It’s hard to believe that I’ve been out of college for 8 years now (granted I checked out mentally about three and a half years before that). Regardless, having been at this whole “being a businessman” thing for a while now, here are 8 things I’ve learned in the past 8 years that I think could be helpful to anyone at any stage of their career:

  1. Always offer to pick up the check. While it’s definitely great to be known as the guy who always pays, you most certainly don’t want to be known as the guy who heads to the bathroom just when the check is supposed to arrive. Nobody wants to go to dinner with that guy, and therefore nobody wants to do business with him either. The more often you reach for the check, the more people will remember what a great meal they had with you, and that will pay dividends at some point. The general rule of thumb I go with is, if it’s obvious that the money being spent on this meal probably means a lot more to you than it does to me (think interns, small startups, early stage entrepreneurs, college students, etc.) then I’m always going to pay for that meal, no matter how hard you fight me. Conversely, if I’m going to lunch with a billionaire hedge fund manager, while I’m still going to reach for the check, if he insists on paying, I’m not going to fight very hard. But if I did end up paying, I’d feel pretty good about having picked up a billionaire’s check!
  2. Make people feel that they work with you, and not for you. This isn’t very easy to do – most employees feel like you are their superior, and that they should fear you. It takes a special kind of leader to get his troops to believe that they are in battle alongside of him, and not behind him. You do need their respect, but you don’t want their fear. Teammates should want you to be on their team, and not look at you as this guy who just so happens to control their paycheck. I always cringe when an employee introduces me as their boss to someone – it means I haven’t been doing my job very well.
  3. Offer your time to those who need it, and expect nothing in return. At least 10% of my time each week is reserved for people who need my help with something, and 9 times out of 10, there is absolutely nothing in it for me. Could be an entrepreneur looking for feedback, or a college kid looking for the meaning of life. Doesn’t matter. I receive all sorts of cold emails every week, and I’ll at least offer 15 minutes of my time to hear someone out and offer them my pointless opinion if they want it. I get nothing out of it, except that I hope that someday, something that I said will help that person, and they will remember me. There’s a great story about a holocaust surviver named Sandor Teszler who once caught an employee stealing from him – instead of calling the police, he simply told security that the man would no longer steal from them, and to let him go. Many years later, Teszler’s entire family was captured by the Nazis and being beaten in a concentration camp. The man in charge of the beating was none other than the former employee who had been forgiven by Teszler. He remembered the kindness he had been shown, and saved Teszler’s entire family by getting them out of the camp via the Swiss embassy. Teszler could have never known all those years before, that the simple action of forgiving someone, would end up saving his entire family’s life.
  4. Don’t be penny wise and pound foolish. While being frugal has its place in startup lore, at some point, you don’t want to be known as the guy who is too cheap to pay for a CRM, leaving your sales team to track their deals on a spreadsheet. A penny saved is exactly that – a penny. So spend within reason, and make sure everyone is comfortable. You don’t need the Four Seasons, but you also don’t want the Red Roof Inn. The Hyatt is probably a good compromise. The rule I try to operate with is that anyone who is traveling on behalf of our company will always be more than comfortable, and will eat very well. Anything less would be a poor reflection on me, and I’d be embarrassed to be known as that guy.
  5. The Ritz Carlton is a great place to meet people. Every time I travel for a big event like the Final Four or NBA All Star Weekend, I always make it a point to hold court at the Ritz Carlton.  You don’t have to stay there (see point 4 above) – but you want to grab a table in the hotel lobby, order yourself an iced tea, and start catching up on your work. The only thing more certain than death, taxes and the San Antonio Spurs, is that important people stay at the Ritz, and you can network the shit out of that lobby if you care enough. About 50% of all the money I’ve raised has come from people I’ve met in fancy hotel lobbies. About 5% came from a chance encounter at the Playboy Mansion. You do the math.
  6. Communicate clearly, and in a timely fashion. I cannot stress enough, how important it is to be able to clearly articulate yourself in person, and over email. As I often tell people, in the past 4 years, I’ve raised over $60M for my company and my fund, entirely on the back of my ability to write succinct emails – I literally have no other skills. I just communicate clearly, and make it a point to not only respond to every single email that I receive, but to also do so within a day of receiving said email. Most of the time, I try to get to inbox-zero before I go to bed, which means that if you email me before midnight, there’s a pretty solid chance you’ll get a response from me the same day, regardless of whether I know you or not. Even more important, and perhaps this is just a pet peeve, is proper grammar. If you write me an email and you don’t know the difference between their, there and they’re or your and you’re, then it’s really hard for me to take you seriously. It’s really not that hard to learn the difference – it’s simply a matter of caring enough about the little things. I would be mortified if I wrote an email to someone, and I used a “to” instead of a “too”. Spend a minute reading what you write, before you hit send, and fix your damn grammar. You can thank me later.
  7. It’s not just who you know, but more importantly, who knows you. There is pretty much nothing that is more of a determining factor of success in this world, than the extent of your network, and what people think of you. There is a less than 10% chance my company would still be running and that I’d also be running a venture fund, if I hadn’t walked up to random people and told them what I was working on 3 years ago. There would be less than a 5% chance of those things happening if I was also a complete asshole. The more people you know, and the nicer they think you are, the more likely it is that people are willing to introduce and recommend you to others. If you’re a complete dick and then you ask me to warm intro you in to a company for a job, do you really think I’m going to risk my reputation with the other founder? Nice guys finish last is just a stupid myth.
  8. Perhaps most importantly, the craziest thing I’ve learned in the past 8 years, is that if you really want something bad enough, you absolutely can and will have it. I learned this first when I gate crashed Michael Jordan’s 50th birthday party. Since then, I’ve also gate crashed his 51st, 52nd and 53rd birthday parties – by now you would expect that I’d be on the invite list, but I’m really not. I just find a way to sneak into the building every year, and it’s because I just really want to be there. Although at this point, it’s really just an annual tradition. I really wanted to work in sports, and not have a shitty 9 to 5 in a cubicle on 5th avenue – now I have 2 of those jobs, running a sports analytics company and a venture capital fund that invests in sports related companies. The universe somehow comes through if you really really want something. So go out there and tell the world whatever it is that you want – just make sure you use proper grammar if you’re writing the universe a letter!