NBA All-Stars & Elite Entrepreneurs Compete Against Strikingly Similar Odds
Tonight, the Indiana Pacers are looking to clinch game 4 at home to take a 3-1 series lead over the Oklahoma City Thunder in the NBA Finals.
Both teams are among the smallest franchises in the league, and both are competing for their first NBA Championships.
OKC’s road to the finals felt inevitable — the team secured a league-best 68-14 record and became one of only six teams in NBA history to win at least 68 games during the regular season.
On the other hand, the Pacers have arguably had the most improbable finals run in NBA history — since qualifying for the playoffs with a 50-32 record in the regular season, they’ve pulled off “the most unlikely set of playoff wins in the play-by-play era”, per analysis by ESPN and Inpredictable.
As much as I’d love to see OKC’s Shai Gilgeous-Alexander fend off a massive finals upset, win a championship, and become the first Canadian player in NBA history to win Finals MVP (after recently becoming the first Canadian player in NBA history to win the Scoring Title, and the second to win MVP), part of me is rooting for the Pacers, too.
Shai and the Pacers are both telling some of the best, ‘against all odds’ underdog stories I’ve ever heard as a basketball fan.
Stories like theirs are a big part of why I joined Tailwind. I love underdog stories, and I get to live in them through my day-to-day of helping ventures raise capital and exit.
There are too many parallels between the NBA and the VC space to cover in one blog post, so I’ll focus on my favourite — the odds of a basketball player finding outsized NBA success are strikingly similar to the odds of an entrepreneur finding outsized VC success. I’ve done some simple analysis around this, which I believe is particularly relevant now, considering the momentous buildup to the NBA finals this past year, as well as the historically difficult venture capital fundraising environment for ventures this past year.

Entrepreneurs’ odds are certainly daunting, but then again, it couldn’t be an underdog story any other way. If you do what everyone else does, you’re bound to get what everyone else gets. There aren’t any shortcuts, hacks, or magic tricks — the players and entrepreneurs who made it ultimately differentiated on their level of diligent preparedness versus their competition.
Consider Shai Gilgeous-Alexander’s diligent preparedness process — according to his former coach, back when Shai was in eighth grade, he consistently came to school early for his own, meticulous 6 a.m. practice sessions in Hamilton, Ontario.
Last summer, Tailwind’s General Counsel witnessed this continued dedication in action while dropping his kids off for a morning basketball camp in Burlington, Ontario. As they walked into the gym for camp, Shai was already wrapping up his early-morning offseason workout.
Evidently, Shai put in more than a decade of work to become an ‘overnight’ success.
If you’re an entrepreneur, Tailwind’s rooting for your underdog story, and we hope you’re rooting for the likes of the Pacers now too, as they compete against the likes of Shai and OKC.
Sources: NBA, ESPN, Inpredictable, Basketball-Reference, Corporate Finance Institute, NCAA, Medium, The Athletic, The Globe and Mail.