All founders are a**holes

Including yours truly.

I didn’t come up this line. It was said to me by a friend who has worked with many founders. She said it both as a compliment and as a prediction. That all founders she’d seen were assholes. And I wasn’t. Yet. 

I didn’t disagree with her. This had been my biggest worry since starting up. That Harvey Dent was right. 

You either die a hero, or live long enough to become the villain (aka asshole).

You see founders, at their very core, are dreamers. Dream-sellers rather. 

We see a vision. We want to create it. We have no idea what path shall take us there. But we know we ain’t getting there alone. We need a team that believes in the dream. Investors that believe in (the value of) the dream. Vendors, suppliers, customers, all of who believe in the dream. 

So, once we are fully sold, we start selling everyone else. Of course, we don’t tell everyone that we have no clue how to get there. People need certainty. To varying degrees. But always more than the founder. And rightly so. Else they would’ve started up themselves. 

Here’s the thing about selling dreams though. They sound eerily like promises. 

We’ll build the largest XYZ this country has ever seen. 

We’ll build the best team culture, one we always missed in our jobs. 

Do this shitty, operational role for two years, then do whatever you wish to. 

A decade of building this, and we’ll all create generational wealth. 

We’ll build this together. You and me. Shoulder to shoulder. Till IPO and beyond!

We don’t know any of this to be true. We believe it with all our heart. But we have no clue what it takes to do any of this. Yet, there’s no room for doubt. The more impassioned the plea, the clearer the vision, the more people are likely to drop what they are doing and join the crusade. 

So you sell. And once the dream is sold, you start. 

Of course, people aren’t stupid. They have doubts. Many doubts. What all can go wrong is all that’s discussed at the start. It’s everyone’s defense mechanism. Imagine the worst, then work day and night to avoid it (middle class Indian upbringing in a nutshell). 

But what happens once it starts going well?

Consumers love your stuff. Investors give you a lot of money. Every month you double the previous. You’re spending 16 hours a day fulfilling orders. Everyday 10 things break. Everyday you fix them, only to come back next day to 10 more. The madness bonds you. It also brings down everyone’s defenses. It’s happening! Maybe the dream wasn’t as wild after all.  Maybe this is the rocket-ship that will take us to the promised land. Together. YASSS! 

And then one day, it stops. 

Used to growing three-fold each year, you’re suddenly staring at a flat year. Same store sales are declining. Competition is catching up. Fed has increased rates. Funding has dried up. Covid has hit. Putin has decided to go to war. Input costs are soaring. You can’t make enough product. You’re can’t launch a new one either. Your org can’t manage the complexity. You need systems. That needs investment. But money is thin. Should you spend it on generating demand? Or ensuring supply? Or setting up systems? Or hiring someone who knows how to do these bloody things?!!

Ask any entrepreneur who’s had a good run. All of them hit this point. Different stages, different intensities. But all companies go through this. The messy middle.

At this point, you have two options. 

If you’ve already built something worthwhile, sell. Exit. Take the cash. Leave the game. Die a hero. 

This is a great option. Everyone makes decent money. Founder might even make generational wealth. The OG team is the one who sees the story through. Your memories are like war stories. How we built this thing together. How we got here like a band of brothers (sorry, but all these war analogies unfortunately use male nouns. Sisters are very much a part of it. Emotionally even more than brothers I’d argue). 

You and your team go down in history as winners. Look at this founder who create a X crore business in 8 years. The podcast cover image paints itself. 

But what if, by the time you hit this plateau, you’ve not built something worthwhile. Or you have, but you don’t wish to exit. In both cases, you want to continue building. You have to! Your vision is unfulfilled. You just can’t let the dream end!

But, and this is the biggest, fattest, ugliest but you’ll ever face, you have no clue how to get out of this rut. 

Unlike the case studies you debated retrospectively in B-School, the one single reason for your troubles isn’t clear at all. Everything seems to be falling apart at the same time. Demand, supply, systems, process, culture - everything is crumbling. And the best advice you’re getting is - 

What got you here won’t get you there. Also, who. 

This is the point where heroes tend to become assholes. So, before we proceed, let’s define asshole. In my conversations, I’ve found three traits that people identify as assholish behaviour. 

One, is integrity. Founders who shortchanged people willingly. Like it was always the plan but they’d been lying all along. This, unfortunately, seems to be a sizable set. And they deserve the moniker. And none of your sympathies. 

Two, is when founders change. 

He is no longer the guy I joined. He used to be fun. He used to be open. Now he is just grumpy and closed and judgmental. Also, he used to be democratic. Our opinions were heard. Now he just takes decisions and informs us. I feel like an employee. This is exactly the feeling I left in my previous job. I didn’t sign up for this. Asshole. 

Three, is when founders deviate from the dream. A dream which was received as a promise. 

We were going to serve a mission, but now he is belying the promise (and he didn’t even consult us). Asshole. Till last year I was the best thing that ever happened to the company. Now, suddenly, I am not scaling. Asshole. Oh, now i get it. He was setting the stage to hire some CXO to become my boss. Guess we’re not doing this ‘together’. Asshole. And wait, what! He gave that CXO more shares than I have! ASSHOLE!!!

If you decide not to die a hero, these are just some of the ways you risk becoming a villain. There are a million more. Because the villain isn’t you. It’s change. And the minute you decided to go on, you decided to become the primary agent of this change. 

Of course, you may argue that over-communication is the answer. Tell your team everything that’s going on. Explain every action. Why you are doing what you’re doing. They’ll understand. If this is your argument, I bet you’ve never seen wartime. 

When you’re being shelled from all ends, there’s no time or energy for explanations. A good general takes the reins and leads. And changes tact and strategy to whatever keeps the dream, in some shape or form, alive (remember, Mr. General is winging it too). Some people, some culture, some promises get sacrificed in the bargain. We’ll heal those wounds once the shelling stops. But first, we live. 

Right or not, that’s the narrative in many founders’ heads. As it was in mine.

Yup, we’ve been through one such test. Dying a hero was an option. But exiting wasn’t something I (or my team) would even consider. So it had to be option two. Become asshole. 

And became one I did (I know because my team told me). Unknowingly, at first. Begrudgingly later. Because I thought this was the only option. That old behaviours will need to change (starting with me). That quick decisions will need to be made (no time for consensus). That some promises will need to be broken. That some people (this one hurts the most) will need to be left behind.

Thankfully, that time didn’t last too long and we escaped with minimal damage. Now that we are well and truly out of the trenches, and I’m back to being me again (team has told me :)), I look back at that time with horror.

It’s all a blur really. I don’t recall the exact time I changed. Nor do I recall doing half the things the team tells me they found villain-ny. I just remember being scared myself. And hating who I was becoming. Boy am I happy we’re out of it. 

Or are we? Senior founders now tell me that there isn’t one messy middle. There are many. One every 2-3 years. Ad infinitum. The longer you continue, the long this continues. Shit. 

Honestly, I’m none the wiser on how it’ll be next time. On who I will be. Who I will become. Last time taught me that trying to be someone I’m not doesn’t help. But what does? I don’t know. And that’s scary.

For now, I’m putting all my energy into today. Into ensuring we don’t become complacent. Into ensuring this peacetime never ends. I know it will. But I am going to do all I can to prolong it. The team is in on this plan (peace times allow for getting buy-in). And we’re giving it all we’ve got. Because now we understand, that the more we sweat in peacetime, the less we bleed in wartime.