A Story That Left Me Powerless

For the past 8 years, I’ve had this story of myself.?

A story I’ve repeated so many times, that I forgot it was even a story.?

It’s just become my inevitable truth.?

And the story goes as follows.?

I am not a talented entrepreneur.?

I made one good decision, bringing on my cofounder Austin Rief , but other than that, my entire entrepreneurial journey has been luck.?

My lack of focus, lack of discipline, my excitability, and inability to think at the systems or process-level made me useless while building Morning Brew.?

I gave power to this story, which left me feeling powerless.?

As the world celebrated me for my success as an entrepreneur & Morning Brew’s meteoric rise, I criticized myself for being a liability to my business & my co-founder.?

And as I stepped out of the business in 2021, just 6 months after selling the company & having a life-changing outcome…

A time in which most feel their most successful, most confident, most capable…I felt my most vulnerable.?

Post-acquisition, I would say to myself, “Alex, protect your money at all costs, because this will be your one & only big financial outcome ever. You can only be so lucky. Now you need to play defense.”

And as I write this, I can’t help but feel sadness for younger Alex.?

What a lonely, limited, small way of being.?

A 28-year-old with their entire life ahead of them, the privilege of time & unlimited optionality, yet the only possible future they see is quasi-retirement, financial insecurity, and deep feelings of inadequacy.?

Thankfully, the story gets better.?

One day, I was chatting with my coach, Dave Kashen , and I shared with him the story I just shared with you.

He listened.?

Nodded.?

Felt my pain.?

Took a deep inhale.?

And asked a simple question.?

“Alex, have you ever shared this story with your co-founder?”?

“I have not.”?

“Well, I’m going to ask you to share this story with your co-founder. By when can you do that?”?

“I’ll talk to him before our next meeting.”?

“Great. Let’s see if he agrees with your story.”?

What the fuck did I just agree to? That was my first thought.?

My second thought was, how didn’t I think of doing this on my own.?

Immediately after my coaching session ended, I shot a text to Austin:?

He quickly said yes & we agreed on a time.?

I wanted to make sure I gave him the opportunity to reflect on years of running the business together, so I followed up with the questions that I’d be sharing on the call.?

Four days later came the moment of truth.?

What would Austin say??

Was my story true??

Did he think of me as a valuable partner or deadweight??

I was nervous, but also excited to learn from someone who knew me so well.?

We hopped on the phone & 2.5 hours later I had my answers…

Here’s the punch line: my story, the story I had convinced myself was reality for 8 years straight was in fact…not true.?

Now I’ll caveat by saying that there was truth to parts of my story, but the story was far from the truth in its entirety.?

I learned from Austin that I was invaluable in the early years of the business.?

That without my tenacity to will this company into existence by any means necessary.

Without my unapologetic belief in our vision for what Morning Brew could become.?

Without my ability to build relationships with brands, investors, and employees.?

Without my obsessiveness about our product & our content.

We would have never had the opportunity to build Morning Brew into a 200-person, $75 million a year business.?

I learned that Austin learned many things from me…a fact I never even considered because I always thought about how much I was learning from him.?

He learned what it looked like to be endlessly resourceful and somehow transform an idea into a great product that solved a very real problem.?

Hiring a voice editor from Michigan’s improv troupe to create the conversational, witty tone our content has become known for.?

Turning a rejection from Discover Card into an opportunity to talk 1:1 with their CMO & turning that into a relationship that led to our first 6-figure advertising deal.?

He learned what it meant to be relentless, stopping at nothing to get what we needed to push the business forward.?

Reaching out to advertisers for the 20th time, getting a no, and finding a way to turn that no into a yes.?

Maniacally line-editing the next day's newsletter until 2am to make sure the 5 minutes people spent reading our newsletter was pure joy.?

Littering Michigan’s common areas with thousands of 2x2 fliers only to have employees remove them and only to have me come back and do the same exact thing the next day.?

And he learned what genuine curiosity in people & their stories looks like & how it leads to authentic relationships.

I’m not going to lie…it felt really good to hear that.?

To truly know what someone I care so much about & value so deeply thinks of me…and to know I did in fact drive this business forward…it gave weight to my worth & helped me realize how powerful & oftentimes destructive our stories can be.?

But I did mention that there was some truth to my story, so I’d be remiss not to share that as well.?

In 2019, Morning Brew needed to change.?

We had a dozen employees.?

The business was highly profitable and on an 8-figure run rate.?

And we had ambitions of being more than just a newsletter company.?

Yet cracks were starting to show.?

We didn’t have concrete goals.?

We didn’t have senior leaders.?

And we didn’t have communications that could support a team that could no longer fit around a dinner table.?

To be able to operate & scale the business effectively, we needed to work on the business vs. in the business & to do that we needed an organizational operating system and a CEO that could drive that system forward.?

I wasn’t that guy. A fact that I’m at peace with today, but for years, was the ONLY fact I could focus on.?

And I now understand why I couldn’t be the guy at that time.?

I lacked the urgency to acknowledge that we had entered a new era of the Brew. An era defined by process, planning, and operations, not by scrappiness, salesmanship, and in-the-weeds product obsession.?

And I lacked the skills & the interest to do what was necessary to build that system and lead us gracefully into that new era.

But as I reflect on this experience, I can’t help but feel immensely grateful.?

I feel grateful that I was led to a long overdue conversation with my cofounder that I may have never initiated on my own.?

I feel grateful that I have a co-founder & great friend who could shepherd the next era of Morning Brew, so that I didn’t hamstring its growth at the time.?

And I feel grateful that I no longer believe that shitty story I told myself for nearly a decade.?

I have a new story that I now know to be true.?

That I have the power, the abilities, and the skill to create whatever I want in this world.