The Fastest Learner Wins

When you’re starting a company, speed matters more than almost anything else. Not how fast you can code or how quickly you can close deals. How fast you can learn.

The fastest way to learn is to establish a cadence and stick to it religiously. Weekly is ideal. Bi-weekly works. Monthly is too slow. Quarterly is a joke.

Find Your Rhythm

We ran Rewind on two-week cycles from day one. Two weeks is long enough to get real work done but short enough that you can’t hide from results. One week feels rushed. A month lets you drift. Two weeks forces clarity.

Every two weeks, the entire company had deliverables. Developers worked in two-week sprints. Marketing ran two-week experiments. Sales had two-week targets. Everyone moved to the same beat.

At the end of each cycle, we bought lunch for the whole company. Early on, we’d pile into cars and drive to a restaurant. As we grew, we had lunch delivered to the office. It wasn’t about the food. It was about pausing to see what we’d accomplished together. Every two weeks, without fail.

I borrowed this ritual from my previous company and it became one of the most important things we did. It kept everyone aligned. It created natural checkpoints. It made the abstract concrete - you could feel the company’s progress every fourteen days.

The Cadence Changes As You Grow

Your cadence will evolve. Public companies work on quarterly numbers because they’re massive and their business is relatively stable. When you’re small and your revenue is growing fast, you’ll shift to monthly numbers. But when you’re just starting? Weekly or bi-weekly is where you need to be.

We launched Rewind in June 2015. Within seven months we had 1,000 people using the product. All free users - we hadn’t even built payments yet. We were testing whether people actually had the problem we thought they had. A thousand people in seven months gave us more than enough signal.

Compare that to selling to enterprise customers. You might close five deals in seven months. Five data points versus a thousand. Which company do you think learns faster?

Kill Things Quickly

A consistent cadence exposes what’s not working. Fast. We built a product called Retrieve for exporting data. Within two months of launching it, we killed it. Turns out exporting data is a one-time activity. One-time activities don’t make good businesses.

Could we have figured that out before building it? Maybe. But we learned it definitively in two months and moved on. No lingering questions, no “let’s give it another quarter.” Two months, clear signal, done.

The same discipline applied everywhere. We ran ads that performed so poorly I joked that installs went up when I paused them. We tried different messaging in emails. We rewrote marketplace copy. Everything ran on that two-week cycle - try something, measure it, adjust or kill it, repeat.

Align Everything

Here’s what most founders miss: the cadence isn’t just for product development. It’s for everything. If your developers are working in two-week sprints but your marketing team is planning monthly campaigns and your sales team is looking at quarterly targets, you’re out of sync. Information flows at different speeds. Priorities clash. Learning slows down.

When everyone moves together, the whole company accelerates. Developers know what’s shipping and when. Marketing can plan campaigns around releases. Sales knows what’s coming. Everyone celebrates together every two weeks. The rhythm becomes the company’s heartbeat.

Your job as a founder is to set that rhythm and protect it. Make it non-negotiable. Everything else will organize itself around it. And you’ll learn faster than everyone else still trying to figure out their timing.