9 things 5 years of running my own business taught me.

Five years ago, I started my business.

After 15 years of working in corporate America, I turned my side hustle into my full-time gig.

It hasn’t been easy, but it was without a doubt the best career decision I’ve ever made.

Over the years, I’ve learned a few things. Here are some of the most important:

1. The client who pays the least will demand the most.

If a client fights you during the price negotiation, they are probably going to fight you during the entire project. The initial negotiation is more than just a price decision, it’s an audition. It’s your chance to see who the client is and how they do things. If they’re a jerk upfront, don’t make the mistake of thinking the stress of the actual project will make them act better. It’s like assuming that marriage will fix a bad boyfriend. The other problem is that often, the cheap client has stretched their budget to get up to your level. It’s like saving up for a year to book a first class flight. The guy who always pays for that level won’t be as demanding. The person who can barely afford it will get frustrated if the snacks don’t show up on time. They will have crazy high expectations because in their mind they paid crazy high prices. I’m not opposed to doing discounted work with clients I know and love. I do that fairly regularly, but I will rarely expect a reduced rate to go well with a brand new client.

2. You have to reinvent your business every 6-12 months.

The secret to having a profitable business is actually pretty simple. You must have higher revenue than your expenses and you must have 7 faucets of revenue going at any given time. Why so many? Because that way when 3 get shut off outside of your control, you’ve still got 4 moving along. Public speaking is one of my 7 and it’s amazing, but if a client cancels an event, I don’t have any control over that. I better have something else going that month. On an even larger level, you have to be willing to constantly reinvent what you’re doing or you will get left behind. Just when you get comfortable, a new technology will hit the scene and completely shift what you are doing. You don’t need to change who you are or what your brand is all about or your mission. But if you get stuck, your company won’t last very long.

3. Your spouse probably doesn’t want to be your coworker.

My wife quit working with me two years into my business. I like to say she got fired but quitting is a lot closer to the truth. She essentially said, “I want to be your wife, not your coworker.” Essentially, the business was dominating every interaction we had. We were either working or talking about working. Every date night started off well but ended with a budget or marketing discussion. Can couples work together? Of course. I have friends in Denver who run a multi-million dollar company, but they’re rare. If you’re married, be very, very careful about working together.

4. It’s lonely running a business.

I love companies. I’m not one of these entrepreneurs who slams big businesses or corporate America. I think there are many benefits to working at someone else’s company. One of them is that you have casual community. When you work in an office, there are people to go to lunch with every day. When you work in an office, there are people to talk to over coffee. When you work in an office, there are coworkers who care about you. Do you know what you don’t have when you start your own business? Any of those things. If you’re not careful, you’ll get real lonely, real fast. When you run a business, you have to go out of your way to build community.

5. The sexy things are fun but not as productive as the boring things.

Snapchat is more fun than email. Twitter is more fun than writing a thank you note. Instagram is more fun than a follow up phone call. But over the last five years I’ve learned that the sexy things tend to be high on fun but low on value. Is social media important? It is, but if you had $100 to invest in your business I would beg you to put it into email marketing. All of those little, dumb things you might not like doing are actually the key to growing your business. Don’t get distracted by the shiny.

6. There’s a ton of money and opportunity out there.

People will often tell me, “I missed my opportunity with the Internet or social media.” Or they’ll say, “There are already too many entrepreneurs, photographers, authors, etc.” We tend to buy into the thought of “once in a lifetime moments” and assume that we’ve lost our shot at them. That’s just not true. I think there is more opportunity than there has ever been. There’s more money floating around, too. It might not be easy to get it. It might take time and hustle, but it’s there. I don’t care if there are 100 million entrepreneurs out there, there’s still a shot for you.

7. People will make you better.

Don’t buy the lie of the “solopreneur.” No one is a solopreneur. Everyone needs someone. My business runs because I work with Ashley and Bryan. My courses work because I work with Alejandro and Savvy. My public speaking gigs work because I work with Premiere Speaker’s Bureau. My book deals work because I work with Curtis and Mike. My books work because I work with Margot and Bria. That doesn’t mean I have a huge team. None of those people are my full-time employee. They’re experts I work with so that I can produce expert work. Do your best to surround yourself with the people who will make your business smarter, faster and more efficient.

8. You will have more bosses.

I love when people say, “I want to be an entrepreneur so I don’t have to answer to a boss!” That is adorable. The reality is that when you become an entrepreneur, you end up having more bosses than before. When I worked at Bose, I had one boss. Her name was Suzanne. Now that I run my own company, I have a dozen bosses. I work for Reggie Joiner, Portfolio books, brightpeak, Kristen Ivy, and every speaking client I have. Are they technically my boss? Maybe not, but I do report to them. I do fulfill their project requests. I do my best to make sure they have everything they need. When someone says they don’t want a boss, what they are saying is, “I don’t want to answer to anyone.” You might not end up with a boss, but if you build a company you will 100% answer to a lot of people.

9. You won’t take vacation unless you’re deliberate.

I always laugh when people say, “I want to run my own company because then I can take as many days off as I want!” Hilarious. The truth is that unless you’re hyper deliberate about vacation, you won’t take it. Part of the reason is that unless you figure out how to keep the business moving without you, the loss of revenue will always inspire you to be working. It’s taking me five years to learn this but I’m getting better. I tend to take at least 6 weeks off every year.

You should never end a list at 9 points, but the 10th point was fake. It was just me trying to fill out a list.

I’ve got a few more ideas about building a successful business so, for the first time in a year, I’m opening up registration for my 90 Days of Business Hustle Course.

I promise I’ll help you do two things:

1. Find something you love doing so much that you’d do it for free.
2. Get so good at it that people pay you a lot of money to do it.

That’s it.

Whether you’ve had a business for 10 years or just an idea for 10 minutes, that’s what I’m going to help you do.

Registration closes in 4 days (Monday night, 3/12/18) and I won’t open this class again in 2018. This is your chance.

You in?

4 Comments
  • Kyle
    Posted at 18:15h, 13 March Reply

    All great points. Just finished your book, Start, on audible for the second time. Really a great listen! Thank you for that. About to begin Finish. I started my side business this month. It is very easy to get sucked into this King that too many people are already doing what I’m planning to do. However, none of them will do it the way that I do.
    Looking forward to listening to the next book since I have a tendency to start some things and not finish.

  • Andrew Brashaw
    Posted at 18:41h, 13 March Reply

    Always love reading your stuff, but this piece is especially relevant. I launched my business a month ago and need every piece of advice I can get.

    All 9 of these things are great. #1 hits me the hardest because I’m already learning this just 30 days into my business.

    Thanks for writing!

  • Kevin Michael Geary
    Posted at 11:43h, 15 March Reply

    Oh man, this list is soooo on point. I’ve experienced pretty much every single thing on this list. #4 is the one I’m struggling with most right now.

  • Debra
    Posted at 00:35h, 20 April Reply

    #8 was the biggest surprise to me — you forgot to add CRA or the IRS depending on where you live, government employees at every level, your accountant, business partners if you have any…actually I think the list of bosses may be endless. I’m just about finished Finish. There is so much irony in that, it isn’t even funny. Or it is. Kinda. Thank you for writing it. Your description of fearing walking into the Apple Store is definitely the funniest piece I’ve read in eons. (Yes, I need to upgrade my computer.) Funny how “funny” means “resonates excruciatingly well.”

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