(~ 3 to 5 minute reading time)

Welcome!

Today, I’ll be sharing the 5 main reasons that made me realize taking a job at a startup was an obvious professional choice. Hopefully this post alongside this earlier one, help give a little more background information on why I’m so enthusiastic about this space!

Now, let’s jump into it…

TL;DR: Why Join a Startup?

Note: I always include the TL;DR at the beginning, in case you don’t have time to read on!

1. You Have Entrepreneurial Dreams

   1. It’s intuitive: If you want to be a startup founder down the road, you probably need some experience working with startups

   2. Entrepreneurial co-workers: Your startup co-workers are more likely to become your co-founders as opposed to your co-workers at a larger company

2. You Want Close Proximity with the Leadership Team

   1. Access to the big dawgs: A smaller team means you get more exposure to founders, execs, investors, and other crucial parties

   2. You get to be in the room: Startups give young employees more freedom to participate in discussions and voice their opinions

3. You Want a Measurable Impact

   1. Comparison to big companies: The hard work you put in can be missed at a bigger organization

   2. Getting paid: If you want to get compensated to the level you believe you deserve, go to a startup where it’s obvious who is doing the work

4. You Want Outsized Wealth Creation

   1. Equity: Owning a part of the business is a fundamental pillar of wealth creation and startups can offer you this

5. You’ll Still Need to Weigh Other Career Options

   1. I chose working at a startup over investment banking, consulting, and service programs. What will you choose?

1. You Have Entrepreneurial Dreams

Don’t overthink it

There are a lot of people that would like to be a founder or a part of a founding team someday; however, they don’t currently feel prepared to set sail on that journey. If you think you might want to start a startup later in life, it seems fairly intuitive that the best place to be now is at a startup.

Examples:

• If you want to be a startup founder down the road: you probably need some experience working with startups

• If you want to be a big tech executive down the road: you probably need some experience working in big tech

If you want to be an entrepreneur (like myself), joining a startup makes a lot of sense. No need to overthink this one.

Access to Entrepreneurial Co-workers

You’ll need to meet your co-founders and early team members somewhere, and the odds are that those working at startups are more likely to be interested in creating a new venture with you.

The classic example of this is the PayPal mafia.

When a startup does well, the ambitious individuals who made it work develop a high degree of trust with one another. When those folks look to create new businesses, who do you think they ask to embark on the next venture with them? When working at a startup, it’s more likely that your entrepreneurial dreams will complement those of your co-workers.

2. You Want Close Proximity with the Leadership Team

Access to the big dawgs

Depending on the size of your startup, working at one of these small companies can give you access to key decision makers who you might never even see at larger organizations, including:

• Founders: Those who started the company (can be technical or non-technical folks)

• Non-Founding Executive Team Members: Those who run teams (i.e. product, sales/revenue, engineering, HR, etc)

• Investors: Both current and prospective investors in the startup

You get to be in the room

Since startups can be such small and non-hierarchical organizations, a lot of the times you will be privy to the strategy and decision making of the firm. Not only does this mean you get to hear what’s going on in the quarterly board meeting, it also means you can get your opinion heard. I remember being so surprised with my ability to ask questions and engage in productive conversation with the CEO at Standard Metrics as just an intern.

3. You Want a Measurable Impact

Comparison to large organizations

The larger the company you work at, the easier it is for your personal work product to be missed, ignored, or miscalculated. At a small startup, it’s very obvious who is doing the work.

“If you want to go faster, it's a problem to have your work tangled together with a large number of other people's. In a large group, your performance is not separately measurable-- and the rest of the group slows you down” – Paul Graham“

Do you want to get paid?

If your work product is hidden to others due to multiple layers within the company, it’s likely that your output is not being fully appreciated. Of course when your output is not fully assessed and recognized, your compensation is probably trailing where it could be.

Startups allow your work to be more easily measurable due to the small size of the organization, which increases your likelihood of getting compensated fairly.

4. You Want Outsized Wealth Creation

Equity rewards good outcomes

Those who are seriously wealthy, have likely owned equity in at least one business. Startups are a super unique way to acquire equity in a company’s early stages. When you hold equity options, good business outcomes can lead to good financial outcomes for employees.

I don’t have too much to say here as many industry veterans have already wrote on this subject. I’d check out Paul Graham’s essay on wealth creation if you haven’t had the chance to read it before.

5. You’ll Still Need to Weigh Other Career Options

Comparing startups to other professions

There are endless career paths that exist and many that have yet to emerge. When I was deciding between options the main considerations were:

1. Investment Banking: specifically technology M&A

2. Consulting: specifically strategy engagement work

3. Service programs: specifically education and international volunteer programs

Everyone has to come to their own conclusions, and in the end I felt that startups were the best choice for me personally. If you have interest in learning more about why I didn’t pursue another path, please reach out and I’m happy to explain in longer form.

TL;DR: Why Join a Startup?

1. You Have Entrepreneurial Dreams

   1. It’s intuitive: If you want to be a startup founder down the road, you probably need some experience working with startups

   2. Entrepreneurial co-workers: Your startup co-workers are more likely to become your co-founders as opposed to your co-workers at a larger company

2. You Want Close Proximity with the Leadership Team

   1. Access to the big dawgs: A smaller team means you get more exposure to founders, execs, investors, and other crucial parties

   2. You get to be in the room: Startups give young employees more freedom to participate in discussions and voice their opinions

3. You Want a Measurable Impact

   1. Comparison to big companies: The hard work you put in can be missed at a bigger organization

   2. Getting paid: If you want to get compensated to the level you believe you deserve, go to a startup where it’s obvious who is doing the work

4. You Want Outsized Wealth Creation

   1. Equity: Owning a part of the business is a fundamental pillar of wealth creation and startups can offer you this

5. You’ll Still Need to Weigh Other Options

   1. I chose working at a startup over investment banking, consulting, and service programs. What will you choose?

Thanks to those who have helped structure my opinions on this topic including co-workers, folks in my network, and of course Paul Graham (and YC).