Early stage startups can be chaotic. Many good reasons exist to explain this reality. The uncertain slog towards product market fit, or PMF. The pressures of reaching certain moving milestones in an effort to satiate potential investors. Additionally, the struggle of plugging talent gaps by hiring or finding external vendors when those skills are missing on the founding team.

There are numerous facts and opinions about why startups fail, and why it can be a Herculean-like epic at the beginning of a young company’s journey. I don’t dwell on the failures as much as learning how to ward off trouble signs on the horizon.

One of the key topics I cover in my newsletter is about applying constraints to processes. I argue that without constraints, it’s hard to understand what’s a valuable set of activities that deserves focus. Even during the bull market years of startup valuations, the concept of throwing ideas against a wall to see what sticks has always been heralded as a recipe for disaster.

In fact, this behavior can arise from the tension between internal and external expectations. It can be hard to achieve 20/20 vision if there are no constraints, such as OKRs or a unified understanding of expectations and priorities.

I always love this question posed by Rory Sutherland, “What information would be useful to know?” It’s powerful because if you have a goal and a list of restraints, you have taken dramatic steps towards testing your hypothesis inside early stage startups, let alone big business.


There may be some fault in this hastily constructed equation. The major point is that in most cases we are simply solving for what activity will produce the results we desire. Often, this is where the spaghetti approach takes hold. However, if we zoom out and ask Rory’s question one more time, then we can begin to start using data to guide us towards a smarter, more efficient list of activities to prioritize.

It is true that early stage startups start at ground zero for data. Few users have tested or tried their product or service. There may not be a ton of money to increase awareness or drive user conversion by using performance media. However, these are constraints with solutions. A better question at early stage startups may look this: How can we generate early signups for our app when we don’t have money to invest in ads? This allows us to constrain brainstorming and ideation instead of having a free-for-all.

GOAL = generate early signups
ACTIVITY = X ‘variable’
CONSTRAINT = $0 or no money

Now, all that’s needed is a new set of specific and constrained questions. Can we leverage our personal networks to gather early users? Can you use ChatGPT to help us write organic content to drive traffic to our website or post on social media? Can we partner with any businesses or organizations that might see utility in the use of our app long-term? We rank these suggestions by feasibility, expected return, timeline, and resources needed. Then, it’s off to the races.

When you have great questions, you can create great tests which are a breeding ground for data collection. Early stage startups have to remember the pressure will never go away. It’s inevitable that the bar will move on the next milestone. Unfortunately, marketing strategies and tactics that worked yesterday aren’t always replicable tomorrow. Don’t let fear and pressure force you into messiness.