Strategy: Counting backwards

Quick tip for anyone wanting to get better at strategy: try counting backwards.

It’s rarely the case that we have the luxury of operating without time constraints.

Startups only have so much runway before they run out of funding.

Companies in competitive markets with quickly changing user expectations only have so much time to innovate before they will lose their position or miss their window of opportunity to get acquired to establish an advantage.¹

Take a guess at how much time you think you have, and start to count backwards.

For example, startups tend to raise about 2 years of funding in the earlier stages. So we’ll start counting backwards from 24 months.

It takes 6-9 months to fundraise, so let’s count backwards to 15-18 months.

We obviously need to have something to show at the time we start the fundraise, so we need to then bake in 6 months of traction.² That puts us at 9-12 months.

So counting backwards, we have 9-12 months to discover, build, iterate (and repeat) whatever it is that delivers the kind of outcomes that will net us the next big fundraise, exit, etc.

For me, that changes things. The universe of options available, the war-time mentality of urgency and bias for action, the ruthlessness of prioritization and saying no to distractions, all becomes a lot clearer when I imagine having 9-12 months to deliver impact, vs where we started, which was that we have 2 years of runway.

Where does your company or product need to be in 2-3 years? After counting backwards, accounting for fundraising, sales cycles, development time³ , how much time do you actually have? Does that change how you think about right now?

The Workshop

This is a newsletter-only section where I share a half-baked idea in hopes that y’all who are smarter than me can work it out with me.

Reddit has used its robots.txt file to block Microsoft’s Bing Search completely, along with some smaller search engines like DuckDuckGo.

The reason? They can’t agree on how much money to pay Reddit for access to their user-generated community content, which has soared in value as AI training data.

It immediately reminds me of the cable TV retransmission hardball negotiations, where channels would suddenly go off the air completely because, say, some local broadcaster is refusing to pay $x per month per subscriber in order to carry a bundle of channels.

The shift in power dynamics are what’s notable to me. Publishers of content, like Reddit, had typically been on the receiving end - they are hungry for more search traffic, investing millions into SEO, in order to drive user acquisition and page views.

And now, they are literally blocking the traffic, because now they have the more valuable asset: gobs and gobs of high value data.

I’m sure this will all get settled eventually. But wow, what a reminder that, at the end of the day, if you aren’t paying for the product, you are the product.

1  Even at the level of your one team within a bigger company, I’m sure your team or product has goals that are longer term than the work immediately in front of you: some desire or expectation to do more than incremental optimizations, but to improve the company’s value and strategic position in some notable way.

2  This is a bit of an unrealistic average of consumer timelines (which could be as short as 3 months) and enterprise timelines (which could be 12 months just to get an LOI signed).

3  Also, time lost to big refactors and replatforms, or other internal programs like rebranding, adopting design systems, switching to a new ERP, etc.