The Art of Waiting

And why it’s crucial in the early stage

We tend to picture entrepreneurs as relentless forces of nature. People who break through walls, never take no for an answer and change reality instead of accepting it. And rightfully so. It takes an extraordinary amount of persistence, energy & conviction to build valuable sh*t from scratch.

But it also takes a lot of patience.

Some walls require many attempts to break, you must often wade through numerous “no”s before receiving a fateful “yes” and most realities worth anything take years to change. The day-to-day of startups can be trying and involve a lot of waiting. This is something that’s not talked about nearly enough, so let me try to shed some light.

Waiting is generally attributable to three key startup realities:

• Everything takes longer than you expect.

This is especially true of early product releases, when tiny teams with limited resources are forced to constantly face two very intimidating forms of risk: concept (are we building the right thing?) and execution (are we building that right thing the right way?). On a weekly, daily, hourly basis.

• Most things require multiple people, and we’re all just so damn unique.

Save for the most technically brilliant and versatile founders, most startups require the skills and attention of multiple people. This may seem obvious, but it’s super important to realize how significant a challenge it can be. It takes time for teams to find chemistry, and things change quickly and often.

• You’re almost always the last item on people’s task lists.

When you first start throwing around an idea, it’s hard to get people’s time and attention. When you’ve got a first prototype or beta, it’s hard to get users. When you’re ready for your first hire, it’s hard to get your target to commit. And investors often go quiet for weeks before even confirming receipt of answers to their questions. (That took you hours to perfect).

• Until you’re not…

The great news is that the waiting doesn’t last forever. I’ve been lucky enough to see the tide change for a few of my companies and it’s pretty remarkable. All of a sudden, new users can’t try your product fast enough and existing ones can’t wait for new features. There’s nearly constant inbound interest from top-flight talent and you’re the one throttling emails from investors rabidly pursuing an allocation in your next round.

In all cases, a subtle but important step in this process is what I call the “art of waiting well”. And in many cases, this art is as much about avoiding mistakes as anything else.

Rule 1: Don’t get distracted.

Distraction can come in many forms: a competitor with a different take on the market, a consulting opportunity that pays well, a friend who just bought a new toy. But the single easiest mistake to make when frustrated with a relatively new idea is to prematurely fall in love with a newer one. Execution is never as simple as you think it should be. It’s always messy. And that’s why it’s everything.

Rule 2: Don’t mistake bumps for breaks.

There are a LOT of bumps on the path to building a great company. And they only get bigger the further down the road you get. The problem is that, because you haven’t felt them before, the bumps tend to feel biggest in the early stage. They almost never are. Don’t rush to judgments about your team based on hiccups with early product progress. The mistakes you make when stakes are relatively low in the early stage can form a valuable & shared foundation for your team going forward.

Rule 3: Know when it’s time to call a spade a spade.

Rule #2 not withstanding, the early stage is a great time to find and honor true self-awareness. Products are much more likely to change than people. Know your strengths, weaknesses and quirks. And pay attention to those of your team members. If you keep running into the same issues with the same people, speak up. These issues won’t just go away. And the longer things go without being addressed or resolved, the messier they get.

Rule 4: Make only the right compromises.

I’ve made a career out of testing ideas before engineering or automating them, but even I can tend to over-design and over-commit at times. In such cases, the easiest way to accelerate launch is to remove features and simplify your product. But this is a slippery slope.

A minimally viable product ceases to be viable once you no longer trust the feedback and data it generates. Simplify your product, but don’t loosen your standards. Remember, products are easier to change than people. We’re more stubborn than pixels and code.

Rule 5: Be ready.

This is pretty simple. The obvious necessity of constantly waiting on other people is to always be ready yourself. The best founders I know started with incredible hunger and humility. Respond quickly, try not to reschedule and routinely bend to the preferences of the people on whom you’re relying to bring your vision to life.

In fact, I’m up writing this blog post at 4:30 AM because this is when my dev team works. And I don’t want them to have to wait.

That’s my job :)