So, you want to create your own startup? — Should you join an early stage startup first?

These thoughts are targeted towards engineers and product people coming from big tech companies like Meta, Amazon, Twitter, Salesforce, Snap, Stripe, etc. This will not apply to everyone but the logic can be applied to individuals looking to create a startup.

At a seed stage startup like Prepared, we want to bring in co-workers that are ‘entrepreneurial’ and ‘startupy’ in nature. Finding someone that can do the job is hard enough but finding one that is also entrepreneurial is even tougher. On top of this challenge, most of the entrepreneurial people are like “Why shouldn’t I just start my own startup?”

Below are some of my thoughts related to this.

Why create your own startup?

(Heavily Inspired from Dustin Moskovitz’s - Why building a startup? lecture and Notes). Dustin Moskovitz co-founded Facebook and Asana. I’d highly recommend watching his lecture first.

The standard reasons why people create a startup:

  • It’s glamorous
  • You’ll be the boss
  • Flexibility
  • You’ll make more money and have more impact
  • “If you don’t do it now, you won’t have another chance”

Creating a startup for any of those reasons alone I believe is a recipe for burnout. None of them hold up...

It’s Glamorous

False; It’s hard work, it’s stressful, and you can’t quit. You are at your desk, heads down, focused, answering customer support emails, doing sales, figuring out hard engineering problems, and putting out fires. Initially, you’re the only one that is keeping track of and putting out these inevitable fires.

You’ll be the boss

False; Every one of our customers, employees, and investors are now your boss — all in their own way.


False; You are always on call, as a technical founder this is quite literal. You are a role model, people replicate what they see you setting as the standard. You slack, they slack. You panic, they panic.

More Money

False; Watch Dustin Moskovitz's break-down on why more money is actually a facade and joining an early startup will earn you the same amount of money as founding your own.

More Impact

False; Impact of joining a seed stage startup can actually be higher as the idea has been de-risked. A startup that raised a seed round is more likely to succeed than one that has not. Thus, Most startups don’t raise a seed and thus have no impact.

If I don’t do it now, I won’t have another chance

This may be true, but is not the right reason to create a startup. FOMO motivation will die out quickly when working 80+ hours a week.

The right reasons to create a startup are:

  1. You can’t not do it because you’re so passionate
  2. You can’t not do it because the world needs it
  3. You can’t not do it because you’re the best person to do it

These reasons are incredibly true. For me working on Prepared, what keeps me going is the fact that the worlds needs what we are creating AND I’m incredibly passionate about the space + and idea. During the hard and stressful times, I think about the change that we are trying to create in the world and the stories of how our product helped enable livesaving outcomes for our customers.

The best way to get burned out is to not truly care about what you are are working every day on.

You will be working towards solving the same problem all day, every day. As a technical founder, you will perpetually be ‘on call’. As a founder, anytime an employee reaches out after hours, you will want to respond (and probably should in the early stages and given the new norm of async work). If you are not incredibly passionate about the work or motivated by the mission, you will be predisposed to burnout and not be able to exude the passion that is required to build and rally a team in hard times.

If you have an idea that fits even one of these 3 reasons, you should go all in. If you find a startup or company that also fits the reasons for you, consider joining them.

How does joining an early-stage startup help you become an exceptional founder?

We’ll start off with the cliché reasons:

Bring a product from truly zero to one.

At an early stage company, you don’t have a user base or resources to leverage. An early startup will teach you to think scrappily, see what doesn’t work, and figure out what does.

How to create an exceptional culture.

It’s hard to understand what culture means and how to create it. This is especially true when working in a big company. Seeing how that culture breaks down and is rebuilt at different stages of growth is crucial to long term success.

How to grow a product exponentially.

We are constantly iterating our framework of prioritization and our discovery engine. That is how to approach new features, new products, and even complete company pivots. On the technical side, that means building infrastructure from zero to one, and scaling that from one to exponential customer growth.

How to change things when change is hard.

There is a gap between theory and practice that you can only really fill with experience. We’ve messed up many times and will continue to fail, but each time we learn and are filling that gap. This experience is invaluable when creating your next startup — and at Prepared we’ve gone through his process more than a couple times (and failed more than a couple times already).

Disrupting an “un-disruptable” industry.

This is more relevant to Prepared. We’re thinking different on customer acquisition in the local gov-tech space, which hasn’t seen much VC innovation. This type of thinking differently to solve a problem only comes from putting yourself in a unique position and seeing how the pieces align.

An exceptional early stage startup will go above just the job. They should be trying to level-up the entire team through mentorship and transparency.

Access to Mentorship

We pair every employee with a mentor that is essentially them in 6 years. This is facilitated through our early investor First Round Capital. We found mentorship invaluable as it allows you to leverage the experience of someone who has been in your shoes before, has done what you want to do, and wants to help you figure out where you want to improve and which trajectory you want to go on.

Working with startup minded team

Every early employee at a startup should be capable of creating their own startup. We wholeheartedly believe this to be true, in general and at Prepared. Surrounding yourself with engineers, product managers, and executives that are extremely capable and share a similar mindset, helps you identify the archetypes of people that do and don’t work in different positions.

Though the hiring process, learning what types of people rise and sink in a startup becomes more and more clear. Identifying these traits early on in the interview process, and early into their tenure in the company, is key.

Understanding and Meeting Investors

An early stage startup should be incredibly transparent with how they approach goals and what investors are looking to see, for every quarter, year, and round. These goals change rapidly based on the market. Working in this environment allows you to understand what it takes to get funding, and what types of investors are the right fit. This is especially important given the current funding climate.

A good early-stage startup should have this radical transparency on investors’ expectations as it dramatically improves alignment of the team.

Prepared regularly host events with our investors, and our investors are an open book to our employees and potential hires. We regularly put our future hires in touch with our investors so they can vet what we are pitching. The investors like it because they know that every early employee at a startup is ripe to start their own in the future (and are scouting for future investments!).

Learning on someone else’s dime

Joining an early-stage startup lets you learn (and fail) on someone else’s dime.

Working with a small team, solving challenging problems, and being motivated the mission is everything you get out of being a founder without the risk. There is already a foundation to build off of, a network to tap into, customers to work with, and incredibly challenging problems ahead. No early-stage startup has everything figured out — the hard problems are head of them.

Almost all our engineers and early employees are “learning on our dime”. They have tried creating their own ‘startups’ in the past and expressed wanting to create their own startup in the future. They all plan on leaving at some point to create their own thing.

Right now, what motivates them is:

  1. The mission of our startup [in this case to build software that saves lives]
  2. The skills that they learned along the way will set them up for success.

Learning the theory in books and Y-Combinator videos is the first step, translating those ideas into practice successfully takes luck then experience.

An early-stage company has already de-risked a lot through funding and bringing on exceptional employees. If your goal is to learn and put yourself in a position to be more successful when you do take your shot at entrepreneurship, joining an early-stage company will set you up well to not fumble early on.

I can’t speak for all investors, but just as startups look for other startup people in hiring, early stage investors look for people that have proven they are fit for the entrepreneurial journey. Working for an early-stage startup, and being instrumental in their success, is a direct indicator of a person that is committed and has the skills to succeed (de-risking their investment).

So... should you create a startup or join?

That all being said, there is no better experience than jumping in and trying to create your own endeavor from scratch, and failing. Are able to put yourself out, ready to learn, ready to fail on your own dime, or do you want to fail on someone else’s.

If you have an idea that the world needs, you're passionate about, or no one else can do other than you, create that startup. Otherwise, if you find a startup that meets those criteria, join it and give it your all.

If you are interested in learning more about Prepared, feel free to contact me: neal @ prepared911 (dot) com and I’d be happy to chat!