Entrepreneurship. A lot more people fuck up, go broke, quit, commit suicide, or have their financial lives ruined by entrepreneurship than those who make it.
That doesn’t mean it’s impossible, it just means you can’t do what the average person does, if you’re looking to survive (and thrive).
Here’s what I wish I knew four years ago, that would’ve made my survival that much easier.
And here are the things I’ve noticed pros do, that amateurs aren’t even aware of.
Lesson #1: People Don’t Start for Immaterial Reasons; People Usually Fail for Material Reasons.
Of all the masterminds I’ve been in, of all the people I now coach in the Milk the Pigeon mastermind, I see the same thing over and over.
People don’t start for immaterial (read: mindset) reasons.
Who would read this? I’m no pro. <self-esteem question>
How is this ever going to work out? <self-doubt>
Is this going to envelope my whole life, until I’m stressed out, bald, and can’t get it up anymore? <irrational fear>
But the paradox is that sometimes, people fail for the same reasons. But they definitely fail for the same, main reason: no money.
I found this dichotomy interesting, the immaterial is why we fail to start, and not focusing on the material, is why we start to fail.
Regardless of whether or not you’re a die-hard capitalist or an idealist who is driven by purpose, you still have to focus on the dollars and cents to stay in business.
Lesson #2: You Have to Become a “Figure it Out” Person, if You Aren’t One Already
One of the biggest things I had to learn, that has served me for life, and will continue to serve me, is a part of my new persona:
How to be a “figure it out” person.
The entire fucking game of entrepreneurship is, “Shit. This isn’t working. Why not?”
… And then deciding how to respond to that.
One series of studies profiled on Valedictorians found little link between their impressive grades in high school, and becoming successful, “world changers” later in life.
One theory was that valedictorians are good at playing the school game. They follow the rules. They don’t stir things up. They go by the book. They don’t innovate, they just follow procedures.
The problem is, with entrepreneurship, there is no fucking book. A good chunk of the time you can emulate people, you can model what works, but if you really want to do something that has never been done before, good luck. There is no teacher for that.
The teacher is called “smash your head into the wall a hundred times, then do it another hundred times.”
I was a good student in high school. I basically just did what I was told, went home, played video games and did some homework, and got average grades (a 3.2 GPA). When it became time to be an entrepreneur, I was shocked at how much homework was required.
I have no idea how to get traffic to a site.
I have no idea how to make sales of a digital product, or hell, even make a digital product.
I had no clue how to do ANY of this shit, as a result, at the start I floundered. I didn’t realize that the first part of the sentence was:
I don’t have a fucking clue how this is going to happen…
But the second part was:
…It’s my job to figure it out, so let me get to work and test a few things out.
It was shocking how much my personality changed in real life too. Something isn’t working in my relationship? Read a damn book on relationships, try something out, see if it works.
That sink keeps dripping? Learn how to fix the goddamn sink. Buy the part. Install. It either works now, or it doesn’t.
I had never observed earlier in my life that I was good at following instructions, but never at creating the instructions when there were none.
Now, I am.
Lesson 3: Every Pivot Increases Your Chance of Success
There’s a common belief that if you “don’t just get it right the first time” you’re basically screwed in business.
Sometimes, that’s true.
But that hasn’t been my experience talking to other internet entrepreneurs.
My business started dealing with back pain, and now, it’s geared towards weight loss. I didn’t know what I was doing, got really good traction at the start, writing epic content, and then realized that was not what my audience wanted, or what they wanted to learn more about.
It required tons of work to re-pivot that, release new products in a new industry, and get traffic more related to what I wanted to create, but I did it.
Many of the friends I have (with businesses that are working), have gone through many different iterations.
Sometimes those changes meant narrowing down their business target market, and sometimes it meant re-branding entirely.
A few times, it meant starting new businesses altogether, which was what I went through too.
Lesson #4: Entrepreneurship is Really Fucking Hard
I know it sounds obvious to say this, but intellectual people won’t get it anyway. Entrepreneurship is really fucking hard. Extremely.
If that wasn’t obvious, it should be. Because I hear smart people (like me, before I actually owned a real business), say, “Really, it’s that hard?” I thought the same thing. Just work hard. Be different. Choose a niche. Create a great product.
Thing is, each one of those things can literally take years to learn or figure out. And add in a few years for messups, add a few years for setbacks or changes in the industry, and you can see why it’s so difficult.
If you have any personal issues going on in your life, it’s going to be that much harder.
I’ve seen 90% of my friends who wanted to start a business, never start one. Or they’re committed for a day, or a week, but never for more than a month.
I’ve seen my closest friend commit suicide, which I think was largely due to the stress of entrepreneurship.
And I’ve seen untold numbers of other people I know experience: divorce, hospitalization from overwork and stress, relationships end due to financial variability, nervous breakdowns that resulted in hospital stays, quitting businesses to go back to day jobs, and everything in between.
And to top it off, it is a fuckload harder on a person’s emotional life… the constant self doubt you experience, wondering if this is ever going to work, that can literally last years. It wears on one’s spirit, and sometimes, crushes it under the weight.
Lesson #5 It’s Even Harder If You Have a Full-Time Job – But You Can Do It
My life for over 3 years: it existed between 11 and 11:30 pm.
This was my life for 3+ years.
7 – wake up for work.
8:30 – go to work.
5:30 – leave work.
6 – 7 – go to the gym.
7 – 11 – side hustle and eat dinner.
No Tv. No drinks with friends during the week. Hell, I didn’t even see my girlfriend except on the weekends for over 3 years.
All I’m saying is that if you want this shit to work, you’re going to have to put in time. And when you already are at a job for nine hours a day, where are you going to find 2-3 hours a day to make this a reality?
I had so many friends that lived in developing countries who were engaging in geoarbitrage – living on a first world income in a second or third world country. That was a smart way to do it.
And for years, I resented them because I was so jealous.
I was fucking KILLING myself working every night and every weekend to turn this business into a reality. They could chill and work less than 40 hours a week and have a luxy life.
I was putting in 70+ hour weeks, fucking hating every minute, waiting until I could quit.
The reality is… for most of you, this will be what it takes. You can do it. It will not be easy. But you can do it.
The biggest thing it will require is great time management, and sacrifice. You just have to decide what’s worth sacrificing. It might be easy – only 1 hour of Netflix instead of 4. Or it may be hard – sacrificing time with your partner.
Lesson #5 : It’s Still Harder if You Have a Full-Time Job and Family. But You Can Do it.
Okay, well I also have a family, and a job, how the hell is this going to work out?
I can share one thing:
You may not have three hours a night to work on your business after your kids go to sleep. Maybe you have 90, exhausted minutes at best.
Start making those 90 minutes count. I had a client who only had 1-2 hours per night to work on, and once she got to making an extra $1,000 a month with that time, she felt comfortable enough to scale down her day job hours (because they were flexible).
She started working only 30 hours a week, and then 20, to balance the side hustle alongside it.
Maybe you don’t have that kind of flexibility. No worries, figure out how you’re going to get it.
This dude wrote a fucking book commuting on the shitty NYC subway system every day, and his books have been doing awesome.
What’s your excuse?
Lesson #6: Despite These Things, It’s Possible – And Only 2 Things “Guarantee” Success
Let me start by being an asshole, and saying:
If you want guarantees, don’t start a business.
At the same time, of the hundreds of new books on success that come out each year, promising a new formula for riches, there’s usually only two things you consistently see.
A person wants to reach a goal.
They try to reach the goal one way.
It doesn’t work.
They try another way.
They either continue, or they quit.
So the only two factors that are consistent, usually are:
- Quantifying everything
- Testing something new to improve a core metric
(If it doesn’t work, throwing more shit at the wall – until something does stick).
Sometimes you emulate what a person does in your exact industry, and it doesn’t work. What the fuck. Why not?
Sometimes you emulate a strategy in a similar business in a different niche, like a deli, or coaching business, or consulting business, or in marketing your book, and it works. Or it doesn’t.
Either way, every entrepreneur starts out with an idea.
I need more people in the door.
I need more sales.
I need more people to buy my book.
And then they come up with a list of strategies, and test every single one out. The “spaghetti on the wall theory” has been the only consistent trend I’ve seen. As a result, the quicker you throw spaghetti on the wall and see how it sticks, the sooner you find a winning strategy.
And the more things you throw at the wall to test, the faster you can reach your goals.
Like Darwin, in entrepreneurship, it’s not the strongest or the smartest that survive, but the ones most adaptable to change.
Lesson #7: Always Play the Long Game, Unless You Want an Exit.
Most people I talk to throw out some pie-in-the-sky figure, that they want ten million dollars in the bank after they sell a business.
But for most of us, it seems like having a small, manageable business that provides freedom is usually what people want.
Because inevitably, when I ask, “why” I hear the same two things:
I want time, and I want freedom, to do whatever the hell I want.
It’s always some variation of these two simple ideas, the time and the freedom to live. It’s interesting that these are considered the exact opposite of what’s usually present in the average person’s life.
Ironically, I see people play the short-game all the time, and they always lose.
It’s funny, sometimes people use the example of not chasing “quick cash” in a business, because you’ll screw up later down the line. But what I find is more true is that people who play the short game have the entirely wrong vision for building a business.
Here’s what I mean.
Working 14 hours a day. Almost anyone can do this for a day, a week, a month, or maybe a year. But what if it takes you 3+ years to quit your job, like it took me? Are you willing and physically able to do that? Will it destroy your health or your relationships?
Doing shit you hate. The most common version of short-term thinking that I see is that people do shit they hate to build a business. If they want to build an online community, they write (even though they hate it) instead of doing video. If they want to train people in a gym, they do physical workouts (that they hate teaching) instead of nutritional and mindset coaching. Doing shit you hate is the fastest path to your business imploding or you burning out in the long run.
Building a business just for the money, despite not liking it. A lot of business people disagree on this, but I have my own two cents. I’ve seen a lot of people quit because they just wanted money, but grew to hate the exact day to day rituals that earned them the money.
Thinking about the money metric, and not the lifestyle metric. Another followup is building a business where you just say, $5k a month is ideal… then $20k a month is my dream business. Well, congratulations, you said literally nothing else about your business.
Do you want to work 20 hours a day?
Do you ever want a vacation?
Do you want to have a wife or husband and kids?
Do you want to be able to travel remotely and work?
Do you want the luxury of being able to work on fun projects?
Do you want to do 1:1 coaching for that money, live off book royalties, or have online programs? Something else?
If you don’t clarify anything else, more often than not, you don’t get anything else.
Lesson #8. Your Core Metric Should = The Energy Metric.
When I read Scott Adam’s book, How to Fail At Almost Everything and Still Win Big, he shared a passage that really intrigued me.
He talked about his method for deciding on what to work on (which side-hustle ideas). The idea of the “energy metric” is simple.
Especially when you have a full-time job, your energy is incredibly limited. When you get off work, or before you go to work, you have to use energy – so the projects you should work on should be the ones you have the most excitement for, that give you the most energy.
If you have the most energy for the project, you’ll do the project. If not, it’s easy as hell to procrastinate, especially with a full-time job.
For me, it took over 3 years in my business to realize this.
I was doing too much shit in my business that didn’t excite me or wasn’t fun to work on. The irony I didn’t realize was that, as soon as I quit my job, I would still dislike that 1, 2, or 3 hour project every day. So why bother?
The way I sort projects now in my business, and even what new projects to start, is one question:
Which of these is the highest intersection of natural excitement, and revenue potential?
That now occupies 1/3 of my total work day, which is called my “Zone of Genius” section. This is a concept from Gay Hendrick’s book The Big Leap.
Lesson #9: Your Business Will Kill You (or Fail) If the Rest of Your Life is Already Out of Balance
One of the biggest lessons was, in retrospect, the most obvious.
Entrepreneurship is one of the most mania/depression inducing experiments you’ll ever conduct in your life. Having said that, the more volatile the rest of your life is, the more likely it’s going to stress you the fuck out.
Here’s what I mean.
If your romantic life is out of whack. If your marriage is on the rocks, if you’re not so happy in your relationship, or if you’re pre-occupied with finding a person, building a business is going to be that much harder.
Because when you have a fight with your girlfriend or your boyfriend, and you go home, you can’t sleep, you can’t even function at work the next day, you can’t concentrate… how are you going to dedicate three hours to something you aren’t even 100% committed to?
If your health is on the rocks. If you already have acid reflux, sleep issues, anxiety, or something else going on, these will probably all get worse.
If you’re thinking about moving, or aren’t happy where you are. If every day you debate moving to New York to get out of <your generic town you think is small> that’s going to take up mental bandwidth and wear on you. Definitely.
If you’re already really unhappy. Entrepreneurship either will make no difference, since life already sucks, it will stress you the fuck out, or it may inspire you – because you now have some light at the end of the tunnel.
Fortunately for me, I had all of these situations going on at the same time. I had just fallen in love with a girl, and was dealing with the first six months of really high highs, and low lows (uncertainty).
I was having insane back pain.
I had moved back in with my parents, after living abroad.
I had no idea what I wanted from life, and I had almost no friends back at home.
I wanted to move every day.
I was miserable.
So every one of these little, nagging emotions, occupied mental bandwidth. Rather than trying to have 95% of my mental space available for my business and day job, I only had 30%. 20% went to my back hurting. 20% went to living at home. 20% went to figuring out where I wanted to move and what I wanted to do with my life.
And 10% went to whining like a little bitch because I was unhappy.
Imagine if I had 95% capacity to hustle?
Every little thing that’s already not working in your life will only make this process more complicated. I don’t say this to scare you, I say it to encourage you to fix those things first. Or at the same time.
Lesson #10: It Usually Takes Longer Than You Think
One of the most frustrating aspects of building anything is that it usually takes longer than we think.
Bill Gates has a quote that goes:
“Most people overestimate what they can do in a year, but underestimate what they can do in ten years.”
I suspect that building a business is the exact same.
The first 3 years for so many people, even really successful people are brutal. If you’ve read Shoe Dog, Phil Knight talks about how little revenue (profit) they really had even in the first ten years of their business. It’s insane to think that Nike made $30 Billion dollars in 2015.
And yet, throughout the biography it seems like years and years elapsed before they actually had any traction.
How long has Nike been around?
Since 1964 – 50+ years. Pretty insane right?
For me, after reading all these bullshit case studies about making “six figures on the first launch” I had high hopes.
I knew, without a shadow of a doubt, I would quit within six months.
Well, if you’ve read Milk the Pigeon, you know the real story.
I went through about six jobs while I had my side hustle going. I kept quitting, thinking I could “burn the ships” and never once did I successfully do that. So I got another part-time job. On and on and on I repeated this.
Every time I quit, I had reached my mental breaking point and didn’t want to keep doing what I was doing. I was always so hopeful that I could finally. fucking. quit. for. good.
And then when I went into a new job, it was always half-assed, because I was so fucking angry and bitter.
What I wish I would’ve done is simple.
I wish I would’ve come up with a core metric – say, $2,500 a month – that I could live on, without stressing.
And I wish I would’ve committed to playing the long-term game, being okay if this process took me six months or six years.
And then committing to all the long-term game things:
- Building a business I love
- Not burning myself out
- Following the energy metric
- Taking good care of my health along the way
- Staying happy
- Taking vacations
Even though I did all these things (without burning out, completely), I didn’t have a long-term mindset. I didn’t think, “this might take years, so pace yourself.”
Because then, when you get there, you won’t acquire a head of gray hair, 30 extra pounds, and a short fuse because you worked yourself into exhaustion.
That’s one thing I wish I would’ve done way differently.
Lesson #11: Your Friends and Family Will Hate You – Once You Make it.
About six months after I had just started my business, I bumped into an old high-school friend in a cafe where I was doing some work.
He asked how my “website” was doing in a sarcastic tone.
“Great dude, on my way to earning my freedom,” I said.
“Well, just don’t quit your job too soon man,” he said.
When I said that I was making jobs with my business, he said, “Oooookay, Obama.”
Now that I have the life that I want – these kinds of comments have only gotten worse.
Especially when your friends and family find out about your income, they begin acting weird, like wolves that have smelled blood. People will call you selfish for not giving them money.
“Wtf? I’ve worked nights and weekends while you were watching Netflix, why should I give you money?”
People will say, “well, aren’t you lucky!”
“Are you fucking drunk? Have you seen the 145 nervous breakdowns I’ve had privately in the last three years because of my business?”
People will say, “do you think your stuff is really that good?” when they see that it’s flying off the shelves.
“I’m not sure, but did you see the work I put into it?”
Family members will make snide comments about “how nice it must be on the other side of the tracks” or “how easy life must be for you.”
“Every time you were sleeping or watching TV, I was working, asshole.”
Of course, I saw this coming a mile away.
I’ve talked about why people will hate you for being successful, many times before.
And more often than not, underneath their vitriol, there’s just sadness. They wish they hadn’t given up on their own dreams so easily. They wish they had worked harder. They wish that over the last ten years they chose growth instead of complacency. They wish that they kept going on the things that mattered.
And most of all, they wish they hadn’t given up so easily.
And so they take it out on you.
And it’s okay.
Because you shouldn’t give up so easily.
Even if you don’t do it for yourself, or for your family, or for that person or kids you love, you should keep going.
In a world where 9/10 people don’t go after those “little stirrings” inside them, you need to be that one person who does.
In a world where people would rather cut the tall poppy, you need to be the brave one who decides you’re going to grow as big as possible.
And in a world where most people are too afraid to blaze the path forward, you need to be the leader who is.
Because the world needs more leaders who have the fucking guts to walk their talk, and commit – UNTIL – they arrive at their goals