The Stanifesto

Beyond Diligent

I've read enough "I'm Quitting My Startup" posts to know the structure. They start by congratulating everyone's hard work, then thank the users for making the community what it is today, and conclude with either that the company couldn't find a way to be profitable or that the company is being acquired but that everything will stay the same.

This is not one of those posts. It's half a year after I closed down Diligent and I'm not announcing anything, thanking anyone, or promising anything.

I sent this back in August:

It's been almost six years since I started Diligent with the goal of changing how non-profits and mission-driven businesses engage their issues online. In that time, I've been lucky enough to do some amazing work that I'm really proud of and collaborated with passionate, intelligent, and downright wonderful people. Still, Diligent never achieved what I had originally set out to do and now it's time for me to move on.

When I sent it, I was a bundle of raw emotion. Mad at myself for failing. Sad that I had to say goodbye to great clients, colleagues, and coworkers. Scared that I couldn't hack it working for a tech startup, or that I'd hate it.

It's been six months of sorting through those emotions and distilling them into coherent thoughts.


A lot of things are only obvious in retrospect.

Giving up on your startup is hard. Even more so when you've gone and named it "Diligent". I really should have named it "Judicious" or "Reasonable". It went on a lot longer than it should have. Runaway success always seemed right around the corner. Variable reward has a long relationship with addiction and there's no reward more variable than running your own business.

I also should have noticed earlier that I was doing too many things instead of delegating, burning my candle at both ends, burning up the limited supply of Diligent's only competitive advantage: my enthusiasm.

Context-shifting is exhausting and running Diligent was rapid-cycling between making and selling. The craftsman in me always wanted to make things a little better, a little faster, a little more delightful. The businessman in me knew that we had to count hours and dollars and, when either were running out, figure out how to get more. When one identity was active, the other would be bickering in the background.

I wasn't always happy with the deal these two selves brokered, sacrificing either quality or profit or more often both. That meant a lot of work went out that I wasn't completely proud of.

At the time, I blamed my clients. Not personally. I blamed the fact that, for whatever reason, non-profits and mission-driven businesses have either vision or resources but never both.

My biggest post-Diligent realization is that it never would've succeeded because I was serving a flawed market.


In my new job (for which, despite my fears, I am both qualified and thankful) the customers are typically small, independent game developers who'd rather focus on their physics engine or hitting 60FPS than how to make money doing so. My company makes money by helping them make money. It's refreshingly honest compared to the labyrinthine calculation of value fueling the non-profit industry.

Not that I didn't try. In the final years of Diligent, I read a lot about value-based pricing and computing the social cost of impact.

Impact is hard to quantify and even when quantified of questionable worth ("You provided 2000 gallons of clean drinking water... so what? Did that make life better? How much better?"). Assigning it into a dollar value was ridiculous.

Here's an example:

A study claims that a single pack of cigarettes bears a social cost of about $40. Most of this is shouldered by the individual in the form of health insurance, healthcare costs, and a shortened lifespan (and thus earning potential). The remaining $7 or so is born by the smoker's family, co-workers, lost productivity from smoke breaks, Medicaid and Medicare, and so on.

Based on these numbers, if Diligent built a website that convinced 1000 people to give up smoking for the rest of their life (let's say they had an average of 40 years left each), it would be worth between $200-500M to society.

How much would a non-profit with a $4M annual budget be willing to pay for that website?

In its final year, Diligent had one project that resulted in the passage of electric vehicular legislation for the state of California. The expert analysis pegged the economic impact of the bill at $13B for the State of California and its citizens via job creation, air quality improvements, improved municipal transportation, etc.

If the website we built were priced at 2% "equity" of the value it created, it would have cost $260M.

Obviously, it didn't. Not because the website didn't do its job, it did. Or because the non-profit was being greedy, they paid well. Because it doesn't work that way. Non-profits don't divide up the spoils of the change they create.


Peter Drucker might say that Diligent never made the jump from the "cost center" to the "profit center". That building a digital product was never seen as a primary mode by which to create change but as a necessary expense to support doing so via other means.

The truth is, there is no profit center in a non-profit. No equity. No exit strategy. There's just smart, creative people doing their very best to make their world a better place than yesterday, fighting for scraps of foundation grants or membership dues, and making deep life sacrifices so they can do it again tomorrow.

That life, and not Diligent, is what I now realize I gave up on. I still want to save the world, sure. Who doesn't? I also want to send my daughter to college. To own my own house so I don't get evicted and be forced to leave the place I love. To join a gym so I can take care of my body and not workout with rusty dumbbells in the basement.

Everybody works hard. Everybody deserves these things. Luckily, I know the hottest programming language so---for a pretty arbitrary reason---I get them. The truth of it makes me feel guilty, but also determined to find the best way to use the privilege I'm afforded.

I am still diligent.