Why Work at a Startup?

With the Streak.com team at our 2017 company offsite in San Diego

It’s been a little over one year since I started working at my second Silicon Valley-based startup, Streak.com. I thought now would be a good time to write about what it’s like to work at a startup in case there are people out there interested in potentially joining a startup one day. Like many of you, I was once on the outside looking in at the startup community. Thanks to the many different startup founders, investors, and employees who have written blog posts about their experiences over the years, I was able to learn a lot about the industry before joining. This is my chance to pay it forward by sharing what I’ve learned. I’ll discuss in this article to discuss some thoughts I have about the differences between startups and larger companies, what it’s like working at a startup, and why one might join one.

What Is a Startup?

There’s seemingly almost as many definitions of the term “startup” as there are actual startups, but there are a few things that startups have in common. In my opinion, a startup is a company that is privately held, hasn’t yet had an IPO, and likely hasn’t yet reached product-market fit for their product. Steve Blank says, “A startup is an organization formed to search for a repeatable and scalable business model.”

My own definition of what defines a company as a startup is by using what I call the “Sam Altman Startup Test”. Before Sam took over as President of Y Combinator for Paul Graham, Sam founded a startup in Mountain View called Loopt. When I first moved to Silicon Valley in 2011 and was looking for a job, I interviewed with Loopt. Sam came up to me during my interview to introduce himself and wish me luck during the interview. I didn’t get the job, but that brief chat with Sam left a big impression on me. Here was someone I looked up to and he took time out of his day to shake hands with me and chat for a few minutes. I now use that as a rule of thumb when interviewing for startup jobs: If you can, at a minimum, meet the CEO of the company you’re interviewing with during the interview process, there’s a good chance you’re interviewing with a startup. There’s always exceptions: Maybe the company is too big for the CEO to interview candidates but maybe you can still chat with the CEO on a frequent basis. At the end of the day, it’s up to you to get a feel for if the company still feels like a startup or not. When in doubt, feel free to use the Sam Altman Startup Test.

How To Make a Big Impact

If you have a goal to work in a job where you can make a big impact on the future of the company you work for, then joining a startup might be for you. There’s always reversals to the rule, but generally speaking the smaller the company the better if you want to have a big impact in your workplace. Yes, there’s a huge amount of innovation happening at large companies, but bigger companies have a lot of built-in inertia and it’s harder to pivot the direction of a luxury cruise ship as opposed to a swift and nimble cigar boat. At a small startup, one person can make a much bigger positive impact on the trajectory of the company.

Joining a team with less than ten or twenty employees means you can also potentially position yourself to be in a high-level position if that startup grows to several hundred employees or more. You’d have a much harder time moving up from entry-level to a VP or C-Level role in a company that already has several thousand employees than getting in early in a smaller company and being there as it grows.

The smaller the company, the more likely you will be able to talk on a frequent basis members of the entire company, especially with people working in different areas of the business. Someone who works with customers, like me, will be more likely to socialize or go to lunch with engineers and designers when we all work for a smaller company. The more time you spend with people working in different areas helps with company communication and learning about the different challenges each group faces. Support and sales can give the engineers interesting user feedback and engineering can discuss product roadmaps and future products in the pipeline.

When a customer writes in with a new idea to our support team at Streak, or if I think of a new idea, I can immediately send the feedback to an internal Google Group we have explaining the idea to our entire team. This group also serves as a direct line of communication with our founders who give immediate feedback on ideas or ask us to gather more data or context from the users. You can join a big 20,000 employee software company but the chances you’ll be able to have frequent conversations directly with the CEO are slim to none unless you’re already a high-level executive.

Lean Product Development

As Eric Ries so excellently describes in his game-changing book, The Lean Startup, there’s been a huge movement in software towards the concept of lean product development.

The older method of product development meant spending 12 months building out a new product feature with dozens of different permutations and preparing for dozens of different use cases. The problem is founders would spend so much time in development, by the time they actually talked with customers, what the market wanted was often different than what the founders assumed it was, and thus the founders were often to start over from scratch.

Lean product development is the method of building a very small, limited feature version of a new product in as short as time as possible… then getting that “lean” version into your customers’ hands. By quickly building and releasing the lean version of a new feature or product, a company can get immediate feedback on the new product from users. You can do the best QA testing in the world, but customers will always find broken things that the dev team missed. Customers are also not shy about requesting new features so they’re a crucial part of the early development process of a new product.

Developing lean will either confirm that your assumptions are valid and that it’s worth further developing the product, it’ll prove the opposite that nobody would actually use the product, or even force the product in a different direction due to unforeseen usage and/or feature requests.

One of the coolest things about working in a startup is how fast small companies can crank out updates to existing products and release brand new products to the market. Larger software companies take months just to discuss ideas, going through a maze of middle managers who have to debate and sign-off on every major decision. It isn’t necessarily bad that large companies take more time to make decisions because there’s often much more at stake (thousands of employees and billions of dollars in revenue that can be affected). A small startup can make a product change in a flash and with only a very small number of people that need to be included in discussions on the merits of the change.

One thing to note about joining a small company is the product is likely not going to be anywhere near complete. You’re likely going to notice that the product is only a fraction of it’s potential and where it needs to be. It’s going to be frustrating at times that the product doesn’t have all of the features it needs or things frequently break, but that’s the nature of startups and part of the fun of the journey. Working on the customer side, one spends a lot of time communicating to users that the product is in its very early stages and that the company greatly appreciates all feedback. If ambiguity, uncertainty, and occasional product bugs concern you, go join a larger company that has already “crossed the chasm”.

Startups exist in the “Early Market”. Established companies are further to the right. Diagram via Innolution.com

Focus On Learning and Personal Growth. Take Risks.

One of the best aspects of startups is that they tend to have a lack of formality and have little or no hierarchies so employees can touch many different aspects of the business. Experience in many different areas of the startup’s business will likely pay dividends in the future. If you want to spend all of your workdays doing a very narrow task and not learning much outside of that small window, join a larger company. If you’re comfortable wearing many different hats, dealing with ambiguity, and want to get your hands on as much as the business as possible, a startup is probably what you’re looking for.

When you’re young, you’re in a much better position to take risks. There’s a lot of new college graduates who are only focused on joining whichever company offers them the most money. While I agree with making the most money possible, I strongly disagree with the notion that taking the highest paying job is always the best course of action for one’s career trajectory and to build the most wealth over one’s career.

When you’re just graduating college, you’re likely to not be married and probably don’t have any kids. Unless you’ve been living with your parents, you’ve probably been living a rather spartan college lifestyle in a small apartment or dorm room… possibly with roommates. You probably don’t have the nicest car and your overall spending habits are somewhere between checking under couch cushions for beer money and buying ramen noodles and Sriracha in bulk. This is good! Having very frugal spending habits means you have a low personal burn rate which means you don’t need a lot to live on.

A low personal burn rate is the perfect time to make some bold career and life decisions. You can afford to screw up and make mistakes because you don’t have to worry about feeding any mouths other than your own and you don’t have a mortgage. There’s always couches to crash on at friends’ apartments if shit hits the fan and a couch wouldn’t be a huge step down in your standard of living. One of the bold risks is to turn down higher-paying jobs to work at a small startup. The money will come but you’re not always going to be young, unmarried, without children or a mortgage, and living with a low burn rate. Take advantage of that opportunity while you can.

One of the biggest misconceptions about startups is equity. If you get equity, it’s great, but consider it as likely to give you a great monetary return as a lottery ticket. You don’t join someone else’s startup to get rich, you do it to learn. Keep this in mind when weighing different job offers and discussing salaries.

How To Get Hired

Now that you’ve decided a startup is the right place for your next job, the next steps are to figure out how to get hired. If you’re not an engineer, consider becoming one or at least start learning some of the basics. The smaller the startup you work for, the higher the likelihood technical skills can be brought into non-traditional technical roles (such as sales, marketing, and support) and have a huge impact. An aptitude to learn different skill sets, get out of your comfort zone, and get one’s hands dirty will take you far in your career.

If you’re still a few years away from having good hacking skills, even good enough to apply to a non-technical role, consider looking for a startup that needs helps on the customer side, in sales or support. Support (where I work) is good if you want to get used to working very close with engineers and also if you want to learn how to communicate better with them. Knowing how to articulate customer-speak to programmers, and vice-versa is a very valuable skill in the tech industry. If you want to eventually become a developer, being able to clearly articulate yourself to other engineers will help you tremendously in your career.

Also, and everyone will have a different opinion on this, but consider moving to Silicon Valley to be at ground zero of the startup community. The Bay Area is incredibly expensive so it’s good to have a decent emergency fund saved up. Don’t be afraid to network like crazy and go to meetups and chat with locals. Tell everyone you meet that you’re looking to join a startup. Be as what Paul Graham calls “relentlessly resourceful” and an “animal.” Taking an animalistic, hustler mentality (without being an asshole or being annoying) will leave any good founders impressed. This is what I did to join my first startup, isocket, back in 2011.

Startups have a “get shit done” mentality which means the smaller the company, the more they need to hire for people who can accomplish tasks with very little direction or oversight. Big companies tend to hire people to accomplish one thing and nothing else outside of the job description. Startups are just trying to survive and anything you can do to push the company forward is needed.

Startups will often post job openings on sites Angel List, WeWorkRemotely.com (remote only), and the Hacker News jobs section for Y Combinator-specific companies. Keep in mind that many openings don’t get posted and this is where networking comes in handy. It also might be okay to email employees at different startups and introduce yourself and see if they have any openings not listed on their careers page. Even if they say no, thank them for their time. You may end up making a good connection with them and, considering how fast startups change, they may have an opening in just another few months.

Conclusion and Resources

Now that you’ve finished reading this post, hopefully you know a little more about why someone would join a startup and what it’s like to work for one. Your mileage may vary, of course, so don’t take my word for it: Keep reading and learning as much as possible and decide for yourself.

Some good resources are Hacker News and Paul Graham’s Essays. Also, be sure to check out Paul’s book “Hackers and Painters“, Jessica Livingston’s “Founders At Work“, the aforementioned book “The Lean Startup“, Ben Horowitz’s “The Hard Things About Hard Things“, and Alexis Ohanian’s “Without Their Permission.” Good luck out there! (PS: Stay in touch on Twitter!)

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