It’s Never the Right Time

It’s never the right time to…

  • Have a baby
  • Take that trip
  • Go work out
  • Start a business
  • Apologize to an old friend
  • Go back to school
  • Call your mom
  • Move to New York
  • Change careers
  • Write a book
  • And on and on…

Inertia is the great enemy. Gotta fight it and make life happen anyway.

The Best Enemies are Overt

I find it much easier to overcome obvious and specific opposition.

For example, if someone straight up tells me I can’t do something I become motivated to prove them wrong.

It’s well documented that many super successful people had mediocre childhoods. I don’t want to draw too many conclusions but I’d be surprised if that opposition isn’t a big part of their motivation to succeed.1

These types of enemies are great motivators because they are impossible to avoid.

But what about indirect enemies that aren’t so obvious?

For example, complacency. Or inertia. Laziness.

These things don’t talk to us. They don’t tell us we’re losers. They’re just… there. Almost like a tax or a body part. Always in the background but never in our mind unless we specifically focus our attention on them.

My point is that I believe these attributes can become very motivating enemies if we take the time to remind ourselves of their existence.

Who wants to be lazy or complacent? Put a sticky note on your computer that just says “you’re lazy” and, maybe, you’ll be scared into being a little less of that thing.


  1. Naval Ravikant has a great theory that goes something like “every winner, deep down, is a loser.”

Be Suspicious of Epiphanies

We’ve all had that moment watching a movie or listening to a great song where we just feel so… inspired!

I can accomplish anything!” 

Maybe we write down some goals and tell ourselves that, yes, this is the time when everything changes.

The reality of course is that these moments are fleeting and almost always wrong.

They can even backfire, because when we inevitably don’t live up to our new expectations we blame ourselves. We feel guilty and assume we’re flawed.

Big life changes are slow and require fundamental changes in behavior. They’re like a big boat… they take a ton of time and effort to change direction.

Instead of big epiphanies we need little actions. Do a little something today. A small change on the direction of a boat’s rudder today can have a huge impact on where it ends up.

What’s helped me is to expect a little failure. I mentally tell myself there will be times where I don’t live up to my own expectations, and that that is okay. I remind myself that even the most successful and ambitious people in the world have bad habits they want to break.

The worst thing that can happen is to lose momentum and let 1 tiny failure turn into 10 consecutive failures. By expecting some failure, you give yourself an emotional pass and prevent yourself from self-destructing and failing those extra 9 times.

Learn to Code to Start a Business?

One of the mistakes many aspiring entrepreneurs make is to view companies solely through a product lens: a company is its product first and whether it succeeds or fails depends on the quality of the product.

This happens because:

  • Media focuses on product (e.g. “The New iPhone Killer”) and not the “business side” (e.g. strategy, competitive moats, etc.)
  • Founding myths that glorify the “ah ha!” moment
  • One of the most-admired companies of all time, Apple, is a product-based company
  • Y Combinator’s motto, Make Something People Want, speaks to the product lens they’ve instilled in the founders they back.
  • Developers have been empowered by a (very good!) trend the last 15+ years: the cost to build a product has become so cheap that there are new products everywhere. There’s even sites like ProductHunt to help early adopters identify good new products, because there’s so many to sort through.
  • Companies can’t talk as much about their operations/strategy as much as their product, often for competitive reasons. Or it’s just boring.

And now that so many products are being created, we’ve convinced ourselves that making a product is the same thing as making a business.

It’s not.

Obviously you have to have a product to have a business, but it’s just a part of a much larger whole:

  • Finding customers
  • Convincing them to buy from you, today
  • All of your finance department: invoicing, collecting, accounting, payables
  • Servicing your customers
  • Hiring and managing
  • Everything legal
  • Vendor relationships
  • Raising capital (if you think that’s a good fit)

The point I’m trying to make is that if you want to be an entrepreneur, learning to code is a good skill but not the only thing that matters. And so if you can do the rest of the business stuff, especially at the beginning when the company is just a few individuals, you’re going to be really valuable.

You’ll Fit Right In

One of my favorite parts of the US is this: by looking at someone you can’t tell if they’ve been in the US for 7 generations, or whether they just got here yesterday.

When I lived in Mexico it was obvious to everyone that I wasn’t from there. 100% of the people who met me assumed I was a foreigner (correct) who didn’t speak Spanish (incorrect). They’d ask me about George Bush and politics in the US (“why can’t more of us go to the US?”). All these built in assumptions.

Not that I was offended by any of this. Their assumptions were mostly correct!

But in America good luck asking someone about their “home country” politics before finding out where they’re actually from. Even if the person is an immigrant, which country precisely do you think they arrived from?

And that is what makes this one of the great narratives of America; come as you are from wherever you are, there’s a place for you here. You’ll fit right in.1

Unfortunately it seems fewer people than I realized think this way. Or maybe they’ve been temporarily tricked. I’m not sure, but it makes me sad.

  1. New York City is the best embodiment of this ideal. I’d argue that NYC is America smashed together and viewed under a microscope. People from everywhere, made of a thousand colors and speaking a hundred languages. That you can come to the US and, if you choose, still find a neighborhood of people who look like you and talk like you is also a good thing.


Casey Neistat had a major film career well before YouTube, but he became a Big Deal once he started daily vlogging on YouTube in 2015. 1

His storytelling is what makes them great. He turns an average day and boring tasks into something with a plot: a beginning, middle, and an end.

This video is my favorite example, and IMO one of Casey’s most underrated videos.

Humans are hard wired to learn from stories; the better we can get at storytelling, the more influence we’ll have.

  1. He did over 600 consecutive daily videos before stopping.

Do Something Today

Something I’ve wondered about the CEOs of medium to big companies is how do they know they’re working on the right things?

Like, how does Brian Chesky know that his todo list for Monday March 21 is the right stuff?

The obvious answer is that… he doesn’t.

How could he? For a company of Airbnb’s size, the market won’t give you feedback until much later.1

And the bigger you get, the longer you have to wait.

How long had Jeff Bezos and Amazon worked on the Fire Phone before it launched? Before they decided to kill it? Think of all the time and brainpower and effort spent on building a phone that was a remarkable failure.2

But even if you’re small or an individual it’s still hard to get quick feedback. How do you know whether what you’re working on today will help you get to where you want to be in 3 to 5 years?

The only solution3 is to accept that it’s really hard to know whether you’re going in the right direction.

The best answer I’ve found for dealing with the feedback problem is to focus less on the long term and instead do something today. Like, right now.

I’ve seen various forms of this online:

“‘Always produce‘ is… a heuristic for finding the work you love. [This constraint] will automatically push you away from things you think you’re supposed to work on, toward things you actually like. ‘Always produce‘ will discover your life’s work the way water, with the aid of gravity, finds the hole in your roof.”
How to Do What You Love, Paul Graham

“Be not afraid of moving slowly. Be afraid of standing still.”
– Chinese proverb

What happens when you do a little something every day

“We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten.”
– Bill Gates

The gist is do something today. And tomorrow. And keep that going just a little at a time until you look back and you’ve climbed the mountain.

  1. One of the joys of programming is that you get near-instant feedback on whether your code works.

  2. Incidentally, the Fire Phone is also a killer example of how amazing Amazon is. Lesser CEOs would have let the project languish even while it was obviously not succeeding. Instead, Jeff Bezos ruthlessly and unemotionally ended the product just barely over a year after it launched.

  3. In my opinion, but that should obviously go for everything on this site

You Do You

How many arguments could be solved and how much condescenion could be avoided by just saying “hey I wouldn’t do it that way but you do you.”

Raise venture capital vs bootstrapping?
You do you

Fast food vs cook at home?
You do you

Bay Area vs New York City?
You do you

Merry Christmas vs Happy Holidays?
You do you

Entrepreneur vs corporate life?
You do you

Emigrate vs stay in home country?
You do you

Have kids vs no kids?
You do you

Gay marriage vs traditional marriage?
You do you

Outbound vs inbound marketing?
You do you

Go out vs stay in? (okay, this is more of an internal debate…)
You do you

Game of Thrones vs The Batchelor?
You do you

LARP-ing (Live Action Role Playing) vs playing sports?
You do you

Vegetarian vs eating meat?
You do you

50 Shades of Grey vs Pride and Prejudice?
You do you

Smith & Wollensky vs the local buffet?
You do you

Some of these are obviously more serious than others, and some of them aren’t even mutually exclusive, but the general idea is the same.

Let people be.

You can follow me on Twitter here

Don’t Risk What You Need for What You Want

Long-Term Capital Management (LTCM) was a hedge fund that performed well for a few years in the 90’s but then lost $4.6 billion (90%+) in a matter of months.

The fund was managed by the creators of the Black-Scholes formula for valuing options. Super smart people worth hundreds of millions of dollars.

By over leveraging themselves for more potential gain, they put themselves in a position where it was possible (no matter how unlikely!) to go broke.

Warren Buffett gave a great, quick talk about this you can watch on YouTube (especially the bit starting @ 2:30):


“You only have to get rich once”

His point is that once you’re rich, don’t put yourself in a place where it’s even remotely possible to become not rich.

He uses a fantastic metaphor of a gun with a million chambers and a single bullet loaded in one chamber: no matter what someone offers you to put the gun to your head and pull the trigger once, you shouldn’t take the bet. The downside is just too damn high.

That’s the kind of bet the managers of LTCM made.

They risked what they needed for what they wanted, and lost big.

The Power of People Who Aren’t Like You

I’ve been reading a terrific book called Messy, by Tim Harford. It details the ways that being tidy/neat is overrated, and the various ways that having a “messy” life can help us both personally and professionally.

One of my favorite chapters so far is about collaboration and diversity.

It cites a piece of research that was really troubling. A group of researchers challenged groups of students (4 people per group) to solve a murder mystery:

“In some cases the groups comprised four friends — members of the same college fraternity or sorority. In other cases, the groups were made up of three friends and a stranger.”

It won’t surprise you since the chapter is about diversity that the groups which included a stranger performed better. Okay fine, but also…

“The problem comes when we ask… how well the members of the group thought they’d done.

Members of diverse teams didn’t feel very sure they’d gotten the right answer, and they felt socially uncomfortable. The teams made up of four friends had a more pleaseant time and they also tended to be confident–wrongly–that they had found the right answer.

Yikes. So the teams that did better felt worse and vice versa.

You might ask why non-homogenous groups tend to perform better: the author says it’s because we’re less likely to question and push back on people who are similar to us.

It’s a weird mix of groupthink (“I innately trust these people to make good decisions because they’re similar to me”) and valuing the relationship more than solving the problem at hand.

This is true of my own experience. Discussing ideas and problems with people who aren’t like you is uncomfortable and non-linear. You don’t know where the discussion is headed, and it’s hard to tell whether you’re on the right track.

You often have to dig deeper to the foundational facts to have a good conversation, which can feel unsettling.

Which of course is the entire point.

This was just a single story in this one chapter. The rest of the chapter details a bunch of other ways that we’re more homogenized today: we live by people like us, we marry people like us, we work with people like us, we hang out online with people like us, and on and on.

And this is happening in the age of the Internet, when we have access to a wider diversity of ideas and people than ever before.

I’m going to try to meet more people who aren’t like me.

Speaking of which, we should meet on on Twitter