There used to be a pretty straightforward playbook for building an enterprise software company.
Act I – The Wedge (aka Unbundling)
Start with some feature or market niche that was underserved by current solutions. During a platform shift, you’d pick-off a feature of the existing platform that could be made 10x better in the new regime and use that as the wedge.
This niche needed to be large enough to scale to tens of millions of ARR quickly, but not so large that it attracted ruinous competition. Statsig started with product experimentation. Rippling started with an orchestration tool for onboarding and offboarding employees. Etc.
Most startups would spend 3-5 years building the initial product, hiring the initial GTM team and then scaling to $10-50M ARR before starting Act II.
Act II – The Suite
Act II was about launching adjacent products that let you scale past $100M ARR. Instead of a single product, you built a suite of products.
Statsig started with experimentation but then added feature flags, session replays, product analytics and more. Rippling started with payroll and HR workflows (onboarding/offboarding) and then added a bunch of HR, benefits and recruiting-specific products to round out the offering for the same buyer.
For companies that made it this far, this might take another 3-5 years of wall time. As the first product scaled to $50M ARR, you start cross-selling products #2 & #3. At $100M ARR, maybe the next two products are each doing $10M and $1M respectively. This suite approach unlocked the ability to to get to $200-500M+ ARR.
Act III – The Platform
The end game is rebundling. As you accrue enough heft and user engagement, you would eventually earn the license to rip-and-replace the platform underneath you. This was the basic premise of all of the “Systems of Engagement” that were commoditizing the “Systems of Record” underneath them. This was how you – in theory – scaled to $5B+ in durable, sticky ARR.
Speedrunning the Playbook
I fear the three-act playbook is dead. I think the world is moving too quickly.
The three-act approach implicitly relied on some amount of calendar time, especially in the early days. The founders could only do so much – first you were focused on finding product-market fit, then building out the early GTM motion, then scaling GTM. The reason you didn’t start Act II until you were at $10-50M in ARR was because you were still single-threaded on Act I.
The number of businesses that have gone from ~$0 → $100M ARR in the past couple of years (Cursor, Cognition, Clay, Harvey, Sierra, Baseten, Fireworks, Lovable, etc.) is evidence that the world has shifted.
There’s no time to be precious about a step-by-step strategy. As the cost of software engineering plummets, the time to finish Act I and Act II also approaches zero. I think the rational thing to do is to just plan to build it all quickly, mostly from the start.
Ambition
For me, this has caused a pretty profound change in my approach to early-stage investing. I used to look for the protective wedge – the harbor where you could safely get to $10-$50M ARR. Now, the wedge feels like small ball. I find myself wanting folks to just jump straight into the deep end.
E.g., I remember meeting Anysphere (Cursor) at the seed. At the time, I think their plan was to just straight-up replace VS Code because it was too limiting for AI coding. This seemed crazy to me – VS Code was beloved at the time. After years of IDE fragmentation, VS Code had finally won. Why were you going to just straight-up replace VS Code as a seed-stage company? It seemed far more sensible to start by building an extension and then earn the right to replace it.
N.B. – I was wrong. Now, replacing VS Code almost feels under-ambitious. Why stop there?
As the cost of writing software drops to zero, I find myself valuing ambition above all else. Unreasonable, unrelenting ambition.
I think the three-act play is dead. Relying on a wedge in a period of rapid change is too timid. I think if you’re going to go for it, you should probably just go for the whole thing.