The Maybe Game

Something’s been bothering me lately.

I’ve been hearing about the following situation from a bunch of people: a set of entrepreneurs really wants to get funding from a specific VC. The entrepreneurs meet with the VC a number of times, yet they continue to get nowhere in terms of funding progress. And it’s very frustrating- it’s consuming a significant amount of time from the entrepreneurs that they simply can’t afford to waste. I just want someone to tell them to bail on that VC and look for another one. I can’t understand why they keep going after this specific VC. Don’t they know that they have an amazing product? There are so many other VCs out there that would be willing to fund them.

Well, if only it were that easy. No one wants to give up on their dream VC, especially when they lead you on enough to the point where it seems as if they’re truly interested. What happens is – and here’s the problem – on meeting number one, when the VC is asked whether or not they are interested in investing, they respond “maybe.” And that is the single worst answer a VC can give to an entrepreneur.

See, when an entrepreneur meets with a VC to get funding, there are only three possible responses to their pitch- yes, no or maybe. If they get a “yes” right away, then they’re very happy. They’ll obviously have to continue to put in effort to ensure that the “yes” remains a yes, but they can go on with peace of mind knowing that something good will eventually come out of their meetings with the VC.

A “no” is not desired, but it’s still good. The VC is doing the entrepreneurs a favor- he is telling them, “Look, I don’t want to invest in you. You’re not for me. Move on and find somebody else.” It’s a disappointment for an entrepreneur to hear that, but it still gives them closure that they shouldn’t be wasting their valuable time chasing after a VC that they’re not going to get.

But if an entrepreneur gets a “maybe,” then they’re in trouble. The entrepreneur is now unsure as to whether or not the VC is truly interested. The VC wants to keep meeting with the entrepreneur, continuing to lead him on, but the entrepreneur can’t tell if it’s heading in the right direction or continuing to go nowhere. And because the entrepreneur is unsure, he will continue to put in effort to try to convince the VC that his product is worth investing in. The entrepreneur will put in tons of effort to show the VC their best stuff and give them their best info. Yet at the end of the day, the VC may have zero interest in the entrepreneur at all and is just using them for information and amusement.

It’s funny because if another VC jumps in and offers to invest in the entrepreneur, then all of a sudden the game changes. Demand increases, which in turn creates a higher valuation for the product. Now the original VC wants to invest. And you know what- that original VC may be screwed. The company now has more options – perhaps even better ones – that they have to pay attention to. And you know where that extra time commitment is coming from? The “dream” VC’s time. The entrepreneur has likely already learned not to waste his time with that original VC because their meetings are just creating more excitement for a happy ending that is unlikely to occur.

For all those VCs out there who are part of the “maybe” crew- do entrepreneurs a favor and just tell them “no.” It won’t break their hearts, and they will in fact respect you even more. They’ll be satisfied that you have told them the truth up front and that they can now move on. They liked you – they really did – but it simply was not meant to be. It hurts a little, but they’re grown men- they’re confident that they’re a gem and that they’ll be able to raise funding elsewhere.

But if you’re a VC that’s truly torn between investing or not investing, make up your mind. If you really like the entrepreneurs, why not take the risk with them? You have the potential to build something amazing. Commit to them before they commit to somebody else.

Being Selfish with Time

It’s crazy how quickly time goes by.

And that’s not necessarily a bad thing- time flies when you’re having fun, they say. Yet it’s great to sit back once in awhile, think about where you are and what direction you’re heading in, and then slow things down. Too often I see people get so caught up in something – whether that’s their schoolwork, job, relationship, etc. – that they don’t even set time aside for personal exploration and accomplishments. And to me, this is very unfortunate.

I know this may seem like a crazy question (especially if you’re around my age), but what’s your goal in life? And if that question is too difficult to answer (which it should be), then narrow it down to your goal for the next year or two or ten. I know my goal is to accumulate as many experiences as possible. You may think “experiences” is vague and can include just about anything, but that is literally how I want it to be translated. I’d like to experience – to feel, achieve and understand – as many situations and emotions as I can.

And that’s not limited to just the good things in life- the bad, tough experiences are the ones that make you stronger for the future. To give two (mediocre) examples: rejection from a job earlier in the year led me on the path to find my current job, which I couldn’t be happier with. In a more physical case- surgery on my shoulder motivated me to get stronger to prevent injury again, and I now feel like I’m in the best shape of my life. And besides for the motivation factor, having these “tough” experiences makes you appreciate the great ones even more- you stop taking them for granted. And the great experiences are the ones you need to make time for in your life.

Great experiences translate to great memories, which to me are worth far more than anything else- they’re priceless. I still get chills when I think about basketball tournaments won with my best friends, or graduating high school alongside my classmates, or bonding on spring break with my fraternity brothers, or the annual family get-togethers on Thanksgiving.

But what I’ve come to realize is that, as you get older, it becomes increasingly more difficult for these experiences to occur naturally. I feel myself seeking them out, more so now than I did when I was younger. And this makes sense- I have more responsibilities now, as I’m sure you do too. You probably have to balance some combination of school, a job (or two), a relationship, fitness, and family. Outside of those commitments, how much time (and energy) do you really have to go out and have those unforgettable times with your friends? How many opportunities do you have to truly explore your interests? Deep down, do you feel like you’re getting a fair shot at accomplishing your personal goals? If you don’t like your answer to any of those questions – and you’re not alone by any means – then I suggest you sit back and re-think your day-to-day.

Time flies by- and it is too short to sacrifice your personal goals. For once, be selfish. Follow your gut. Explore your options. Pursue your passions. Tally up accomplishments. And most of all- don’t look back. It can never hurt to be experience-rich.


Being Selfish with Time

Is Taking a Risk Really Risky at All?

A few weeks ago, I was on the verge of crashing my first party. Techstars Demo Day had come to an end, and the NYC tech community was set to celebrate that night. (For those of you who don’t know what Techstars is, it’s an incubator in Manhattan that essentially acts as a parent and mentor for start-ups). What was amazing about this party was the fact that the guest list included anyone you’d want to meet in the tech / VC / entrepreneur community. What wasn’t so amazing was the fact that you needed a personal invite to be on this guest list- and needless to say, I didn’t have one.

Standing outside in the cold, I had a decision to make. I was faced with two options: One was to call it a night. This seemed safe. Reasonable. Easy.

The second option: Try to get in. This seemed daring. Impractical. Risky.

So I began to think- what does risky mean? What was so risky about this situation that made me so hesitant to attempt to enter the party? And if there was risk involved, what were the implications of taking such a risk and failing? As I thought about all of these questions, I began to wonder: Why am I – and people in general – so fearful of risk?

When you look in a thesaurus, three common results for “risk” are uncertainty, unpredictability, and insecurity. To me, there is an underlying context that enables all of these feelings to occur- and that is imminence.

What is imminence? To quote (from my own work), I wrote in a paper last year that:

“Imminence is about anticipation. It's that moment in time when there is complete suspense, when everything else besides the imminent ceases to exist. It can be the turning of a page of a mystery novel, the soaring of a basketball through the air just before the buzzer sounds, or the scene of a horror movie that keeps you on the edge of your seat. It's the instant when nothing's definite, nothing known fully. The imminent is unpredictable- its end result can be delightful or devastating, fulfilling or disappointing. It is this uncertainty about the imminent that causes us to be insecure- and we all fear insecurity."

So if imminence is the reason we all fear risk, how can we conquer that fear? We must conquer the imminent. And how do you conquer the imminent? You must pursue it. That’s right- to conquer the imminent you have to experience it. It might sound counterintuitive, but tell me, what’s the worst that could happen?

If you fail, what have you lost? I can tell you what you will have gained- a ton of knowledge and experience. If you believe pursuing something could be a waste of time, what do you define as a waste? To me, meeting lots of new people and trying to do something different is as fulfilling as anything else I would otherwise be doing.

Overall, my mindset is now guided by an underlying principle: I would rather do something and fail than never do it at all and always think to myself “what if.” Think about it: If you fail or make a mistake, you will undoubtedly learn and grow from it. But if you never try something at all – especially something you backed out of because of the “risks” associated with it – then there’s a chance you may be saying “what if” and regretting that decision for the rest of your life.

Now ask yourself- is THAT a risk you’re willing to take?



Is Taking a Risk Really Risky at all?

The Power of Context- Why we're not so different from the iPhone 4

“Iphone on Verizon is massively better than AT&T.”

To most people, that Chris Dixon tweet probably seemed irrelevant, nothing more than a random thought from the co-founder of Hunch. But to me, there was something more profound about what he had said.

Here was the same exact phone with identical settings, yet something had changed, externally, that completely altered the iPhone’s internal capabilities. In one moment, it went from an underachieving device to a super-phone. And all that changed was its network.

Lately, I’ve come to realize how important the concept of a ‘network’ truly is. You always hear about “networking” and “leveraging your network,” but how many people actually take those words to heart? There are many extremely bright people out there who have amazing GPAs to go along with triple majors, double minors, specializations, and a spot in the many ‘exclusive’ clubs that anyone can sign up for. Don’t get me wrong- those are all important and will definitely present students with some excellent job opportunities. But what most people don’t realize is how important their network is- for their present, near future and the long-term.

My gameplan before the semester was that of a quintessential business-school student: I would work hard, do well in school, get some solid internships for my resume, and then kill it when it came time for recruiting and interviews. More specifically, I wanted to be an investment banker. Why? Because I’m in NYU Stern, a school that surrounds me with students who are mostly interested in becoming investment bankers (surprise, surprise). It wasn’t even like I had a choice- it seemed to me like it was either i-banking or failure. But then something changed…

Over the course of winter break, a friend recommended that I take a class titled Entrepreneurship for the New Economy. At first I had no interest at all for a few reasons (it’s not towards my major, goes from 6-10pm, easier A’s out there, etc.). But after a lot of convincing, I decided to just do it.  And it has changed my life forever.

Why? The class material itself is great, but that’s not what makes it special. What makes it special are the people I’ve become surrounded by.

Each week I am fortunate enough to hear from one or two of the top entrepreneurs in the city. I’ve been given opportunities to interview at some amazing start-ups and VC firms. And on top of all that, the course itself is taught by two Managing Directors at two of the top VC firms in Manhattan, Larry Lenihan and Hilary Gosher.  Those are all incredible people to add to your network. But to me, what makes the class even more special is the caliber of students I am surrounded by.

How do you define “networking”? From what I’ve seen, most people think of networking as trying to build a relationship with only those people who are more accomplished than they are. For example, if you attend one of those career fairs, what do you see? Huge lines of students only looking to speak to employees from each firm. Is it important to know these people? Absolutely. But what I’ve discovered is that peer-to-peer networking is even more important.

The people I’ve met over the course of the past few months have taken me to another level. Two months ago, I had no idea what my future held. I had just turned down an internship for the summer because it was not for an investment banking position. I was so narrow-minded at that point that I had no idea what venture capital and entrepreneurship even meant. But today, I am actively seeking to participate in both of the aforementioned communities. And I have to credit that to the new network I’ve become a part of.

I learn more from the 3-4 hours I spend in my Entrepreneurship class on Wednesday nights than I learn the entire rest of the week. Just speaking to some of the students - including my teammates on a project called TripScore - I learn about what’s going on, what the new trends are, and what people are interested in. Furthermore, when you start to see the people around you passionately pursuing their dreams, don’t you think it will motivate you to take yourself to the next level? I know it has for me.

In the past few weeks alone, I have worked on TripScore with my classmates, met with multiple potential co-founders for another project, and spoken with Owen Davis of NYC Seed (one of the most insightful / enjoyable meetings I’ve ever had), all while working 20+ hours a week at PrivCo, a start-up I began working for about a month ago. Busy? Yea. But it’s probably the most fun I’ve had since starting NYU over a year and a half ago.

Speaking of NYU, I have to give credit where credit is due. Many people believe that their education (whether it be at NYU or another university) is not nearly worth the pricey tuition they pay. Do I think the education alone is worth it? I’m not sure. But I can definitely say that a classroom education shouldn’t be all you’re getting out of your university. Included in that tuition value is not only your education and the “brand name” of your institution, but it’s the whole experience that you have the ability to partake in.

What is included in that experience? The caliber of professors and guest speakers, the caliber of opportunities you are presented, the caliber of conversations you can have at any moment with anybody on the street, and last but not least, the caliber of your fellow students and the value that they add with their opinions, criticism and overall feedback. All of these external surroundings are what make up the true value of your college experience. You may think that you’re just paying for an education and a brand, but there’s a whole lot more value to school than that. All you need to do is look and you’ll find it.  

Fortunately, I have discovered this while I still have plenty of time to maximize the value of my experience. As a sophomore, I have just begun to take the initiative to expand my network and get more involved in the tech / entrepreneur / venture capital community. My only hope is that other students begin to realize this too, because the opportunities at hand while you are still in college are too great to let slip away.

If you place yourself in the right context, you’ll be surprised at the amount you can accomplish, and even more surprised at how much fun you’ll have doing it. Students, and people in general, must take advantage of their surroundings and networks, because they can take advantage of you and exponentially improve your capabilities.

Hey, it did wonders for the iPhone.