1. If you’re building a service business, the majority of your clients will expect you to go above and beyond for them, while doing the absolute bare minimum for you.
  2. Nobody pays on time. And the first time you learn that lesson, it’s not going to feel great.
  3. Firing people is the worst part of the job, by far.
  4. Every single employee you hire is going to want things nobody prepared you to give them, like a career trajectory.
  5. Once you’ve built a six-figure business, you realize how unimpressive it actually is (and you start to cringe at solopreneurs who start running Facebook ads talking about selling courses on how to build a six-figure company).
  6. Once you’ve built a seven-figure business, you also realize how unimpressive that is as well. The really impressive companies are the ones 8 figures and above, and that’s humbling to learn first-hand.
  7. When people say “nothing beats the highs of entrepreneurship, and nothing is scarier than the lows,” they’re telling you the truth. Unfortunately, you won’t have any idea how to fathom what those feelings actually feel like until you’re A) wide awake at 1:00 a.m. because some massive opportunity just came together and you’re wired out of your mind, or B) you’re lowering yourself into a hot bath at 3:42 p.m. on a Friday in an attempt to relax and get yourself to stop feeling like the walls are caving in.
  8. Even when you become profitable, you’re still in “startup mode.” Nothing is guaranteed. Ever.
  9. The amount of time you will spend in front of your computer will make you crave time away from any and all screens as much as possible.
  10. For the first year, year and a half or so, expect to sleep less, eat worse, go to the gym less, and barely touch your hobbies. Whatever semblance of work-life balance you think you’re going to be able to maintain that first year and a half of building a startup, you’re wrong. That said, you should still fight and try vehemently to get back to a place of balance as quickly as possible, because these are unsustainable habits.
  11. You will start to understand why 99% of people have no interest in becoming entrepreneurs and would rather just work a job they enjoy.
  12. You will learn the stark difference between a $30,000 hire, a $60,000 hire, and a $90,000+ hire.
  13. You will have weird, really weird dreams about your business and some problem your subconscious is wrestling with.
  14. Your circle of friends will be entrepreneurs and founders themselves, since they’re the only people who truly know what it is you’re feeling and going through on a daily basis.
  15. People in your life, even people you truly care about and are close to you, will have very little patience for your “problems.” They’ll see the aspects of entrepreneurship everybody talks about: freedom, being your own boss, etc. What they won’t see, and simply can’t see, are all the other challenges that come with those select freedoms.
  16. A “growth over everything” mindset can be exceedingly destructive for startups. Yes, there is such a thing as growing too quickly.
  17. Cash is king, and the moment your monthly payroll exceeds 2 months of runway in your bank account, you’re toeing a dangerous line—and your strategy needs to be to stack cash as quickly and efficiently as possible.
  18. “If you can’t measure it, don’t do it.” My mentor gave me that one years ago, and even though I had thought I’d understood its significance, this was a lesson I really only internalized very recently. I’ll say it again: “If you can’t measure it, don’t do it.”
  19. People don’t buy processes. They don’t buy ideas, or approaches, or plans. People buy results. That’s it.
  20. Do not underestimate the value of a manager. A manager can make or break your growing organization. A manager can mean the difference between you, the founder, working “in” the business or working “on” the business. Managers are how you scale, and how you pass off responsibility so that you can continue focusing on bigger and bigger items. Without managers, you will end up becoming an employee within your own company.
  21. Ideas are the easy part. It’s the execution of those ideas that separate decent companies from great ones.
  22. Competition is a good thing. If you have a competitor, or a handful of competitors, you can save yourself a lot of learning time by watching them closely—especially if they’ve been around a lot longer than you. Chances are, they probably learned their lessons the hard way, and there’s a reason why they do what they do, the way they do it. Use that to your advantage.
  23. As a company, it’s better to be magnificent at one thing than haphazard at 12 things.
  24. Raising money is overrated—and until you’re experienced enough as an entrepreneur, you honestly won’t even know what to do with it once you have it.
  25. When you’re neck-deep in the startup grind, you will completely lose all sense of time and space. No joke, there have been days where certain enterpreneurer checked his calendar to see what year it was.
  26. I know I’m biased when I say this, but I wouldn’t be preaching it if I didn’t believe in it so wholeheartedly: building your personal brand as the founder is one of the single most effective things you can do for your entire company. My personal brand as a writer online is how I’ve opened every single major door on my entrepreneurship path thus far: getting to attend exclusive events, bringing on Silicon Valley advisors, speaking opportunities, client introductions and inbound leads, the list goes on and on. Do not, I repeat, DO NOT, underestimate the power of putting yourself out there as the face of your company.
  27. All that said, starting a company is a lot like how I imagine it feels to start a family. And for all its ups and downs, it’s one of the most rewarding things you could possibly experience in life.
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