On Being Positive


At the beginning of last year I jokingly said that one of my resolutions was to try to always be positive with startups I hear about. Fast forward to a year+ later and I am still sticking with this resolution – staying positive in a sea of what can sometimes seem like endless negativity. It has become all too common to quickly dismiss or make fun of the “new thing” and I wanted to stop the trend. I have stuck with it and wanted to share some results, which have been amazing at seeing the optimistic/glass half full side of things.

At first, it was just seeing the bright side – an optimists view. I would take the glass half full side of the post launch conversations.  I would try to be on the opposing side every time I heard one of the following quips:

“Did you see X launch? That’s stupid!”
“Y launched this feature? – it’s never going to work”
“Z raised how much for their dumb idea?”

And of course the infamous:

“I could build that in a weekend”.

It is all too easy to sit on the sidelines while someone else put themselves out there, in the arena, and launch something. Every time I heard someone go off on a company from a press release/feature release or launch I would always course correct back to something positive – it is hard sometimes but after awhile it became almost a game with those around me. The exercise got my brain flexing a muscle that we often forget about – empathy.  Putting yourself in the founders/employees shoes that day can lead to some interesting thinking. Sure there are things that seem silly, but I agree that the next big thing will start out looking like a toy.

So now over a year later, most around me know that I will take the positive side to a startup conversation. This is actually quite hard sometimes but underscores a lot of what I try to instill in entrepreneurs I work with. There are a few times that I may have made a comment or two, but now it’s pointed out to me – it’s great to be known as someone that is positive. The opposite happens as well, having someone come up to me and ask “how can this possibly work?”  These contrarian discussions are a great training mechanism to see things differently.  Debating the opposing side has been a great

There are a few takeaways worth sharing that I try to instill in those I work with;

  • A sound bite of your company can tell your story quickly but your company is not defined by your sound bite. Too often companies get shoehorned into their “its x for y” which doesn’t show much beneath the surface. The problem here is that this is great for VC and pitch meetings, but not always great for consumers or press. The problem is most founders have done way more investor interviews so the narrative from those slides bleeds out into the verbiage in a press interview. A press interview is not a VC pitch which is not a candidate selling conversation which is not a family explanation which is not a vision blog post – each of these things are different.
  • The mission, vision and values of your company may get lost in a press interview and the outcome or written version is a great way to see if it’s clear to others. I bring this up often because most companies do not have or set a mission, vision, and vales definition early enough.
  • If the definition of your company involves another company – you are doing it wrong. As mentioned above if every time you tel your story you are mentioning another well known startup you make the cognitive load too high for the other party. Here are a few examples:
    • “Airbnb for cats” – you have to know what airbnb is, then think about why it should be applied to cats.
    • “X but for mobile” this one happens a lot. Again, you have to know what X is and they already have this solve for mobile. So what are you building? There is clearly something going on (being positive!) but the story is not coming out

Finally, I encourage anyone else who wants to be positive around startups to join me. It’s too easy to pile on when a company is having a bad day, so take the high road and see what is like to throw some support to those who need it.

Also published on Medium

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