Surround yourself with people smarter than you, and constantly take the uncomfortable route

It’s been some time since I wrote on a particular topic, and this is partially due to the fact that the past several months have been a roller coaster ride (literally), and partially due to just not giving myself enough self-reflection time.  

As you all know, I’ve been absolutely obsessed with working on my startup, SmackHigh, for quite some time now. To be honest though, it’s not just that I have been solely obsessed with working on Smack, but it’s that I have been equally as obsessed, if not more obsessed, with working with our team.

Our team consists of some amazing human beings who have not only become domain experts in their respective roles, but who more importantly also have an extraordinary aptitude curve and hunger to learn—some examples include a recent art-history grad who had 0 prior marketing/community experience and who now helps successfully lead our brand ambassador management, an MBA and self-taught social media growth hacker who can each A/B test the s*** out of any viral campaign and achieve optimal results, all the way to engineers of all experiences and calibers, one who is a recent graduate, and others who have come from the realms of Constant Contact and Twitter.  

Now, although our team may appear to be competent, it doesn’t mean that it is an easy team to work with, and more so it doesn’t mean I have become more comfortable in my day to day work. Working with such an incredibly talented cohort with a willingness to excel, consisting of various qualities and perspectives, is actually quite the contrary. It is an experience that is addicting, rewarding, and above all, very challenging. It puts you on to a ship that is constantly rocking back and forth, forcing you to be more alert than you ever have been before.

As our team grows past the general “everyone does everything” dynamic and into a more individually specialized role dynamic, I find that it requires an even deeper layer of consistent mental engagement from a founders’ standpoint, in which your view points and thoughts are constantly battled with conflicting opinions and perspective, which often times may prove to be with merit. When you go from making most decisions after one conversation, on a day to day basis just as soon as six months ago, to now having a larger team who is equally as responsible for those very same decisions, whether on a granular or general standpoint, it can certainly settle you into an anxious sense of feeling. You once thought you had all the answers, but you come to a sudden realization that you actually do not. You were once only proven wrong by your co-founders on a daily basis, but now you’re proven wrong by all of your employees as well on a daily basis. But to be frank, I wouldn’t have it any other way. 

In 2011 when I attended a closed invite entrepreneurial conference at Stanford, hosted by the Business Association of Stanford Entrepreneurial Students, I was fortunate enough to be a part of a small, tight-knit presentation workshop led by Marissa Mayer, who is currently Yahoo’s CEO, and at the time was still with Google as one of their earliest employees. At one point she told the story of how she came to choose to accept the offer to work with Google, which was a startup at the time, over the many other well established, top tier organizations who were recruiting at Stanford at the time. The advice she received from one of her professors, who happened to push her the most towards the Google opportunity, was to always make decisions that a) surrounded yourself with people who were smarter and more talented than you, and b) put you in the most uncomfortable position, as these decisions were typically the ones that would lead you to both professional and personal success.

This is exactly what has happened here with me, whether intentionally or unintentionally, by immersing myself within a team of equal, if not more, competence. This is what I encourage all of you to do, whether it be with regards to your personal or professional lives. Next time you are faced with a tough decision, embrace the tougher path and take full advantage of it. It may seem daunting at first, and you may not have it all figured out as to exactly how you will cope with the challenges that come with making such a decision, but I can assure you that it will be worth it in the end. You will trip, you will fall, and often times you will be thinking “what the hell did I get myself into?”, but above all, you will come out a stronger, more valuable individual at the end of the day—assuming that you take advantage of the position you have subsequently put yourself in.

The amount I have learned over the past several months and that I will continue to learn from our team is worth every second of having to reason through a particular problem, or come to a sometimes obvious conclusion. Why? Because it forces me to stop and take into account all of the different variables that are at play when working with other highly motivated individuals. By continuously going through the motions of considering the many variables that I never once considered, I have seen myself grown. Most importantly though, I have grown as a professional and as a person. I have matured, I have become more transparent than I have ever previously been, and I have become a more prudent human being— and none of this would have happened if I were not accompanied by the people who I am accompanied by today.

It all started though by surrounding myself with people who are smarter or more talented than me, and by putting myself in an uncomfortable position. So get on it.

- G