What has been the most surprising challenge of doing a start up?


What is the one single challenge that has surprised you the most about doing a start up and what strategies and tactics did you execute to overcome this challenge?

Strategy Tactics

asked Feb 26 '10 at 14:15
Warren E. Hart
2,181 points
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6 Answers


The balance between the time I dedicate to my start up and my family, biggest challenge by any means!

answered Feb 26 '10 at 14:28
4,815 points
  • True, but I am not sure I am not sure that it was all that surprising was it!? – Tall Jeff 14 years ago
  • To me, it was very surprising to find out how hard and difficult it is to balance the time between my family and my start up. If you are married and have kids you know exactly what I mean :) – Ricardo 14 years ago
  • You may think you're prepared for this. You'll probably be surprised anyway. Unless you're emotionally ready to choose between walking away from the company you've nurtured for years and having someone you love walk away from you, you'll be surprised by how hard this balance can be. (It may not get that bad -- probably won't get that bad -- but it can, and does, and it's always that level of hard.) – User1377 14 years ago


I quit my regular job and started my new business without a specific product idea in mind.

I was really surprised how much of your self-worth is tied up in your job - for several weeks I was pretty down, mostly I think as a result of the loss of purpose and identity that one derives from having a regular job.

Two months in, I have a project that I'm focused on and can envisage being successful, but while the black cloud was overhead, it really sapped my energy and ability to focus.

In terms of strategies for dealing with it -

  1. recognising that it's a common but short-term phenomenon
  2. talking about it with people who care
  3. finding something to work on that you think is worthwhile
  4. seeing that you're ability to leverage your own skills and talents will always be limited in a full-time job, but potentially unlimited once you've stepped out on your own.
answered Feb 26 '10 at 23:51
Steve Wilkinson
2,744 points
  • You see a lot of investors citing this self-worth issue as a good reason for having co-founders. They say it takes a pretty strong person to go it alone, not (only) because of workload but because of this emotional component. – Frederick Cook 14 years ago
  • Excellent comment - thanks Frederick! – Warren E. Hart 14 years ago
  • The emotional and stressful side of taking on a near-impossible job alone is definitely tough. Good things to do that help, in addition to the points mentioned by steve, are: Set aside some unviolatable time for your family/loved ones. Set aside some unviolatable time for yourself. Exercise regularly - it's amazing how well this helps to keep your confidence and focus up. – Michael 14 years ago


When I first started my latest venture with a friend over a year ago I was surprised at how many distractions and other project and product ideas I had. I am also embarrassed at how much time I put into some of those smaller ideas.

I suppose the little ones are a lot less intimidating and simpler to consider and execute.

That has to be the most shocking part of the journey so far. Mostly it is a disappointment in myself.

answered Feb 26 '10 at 15:09
Tim J
8,346 points


Besides the family/work balance thatw as managed before, I guess the second biggest challenge was "Doing more with less".

When I graduated and started my first job for a big multinational, I was give a $1M budget for my project... it was huge pack of money, that I could manage the way I wanted. And if I needed more money, I just had to justify it well, and some more cash would come my way.

When I started working for a Startup, I had a very limited budget and was asked to do big things: generate a lot of awareness, get hundreds of leads, build a vast community of users...
What I learned was that you CAN do great things with limited budgets. It taught me to use budget wisely, focusing on high return activities and coming up with creative things to do more with less.

answered Mar 1 '10 at 21:13
825 points


Making sure to keep thinking about the big picture, thinking at a strategic level, thinking about plan a, plan b, plan c. And how we're going to get there. It's unlikely that plan a is going to stay exactly intact. Success is about figuring out what to change and when while continuing to do the day to day tasks that have to get done.

answered Feb 26 '10 at 17:42
4,214 points


In big established Fortune 500 companies you see the limiting factor of getting things done is the people, process and/or organization around you even though there are plenty of resources around to make it seem like it should be easy to get things done. ie: Staffing and funding are not the concern.

Conversely, once you start your own business those process and organization problems are gone, but then immediately it is the lack of resources that become the limiting factor. Of course, going into it the resources you need to do the primary business are very foreseeable, but the surprises lay in all the things that happened "automatically" and sort of behind the scenes in the Fortune 500:

  • Cashing and signing checks
  • Emptying the the trash cans
  • Getting some virus off Sam the sales guy's PC
  • Dealing with your internet connection going down
  • Sending out invoices
  • Selecting health care plan options to make available
  • Anything and everything to deal with the government
  • etc, etc, etc.

In effect, it is all the unplanned activities and the time that those can consume that is the biggest surprise.

answered Mar 2 '10 at 07:56
Tall Jeff
1,406 points

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