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What 6 Months Running a Startup Has Taught Me

We were on the train on the way to Fire Island. My buddy Jordan thought it may be a good idea to
give my roomates a call and let them know the decision I was considering. The call went something like this:

Me: “Hey Bryan – did you see my email?”

Bryan: “Nope not yet”

Me: “Ok…would you mind checking it out?”

Bryan: “Ok….uh huh….mhmm…oh…oooh…woah….(long silence). Alright man…hope it works out”

I had just told Bryan that I was heavily considering quitting my job as a tax accountant with KPMG, moving back home and
devoting my full time towards a project my buddy Judah and I had been working on for almost a year. For
those of you who don’t know, we run a website that specializes in online tutoring over video chat (spanishvirtually and hebrewvirtually)

The feedback I got from people from the decision was definitely mixed, but one thing everyone agreed
on was that it would be a very strong learning experience. That could not have been more spot on.
Now…6 months later after our launch (1/1/2015), here is what i’ve taken away so far:

Human Beings Rely Heavily on Positive Reinforcement…So Much So That It Can Be Compared At Times
To Our Needs for Food and Sleep.

Probably one of the best books I have ever read is titled
Don’t Shoot The Dog: The New Art of Teaching and Training” by Karen Pryor. The book goes over the
fundamental ways in which we make decisions, shaped by positive and negative reinforcement.

When you’re running a startup, you’re constantly searching for positive reinforcement that your idea will work.
You try spreading the word to all of your friends and family, you try posting a ton of helpful content on
social media, you cold call a list of 20 organizations that you think may be interested in your product/service.
When first starting out, especially if it’s your first time running a company like it is for us, receiving
positive reinforcement, even the slightest amount, can take days…weeks…dear god sometime even months!
One of the most challenging things is continuously putting effort into something in which you are receiving
little to no positive reinforcement for. Albert Einstein said it best when he defined insanity as “doing
the same thing over and over again and expecting different results.“ Running a startup puts you on a very
delicate dance between being persistent and not taking no for an answer, and recognizing when an idea just
isn’t going to work out.

A Partner Is Not Just Essential For A Family, but For Every Other Area In Life

One of the biggest things I took away from my experience at KPMG was that you could have the worst job
in the world, with the best people, and it can still be an overall enjoyable experience. Conversely,
you can have the best job in the world, with the worst people, and it will be a living nightmare. I
didn’t fit in too well with my team at KPMG, and it really blowed. It’s one of those areas in life in
which you can have little to no control over and at times can make you feel helpless. Starting a company
means you get to choose who you will bring on your team. Don’t like em? Sayanora! That’s true ofcourse…
unless it is your partner. I’ve come to learn that a partner, in any area in life, should be a mix of
someone whose company(pun intended) you enjoy, and who shares similar goals to you. That holds true for
business partners, spouses, and even close friends. We’re designed as human beings to rely on the
companionship of others. Not having someone in your life to share your time and thoughts with is not
only unpleasant, but dangerous. All the more so when dealing with a company that comes with its own
set of challenges in and of itself.

Your 20’s May Bring You A “Quarter Life Crisis”, But You Have The Opportunity to Reinvent Yourself Easily


Graduating from school is a real exciting accomplishment, but can come with alot of challenges.
You’re thrown into complete freedom for the first time in your life, while dealing with tons of changes.
It’s like you’re used to going every year to this clinic that gives you instructions.
“Let’s see…Aharonoff…Aharonoff…ah here you are. You just finished 4th grade, next comes 5th.”
“You just graduated high school, next comes college.” Then you graduate college, and it’s like your
file mysteriously disappears. “Sorry kid, you’re not on the list. Please step aside, we have people
we need to guide.” There are a lot of perks to life after graduation. You move out of home, you start
making a salary, you go on dates, you manage your own bank account. At the same time, these changes can
be quite a shock.

While you used to have 5 hours a day to see friends, who were all right down the hall from you, now you
have the weekends at best, and your friends are much more scattered. Where you used to not have to think
about money (thanks mom and dad), now you’re setting up budgets, paying off loans and hoping you still
have a penny to save after you pay for rent. One of the best pieces of advice that I got from someone
when asking their opinion on my decision to leave corporate life was that you are able to afford taking
risks much greater at a young age than at a later age. When you’re in your twenties you still have that
fire and energy, you have few to little commitments other than work, and you have the opportunity to meet
tons of people. Want to move across the world for a year? Go for it. Things don’t work out? It’s much
easier rebounding at age 25 then at age 55.

There’s No Substitute In Life For Being A Part Of Something That You Are Extremely Passionate About

I know I know…it sounds really cliche – but it’s true. It’s a real tough balance being involved with
something you love doing, and something that pays you well. Most of the time there is an inverse relationship
(how many people do you know who get paid to play golf?). The way I see it, life is full of uncertainties,
aside from one – death. I hear the taxes argument, but working as a tax accountant you learn that there are
plenty of people who learn how to avoid them. You’re going to die one day. Everyone and everything you know
will disappear. What do you want to show for it? It’s such a tough struggle because on the one hand, you want
to do something meaningful and feel like you really made an impact..like you influenced someone…like you
changed the world for the better. On the other hand, you want to also live a comfortable life – have kids,
buy a house, go on vacations. Right now, the fate of our company is still very unclear – maybe we’ll crash
and burn, maybe we’ll be the next google. Regardless of the outcome, i’ll never forget the feelings of
excitement and adrenaline as we saw results. It’s a feeling that allows you to forgo other necessary
needs in life temporarily, like food and sleep. Being involved on a day to day basis with something you’re
passionate about is one of the biggest blessings out there. I pray we survive, but even if we don’t, I hope
to still devote many hours a week towards working on something I am passionate about, even if I end up
searching for a job in a different field.


These last 6 months have been a real wild rollercoaster, there’s no doubt about it. At time’s I have
felt like my strap was so loose that I was hanging on with 3 fingers, at times I felt like I was standing
up with my hands in the air screaming for more. It’s crazy what 6 months can do. I can only imagine what
the next 6 will bring.

Would love to hear your thoughts or questions – feel free to leave a comment below!

About Josh

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