How to Make Decisions Like a Proper Business
When you make the jump from a corporate job to entrepreneurship lots of uncomfortable things happen:
You suddenly own your days, which turns out to be surprisingly scary (it’s way nicer to have someone tell you where to be and when than you’d realized), you own your to-do list, which turns out to be scarier than owning your days (it’s way nicer to have someone tell you what’s a priority than to try and figure it out for yourself), and, you start treating your bank account like my son treats a spider in the living room (you peek at it through cracks in your fingers and then sprint away crying).
This is, hopefully, balanced out by the perk of entrepreneurship: you get to hack away at the single problem you’d choose out of all the problems in the world. This is intoxicating, and it causes most of us to run away from everything we did in our past corporate lives like my son runs from an ant (those scare him, too).
The problem with leaving the corporate world and assuming it was all silly bureaucracy is that a lot of it wasn't. Lots of what you do in the corporate world exists because smart people figured out that it works. And some of it is worth taking with you when you leave, along with the code for your corporate discount on rental cars.
Making decisions is hard
During my venture days, whenever we got close to entering diligence on an investment (taking it seriously), my boss would task two people with creating the “arguments of the case.” One was for diligence, one was against.
Importantly, the person he’d choose to create the “pro” case was always someone he thought was against the investment, and the “con” case was made by whoever was most excited about it.
Each was given 72 hours to build their case and present it to the group. We’d order in tacos and vote at the end. It was fun.
Importantly, every decision was judged by the same rubric and had a skeleton of Keynote slides to be filled out:
For the pro case:
Right now, our thesis is: ______
This investment fits the thesis better than other options because: ______
The important differentiator is: ______
It suits us uniquely because: ______
It’ll be a no-brainer “yes” if we figure out: ______
For the con:
Right now, our thesis is: ______
This investment doesn’t fit the thesis as well because: ______
The potential differentiator is: ______
But it falls short because: ______
It’s a clear “no” if we figure out: ______
A better option might be: ______
Also importantly, our current investment thesis, goals, and unique attributes were clearly listed (and known by everyone by heart).
The result was a spirited debate, the strengthening of both arguments, and fast decisions. And tacos.
How to do this in your one-person startup
Your startup is basically a process for making decisions with incomplete information. This process starts the moment you start working on the business. It either develops, or it doesn't.
When you’re facing a high-impact decision — like hiring a dev shop, choosing the price you’ll charge, adding a cofounder, or introducing a subscription tier — don’t wing it. Start to develop that decision making process. Even if it’s just you, build out a short deck for each side of the argument.
I do think the rubric is different for startups — here’s what I recommend:
Startup decision rubric
PRO:
Right now, the most important thing we’re working towards is: ______
This opportunity helps us make progress better than other paths because: ______
It’s uniquely suited to our team’s skillsets, networks, and knowledge because: ______
We’re more likely to succeed with this than other options because: ______
To make this a no-brainer, we need to learn: ______ (in the next 72 hours or one week max)
And two clarifying / contextual prompts:
Is it better to be fast or deliberate with this decision? Most decisions are less important than you think, and speed towards a clear goal is usually the best approach.
Finally, tell the wild success story of this approach working. Where do we end up?
CON:
Right now, the most important thing for us is: ______
This opportunity doesn’t help us do that because: ______
It doesn’t match our unique qualifications because: ______
To make this a no-brainer “no,” we need to learn: ______ (in the next 72 hours or one week max)
A better option might be: ______
And two clarifying / contextual prompts:
Is it better to be fast or deliberate with this decision?
Finally, tell the story of the worst case scenario. How bad is this if it doesn’t work?
The variables that drive the decisions
This is really hard to do if you don’t have clarity around what you currently want.
So, have these, always updated, at the top of your Notion Page or Google Doc or whatever you use as home base for your startup work:
Our current priority is:
Our unique, unfair advantage(s) is/are:
Our six month story (wild success in the next six months)
Our three year story (wild success in three years)
How to use it
At the next important decision, build out these two decks and pitch them. To me, to another mentor, to a friend, to your mom. The process is what you really need.
At your last (or current) corporate job, if there was a decision that would directly impact the future of the company, how would they make it? They’d have structure, they’d see both sides, they’d have a clear set of success variables and expectations, and they’d get outside eyes on the thing. They wouldn’t just fly by the seat of their pants.
They’d also likely move way slower than we’d like - and most decisions early on should be optimized for speed, since you’ll never get enough information to make a truly informed decision.
Knock out the arguments, give yourself a few days to get more data, pitch the decision, then make it and move on.
Be structured, be fast, and get better at this. And don’t look at your bank account.