avoid. Thank You Jon.
The question this month is whether you would rather have a baseball team full of home run sluggers or a team that is great at getting on base. Which approach wins more games? Well, the studies are clear. Home runs are fun to watch but if you want to build a successful baseball team, you want a dugout full of players that can reliably get on base. When you are on base, positive things can happen. When you swing for the fence and strike out, you are back on the bench. (Ref: Study)
Let's take the metaphor one step further. Imagine you've never played baseball before. You are up to bat the very first time. What is the chance you're going to hit a home run? Not very good right? Simply getting on base would be considered a success.
Connecting the Dots
Why am I talking about this? Because often I work with first time business owners who are swinging for the fences. When I asked them what their goals and objectives are, they provide a long list including paying off the first house, buying a second house on the beach, buying a boat they can go deep sea fishing with, buying their mother a house, buying their siblings cars, and a variety of other ‘must haves’. I then asked them how they are planning to achieve these goals. Their response normally includes opening a business for $150,000 that can eventually produce millions of dollars a year in revenue. In addition, they want to keep their job while dedicating around 10 hours per week to the business. Has this ever been done. Sure. Is it likely to be a winning strategy? Nope. It is swinging for the fences when the goal should be to just get on base.
Better Approach
The better approach is to focus on getting on base. Your very first business does not have to solve every financial desire you have in life. Quite often it doesn't not. The first business needs to grow to the point where you can cover your living expenses. This delivers freedom. At the same time, the first business needs to teach you all the critical lessons necessary to be an independent business owner. Once this is achieved, then you are on base, and, for a first-time hitter, you can consider that a success.
Just like swinging a bat, being a successful business owner is an acquired skill. Through education and experience, we improve. The goal over time is to grow a variety of income producing assets allowing you to have diversified income and become, as I mentioned in my August E-mail, ‘financially unbreakable’.
Swinging for the fences rarely works out. Focus on reliable, predictable singles and before you know it, you will be standing on home plate.
I don't know about you but I am constantly reading. I am normally reading a few books at the same time and, with the weather being as hot as it is, I've been spending more time than normal in my reading chair. Currently I'm reading a book on Bayes Law, a second book is on Real Estate Syndications, and the third book is The Psychology of Money by Morgan Housel. It's this third book that I'd like to highlight this month.
Over the years one of the things I learned is that saving money isn't that difficult. Saving is all about maintaining a lifestyle that costs less than your earnings. With discipline and time, you will save money. The challenge is making good investment decisions once you have saved money. Chapter five outlines three financial survival characteristics of highly successful individuals. These characteristics apply not only to investing but also to business ownership.
Financially Unbreakable.
The goal is to become financially unbreakable. Most individuals place all their chips on one roll of the dice. All their income comes from one source. All their investments are in one place. If anything happens to either the income source or the investment, they have a serious financial issue. I know you're saying that's not you but how many people reading this newsletter have one job (one source of income) and invest all their money in the stock market (one place). The point of this first item is that being one-dimensional is highly risky. Life happens. The larger your diversity of income sources and the larger the diversity of your investment vehicles, the more unbreakable you will be.
You Plan, God Laughs.
The second point relates to planning. ‘Planning is important, but the most important part of every plan is to plan on the plan not going according to plan.' Remember Mike Tyson quote, ‘Everyone has a plan until they get punched in the face.’ Well, things never go according to plan. For a plan to be useful, it must be able to survive the vagaries of reality. In other words, it must have a significant ‘margin of safety’. Margin of safety is different from being conservative. Conservative is avoiding risk. Margin of safety is raising the odds of success at a given level of risk by increasing your chances of survival. The magic is that the higher your margin of safety, the greater your chance for a favorable outcome. Margin of Safety drives risk reduction.
Barbelled Personality
A ‘barbelled personality’ is a personality that is both optimistic about the future but also paranoid about what can go wrong. Successful individuals believe the future is bright and that everything is moving upwards and to the right, while also understanding lots of things will go wrong and you need to be vigilant, prepared and even paranoid. Individuals who are solely optimistic tend to take foolhardy risks leading to loss. Individuals who are solely paranoid believe that everyone is out to get them and never take any risks. Neither path works. The only path to success is both optimism and paranoia.
Hopefully these three thoughts give you a little something to chew on as you sit out by the pool trying to stay cool this summer. Wishing you and yours the very best.
First, an most importantly, Happy 4th of July!. I hope you have time set aside with family and friends. Enjoy and stay safe.
At it's core, the 4th of July is about freedom and self-determination. It is about the willingness to bet on ourselves. Over a decade ago I published a blog summarizing a talk by Tom Shay. Today, his message is even more relevant so I am republishing this poignant essay.
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Last week I had the distinct honor to hear Tom Shay, CEO of Right Management, Florida/Caribbean speak on the topic of job transition and career management. What an interesting discussion. Mr. Shay has held this position for 31 years and during his tenure Mr. Shay has seen exceptional change in the employer/employee relationship.
Mr. Shay began by sharing a very simple statistic. During his father’s generation (presumably 40 years ago), the average tenure for a manager or higher, was 27 years. Losing a job was considered taboo. As a matter of fact, it was hard to lose a job. You really had to do something wrong. Today the average tenure for that same employee is 3.7 years (update - 3.1 years in 2022). Doing a good job does not mean you will keep your job. Job transition is commonplace and expected. Does that surprise you? From 27 years to an average of 3.7 (3.1)years. Wow.
Mr Shay went on to state that what used to be ‘one job for life’ has disappeared. Today it is one boss for life – yourself. You need to look at yourself as a company and intelligently apply your personal brand to the marketplace. Mr. Shay’s point is that we are all ‘free agents’ or ‘businesses’. Companies may contract with you if they think you can solve their problem. Once the problem is fixed, you will need to find another application for your skills.
Finally, Mr. Shay spoke about the important of investing in yourself. Going to conferences, staying current and learning new things is what allows us to remain relevant. Don’t expect someone else to pay for you to improve yourself. We are all ‘free agents’ or ‘businesses’ and as such, we need to focus on doing those things that allow us to best achieve our personal goals
As you know, I spend most of my time discussing business ownership, but Mr. Shay’s points are well stated. The world is a different place. Business ownership may or may not be the right path for you but regardless, you need to think of yourself as a business.
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This message from Tom Shay goes to the heart of what freedom and self-determination is all about. A great message for each and everyone one of us on this 4th of July holiday.
Eleven months ago I announced that I personally invested in another franchise. Since that time I've received many inquiries asking - How it's going? Are you open? Can you share an update?
Well, I'm proud to announce that we are officially open for business. Our ‘official’ grand opening was last Wednesday, and we were blessed to have a large turnout of community leaders in attendance to support our new business. Key employees are in place we are already beginning to service our community. Obviously, one month does not create a trend but we are confident that everything is moving in the right direction.
As I always share with folks, the first location almost always takes longer, and costs more than you expect. Our experience was no exception with signing-to-opening taking almost 12 months. However, when we look at our anticipated cash flow for the first month, we are on track while rapidly acquiring new clients.
As we look toward the future, I fully expect to get the second location open faster with greater capital efficiency. There is a learning curve that we all go through when opening a new business. My partners and I feel confident that we're on the right track to not only fulfill our three-unit agreement, but to potentially grow beyond that. However, let's not get ahead of ourselves. At this point we are simply keeping our head down and focusing on day-to-day activities to exceed client expectations.
A few years ago I subscribed to a free email newsletter called The Morning Brew.
Often, I try new email subscriptions and quickly tire of them; however, The Morning Brew has become a standard part of my morning. The email newsletter covers all the top issues of the day with brevity and cutting humor, which I enjoy.
The Morning Brew is sent once a day and the January 19th Morning Brew really struck a chord with me. The first article was entitled, The Pandemic’s Entrepreneurial Boom Isn't Over Yet. The article stated that more than 5,000,000 new business applications were filed in 2022, according to the latest data from the US Census Bureau. This equates to about 13,500 new business applications filed every day last year. I quote ‘Whether this represents a testament to the country's entrepreneurial spirit, and indictment of 9-to-5s, or simply a case of everyone seeing the same Tiktok about tax benefits of forming an LLC, it's a sign that the pandemic era startup boom may be here to stay.’
A couple of sections down in the same newsletter they moved on to news from the Tech world. Again, I quote, ‘Microsoft announced plans to cut 10,000 employees yesterday, and Amazon began a round of layoffs that will impact 18,000 people. These are just the latest layoffs of tech companies, many of which have begun thinning their ranks’.
Anecdotally, we know that interest in business ownership and entrepreneurship has increased dramatically over the last number of years; however, the data supplied in the January 19th Morning Brew really brings together the factual data underlying many of the trends we're seeing. It's rare in one newsletter to see so many clear indicators regarding where the large companies are going and how individuals are responding to the increased risk of employment.
(If you want to have a laugh in the morning while keeping up with the current news, give The Morning Brew a try for a week or two. Who knows, it might become a part of your morning too.)
Wishing you an amazing February.
