So You Think You Want to Join a Start-Up? Here Are 10 Things to Consider Before You Do…

“What would that experience be like? Getting in on the ground floor, the excitement of a new product, software, or solution, the unknown, doing whatever it takes, the super fast growth….Could I handle it? Would I like it? Or would it feel like too much of a risk?”

Those were my thoughts exactly. I was in a job I liked making a salary I liked, but given some recent changes at the company, I was open to looking for my next opportunity. 

It was an imperfect decision-making process: it came down to taking a calculated risk, with eyes wide open, and having a healthy sense of adventure. 

Below are the things I considered before making the jump, and many of the things I learned about start-up life while living it to help you make this decision for yourself!

1️⃣ Who is the founder?
This is the most important question. There is a way in which picking who you work with and who you report to are always at the top of the list. Right? We want to like who we work with, be able to learn from them, and feel we are treated well. 

One of the things you quickly learn in the start-up world is that everyone is betting (or not betting) on the founder. The earliest employees and the earliest investors’ most important job is to assess the strength, skill, intelligence, character, vision, effectiveness, and resiliency of the founder in determining whether to engage with a start-up. 

This is a hard journey. Start-ups are small. You’ll work REALLY closely with the founder. Take this part seriously. (Photo: Dawn, Jottful’s founder, scores high! ⬇️)

2️⃣ Do they have a cool idea or are they solving a market need?

One way to assess the founder is looking at what they are creating. Are they technical and have they created a software or hardware solution that they think is incredible and they just know people will buy? The “build it and they will come” model. 

Or, did the founder see an unmet need in the market, talk to people in that market about their potential solution, test it, and develop their solution to solve that market need. The “find a problem and solve it” model.

You’ll want to work for a start-up founder who followed the second model. Very early on, the most important thing to do is determine product-market fit. Founders who fall into the second model approach the founding of their business with this in mind.

(Photo: In Jottful’s case, Dawn identified the market need - small business owners still did not have a simple, affordable, effective solution for their business website. ⬇️)

3️⃣ How is the Start-up Funded? 

It’s rare that a start-up doesn’t need outside funding to get started. It’s possible the founder was already a successful business owner elsewhere or comes from wealth, and is self-funding. But, more often, funding will come from other sources. Incubators, accelerators, early angel investors of friends and family. Learn what you can about the funding, so you can assess your risk - how long will this funding last? What is the plan for raising more money? If there is no funding, be prepared to work for very little or for free, and be offered equity in return.

4️⃣ Let’s Talk About Equity

I was new to equity. It’s important in the start-up world. If you’re thinking of joining one, you’ll need to expect a lower salary than you’re used to. Even if a start-up has some funding as noted above, it’s going to take time for the business to be profitable or for enough funding to come through (repeatedly) to pay market salaries. 

So, if you’re very early in a start-up, you’ll want to ask for some compensation via equity. There is a lot of information on this topic. Here is a solid article to help you assess what equity would make sense for you if joining a start-up. 

5️⃣ What is the Work That is Needed? 

More technical founders, like those in model one from point 2 above, will need engineers and designers. They start by building. BUT, I don’t care who you are, any founder will need to figure out the market, promote their solution, make sales, serve customers, and test over and over again. 

So, ask the founder what is needed. Look at the list of tasks. You will have to wear many hats. You will have to do things you don’t want to do. You will have to do things you don’t know how to do.

Are you okay with the work at hand? And, if so, for how long? (Photo: Our UX design intern, Linde, whose design and font choices still exist in Jottful’s product today! ⬇️)

6️⃣ Titles don’t really mean anything in the start-up world (other than CEO)

Titles are funny things. When you’re early in your career, titles matter more since they’re an outside seal of approval on your skills and your level of expertise.

You may always be someone who wants a C in their title or a Director in their title. Or, you may care very little about titles. 

Interestingly in the start-up world, titles can go either way. Some founders gives important VP or C-level titles to entice early employees to join, knowing that they can’t offer much else. If you can’t live up to the work expectation of a big title, that could be demotivating or stressful for you. 

Another option: you can work out a title with the start-up that best describes your general focus, and change the title when it makes sense to do so. Make your title broad enough to cover a myriad of work you might do. There is typically a lot of flexibility with titles in start-ups. 

7️⃣ Be willing to do any work - whatever it takes

If you’re joining a start-up, you’ve assessed that the work that’s needed falls reasonably within your skillsets and interests. But, there will be so much else - guaranteed. Roll up your sleeves, find ways to help, learn new skills, watch YouTube videos, try stuff, be okaying sucking at things for a while (but learn quickly) and just jump in to help. 

Are you ready to feel like a beginner over and over again? (Photo: sometimes, you’ll have to rent games from the library and cart them to your office for a party! ⬇️)

8️⃣ Change is the norm

No one has it all figured out. The beauty of the start-up journey is one of exploration, learning, and growth. Expect change. It could be a change in direction, a change in marketing strategy, in which industries you want to serve, even changes to the product or offering. If you are not someone who likes or thrives on change, a start-up is a hard place to be. If you enjoy change, are flexible, like to try things, or consider yourself adventurous, the start-up experience may be a great fit for you!

9️⃣ Living with uncertainty

Any business owner knows this uncertainty. However if you are an early-stage start-up employee, you will know it too. As of 2023, the current failure rate of start-ups is 90%. You read that right. You will feel this uncertainty almost daily. It will affect your decision-making in many areas of your life. 

If you’re deciding where to live: in an apartment, or buying a house, you’ll pause and feel the uncertainty. If your partner is looking to leave their job, you’ll take more time to think through “what if” options. You’ll find that you make larger life decisions within about a 6 month window, and not much further out than that. 

Can you live with this kind of uncertainty?

*Jottful successfully passed the start-up stage, making it into the top 10%!*

🔟 Time, Patience, & Money

You might have guessed it after reading, building a business takes time. Everything will take longer than you expect it will. Figuring out how to market to the right customers will take much longer than you expect. It will take time. It will take tons of patience. And, it will take money. What do I mean by this?

If you’re joining a start-up, you’re likely to make less than you would at a more established company. That may be true for longer than you expect. You better be prepared for it. Assess your savings - do you have more than enough savings to take this risk? Do you have a side-hustle or an evening or weekend job that can help you supplement your income?

Get clear about how much time, patience, and money you would need to feel comfortable taking the risk of joining a start-up. 

What do you think? Are you ready to join a start-up?