Is the startup life right for me? It’s a question we hear a lot and one that many of our mentors have asked more than once throughout their early careers. For good reason! Joining startups can be as thrilling as it is nerve-racking. As one mentor put it, “It's a world where quick actions meet significant opportunities.” 

Whether you’re fresh out of school, looking to make a career shift, or already choosing between a few startup offers, deciding to join a startup can be tricky. How do you evaluate the upside and the risks? What factors should you consider? We asked these questions to a few mentors who have taken the startup leap. Here’s their advice.

‍

Reflect on your motivations

Start with self-reflection. When deciding to enter the startup world, our mentors recommend thinking about your motivation. What’s your “why”? Ask yourself these questions from Kat Fergerson:

What are my goals for learning and growth?

Startups tend to have faster learning curves because you’ll have tons of agency over what you’re doing. You’ll often be pushed to learn new skills and dive deep into unexpected areas. While this type of learning can be very rewarding, it is often far less structured than the type of learning at a larger more established company. Where you might have 10 leaders and mentors to learn from at a big company, at a startup you may only have 1. 

How much tolerance for risk do I have?

Depending on the stage, startups can be a lot riskier than working for an established business or organization. A recent study found that 90% of start-ups fail! What tends to be true is that the earlier the company, the greater the risk. Ask yourself if you are at a point in your career and life where you’re willing to embrace more risk and potentially less job security?

Am I bought into the company mission?

It’s critical to evaluate how the startup’s culture and vision align with yours. When you’re motivated by the company mission, the work is much more fulfilling and you are often more motivated. You’ll be diving deep into a niche. Make sure you believe in it! 

Is my priority to make a lot of money?

Kat recommends being cautious with this question. While some people can and do make a lot of money on startups through exits or IPOs, she warns that short-term financial returns should not be your primary motivation for joining. The amount of money you make can also depend on what stage startup you’re joining. Later-stage and growth-stage startups often offer very competitive salaries. Think about your short-term and long-term financial goals. 

‍

How to choose the right startup stage

The next thing to consider is startup stage. Depending on the stage of the startup you’re considering joining, your experience can greatly vary. Harry Siggins’ advice is to match your choice with your comfort for risk and your career vision.

Early-stage startups are often intense and demanding, requiring a more versatile skillset. Mid-stage startups are focused on growth and scaling and you’ll face challenges around adapting what has worked. Late-stage startups are often more structured, and you’ll be focused on driving towards major goals like an IPO.

Here are some questions from Kat that can help you narrow down which stage startup might be your best fit.

• Pre-Seed 👉 Do I care about the mission of the company? Can I see myself building for several years and taking the initiative to hit our goals? There is little structure and you’re usually proving the thesis of the company at this stage. You’re doing a lot of different jobs in one!
• ‍Seed 👉Can I work autonomously and build from 0 to 1? Your role may get more specific, but you’re still building from the ground floor at this stage. 
• ‍Series A 👉 Do I want the opportunity to take a company from 1 to 10? You’ll see more processes being built at this stage to help with growth.
• ‍Series B+ 👉 Do I want a more defined role within an established and growing startup? You usually have more stability–and structure–at this stage and beyond.

Evaluating a startup: what to ask during your interviews

Not all startups are created equal, so you’ll want to make sure you’re doing your due diligence as you evaluate which startup to join. Asking questions during your interviews is a great way to do this. Here are some questions Harry and Kat suggest asking:

• How much runway do you have, including planned increases in burn (future hiring plans)?
• What is the startup's financial health? 
• What was the pre/post-money valuation of the company at the last funding round?
• When are you planning your next raise?
• What goals do you need to hit in order to raise?
• What percent interest in the company would my options grant represent? 
• How are decisions made in the company?

Interviewing with a startup is about determining fit–both for the company and for yourself. While it may seem awkward or difficult to ask some of these questions, they are crucial pieces of information to gather to help you make an informed decision. You can also do some desk research by looking for financial information through investor profiles and funding stages, if available.

One other thing to pay attention to is the founder. It is critical to join a startup where you trust and believe in the founder as they will be setting much of the vision for the company. If you’re able to speak to them during the interview process, try to get to know them as a person and a leader. Are they someone you could see yourself following?

‍

Advice for landing a position at your dream startup

So, you’ve found your dream startup. Now you have to make your case. In general, the same interviewing tips apply to startups as they would to any other job you’re interviewing for. Harry’s approach is to think about the story behind your role. Why now, and why is it crucial? Crafting a compelling story about the value you’ll provide for the startup and why it’s essential to its success will help you put your best foot forward.

‍

Talk to people who've taken the startup leap

When making any difficult decisions, a conversation with someone who has experience making those decisions can be invaluable. Reach out to people in your network who have worked for startups. Listening to their stories can help give you the data points you need to make an informed decision that will set you up for success. 

Want to talk to a twenty mentor? That’s what our mentors are here for! twenty helps young adults navigate their twenties, personally and professionally. We connect you with highly-vetted mentors and a thoughtful community to help you carve your own unique path.