Are you a missionary, or a mercenary?

Choose wisely

Tell me, what else should I have done?
Doesn't everything die at last, and too soon?
Tell me, what is it you plan to do
with your one wild and precious life?

—Mary Oliver (The Summer Day)

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“I am not sure we are wired to ever be W2 employees again. Are you sure that is what you want?”

I’m sitting across from the Founder and CEO of a very successful AI company. We were introduced through a mutual friend, a well-connected executive in the NYC tech ecosystem, under the pretense that this was a recruiting conversation.

In a very short time, this CEO's company has gone from an idea to an impressive product and thriving business with multi-millions in ARR. They are at the beginning of a hockey stick growth curve in both revenue and employees. So while he’s hiring, and open to talking about potential roles for me on his team, he is more importantly pushing me.

You could work at Google for a while and live the good life. But is that what you really want?

As a founder who fought and lost, I sit with the question. What is it that I want? What is it any of us want from what we do?

Missionaries vs. Mercenaries

In my last post, I explored the sicknesses that founders suffer from. These include a lust for power, a hunger for fame, a thirst for authority, and importantly a greed for wealth and riches.

That post was about the dark side of entrepreneurship, which we don't talk about enough, and those difficult aspects of our personalities that drive us.

And while I do firmly believe that there is a sickness deep down in every entrepreneur, we also do what we do — founders, all of us — because our calling fulfills us.

When people ask me what I am passionate about, I always have had a simple answer: I like to build sh!t.

There are many ways people might answer this question. But for potential founders, the real distinction isn’t about whether you prefer building versus marketing and selling a product. Instead, the crucial insight lies in whether your response reveals a readiness to serve as a mercenary in someone else's army or a become a missionary in your own crusade.

Becoming a Mercenary

Here is the definition of a mercenary: primarily concerned with making money at the expense of ethics; a professional soldier hired to serve in a foreign army.

Let's be honest: most people who work in tech and business live the mercenary lifestyle.

You work at Amazon, Google, Microsoft, or the next big thing — that's OpenAI today, it was Uber a decade ago. And you do so because in many ways the mercenary lifestyle is pretty great:

The compensation is massive

Wage inflation in tech over the past two decades has been insane. I don’t need to tell you about the all-in comp packages people have been getting at big tech companies. The epitome of this today is the AI engineer making $1M at a FANG company. Not a leader or an executive—just an employee slinging code.

Even if you don’t hit that number, tech mercenaries still get paid top compensation in current, not theoretical future, dollars.

The perks are unbeatable

I won't list them all, as you know what they are: insanely generous parental leave and fully subsidized healthcare for your family. 401Ks with full matching. Catered lunches and lavish commuter benefits.

All of these forms of compensation — how much you are paid, and the perks you are provided, obviously matter quite a bit to how you live in our society. And so it is understandable why so many of us choose the mercenary lifestyle. I feel its siren call.

You work at massive scale

If you are working at Amazon or Google, you work in multi-billion dollar businesses. You support millions and millions of customers. The scale of what you do is massive in both numbers and impact.

But here’s the problem with being a mercenary: you are a sell-sword.

We like to tell ourselves that we are “changing the world"; but unless you are working on nuclear fusion, mercenaries are mostly just selling their services to the highest bidder. This has two major drawbacks:

You’re shipping another person's product, and that may not be your passion. The product might fit a market need, but do you truly care about it?

You take on a more junior, or narrower role. If you are a product or engineering manager, you are likely responsible for a "tiny" feature set. If you are an Ops Exec like me, maybe you are siloed into one narrow function or business area.

Being a Missionary

Here is the definition of a missionary: a person sent on a religious mission, especially one sent to promote Christianity in a foreign country.

Growing up in Palo Alto, I spent a lot of time in the backseat of my parent's minivan, staring out at the rolling hills along Interstate 280. Near San Mateo, there’s a famous (and now controversial) statue of Junípero Serra that overlooks the highway.

It's ironic this statue stands in Silicon Valley, the epicenter of so many tech missionaries.

Being a founder, or joining an early-stage company, is a missionary move. While it may offer the promise of glory, fame, or future riches, those are future promises that most times do not pay out. The true value in being a missionary is experiential; and we trade that experience for the material benefits and business scale enjoyed by mercenearies. Missionary life is about:

The joy of something new.

This is especially true if you are building a new software category, or taking a moonshot — but there is nothing like the excitement that comes from taking something from zero to one. The act of creation is in itself highly fulfilling.

Having a wide ranging scope

If you are a founder, your scope is everything. The entire company: its team, its customers, its investors. While the scale is smaller than what you would have at Google, the scope is broader and all encompassing.

If you join or found a startup, you will almost certainly have more responsibility than at a larger company — especially early in your career.

Navigating without a map

At a startup, no one hands you clear instructions. This is often because no one has ever done your job before, or your product and unique business model has never been built before.

Or maybe it is because no one has the time or experience to manage you properly; or because the business is so nascent you lack the real data to guide decisions — so you just try things and see what sticks.

One of the benefits of missionary life is that the map has not already been drawn — it is on you to figure things out, and draw it for yourself.

Both Missionaries and Mercenaries Get Killed

Whether you’re a sell-sword in another’s army, or a missionary founding an early-stage company, there is always a probability that you will be killed.

While many early stage startups like mine died in the last two years, thousands upon thousands of big-company employees were laid off. So don’t delude yourself—being a mercenary is not inherently “less risky.” When making either choice, you could easily be out of a job.

So let's be clear: the real risk is spending your time doing that which does not fulfill you. There is nothing inherently wrong with being a mercenary. Some of my best friends sell their swords — they have amazing families and careers; they are happy and fulfilled with their lives.

But despite how seductive being a mercenary sometimes feels to me — especially as I lick the wounds of failure — I cannot fathom being happy doing it. And it is not just because I am sick; it is because in the end I just love building sh!t.

So before I depart today, I’ll leave you with this: if you are considering what is next, be sure to ask yourself: Do I want to be a missionary or a mercenary? What do I actually care about? What do I want to spend my time on?

There is no right answer. There is only your answer. The one for your own wild and precious life.