I've been working with a B2B founder who's built an AI product, and they're stuck with an interesting dilemma.
They started strong with startups but got tempted by enterprise dollars. They landed a nice five-figure pilot with a big corporation, but here's the catch: these corporate users barely scratch the surface of what the product can do. They stick to basic prompts and seem lost when it comes to AI interactions. Sure, they're wowed by simple outputs, but they're not really diving in – and it shows in their usage numbers.
Meanwhile, there's this startup customer who totally gets it. Their team is AI-savvy and uses the product in ways that push its limits. They're so invested they want API access to bake the product right into their systems.
The founder has enough runway (24 months) but a small team. Now they're facing a fork in the road:
Do they chase:
- The enterprise deal, which promises big money if the pilot works out, but needs tons of hand-holding and dumbing down the product?
- Or double down on the startup customer, who's showing what the product can really do and has cool integration ideas, but can't match the enterprise-level cash?
This isn't just about the next quarter's roadmap – it's about who they want to be as a company.
Better Clients
Seth Godin has been talking about choosing your customers for 15 years. Here's his most recent articulation.
"Advancement doesn't come from working more hours, it comes from securing better clients. Better clients talk about you more, return more frequently, pay you more, and create more demand for your work. However, you don't attract better clients by doing excellent work for poor clients; you attract them by creating conditions that make them seek you out."
How good are the best burgers in Chiang Mai? How do you think they stacks up against the best burgers in San Francisco, which boasts the most burger vendors per square mile of any U.S. city?
San Francisco consumers have a far higher bar for what makes a great burger than the hungry, tired ex-pat looking for familiar food in a foreign place. And so if your burger is not good in SF, you’re not going to sell very many.
The Snowball Effect of Early Customers
Here's the thing about chasing big money while trying to stay true to your product vision: it rarely works out the way you hope. Their complaints and ideas always end up in your product somehow, it’s just human nature.
Your early customers don't just influence your product roadmap – they shape your company's future. Think about testimonials and case studies: they attract similar customers. If you do great work for a customer who barely uses your product's potential, guess what? They'll refer more customers just like them. But work with innovative, demanding customers who push your product to its limits, and they'll bring similar forward-thinking clients your way.
I've seen this pattern in my own coaching practice. When I work with a founder navigating a transition, they tend to refer other founders in similar situations. Same goes for companies going through pivots—they connect me with others doing the same.
The customers you choose early on have a snowball effect on your company's trajectory. While it's tempting to say yes to everyone when you're starting out or going through tough times, you might end up stuck serving a market that doesn't align with your vision.
By choosing better clients. More demanding clients. More values-aligned clients. You find partners who will stretch your capabilities and sometimes make you uncomfortable—and in the end, help you build something truly remarkable.
