Reflections on Starting a Company

Being good in business is the most fascinating kind of art. Making money is art and working is art and good business is the best art.
– Andy Warhol

There’s a lot of practical advice out there on how to run a startup.  I want to add a few personal words about some of the intellectual and emotional lessons I learned in building HitPlay.

Some background notes: HitPlay grew organically without investors, so I have little to say about raising money, but a lot to say about earning it.  Also, I started the company over 9 years ago, so these lessons are colored by having seen many business cycles.

1) How to Overcome Fear

One thing I’ve learned is everything that limits us is a form of fear or laziness.

Creating a startup is a lot of work, so if laziness holds you back, you’re not going to get far.

Fear is more complex.  If you have real financial responsibilities (like a family), the fear is valid.  But other fears, like fear of failure and fear of what other people think, is much less useful.


Fear is the mind killer

The way I overcame fear was through a simple thought experiment.  My startup could either succeed or fail.  If it succeeded, fantastic.  But, I realized, even if it failed, I would be happy I tried.  I’d rather be the guy who tried and failed than the one who never tried at all.

Once I made this realization, I had no intellectual reason to not do a startup.

2) Ownership Feels Great

One of the immediate (but not predicted) joys of starting my own company was how great ownership felt.

As an employee, my job was a means to make money.  I did what my boss asked, and I did it competently.  But I didn’t invest much energy into my work.  I just didn’t care that much.

Now that I was working on the product I conceived, for the company I started, I was in a whole new world.  I took pride in every line of code, in every pixel on the screen.  I wasn’t just slinging code.  I was nurturing my baby.

I also took pleasure in the accumulative nature of building.  In other words, I could work all day and make a minor but distinct improvement — and this improvement would be present every day in the future.  I felt like I was rolling a big ball, and every day I was increasing its speed.

3) How to Work Without Direction

When you work for someone else, you’re given direction.  For the first few months of my company, I was still of this mindset.  I kept wanting someone to tell me what to do.

This lack of direction is a double-edged sword.  On one hand, it’s liberating and empowering.  But it’s also overwhelming.


What makes it so overwhelming is you have no constraints on your set of choices.  Do you want to build a certain feature?  Spend your time optimizing page load speed?  Do a Google Ad Word experiment?  Look for someone to hire with expertise in marketing?  Pivot to a new business model?  Paint your company’s name on your body and run naked through the superbowl?  It’s up to you.

4) It’s Lonely without a Co-Founder

I threw myself entirely into my company, and I obsessed about everything.

The problem is no one else really cares if your border radius is 3 or 5 pixels.  Or whether you should pay slightly more for bandwidth in exchange for a lower commit level.


When you run a startup, you’re making tons of decisions that are vital to the business, but meaningless to everyone else not in the trenches with you.

A few months into my startup, one of my friends joined me, and I was much happier because I finally had someone who cared as much as I did.

5) Your Company will Live or Die by Traffic

The single most important and most difficult problem to solve for any consumer oriented web site is how to get traffic.


In my naïveté, I thought all I had to do was build a product people were willing to pay for.  I didn’t ask myself how I would get those people to my site in the first place.

And advertising didn’t work.  Ad rates are set by the highest bidder, so I could only make money to the extent that I out monetized everyone else.  I couldn’t compete in pure monetization, unless the ads were so precisely targeted that the ad volume was negligible.

6) The Secret to your Success is not Public Knowledge

You cannot analytically derive a plan to success.  Because if you could, then so could other people, and the opportunity would be arbitraged away.


To win, you’ll have to stumble into something not publicly known.  For instance, when Google started, no one thought search was going to be big.  Or a company called ThePoint observed that lots of people were using their group action platform to coordinate purchases, so they started Groupon.

You’ll need to increase the surface area of your luck, and keep a close eye on your analytics to see if there’s a pattern you can exploit.

7) Hiring is a Big Deal

In my case, we took little funding and grew organically for years before we made enough to hire people.  The change from just a couple founders to a team of employees was the most challenging transition in the company’s history.

Partly, it was challenging because I had no management experience.  Also, my product was my baby, and I had a hard time letting go.  Nonetheless, before hiring, your effectiveness is determined by what you do.  After hiring, it’s measured by what you get other people to do.  And that changes everything.


I could write a dozen posts going into specifics, but some books that helped include What Got You Here Won’t Get You There, Tribal Leadership, and Good to Great.

8) Your Most Enduring Asset is Your Reputation

Over the years, money comes and goes.  Markets change, businesses follow cycles.

What lasts are the relationships you cultivate, and the integrity with which you operate.

Check your ego at the door.  Don’t focus on how big your slice of the pie is; rather, focus on growing the pie.  Speak clearly, and act transparently.  Over the years, you’ll grow a network of people who like working with you and trust you.

9) If You’re Not Having Fun, You’re Doing Something Wrong

Time spent at your startup should be in service to your life, not vice versa.  You commit to a startup, but you have a deeper commitment to find whatever gives you meaning and satisfaction.

One of my favorite Steve Jobs quotes is

I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.

Note: as Steve said, sometimes you have to do things that aren’t pleasant.  You just deal with it.  But if you’re doing unpleasant things too many days in a row, you should make a change.

In Conclusion

Running a startup is lonely, filled with stress, often not glamorous, and has a high chance of failure.  But it’s betting on yourself.  So if you’re crazy enough to do it, I sincerely wish you the best luck.

20 thoughts on “Reflections on Starting a Company

  1. Man,

    I usually don’t reply stuff, but your article is great to summarize the “Birth of a Startup”. Congrats man! I take my hat off to you (Brazilian expression signalizing admiration for something done greatly).



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  2. Great article Joshua. Always refreshing to read a list like this that isn’t huge in size, but each point is of importance. Points 2 and 8 definitely ring home with us


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