6 Things No One Tells You (But Really Should) About Starting a Company

There are two types of people in this world: those who want to know and those who’d rather not know. This post is for the people who want to know.

Imagine we’re at the doctor’s office, and you’re informed that two patients are going in for the same surgery today. On one end of the waiting room sits the patient that has a notepad and pen in hand. This patient has many more questions to ask the doctor, before the procedure actually begins. She wants to confirm that she fully understands every single detail — big or small— about what’s about to happen to her while under the knife.

Then in walks the second patient. She checks in, flips through a couple magazines, quickly gets changed, and when escorted back to where the surgeon’s waiting, simply says, “Give me the funny gas Doc, and let’s get this party started!”

This blog post isn’t for those people; the one’s diving headfirst into life’s experiences, trusting that everything will “just work out.”

This blog is for the people out there who bring their notepad and pen to the doctor’s office. It’s for those who like to get as much information as possible before committing to anything. These people find comfort in having clear expectations, so they can feel more prepared to handle what’s coming next (or simply decide to opt out altogether).

So if that sounds like you, and you’re thinking about taking the plunge into entrepreneurship, continue on. If that’s not you, though, that’s totally OK. Get back out there and keep experiencing things for yourself! Hopefully, I’ll see you back here on Monday for my next post.


So you’re the ones with the notepads and pens. Well, hello there. It’s nice to meet you. Below I’ve outlined six things that no one tells you, but really should, about starting your own company. I share these things with the intention of telling as much truth as possible, so that you can feel equipped to make the decision that’s best for you.

1) You’re going to suck at being your own boss (at first)

People think that if you’re your own boss, you’ve made it; you’re living the life everyone dreams of. No clocking in and out for you. No reporting to anyone else. No one telling you what you can and cannot do. There’s just absolutely nothing standing between you and what you want to do. Ahhh…isn’t that the life!

Sure, it’s cool. I get it. I really do. I’ve been there before, and some could say I’m in that position right now. But what a lot of people won’t tell you is how much work you’re going to have to do on yourself, in order to become the type of person that can actually run a successful business. Leaders of successful companies don’t just happen; they’re made.

People who go into business for themselves are opting out of a 9–5 and into the “whenever, wherever, however” business of getting sh*t done. They no longer have the luxury of reporting to work on Monday to receive a set of pre-determined assignments from a boss. They are the boss, and being the boss means you have a whole new set of responsibilities. As the CEO, it’s up to you to decide what needs to get done, by whom, and by when. It’s up to you to make the “big” decisions, and make sure those decisions are the right ones, as often as possible.

As the leader of a company, you have to be constantly thinking about others: your employees, customers, partners, investors, advisors, lawyers, accountants, etc. It’s one of the most challenging (and rewarding) pursuits you can undertake: trying to become an exceptional leader. And there’s no room for cutting corners or cheating. Any progress you make, any success you achieve, it has to be fully earned through a lot of painstaking work…day after day, month after month, year after year.

All in all, being your own boss requires an incredible amount of discipline, sacrifice, and dedication. And that takes time to perfect. Just know that you’ll probably be working on perfecting that skill your entire life, because as your business gets more complicated, so does learning how to operate it. It’s a never-ending process of work and personal development.

2) You will have a breakdown (at some point)

Identify problem

Research

Plan

Strategize

Build

Prototype

Validate

Network

Recruit

Position

Onboard

Manage

Develop

Test

Iterate

Solidify product market fit

Fundraise

Scale

  1. Highlight everything in the list above.
  2. Copy and paste it directly below the first list.
  3. Repeat this process 10–100 more times.
  4. When done, you will now have a sense of what you’ll have to do, in order to build a successful company

It’s a lot, right? Yes, I know. Being a founder is INCREDIBLY HARD!!!! (I hope all those exclamation points really help drive that message home.) It’s so difficult, in fact, that it is absolutely normal and OK to feel overwhelmed by all the pressure to get everything done, and get it done as quickly as possible, with as few mistakes as possible.

Private breakdowns are extremely common in the world of startups, and are something you should know about, because when it does happen to you, you won’t have to feel alone. You’ll know that there are hundreds, if not thousands, of other aspiring entrepreneurs who sometimes struggle with managing it all too. Others who don’t have it all figured out all the time either. You’ll realize that this is just a part of building a successful business: doing incredibly difficult things; things most people aren’t willing to do.

Oh, but that’s not going to be me. I’m tough! I’ve always been a leader, and I’ve overcome incredibly challenging things already; I can handle this too. Okie dokie. Suit it yourself. Just please do me a favor and ping me on Twitter with a little smiley face, if you ever do find that I was right. Thanks :)

3) Your partner may leave you, and your family and friends may start to dislike you

Most everything you know as your life today will no longer exist once you make the decision to start your own business. Sleeping in, eating breakfast and dinner every night at home, dropping off or picking up your kids from school, making your Wednesday night softball games, meeting up with your friends every Friday for happy hour, keeping up with your book club, eating, exercising, and sleeping regularly, watching movie marathons on Netflix, making it over to your cousin’s for Sunday Football, taking a vacation…

Yeah, you can seriously kiss a lot of that goodbye. Starting a company means that you’re entering “Sacrifice Central,” and “making” it here requires that you change your life in some pretty significant ways. And while you make those changes, there’s a very high likelihood that many people in your life may not be a fan of those changes. They may not like having less access to you. They may say, Hey, this isn’t what I signed up for; this isn’t the life I thought I’d share with you. Just know that your decision to start a business will affect others in your life, so make sure you’re up front about that with them, and see if there’s a way you can all meet in the middle.

4) If you don’t know yourself now, you’re going to have a tough time

When starting a business, if you don’t have a good sense of who you are, who you want to be, and why you’re choosing this particular route to get there, you’ll be more susceptible to the rough elements of this industry. You’ll be more likely to get swayed, get pulled in directions you may not want to go, or easily get caught up in the noise and fanfare of it all.

What will be driving you won’t be grounded in a deeper purpose. And even if you reach your goals, once you get there, you’ll still feel empty. Even after all that hard work and sacrifice, you’ll feel empty because you still haven’t taken the time to figure out who you really are and what makes you happy. You’ll continue to numb yourself with work. You’ll keep your head down and you’ll keep trudging away, in fervent pursuit of that “next great milestone.” And when you get there, you’ll realize something: happiness isn’t there either. I’d better keep going. Maybe it’s at the next stop?, you’ll think to yourself. And on and on it goes like this.

So please, take some time to get clear on who you are and why exactly building a company is the best path for you. As with anything, you don’t have to have it all figured out in advance (i.e. you don’t have to see the whole staircase, before taking the first step), but you should at least have the initial conversation with yourself. You should ground your vision in things that really matter to you, things that matter to you on a deeply personal level. Because it is these things that will be your motivation to weather any storm, to overcome any challenge in your pursuit to bring your vision to life.

5) It will take you waaaay longer than you think

Founded in 1976, Apple really didn’t get on the map until eight years later when the Macintosh was invented. Ben Silbermann, the founder of Pinterest, quit his job at Google in 2008 to pursue his own startup. The first app he created was called Tote. It flopped, but he kept at it. He built another app called Pinterest and launched it in 2010. Three years later, its userbase grew to 25 million. That’s a total of seven years Ben was grinding it out, before making it big.

There are a lot of stories like this, and the point is: building a successful company takes time. Waaaaay more time than most people think. So whatever number you have in your head for the years it will take you to get where you want to go, you may want to double or triple that. Just remember, it’s not a sprint; it’s a marathon full of a lot of different types of sprints.

6) You will likely fail. Seriously, the odds are not in your favor.

Within 3 years, 92% of startups fail. Just think, if you and 99 of your friends all decide to start a business today, by the summer of 2018, all of you will have failed, except for 8. Only 8 people will still be out there fighting the good fight. Crazy, isn’t it?! Yes, but that’s the world of startups. Lots of big aspirations, but very few success stories.

And those few success stories are what keeps this industry alive. It’s the lifeline that feeds inspiration to the next generation of aspiring entrepreneurs, working tirelessly for their spot in the “Elite 8.” It’s what keeps many investors coming back, no matter how many bad bets they’ve made in the past. The success stories make us believe; make us believe that the impossible is possible, and that the risk is worth the reward.


For those that wanted it, I’ve candidly shared some of the things that you really can expect to experience if you decide to take the plunge into entrepreneurship. My intention is to simply inform. To let you see behind the curtain and into the crystal ball, so that you won’t be caught off guard, you will be able to prepare accordingly, and you can can decide for yourself if this is the right next step for you.

Either way, I wish you all the best.


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