By Ashish Kakran
Every founder has heard the advice: timing is everything. The uncomfortable truth is that timing is also nearly impossible to control. Being too early can kill a great company just as quickly as being too late. In fact, mistimed market entry is one of the top five reasons startups fail.
Through my experience working with founders across AI, infrastructure and developer tools, I’ve come to believe the ideal go-to-market window isn’t about perfect timing. It’s about holding a small but critical edge or what I call the 1.5x edge.
The 1.5x edge
Think of it as being a half-step ahead of the market. If you’re two steps ahead, you may wait years for buyers to catch up.
If you’re exactly in step, you risk being drowned out by noise and commoditization. But if you’re just slightly ahead, about six to nine months before the market really pulls, you have time to build an enterprise-ready product, win early design partners, and position yourself as the category leader when the wave crests.
The best founders position their companies as leaders in markets that don’t yet exist. At the same time, they close revenue in adjacent use cases that buyers already care about. It’s a delicate balance of vision and pragmatism.
Lessons from markets that were too early
A few years ago, MLOps companies built sophisticated tools to manage dozens of models in production, including fine-tuning, monitoring and observability. The problem? Almost no one had that many models in production. The technology was brilliant, but the buyers weren’t there yet. Many of those startups failed not because of a bad product or bad teams, but because they were solving tomorrow’s problem today.
Fast-forward to now: With LLMs and GenAI, the market has finally caught up. Suddenly, everyone needs robust MLOps and LLMOps. The pain is real, and the timing works.
When the wave hits
Look at AI code generation. Early players such as GitHub Copilot and Tabnine built strong products, but the market wasn’t ready. Then came ChatGPT, which shifted perception and normalized AI as a daily tool.
Cursor and Windsurf didn’t invent a new model. They combined standard IDEs with APIs from OpenAI and Anthropic to create an integrated developer workflow. The timing was perfect. Distribution and adoption followed naturally.
The takeaway: You can’t “time the market.” But you can be prepared when the moment arrives.
It is teams of nimble founders that can rapidly adapt to the changing market conditions who are likely to win. The rate of change with AI is both a challenge and an opportunity. On one hand a new model release can make a subcategory obsolete. On the other hand, best founders see it as an opportunity to discover interesting new use cases as their competitors fight for survival.
How founders can calibrate
So how do you know if you’re too early or just early enough? Talk to customers and prospects, constantly. Many technical founders fall into the trap of selling the brilliance of their tech rather than listening to real pain points.
Beware of the shiny-object syndrome. I have seen meetings where exceptionally talented founders spent 30 minutes in front of top CIOs and just kept talking about the cool technology. It can be a wasted opportunity as the buyer might walk away not knowing what the company actually does. Discovery matters. If your ICP doesn’t understand what you’re solving, they won’t buy it.
Founders should also look beyond the C-suite. Champions can sit a level or two below, where up-and-coming leaders are hungry to bet on new technologies that accelerate their careers. These champions can make or break your early deals.
Another key: over-deliver in the first six to 12 months. Close early design partners with favorable terms, but make sure they feel real ROI. Turn them into internal champions who will fight for you in rooms you’re not in. Churn at this stage can be devastating, not just to metrics but to founder morale.
Why staying ahead still matters
Even if you find the edge, it won’t last forever. Competitors will catch up. Markets will shift. The only way to maintain an advantage is through relentless product innovation and customer closeness.
As Jyoti Bansal, founder of Harness 1, once said: “You don’t want to cross $100 million ARR with a single product.” The best enterprise companies continually invest in the next product about two years before the market needs it, ensuring there’s always a new growth driver ready.
Timing the market may be a myth, but staying ahead of it isn’t. By keeping a 1.1x to 1.3x edge, slightly ahead of buyer demand but close enough to capture real use cases, founders can avoid the trap of being “too early to matter” and position themselves as the leaders when markets shift.
The edge is small, but it’s everything.
Ashish Kakran is a partner at Sierra Ventures, where he invests in early-stage companies in AI, infrastructure and cybersecurity. Previously, he has backed founders building category-defining companies such as Cohere and Harness.
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