3 Challenges Of Creating A Technology Startup

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Startups, especially technology startups, are one of the hardest to build successfully if you are a non-technical founder. Questions arise like, “When should I quit my day job?” “How do I balance working from home while trying to maintain a home-life?” “How do I keep a team that isn’t earning a salary, motivated to keep pushing?”

I’ve been fortunate enough to have been able to make the jump full-time and work on my startup Tip Network, Inc. but have also had my fair share of daily downers and daily uppers. I’d like to premise this post with the fact that I am in no means a serial entrepreneur, but I am confident that what I am going through, many other startup founders are as well. Here are my two cents regarding 3 challenges a tech startup will often face.

1. Quitting Your Day Job

The other day I re-connected with an old friend who had started a mobile apps business and felt like he was at that cross-roads of “I’m not a 9-5 guy, I don’t need to be, but I’m afraid to make the jump.” We got to talking about when is the right time. Looking back on my situation, before I made the jump, I did like many other people would do and I read a lot advice books. Everything I read talked about (1) have a 3, 6, and a 9 month plan, (2) have enough money for you personally and for your company to sustain 3, 6, and 9 months down the road, and (3) leave on good terms.

Fortunately my situation was purely the right place and the right time. I was working for Digitaria | a JWT Company, and I had just received a promotion from sales into accounts. I was in this sweet spot of not having any responsibilities from my past department and the I hadn’t yet picked up any new clients in my new department. I looked at my savings account and at my 401K and had roughly 3-6 months of cash. At this moment, I remembered a quote that I always live by “If not now. When? If not me. Who?” I ran into my CEO and told him that I’m starting a company and I need to put in my two weeks. He blessed me and told me “Digitaria will always be here.”

I made the leap in March 2012 and though things are still up and down at the startup, it was the best decision I ever made.

Now, before I move on, I would also like to point out that I have one of the most supportive families in the world. I packed up my things and was able to move back into my parents house with my two-year old daughter, so food and rent were practically taken care of. I try and reduce spending wherever possible.

2. Balancing Working From Home Versus a Home Life

I’ve tried a couple different working scenarios to experiment with which one works best for me. I’ve tried working from random coffee shops everyday. I’ve tried the local Starbucks. I’ve tried working from my upstairs room, my downstairs room, the kitchen. I’ve tried co-working. In all honesty, a mixture of all the above has been positive on my work flow. However, I will mention that I have been the most productive at Starbucks. There’s nothing like a fresh cup of coffee and free refills all day.

I think choosing different venues to work from has kept me on my toes and lets me explore my surroundings more, but most importantly, it has gotten me out of the house. As you can imagine, living back home with the family and with a two year-old running around can be very distracting. So, I’ve made it a point to get out as much as possible. The downside is that my office setup downstairs is quite comfortable. There’s a window right next to me with a beautiful breeze. My iMac is setup perfectly. I have an awesome headphone setup, amplifier and all.

I don’t think there is one right answer to balancing your home and work life. I think it’s an iterative process. You need to experiment and have self-control when deciding to work from home. When I do work from home, the door is locked and I make sure my daughter knows I am going to work. When I sit her down and tell her, she doesn’t bug me…as much. I also let the family members know that I can’t be disturbed till a specific time.

Again, experiment with your surroundings and have self control. If you can’t work from home cause you get distracted, then get out.

3. Motivating Employees

This is still an area that I am constantly trying to figure out how to do. It takes work. It takes thought and it takes a lot of self-awareness, open-communication, and honesty to be able to motivate and retain friends/employees. We are at the unique stage in a startups life where we are still in product development, we have minimal funding left and are actively seeking new investment. But since we aren’t in beta yet, most investors are reluctant to invest with zero traction. It’s an ever evolving dilemma. During this time is when you will truly see who’s in it to win it. Who is willing to work for equity. Who is willing to put in the late nights, on top of working a full-time job. These are the people that you want on your team.

What I try and do is to thank these people as much as possible and give them an update with where things are at. I try and keep them in the loop so that they see that I am working as hard as I can to find the funding to afford them a full-time salary. I normally do a weekly update on Mondays with discussions regarding the previous weeks activities. I also have done a podcast type approach where I record key updates of what has happened, but keep it only to 8 minutes. This way, people don’t need to read a long e-mail, but can listen to it. I’ve tested it out and I’m gonna keep doing it until I hear that it isn’t working or is annoying.


Starting a startup, no matter what kind, is difficult. It takes the right type of person to be knocked down, left and right, and to get back up and keep pushing. You will have your down moments. You will have your really down moments. But, you need to always keep pushing. If you believe in your idea, you need to do everything you can to make that happen.

I hope I was able to share some insight into some of the challenges a technology startup faces. Please feel free to reach out to me with any questions, or leave a comment below. I am more than happy to talk you out of staying at your 9-5 and making the leap full-time.

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  1. which is the most difficult of the 3?