The Ultimate Guide: Should I join a startup?

I’ve spent 7 yrs working for startups. Get the inside scope on the good, bad, and the ugly of what it’s like. Are we talking 🌈 & 🌹 or 💩📺 ? Read on to find out.

I’ve spent 7 years working for startups. 

I’ve heard all the 🌈 & 🌹’s stories as well as the 💩📺 ones too.

I’ve had my fair share of both – including one that almost went bust during covid, and another that grew faster than zoom and was acquired for $187,000,000. 💰💰💰

Unfortunately many people don’t go into joining a startup with a good picture of the reality of startup culture and end up confused and/or disillusioned.

I want you to be able to go in fully aware of what you are getting into – the good, the bad, and the ugly. I’m not going to sugarcoat it.

Do I love working for startups – hell yes!

Are there some downsides and hard things as well – yep.

Let’s dive right in to 6 things you should know before joining a startup:

1. Know what you are getting into

2. Know yourself: what type of work environment do you trive in?

3. Learn about the culture and products of the startup

4. Deep dive into their finances

5. Research their founders, investors, and advisors

6. Understand your equity options

1. Know what you are getting into

The good 🎉

Variety in your role

One of the things that I love about startups is how much variety you have in your day to day.

One day you’ll be on the phone with a customer working through an issue. The next you’ll be demoing a new product. The next you’ll be going through some fresh designs with product and the design team. The next you’ll be chatting through scaling problems after signing your first massive client.

There’s never a dull moment.

Chance of massive financial upside

Everyone likes to talk about this, but working for a successful early stage startup really can make you a bunch of money.

Startups usually pay you well for all your blood, sweat, and tears that you invest in them as they are rapidly growing the business.

Stick with them for 3-4 yrs, see them go through a big IPO, and you could be set for life.

Corporate red tape is kept to a minimum

Startups are like the opposite of corporate red tape. If anything there’s not enough processes and systems.

Move fast and break shi!t is their mantra.

• DM your founder because you don’t agree on something – totally fine.

• Use a different project management software besides JIRA – go ahead!

• Skip standup to go heads down to hit a deadline in a week – no worries.

Rapid promotions and career growth are common

A good startup is going to grow very rapidly. And if you grow with them, you will level up massively in your skills.

You could get promoted 3x in 3 yrs – like I’ve done before.

3 yrs at a startup is like 5-10 yrs at a big corporate company.

To read how I personally grew at the startup with a 9 figure acquisition, checkout my post on Linkedin.

Passion and talent abounds.

Learn and grow with some of the most talented and motivated coworkers.

Because of the massive equity upside, and rapid personal growth potential, startups tend to attract some of the brightest and most creative engineers in the industry.

You’ll also get to rub shoulders with incredible founders and industry leaders every day. It’s a really unique experience you won’t get at a larger company.

I learned so much about product, business, finances, engineering, customer experience, etc. just by rubbing shoulders with other incredible folks.

The bad 🤪

75% of startups fail

Uh yep, that’s the ugly truth about startups no one talks about.

Many of them never succeed. Either they don’t have good product-market fit, or the team can’t sell it.

There’s a 1 in 4 chance that startup you are eyeing succeeds. 😅

It’s super important to do through research on them before joining. I share more about that later on in this article.

Work / Life balance can suffer 

This isn’t true at every startup… I’ve been able to work pretty sane hrs at the 7 yrs I was at startups, but it was something I really had to be disciplined about.

The workload will be endless, so you’ll need to be great at time management, taking breaks and saying no.

Otherwise, your work / life balance can really suffer.

Unhealthy leaders can damage the team

Because startups are usually very small, negative personalities can have a much bigger impact on the team – you can’t get away from them.

I saw that at one startup I worked at… the founder was literally driving the team into the ground… err… actually into leaving.

Formal mentorship and growth paths can be lacking

I’ve grown my skills massively by working at startups for 7+ yrs.

But the reality of it is that a lot of my growth was self-directed. That can be hard for folks who crave more structure, and need more external guidance for growth.

One of the startups I worked at literally didn’t have a career ladder. I had to push for yrs before they developed one, and outlined what I needed to do to get a pay raise.

That was frustrating to say the least.

A startup won’t usually standout on your resume like a big tech job

Unless it’s a unicorn startup like Ramp, Stripe, WhatsApp, or Uber, it’s not going to standout on your resume like working at a big tech company will.

Recruiter: Oh you’ve worked at Amazon, Google, and Facebook? Cool, you probably have a lot of good experience and engineering practices.

Hmm… you worked at Loon… what is that? Oh a failed balloon internet startup?

It won’t have the same Punchh… (restaurant startup pun… sorry couldn’t help it)

If you learn how to quantify your skills and learnings, you can totally showcase your experience and skills even from failed startups. It’s just not going to be a give-in.

The ugly 💩

Oof, now we peel back the onion and talk about realities that are dark secrets in the startup world. Let’s tread in carefully…

Not all startups will have the bad and the ugly, but you should know it’s a possibility.

Burnout is common

Many startups praise people who hustle like Elon Musk… let’s crush nights and weekends, this is our one chance to make a billion dollars.

That can only last so long, before burnout happens.

I’m not against working hard, I love to work hard, and even do nights and weekends often on my side things I’m excited about.

But what I am against is treating your employees like part of a machine – instead of valuing their humanity and caring for their physical / mental health and well-being.

Your equity could be worthless

I think this is one of the least talked about downsides of startups. Many times people pour years into a startup only to have it never really take off…

Which means their equity is worthless.

I heard of someone who literally got .34 cents on a check from a startup payout 😱

Reality of companies finances sometimes not acknowledged

We only need to look at most of the crypto companies of 2020/2021 to realize that the finances of these unicorn startups is not always what they appear to be.

FTX, the crypto giant that everyone was investing in is a prime example.

It was touted as being the safest company with so much in reserves… Turns out they were literally counting 8 billion dollars twice on their balance sheet. 🤯

People lost a lot of money investing in them. Including Tom Brady who lost 30 million.

“Just ship it” can breed spaghetti code

Speed is often key when you are working to quickly get your app in users hands. This is fine and good, but there comes a time where you need to focus on things like:

– Maintainability, Scalability, Readability, Extensibility, etc.

If you never refactor and clean up the mess, it can lead to spaghetti code which can be a nightmare to work in years later.

16,000 line php files, and functions with 20+ params were some of my favorite. 🙃

Constant priority changes can lead to mental health issues

You just signed the biggest client your team has ever signed – yay!

However, they immediately ask for 5 new features, which the team feels pressure to act on. Bye-bye 6 month roadmap, and hello constant priority shifting for the team.

This is a hard place to be in.

I almost burned out myself from this at the company I’m currently at. The constant priority and context shifting takes a big toll on the team.

2. Know yourself: what kind of environment do you thrive in?

Joining a startup sounds really sexy, but it’s not for everyone.

If stability, and predictability is your jam – a startup is probably not for you.

Here are some characteristics that may be true of you if you would enjoy working at a startup:

• You enjoy taking risks

• You prioritize action over perfection

• You thrive in a fast-paced work environment

• You get bored easily if there’s not enough to do

• You are willing to do things that “aren’t your job”

• You don’t struggle with self guidance if there’s ambiguity

• You want to learn about how business, product and sales work

• You prefer flexibility and freedom over lots of structure

• You question how things have always been done

• You want to work closely with your customers 

• You are a generalist with many broad skills

• Move fast and break sh!t is your jam

• You like to build, not just maintain

Not all these have to be true of you to join a startup and enjoy it, but you should know that it’s not going to be your typical 9-5.

You won’t just be coming in to knock out Jira tickets that are perfected scoped, articulated, and planned.

Startups have a lot of change, ambiguity, and ”figure it out as we go”.

Depending on what you like, it can either be super fun or super draining.

3. Learn about the culture and products

There’s a lot of risk when you join a startup.

Sure there could be massive upside, but they could also crash and burn and you’d lose all your equity and blood, sweat, and tears you poured into them.

Before you join, do a ton of research on the startup, their culture, their products, how they invest in their people, what their finances look like, and how you will be compensated.

Here is just a sample of some questions I’ve found very helpful.

Engineering focused questions

• What is your team’s biggest current challenge?

• What types of engineering problems are you facing these days?

• What do you see as the engineering team’s role in the company?

• Why are you hiring for this role – what is the one problem you need to solve?