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5 min read

Executive Letter #28: BYOB

Jul 11, 2022 9:00:00 AM

In the last few years, it seems a tidal wave of people have chosen to quit their job and finally live out their dream of being their own boss. 

Hey, I'm all for that. If it weren't for the spirit of entrepreneurship, I wouldn't be where I am today. I love to see people following their dreams—in fact, one of my team members just let us know that she's opening up her own vintage clothing store. When she told me, she knew I would congratulate her. She was also bracing for the torrent of questions I was sure to rain on her about overhead, stock, and strategy. I didn't hold back. 

As excited as I am by seeing young entrepreneurs come into their own, I can't just slap them on the back and send them on their way. I want to make sure they're prepared for the uphill battle ahead, because no one prepared me. 

There are quite a few myths out there that have been busted, but today I wanted to take a different approach by instead sharing some truths that might be tough to swallow.

If you're ready, keep reading.

Truth #1: It Will Be Stressful 

If you're determined to be your own boss because you want more freedom, you're going to be disappointed. Especially if you're one of those people who's behind the 4-hour work week BS

Sure, by starting your own business you might be escaping an 8-5/5 day work week, but you've traded it for a 24 hour/7 day one. You won't be able to keep track of the sheer amount of time and energy it takes to do something from scratch, even if it uses all the skills and talents you've built up over time. 

Whoever said "If you do what you love, you never work a day in your life" was exaggerating. 

Starting your own business means that instead of having one boss, you now have many bosses such as: your clients, your investors, and more (depending on how your business is structured, they are all on the line and holding you to accountability every minute, of every day). In short, your company is your boss, and it's sure to be the nastiest one you ever had. 

Why? Because your heart (and money) is in the game this time.

Truth #2: Your Ego Will Take Some Hits

Starting your own enterprise takes a lot of confidence. Perhaps even arrogance.

You're placing a bet on yourself over every other choice you have around you. You're saying that your abilities (or your know how, your taste, or your team) are on par with your competitors. 

People don't tell you just how much of a business is convincing other people that your product or service is valuable—or how personally you might take it if they don't see that value, even after all your hard work. 

Can your self-confidence take it if your business has a bumpy start? Can you persevere even when you're not getting the results you want? 

Truth #3: The Exit Strategy Can Be Pretty Ugly

In Chris' podcast for this week, he shares something about investing partnerships that applies to nearly any venture: Don't start something without knowing how it will end. (Listen for this tip in episode 27, out this Friday)

In other words, don't do yourself a disservice by pretending things will never end, because you'll be caught with your pants down when they inevitably do.

When it comes to thinking long-term about your start-up, I recommend planning for two possibilities: what happens if everything goes right, and what happens if everything goes wrong.

If your business is as successful as you imagine it could be, what is the end game? Would you work there until you die? Would you hand it down to your heirs? Would you sell it and use the profits to retire on? 

What are the next steps if your business flatlines? How will you decide what to do with the pieces? How will you communicate with everyone who invested in your venture?  

It may feel like I'm prescribing an unlucky practice, but believe me, "luck" is a myth and success only comes through preparation. 

Commit to The Grind

If you've read this entire thing and you still want to go out and be your own boss, then I wish you well.  

Nothing makes me prouder than knowing I've done what I can to help others achieve more than they ever thought possible, whether it's accumulating a passive income portfolio or starting their own business from the ground up. 

If I've inspired you to do either, I hope you'll drop me a line. 

Until next time,

Article Graphics (8)-1

Kent Clothier
Chief Grind Officer


About Kent Clothier

CG5A0010-1Entrepreneur, Real Estate Investor, Husband, Dad, and Granddad. Through decades of personal experience, and a few other titles, Kent built a strong community around him at REI Nation. But it didn’t start there. It took 22 years of entrepreneurship – of losing money and making money, building small businesses and multimillion dollar companies alike – before he founded a family business-turned-empire. His sons Kent Jr, Chris, and Brett have worked alongside him, as well as leading successful ventures of their own. Real estate trends, managing towards efficiency, excellent customer service and leading the industry are what fuel him. Over the years, the skills he’s come to value are financial acumen, honesty, and forging new paths in business, investing, and winning.

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