Questions I Ask Myself When Starting a New Venture

A friend of mine recently left his corporate job to figure out what's next. He came to me with a handful of ideas and companies he was considering, and asked what I thought. Rather than give him a quick take on each one, I figured I'd put together the questions I actually ask myself when I'm evaluating whether to start or join something new.

This isn't a perfect list. But it's a good starting point, and it's how I think through these decisions. For context, one of the companies he was looking at had an early stage product, so a lot of what follows is rooted in product and startup thinking.

Does this product have product-market fit?

This is the first thing I want to understand. PMF really comes down to two pieces: the product itself, which needs to solve a real problem, and the go-to-market strategy, which needs to actually reach the people who have that problem.

The tricky part is when you're trying to figure out both at the same time. Is the product not working because it's the wrong solution, or because it's not getting in front of the right people? That's a hard question to untangle. My general approach is to nail the product first, then figure out distribution. And the shortcut I like to take is starting with a problem I'm intimately familiar with. When you don't know the problem space well, you end up stumbling through it. When you do, a lot of the early decisions become much clearer.

What stage is the company in?

This matters more than people think. An early-stage company that's still validating its core idea needs a very different kind of person than a company that's already found its footing and is trying to scale.

If you're joining at the ideation stage, the work is messy. You're operating with ambiguity, limited resources, and a lot of unknowns. Creativity and problem-solving matter here. You need to be comfortable iterating fast and being wrong a lot.

The growth stage is a different animal entirely. The product direction is more or less clear, and now it's about operational efficiency, building processes, managing a growing team. I find that people who are strong operators really excel in these types of orgs. The path is set, and the job is optimization.

So it's worth asking yourself: which of those environments do you actually want to be in? Not just which one you're good at, but which one do you enjoy? That distinction matters.

Is the product defensible?

Here's something I think about a lot. When a business is easy to start, it's usually hard to sustain. The digital marketing space is a good example. Anyone with some social media skills can mimic a successful model, and the barrier to entry is basically zero. Same thing with e-commerce. Cloud computing, Shopify, Stripe, these tools have made it incredibly simple to launch an online store. That's great for getting started, but it also means thousands of other people can do the exact same thing. The ease of starting a business tends to be inversely proportional to the difficulty of making it really successful.

I put together a list years ago about what makes a business defensible, and I still think it holds up. First, accept that no business is fully defensible. That's just reality, and you should be able to talk about it honestly with investors. But there are things that help. A head start over competitors gives you a time advantage, and moving faster than your rivals compounds that edge. Having a strong team with relevant experience matters, because investors and partners can see the difference. Economies of scale help too — as you grow, you get more leverage and lower costs. And then there's brand. A brand that connects emotionally with people is really hard to replicate. Think about Apple. You can copy the product specs, but you can't copy the feeling.

Does it seem like a good idea?

This one sounds simple, but I think it's underrated. I really like to thin-slice ideas. If something feels off in the first few seconds, I've learned to pay attention to that. Your gut is processing a lot of information that your conscious brain hasn't caught up with yet.

When I joined Urban Teachers, I just knew the idea was good. I'd spent years working with teacher training programs, and everything about the model made sense to me. We ended up scaling that company significantly over the four years I was there. With Eddee, it was the same feeling. I have deep expertise in the space, and the go-to-market path is clear. When those things line up, my gut usually says make the leap.

Understanding how you feel about something isn't soft or unscientific. It's data. And if you're going to spend the next few years of your life on something, you should actually believe in it.