Before You Become an Entrepreneur Read This…

By Charles Sizemore  |  July 24, 2019

Before I joined the team at Charles Street Research, I was an entrepreneur. I wrote and edited my own value investing newsletter.

It was awful.

It wasn’t the newsletter that was awful. I was actually really proud of it. And my readers got a lot of value out of it, too. Nor was the labor of writing awful. I actually really enjoyed that part.

The Ups and Downs of Being an Entrepreneur 

What was awful was running the business completely alone. I wrote the newsletter copy, I edited it, I laid out the PDF, I maintained the website, I ran the billing and order fulfillment and dealt with customer service. I was even my own tech support and janitor.

Worst of all was not having anyone to talk to about it. I had no one to high five when things went well and no one to commiserate with over a beer when things were going poorly. When you are an entrepreneur, you get really sick of yourself.

And the ups and downs were extreme. Some days I felt like I was conquering the world. Others… I felt like I was drowning. There was the constant fear that I was always one setback away from going out of business, and I had young children to feed.

Looking back, all of it was an incredible experience, and I’m better for having gone through it. But I don’t know that I would wish it on anyone, and I’m quite happy to have a team — Adam, John, and the rest of the Charles Street crew — around me now. There’s a lot more to be gained as a group than in solidarity.

Take Adam’s latest service, Cannabis Paydays, for example. I would’ve never considered even looking at the industry. It’s nothing but hype to me. But by applying his method of investing to it, he’s uncovered potential investments that could generate 1,000% winners. And it’s inspired me look to different sectors I didn’t consider in Peak Income

But I digress.

Anyway, I was thinking about all of this as I was reading a piece in The Wall Street Journal that really laid bare the emotional fragility of entrepreneurs. The piece focused on tech start-up founders, but I’d argue it applied equally well to a sandwich shop owner, or just about any entrepreneur for that matter.

In the piece, Ramachandran and Winkler wrote, “many founders and early-startup executives are striving to build pioneering businesses while wrestling with issues like anxiety, drug addiction, insomnia, depression and binge eating.”

The article went on to say that entrepreneurs were 50% more likely to have mental-health conditions. I thankfully never had issues with substance abuse. But I had anxiety, insomnia, depression and junk-food binge eating habits in spades…

This raises the eternal chicken or egg question. Does starting your own business wreck your mental health, or are people that are already half crazy naturally gravitate to the quirky world of entrepreneurship?

Panning For Gold

It’s a little of both. It takes a certain bit of craziness to eschew conventional wisdom and the safety of a paycheck. And as I can attest, if you weren’t crazy before you started your business, you’ll be stark raving mad within a few months of doing so.

All the same, there’s never been a better time to try your hand at entrepreneurship than now. And you don’t have to be a tech wiz either.

Think of the cannabis legalization gold rush going on in Colorado, California, and the other nine states where recreational use is now legal.

Or if that’s not your thing, think of the boom in healthy, organic foods, holistic CDB medicines and creams, or even in personal meal catering.

I’m not going to necessarily recommend you go out and start your own business. That’s a decision you have to make on your own. But if you’re feeling the entrepreneurial itch, let me at least give you a few pointers.

    1. A rising tide lifts all boats. I specifically mentioned cannabis legalization because that’s effectively virgin territory. Whenever it’s legalized in a new area, there are no entrenched competitors to deal with; the floodgates open and the money flows. That’s a huge plus. Whatever you choose as your business, make sure the industry isn’t already saturated. I love craft beer. But there is no way under the sun I’d consider opening my own brewery. There’s just too much competition now.
    1. If possible, start your business as a side hustle and keep your day job. Or, if you have a working spouse, try to live on their salary alone while you build the business. One benefit of starting your own business is that your lifestyle expenses actually drop. You’re too busy to take vacations or hang out at bars after work because you’re likely working 20-hour days. But you still need to eat and still need a roof over your head. Keeping your day job or depending on your spouse’s salary, at least in those early months, can keep you financially afloat while your business is coming together.
    1. If you’re married, make sure your spouse is on board with your project because starting a business will put stress on your marriage. If you’re working at all hours, someone still has to feed the kids and take out the garbage. Plus, you’re not going to be emotionally available, and the stress will make you hard to live with. They’ll resent you for being constantly distracted, and you’ll resent them for not understanding. So, before you commit yourself to this, have a real chat with your husband or wife and make sure they understand the scope of what you’re doing. And when they blow up at you a couple weeks into it, it’s not because they don’t believe in you. It’s because they’re frustrated that they don’t see you as much as they want to.

Entrepreneurship Isn’t For Everyone

And that’s perfectly fine.

And if you’re looking for outsized entrepreneur-like payoffs but still like the idea of limiting your responsibility to a few mouse clicks, check out my friend Adam O’Dell’s new service, Cannabis Paydays. Adam looks for wildly profitable opportunities in the legalized cannabis space, and his early results have been solid — bagging an average trade of 856%, including both winners and losers, with the winners being 53 times greater than the average loser.

It’s pretty incredible stuff.

Applying a systematic method, Adam means to leverage the budding industry as it continues to grow and is legalized throughout the states by pinpointing the cannabis stocks with the most momentum.

If you’re looking to get an edge on the competition and start learning more about the cannabis industry overall, I think this is just the thing for you. Click here to learn more about Cannabis Paydays.

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Charles Sizemore

Income and Retirement Strategist, Charles Sizemore, CFA specializes on dividend-focused portfolios and building alternative allocations by finding value opportunities outside of the mainstream stock market.

Charles is the executive editor and portfolio manager for Dent Research's premium newsletters, Peak Income and Peak Profits.

He is also a frequent guest on CNBC, Bloomberg TV, Fox Business News and Straight Talk Money Radio, and has been quoted in Barron’s Magazine, The Wall Street Journal, and The Washington Post. He is a frequent contributor to Forbes, GuruFocus, MarketWatch and

Charles holds a master’s degree in Finance and Accounting from the London School of Economics in the United Kingdom and a Bachelor of Business Administration in Finance with an International Emphasis from Texas Christian University in Fort Worth, Texas, where he graduated Magna Cum Laude and as a Phi Beta Kappa scholar. MORE FROM AUTHOR