Should You Start a Startup? Read This Before You Decide.

I've sat in every seat at the startup table: VC, founder, angel, and advisor.

Over the years, I've seen what happens when people jump into entrepreneurship at the wrong time, or fail to make the leap when the time is right.

If you're reading this, you might be somewhere in the middle.

Maybe a friend started a company and you've been watching from the sidelines. Maybe you've had an idea rattling around for a while and you can't tell if it's worth pursuing. Maybe you're just trying to understand what the startup world actually looks like from the inside, before you decide whether you want in.

If you’re asking yourself if you should start a startup, this newsletter is for you.

Before we dive in, here is an important distinction to understand: There's a big difference between starting a business and building a high-growth technology company.

Drop-shipping, freelancing, e-commerce, online courses are all legitimate business paths, but they are not the same as building a high-growth tech startup. We're talking 10 or more years of your life, outside capital, sustained uncertainty, and no guaranteed paycheck.

If what you're considering falls into that second category, here are the 4 questions I'd want you to answer honestly before you make the leap.

The founders who succeed aren't just passionate about a problem. They have a genuine, hard-won advantage in their space.

That means one of two things: You're a technical expert who can build the product better than anyone else, or you're a deep domain insider who understands a specific vertical with more nuance than any outsider could acquire through research.

I've watched founders try to build companies in industries they studied rather than lived. It rarely works. The market is too complex, the sales cycles too long, the buyer relationships too difficult to establish without years of real experience.

My co-founders in CodaPet have over 30 years of experience in petcare. That wasn't coincidence. That was the foundation.

Studying a market isn't enough. You need to have lived it.

I don't mean this in the thrill-seeker sense. I mean it in the most practical, day-to-day sense.

You will hear "no" from investors you respected. You will lose customers to competitors due to price. You will make a key hire that turns out to be wrong. You might choose the wrong technical architecture, the wrong go-to-market strategy, the wrong co-founder.

None of that disqualifies you. What disqualifies you is not being able to keep moving after it happens.

The founders I back are rarely fearless. They're scared plenty. What sets them apart is thick skin and the ability to make calculated decisions when every path forward is uncertain. That's a skill. And like most skills, you can develop it — but you need to know going in that it's required because there will be countless setbacks.

This one doesn't get talked about enough.

The same person can be completely ready to start a company at 24 and completely wrong for it at 32 — not because they've gotten worse, but because their circumstances have changed. A mortgage on a big house. Young kids. A partner who doesn't have employer-sponsored health insurance. These aren't excuses. They're real constraints that affect your ability to take the kind of sustained financial risk and time commitment that a startup requires.

When you're younger and without dependents, you can live on less, work longer hours, and absorb failure more quickly. When you’re older, you might have more domain knowledge and/or personal savings in order to bootstrap your startup. That's a genuine advantage.

Timing in your personal life matters as much as timing in the market. Be honest with yourself about where you actually are.

Webvan raised $375 million in 1999 to solve grocery delivery. Within two years, it was bankrupt.

Instacart launched in 2012 and went on to be worth more than $10 billion.

Same problem. Different timing. Equals completely different outcomes.

The difference wasn't the idea. It was the infrastructure: smartphones in everyone's pocket, GPS-enabled gig workers, consumer comfort with putting credit cards into apps, and the collapse in the cost of cloud computing. None of that existed in 1999. All of it existed in 2012.

Market timing is often outside your control, which makes it easy to dismiss. Don't. It's worth asking honestly whether the technology, the consumer behavior, and the economic conditions are aligned to support what you're building right now — not in theory, but today.

There are real ways to test your readiness without going all in.

Advise or consult for startups in adjacent spaces — not direct competitors. Offer your time for free. If you believe in the space, put skin in the game in the form of time or a small angel check. This tests whether you can actually sell your ideas and add value, which is a core founder skill.

Try intrapreneurship. Join an innovation team or a new business unit inside a large company. If you can't convince people inside an organization to bet on your ideas, that's useful data about how you'll do on the outside.

Run it as a side hustle. Work nights and weekends on the problem while keeping your day job. This builds stamina, validates your capacity to sustain 10-to-12-hour days, and forces you to prove the concept without financial desperation driving your decisions.

Start with services, not software. Solve the problem manually, one customer at a time, before building a platform. Find early design partner customers. This is how you learn what the product actually needs to be.

98% of founder life is unglamorous, repetitive, and stressful. The founders who last aren't chasing the cover of a magazine or trying to be the next Mark Zuckerberg. They're solving a problem they can't stop thinking about, in a space where they have a real edge, at a moment in their life when they can actually absorb the risk.

Starting a high-growth tech company is a demanding path. It's not for everyone. That's not a criticism against you, it's just reality.

If you can answer yes to all four questions above, you're in a strong position to take the leap. If you can't, that doesn't mean the answer is never. It might just mean the answer is not yet.

Are there criteria I missed? And for the founders reading this, which one was hardest for you to honestly assess?

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