Mark A. Winsor
333 W. Vine Street
Suite 300 Office 31
Lexington, KY 40507
Consider two scenarios…
Imagine you’re walking around your house when, suddenly, a 135-pound weight appears across your shoulders.
It came from out of nowhere. You stagger. Every muscle in your body fires in a desperate struggle to keep you upright. Your mind goes blank. Your heart races.
It’s an intense, potentially dangerous situation that you had no control over. It’s terrifying.
But now imagine you’re in a gym. You’ve been working out consistently for months, and it’s time to test your limits.
You place 135 pounds on your shoulders. You squat down, then start pushing. Every muscle fires. Your mind goes blank. Your heart races.
It’s an intense, potentially dangerous situation. But it’s thrilling. You celebrate when you’re done.
Both scenarios are almost identical, with one critical difference.
In the first scenario, you didn’t choose the challenge. In the second scenario, you did.
That’s the difference between terror and triumph.
So if you want to be an entrepreneur, make a habit of facing challenges head-on, rather than waiting for problems to drop in your lap. See if you start having more triumphant days than terrifying ones.
Successful businesses begin with answers to questions like…
What are the startup costs and can you afford them?
Have you found a proven system to follow that creates predictable results?
Will you create your own market assets or outsource to others?
What technology will you need? Is it already in place or will you have to assemble it?
Are you prepared for having too few—or too many—customers?
These are the questions you need to answer before you can transform your idea into a business. If your answers are less than satisfactory, then it’s time to go back to the drawing board.
Why? Because you may find yourself with a business, but no customers. That’s because you have an idea, but not a solution. And people will pay you for solutions, not ideas.
You may discover that your idea is good, but needs refinement.
Or you may discover that you need a new idea!
Either way, it’s better to vet your ideas fully at the start than realize you’ve built an entire business on an unstable foundation.
So take your idea, and put it through the ringer. If it’s good, it will survive. If not, you’ll have saved yourself a serious headache, a lot of time, and possibly a significant amount of money.
Yes, logic steers the business—entrepreneurship requires a full embrace of data, metrics, and brutal honesty.
But raw reasoning doesn’t sustain you through seasons of hardship and doubt. Far from it—the numbers may actually lead you to quit prematurely.
Think about what’s sustained you through your most difficult challenges. Was it a spreadsheet full of formulas predicting your odds of success? Or was it clinging to the things that matter?
That’s what creates uncommon success—emotion based tenacity to hold on, comeback, and win, regardless of the odds.
And note this well—starting a business that doesn’t inspire you, one without a mission or vision, simply won’t generate that emotion.
What inspires you? What do you want to change? What’s a skill that gets you in the zone? Those are all signposts pointing you towards a business that you can sustain through whatever life throws your way.
Why? Because of the very nature of entrepreneurship.
Here’s how it works…
Entrepreneurs solve problems for consumers or businesses. The greater the problem, the greater the potential reward.
Recessions present massive problems to everyone—unemployment, restricted cash flow, businesses shutting down, and an atmosphere of tension and dread, to name just a few.
Step up to the plate and solve those problems, and you stand to reap significant benefits.
But having more problems to solve isn’t your only advantage.
Afraid of a saturated market? Recessions can thin out competitors and free up market niches.
Intimidated by startup costs? Recessions can lower the price tag on the goods and services you need to get your business into gear.
Unsure about going it alone? Recessions can increase the availability of talent looking for new, fresh opportunities.
So if a faltering economy has you skittish about starting a business, it may be wise to reconsider. Research the market you seek to enter, speak with a seasoned entrepreneur, and start taking steps towards starting a part-time business. You might find that the downturn is the start of your next opportunity.
For many, employer benefits are non-negotiable. They help mitigate the costs of healthcare—which can be extreme—and can offer extra firepower for building wealth with 401(k) contribution matching.
You lose those direct benefits when you quit your day job to make the move to full-time entrepreneurship. So sacrificing them rashly could set your finances—and future—up for disaster.
Fortunately, a catastrophe is easy to sidestep. But how?
If you don’t have the resources to fully replace your benefits, don’t make the commitment to full-time entrepreneurship.
Instead, keep your full-time job and work your business part-time.
You keep your benefits, and you learn the ropes of entrepreneurship. Once it’s clear that your business has the potential to replace your 9-to-5 income, you can transition to full-time entrepreneurship with more confidence. It’s a win-win strategy.
The downside? You may find yourself strapped for time and energy during the transition.
But it may be a small price to pay for what you get—the opportunity to start a business without sacrificing your stability.
That’s because you’re making a trade with your boss.
You give your time and effort. They give you a paycheck.
They help you pay your bills. You help them build their business.
Make no mistake—paying your bills is a good thing.
But building a business is better.
Why? Because freedom, true freedom to build something, requires both the time to do what you want, and the money to make it happen.
A paycheck gives you little of either.
A business gives you limitless potential for both.
When you’re an employee, you work for someone else’s time, earning their money, building their dream.
When you’re an entrepreneur, you work on your own time, scaling your own income, and creating your own freedom.
If being an entrepreneur sounds better, that’s because it can be… IF you can find the right system AND leadership.
Together, they can help you mitigate risk and spare you the wasted time and mounting stress of trying to build a business from scratch.
So if you’re ready to make the move from employee to entrepreneur, let’s talk. We can explore what it would look like for you to start a business that can help create the time and money you need to achieve the freedom you desire.
They fail when they try to go it alone.
And it’s no wonder why. Unless you’re a hermit, you need other people.
You need encouragement.
You need mentorship.
You need camaraderie.
And that’s normal—it’s what it means to be human.
But entrepreneurs? Too often, they go it alone.
It’s no wonder why. Make the leap from employee to entrepreneur, and you may find yourself alone on the other side.
Everyone else is working their 9-to-5s, while you’re spending 16 hours each day making your dream a reality. Unless you find a community of collaborators, it’s a lonely existence.
Loneliness makes it far more difficult to jump-start a successful business. It literally kills.¹
I believe that entrepreneurs succeed when they work together. The e2E model leverages teamwork and experienced mentorship so anyone can start a business with greater support and less risk.
It’s the least I can do—my journey to entrepreneurship was marked by constant support and encouragement by fellow entrepreneurs.
So if you’re considering entrepreneurship but are afraid to make the move, let’s chat. We can explore the support systems available to you if you fire up your own business.
¹ “Loneliness and Social Isolation Linked to Serious Health Conditions,” CDC, Apr 29, 2021, https://www.cdc.gov/aging/publications/features/lonely-older-adults.html
In fact, most people want ownership of something. They want to look at a home, a family, a business, a life, and say “I did that. I built that.”
And that means they want stakes. They want the potential to fail, and to win anyway.
But what do most people get? Cog-in-the-machine jobs they don’t care about. Counting the hours until the day ends. Feeling like they’re not making much of a difference—for themselves or others.
In other words, no stakes. Who would want ownership of that?
Yes, starting a business is hard. Even with support, pre-built processes, and mentorship, entrepreneurship will stretch you. There will be many times where your decisions actually matter.
Choose wrong, pay the price. Choose right, reap the rewards.
And that’s the whole point. Because ownership unlocks a whole new dimension of life. You discover what you’re made of. You’re confronted by your weaknesses. You’re amazed by your strengths.
You find out that you’re far stronger than you ever realized.
So if you’re thinking about entrepreneurship, make the move. Own your own business. Own your own decisions. Own your own failures and successes. Own your own life.
There’s a stereotype that all successful entrepreneurs have borderline mythic powers of focus.
They wear the same t-shirt days on end to free up their bandwidth for big decisions.
They hone their mental acuity by reading dozens of big books per year.
They can move boulders with their minds and shoot lightning from their fingers…
You get the picture.
But you don’t have to be a Jedi Knight—or Sith Lord—to become a successful entrepreneur.
You just have to really love what you do.
Studies have shown that people with strong willpower actually enjoy the hard things they do.¹ The maniac who’s out running at 5:00 AM? He’s not necessarily a self-loathing monk—he might be having a blast.
The same is true of entrepreneurs. The fuel for their focus, their refusal to quit, and their seemingly limitless resourcefulness is that they’re having fun.
The takeaway? If you’re going to start a business, choose an industry and mission you love. It’s the best way to fortify your will against the challenges you face… and maybe have some fun while you’re at it.
¹ “Why willpower is overrated,” Brian Resnick, Vox, Jan 2, 2020, https://www.vox.com/science-and-health/2018/1/15/16863374/willpower-overrated-self-control-psychology
Here’s a thought that will make your heart race: Quitting your job to start a business. It’s the ultimate step away from security and routine to uncertainty and chaos. But it’s a step many think is necessary to become an entrepreneur.
But it’s not. For many, it might even be a mistake.
That’s because it may be too intense for first-time entrepreneurs. Without support and, above all, experience, diving into full time entrepreneurship can be the short road to burnout.
That’s why it’s often best to explore entrepreneurship in your spare time. It gives you the freedom to start slow and steady, making strategic steps to build momentum. If your spare time experiment falls through, no sweat! You don’t necessarily need it to make ends meet.
That freedom also can give you the boldness you need to create innovative—and possibly risky—solutions.
Put to rest the myth that you need to dive into entrepreneurship full time. Start small. Start strategic. Start building. It will serve you far better than making a rash decision before you’re prepared for making a full time commitment.
It often comes with a pay raise, which is always good. It can represent a boost in responsibility, pushing your career forward.
But here’s a question few have asked—is a promotion the best way to boost your income?
Let’s do the math.
The average income boost from a raise is 3%.¹ If you earn $60,000 per year, then you can expect a raise to give you an annual boost of $1,800. That’s $150 per month.
Depending on your situation, that could make a huge difference for your financial picture. But it pales in comparison to other income-boosting strategies. For instance, changing jobs can boost your salary by 14.8%.² The average annual income boost from starting a business is $14,705.³
Suddenly, 3% doesn’t seem all that impressive!
Again, this isn’t to detract from getting a promotion. It’s a testament to your work ethic and grit.
But if your entire career arc hinges on landing one promotion after another, you may need a better strategy.
¹ “What to Expect from an Average Promotion Raise,” Indeed.com, Feb 22, 2021, https://www.indeed.com/career-advice/pay-salary/average-promotion-raise
² “Average Salary Increase When Changing Jobs Statistics ,” Chris Kolmar, Zippia, Dec 28, 2021, https://www.zippia.com/advice/average-salary-increase-when-changing-jobs/
³ “STUDY: Millions of Americans have a ‘side hustle’ to boost their incomes and pursue their passions,” Vista Newsroom, Aug 1, 2019, https://news.vistaprint.com/side-hustle-study-us
It’s because the right kind of business can provide income that scales with inflation. Here’s how it works…
Inflation is the steady rise of prices over time. The only way for a salaried employee to keep up with those price increases is for their paychecks to grow at the same rate, which may not always happen.
Entrepreneurs have an option—they can increase prices. As the cost of living increases, so does the revenue from their business.
Here’s the catch—it only works if you’re selling a solution that’s in demand. Otherwise, customers may decide that they really don’t need your services after all and stop buying.
So if you’re looking to inflation-proof your income, a business may be just what you need. But make no mistake—the industry and mentorship you choose to start that business will mean the difference between inflation-proof, and inflation-vulnerable.
“Warren Buffett says these businesses do the best during periods of high inflation,” Nicolas Vega, CNBC, Aug 19 2021, https://www.cnbc.com/2021/08/19/warren-buffett-inflation-best-businesses.html
But we all know entrepreneurs wear many, many hats. At times, they’ll juggle acting as CEO, the marketing department, sales, support, HR, and accounting. Even thinking about that level of multitasking makes many peoples’ brains shut off!
But the science is clear—multitasking doesn’t work. Hopping back and forth from task to task takes a massive toll on your brain’s efficiency. One study showed it lowers IQ 15 points, putting most people in the intelligence range of the average 8 year old.¹
Trying to successfully multitask is one of the greatest barriers to becoming an entrepreneur.
So entrepreneurs, being the problem solvers they are, have developed a simple solution—don’t multitask. Period.
Instead, they’ve learned two workarounds…
Leveraging flow. That means turning off the phone, going on do-not-disturb mode, and giving their entire attention to the task at hand. They work on one priority at a time for a sustained period to maximize their focus and efficiency. Then, they move on to the next task.
Delegating the small stuff. Remember, the super power of entrepreneurs is their team. Once they can hire employees, this frees up their time to focus on the important tasks that require their full attention.
So if you’re afraid of starting a business because you don’t think you can handle all the multitasking, don’t be. Just remember to focus on one task at a time, and delegate the rest.
¹ “To Multitask or Not to Multitask,” USC Dornsife
Seems counterintuitive, right? Business owners can work long hours, face complex problems, and carry a heavy load of stress—with no guarantee of success.
At least, that’s what you get told. And it couldn’t be more wrong.
Two new studies reveal the truth.
The first, from Baylor University, found that entrepreneurs are subjectively happier.¹ In other words, they feel better. Why? Because they…
• Have a greater sense of autonomy
• Feel a closer connection to their purpose
• Apply their skills and passions to their work
The second study, from the University of Pennsylvania in 2012, showed that entrepreneurs are far happier than employees.² Even the high number of unsuccessful entrepreneurs didn’t change the results. Entrepreneurs, regardless of income, were happier than even highly paid corporate officers.
And it wasn’t just the entrepreneurs. The study from Baylor proved that the presence of small businesses improved the health of surrounding communities.³ The more entrepreneurs, the greater the health of the neighborhood.
Start a business. It doesn’t have to be a stressful, high-stakes tech startup. Just an outlet for your skills that also pays you.
¹ “The Good Business of Thriving Entrepreneurs,” Justin Walker, Baylor University Hankamer School of Business, Mar 30, 2020, https://www.baylor.edu/business/news/news.php?action=story&story=218228
² “Rich or Not, Entrepreneurs Are Happiest in Study,” Elizabeth Blackwell, TheStreet, Sep 28, 2012, https://www.thestreet.com/investing/rich-or-not-entrepreneurs-are-happiest-in-study-11721398
³ “Entrepreneurs Are Happier And Healthier Than Employees According To University Research Studies,” Bernhard Schroeder, Forbes, Apr 1, 2022, https://www.forbes.com/sites/bernhardschroeder/2022/04/01/entrepreneurs-are-happier-and-healthier-than-employees-according-to-university-research-studies/?sh=340a1cc73ee6
Hint—it’s not what you tell yourself.
What you tell yourself are excuses. They pop into your brain as thoughts, like…
“I just don’t have time.”
“Maybe in a few months.”
“Well, first I’ll have to make a business plan, and then I’ll need to find clients and then…”
Those thoughts are coming from somewhere. They come from your emotions. And emotions can be irrational… and very, very powerful.
Emotions cause the sense of overwhelm when you think about the long, hard, lonely hours.
They cause the hazy uncertainty of ditching your stable and comforting routines.
They cause that churning in your gut when you realize you could fail.
Emotions are stopping you from entrepreneurship. The reasons may come and go. But the feelings stay the same.
So what are the feelings that come up when you think about starting a business? Are they moving you towards a destiny that excites you? Or are they moving you away from pursuing your potential?
Your partners, mentors, and collaborators will impact every way you’ll be measured as an entrepreneur. What your success will look like. What your income will look like.
As the great Jim Rohn said, “You are the average of the five people you spend the most time with.”
Think about those five people in your life. Do you want to be the average of them?
If your answer is anything less than an enthusiastic yes, it’s time to do some soul searching. To be a successful entrepreneur, it may be time to make some hard decisions about who you spend the bulk of your time with.
Maybe you need to limit your time with energy vampires. Maybe you need to stop sharing your hopes and dreams with negative people. Maybe you need to completely cut toxic influences out of your life…
You may think it’s cruel to tell someone in no uncertain terms, “Sorry. I’m not going to spend my energy on this anymore.” You’re afraid they’ll feel like they’ve been abandoned.
But you don’t owe them anything. They’re the toxic people who brought negativity into your life. If they can’t deal with your building something great, that’s kinda their problem.
In other words, it’s time to set boundaries for yourself. It’s time to say what behavior you’ll tolerate and what behavior you won’t. It’s time to show yourself some respect like never before.
They thrive on flexibility. They need space to be creative. They have to be unrestrained to dream.
Surveys have revealed that 55% of entrepreneurs started a business to become their own boss, while 39% said they wanted to pursue their passion.¹
Why? Because it’s how they’re hardwired. Research has shown that entrepreneurs are higher in both openness to experience and conscientiousness than managers.² In other words, they’re very creative and highly driven.
And those are terrible things to be in many offices. Think about it. The average employment position is not designed to offer freedom—it’s designed to pay you a defined amount of money for a defined job.
Employees often have no creative control over their work. They can feel like a stop on an assembly line. If they work extra hard, the boss may reward them with a promotion. Even then, sometimes there’s little correlation between effort and reward.
Hear this loud and clear—entrepreneurs are not designed for pre-defined limitations.
To thrive, they need freedom.
Freedom to solve problems their way, not according to protocol.
Freedom to focus their energy and efforts toward making their vision a reality.
Freedom to reap the full rewards of their efforts.
Freedom to reach their full potential.
But here’s the catch—freedom requires time and money. And entrepreneurship is the only way to gain this control.
That’s because it places responsibility right where it belongs—with you. You become responsible for solving problems. You become responsible for critical decisions. You become responsible for company culture.
Above all, you become responsible for your own success.
If you’re an entrepreneur, you’ve already noticed that you were built different. The monotony, the boredom, the beige walls of being an employee aren’t for you. You just need an opportunity to spread your wings and claim the freedom you crave.
¹ “39 Entrepreneur Statistics You Need to Know in 2022,” Dragomir Simovic, SmallBizGenius, Feb 25, 2022, https://www.smallbizgenius.net/by-the-numbers/entrepreneur-statistics/#gref
² “Personality Traits of Entrepreneurs: A Review of Recent Literature,” Sari Pekkala Kerr, William R. Kerr, Tina Xu, Harvard Business School, Nov 2017, https://www.hbs.edu/ris/Publication%20Files/18-047_b0074a64-5428-479b-8c83-16f2a0e97eb6.pdf
It starts with massive success. You pick up a hobby, new skill, or start a business, and you’re crushing it. Everything you touch just seems to work.
But it’s short lived.
Beginner’s luck dries up. It gets hard to nail even the basics. You feel like you’ve somehow gotten worse the harder you try. Effort no longer translates to results.
And worst of all, you’re not sure why. Something feels off, and you have no clue how to fix it.
Welcome to the Dip. This dark valley is when MOST quit. It’s the boneyard of business. It’s where you’re faced with a choice…
Quit. Or don’t quit. That’s it.
This is the premise of Seth Godin’s classic The Dip. It’s fast and uplifting, and every aspiring entrepreneur should read it.
Godin shares two critical ideas…
1. Winners quit all the time. The idea that only blind determination will carry you through is foolish. Instead, winning is about knowing when to quit.
2. The Dip creates scarcity, which can bring massive opportunity. The more people quit, the greater potential you have to dominate your industry.
His advice? DO NOT quit when you first encounter the Dip. In fact, you must embrace the Dip for what it is—the opportunity to become a leader. As your competitors collapse under the pressure, you’ll become one of the few options in your market. It’s a powerful—and potentially lucrative—position.
But that’s not all. The Dip can also be an opportunity to strategically quit. Why? Because it gives you critical information about whether you’re on the right path. Godin gives some criteria on how to tell if you should push through, or quit and invest in another opportunity…
1. You’re not positioned to become world-class. Almost all the rewards go to the greatest. It’s an exponential drop-off after. If you can’t become world-class in the business you’ve chosen, then it may be wise to quit now and invest in something else.
2. You’ve made no measurable progress. The Dip causes panic. It makes everything seem like complete and utter failure. But there are often signs of progress. You just can’t see them because the Dip has blinded you. If you’re just panicking, stay the course. Keep pushing. Payoff may be just a few steps ahead. But if you’ve hit a dead end, quit now. You’ll be glad you did instead of sinking more money and energy into a failing venture.
The Dip is something every entrepreneur wishes they had known about before they started. It could potentially have saved them time, energy, and heartache.
But now you know about it! And that means you can prepare. How? Here are a few ideas…
Get mentorship. Seasoned entrepreneurs have experienced the Dip before. Their insight and wisdom can help you decide if the Dip is worth fighting through. So before you start your business, seek a mentor. Shadow them, ask them questions, share your ups and downs with them. It may be the best investment you make!
Make a plan. The more detailed your plan to become an entrepreneur, the better prepared you’ll be for the Dip. Why? Because a plan short circuits panic. It gives you objective benchmarks for success that can help restore your confidence when progress seems slow.
Build mental toughness. It’s a fact—the Dip will test your fortitude. Tapping out too early could prevent you from reaching your true potential. The greater your mental toughness, the more likely you become to reach the rewards on the other side.
The Dip is a challenge that many entrepreneurs face. It’s when the work gets hard, the rewards dry up, but it’s when most of your competition collapses. The Dip won’t last forever. Once you push past this difficult phase, rewards are ripe for the taking if you can exploit it to your advantage!
Why? Because starting a business shouldn’t feel impossible. The goal is to empower yourself to make as smooth a transition as possible from employee to entrepreneur. And if you don’t have answers for these questions, you could find yourself slamming into obstacles instead of sailing into your future.
What INDUSTRY will you choose? Consider stability, potential, trends, and size. Check your gut—can you see yourself working in this industry for the next stage of your life?
Who is your MARKET? Not what, but WHO. Who is the precise client group you will serve? Every industry is filled with different demographics and target consumers. Identify yours.
What’s your DIFFERENTIATOR? What makes your offering different from the competition’s? What is your special formula—your secret sauce? Could others easily copy it—or can you protect it from your competitors?
What is your clearly defined PRODUCT or SERVICE? How much will it cost you to make and sell? Who will provide your business with the materials, inventory, or services you need to run it?
What is the big SOLUTION you’re bringing to the world? Write down the one great problem you’re going to solve and why your market wants or needs this solution so desperately.
And lastly, what special ABILITY qualifies you (and any business partners) to solve this problem for your market? With the right skills, you’ll deliver results that amaze and delight your clients. And there’s no marketing better than a satisfied customer.
Once you have the answers to these six questions, you’re ready to make decisions about transitioning to entrepreneurship. It proves that you’re serious about making the move, and helps eliminate fears and doubts about the process.
Don’t delay! Answer these six questions TODAY so you can move forward with confidence tomorrow.
It’s a tale as old as time. An eager entrepreneur starts a business selling a clever product or service with world-class branding.
And it fails. Hard. After a few months or even years, it becomes clear that the business will never turn a profit. Investors bail, and the business eventually shutters.
Why? Often, it’s because there’s not a market for the product or service. And why isn’t there a market?
Because the product or service doesn’t solve a problem.
And if the product or service doesn’t solve a problem, why buy it?
Think about the most successful businesses in history. What do they all have in common? They all solved problems. From Standard Oil to Amazon, there’s big money in solving big problems.
Compare them to Quibi, the $2 billion streaming startup that failed within two years. It arrived in the streaming scene long after Netflix and Hulu had cornered the market, and as Disney was entering the fray. They were trying to solve a problem that had already been fixed.
So before you start your business, ask yourself this—what problem am I solving? How many people actually have this problem? Is someone else solving this problem better than I can? And are people willing to pay for my solution?
The bottom line is this—don’t start a business. Solve a problem. It can save you time, stress, and capital over the long haul.