Startup Founders: Are You Experiencing Enough Pain?

Written By: Dharmesh Shah September 1, 2006
Auhtor's Note:  The original title for this post was "Startup Pain:  If It Doesn't Kill You, It Just Hurts A Lot".  I changed it because I thought the original was trying to be overly clever.  The message of the article has remained unchanged. 

In the early stages of a startup, I think the founders that are more likely to be successful are somewhat generalists.  They will have a
strength in a specific area (software development, marketing, sales, etc.) but will have some ability to do just about all of it.  Even first time founders of the right make-up will find it an intellectual challenge to delve into areas in which they don’t have any formal training or experience.  This willingness to “figure it out as you go” is a good sign (at least for me). 

Stated differently, I like to see founders that are willing to experience the various types of pain that are common in an early stage startup (particularly a software startup, which is where all of my experience has been).  The value of experiencing the pain, is not just that you learn something (you do), but that you are more likely to fix it – just to make the pain stop.

Experiencing Startup Pain
As the saying goes, “if the pain doesn’t kill you, it only makes you stronger.”  I agree with this.  It does make you stronger.  Here are the various types of pain that I think should be experienced by startup founders in the early days.
  1. Customer Pain:  This is probably the most important pain there is.  You have to try and get as close to how your customer is using your product as possible.  All early software sucks, and the only way to really figure out how badly it sucks (and the magnitude of patience your early customers need to have), you have to actually try it.  I guarantee you that if you used your software daily and put yourself through the pain that one of your customers would feel, you’d fix a lot of the glaring issues.  You simply wouldn’t be able to stand it.  So, the message is, if you feel the customer’s pain, you’re more likely to fix it.  Get in the customer’s head.  Use the product.

  1. Operational Pain:  Over time, you’ll likely have people that are going to help you keep the business machinery running.  This comes from everything like monitoring the servers (if you’re hosting your application), to shipping new releases, enforcing trial periods, figuring out how to collect payments, etc.  In the early days, you’re doing a lot of this stuff yourself.  The lessons here are also critically important.  The more you learn about the pain caused during operations, the more likely you are to find the important ones and change some other element of your startup to help fix it.  For example, if you start getting a lot of pre-sales phone calls or emails for answers to simple questions, you’re more likely to update your website and get some of the common information out there.  The more support phone calls you get, the more likely you’ll be to put in some sort of automated, web-based bug reporting tool that your customers can use.  

  1. Sales Pain:  Sales pain varies based on what type of business you’re in.  If you’re selling a high-end product, chances are you’re meeting with some customers face-to face, doing demos, negotiating terms and finally talking to the “accounting” department of big companies to figure out why the last invoice didn’t get paid.  Once you start living through this process, you’ll come up with ways that you can improve other aspects of the startup to alleviate some of the operational pain.  For example, in my first startup, we sold relatively high-end enterprise software to large financial institutions.  Our best-selling product was a set of web-based applications.  I spent a fair amount of energy adding features to the product that would make it more demoable.  We had a rule that we would never to PowerPoint demos (we wanted to demo the real product).  But the real product was big, complicated, and had a bunch of large dependencies (including a large legacy system that we didn’t develop).  We spent time writing code to help our application work “stand-alone” by adding a simple cache recording mechanism for the legacy app.  This way, we could “script” the demo while we were connected to the legacy app, record all the data, and then be able to do a relatively accurate “real” demo off of our laptops.  Did this take time?  Sure.  Did it add direct value to the actual end product?  Probably not.  But, as both lead software developer and lead sales person, did it help me do demos and close deals.  Absolutely!

  1. Development Pain:  I saved this one for last, because this doesn’t really start to kick in until you bring on more development talent to your team.  In this case, I think it is helpful to feel the pain of a new developer (who we will assume is brilliant and has some experience), get up to speed in your environment.  I’m living through some of this pain this week as we have had a new team member join my current startup.  I cannot tell you how many steps were required simply to get this new developer up and running and productive.  Over time, there are dependencies (third-party and internal) that start building up in the code.  Configurations that you “tweak” just to get things working on your machine (and then forget you did).  Compiler patches, database patches and in some cases, even operating system patches have been done that may be necessary for them to replicate.  Moral of the story?  If you feel the pain of a new developer, you’re more likely to automate much of this, reduce the number of unnecessary dependencies and make it easier for future developers to join and contribute.  If you don’t feel the pain first hand, you won’t even know it’s there.

My general message here is this:  Don’t try to avoid the common types of pain in an early startup.   Don’t try to delegate too early, because you think you need a specialist.  By being involved in software development, sales, finance, operations and other aspects of your business – you will be uniquely positioned to help reduce the pain in one area by investing in another.  It is this kind of behavior that makes for some of the best entrepreneurs.  Sure, some day, you’ll get big and “delegate” a lot of these activities to experts that are a lot better at it than you are.  But, until then, keep your generalist hat on, experience as many different kinds of pain as possible.  It truly will make you stronger.

What are your thoughts?  What pains have you experienced that helped you learn more about your company (and hopefully fix it by tweaking other parts of your startup)?  Would love to read your thoughts in the comments.

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