🏆 The privilege of mediocrity.

Acknowledging the reality of: who we have as builders is a function of who we afford the safety nets of failure to.

Photo by Glen Carrie on Unsplash

We humans love our patterns. They help our poor overworked brains take in info and make quick sense of the world around us, rather than leaving us to have to reanalyze everything from scratch.

“Pattern matching” helps us navigate daily traffic and the morning coffee shop. In meeting new people and cooking dinner.

It also plays a starring, (often unspoken), role in the funding of start-ups. I get it - there are just too many ventures, too many founders, too many variables to have to wade through to figure out who and what to fund. And these are matters of probability and returns, not merit and morality, per se. There has to be some simpler “first passes”, broad “theses” that helps narrow in to the set of things to dig into further.

Ivy league schools. Engineer at a FAANG co or even better: airbnb or Stripe. Buddies with so-and-so. Silent signals to project future potential.

When you fit the pattern, it’s like a wallpaper your trials and misses blend into. Distributed amongst a fabric that can withstand your boldness and often your badness - your mediocrity - so that you’re not remarkable …. until you are.

Those without the benefit of such a pattern, a tribe of successful others to shield the jagged edges of their learning curve, stand out starkly. Their every move and miss watched and judged and attributed to not just them, but anyone who might be like them.

Mediocrity is the basecamp of any worthy endeavour, on the path to excellence. Most of us have to not only pass through it, but spend a lot of time there before we attempt the summiting (and often not just once, but many times). While we’re there, we don’t look very exceptional. We’re trying to learn in weeks what others have had lifetimes or can skip entirely. We exhaust ourselves on things others can converse their energy on.

These others need not spend a lot of time stationed at the very public camp of Mediocrity. Because of the resources they possess or the partners they’re able to piggyback on or the helicopter that will drop them privately at a secret back entrance halfway up.

It doesn’t mean that their skill is any better. Almost the opposite. Because they’ve spent less time honing the basic grunt stuff, they can cowboy their way to greater heights, masking their mediocrity. They can use (other people’s) money to be brash and ambitious and game-changing, hiding all matters of sins and shortcomings. Or they can network their way to smarter, resource-saving shortcuts.

While the others at basecamp know that if they blow this, there is no coming back. For them, there is no room for mediocre once they leave. They have to be perfect. A little less bold, play it safe. Can’t make a mistake, otherwise not only do they not get another chance, whole classes of people like them will get taken out of consideration. So they’re more judicious. Measured. With capital and with plans.

Just to hear: “You’re not thinking big enough”.

The bigger is there. What’s not is the backup should it fail.

📈 To build big, we need safety nets to fail up.

On the frontiers of forging new companies and new realities, there is nothing so important and yet under-talked about as: the safety net for failure.

For fail one shall. On path to the remarkable if there is no failure, the results are too modest and the effect is incremental. If you’re not failing, you’re not trying hard enough.

That’s the saying right?

Well it’s certainly easy to say when the price of failure isn’t fatal.

Those who live the tale of life after failure by definition had the benefit of a soft(er) landing. Some way to break the fail, get dusted off and get back on the proverbial horse or rocketship.

But we don’t speak of such things.

So then we keep the burden of proof on the few. And these few have to be exceptional to start a pattern where others may follow behind with greater ease.

Meanwhile, for those blessed with the privilege of ignored mediocrity, we don’t let the performance of peers get in the way of their certain genius. It’s not like anyone is saying: Don’t fund white dudes with dark flowy hair after the spectacular fails of Adam Neumann or Travis Kalanick. On the contrary, they get funded with even bigger rounds. Not even bad behavior gets in the way of big bets and promises of even bigger returns.

But perhaps the point is better made on the backs of the scores of really great founders I know who have endeavored valiantly. “Failed”. And ended up acquired by a “buddy’s” growing start-up.

To be mediocre (and I say this in the kindest way possible - to be just not remarkable or excellent yet) and still keep winning and getting second and third chances will always be the ultimate privilege.

Because as hard as building a startup is, it’s easier when you have a safety net for yourself and your results won’t take out a whole group of others behind you.

Not all of us get to take wild, reckless swings. If I raise $100M (hell, even $10M) and fail, it’s a commentary on my gender, my race, my certain lack of commitment, as a mother. So I make safer bets on $2M.

It’s now widely understood that female founded companies do more, with less, faster. Because we’ve had no choice.

But wouldn’t it be nice to do more, with more?

(That’s sidestepping entirely the toxic practice of writing hit pieces on female founded companies for behavior that is laughably tame at the startups of male counterparts. Which is not to excuse any bad behavior but to put a face to the exact mediocrity we turn blind eyes to).

Until I (and my peers) get the benefit of doubt - of safety nets that bounce me up into even bigger and better opportunities as Mr. Neumann and Mr. Kalanick and Mr. Conrad and Mr. Anynumberofothers clearly have - any concept of “level playing field” is a farce at best, a tragedy at worst.

(Btw - I’m not delusional to think I have the talent of Adam Neumann or Travis Kalanick - I don’t know them and likely those who do will say “they’re a visionaries of a different sort” or some such thing. My contention is not with them per se and more with what they represent - a whole class of founders who get to “fail-up” constantly and continuously).

You need to drown me out in a sea of other brown, non-technical founders in their 40s to make my wins or losses fade into a background of constant endeavor. Otherwise what I do or don’t do sends a beacon out across the lands, more noise than signal, of what founders who look like me might be able to do.

And it’s not just in the land of start-ups. You see it in sports and in boardrooms. In movies and in restaurants.

Shonda Rhimes. Serena Williams. Reese Witherspoon. Lin-Manuel Miranda. Beyonce. Mindy Kaling. John Chu. Taylor Swift. Chloe Zhao. Kumail Nanjiani. Indra Nooyi. (I could go on, but it’s also the point at hand that I’m able to so readily name individuals to represent breakthroughs for their peoples.)

Each of these people have had to painstakingly build up their careers, playing it safe, building their own safety nets before they could eventually do the things they’ve always been dreaming of.

Because they have always known: if they put out a project that was bold in ambition and vision but didn’t hit in execution, not only would it impact their second chances but those of anyone that looked like them.

So they’ve have hustled and sweat their way to build safety nets. For themselves and everyone behind them.

And boy are we lucky for it. Hamilton. Black Panther. Morning Show. Never Have I Ever. Every match Serena has played. Each a revelation in their own right, making way for more brilliance. And making it easier for scores of others like them.

But the pressure on their shoulder must have been tremendous along the way.

🎲 Playing the long(er) odds.

Not everything can or should be reduced to matters of privilege but if I’m already playing the longest of odds, I want to know exactly how much longer they are for me, as a non-SV, woman of color with (gasp) children.

If I fail, if I prove to be mediocre, how much of that gets painted as a function of my gender, my family, my race as opposed to just this endeavour?

We all like to think in America that we live in the land of equal opportunity. Of equal ambition.

But to understand if that’s true, we have to look at the other side of the meteoric rises and the funding and the building. To the lacklustre, the underwhelming, and in the cases of a few, even ruinous and destructive.

Who do we readily excuse for their mediocrity, as a part of the “process”? Who do we hand second chances to? Who do we not write off their gender and race and class for?

This is not, by the way, a commentary on taking away the benefits afforded the few bold builders who have them today (well, I can name a couple who I wouldn’t mind having to work a little harder to prove themselves again). This is about giving more people access to the safety nets of second chances.

🥅 Safe landings for all who strive.

To be specific, there are 3 kinds of safety nets we need:

1. Financial. That’s both funding to do the venture so founders/ creators aren’t personally devastated should it not work. Because there are few that can or will attempt another after that kind of wreckage (even worse for people with families or student debt or caregiving commitments). But it’s also getting plugged into the informal network of “acqui-hire” exits. This little spoken way to emerge from a failed venture with an “exit”, a job and often a bit of financial upside. Often initiated and negotiated via social connections or the through the network of investors.

2. Emotional. We need to make the process of mediocrity on the path to excellence the lore we celebrate. But not only through the lens of success looking backwards. When something fails or doesn’t find the footing it sought, celebrate the trying. Make it not emotionally devastating to feel like a failure but rather, an admirable gladiator in the arena who was brave and bold enough to have a go.

3. Reputational. Don’t let the failures get buried between the bullets of “successes”. Make it possible for more than the few to write “exit” even when the outcome wasn’t materially different than a shut-down. And see the attempt as admirable as the outcome.

I can speak of all of this because I’ve had to both build my version of each of these safety nets. I still am. But I have certainly benefited from having people giving me a second chance. People that really see me - not the labels.

Still. We have far to go.

Because my labels precede me. Female founder. “Mom”preneur.

I don’t want to be exceptional to have a chance at winning.

I don’t want my results to be an indictment on the efforts of my gender, my race or my reproductive status.

I want to blend into the endeavors of the scores of other mamas and women and black and brown builders.

But until my ability to find 10,000 ways that don’t work, isn’t a commentary on my labels, we have work to do.

Until I, or anyone like me, has the privilege of being mediocre until we are exceptional, we have work to do.