Nobody wants to choose
I used to think strategy was theory sold by management consultants in fancy decks. Most builders don’t theorize. They build, ship, and outwork everyone.
That’s how my mind worked for years. It’s how most minds work. We’re conditioned from childhood. Work hard, get good grades, get into a better college, land a better job.
Hard work is the answer. The startup world just repackages the same message. More hours, more calls, more demos, more meetings, more features.
And brute force does work. It creates momentum and gets you something.
Then it stops.
I built my second startup on pure grind. A home renovation marketplace. Discovery, design, materials, contractors. We covered every step except the one that mattered most: project execution.
Had we done nothing but project execution, we’d have won. Instead, we spread across the entire value chain and owned none of it.
Segmentation was worse. We targeted first-time homeowners. Clueless about the market, but gullible enough to fall for contractors with lowball quotes. Our product couldn’t compete with a cheap lie. We shifted to second-time homeowners, but they wanted full home renovations which we were not good at. So we took on whatever came our way because we were desperate to grow.
We never stopped to choose. We just kept moving.
That startup failed. For a long time I blamed the market. Eventually I ran out of excuses and realized I didn’t know how to think clearly.
Grinding wasn’t the variable that mattered. Choices were. The thing we never did was sit down and decide what to say no to.
Plenty of people have a bias for action. Almost no one has a bias for clear thinking, which is why so much action leads nowhere.
That’s what strategy is. Deliberate choices that maximize your chance of winning.
The right choices feel wrong at the time. So people don’t choose.
DoorDash chose suburbs. Every competitor was fighting over metro cities. Suburbs looked like a dead end. Too spread out, too few restaurants. But suburban households had no delivery alternatives. Customers had no other option. Restaurants had no delivery infra. Families ordered bigger, ordered more often, and told other families. DoorDash grew undisturbed while competitors bled each other dry in Manhattan.
Nintendo Wii launched with deliberately worse graphics than PS3 and Xbox 360. The gaming industry was in an arms race for processing power. Nintendo made a cheap, motion controlled console for families and non-gamers. Outsold both competitors.
Costco carries 4,000 products. A typical supermarket stocks 30,000. Fewer SKUs meant higher volume per item, insane supplier leverage. If Costco stocked it, customers trusted it was the best option. Less choice became the selling point.
All three choices looked stupid at the time. That’s strategy.
The hard part isn’t knowing this. It’s doing it.
Because choosing means killing options. Saying no to customers who want to pay you. Walking away from revenue that’s right there. Letting go of ideas you’re emotionally attached to. All of it feels like losing when you’re desperate, underfunded, and your investors want growth yesterday.
Grinding feels productive. You can point to things. Shipped features, closed deals, filled roadmaps.
Strategy feels like sitting still. It looks like staring at a wall instead of flooding Slack. It looks like saying no to revenue. It looks like doing less.
No one gets promoted for staring at a wall.
So people avoid it. They fill templates and call it a “Strategic Plan” which is neither strategy nor a plan. Just aspirations arranged to look official.
They attempt strategy by committee. Committees don’t choose. They dilute. What survives is whatever offends the fewest people. Tradeoffs don’t survive this process.
Real strategy induces short-term pain. If nothing hurts, you haven’t chosen anything.
Strategy never gets easier with practice. The better you get, the more you see. Every tradeoff. Every consequence. Every second and third-order effect waiting to unfold.
Awareness multiplies the cost of every choice.