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Why Running a Tech Startup is one of the Most Challenging Jobs Out There

Think like an entrepreneur
Think like an entrepreneur
JasonSherman.org

As most of you know, I am currently running my fourth tech startup and am just three weeks away from finishing up at the StartFast Venture Accelerator in New York. To most people, my job seems glorious, fun, exciting, and full of perks. But the truth is, running my tech startup is the most difficult, challenging, and stressful job I've ever had, and here's why:

  • I haven't had a real paycheck in a couple of years
  • I have been managing a team of developers and marketers
  • I've been working 12 to 16 hour days 7 days a week with barely any days off
  • Every time I feel like I've made a breakthrough, or reached a milestone, my success has been demoted by investors
  • The catch 22 of acquiring funding to scale our platform, but then being told to scale the platform before acquiring funding is completely mind-shattering

So although this sounds pretty bad, I keep doing what I do, because I am passionate about my company, and because I would rather be doing this than working a 9 to 5 corporate job with no silver lining in sight. Let me explain each of my points so that you can see why I actually do what I do.

Paycheck - While I haven't had a real paycheck in years, I've had consulting work to keep me afloat, as well as other sources of income to keep me comfortable and able to work on my company full time. Of course the ultimate goal is to acquire funding and be able to have a salary to continue doing what I love, while earning a real living. This goes for my employees, whom aren't earning a salary either, I am working adamantly to get them one as well.

Managing - Managing multiple employees, whether Database, iOS, Android, or Web programmers, branding or marketing, content, or PR is very difficult because that in itself is a full time job. Keeping track of all the work being done, priority lists, campaign results, code bases, and all the nuances of employee tracking should be done by a project manager of some sort. But in a tech startup, that job falls on me as the CEO.

Schedule - Most people think I work whenever I feel like it, and that I take a lot of time off. When the opposite is actually the truth. I work from 7am until 11pm (or later) most days, including Saturday and Sunday. While I may not be sitting at a computer the entire time, I'm always "on call", whether it's a Skype conversation, replying to an email, answering the phone, having a meeting in person, or crunching down on some computer work. Either way, when you are running a tech startup, there is no such thing as "time off". Sure I take plenty of breaks, go to the gym, cook for myself, go to events, walk my dog, spend time with friends and family. But if something comes up while I'm doing one of those things, it takes priority.

Breakthroughs - No matter how far I've come with my tech startup (we've doubled our userbase in 7 weeks and are on track to triple / quadruple it in the next few weeks), it never seems to be enough for investors. First they wanted to see our platform built (done), then they wanted to see user adoption (done), then they wanted to see some data (got it), then they want to see some sort of revenue or monetization strategy (implementing it in our codebase). We are so excited when we hit certain numbers, add a new feature, gain 10,000 more users, or achieve a really awesome milestone. But I can't say the same for investors. It seems as if they want the world and more, but it's not as easy as 1, 2, 3. Things take time, money, and there is no such thing as a fast turnaround when it comes to software.

Funding - This is by far the most ridiculous and frustrating part of running a tech startup. Investors expect tech startups to get 1,000,000 users, make tons of money in revenue, and get all their development work finished prior to getting an investment. This takes years most of the time and a lot of money to do. It's a chicken and egg situation. We tech startups NEED funding in order to achieve these results. But investors want us to achieve these results BEFORE getting their money. I understand they want more than a PowerPoint or an idea. That's the thing, even with all that we have, it is still like pulling teeth to get investors to write a check for a measly $100k or more.

Here is our current status:

  1. iPhone app
  2. Android app
  3. Website platform
  4. Facebook app
  5. 30,000 users - and growing at 1,000 users per day
  6. In app purchases almost built with a proven revenue strategy (backed by actual user data)
  7. A solid team of developers and marketing experts
  8. An amazing board of directors and advisors
  9. $75,000 in previous funding
  10. Graduating an accelerator program in a few weeks

What more could an investor want? If you know the answer please let me know!

In the meantime, when you meet an entrepreneur, be nice to him or her, and don't tell them they have an easy life, because they will most likely get offended. Instead, tell them how much you admire their choice of lifestyle, and offer to help them, or buy them a cup of coffee, I'm sure they will need it.