Category Archives: Personal

Seeking Rejection Immunity

Ask most people in the startup community and one of the most important characteristics, if not the most important, of entrepreneurs is resilience. Resilience in the face of competition, loss (financial or otherwise) and everything else that makes this whole thing a roller coaster. Personally, I feel the only way to really build up resilience is to become immune to rejection.

Lessons from the sales track

Sales never came easy to me. In fact, when I first started my career I loathed those who decided to choose it as their career path. Mind you, my father who I have more respect for than any other human being in my life, has been in sales for over 40 years. For whatever reason, I’ve always seen sales as being something of evil. Either way, I quickly got over that and learned what sales is all about. I now love it, but it took some time.

The most defining characteristic of sales that I’ve learned is coping with rejection. Once you understand and more importantly personally feel that most sales pipelines only convert something like 1% of their leads (not real statistic, but probably pretty damn close) then and only then, can you understand how much rejection is required to successfully convert. You get comfortable with it and finally realize it’s just part of the game. It get’s easier though.

Rejection sucks

The real problem is that the feeling of rejection sucks. If I look back at my life, it’d be hard for me to recount the number of times I was rejected for something. Girls. Jobs. School. You name it. Everyone gets rejected for something. And yes, even some of the most successful tech people in the world were rejected at some point. It sucks and getting over it sucks even more.

Startups get rejected all of the time

I just recieved an email rejecting our startup for an incubator. Possibly for the first time ever, I shrugged and said “meh”. Here’s another person who doesn’t believe in us. Great. Should I get an excel spreadsheet to count the number?

For anyone who has applied to YC, you’ve probably seen the all too familiar email from Kirsty Nathoo that begins “We’re sorry to say we couldn’t accept your proposal for funding.” Ya, we’ve seen it 3 times. Ever sent an email to a potential investor and got no response? Ever sent an email to a potential customer and no response? Yup, been there; done that. It sucks.

What keeps me going

I started reading frequently about 5 years ago after my first startup failed. When I say frequently, I mean a lot. Blogs. Books. Everything. Consume, consume, consume. Every day, every spare hour. I wanted to learn everything about why I wasn’t successful. Why weren’t my amazing ideas (vetted by my mother) making me the next Gates? What became widely apparent was that everyone of these uber successful people was an absolute nobody at some point. They faced rejection. They faced loss. The reality is, not one of these paths are identical in their shape, but their themes are largely consistent – rejection. Then once on top, rejection appears almost non existent. When I finally groked this, rejection came a lot easier.

We’ll continue to glorify successful tech entrepreneurs, but fail to fully appreciate the resilience these people must have had when building their companies. That’s something I plan on not taking for granted.

This is My Story


I’ve been wanting to write this for awhile. I’ve always wanted to write more about who I am, what I’m doing, how it’s taken me this long to get here. It hasn’t been until recently that I’ve felt more confident in sharing this with more people. For some reason I have no problem telling people in person, but when it comes to the internet, I think I can act quite “shy”. I’ve stopped myself from writing this for so long because I see it as bragging, but for every time I tell someone about the steps along this journey, the only feedback I’ve received has been “tell me more”.

So here’s more.

We all dream of success. We all hear the stories of how successful people act and how successful people behave. We constantly are trying to find patterns so we can mimic this ourselves. The reality is that every successful person has their own story. We like to put Bill Gates and Steve Jobs in the same sentence, but if you know about both of their backgrounds, their stories are astronomically different. My story is about pursuit. It’s the pursuit, the drive, and the ambition which I constantly fueled by that entices me. What will happen tomorrow? Do I have enough money? Why aren’t I rich yet? Whoa, I’m still single.

So here is my story. Continue reading

Tearing It All Down

In October of 1871, a fire swept over Chicago and killed hundreds and destroyed about 3.3 square miles. To give you an idea of the impact of how much of the city this affected, here is a map of the area affected.


It cost an estimated $3billion (in today’s dollars) to rebuild the city. We see disasters, either natural otherwise caused by humans, that can completely tear down systems, leaving people to rebuild them. Just look at cities such as Berlin and Warsaw that were rebuilt after large destructive forces tore them apart. One of the defining characteristics that I’ve noticed that separates a city like Chicago from a city like NYC (I’ve lived in both by the way) is that Chicago is cleaner, generally more efficiently mapped out, and more habitably than NYC. I believe this largely has to do with the fact that Chicago had the opportunity to be completely torn down and rebuilt because of the Great Fire.

I suspect, like all big cities, Chicago had a lot of problems previous to the great fire that lead to non-advancement of the city. Like most cases this is usually due to bureaucracy, politics, and corruption. But, it’s amazing the energy people will put into something when they’ve suffered a great loss.

Why am I talking about the Great Chicago Fire on a tech blog? It represents everything that is happening in today’s tech world. We are seeing a massive trend in creative destruction as being the norm to creating new business models, tearing down old ones, and generally as an advancement of our culture.

In 1998, an informal group called Mozilla set out to rebuild Netscape Navigator’s source code from scratch. Some people would argue that rewriting source code from scratch is the worst decision you can make, but judging by the success of Mozilla and the death Netscape, I think we can all agree that this has bee a good thing for us consumers.

I look back at my former employers and I see instances where destroying the company might actually be a good thing for the advancement of it’s mission, it’s employees, and ultimately it’s customers. But, as cognitively biased as we are, we are incapable of destroying our own selves, or doing nothing at all. Which often is the case in decision making, whereby doing nothing may actually more productive than trying to do too much. Our brains are wired to think that we always must do something, rather than nothing, and that creating a loss can never create a gain.

So looking at today’s system, both human and technical, we see the everlasting cycle with the following behaviors:

  1. New system gets built, people rejoice!
  2. Someone breaks system, so system adapts and get’s updated
  3. System get’s too clunky because it tries to do too much, losing the interest of its members
  4. People leave system and create new one

There are some exceptions to this, such as 37Signals. They deliberately let customers grow out of their system.

We’d rather our customers grow out of our products eventually than never be able to grow into them in the first place.

As I’ve decided recently with my life, I’ve tore all of what I had established down and am rebuilding. But it doesn’t mean I forgot the important lessons I’ve learned in building the professional I sought out to do 7 years ago.

No, Tweets Aren’t Your Own

It’s fairly common practice to put a disclaimer in your personal profile on Twitter, Facebook, personal blog, etc. explaining that all of your opinions “are your own”. This is basically another way of saying “I wanted to publicly state that these opinons don’t reflect on my employer, and therefore I cannot and should be penalized at work for having these opinions”. I was a victim of falling under this assumption as well. After awhile I began to think about the ramifications of our public opinions on our professional lives.

Let’s set up an example to illustrate my point.

Example – Jim is in the marketing department of a large ad agency. He’s never been accused of badgering other employees for their ignorance in the office, but generally he gets frustrated from time to time because they don’t get work done on time for him. Most of his co-workers don’t know this because Jim is generally pretty good about not showing his frustration. After a bad playoff loss he bad mouths a member of his favorite professional basketball team’s lead player on twitter telling him “You’re the worst shooting guard in the league. I hope you die”.

Let’s take some perspective on this. Let’s say this person had an excellent resume. Would you hire this person? If he was your employee, would you fire this person?

When I’m hiring someone, a big factor in analyzing someone’s character traits is how they handle situations where problems occur. In this case, our friend ‘Jim’ has displayed two sets of characteristics both inside and outside of work. So, the question I would have in the back of my mind for Jim is – if the pressure is on, is Jim going to blow up like he did with the professional basketball player?

Let’s take this a step further to the real root of the problem. Many employees of large (and small) businesses, who disagree with their employers actions, tend to use the public domain as a soapbox for venting their frustrations of their employers decisions, whether deliberately or subtly. This is largely due to the fact that there is no medium or forum for said employees to express their frustrations within their work space.


Contradictory to my sensationalized headline, tweets are in fact “your own”, but only in the sense that you are the one that created them. Hence why I put large quotations around “your own”. Once you have unleashed an opinion into the public domain, it becomes property of the public domain. This is powerful. Many people (including myself) have used the public domain as a means to bolster your status positively, but conversely it also means there can be equally negative consequence. Putting a disclaimer up doesn’t negate this.

What this is ultimately doing is forcing businesses to be much more transparent with their employees with strategies like the use of open-door policies and internal social networks. In other words, don’t piss of your employers, and don’t piss off your customers, and everyone will be happy.

Marketing Works and I Feel Sad

I, like most technologists, believe in the ideal that those with the most merit should benefit the most. Also, probably like most meritocratic believers, it means that merit and merit alone will get you ahead. Sadly, I’ve found this largely to be untrue.

I recently wrote an article on my blog here that garnered a lot of attention. It was called “Increasing Productivity is a Load of Bullshit” This article had the following characteristics:

  • Poorly written/edited (there were grammar errors)
  • Very hyperbolic
  • Elicited a variety of emotional responses (“ya I definitely agree!” and “You’re an idiot”)
  • Reached the frontpage of Hacker News
  • Resulted in roughly 6,000 pageviews (which far surpassed any article I’ve written)
  • Had evidence to back up some of the theory (but not enough)
  • It was probably the shortest time I’ve spent writing an article.

I felt very weird after writing it. I don’t regret writing it, nor do I dispel the themes in it. But, I learned something very valuable about today’s information-packed world – marketing is as important, if not more important today than it ever has been. Dually, the most effective marketing techniques are those that exploit our brain’s system 1, or automatic system. The problem is I don’t see the merit in this, but it works, and it makes me sad.

To take this a step further, I believe this largely has to do with heuristics and our mind’s natural biases towards processing information. We do so many things that don’t follow logic and I believe this largely is due to our brain wanting to use it’s system 1 as much as possible. The theory, as stated in Daniel Kahneman’s “Thinking, Fast and Slow” is:

Many people are overconfident, prone to place too much faith in their intuitions. They apparently find cognitive effort at least mildly unpleasant and avoid it as much as possible.

This theory can be taken even further to say that system 1 uses a lot of less energy and therefore the brain tries to be efficient as possible with it’s energy consumption. Ultimately, I think this whole concept makes me feel sad because it feels like exploitation and therefore triggers a negative response for me. But, hey, it works, right?

If you’re interested in this topic, here a few good resources: