100 Ideas is an awesome platform created by Startgarden to launch early stage businesses. In it they seed 100 different fledgling businesses with $1k, add water and sunshine, wait a tick, and then invest $20k in the ten that show the most traction (or they did until COVID, at which point they lead the way among all local funds in reallocating their money to support entrepreneurs and businesses in need, calling the pivot “The 100 Comeback”).
Side note: this rapid shift in priorities, executed quicker than anyone else in the US so far as I know, was reason number 176 that I adore the people at Startgarden. A group of more conscious investors I have not found.
In any event, 100 Ideas mirrored my experience with Momentum, the platform through which Matt and I started VNN back in 2010, so they asked me to be both a judge and give a talk at their demo day a couple years ago.
Here’s the video of my talk:
Demo days are gut checks of the most fascinating variety. Either your business is among the top # that gets selected, which gives you cash, sure, but more importantly at that stage gives you someone with authority’s stamp of approval, or it’s among the vast majority which are left to walk off into the fog of uncertainty.
VNN, at the culmination of Momentum we went off into the fog. It wasn’t what I would have chosen (I hounded one investor in particular for months afterward, so much would I not have chosen the path on which we ended up), but I think that oppressive aerial water did more to prepare me for life running a startup than any amount of coaching could have done. Running a business is above all an exercise in baking in ambiguity and uncertainty, and coming to know yourself as someone who can thrive therein.
I can still taste that moment in my own journey, so it was cool to experience it again by proxy at 100 Ideas. That faux-binary moment in which you seemingly win or lose a battle for the soul of your business, and if you’re lucky enough to lose, get the opportunity to make the first of many decisions to keep going, despite the evidence.
In the halls of poignant moments in business leadership, this one is up there.