So You're Interviewing With An Early-Stage Startup

"The best way to find out if you can trust somebody is to trust them." - Ernest Hemingway

So you’re going to interview with an early stage startup. I understand, the job market has been rough for years. AI that isn't yet ready to replace humans has fueled a culture of hiring hesitation, just in case it suddenly gets better. The economy? Still bad. That's why you're now willing to talk to a 40-year-old who acts 20, about a job at Blookmaret LLC, a company with no revenue, no funding, no product, no customers, and no clear vision.

Everything about the startup may be a red flag, but after 1,000 applications to ghost jobs, a live interview can feel like a refreshing breath of sanity. Still, working at a startup doesn’t just mean risking chaos, you also risk not getting paid. And no money for no labor is better than no money for labor, followed by legal action to recover what you were promised. Here are the questions to ask to avoid falling into the early-stage startup meat grinder.

Who is the Company’s Attorney?

This is not a trick question. The company has an attorney they work with, perhaps many, or they do not have any. An answer like Ashley Smith is who we have worked with in the past, is probably fine it means the founders of the company have at some point talked to an attorney.

A better answer sounds like this: “We retained Ashley Smith as fractional general counsel; Jim Doe from Doe, Zim & Heart handles our IP; and Amanda Kim is advising on due diligence and fundraising.” That response signals professionalism. It shows the company isn’t running purely on founder whims. It means contracts aren’t being drafted by ChatGPT, and employment law isn’t being interpreted through episodes of Suits or Boston Legal.

The worst answers dodge the question: “We had someone help us incorporate,” or “I don’t remember.” Those are red flags. Someone is not doing things by the book and hiding it.

If someone simply says “We don’t have an attorney,” that at least shows honesty. But if you have any business experience, you’ll know what’s coming: you’ll end up doing legal work that’s outside your job description, and you'll eventually clash with the founders when you do. It’s much easier to defer to legal counsel (even when you know the right answer) than to explain why using Mickey Mouse in a marketing campaign isn’t “fair use,” and is a blatant trademark violation sure to trigger Disney’s legal team.

Basic Questions

Truly, the number of basic business questions is endless, and all of them should have simple or at least straight forward answers.

Structural

• What is your current legal structure, LLC,C-Corp, &/c?

• Why was this structure chosen at this stage?

• Where is the company filed?

• Do you have a formal Operating Agreement or Bylaws in place?

• Can I see a summary of key terms related to ownership and decision-making?

• Do you have professional liability insurance?

One of my favorite questions for very early-stage startups aiming to raise venture funding is: Have you thought about who you want on the board?

Almost every startup seeking VC funding ends up with the same basic structure: a Delaware C-Corp with a five-person board. Two directors are chosen by the founders, two by the investors, and the fifth is mutually agreed upon.

Other structures can be used, but if someone doesn’t have a reason for why they are the exception, or doesn't know the typical structure for VC backed companies: run. It’s not your job to advise, you are in an interview, and it is time to go.

Financial

• Have you raised capital, and if so, how much and from whom?

• How long can you operate with your current resources?

• Is there a clear strategy for securing more capital if needed?

• What is your fixed monthly burn rate?

• Do you have any revenue, if so, how much, and from what sources?

• Can I see your financial projections?

Every one of these should have an answer. Some are just numbers. Others might be more complex. Watch for evasiveness. Take notes. Ask again later to see if the answers change. Lies have a hard time staying consistent.

Last year, I had lunch with a startup founder. I should have left cash on the table to cover my meal and walked out based on how he answered just a few of these. The company was bootstrapped. He claimed he’d put in $2 million of his own money over the past five years, and that they had revenue of around $800K last year, but said he’d need to check with his cofounder on that number.

That wasn’t the only red flag, but it’s the one where I should have left.

The guy was probably a millionaire, sure. He was not worth $20 million. If he really put $2 million into the business, (more than 10% of his net worth) he’d know the revenue number. He wasn’t Brad Feld. He wasn’t Mark Cuban. Something was off. And I didn’t need to figure out what. I just needed to GTFO.

These Are First Meeting Questions

There are plenty of articles out there about what to ask before you accept a job—questions about compensation packages, team dynamics, company vision, mission, all that. These are questions you ask just to decide if it’s worth your time to keep talking.

Because showing up for an interview, even a casual one, is an investment. Approach these conversations like a detective, not a job seeker. You're gathering intelligence about people who want to purchase your time, skills, and network. Far too many early-stage startups are ideas with no infrastructure, no funding, no plan, and will use your time, skills, and network, as if you’re a cofounder before ghosting without ever paying.

Ideas are worth nothing. Execution is everything. And if they can’t answer the basics, don’t stick around to hear the pitch. You’re not their therapist. You’re not their lawyer. You’re not their free labor.

Don’t fall to the trap of believing you can turn things around, add the professionalism, and unlock the value. You cannot. Some people will not let you.

Ask the questions. Watch how they answer. Decide if you're walking. Keep in mind the Ernest Hemingway quote, "The best way to find out if you can trust somebody is to trust them."

Edited a typo shortly after posting.