When to Roll the Dice in a Startup?

Anyone have the answer? Cliff notes to this post: I don’t.

In the first year of building Treatings we’ve been thrifty, to put it lightly. Whether it’s calling the NYU Library our office, calling the tower of terror our beds, or teaching ourselves the required technical skills to build the platform rather than outsourcing, we’ve been pretty cheap to keep alive. I feel as though this has been an asset to this point. But, I’m also wary of our penny-pinching ways. Our DIY approach has come at the cost of speed. It has of course taken us longer to build the site than if we hired full-time engineers or designers.


This is okay, because up until this point we have essentially been running a series of social experiments to determine the best way to connect people offline. If we felt like we had to have all envisioned features on the site, or the sleekest design, in order to get traction, that would be a red flag. I’d even argue that we have benefitted, as first-time entrepreneurs, by not having the ability/capacity to build everything we want all at once. We have to make sure we’re spending our time on high-leverage activities. We make it a point to first find out what we need to build, by talking to users, and then find out how to build it.

Now, after I’ve done the “our weakness is our biggest strength” thing, I will say that I’m aware that it might be difficult to shed this cheap skin and make big bets when the time is right. It’s not that I anticipate an imminent “bet-the-farm” moment, but soon we’ll need to get a little farther out over our skis and spend money to grow our team and scale the product. The difficult question is when…It’s like poker, where you never have perfect information. I’m not much of a poker player, but I do know that in any tournament, the ultimate winner is someone who has faced a few inflection points where they made bold moves that had no guarantee of paying out.

I don’t have a ribbon to put on this post, since I’m trying to figure it out, but I’m sure I’ll have more to say on this topic as we move forward. 

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  1. haydenowilliams posted this