Should You Join a Startup? Questions to Ask First
I left a great job to help run a startup, pulled from my savings to buy in and signed the office lease. It was one of the best decisions I have made, and it was not the right move for everyone.
Before joining a startup, ask yourself how much financial risk you and your family can handle, whether you believe in the founders and the product, whether you are comfortable with uncertainty and wearing many hats, what you would learn and what happens if it fails. Ask the startup about funding, runway, how decisions are made and what success looks like. Join when the learning and belief outweigh the risk for your situation.
I had a great job at a company I loved, working with people I enjoyed. I could have seen myself retiring there. Then I decided to go to a startup with no processes and no training manual. I pulled from my savings and retirement to buy ownership, and I signed the lease on the office, which meant I was liable if anything went wrong. If things went badly, it would affect my family.
It turned into one of the most important decisions of my career. But I would not tell anyone to make it without thinking carefully first.
Questions before you join a startup
- What can my family afford to risk? Be honest.
- Do I believe in the people? Founders matter more than plans.
- Am I comfortable with uncertainty? Every day will be different.
- Will I wear many hats? And do I want to?
- What will I learn? Growth is often the biggest return.
- What happens if it fails? Have a plan.
Know your risk
Startups can fail, and many do. Think honestly about what you and your family can handle if pay is lower, equity turns out to be worthless or the company closes. If your savings are involved, as mine were, talk it through with the people it affects.
Believe in the people
In the early days, a startup is mostly its people. Do you trust the founders? Do they treat people well? Will they be honest with you when things get hard? You can have a great vision, but if people do not believe in the person, they will not buy into the vision.
Ask the startup hard questions
Ask about funding, how long the money will last, how decisions are made, what success looks like in a year and what your role would really involve. Good founders will appreciate thoughtful questions.
Count the learning
Wearing every hat and learning roles I had never done made me grow in ways I never would have otherwise. For many people, the learning is the biggest return of all.
Betting on yourself is part of my signature keynote, You Are Capable of More. See also How to Bet on Yourself and Leadership Lessons From Running a Startup.
Joining a startup can accelerate growth, and it carries real risk. Be honest about what your family can afford, believe in the people, ask hard questions about funding and roles, count the learning and have a plan if it fails.
Frequently asked questions
Should I leave a stable job for a startup?
What questions should you ask before joining a startup?
What are the benefits of working at a startup?
What are the risks of joining a startup?
You Are Capable of More
A No-Excuses Guide to Becoming Your Best Self. The bestselling book behind Chris’s keynotes and the 2026 Paris Book Festival winner in the How-To category. Many teams hand a copy to every seller at their kickoff.
Bring this to
your team.
Chris Sund speaks on this in You Are Capable of More, for conferences, leadership teams and company meetings.
Keynote, breakout or virtual · Response within one business day
More About ChrisInc. ArticlesForbes CouncilBook Chris to Speak