Chris Winn’s Post

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Product and Engineering | Advisor | Ultrarunner

A little known fact, I once worked for a presidential candidate and his subsequent PAC. I learned a lot that can be applied to product teams. 👇 Heading into the Iowa caucus in 2003, we were tied for last place, barely above 2%. We believed in our potential, but the facts told a different story. On caucus night, we shocked the world. We placed 2nd with nearly 32%, winning only two fewer delegates than the winner (the eventual nominee, John Kerry). With far less money and and a much smaller team, we had hugely outperformed the presumptive winner, Howard Dean. One little known secret of that caucus: we had made deals with other candidates that if either side had failed to reach viability in a given precinct (meaning, not capturing enough voters to garner a single delegate), they would support the other candidate. We won enough of those to stitch together a huge showing. That night, our donation servers crashed under the load of all the money come in. We thought we were it. We thought we were taking the world by storm. I’d never felt anything like it. It was exhilarating. A few weeks later, our campaign collapsed and our candidate dropped out. We simply didn’t have the time to establish a national organization and were crushed by the Super Tuesday primary schedule. We’d saved our one big swing for too late in the cycle. We left ourselves with only one out. To us the loss felt as shocking as our victory had only a month earlier. So what’s the lesson? Sometimes your only way to survival is a short-term gain. If you can only make the small bets, there’s a good chance you’ve already lost and don’t know it yet. What hurts a lot of products isn’t about ideas or resiliency or smarts or features. It’s just poor timing. It’s getting behind instead of jumping ahead. The most important cultural trait of an upstart or insurgent team is urgency. Nothing matters more than urgency. You can control a lot of things when growing a company or team or product — But can’t control time. The best choice - the only viable path - is to move as quickly as possibly. #culture #engineering #leadership

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