Sunday Email: Struggle / Patagonia

Read time: ~ 5.30 minutes

Happy Sunday!

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

The Struggle is when you wonder why you started the company in the first place.

The Struggle is when people ask you why you don't quit and you don't know the answer.

The Struggle is when your employees think you are lying and you think they may be right.

The Struggle is when food loses its taste.

The Struggle is when you don't believe you should be CEO of your company. The Struggle is when you know that you are in over your head and you know that you cannot be replaced. The Struggle is when everybody thinks you are an idiot, but nobody will fire you. The Struggle is where self-doubt becomes self-hatred.

The Struggle is when you are having a conversation with someone and you can't hear a word that they are saying because all you can hear is The Struggle.

The Struggle is when you want the pain to stop. The Struggle is unhappiness.

The Struggle is when you go on vacation to feel better and you feel worse.

The Struggle is when you are surrounded by people and you are all alone. The Struggle has no mercy.

The Struggle is the land of broken promises and crushed dreams. The Struggle is a cold sweat. The Struggle is where your guts boil so much that you feel like you are going to spit blood.

The Struggle is not failure, but it causes failure. Especially if you are weak. Always if you are weak.

Most people are not strong enough.

Every great entrepreneur from Steve Jobs to Mark Zuckerberg went through The Struggle and struggle they did, so you are not alone. But that does not mean that you will make it. You may not make it. That is why it is The Struggle.

The Struggle is where greatness comes from." 1

Ben Horowitz's vivid depiction of "The Struggle" in The Hard Thing About Hard Things resonates deeply with entrepreneurs—and frankly, with anyone who has ever faced the crushing weight of uncertainty.

Horowitz speaks of moments when you wonder why you even started. He captures that raw inner conflict when people ask, "Why don't you just quit?" and you honestly don't know the answer.

These moments hit home for me when I was building our tech business. Reading Horowitz's words felt like looking in a mirror.

I was in the thick of it, unsure if I could find a way out. Every day felt like a never-ending battle with no clear solution as if the answers were always just out of reach. My mental landscape was a constant cycle of self-doubt and questions without answers. I kept searching for something external to solve it—a magical key, a proven formula. Yet, the hardest realization was that the solution wasn't outside. It was within my mind.

In today's world, we often see conflict or struggle as a problem we must fix. We're conditioned to believe there's a right and wrong way to do things. It's a binary worldview: conflict equals failure, consensus equals success. But that's a dangerous oversimplification.

Real personal or financial growth often stems from conflict, from that friction between differing perspectives.

Greatness is forged in those difficult moments.

As advisors, our job is to help clients navigate conflict. Many families struggle internally between preserving their wealth and taking risks for growth. They feel the tension between maintaining stability and seeking new opportunities.

That inner conflict is often far more powerful than any external market force. Our roles are shifting as the world becomes more connected and our clients grow more informed. It's less about providing the right investment strategy and more about guiding families through their internal struggles—the ones we don't see in the data.

I saw this in a conversation with a team member who was helping me with a project.

On the surface, they were timid, slow to act, and fearful of making a mistake.

To the looking eye, they seemed unsure. But deeper down, their fear was not making a mistake; rather, it was of being homeless and poor.

WOAH!

Facts and realities didn't work here, so I had to use a strategy called " what if" questioning.

It started with the question, "What if you take an action that is not what I desired?" The answer was that we would talk about it. Then I asked, "What if you were to be fired?" and their answer was they would put together their resume and search for a new job. Then I asked, "What if you don't find a desired job within 6 months?" and they answered they would find a part-time job in the meantime. I asked, "What if you don't find a part-time job?"

We did this back-and-forth questioning for about five minutes. That is how long it took to reach the point that they would be homeless on the streets for taking the wrong action today in their role.

At this point, they realized how many things would have to go wrong for their worries to be realized.

The internal conflict to resolve was not motivation, training, or facts and figures but rather helping to gain a changed perception through discussion, not telling.

The challenge here isn't new. In fact, it goes all the way back to our ancestors. Early humans were more attuned to dangers, constantly scanning their environment for threats. A negative outcome meant more than just a setback; it meant survival or death. That instinct still shapes our thinking today.

As advisors, we see it all the time.

Loss aversion is prevalent in both our minds and those of our clients. We know that losses feel twice as painful as gains feel rewarding. When clients fixate on potential losses, it's our job to help them balance the equation. Negativity dominates our thinking, and the negative moments often stick with us the longest.

I once worked with a family who became paralyzed by this fear of loss. No matter how sound the investment strategy, they couldn't shake the feeling that something would go wrong. Over time, it became clear that their fear wasn't about losing money. It was about losing security, about the possibility of having nothing left for their children's future.

By digging deeper, I was able to help them see the real issue at hand, which had little to do with markets or returns and everything to do with their sense of legacy. Thus, spending time talking about changes to the portfolio gave a short-term fix. The long-term fix was having a conversation about what they wanted their legacy to be and how they could best ensure that while they were still alive, which was ultimately beyond money.

The root of these fears often lies in cognitive distortions—irrational patterns of thinking that lead to a warped perception of reality. These appear in times of uncertainty, fear, change, and conflict. Five distortions stand out:

1. Should/Shouldn't Thinking: Expecting the world to operate by a specific set of rules leads to disappointment. In reality, outcomes are rarely black and white.

2. All or Nothing Thinking: This perfectionist mentality leaves no room for nuance. Clients often see investment decisions as either success or failure, with no middle ground.

3. Always Being Right: The need to be right at all costs can cloud judgment. I've seen clients refuse to consider alternative strategies because they believe changing course would signal failure.

4. Overgeneralizing: Drawing broad conclusions from limited data, like believing one market dip signals the end of an entire sector, fuels panic.

5. Mental Filtering: Focusing exclusively on the negatives and ignoring positive developments can lead to paralysis in decision-making.

The future value we provide to families will hinge more on our understanding of these distortions than on our understanding of a specific company's PE ratio. Instead of trying to change their minds, we need to help them understand their thinking patterns. We should help them come to their own realizations rather than being told the realizations they should have.

Using examples from our own lives can bridge that gap. I often share my own experiences with cognitive distortions, like I did many times when building our tech company, thinking there was a right path and a wrong path. Instead, there was our path. Unfortunately, we didn't learn that until it was too late.

Our minds are powerful, but they're not always rational.

As advisors, it's our responsibility to help clients reframe their thinking. Instead of focusing on what could go wrong, we need to help them see what may go right. This subtle shift in language—"could" versus "may"—can make all the difference. It allows clients to acknowledge risk without letting it paralyze them.

I often use metaphors to illustrate this. For instance, if you're at a shooting range with one bullet left to hit the target, you have two options: You can focus on the target and take your shot, or you can fixate on why you might miss. Which mindset is more likely to lead to success?

As we progress in this industry, the greatest differentiator won't be our ability to pick the right investments. It will be our ability to help clients manage their emotions. The one emotion that consistently hinders growth—on a personal, financial, and societal level—is negativity. If we can help clients overcome that, we'll unlock new possibilities.

Conflict isn't something to be avoided. It's where opportunities are born. And it's where, as advisors, we can genuinely add value.

https://fs.blog/ben-horowitz-the-struggle/

A Thought To Ponder This Week

Patagonia was voted the most reputable company in 2021 and 2023.

When you buy Patagonia you feel you are making a positive impact on the environment.

This isn’t just because Patagonia tells us they want to help create a better environment. They act.

Actions from their early days of contributing a percentage of revenues to environmental causes to decisions on how they source materials and ultimately to how the founder set up his transition of shares.

Each action was driven by their purpose… bettering the environment.

Companies are more than just about making money.

Inherently, companies are striving to do good.

But too often words are spoken and fall flat as action is avoided.

Creating a mission statement or a client objective is a bunch of words.

In order to realize the full impact of such words, one most follow up with action.

And action is driven through having a clear purpose and aligning the foundational element of managing money to the desired purpose of making an impact or leaving a legacy.

And ultimately helping families determine, realize and fulfill their unique purpose is so much stickier than any annual return.

So, as we head into the week, find that one client who you’ve helped identify a purpose, then identify an action they can take to work towards fulfilling that purpose.

Share it with them and see what happens.

The best is ahead!

-Matt