Five Reasons To Be More Transparent With Your Investors

This is a re-published piece of mine, initially published in Forbes.

One thing that has struck me as interesting for quite some time, and especially over the last several months, is the hesitation that exists within us all to reveal uncomfortable information. Whether it has to do with an everyday company decision or a compounding, lingering strategic issue, leaders often refrain from shining a bright light on challenges when communicating with investors.

Clearly, the objective is to either preserve “character” or delay reality. However, shying away from a problem ultimately destroys both.

Facing challenges head on is by no means an easy task. Based on my experience, both positive and negative, below are the five ways you can challenge yourself to always be transparent, and why they are important.

It Builds Credibility and Trust

Transparency establishes trust over anything else. Whether it be within the context of a personal or professional relationship, the more straightforward you are, the faster you and your partners become comfortable with one another. The same is true with your investor partners. The most profound indicator of integrity and respect is the willingness to reveal the uncomfortable things. The generated trust then leads to expedited resolution, a win for all involved. I like to send out a monthly update to our entire investor base with most of our metrics, regardless of whether they’re good or bad, to further nurture this trust with our partners.

It Emphasizes Team Cohesiveness

Facing the uncomfortable things leads to blood, sweat, and tears. And a team can either really come together or it can crumble. When we face problems at Smack that we don’t have an immediate solution to, we bring it to our investors’ attention. Stating the issue saves everyone a lot of time and positively channels everyone’s energy. Plus, the benefits are worth it: more time spent discussing the actual issues, and less time dancing around the elephant in the room means more “team training” for everyone involved.

In our case, both internal and external partners get to spend more time seeing how certain members respond to certain complexities, what certain characters’ buttons are, and so on. This leads to more cohesion among the company’s leadership and our investors. Our lead investor graciously offers to take time to meet every three weeks to touch on the most burning of issues. In the early stages, push your external partners to meet more often than not.

It Constantly Keeps Your Team on Their Toes

If you know you are operating in a transparent environment, then you also know that any shortcomings will immediately come to light. Having this urgent mentality keeps you and the rest of your team on your toes, with no pause.

This goes for external partners as well. Knowing the depth and frequency at which we dive into strategic issues with our investors forces me to constantly ensure that our team is on our A-game. Transparent teams want to capitalize on every single opportunity and strive to squash every problem as quickly as possible. If investors know you operate on an aggressively transparent basis, it will force them to operate at their best.

Although we do not have an investor on our board just yet, we still go through the motions of having a formal board-type meeting every two months or so. It forces us to not only set ambitious yet realistic milestones but also to prepare us for operational scale.

It Maximizes the Probability of Getting the Right Help at the Right Time

The more known everyone’s problems are, the higher the probability that you will receive a lending hand. Years ago, when I hit a roadblock or needed help I would have been ashamed. This was all insecurity. Over the years, I’ve come to realize that when you are able to lean on other intelligent people you are able to accomplish so much more. Today I leverage my teammates and investors more than ever by letting them constantly know what keeps me up at night. 

It Trains You to Accept Failure

There’s nothing worse than not admitting defeat or accepting wrongdoing, not because it gives people the perception that you’re not confident, but rather because it slows down the rate at which you receive feedback and subsequently the rate at which you learn. No matter how successful you or your business may be, feedback is the most powerful tool in becoming better at your craft and leading those around you. The more transparent you are, the more feedback you will receive. Always push your teammates and yourself to give and receive feedback. 

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

Don't be afraid to "do you"


Lately I've been tested a bit more than usual, in many different ways, mostly professionally, relative to my business. The same business that also happens to be one of the most important journeys that I am currently on, professionally-- to change today's high school media, for the better, through the use of technology. 

To some, this journey may be a business, it may be a job, it may be a sport, or it may be a relationship, but ultimately, it's all the same. It's essentially something that you've embarked on, without looking back. It's something that throws challenges out at you consistently, some tougher than the others, and it's something that makes you question your very own intuition, day in, and day out. 

These challenges sometimes make you question whether what you are doing even makes sense. They sometimes make you feel so uncomfortable and put you in a tight squeeze, such as having to decide whether to leave your family behind and move for your job, or such as having to decide whether or not to change the whole direction of your business for a potential partnership, or such as risking your whole college career on a sport. On top of it, these challenges even sometimes overflow into your personal life and start affecting many other things, besides your professional journey. 

Well today, take it from someone who has been tested professionally, and sometimes as a result, personally, to always remember to follow your intuition. No matter how daunting it sometimes may be, or no matter how much you may get tested along the way, stick with it.

Do not ever sell yourself short, and do not ever give in to someone telling you that you are crazy for doing something. I don't care what it is that may be taking you away from your intuition, whether it be a potential business opportunity, whether it be your boss doing things in a way that you don't agree with, or whether it be a friend not looking out for your best interest, always remember to believe in yourself.

Speaking from my own personal experience, I can tell you that following my intuition, no matter how many times I've stumbled along the way, both professionally and personally, has made me who I am today. It has allowed me to become a better person with myself, my colleagues, and with my friends, with every day that goes on. So make sure, if you already do not, starting today, to follow what you believe in, and let yourself become a better person as a result of doing that. Do what you want to do. Not what you "think" you should be doing, or what others "think" you should be doing. After all, you know yourself better than anyone else. Plain and simple, don't be afraid of what others think of you, because most of the time, worrying about that won't make you happy at the end of the day. I know if I listened to most people around me along my journey (not all, but most), that I wouldn't be where I am today.

Moral of the story: in every aspect of life, do you.



Best Friendship

Hello all.

I know I promised everyone many great, inspiringly abundant posts to come back when I started this personal blog in September, however, as many of you are aware of, I did hit an unexpected turn in life. On September 23rd of this year, this world lost a very beautiful person, who happened to also be one of my dearest friends.

I decided that despite the sensitivity of the subject, I would share my thoughts with the rest of you, as I truly believe they may collectively serve as meaningful insight to those who may have one or multiple best friends. 

Such a simple concept-- a best friend. With such a simple concept, comes simple, and sometimes loose, definition, right? With this very same loose definition, comes a profound lapse in the everyday understanding of what a best friend, and therefore a best friendship, does for you and your life as you move forward.

Depending on one's age, or stage of life, the definition of a best friendship, and what it does for the one in question, varies. One might say that a best friend is someone to always complain to. One might say that a best friend is someone who they can go out drinking with. One might say that a best friend is someone that they can go to when all else fails. The list goes on.

What I say, after almost three full months of genuine reflection, is that a best friendship is much more than all of that previously mentioned, and more. It is all-encompassing, more than you would ever think. Many believe that their education, their work, and their self-efforts are the best preparation for the battles of life-- but it's actually quite the contrary. Rather, best friendship prepares you for the battles of life, all of them, more than anything else, whether you realize it or not. It prepares you for your education, for your professional life, for your significant and insignificant other relationships, for your successes, for your failures, for your current and future family, and for your eventual happiness. 

A best friendship unconditionally nurtures you, no matter what the circumstances may be. A best friendship unconditionally pushes you and challenges you to do good, no matter how much that may disservice you. No education, no professional work experience, and no self-effort can ever amount to the unconditional push that a best friend will serve as. 

Ultimately, at the end of the day, the meaning behind a best friendship, regardless of the definition, or regardless of the stage of life one is in, is all the same. When you really take a step back to thoroughly understand what a best friendship does, you come to realize that it is not so simple at all. Instead, it is quite phenomenal. It is one of the beauties of life that cannot be purchased, that cannot be learned or taught in school, and that can certainly not be fabricated. 

So today, and everyday moving forward, I challenge all of you to embrace those who you may view as your best friend, whether it be your child-hood / adult-hood peer, your close or distant relative, significant other, etc. Treat them and prioritize them as much as you prioritize your profession, your education, or your self-effort. Embrace them for all that they have done for you, both directly and indirectly, and for what they will continue to do as the future comes.

Invest time in your best friendship(s), regardless of how tough things may be, regardless of how busy you may be, regardless of how rich or poor you may be, and regardless of how well you think things may be going for you. When you are at a loss for motivation, stop what you are doing and realize that it may be a phone-call or text message away-- your best friend. Because after all, this element of life, this concept of a best friend, is not so simple at all.

- G

Failure: Why such a negative connotation?

Failure: Why such a negative connotation?

I was with one of my good friends the other day and the topic of “failure” came up as we were engaged in some random conversation with this couple that was sitting next to us. It’s important to note that shortly before this conversation, my friend and I ironically touched on the same topic not even an hour earlier.

One of the two from the couple asked me, “what is it with start-up people and this whole Silicon Valley mentality of failure being a good thing?” This question immediately struck me not only because it was something that I could directly relate to, but also because it made me realize that “failure” is often times perceived to be this black hole that no one should ever venture off to-- it’s quite the contrary, we experience failure every day of our lives. The reality is that every single person on this Earth, no matter how rich or how poor, no matter how strong or how weak, and no matter how intelligent or how ignorant he or she may be, experiences certain facets of failure throughout the duration of his or her life. The other reality that many people disappoint is how big of a role failure has played in making them a better person and in bringing them closer to accomplishing their goals and dreams. It is not success that we learn the most from, it is failure.

Let me digress and use myself as an example. I proudly admit to having failed at many times throughout my life. The aspects of failure that I refer to, in my case, range all the way from significant matters such as business and serious personal relationships, all the way to insignificant matters such as misplacing personal belongings and forgetting to call a friend back. Everyone fails, and believe me, it’s completely fine.

The reason why failure, when presented, is fine and should be embraced is because it allows you to become a better person. Failure means that you have now been given an opportunity to learn and therefore, by learning, an opportunity to come closer to success, in whatever aspect of life you may have failed at in the past. Instead of ignoring failure, or being ashamed of embracing it, I instead urge all of those who read this to accept it at all times. Allow your failures to be a part of your story, as that is what makes up your character at the end of the day, and as your character will serve as your foundation as you continue to truck forward. This foundation, which should be stronger subsequent to learning from your failures, will enable you to work harder and more intelligently at achieving your life-long goals, both professional and personal, and ultimately afford you with becoming a better person.

Failure isn’t so bad after all huh?

- G