Reflecting On My First Month At A Startup

When I graduated from college, I was lucky to have a job ready to go. I took a short 3-week vacation in January 2014, and then I jumped right back into hard work. At least I was making money and no longer working 80-100 hour weeks like I did for my college degrees! I built many strong friendships, and even convinced several coworkers to max out their 401(k)s, Roth IRAs, and HSAs. Like any job, it wasn’t destined to last forever. After 3.5 years of working for a large defense contractor, I needed a change so I joined a small 7-person startup, and it has been very different so far.

Everyone Must Leave Their Job At Some Point

One of the best reasons to change jobs is because you are undervalued and undercompensated. I primarily left because I was undercompensated. I helped bring in about $5 million to my company over the 3+ years I was there. In addition, I was 1 of 3 people in our entire business unit that had a specific, in-demand technical skill. Given all of that, my company refused to pay me what I was worth. Even though I received several glowing performance evaluations, my promotion took 1 year longer than usual. When my promotion finally came, it was less than I negotiated for, and less than what my company verbally agreed to pay me.

Unfortunately, this will happen to everyone unless you run your own business. If you work for somebody else, especially at a large company, you are 2 numbers: your generated revenue, and burdened cost. At a large company (think 50,000+), you’re a small fish in an ocean regardless of performance. It is no wonder that employee retention is difficult. I’ve even had several managers say they don’t know how to manage Millennials and it shows when 20% of us quit every year at my old job.

Adjusting To Startup Life

Startups are very different than 50,000+ mega corporations. Right now, I am 1 of 7. Our whole office is smaller than my apartment. We only have 4 desks for 7 people so we often have to share. I no longer have access to a full kitchen, just a microwave and a water cooler (that our VP unplugs because he likes warm water). The biggest thing for me is impact. I have the power to have a massive impact on my new company. With that in mind, I try to do as much work as I can. My primary job is Pre-Sales Systems Engineering. Basically I’m the engineer on sales calls that runs presentations for tech leads, and helps answer questions with the overall goal of making a sale. I am also a technical consultant with about 15%-25% travel.

Before I even started at my new company, I wanted to walk in “guns blazing.” So I started looking at their social media and website. Man, they sucked. They didn’t follow security best practices and their website was 100% vulnerable to hackers. I immediately fixed this on day 1. By day 2, I volunteered to run all of their social media (Twitter). By day 3, I was their primary copy editor for blog content. By the second week, I was creating marketing reports on the success of our campaigns.

Working for a startup has given me the opportunity to wear many different “hats.” I’m in sales, technical engineering, and marketing. Learning all of these skills will greatly benefit my future. At some point, I will leave this company, it is just a fact of life. Having a diverse set of skills with lots of responsibility will greatly impact my next job.

Financial Impact Of A Startup

One great thing about changing jobs is that I increased my salary by 25%. I was able to do this because I worked very hard at my previous job and built up very in-demand skills. The thing is, my new income is almost identical to my previous income! At my old job, I made $4,000 per month post-tax. I also contributed $2,000 to my 401(k) between my contributions and my employer’s. Now, I make about $6,500 after taxes. A tremendous amount of money, but not much more than I was making before. This sounds like a lot of money and it definitely is. But compare that to D.C. rental prices and it isn’t quite as much. Compare that to property prices on Long Island, NY (where I am moving in August) and I’m not doing as well as I thought. I’ll need to save $200,000 for a home down payment, and hopefully my property taxes aren’t more than $15,000 per year if I’m lucky.

One negative is that I now spend about $360 a month to work at my new job. You all know my opinion on fancy lunches. If you cut out your fancy lunches, you’ll have $1 million by the time you retire at 65. Well, I now must spend $10-16 on fancy lunches every day. Combine that with $8 parking every day (80 cents per hour that my employer does not reimburse) and I spend a massive amount of money just working. I do save some money on my commute. The drive decreased from 22 miles down to 4. Unfortunately, I averaged 32 MPG during my old commute. I’m lucky if I hit 15 MPG now. Plus, it takes the same exact amount of time to get there.

Health Benefits Of A Startup

One major benefit is that my health insurance is f****** incredible. Yes, I pay $300 a month and my employer pays $500 a month. But my deductible is $0 and my maximum out of pocket is $1500. My co-insurance is 20%. This got me to actually go to the doctor and hopefully solve my 24/7 pain in my fingers and arms that I’ve had for the past 6 years. Hopefully typing won’t hurt as much now. I’m also a lot happier here. I gladly work 50+ hour weeks. At my old job, it was torture to do 40. I’m much less stressed out in general, even though the individual components of my new job (sales) are much more stressful than going into a room with no windows and smelly engineers for 8 hours a day.

Overall, I’m happier which is the most important part. Hopefully this job accelerates my career trajectory. Worst case, I’ll be 100% WFH in September and I’ll finally be reunited with my fiancée which will make me extremely happy.

Good Hunting,

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18 Responses

  1. Sylvia says:

    This was fun to read. I can tell how much happier you are at your job just by the tone in this post. I really like the idea of working at a start-up, but I don’t really know how I would go about it.

    >my property taxes aren’t more than $15,000 per year if I’m lucky.

    That was a punch in the gut to read. Come move to the Midwest! My property taxes are $1,200 per year.

    No, but seriously, it sounds like you’re on the right track!

    • David says:

      Thank you for reading! I’m much happier so it was definitely worth switching companies. If you are interested in looking for startups, check out Even if you aren’t a technical person, it lists startups in your area and you can manually look through the companies.

      My dad’s property taxes are $6,000 per year on a $200,000 home–with a special senior discount. My mom pays $8,000 on a $350,000-$400,000 home. I’ll probably end up spending $600,000 minimum for a modest single family home in a good school district, but that’s the price I pay to live near family.

  2. Barnaby says:

    Can you brown bag lunches? Seems like that would really help.
    There’s nothing like working for a start up in terms of having the ‘move the needle’ feeling in your professional life. Congrats on the move to a better job, sounds like the last company was ethically-challenged anyway.

    • David says:

      Thank you! I can technically brown bag my lunch, but it’d basically be saying “F you” to everyone in my company. Around noon they all get up and go out to lunch. It is a small, tight-knit office so I can’t really skip. I’m really liking startup life!

      • Lily@TheFrugalGene says:

        Woah, $10-$16 for lunch? I wonder if anyone else on the team realizes the $ pinch of a fancy lunch but they don’t want to rock the boat and come off ‘cheap’ by brown bagging.

        • David says:

          Yeah it adds up very quickly -_-. My CEO and VP are probably worth 8 figures each so I don’t think they particularly care. I used to just bring peanut butter sandwiches and spend maybe $6 a week on lunch. It was more boring a less healthy ($10-12 buys a fancy salad near me), but 10x cheaper

  3. Congrats again on the new job! Sounds like you are settling in nicely. The cost of living in NY is insane and its sad that even after that amazing jump in salary it feels like you are still making about the same after housing and other expenses. My husband and I live 45 minutes north of NYC and it is the same situation. We are on the low end of the tax spectrum and pay property taxes around $10K, but there are some areas where people will pay $35 to 50k in property taxes alone! Great point on the lunches too. My husband now works in NYC and there is at least a $5 to $10 difference per lunch based compared to CT where his last client was located.

    • David says:

      Thank you! I’m really liking it. The cost of living in NY is insane. Property taxes are very high, state taxes are very high, and local taxes are also very high. I’m looking at areas on Long Island (think Syosset, Jericho, Port Washington, etc) and they’re all stupidly expensive. But it is the price that you pay to live in a suburb 45 mins away from Manhattan.

  4. Dude. You’ve got me hyped up and ready to start looking for a new job. I’ve been on the fence about it for two years…

    • David says:

      The present is always a good time to go job hunting! Why have you been on the fence?

      • My job is just soooooo easy. I only make ten bucks an hour, but I have roughly 6 hours of down time in an 8 hour shift. I write for my blog, play video games, and watch netflix.

        Who else is going to pay me to do these things?

        • David says:

          My fiancee has a similar job. Unfortunately, the boss is shitty and her coworkers are racist. She can’t bring her laptop and work on her side hustle. I’m really contemplating telling her that she can just quit if she wants to, I’ll put her on my healthcare plan, and she can devote 100% of her time towards her side business. She made more off her side hustle last month than she did during her regular job. This isn’t sustainable… yet. But I think by the end of the year, she could completely replace her day job’s income.

          There is no harm in looking at other jobs. The grass is always greener, and you’ll probably miss an extra 6 hours of free time if you switch, but odds are it’ll probably be worth it, and more money helps too

          • Ouch. I don’t deal with co-workers or bosses. Shift change takes two minutes and when someone needs to communicate with me, it’s by written note or text message. Third shift does have its advantages…

            You’re fiancee seems to be in an infinitely worse situation as far as day job and an infinitely better one as far as side-gig. Her making the switch could be a great move for both the “her” and the “us”.

            The way I look at it, I make $40 an hour. I just have to sit around for six more with the freedom to do as I please. When I look at it that way, it’s hard to justify leaving for a job that brings in equal or even better pay.

          • David says:

            It is definitely hard to leave a job if you don’t do much work and get to enjoy your down time. Getting a new gig where you make more overall but fewer per hour and have less free time is hard, but potentially a good investment.

            I’m hoping that her situation improves, she switches jobs, or just drops it and focuses on her company full-time, but we’ll see how that goes. I can cover her on my healthcare plan for only an extra $200 a month

  5. Hi David. Nice to read more details about your new work arrangement. It sounds like it suits you very much and you are kicking ass! You’ve also been able to learn a ton of new stuff since you work with so few people and I’m sure all of you have to wear multiple hats each day.

    • David says:

      Thanks! Learning stuff is great! I think my employer might want me to do work with… similar customers at my last job, which is going to be a problem

  6. Jane says:

    Every time you mention how much you spend on lunch at work, I’m flabbergasted. That said, you’re making a lot more, you have awesome benefits, and a (remote) exit plan! I 100% agree with you on the importance of leaving for new opportunities, especially when we’re talking about a 25% increase in pay.
    Between a new job, running this blog, and starting a new site, you’ve been keeping yourself so busy, and so so productive! You’re killing it, David. :]

    • David says:

      Thanks Jane! Parking + lunches = $400 per month which I really don’t like, but I’ve got a little more than a month left!

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