Why You Should Bootstrap Your First Startup Business as a Resume Booster
Bootstrapping a business fresh out of college is an amazing boost to your future career
Whenever I was looking to hire new employees or assist other managers in their search for new talent, I always gave extra points to potential candidates that had startup experience. I gave them even more points if I came to learn that they had bootstrapped a startup or freelance career.
Why’s that? Well, firstly I went down that road myself a few times and know the value of it. But secondly, it’s because it’s an instant identifier of a person that has faced adversity in business, and is likely willing to do so again.
Candidates can come with all of the accolades in the world, degrees from big-name schools, years of experience in famous companies, lists of certifications through the roof. All of these things are great and all and work well when trying to get into large companies with formal HR departments. I didn’t pay much heed to them myself.
Too many resumes
The thing is, large companies suck at hiring. HR hiring managers and recruiters receive thousands of applications for every position. Each of these applications can take a very long time to go through if attended to properly. That’s why they don’t.
What does one do when they’re being bombarded with too much information to process in a short time? They filter, of course. They have no choice but to.
Some companies try to fight the influx of bad resumes by simply reducing the amount of them. That’s why you see overly complicated application processes on some company websites. It’s to filter out the people that don’t truly want to work there (by making them do a very tedious application process).
It’s why they filter resumes by keywords. Back in the 2000s, there was an awesomely simple trick to get your resume to the top of any automated resume application process — you added a crapload of keywords at the bottom of your resume…in white font. Naked to the human reviewer but very visible to the algorithm searching for those words. The algorithms are too smart not to catch those nowadays, what a shame.
Filtering down to the gold
I’m a big believer that most companies absolutely suck at hiring. It’s because of the same filtering methodologies mentioned above (and many more). At the end of the day, companies who choose not to spend the time considering a candidate as a person, rather than a number, end up with the same typecast employees.
These filtering methods reward longer resumes. Not ones filled with words, mind you. But ones filled with degrees, big names, big companies, years of experience, and keywords. That can get you in the door.
The interviews are then just mostly tests of knowledge, making sure a person has basic hygiene, and to see if they can get along with everyone on the potential team.
I don’t mean to make this sound easy, as there are 50 other candidates going through the same process with you. It ends up being who has the most knowledge, the most hygiene, the most induced laughter from the team.
But there’s also another side to this. Every tech company in the world likes to think they’re the next Apple or Google. The vast majority of them, of course, is not. But that doesn’t stop them from imitating Google’s hiring process.
Filter, filter, filter out all of the candidates! Even those who could’ve been great!
These companies can tend to forget they aren’t Amazon. They don’t have a free barbershop on the first floor, a free Starbucks on the fifth floor, and a full Olympic sized pool in the basement. They don’t have million-dollar salaries or stock options. They don’t have the ability to be so picky. Yet they often are that picky.
Don’t work for them if you can help it.
Put the ‘e’ in ‘funney’
The fun companies in the modern gig economy take the time to look at a candidate. Sometimes that’s because they can afford to. Maybe they aren’t so big yet and don’t attract that many resumes. Maybe they’re fresh out of the gates with a big chunk of VC money to open up shop. Maybe they’re a cool company and want to treat people like people, not as numbers.
Either way, these companies exist, and they can be great fun to work at and help build.
Work for them if you can help it.
What do these companies look for?
Well-rounded candidates at a cheap price. That sounds kind of bad, doesn’t it? Low salary and with experience in a lot of areas? Why would I ever do that?
Because you didn’t graduate top in your class, you’re in your 20’s, and you want to start a new career!
When we’re young, we all like to think we’ll be able to work at the Amazons of the world after graduating, if we wanted to. But the reality is, they hire very few people, and they’re usually the top candidates in any resume field you can think of.
This article isn’t for them. This is for you, the forgotten college graduates that want to make your mark in the business world without having a 4.0 GPA with an Ivey league name attached to it. If you’ve been sitting there applying for jobs for the last 6 months, I have another alternative for you.
Go start your own bootstrapped business.
I’m looking for a job, not a business!
Bear with me, now. I’m suggesting you start a business as a golden nugget on your long term resume. When I was hiring people, there was nothing I loved more in a potential candidate than asking them about their previous startup experience.
It was an instant tell for me. Was this person faking it, were they helping a friend, or were they truly adventurous and delved into the unknown of starting a business?
20 or 30 years ago, this resume strategy might not have worked well. For the simple reason that creating a business wasn’t so easy. Sure, you could start a lemonade stand on the side of the road or sell insurance door to door, but that’s not the kind of resume building businesses I’m referring to.
It’s the gig economy now, and it opened up shitloads of opportunities to be self-employed. People always talk about knowing a friend of a friend that made millions selling this or that online. Or the friend that has a cousin who made an app that got 3 million downloads and bought him a Corvette.
Again, the point of this article isn’t too go make millions from a bootstrapped startup (although if that happens you should still be sure to thank me!). The point is to endeavor down a pathway of self-motivation, time management, financial know-how, and skill learning.
You show me on a resume that you spent one year dedicated to creating a dropshipping business that ended up failing? You get through to the next round automatically.
You tell me how you started a business helping companies do SEO and spent half a year learning everything there is to know on the subject? Bam, passed this round.
What’s that? You built an affiliate network website over the last year that made some money but isn’t enough to pay the bills? I’m sure you now know how to navigate the crazy world of SEO and social media networking, boom, next round for you sir!
Coded an app in the last 6 months that didn’t fly? Show me it and that you’re creative. And kindly proceed to the next round, please.
Lead me to the next round
If you’re still young and look dumb (on a resume), go do a bunch of research and start a bootstrapped company. You may be successful at it. You might learn a crazy amount of things about a crazy amount of topics. You might earn a decent chunk of change to help get you by.
But you will for sure make your resume incredibly more impressive to the right hiring managers in the future.
‘Rant’ over.






