There have been two times in my career where I observed an entrepreneur start a company and know from day one they were going to execute their exact game plan and crush it. Like a fast pitch getting rocked in the upper decks right after the batter makes contact. No major pivots. Little customer discovery needed. Minor deviations from the original plan. Just execution, swing, and then trot around the bases.
The first time was back in 2010, there was a local CEO named Dave Wright (@JungleDave) on Twitter. He started a business called JungleDisk and within two years, sold it to Rackspace. After a year at Rackspace, he got a bunch of people together at the ATDC, shared he was starting a new company, the only downside was he was going to build it out of Boulder. Regardless, that new company he started was called SolidFire. When he was explaining the problem that day at the ATDC and I just remembered thinking: he’s going to crush this. He knew the exact problem, understood the market timing, and now just needed to go execute it. JungleDave ended up selling the business to NetApp for $870M.
The second time I saw this was a few years ago in the 5th floor community room at the Atlanta Tech Village when Josh Silver shared with me the name of his new company he just started called Rainforest. I’ve followed Josh’s career for a decade as he and Bird Blitch co-founded, scaled, and sold PatientCo. Josh had the same confidence and mannerism as JungleDave did that day at the ATDC. Josh and his team just raised another $20M after raising $11M approximately 8 months ago. Of course, raising rounds doesn’t always indicate future success, but Josh is a proven entrepreneur and wouldn’t be raising unless he knew what Rainforest could be.
There are a few themes here on both fronts: first Josh and Dave are technical founders. Second, they both started and sold something before in a similar market. Third, they did a brief stint in between companies: Dave at Rackspace and Josh with his own consulting firm. Fourth, they started something relatively quickly when they had the opportunity. They were eager to get started because they saw the opportunity and as every great entrepreneur knows, markets move fast and windows of opportunity only last for so long.
When an entrepreneur starts a company, nine times out of ten, there is some evolution or pivot after a year or so in the market. It takes at least a year of customer discovery to understand what is truly possible. However there is the very rare occasion when an entrepreneur has lived and breathed a space for a large portion of their career and knows exactly where the need in the market must be served. Dave knew it from day one and so did Josh. That year or more of customer discovery is replaced with execution of the product and plowing through go to market.
As the dust is starting to hopefully settle coming off the late 2021 high valuations in software, there are several more conversations with employees and entrepreneurs about their next moves. Picking the right company in the right market at the right time is difficult but when done right it can lead to generational benefits. Also, an employee’s day to day is like running on an escalator versus quicksand.
If you’re not going to start a company but want to join a rocket ship with ambitious scale, look for the rare but clear characteristics of proven, technical, and ambitious entrepreneurs eager to start their next big adventure.
Finding entrepreneurs who connect with the fast pitch on the sweet spot of the bat right out of the gate can change the trajectory of careers quickly.