Startup founders often sell visionary upside, but the majority of customers—especially in enterprise—purchase products to avoid pain or reduce risk (e.g., missing revenue targets). GTM messaging should pivot from the "art of the possible" to risk mitigation to resonate more effectively with buyers.

To get C-suite buy-in for long-term brand investment, marketers should run small, ring-fenced test campaigns. By isolating a market segment and layering brand tactics on top of demand generation, you can demonstrably prove superior growth compared to a control group, de-risking a larger investment.

Instead of a rigid plan, early-stage companies should establish core GTM "tent poles": a defined ICP, answers to the four essential questions of value, and an engagement model. These elements provide structure but can be flexibly adjusted based on market feedback without causing the entire strategy to collapse.

Foster a culture of experimentation by reframing failure. A test where the hypothesis is disproven is just as valuable as a 'win' because it provides crucial user insights. The program's success should be measured by the quantity of quality tests run, not the percentage of successful hypotheses.

When introducing a disruptive model, potential partners are hesitant to be the first adopter due to perceived risk. The strategy is to start with small, persistent efforts, normalizing the behavior until the advantages become undeniable. Innovation requires a patient strategy to overcome initial industry inertia.

Chess.com's goal of 1,000 experiments isn't about the number. It’s a forcing function to expose systemic blockers and drive conversations about what's truly needed to increase velocity, like no-code tools and empowering non-product teams to test ideas.

Avoid the trap of building features for a single customer, which grinds products to a halt. When a high-stakes customer makes a specific request, the goal is to reframe and build it in a way that benefits the entire customer base, turning a one-off demand into a strategic win-win.

To ensure continuous experimentation, Coastline's marketing head allocates a specific "failure budget" for high-risk initiatives. The philosophy is that most experiments won't work, but the few that do will generate enough value to cover all losses and open up crucial new marketing channels.