Sunday Email - Lessons learned / History

Read time: ~8.45 minutes

Happy Sunday!

Every Sunday I offer strategies for the week ahead and a thought to fuel your action.

“We are not disturbed by what happens to us, but by our thoughts about what happens to us.” – Epictetus

I can't say I know what the moment of death, or the moments just before, feels like. And I hope it remains unknown to me for a long time. 

However, I imagine it's like a scene from a movie where, as you walk through the gates of heaven, you glance back with extraordinary clarity. Your life unfolds behind you; you see where you erred, understand the decisions you made, and why some weren’t as bad as you thought. 

Death is final, but failure is not.

I failed. 

A wrong bet cost over $7 million, affecting not just me but many who trusted me. It fractured relationships and led to the painful decision of laying off employees who depended on our business for their livelihood.

Yet, failure isn’t the end. 

The moment I turned off the lights of our technology business, I experienced an unexpected peace and clarity. In those moments, I could finally see the entirety of our eight-year journey, allowing me to learn from failure instead of avoiding it.

Right after closing our doors on March 31, 2023, I sought to capture this clarity. The further we move from such moments, the more life's events can skew our interpretations. So, I retreated alone for two days, and 70 pages later, I had documented my thoughts immediately following my life's biggest failure.

Those papers were shelved as life went on, but recently, amidst discussions of potentially writing a book, I revisited them. This reflection offered me clear insights into some critical lessons applicable to all of us.

Replicating others is not a vision

Our journey began in an Atlanta pizza shop, at the height of the robo revolution. We admired Personal Capital and believed we could replicate them to better our mass affluent division. 

We studied every aspect of their business, from their tech stack to their market strategies. But what we couldn’t see was the myriad of lessons, struggles, and iterations beneath their success. We learned this the hard way – our efforts at digital paperwork and account aggregation fell short. They were always steps ahead, while we were learning lessons they had already mastered.

The lesson: Be authentic in your vision. A vision can be inspired by others, but it should be uniquely yours.

Narrow your focus for success

Introducing our workflow automation engine, benjamin, to the industry was challenging. My advisor experience made me believe our tech solution had to be all-encompassing and perfect. We also had taken on capital, so we had to show results. And we were running at a net negative level. So, we either showed results or we wouldn’t be able to raise another round. 

We need lots of at bats with clients and we needed to have the full vision built out… so I thought. 

So we attempted to integrate with numerous technologies (multiple CRMs, reporting systems, calendars and custodians). This approach spread our resources thin. 

In hindsight, focusing on a specific tech stack and perfecting it would have been the wiser route.

The lesson: Find that one thing you are great at. And get better at that. Don’t lose focus on trying to improve all the areas where you have faults, double down on what you do best. And continue doing that until you get bored at doing it so good. When that time comes, keep doing it. 

Get out of the jobs you don’t enjoy, early

Initially, I believed a founder had to be a jack-of-all-trades. It took time to realize that my strengths lay in vision and inspiration, not in management and tactical roles. Yet, I didn’t allow myself to accept that until later in the journey. 

But when I did embrace this by bringing in someone to lead where I lacked, things changed. It led to narrowing our focus, improving execution, and strengthening our business. 

But, regrettably, this realization came too late.

The lesson: Be honest with where you should be sitting. Being a founder or managing partner and not leading the company is ok. Embrace your strengths and step away from roles that don't align with them.

Accept being wrong

In the days following closing the business and even as of a few months ago, I would tell people about the failure of benjamin that “we were early.” Or that the market wasn’t ready for this particular innovation. 

I was fooling myself.

I was avoiding the truth. I didn’t want to admit to myself that I was wrong. Our world teaches us that there is a right or wrong. You either get a green check or a red X in school. And green checks are good and red X’s are bad. 

So we are wired to avoid the red X’s. And given that business is a bit more messy than a multiple choice test, we put some clarifiers on failures. We look externally to the environment. To the situation. 

And thus we let ourselves down lightly. We weren’t wrong, we just were early. We were too innovative for a market that wasn’t ready. 

And all of that is BS. 

The truth is that I was wrong. I made a bet on a solution having an impact on an industry and it didn’t work. I was wrong. I was wrong to bring it to the market at this time. I made wrong decisions in execution that led to lower than needed adoption. 

I got a red X. 

And with that acceptance, I have more clarity. I am able to see the outcome for what it is. I am not running from anything. 

And I am at peace with this. A red X in school is not final or fatal. There is more to go. Another opportunity. It’s not the end of the world. Unfortunately my generation and younger generations grew up in an environment that has led to greater self inflicted pressure on not being “wrong.” 

But reality is, we are all wrong in our lives. If we continue to sugar coat our failures and times of being wrong with external circumstances, then we won’t be able to fully grow. 

The lesson: In life we will be wrong. That is ok. Own your errors, learn from them, and then move on. This acceptance fosters growth and reduces the likelihood of repeating the same mistakes.

This email could become a novel, very easily. But I will stop with these 4 valuable lessons. 

The hope with today’s email is that you can learn from my failure. And that you can accept that failure creates clarity. A clarity that allows for exponential growth. 

When we are “in it” it is hard to see through the muck. But when we get to the other side of it, as difficult as it is, we learn something extremely valuable. Something that we convince ourselves we can learn when “in it”, but in reality can only learn when we get “through it.”

A Thought To Ponder This Week

History, they say, often echoes itself.

While it might not be a carbon copy, the patterns and themes are strikingly similar.

Consider the Roman Empire, dominant for nearly 450 years. It stretched across continents but eventually crumbled due to economic strife, reliance on slavery, military overspending, and external invasions.

Similarly, the British Empire, influential for almost four centuries, shaped global technology, commerce, and culture. However, it too declined post-WWII, grappling with economic hurdles and a shift in attitudes towards imperialism, leading to decolonization.

Predicting history’s repetition is a tricky business. Yet, the catalysts for change often mirror those from the past.

Learning from history isn't about foretelling the future; it's about understanding protective measures. It guides us in safeguarding what we currently hold valuable.

This understanding prompts a crucial question: What steps can we take today to shield ourselves from past challenges? Because, in one form or another, these challenges are likely to arise again.

Heading into the week, let's reflect on this: What lesson from the past do you wish to guard against? What proactive step can you take today to fortify yourself? Let's act on it.

The best is ahead!

-Matt