One of our investors, Ben Li, keeps a private wiki for his portfolio companies. It is a place where we can ask questions, have discussions, and just exchange ideas.

As I was going through my backlog of emails today, I came across an email from him about one such discussion.

It said:

Subj: Diaspora Co-Founder Ilya Zhitomirskiy passes away at 22 

Hi TK,

I hope you are very well always.


When your time allows, you may share what you think about it in the wiki. Thanks.

Ben Li

I had no idea someone had passed away in the startup community. That too, someone so young.

Truth is, I probably missed a lot of things over the past few months as I’ve been heads-down building the business.

However, over the past few weeks, I have been thinking hard about how I can be more present even while running my business.

I achieved a lifelong dream in 2011: I’ve been able to focus my time on one thing, one product, one company.

It’s always been about college + startup, or day job + side project, or consulting projects + startup dream. And then, in 2011, I was able to ramp down on everything but Tout and it felt great.

Working Non-Stop Does Not Scale

However, to somewhat of a surprise, it came with a huge responsibility. It meant that while before there was a forcing function governing how much time I had on something and away from something, there was nothing there now.

To make matters more extreme, even more forcing functions went away when I moved 3,000 miles away from my friends, family and wife and set up a space in Mountain View to live+work 24/7 on Tout; even worse, I managed to convince Derek to do it along with me.

It felt amazing at the time, and needless to say our efforts paid off in many different ways to get us to where we are today.

However, only a few months later did I really realize the downside to doing such things.

I felt burnt out, pulled in different directions, living on a plane straddling both coasts, moving forward on a product to get the next group of customers while keeping our current paid customer base happy.

I think only idiots think that Startups are actually easy. I knew that none of this would be easy.

In fact, to the contrary, I knew this would be hard.

Anyone I talked to reiterated that this would be hard, that there would be pain. And I think that is probably what made me ignore my own pain and made me keep forging ahead.

At the end of the day though, this doesn’t scale.

And with startup founders everywhere trying to iterate fast and build businesses that scale exponentially are in fact, ironically, doing it all in a manner which does not scale. 

Any successful startup takes 18+ months for a medium sized exit (non acq-hire) and at least three years to become an overnight success. 

I came to this realization about two months ago and since then have been spending a lot of my time simplifying my life. No more bi-coastal team. No more straddling both coasts. Less hectic, more zen. More focus, less open threads.

Bottom line? Take It Easy.

What it means to “Take It Easy”

Sure, I know what you’re thinking. “I saw your tweets TK, you worked through Christmas on that Year In Review thing, this post is bulls*it.”

Not quite.

There is a method to my madness. What I’m suggesting by “Take It Easy” is not to go all “lifestyle business” on your startup; but what I’m suggesting is to keep the biggest picture in mind as you’re killing yourself to build your company.

As I reflected over the last 15+ years of me being an Entrepreneur (both in traditional businesses and in high-growth startups), I’ve tried all different ways of working.

100 hour work weeks, multiple projects/jobs at once, and even this past summer where I lived and worked in the same space. After having tried these different things, I’ve come to believe in two key principles to reach peak performance:

Principle #1 – “Time away is just as important as time on the job”

Being completely engulfed in one thing almost always is a disaster.

It almost always diminishes your perspective, makes you lose sight of the goal and most importantly gets you to reach a local maximum at best.

So the next time you think you’re adding value on your 80th hour on the job — think again.

Principle #2 – “Choose one thing, don’t end up neither here nor there”

This one took some time to figure out for me but I think is quite profound. On any given day, you’re going to have a million things you HAVE TO AND SHOULD get done, but in reality you’ll probably get three of those things done.

That is just a matter of reality.

The worst thing we do as entrepreneurs is ignore that reality and try to accomplish it all. Where that leaves us is the dreaded “neither here, nor there” state.

You accomplish nothing, you’re stressed at the end of the day, and worst of all, you lost a whole day only to feel the same way the next day.

You’re neither here, nor there.

I think for cases like these, the best thing to do is to embrace reality and choose the one thing you’re actually going to do.

And yes, that 1 thing could very well be to go to the beach, because you’re tired and burnt out and you really can’t produce anything better.

This is hard. But that does not mean it has to be painful. Let’s be present in this beautiful moment we’ve all been given as an opportunity to change the world and let’s do it without killing ourselves in the process.

Take it easy.