The Best Time to Join a Startup is at the Worst Time
TL/DR: Would you need a jr. (or a team) to assist you in your work? Don’t join a startup. Is your highest value providing niche intellect to specific problems? Don’t join a startup. Want to be a fundamental part of changing the way the world works? Hop on board… Just don’t forget about those fundamentals.
Startups go through many different phases. We’ve been at it for over 4 years now and I can distinctly see three phases in our life. The latest being a fairly recent and big change.
These phases provide fundamentally different opportunities and work for employees. Which phase is the best for you will determine when the best time to join is.
If you care about pure financial gain you’ll want to get in early — The earlier the better as a general rule of thumb. If you care about solving interesting challenges that businesses only face as they scale, you’ll want to join later on.
The phases of risk, reward, and role are on a spectrum for a startup. Challenges you’ll be able to face in each stage are very different. In general, there are three phases which you can join a startup.
- Found a startup: big risk; big reward.
- Join a startup pre investment: slightly less risk; slightly less reward.
- Join a startup post investment: still risky (but way less risky); still some reward.
If you have any specialized skills, then joining a startup too early will leave you feeling under-utilized. In the early days everything is so general that few specialized skills are needed immediately — and if they are, the founders normally have enough of that covered to start. This is generally a startup less than 10 people.
Jumping in too late and you’ll feel like just another employee at a great company. You won’t be known as one of the initial members of the start-up, as in one of the first few at the company. You wont make the connections and the networks that the others have. You wont have deep personal relationships with the founding team. This might start happening at around 30-40 people.
So is 10-20 people a sweet-spot at joining a startup? It might be, but think through some basic questions first before signing up. Do you believe in their mission? The team? Is there a market? Are investors taking interest (if you care about quick growth)?
If it’s a yes for all of this, then perfect. Looks like the startup you’ve found is at the perfect stage for you to be one of the first great employees.
This is the best time for you to join.
This is also the worst time for you to join.
They’ll have a vision. They’ll have a team. They’ll have made some impressive progress. They’ll be great people. All is great!
But, they’re in an inflection point in their timeline.
For the first time they’re thinking through process. They’ll be thinking through budgets, through culture, through HR. That means these processes and functions wont exist yet. You’ll have to be prepared for some bumps.
The first on-boardings will be rough. The tools will be limited. The resources constrained. The problems won’t always be challenging — but they’ll will take hard work to finish.
You wont benefit from the mistakes of others because there haven’t been others. You’re one of the first. You’re the one who makes it better for the next. So, be open about your experiences and make every attempt to fix the issues to make the company better.
You are a trailblazer. This is how you significantly affect the company.
Your startup is still very much at war and you’ll be joining in mid fight. That means the expectation is for you to put on your boots and grab any old gun. There isn’t a lot of time for training or explanation…
Your skills and specializations are great. They’re exactly what the company needs. But it also needs a bunch of jr. tasks to be done — and you’ll be the best person for that job.
You’ll be a commander and a foot soldier all in one. You’ll prospect, decide on pricing, close deals, do customer support, and change pricing. You’ll have an idea, implement a feature, do QA, push it live, do customer support, and then re-implement it in a few months when you realize it was wrong.
@bhorowitz makes a great point when he talks about lead bullets. There aren’t any silver bullets that you can put in your gun to win the war, just a whole lot of lead bullets.
The benefit of being a commander/foot-soldier is that you control the movements of an army. You’ll be able to set the direction and implement processes you want, in a way that future soldiers will follow.
You’ll fix everything you hated about your last job. You can structure it in the way you would have always wanted it. You’ll use the tools you love and build a product, team, and company you’re proud of. You will learn. This is your Masters Degree.
Joining a startup between 10-20 employees is great. You’ll be the one solving the challenging problems as they come up and the interesting ones once you have time to focus on them. Your team will grow beneath you.
You’ve entered on the ground floor.
The problem is, the rest of the floors are still being built.
Here’s a quick TL/DR test:
Do you want to optimize the responsive layout rendering to simulate real magazine editors and curators? Or, do you want to build the first social magazine?
The first lets you think for months about an interesting challenge. The second lets you work for years on problems and, after lots of led bullets, lets you work on those hyper unique interesting challenges.
If you want the first; Work at a 170 person company that’s raised almost $1M per current employee.
If you want the second; Join a 10-20 person startup.
I actually don’t want this to turn into a recruiting post or anything. But we are hiring and we are building out the floors above us as we go. Let me know if you’d like to design your own suite by reaching out on twitter.
