Tiger Is A True Entrepreneur, More Grind Than Glory

TIA Ventures
3 min readMar 4, 2021

Did you watch the Tiger Woods documentary?

Tiger (2021): Official Trailer | HBO — YouTube

Do you day-dream about effortlessly shape-shifting into the person or company that you enviously want to be, but are not today? Michael Jordan, Sequoia, Usain Bolt, Adele, SnowFlake, Jay Z, Brian Chesky, a Kardashian, Mark Cuban, DoorDash, Whitney Wolfe, Zuckerberg, Cristiano Ronaldo, Jennifer Hyman, Andreesen, Tesla, Conor McGregor, or insert your unicorn here _______________.

The Tiger documentary does a great job shedding light on the complexity of his life…the monotonously repetitive hard work of swing after swing, the layers of callous building to create an impervious killer mindset, the hardships and tremendous shortcomings of an imperfect character, the life experiences missed out on as a result of a relentless pursuit of excellence, and the web of complexity that ‘being Tiger’ must be. Surely he wanted to be the best. But beyond that, what’s strikingly clear is just how obsessed he was with taking on the day-to-day, heads down, GRIND, in his pursuit of being the best. The struggles and setbacks and breakthroughs, followed by even greater setbacks along his journey. And in almost scripted tragic fashion, the looming existential fear that despite a life of work, he may still never become the unequivocal ‘best’, https://www.golfnews.co.uk/news/the-top-10-greatest-golfers-of-all-time/.

We get wrapped up in illusions of who/what we want to wake up as if we just clicked our heels together…faster, fitter, more famous, the founder of a unicorn startup, rubbing elbows with famous people, etc. I have no issues with aiming high, we all should. But it is a cancerous problem when the illusion interferes with and distracts from the mission-critical day-to-day GRIND of solving critical problems that are right in front of your nose.

Tiger Woods

To bring this to life in the early-stage company-creation arena, we hear a common refrain which goes like this, “if we just do X,Y, and Z we will raise our Series A with a top-tier VC”…and “XYZ” usually takes the form of simple activities (😉) such as growing sales dramatically, increasing conversions, reducing churn, increasing usage of the product/service, improving margins, etc. All totally fine provided your next reaction is going right back into the gauntlet of improving your product, discovering as much as possible about your customers’ needs, finding important facts and key insights, potentially scrapping everything you love but the market hates, listening to hard feedback that may not accord with personal beliefs, and testing things that may totally fail on arrival. ‘XYZ’ are some of the hardest things you will ever do in life. But too often we meet founders who’s entire world revolves around the latter part of the statement, “we will raise our Series A with a top-tier VC”, and the result is they overlook the glaring problems staring them right in the face. Problems that HAVE to be solved first in order to move further down the road on the journey to the promised land. Problems and challenges that are ‘do not pass go’ kinds of issues.

Tiger dreamed big, but executed even more ferociously. He was flawed and his actual journey was complicated, painful, unglamorous at times, humiliating and surely not expected. He wanted to be ‘the best’, but was even more consumed with a constant (and ephemeral) pursuit of perfection, getting better, improving his swing, practicing, strength training, observing his mindset, changing his swing, overcoming debilitating injuries, coping with losses and more. You cannot click your heels together and magically arrive. You may never arrive. You may arrive at a place you never intended. It may still be a pretty damn good place…it may not.

But you have to get your mind off of the fairytale story. Off of the ‘and then we’ll get to our Series A, B,’ etc. You often have to keep your head down more than up, especially in the early innings. Less dream, more drive. This is the un-read script to the unglamorous side of the story behind so many of our idols. What will the untold documentary of your life actually look like?

-Wills Hapworth, TIA Ventures

Twitter: @TIA_Ventures




TIA Ventures

TIA Ventures is a seed-stage venture capital fund that partners with companies building emotional and visceral connections with their consumers.