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

As most of you know, I am currently running my fifth tech startup and just launched the beta site last month. 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 an actual paycheck in 11 years
  • I have been managing teams of interns, social media specialists, college students, designers, developers and running daily operations.
  • I used to work 12 to 16 hour days 7 days a week with barely any days off, I admit it’s a bit less now.
  • 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 or CTO.

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 video conference, 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, it never seems to be enough for investors. First they want to see our platform built, then they want to see user adoption, then they want to see some data to support that traction, then they want to see some sort of revenue or monetization strategy. 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.

In my previous startup (and still running it alongside my current one) we accomplished:

  1. iPhone app
  2. Android app
  3. Website platform (now defunct)
  4. Facebook app (now defunct)
  5. 160,000 users – and growing at 100 users per day with no marketing budget
  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. $105,000 in funding
  10. Graduated an accelerator program in August 2014

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!



Jason Sherman

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