5 Reasons You Should Work For A Startup At Least Once in Your Life

By Cailey Ryckman, Finance & Accounting Manager

Hi. I’m Cailey. And I’m bringing back an oldie-but-goody today.

TechCrunch published an awesome article last year about 5 reasons why you should work for a startup at least once in your life. I saw a lot of truth in the article, and wanted to share it with you. If you’re looking at this site, I’m hoping you’re already considering joining a startup.

I have a bit of perspective on big company life vs startup life. I started off my career in Finance at a Fortune 500 company — 126K employees, 60 counties, lots of bureaucracy. After a couple years of that, I decided that big company life wasn’t for me. Luckily, I found Patientco…and the rest has been history.

At Patientco, I manage Finance and Accounting. But a job title really doesn’t give you the full story. To hear that, keep on reading.

So here it is, from the TechCrunch article, with my anecdotes for comparison:


5 Reasons You Should Work For A Startup At Least Once

  1. Start Doing Real Work

No longer are you surrounded by a safety blanket world where you’re a small cog in a large machine. In a startup, everything you do will contribute to the ultimate success or failure of the business…And best of all, you’ll often get to see results first-hand and share in the rewards and glory.

Ever heard of the phrase “paper-pusher?” That describes corporate America to a T. You’re stressed, there are last minute deadlines and fire drills, somebody’s boss’s boss’s boss wants that information NOW…but for what? Nothing, really. Half the stuff that we did in our group had no basis except that “it’s always been done this way and if it ain’t broke, don’t fix it.” At a start-up, there is reason behind everything I do. Why did I build a new financial model? Because our business inputs have changed so much that we needed a new one in order to accurately project financials. Why did I sit through that meeting? Because we’re figuring out how to best solve current business problems. Why did I fill out that form? Because the government told me to.*

*Unfortunately we can’t do away with all forms, because the government loves their paperwork too much. We do try to minimize it and do it online when possible, though. That’s a start, right?


  1. Learning and Responsibility   

I unequivocally say I learned more in my first two months in a startup than I did in the previous five years of my professional career. The reason for this is that everyone in a startup is expected to wear multiple hats. A startup forces you to adopt new skills and responsibilities to make up for the small-sized taking on the huge challenges of building an empire.

Working at a start-up, you learn a lot of stuff…fast. There’s usually no formal training program, no one who’s going to hand-hold you through the process. Starting at my Fortune 500 company, I was handed a binder of instructions for how to do everything. To be successful, just follow the binder, navigate the ever-changing corporate hierarchy, save all of your excel files with print settings already set up, and have a crap ton of 1:1’s with higher-ups. Coming to Patientco, I was handed a stack of projects, and when I got those done successfully, a stack of ten more. I knew nothing about HIPAA, HR, benefits administration, financial modeling, WordPress, or year end tax requirements. But I figured it out. Not perfectly, not all at once, but I got it done. New skills? Check.

You also wear a lot of hats. You have your main job, then your side job, then your side-side job…if something needs to get done, everyone pitches in. When you join a company and it’s only 5 people, guess what? I’m gonna bet that one of those five isn’t going to be an IT manager. Or an office manager. Or an executive assistant. When I joined Patientco as employee number 20 (or something like that), I wasn’t just Cailey Ryckman, Finance Manager. I became Cailey Ryckman, Finance & Accounting Manager who also does all of HR and leads up HIPAA compliance and fixes your computer problem and orders coffee when we’re out of it. You will be too. There’s so much variety! Since you have so many hats, you have a lot of exposure to things you may never get to see at a big company. New responsibilities? Check.


  1. Shape the Culture Around You

You will also find that in startups, you get to shape the culture around you. Entering a larger organization usually means that you’ll be stepping into a predetermined culture, set with existing practices, customs and values. Joining a startup, on the other hand, often means that you can directly contribute to the creation and growth of the business culture, offering ideas and practices that can help shape the working philosophy of the company.

This is one of the most fun things about working at a start-up! There isn’t a corporate values team that tries to shove the same five “pillars of excellence!” down your throat each quarter. Instead, you have a huge influence in what your company’s culture is. Here at Patientco, you can see what each individual employee has contributed to the work lifestyle and atmosphere. Annie loves blasting music and randomly dancing through the halls — she gives everyone a bit of joy and encourages moments of spontaneous fun — like when our co-op Daniel rode his unicycle around the office. Jon brings in a rotating set of games, and you can see people, especially after Free Friday lunch, hunkering down over a heated game of Bananagrams. Tristan is the champion of ping pong and lobbied for a table as soon as we moved to an office that was big enough for it. Kurt and Joshua really instilled the sense of autonomy and ownership that everyone has over their areas. And Bird is the reason we have such a tight family atmosphere here — he treats everyone like family, and in turn, everyone else does the same.

My contribution? The nap room, of course.


  1. An Environment of Innovation

One of the most rewarding things about startups is that you can find yourself working with a team that is highly passionate and enthusiastic. This can spark inspiration on every level, leading to truly innovative ideas and developments that can help the business stand out against competitors in the greater industry.

I have been in many meetings where it’s just a bunch of smart people, a bunch of problems, and a direction: “Let’s figure this out.” That’s when the real magic happens. Everyone is so invested in the success of this company that their enthusiasm and energy is infectious. People don’t hesitate to throw out ideas, build upon others, or scrap something when it’s clear it’s not working. Not only are you constantly surrounded by really intelligent people, but you’re constantly surrounding with very innovative people, people who don’t think “no” is an answer. We’re building something new, something that hasn’t been built before. How can that NOT be exciting?!


  1. Starting Your Own Venture

Joining a startup gives you the opportunity to start learning what it takes to be your own boss. While they take personal and financial sacrifice, startups pay you back in opportunities and knowledge on how to take charge of your own venture.

I recently realized that I had a ton of knowledge about running a business when my little brother called me up one day. (He’s in high school.) “So, Cail, my buddy and I are gonna start our own vape business. What do I have to do to make this thing legit?” As I rattled off everything from pros and cons of different legal entity set-ups to website considerations to marketing ideas, I realized — I actually do know how to run a business. All of those hats that you wear, all of those skills that you acquire, all of those not-so-glamourous tasks that you have to do — those are the moments where you’re learning skills that you can apply to any business venture in the future.


Working at a startup isn’t just ping pong and hoodies and buzzwords like “freemium” and “early adopters.” It’s a lot of work, a lot of responsibility, and a lot of autonomy. It’s late nights and weekend calls. It’s cracking open a beer at the office while working through a problem that requires a bit more creativity to solve. It’s spending way too much time with your coworkers, and counting those coworkers among your best friends. It’s doing something new, something unproven, something a bit risky.

It’s not for everyone. But for some people, it’s the best place to learn, work, and build a career.
I know it is for me.