7 Things The Inspirational Gurus Didn’t Tell You About Entrepreneurship
Thus far, entrepreneurship has been the most rewarding journey I’ve had the opportunity to embark on…but even the most spectacular journeys have shitty stretches.
Today’s marketplace — with the help of Instagram, YouTube and more — is so focused on oversharing that many have portrayed the entrepreneur’s rocky road to success in a way that’s so unrealistic, so incorrect that it’s no wonder why most people give up during the process.
There are kids who haven’t made a penny for their business standing next to rented Lamborghinis with a hundred “hustle life” hashtags in their IG captions. To them and their audience, this is what it means to be an entrepreneur— which has helped create an enormous disparity between expectations and reality.
My own entrepreneurial story is a bit unorthodox. I was working in the startup world in the Bay Area and building up Arctiphi (the social media agency I currently run full-time), when I got fired from my 9–5.
Being fired forced me to have to make a choice: I could get yet another soul-sucking, Kind-Bar-snackin’, beanbag-having, LaCroix-drinking startup job OR try and make a full-time income off of my side hustle, which at the time was only giving me a part-time salary.
I went with the second.
I’ll never ever regret making that decision, but I would be lying if I didn’t say it had its drawbacks. By not waiting until I was making the same amount of money with Arctiphi as I was with my startup job, it made me have to move at breakneck speed so I could pay my bills on time.
During this experience— there are a lot of things I wish someone would’ve told me prior to diving head first into entrepreneurship.
Maybe no one wants to discuss these topics because it forces them to be vulnerable — something many entrepreneurs aren’t good at. Maybe it was the upbringing I had, which didn’t equip me with the financial literacy other kids received from their parents. Or maybe I just didn’t look for the answers close enough.
The world may never know, but what I do know is these are the 7 things I wish someone would’ve told me before starting my business. If you’re reading this and in a similar situation, I hope this helps.
1. Dating will be a hell of a lot tougher than it was before.
While I’m strongly opposed to the glorification of overworking that’s so popular nowadays, the truth is when you’re first launching a company, you’re going to be working a lot…almost nonstop.
Before going full-time into my business, I thought me working 60 hour weeks at my startup job was what “long hours” meant…
When you’re starting out, if your business isn’t your top priority, the road to financial stability will be even more rough and tough than it already is.
Because the reality is this: you’re probably going to have to be the person who takes that call during dinner, skip out on Taco Tuesday, or has to cancel a date last minute because a client isn’t happy.
Surprise surprise — most potential partners aren’t too fond of knowingly being a second or third priority in your life. Who woulda thunk it?
With good reason too. You can’t necessarily blame a partner for feeling neglected when you’re on your laptop working at 11pm on a Wednesday night instead of watching Netflix with them.
My honest advice: Of course, you know your situation better than anybody, but here’s what I’ll say — If you’re at an inflection point on your entrepreneurial journey which is causing you to spend obscene hours on the job, it’s probably best to hold off on dating for now. Casual dating won’t hurt you, but getting involved in a serious relationship might be more taxing than it’s worth. Start dating seriously after you’ve systematized your business enough that it runs itself. Again, just my two cents — but I’m no Dr. Phil.
2. It really is a lonely road.
No matter how great of friends and family you have, most of them probably won’t truly understand the things you’re experiencing and going through as a budding entrepreneur. Sure — you can make friends with other entrepreneurs, but they’ll be just as busy as you are so hanging out won’t be easy.
If you feel lonely as an entrepreneur, just know it’s perfectly normal — if no one else will tell you that, then I will.
3. Taxes will be an even bigger pain in the ass than before.
In the beginning, your income will most likely be unsteady. Because of this, it can be tempting to pocket all of the money your business makes during the high points to ensure you have some extra cash for the down months.
Despite that, it’s crucial to pocket anywhere from 25–30% of the income you make as a self-employed individual into your “IRS savings account”. Granted, this does vary largely from state to state, so be sure you do your homework on your particular situation.
Coming from a blue collar, midwestern/Appalachian family, knowing the in’s and out’s of taxes as a business owner was something completely foreign to me and I know there are people reading this who are similar.
4. Health insurance…pfft, who needs that??
While I applaud startups like Stride Health who are trying to make healthcare more accessible for entrepreneurs and freelancers, the fact is not every budding entrepreneur has an extra $200 per month they can throw around to get semi-shitty health coverage.
5. For most entrepreneurs out there, “bootstrapping” actually translates to “I have wealthy relatives and friends”.
Beware of all of the How-to-Bootstrap-a-Company articles you read out there. Almost all are misleading for one primary reason: they start by saying, “Ask family and friends for initial funding”.
Not sure about everyone else, but my family — both extended and immediate — isn’t exactly in the position to casually throw $10,000 at me to start a business, and I know there are countless others in the same boat .
Because of this, don’t feel ashamed or inferior if you’ve got to take out a bank loan or look around for angel investors. Not every single angel investor out there invests solely in startups. There are plenty who specialize in small businesses, media companies, agencies and more. You just have to do your research.
Of course, the alternative to taking out a loan or raising capital is scraping together money out of your own pocket with side jobs. This is what my brother/co-founder and I had to do when launching Arctiphi. And let me tell you — I’d much rather have an investor on my ass making sure I hit benchmarks than having to drive for Uber until 3am 5 nights per week 😉
6. Managing is a completely different skill than business-building.
Hovering around someone and tiptoeing on egos and navigating through contrasting personality types is something that needs to be taught but isn’t. It’s practically psychology.
7. The office/no office problem.
As a bootstrapped business, in order to make more money you need to have a team of talented individuals helping you turn your dream into reality. Yet, it can be difficult to sway top talent to join your business without a fancy office space, sky-high salaries and never-ending Clif Bars.
Additionally, many universities actually won’t allow remote companies to qualify for a legitimate internship. This is what caused us to bite the bullet and get an office space — even before our monthly revenue was relatively predictable. Even if you have to start out at a coworking space, any office space is better than none.
Some Final Recommendations
1. Once you have just a LITTLE clout, don’t do anything for free.
It’s amazing how many people want free shit. In the beginning, you’ll probably need to do stuff for little to no cost in order to earn your street cred, but the second you have your client testimonials or case studies stop doing stuff for free. You’ll rid yourself of the scummy cheapskates and you’ll be able to finally upgrade from ramen.
2. Connect your company to a larger purpose.
I got this idea from Simon Sinek’s book Start With Why. There are going to be days where you want to throw in the towel. Plain and simple. In order to pull through rough days like these, you have to make your company about more than just making money.
As a result of having a purpose to rally behind, you’ll also position yourself to attract better talent.
3. Rid yourself of ANYONE who brings negativity into your life.
Whether it’s a family member, close friends or a romantic partner, if someone brings in negativity into your life or makes you feel bad about what it is you’re doing, then drop them. Stop talking to them. For good.
I’ve had to do this with a friend I had been extremely close with for over 10 years. All she would ever do is bring negativity into my life and make me feel bad about myself, so I dropped her. I did the same thing with romantic partners, uncles, aunts and cousins.
If someone isn’t there to support you during your season of grinding day after day to achieve your dreams, they don’t deserve to be in your life. It’s just that simple.
4. Self Care Is Crucial
Self care isn’t just some bullshit word us millennials throw around to skip out at a day at work. It really is essential to your health and well-being, especially for entrepreneurs.
I used to think that hustling was the most important part of my life and I could always get back in good condition later. I let myself get out of shape so I would have more time to work on my business. The thing is though, when you’re in great shape you’ll have more endurance to make yourself as efficient as humanly possible.
Ever since I started exercising again and getting back into shape, my writing output has increased, my client retention has increased and I’m happier. I started dressing better and people noticed. It makes you feel good to look good — it’s okay to be a little vain.
Let your business grow a little slower. Better for it to take an extra year or two to build up your business than live 10 years less than you would.
Final Note
I’ll end by saying I’m not trying to steer anyone away from entrepreneurship. I’ll always be an entrepreneur and I wouldn’t have it any other way. What I AM saying though is across the internet today we tend to glamorize entrepreneurship. We speak of it as if it’s a cure-all that will free you from the “jail cell” of the 9–5.
While it certainly is an escape from the lifestyle of an employee, it CERTAINLY isn’t an escape from discipline, from emotional roller-coasters, from holding your tongue, from people pleasing and more. In fact, as an entrepreneur, the responsibility is no longer on your employer, your manager or your colleagues. It’s 100% on you.
I hope this helps! Best of luck on your journey — wishing you the best.
