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33 Things Every Aspiring Entrepreneur Should Know

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33 Things Every Aspiring Entrepreneur Should Know

A few months ago, I crossed the threshold of five years of self-employment with little fanfare or notice. At the time, I was too busy redesigning the site, correcting major payment processor issues that likely resulted in the loss of five-figures worth of revenue, and my girlfriend kept dragging me to a variety of Brazilian beaches. It was a weird month. If you had asked me in 2007 when I started what I envisioned my business to look like five years from then, I simply would have said that I didn’t. I didn’t envision anything. I started my first iteration of my business like most feisty online entrepreneurs and wanted to make what seemed at the time like “easy money” (Hahahahahahaa! *cough* …ahem.)

Obviously, things didn’t work out that way. Well, except for the hot girl and Brazilian beaches part. I guess that part did work out. But I sure imagined I would be working less. And enjoying it less as well.

Here are 33 things I wish I had known when I started my first business.

1. Sell everything. Save money.

This one would seem obvious, but it’s easy to get ahead of one’s self. My first business actually got off to a strong start. So I chose to “reward” myself with a gratuitous trip to Buenos Aires with some friends and proceeded to blow most of the money I had saved up from my first six months. Less than a year later, I would be broke and begging my ex-girlfriend to let me live with her so I didn’t end up on the street. Don’t make the same mistake I did.

2. Monetize your free time.

A big complaint of a lot of people who want to start businesses is that they don’t have enough “free time.” Between work, hobbies and social obligations, they have maybe an hour or two a day to sit down and hammer out that new business idea they’ve been sitting on.

No, no, no, wrong, wrong, wrong. If it feels like you’re giving up your free time to work on a second job, then you’re screwed before you even start. Take what you love to do anyway — basketball stat analysis, home gardening, furniture carving, whatever — and simply monetize that. That’s your most obvious starting point. That way you’re not giving up any free time, you’re expanding it.

3. Surround yourself with other entrepreneurs.

A great point Dan Andrews made on a podcast with me was to surround yourself with the type of people you want to become. If all of your friends are bored desk jockeys, then there will be an unconscious social pressure for you to continue on as a bored desk jockey. They will not understand your aspirations, or even worse, they may resent them. Find other people who are in a similar position as you and push and motivate one another.

4. Quit your day job as soon as is reasonable.

I wrote about this extensively here. Burn the boats behind you. Give yourself no option of retreat.

5. Be shameless.

Aspiring to do something no one else has ever done takes a certain degree of delusional self-belief. You must be willing to make an ass out of yourself here and there. Cold-calling dozens of prospective clients and telling them that you can do a better job for them than anyone else. Pitching your new product to people who didn’t even know it existed. Promising delivery on content or services which you only kind of, sort of, know how to deliver on (but are willing to figure it out as you go along). You have to be shameless about this stuff.

6. Fuck your business idea.

Man standing next to car in old black and white photo
Henry Ford didn’t invent the car. He just figured out how to build them better than anyone else.

Mark Cuban once said that for every great business idea you have, you should assume that 100 other people have had the same idea and are already working on it. Business ideas don’t matter. What matters is execution.

A lot of people are proud of themselves for coming up with a cool idea. But the most successful businesses in history were rarely new ideas. Google wasn’t a new idea. Facebook wasn’t a new idea. Microsoft wasn’t a new idea. All of these companies merely executed better than anyone else.

7. Less reading, more doing.

Try to only read when you need a specific solution to a problem you’ve run into in the work you’re doing. For instance, don’t just sit around and read about marketing because you think maybe you should know about marketing. Ugh, how fucking boring (this, in a nutshell, is why college kind of sucks by the way). Read about marketing when your new project needs a new marketing strategy. Suddenly, that same reading becomes a lot more interesting.

Many people use reading up on what they want to do as a way to avoid actually doing what they want to do. Reading is useless without execution.

8. Test, test, test.

You don’t know anything until you’ve tested it. I don’t care if Frank Kern said it or Dan Kennedy said it or your step mom said it. You don’t know until you test it. Every marketing seminar I’ve ever watched and every marketing book I’ve ever read told me to raise my prices. Yet, every split-test ever I’ve done on my books through this site, the lower priced book not only killed it in terms of revenue, but also generated more referrals, more positive reviews and more traffic to my site.

9. Be eccentric.

You can’t stand out unless you’re different. Capitalize on your quirkiness.

10. Obsess about your brand.

The reality of the current economy is that pretty much any information, product or service a person wants, they already have dozens of choices of who to purchase them from. Scarcity doesn’t exist anymore. Differentiation purely through price or quality is an almost impossible strategy for entering or dominating a new market. What dominates now is brand. Your brand defines the relationship you have with your prospect and customer. It’s why they come back to you and not the other 11 Joe Schmoe’s offering the same exact service.

11. Don’t deliver a product, deliver an experience.

Steve Jobs said that he wanted Apple products to provide an experience, not just a function. Apple is possibly the strongest brand on the planet right now. This is what I mean when I say obsess about your brand: obsess about the experience you’re giving your customers, not just the information or product you’re giving them.

12. Believe in what you’re doing.

Otherwise, even if you do become successful, you’re just stuck in another grind. But this time, it’s of your own making.

13. Your business will evolve. Let it.

No one gets it right the first time. Or the second. Or the twenty-third. Cue cliché about Thomas Edison or Michael Jordan here. Information is always imperfect. Markets are always changing. What worked last year may not work this year. You don’t stay on top of things unless you’re evolving with them. Don’t marry yourself to your idea or original business plan.

14. Fuck Your Passive Income Dreams.

If you’re only working four hours a week, your business is going to be antiquated within a decade and chances are you’re getting bored as shit with your life anyway.

15. A blog is not a business plan.

It’s just not. Don’t start a blog to make money. Start a blog because you love to write. Start a blog to share something you love. But don’t start a blog to make money. No blogger who is making mega bucks off their content started that way or planned it that way. It just happened. And it took years. Not months, years.

16. You’re going to need either a lot of time or capital.

Or both. There is no such thing as overnight success.

17. Business is not about making money.

Plant growing in pile of gold coins

It’s about value and values. If you continue to monetize what you personally value, you’ll never tire of working (in fact, you’ll look forward to it). If you optimize the value your business generates, the money will happen as a side-effect. There’s a subtle difference between value and money. Sometimes you must eat a chunk of money to create greater long-term value. If you’re just in it for the bottom line, you’ll never be willing to do this.

18. Capitalize on luck.

You’re going to have good luck and bad luck. We all do. No sense complaining about it or taking credit for it. Instead, hunker down and be sure to capitalize on both.

19. Slow to hire, fast to fire.

Cliché, but true. Especially when outsourcing. Almost every internet entrepreneur I have met has horror stories about outsourcing, myself included. Short version: you usually get what you pay for.

20. Embrace existential stress.

When you have a job, your stress is about external approval — deadlines, meetings, presentations — and it usually comes from your boss. It’s annoying and it comes in short, strong bursts.

When you work for yourself, you give up having to constantly fight for this external approval. What you trade it in for is this low-level, constant gnawing sense that everything is going to collapse and disappear one day. Yeah, I can wake up at noon every day. I can work when I want. But in a corporate job you don’t have to worry about showing up to work one day and the building not being there anymore. An entrepreneur thinks about this on a weekly basis.

21. If you’re not pissing some people off, you’re doing it wrong.

Dan Kennedy said, “If you haven’t pissed someone off by noon, then you probably aren’t making any money.” My experience has shown this to be true. As I once said:

“You cannot be an attractive and life-changing presence to some people without being a joke or an embarrassment to others. You simply can’t. You have to be controversial to succeed.”


22. Did I mention you should be testing?

Seriously, half of the stuff that grows your business is impossible to implement if you’re not regularly testing your ideas out in the marketplace. Hell, don’t even START your business until you’ve tested the idea out in the marketplace.

23. 80/20: Never forget.

It really is staggering how much it applies to.

1000 True Fans chart

24. Get 1000 True Fans.

The idea is that in the internet age, you only need to convince 1,000 people to give you $100 per year to make a six figure income. When viewed in those terms, it’s far less intimidating. Corollary to this is the 100 True Customers idea, if you’re in the consulting/services world.

25. As in the corporate world, networking is everything.

Yes, it’s still a great way to get new clients and/or job offers. But in the entrepreneur world, it’s even more useful to see what’s working for other people’s businesses and what you may be able to steal and use in yours.

26. Know thyself.

I work best at night. I hate structure and make lots of lists, half of which I never look at again. I manage my time with iTunes playlists. A lot of the things that work well for me fly against all of the time management advice you’ll ever read out there. But this is how I’m wired and I cater to what works best for me. Do what’s best for you.

27. The 1000 Day Rule.

The 1000 Day Rule states that you should expect to be WORSE off than you were at your day job for the first 1000 days of your new business.

28. If it feels like work, you’re doing it wrong.

You can either make money to do what you love, or you can do what you love to make money. You choose.

Woman catching elephant poo in bag

29. Don’t get rich quick.

All of the shortcuts for short-term gains either gut your long-term brand and loyalty, or they just put you back in a position of being chained to something you don’t care about or believe in. If you love what you do (and you should), and you’re investing regularly in the evolution of the business (which you are), then having a bunch of money sitting around to buy useless shit should not be a priority of yours. Seriously, get some self-esteem somewhere else if it’s that important to you.


I don’t know the answer! And neither do you! So test it and find out!

31. If you’re not scared to death of abject failure, you’re doing it wrong.

In fact, I’ve found that the more something terrifies me (i.e., writing the new book), the more I need to be doing it.

32. Treat your customers like family.

They’re the only reason you’re here in the first place. Treat them with respect. Reply to their emails promptly. Answer their questions. Give them free shit.

33. This will be a part of your permanent identity, choose wisely.

The idea of, “I’ll do this for a few years, make a bunch of money for a few years, and then go do what I really love!” is a myth. It never works out. That’s how I originally got into this business, and I see dozens of people doing the same. Yet, it never happens.

Exit sign to careers

Eventually I had to suck it up and admit that what I had created was a career in internet marketing, whether I intended to or not. And since I was stuck with this as a career, I might as well turn my assets into something I was passionate about and loved doing. When I created one of the first versions of this website, I gave up my other business ventures and effectively cut my monthly income in half. But, I figured, if this is what I’m passionate about, and I love doing it, it will be more than worth it in the long run.

And it already has been…

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