Now, I know we want the people we take advice from to be perfect or at least practice what they preach. I know you want to hear I’m an entrepreneur to the bone and at my core being I’m all about hustle, grit, grind, being self-made, and not working for the man or any other entrepreneurial mantras that may spring to mind.
After starting several companies and making some successful exits with nothing in the current pipeline you may think one of two things: either I wanted to take a well-earned break, or I have a new plan that I’m ready to sink my teeth into.
Well, oddly, I do love to work, actually I don’t know what to do with myself otherwise. But, I was feeling too tired to jump right back into the entrepreneurial world. My last business sale still had my mind reeling. I had dealt with fires, robberies, and lawsuits in the past years before I sold, and I think it had me in a bit of shell shock. Not quite ready to jump back into the shark tank, I thought a job working for a company I admired might be a great change. No more 100-hour weeks, a steady guilt-free paycheck – and ever the curious learner, maybe a chance to improve. If I was lucky, this could be a chance to work under a great CEO and learn some great new leadership skills.
Is it harder to get hired after self-employment? I found out the hard way.
Feeling confident about my background, I started on the journey. After all, by now I had built a company from a 4k startup to a nationally recognized one. I Invented and launched a natural sleep aid with surprising success in Europe. I co-founded a mattress store which was on its 3rd successful location before my exit. On top of this, I had been a top adviser for many brands that went from idea to success as I walked other entrepreneurs into their dream businesses through my consulting. I had an MBA and a biochemistry degree. I even had a fancy resume I paid $1000 to have written for me.
I mean, I was a shoo-in for anything I wanted right?
Dealing with rejection
So, after no good news from the first 10 companies, I didn’t lose heart. After 50, I started to check if my email was right. For the first 100, I thought maybe it just takes time but after 200 I started to wonder about all these companies who claim to be seeking someone with an entrepreneur mindset?
Between words like entrepreneurial, driven, and all the other shark tank buzzwords they found to use that day, it almost felt like “entrepreneur” was used as a way to weed out all of us self-working tigers. “They jump at that word and you cut them, OK Al? Yep, don’t need no entrepreneurs on my watch!” I thought to myself if this was true, it was time to change my approach.
Changing strategies
This is when it got fun… I decided to make this about me now. I had nothing to lose and everything to gain so I devised a creative plan. I decided that I would write the most fun and interesting cover letters of all time. Then, I would send them out to companies that I thought would value creative, entrepreneurial applicants.
Company 1:
Oh, you have an ad out for a global brand manager for a company that makes action figures? Let me tell you how I myself am an action figure.
I’ve trained in Muay Thai in Thailand and traveled the globe as an MMA coach. I did research in an actual spider lab and built Unimog’s for the USA channel’s apocalypse shows. I am an action figure. On top of this, I built a national brand with only organic work and no marketing expenses. But, their lack of response means they must have found a better candidate. Perhaps I should have added the Kung Fu grip to my resume.
Company 2:
So your dating app needs a marketing manager? Well, I’m your man! Here is my resume in the form of a dating profile. My last line was a zinger: “Usually, I like to be the one to open the door but this time I’m hoping you do.” No first date, no message back, I guess they don’t like transient appearing men…
Company 3:
Ok, this is it. Branding for tv streaming service. I thought to myself, “what if they check what I’m watching?” Well, that would be funny since it’s all Viking shows and documentaries. Perhaps the cover letter should showcase my skills ala Viking, but… perhaps with better behavior.
I mentioned all the good things I had in common with Vikings. Along with mentioning traits like being hard-working, trendsetting, and having a goal and task-oriented mindset. I also mentioned how this Viking has people skills and is a team player. But alas, no Wunderbar. No great expedition to the tv streaming job world. Maybe they found something else in my watch history that was more concerning than Viking shows?
Are entrepreneurs unhireable?
There are a lot of rumors and opinions about what business is. Still, very few people like to talk about the downsides. Many of the fellow entrepreneurs I know stay in businesses they no longer want to be in because of the very fears I mentioned above. Many employers have their own ideas about hiring self-starters, too. They often say things like, “entrepreneurs are unmanageable, and they will ditch you for their next endeavors as soon as they get a chance”. So, are entrepreneurs unhirable?
If you have success in business, it’s not a far stretch to say you are unhireable. It’s kind of like a prize you get for making it past the first couple of years of self-employment. This is not the worst thing; it checked a box off for me. Can’t get a job after self-employment? Congrats, you are a real entrepreneur. Now, what are you waiting for? Go get on your next startup!
