• morgantate
  • Posts
  • when does the dog stop chasing the car?

when does the dog stop chasing the car?

Chasing cars we can’t catch, re-inventing corporate hackathons, and 3 workouts to try this weekend.

Author

Morgan Tate
August 01, 2025

The best entrepreneurs bet on themselves. Often because no one else will.

This becomes a brutal trap. After all, why would we try if we didn't believe we'd succeed?

This slippery slope can lead to devastation. You know what I'm talking about if you've ever met the 40-something entrepreneur on their 4th failed startup who still fully believes, "This one is the winner!"

The problem is confirmation bias. Aspiring entrepreneurs fill their minds with stories about Thomas Edison's 1,000+ attempts at making the light bulb before succeeding. "I have not failed. I've just found 10,000 ways that won't work," he famously said.

Yet for every Edison, thousands of names never make the history books.

Some entrepreneurs are like delusional dogs—they chase every passing car with boundless energy and determination to "catch it."

I call these entrepreneurs "Gil."

Gil Gunderson, if you're not familiar, is a character from The Simpsons. Gil is an intentionally forgettable and tragic figure whose running joke involves brief appearances throughout the series. During these moments, he typically has a new job or promising opportunity and says to himself, "Things are finally looking up for Ol' Gil!" only to have that opportunity snatched away seconds later.

A lot of entrepreneurs probably resonate with Ol' Gil. I know I do.

As previously cited, my last startup, figuratively and literally punched me in the face.

Over the past decade of entrepreneurship, I've frequently found myself feeling like that proverbial dog chasing the car.

I chase the big sale, only for it to fall through for reasons beyond my control. I had the opportunity to sell one of my companies, only for the lead deal maker to quit his job—killing the deal in the final hour.

It would be easy to focus on these moments and, in the words of Gil, put myself in a "pit of despair"—but for what?

To live a meaningful life, we require purpose. No meaningful mission has been accomplished without failure. Without failure, we never develop willpower.

So instead of drowning in self-pity, I now laugh at these "Ol' Gil" moments and struggles. Each has made me a more resilient entrepreneur. Big problems recalibrate your perspective on smaller problems because "you've been through worse."

There comes a moment when you realize that the "chase" is the unstoppable inertia within entrepreneurs - this drive will never disappear. If anything, the more experienced you get, the faster the car starts driving.

Peace is found in learning to love the chase. After all, you're a dog, what are you going to do if caught the car anyways?

idea of the week 💡

Credit: Idea Browser

  • problem: Most corporate hackathons fail before they begin. Companies waste weeks on logistics, struggle with team formation, and end up with underwhelming results that never see implementation.

  • idea: Hackathon-in-a-Box - an enterprise platform that handles everything from registration to demo day. The platform automates participant matching based on skills, manages project submissions, coordinates judging, and provides templates for post-event implementation.

  • how it makes money: $5K-$15K per event depending on company size and customization needs. Target mid-market tech companies ($50M-$1B) looking to innovate without massive R&D budgets. For every 50 companies running quarterly events, that's $1M+ in annual revenue.

  • why it might succeed: Perfect timing with AI market projected to hit $1.8 trillion by 2030. The platform's participant matching engine uses advanced algorithms to form balanced teams, ensuring senior engineers don't cluster together and newcomers get meaningful roles.

  • why it might fail: Complex build with AI integrations (6-month MVP timeline). Enterprise sales cycles are notoriously long, and customization requests could drain development resources. Companies might try to build similar solutions in-house.

workout of the week

at-home workout:

Complete 3 rounds of this time-reclaiming routine:

  • 12 intention-focused push-ups (focus on form, not speed)

  • 15 bodyweight squats with 2-second pause at bottom

  • 45-second plank with alternating shoulder taps

  • 10 single-leg glute bridges each side

Rest 60 seconds between rounds, use this time to breathe deeply

gym workout:

  • 4x6 compound lift of your choice (bench, squat, or deadlift)

  • 3x8 pull-ups or lat pulldowns

  • 3x12 dumbbell lunges (alternating)

  • Finisher: 4-minute Tabata (20 seconds work/10 seconds rest) of kettlebell swings

outdoor workout:

Try this high-intensity circuit:

  • 10-minute progressive run (increase pace every minute)

  • 40 walking lunges with jump transition between legs

  • 25 decline push-ups with feet elevated on park bench

  • 45-second single-leg pistol squats (each side)

  • 30 burpees with lateral jump over obstacle

  • Complete 3-4 rounds with 90 seconds of recovery.

tweet of the week

my plugs