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20 Lessons I Think That I Kinda Might’ve Learned About Entrepreneurship

The term “burning the ships” comes from the legends of conquerors past who would supposedly burn their ships upon sailing and arriving in a distant land as a symbolic way of showing that there was “no going back”. When I checked out of my W2 job for the final time last August 1, I’d been a business owner for years. But now, I was finally “burning the ships”. Everything changes when you go full time and your business becomes “the only thing” instead of “a thing”. I hope that you find these lessons interesting, and perhaps even learn a thing or two from them.

  1. Your job as a CEO/Founder is to solve problems. Problems are the norm. Do not be surprised when they come up. If you are easily rattled by things going wrong then you should not own a business.
  2. Running a small company can be lonely. I recently did a deal with a buddy because I thought it would be fun to work with him. I didn’t need him to do the deal and I could’ve done it on my own and probably made more money. But guess what? ROI isn’t the only thing that matters. You need to have fun and work with people you like if you want to avoid burnout. Disclaimer: You still need to make sure you’re working with the right people.
  3. Hire for personality/willingness to learn, not “talent”. Talent doesn’t matter if you don’t show up or aren’t willing to learn. Remember, in the age of information you can learn basically any skill, sales script etc on the internet. The part you can’t learn is work ethic or reliability.
  4. Time freedom is awesome, until it isn’t. I have a ton of flexibility to take cool trips, work on passion projects (like this blog), workout, etc. It’s awesome and I wouldn’t trade it for the alternative in a million years. But sometimes too much free time is a problem. Filling my time with things that bring me fulfillment has been a challenge. I’m going to keep working hard on this one.
  5. Motivation only gets you so far. Eventually you fall to the level of your systems. Everyone is fired up right when they start their business. Long term, you cannot rely on being “fired up” all of the time. If you notice tasks that you are slacking on, you need to hire and outsource them ASAP.
  6. Don’t expect rational or unethical people to suddenly start acting rationally or ethically. I’ve always been someone who likes to see the good in people. I still give people a chance and always go with the “carrot” before the “stick”. If the carrot continuously doesn’t work, learn to use the stick. In real estate, the stick is generally a lawsuit. I’ve been involved in VERY few, but it needs to be a tool in your toolbox when diplomacy fails.
  7. Someone else doing it 80% as well as you is better than you doing it yourself. You will never scale if you are working in instead of on your business. And you’ll be pleasantly surprised when you find people who are actually better than you at the thing you thought only you could do.
  8. No one is going to care about your business as much as you do. You own the company. The people who work for you don’t. This doesn’t make them bad people or bad employees. You would feel the same way if you worked for them. Get this in your head ASAP.
  9. You don’t need to be “innovative”, you need to repeat the same boring shit over and over. Calling sellers and analyzing deals every day isn’t new or glamorous, but it’s what generates revenue. Buying a new CRM, software, list etc is just periphery stuff you’re doing instead of doing the main thing.
  10. Your personal brand matters. You don’t need an IG, website etc from day one. But I would start posting content from your deals ASAP if you aren’t already. If I could go back I would’ve created my social/website much sooner.
  11. At the same time, if you have no deals you have no need for a website or social media. I’ve seen people spend all their time making a business card, website, social etc while having zero revenue. You don’t need any of this stuff. You need a product and a customer.
  12. Don’t conflate “hiring” for “growth”. I hired a bunch of people right off the bat. None of them work with me anymore. Hiring the wrong people is worse than hiring no people.
  13. Don’t hire people who are “dabbling” or who are looking for a “side gig”. I mean this as no disrespect to the people who did this with my company. I think they would agree with me. You need people who are “all in”. And they needed to be “all in” in order to succeed.
  14. It’s more important to make A DECISION than the PERFECT decision. You are going to make literally hundreds of decisions a week as a business owner. Quickly analyze, decide, and live with the results. Optimization can be the enemy of productivity. I can’t run a real estate business while spending days agonizing over which bathroom vanity to put in a particular house flip.
  15. Check your ego and keep learning. I learn stuff from 25 year olds, I learn stuff from 70 year olds. I learn from people I’m farther along than, and I learn from people who are farther along than me. The “I’ve got it figured out” attitude will limit you. Act accordingly.
  16. At the same time, you can’t listen to everyone. Block out the guy selling you the bullshit 20k “proprietary course” on IG who’s never done a deal. You’re also going to need to learn to block out friends and family from time to time.
  17. Learn what the sunk cost fallacy is, and try to find ways to avoid it. If a deal is a dud, get out of it sooner than later, even if you lose money. Dragging it out is only costing you more time, money and energy.
  18. Get used to signing the back of checks instead of the front of them. At a W2 job, you can more or less count on the same amount of income arriving at the same time on the same day every week. In business, you need to get used to large amounts of money both coming and going from your account. If you can’t handle cutting checks/wires for large amounts of money, you should be at a W2.
  19. There is absolutely nothing wrong with a W2 job. I’m trying to state this in a way that doesn’t sound douchey or like I’m claiming I’m “built different” (as the kids say). But business ownership is not for about 99% of people. It works for me. It’s also a struggle at times for me. But I wouldn’t go back. That doesn’t mean that the same path is right for you or that you’re “not betting on yourself”, “trading your time for money” or whatever other BS “entrepreneur Instagram” is feeding everyone today.
  20. You’ve got to learn to enjoy the grind. People are going to drive you insane. Jobs are going to get done incorrectly. Things are going to go wrong. You have to take all of these as learning experiences, and not as the end of the world. Smile sometimes. Learn to enjoy your wins, and perhaps more importantly, learn to see value in your losses.


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