Startup Financial Benefits

A Non-Exhaustive List of the Tangible and Intangible Financial Benefits of Working at a Startup

I used to work for a corporate MegaBank for a few years, and it may be anecdotal experience, but it sucked. I was back and mid-office – with a million 50 year old lifer-analyst data monkeys. I was grateful in some degree for the work and grateful for the name on the resume moreso, but I was extremely depressed during this period of time and was pricing flights out to Tibetan Monasteries as a for-real plan B.


I ended up taking a job at Technology Startup and was blown away by the complete change in my mood. I was working double the hours and had gone through a terrible breakup and yet was so happy and fulfilled by actually learning a skill and being valued for once. The word “Culture” is thrown around so much at these companies and it just means generally – shit the company is willing to do to make work slightly less bad. But the perks are seriously insane. I laugh and shake my head at some of the wastes of money at times.


It is important to note that a lot of these benefits are non-existent depending on what level the startup is. A great way to gauge is by how many Series Rounds it has been through. Startups go through numerous rounds of raising capital. I joined when there was about 100+ people and they had finished there C or 3rd round of funding. The company was financially solid and long term plans were being deployed. Anyone on the path to focusing on getting ahead at life needs to consider the below benefits and what effects it can have on your Financial Future!



Obviously. Mainly people think about joining a startup are doing so for equity. It is a difficult balance though – to hit a promising startup at just the right moment for the super rare exit occasion for that equity to ever be accessible to you – and I am a pessimist so that I generally consider as icing on the cake. Foot in mouth though as I was able to get roughly 30,000$ in shares and they float around vesting as hazy somewhat real money. Also you can earn equity in numerous ways, often high performers are awarded shares or RSU’s depending on the situation. This is amusingly an insurance policy for the company as well as high value employees have cascading vesting schedules and lose thousands if they leave. Hard to look a gift horse in the mouth though – free money!



Amazing. Also amazing is legit how many of your coare doing workers do not know there is a max or that they most generally should be maxing it. When I was poorly paid I was putting in to the employee match, but as soon as I was getting commission checks I set it to 10% and ticked it up and down as needed and it started to cruise. I am very relaxed on the whole about the fund allocation within these – as again i just try to remain grateful. Startups are generally heavily pressured into getting these set up as one of the earliest employee benefits as they start to solidify and things are looking grounded. So many people on earth would be better for having a dedicated account like this auto drafting, a majority of Americans even do not have access to this, much the less use it. Auto draft is the savior of my life. It hurts ten times less when you have money taken before it even hits your checking account. Much the same way you don’t feel the sting of paying for health insurance or dental, if you max your 401k you will painlessly be ahead of your coworkers immediately. Tax Free money for future self to compound early on? Yes.


Free Food

The wasteful amount of money spent on feeding employees is impressive. Most startups will provide varying levels of the basics at the different levels of success. I managed to join a startup during the Raisin Bran Cereal and Fage Yogurt funding era. Cereal, PB and J, Yogurt, Almond Mlik, Veggie Straws, Granola Bars, Fruit Juices, Keurig Machines, Bread. I am boring and I view food as fuel purely. Due to my unusual eating habits I have had the same breakfast 6 days a week for the past few years and roughly half of my lunches have been covered. This is an immense savings in both time, mental energy, and of course money. Not having to think about what I am eating and or when – they take care of it and it has the desired effect – I devote my time to working more. I have experimented furthering this with Soylent as well for mixed results.



As benefits get set up health plans will start up and HSA will eventually be an option. Debatable usefulness entirely based on one’s personal health. Pretty much not worth debating with anyone over as health is a personal situation so their is always a valid reason to using or not using this account. I am young, with no dependents, no upcoming medical expenses, that works out and eats healthy. Set these accounts to max and you are putting away another 3,400$ a year in tax advantaged accounts. I assume I will save my Medical receipts in a Google Doc when I have one. I have activated this for the first time and will share my experience as it goes.



Depending on the stage and culture at your company there will often be an Employee Stock Purchase Program. You can choose to divert some of your wages to a semi regular purchase of the company’s stock, generally at a discounted price. The stipulations and conditions vary widely, but I have been using mine as another automatic withdrawal for savings and then auto selling as I can. This is great when paying down debt as you can throw a huge lump at regular periods a time and get a massive psychological boost. It is important to be strategic about holding vs. selling. It is my current view that between my income and my earned stock I am well exposed to my company as it is. Depending on numerous factors this stance will of course vary dramatically.


Free Beer

Happy hours are a standard for forming “Culture.” This allows all members of the company to be approachable. There are no CEOs when everyone has a beer in hand. Techs can talk to Sales and they can all talk to Finance and make fun of Customer Service or Ops together. These are scheduled all the time. Thankfully after the first few – bonding is a great excuse to grab a few for the desk and then excuse yourself to crush some work while getting the buzz on. Productive Beers are right behind Success Beers in awesomeness. Fortune 500 companies are not Mad Men-ing it anymore with a chill mid-day scotch – startups are.


Referral Programs

Startups live and die based on their culture. A huge part of culture is based on hiring people that other people like being around – as you are expected to put in long hours and solve problems together. Referral Bonuses range generally from 2,500$ for a basic admin to 10,000$ for more specialise senior positions. Obviously this is a major shot in the dark but if you have a somewhat extensive Linkedin or Facebook database you can feasibly net a pretty reliable side hustle in this area alone. Importantly, one has to weigh the effect of the applicant on your personal brand at the organization. Going to your alma mater and establishing a connection could often be a good way to get a steady pipeline if you have a reputable background. I know a few long time employees at that  will have earned their entire home down payments based off referrals over a few years.


Unlimited Vacation Days

This is seriously a thing. It likely will not affect your life if you have sane management. But some people will manage to vacation for months at a time while you toil away to hit your goals. I have never used this but I am sure someone can abuse this in conjunction with Maternity leave timing to have an epically paid free year off.


Education Reimbursement

Any HR department has a careful balancing act on hand of following through on promises of career development and keeping that same talent. An easy way they embrace this is the little utilized Federal tax reimbursement. The current max is at $5,250, regardless of income. None of your coworkers are likely smart enough to take advantage of this money, but often employers provide the max knowing how few will take part. Not only will it increase your year end W2, but it can also provide actual education and networking as well. There are numerous programs and education startups around the country geared toward giving you a crash course in something you have some sort of interest in. If you can tangentially relate it to your current role or organization – you get a free resume booster with some light work. I took a course at General Assembly and I can highly recommend it.


Goal Bonuses

Depending on your pay structure, your company may set certain minimum goals and certain stretch goals. Seasonality and various organizational factors will come to play here. However if the reward is big enough often if you are 80% capable you can muscle through and put in the extra hours to reach it. If you can manage to overperform and attain the stretch goal, it is often ludicrously outsized in comparison to the normal goal. The reason is entirely because your boss does not care as the cost would be inconsequential with the gain when they brought the news to the higher ups. Under promise and over deliver in all things.


Free Clothes

Slightly silly but is it just me or is there something super desirable about a free T-Shirt from something you value? When you spend a lot of time invested in something, any symbolism you can get to tie yourself to that in group is going to be a big want. Startups love to garb their employees in swag. Whether it be through contests or giveaways or earning them through dumb HR events – free hoodies are always amazing. Collecting them like candy is part of being a Silicon Valley Engineer.


Free Intramural Sports

If you like team sports you are going to love the shit out of startup world. One of the cornerstones of Culture building is team building activities like lightly competitive intramural sports. HR loves these because it allows them to point at trophies won in non important matches in the interest of bettering the social lives of the nerds it employs. However – if you like a sport – you can most definitely get it either subsidized or funded entirely. Oftentimes there will be a work discount on a particular gym, but a season of basketball could be not only entirely free, but also paid time off from work. Depending on your priorities and comp plan this could be a good thing or bad. Also, requisite free team uniforms for future gym usage – yes thank you.


Free Parties

If you live in a good city the parties will slowly but surely develop into more grandiose affairs as your company becomes more successful. You get free liquor and food and possibly some career development or game time. Make sure you live in the HQ office, nothing regional. Generally a free party is a recipe for disaster for your career, but if you are cognizant of the danger and plan accordingly you can succeed. Staying in control of the amount of alcohol and avoiding the post party strip club crowd are right up there with work affairs. Only do it if she is worth your paycheck. It is possible – just not likely. Spare yourself.


These are obviously not every financial benefit. Just for kicks we excluded the main one, your salary. These are just some of the minor benefits I have seen and taken full advantage of over the course of my years in startup land. I can’t imagine getting this kind of value with this amount of personal freedom at the corporate mega-bank I was at previously. Hopefully some of you will reconsider the fear and distaste that comes from trying a jump to this side. We may not have the big name – but the money spends just the same.