"The Rollercoaster"​ - What Everyone Needs to Know About the Startup Founder Journey



February 16, 2023

If you only gave me one word to describe what it’s like being a startup founder, it would be “Rollercoaster.”

In general, life has its ups and downs.

Some days are good, and some days are bad. Occasionally, you have amazing days. Or really awful ones.

And if we graphed life, it would like something like the graphic below.

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The ups and downs of life

There are ups and downs.

And for the most part, it looks relatively smooth.

Don't get me wrong - there are certainly large dips toward the extremes. We've all been there. No one goes through life without those major low points and major high points. I'm not downplaying life's twists and turns and the highs and lows.

But life is long. And over time, the ups and downs look like a long, strung-out piece of spaghetti with a smooth ebb and flow to the pattern.

But when you decide to insert a startup into your life?

Things change.

The ups and downs go from looking like a strung-out piece of spaghetti to looking like the heart rate of someone riding the Full Throttle rollercoaster at Six Flags.

When you're involved with a startup, time gets compressed - and the extremes of the highs and lows are amplified.

For several reasons, comparing a startup to a rollercoaster ride is precise.

Rollercoasters can be:

  1. Scary
  2. Nauseating
  3. Fear inducing

Rollercoasters can also be:

  1. Fun
  2. Exhilarating
  3. Fear breaking

I experienced all of these emotions during my time with Drivably.

Within days of Drivably being acquired, I started to reflect back on the journey.

While reflecting, I drew this visual on my iPad.

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The Drivably Journey

I want you to look closely at the green section in the middle of the drawing.

Do you see my hand-written note in green near the bottom middle - right above the red "I suck!!!" (yup, I've been there).

The note reads: "All in one day..."

The extreme ups and downs in the middle green section?

That all happened in one day.

One. Day.

That, my friends, is the rollercoaster.

Here’s a timestamped calendar version of what that day looked like for me as a founder:

  • 6:00am: Waking up, remembering we are basically out of money (Ugh!)
  • 9:00am: Receive an email from an investor that says they’re going to invest (YES, more money!)
  • 11:00am: Our biggest customer cancels (...Oh shit...)
  • 1:00pm: We hear back from another big customer who commits to signing up (Whew!)
  • 4:00pm: Receive a follow-up email from the same investor from earlier in the day informing us that they’re not actually going to be investing (Uhhhh?)
  • 5:00pm: Decide what resources to cut to ensure the company doesn’t die (Always the hardest)
  • 5:30pm: Another investor sends a note that says they’ll be investing (Well, this would have been nice to know 30 minutes earlier!)
As an entrepreneur and startup founder, you can reach the lowest of lows and the highest of highs within the same day… MULTIPLE TIMES!

Sometimes, you will even hit those extremes in the same hour.

As a founder, you try your best to smooth these kinds of extreme swings out over time. And sometimes, you can do it (if you get lucky).

But you best get used to it.

Because when you’re in startup land?

When it rains, it pours… and pours… and pours… and pours some more.

Then the sun finally comes out!!!

Just in time for you to fall into a puddle of water while you’re admiring the clear weather.

But you get yourself up (hopefully with the help of some friends, a coach, a mentor, a therapist, etc.)

You dry yourself off.

And you keep moving forward, even if forward takes you into the storm again.

And you get back on the rollercoaster.

Like a rollercoaster, the startup experience can be thrilling, terrifying, and exhilarating all at once.

But the truth is it's not for everyone.

Some people love the thrill of a rollercoaster ride.

They'll run back to get in line again as soon as the ride ends. They embrace the thrill, the terror, the ups and downs, and the upside-downs. They live for it.

But some despise it.

They'll scream at the ride operators to let them off before the cart even begins to move. And they'll forever curse their friends who talked them into getting on the ride in the first place.

They wholly reject the rollercoaster experience.

And that's ok!

Rollercoasters have minimum requirements for riding them. And so do startups.

And not everyone will choose to meet the requirements (more on this subject in the future).

Nor should everyone do so.

But the very first requirement you need to meet before you jump onto the startup founder rollercoaster is to understand the ride you're getting yourself strapped into.

Starting and leading a company isn't bumper cars or the merry-go-round.

Neither is working for one.

Neither is investing in one.

It's a rollercoaster.

All of the emotions you might feel while building, working for, or investing in a startup is captured in this photo from Space Mountain at Disneyland.

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Enjoying Space Mountain with my son, Jett

That’s my son, Jett, sitting next to me.

When comparing his emotion and mine?

Well, a picture is worth a thousand words.

I have personally been on the startup founder rollercoaster.

It was the most challenging yet rewarding years of my entire career.

It’s pure chaos and pure happiness all at the same time.

It’s impossibly difficult to succeed, yet filled with the greatest feelings of optimism and joy that you can imagine.

It’s a ride that’s reserved for the BRAVE, the RISKTAKERS, the BOLD, the FEARLESS, the PIONEERS, and the RARE ones.

Will you choose to ride the rollercoaster?

When you're ready for it, I hope you do.

And when you do - enjoy the ride (and try not to lose your hat along the way)

My weekly challenge to you: Consider where you're currently at on the rollercoaster of life and/or the founder's journey.

Ask yourself: What do I need to do to enjoy the ride?

Now, whatever it is, do that one thing this week to help yourself enjoy the ride more.

Need help figuring it out? Reach out. I'd love to help.

Want to learn more from founders who are on the rollercoaster?

Subscribe to my podcast, "The Rollercoaster"

On the podcast, l interview successful entrepreneurs, CEOs, business leaders, and startup founders about the highs and lows of startup life.

In episode 1, I interview my brother, Derek Hall.

Derek is the CEO and Co-Founder of Miggos.

During the episode, we talk about how to build a world-class network, how therapy and coaching can help founders succeed in business and in life, how we have learned to work together as brothers to accomplish our goals, how hiring a Chief of Staff can be transformative for business executives and founders, what routines, tools, frameworks, and mindsets help Derek to succeed as a CEO, investor, and founder, and more.

Subscribe below!


Apple Podcasts (iTunes)


Google Podcasts (coming soon!)

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