A few weeks ago I sat down with Coffee Futures Fund for a long conversation about how Cat & Cloud was actually built — not the highlight reel version.
We talked about the Disneyland trip that shaped how I think about hospitality. About the cup size decision that almost didn't happen and ended up growing the business by 40%. About what it took to make joy repeatable instead of fragile.
They wrote it up as Issue #1 of a new series called Letters to Young Coffee Owners. It's the most honest account of how I think about this work that I've read.
Check it in the link above
There’s this idea floating around that leadership must be fun. That if you’re doing it right, you’re energized all the time, inspired all the time, and everything just feels good because you’re “the leader.” In my experience, that’s not really how it works.
In fact, one of the hardest parts of leadership is not losing your sense of joy, humor, and humanity while doing the work. Leadership can absolutely be rewarding. But fun? Most of the time, it isn’t.
Leadership means responsibility. It means accountability. It means being the person who often has to hold the line when things are unclear, messy, or uncomfortable.
If you’re leading people, you are constantly teaching, explaining, coaching, correcting, and helping others understand ideas that might not immediately resonate with them. People come to work with different backgrounds, different expectations, and different information. A leader’s job is to help bridge that gap.
Sometimes that means convincing people.
Sometimes it means training people.
Sometimes it means directing the work clearly enough that success becomes possible.
And when things don’t go well, the finger usually points toward leadership.
That’s part of the deal.
People often think leadership is appealing because of autonomy. It looks like the leader gets to make the decisions. It looks like the leader is in control. But the paradox is that leaders often have less autonomy, not more.
Why? Because the leader’s time, decisions, and attention are constantly shaped by the needs of the people they serve and the circumstances of the business.
You might build a thoughtful plan. You might spend weeks — or months — developing an idea that could improve the company, create opportunity, or solve real problems.
Then suddenly the landscape changes.
A new piece of information appears.
A market shifts.
A team challenge emerges.
A completely unexpected curveball shows up.
And the plan that worked yesterday no longer works today.
Back to the drawing board.
This is the rhythm of leadership.
And while all of that is happening, leaders often become the emotional center of the workplace whether they intend to or not. When people are having a good experience, leadership gets credit. When things are difficult, leadership often takes the blame.
That’s part of carrying the responsibility. So if you want to be a leader, you have to believe in something bigger than yourself. You have to care deeply about people. You need resilience, adaptability, and patience that sometimes feels almost unreasonable.
And most importantly, you need to figure out how to take care of yourself along the way.
Because if you lose yourself in leadership, you won’t be able to help anyone else.
So what helps?
First, know yourself. Leadership magnifies your strengths and your weaknesses. The more awareness you have about how you operate, the better chance you have of navigating the pressure.
Second, build a team around you. Leadership should never be a solo sport. Bring people to the table who understand the mission, the direction, and the “why” behind what you're doing. Over time, good leadership means sharing leadership. Passing off responsibility. Creating more voices in the room who can help guide the work.
Third, find small pockets of joy wherever you can. Because leadership isn’t fun in the way front-line work often is. And that’s something that’s easy to misunderstand.
When you’re on the front lines — serving guests, making drinks, building things with your hands, working directly with customers — there’s often an energy and immediacy to the work. You see the results right away. You laugh with coworkers. You feel the rhythm of the day. Those jobs can be incredibly fun. When I was in those roles earlier in my career, the biggest frustrations were usually things like: • Not getting to make the decisions • Feeling like I had better ideas • Not earning as much as leadership • Being tied to schedules and rules
Those frustrations are real.
But what’s often invisible from the outside is the trade-off. Leadership doesn’t just come with higher pay. It comes with much higher responsibility.
More stress.
More frustration.
More uncertainty.
And often a much heavier sense that if something goes wrong, many people — not just yourself — are affected.
The reality is that the financial increase in leadership roles is often a reflection of the scale of responsibility, not a guarantee of a better or easier life.
And that’s a truth that’s easy to miss if you’ve never had to sit in that seat.
So the real question for leaders becomes this: How do we build organizations where people understand the path? Where entry-level roles are respected, growth is possible, and opportunity exists — but also where people understand that businesses operate within real constraints?
Because every company has limits. There are only three resources any organization truly has: Time. Money. Energy. That’s it.
Good leadership is constantly trying to decide how those resources should be spent.
How do we grow the pie so more opportunity exists?
How do we take care of people while also keeping the business healthy?
How do we balance sustainability, fairness, and long-term success?
Those questions never stop. They evolve constantly and leaders are responsible for answering them again and again.
Because if leaders stop asking those questions, culture eventually drifts. Organizations stagnate. What once worked becomes outdated.
Leadership isn’t always fun. But it can be deeply rewarding.
It’s rewarding when you help someone grow.
It’s rewarding when you solve problems that make life better for many people.
It’s rewarding when you build something meaningful alongside others.
If those things don’t matter to you, leadership probably isn’t the right path.
But if helping people grow, building something bigger than yourself, and solving hard problems gives you purpose — then leadership, even with all its pressure, becomes worth it.
Maturing, if you’re introspective and observant has a way of enlightening. Perspectives change and you begin seeing things differently than when you were younger.
The needs and challenges change in life. Growth happens. Something I noticed for myself as I stepped into leadership, then ownership, is that my past beliefs were projections and often pretty skewed. This is pretty normal, and understandable. When you are participating as a leader you’re often without the full picture. Naturally, the human mind attempts to fill in the the grey parts of any story to come to conclusions that feel rational. However, many of our rational decisions are built around what we have learned and absorbed in all the life experiences leading to this moment. Translation? Extremely bias to a pretty short sided box.
I own a company in one of the most expensive places to live in the United States. One of my core drivers in opening it was to provide the best working environment and to work toward a place that provided not only culture, but careers. That’s a continuous journey full of its own challenges but I can say that it’s been successful on a lot of levels. That’s just it, to get to a place where whatever level of success I envisioned is in play will require consistent adaptation to things that work against a seamless flow. The work of an owner requires lots of space to think, problem solve, learn and create solutions before taking action. This is normal. But until I was a business owner, I didn’t realize this. That the people I worked for didn’t share all the info partially because they were figuring it out, partially because it wasn’t my job to fix it, partially in protection, and partially in the need for the high performers like myself to keep performing without distraction because thst performance is a key in moving toward success.
I used to wonder why the owners weren’t still making coffee with me, what they were up to, and often questioned if they lost the spark.
I think those owners knew that if they spent their time being the face of everything while simultaneously having the needs, desires and issues that need solving ruminating, that they may not be able to show up at the level they know they could. Knowing the level of performance that brought success when doing the job they fell in love with, the passion full steam in front of them, creativity to deliver the experience all of that focus necessary while most of the space in their mind being taken up by complex issues, equations to solve, could make someone go crazy. They, like me, are humans with limitations.
I know now that if I want to provide careers this is a huge paradox. I can’t be THAT GUY. No “He’s Him’”. I have to teach everything I know and beliefs to others who can help recreate and teach themselves. The coach, not the star. With that comes new leaders and new owners of the culture.
Anyone who resonates with the ideas set in motion by a culture developer/business owner, who work where the owners once did were hired to do the things that are not required of an owner for success. Do you fix the machines or pay a little more, do you save the money to open a cafe or make a plan to go more into debt? Do you buy new gear and upgrade guest experience because you make more in the long haul but lose money now? People who work for you, like me when I was younger, likely will not be looking at what to do when business metrics change: tariffs, minimum wage increase, tax changes, equipment, loans to grow, loans to pay, HR laws, systems creation, training pathways, etc. etc. etc.
It’s amazing that a business that’s run well looks like it’s a million dollars, but we must remember that twitter is and has always lost money…just be cause it’s open doesn’t mean it’s stacking cash.
These are things young business owners don’t often see at the beginning. These business objectives require so much effort to get right if you’re like we are at C&C. Trying to build a culture that’s meaningful and connective and unique.
I have been really insecure about this. I know I used to assume the owners didn’t care like I did and I absolutely could see it being easy for people to feel the same. Those who have never even seen me Barista like a champion. Why wouldn’t they ask themselves, “is he even good at this?”. I don’t need to prove it to them, but at the same time, I care that they understand or feel that what I/we ask of them is absolutely attainable and beneficial. As when I was young, I didn’t know what I was learning until later and I have to trust through my insecurity that it will be true for those who look at who they are now and what changes came because they worked at C&C.
The more experience I have, the more I see evidence that supports why corporate America is the way it is. Every chance to grow requires money that’s beyond what the business makes to begin with, the real human want to have a life where personal value and identity isn’t solely reliant on the job we have…lest we forget that lots of owners created a business because they love doing what they don’t get to do now: Walt Disney stopped being Mickey Mouse and animating, Gordon Ramsay cooks but not in restaurants anymore, I stopped a-z crafting coffee….same thing right?!! I digress, I don’t fit the same category as those guys, majorly different legacies, but same concept. If owners believe in ideals, a mission and values, they are supposed to create in such a way that those things come to life, not so that the owner can be the idea, product or business itself. In fact, I find it selfish to think it needs to be credited directly to the owner, solely.
But here’s the flip, people follow leaders, owners and visionaries feel like leaders and leaders are where all hope, blame, responsibility, success or failure get placed. Most owners I know want to help and end up getting overwhelmed in the process of attempting to provide something dream worthy. Operations, leases, contracts, P&L, fund raising, investors, endless problem solving, training, relationship building, marketing, build outs, conflict management, inventory, maintenance, training systems and pathways, accountability charts, all things that don’t get trained, but are learned or failed in the process of trying to bring something to life that hopefully makes the world a better place.
I can absolutely see why some businesses sell, why larger corporations with money step in and bring insane formalities that steal the soul of what was, and the part that breaks my heart is that it’s usually someone walking away from a dream vs taking a payout. It’s someone saying, I don’t have it in me anymore and it doesn’t feel like I have the support or belief of the people to see this through.
What I do know, is that starting a business and growing a business to a place where it gives jobs to people & is sustainable often requires a level of sacrifice & hard work that’s un-relatable to those who haven’t had to endure it. Who would want to go on food stamps and live with friends and others in single rooms with a family of 4 when they could just “work” at a J. O. B. But that’s what I did, because of a belief in something Cat & Cloud continues to work toward.
The woman at the taqueria who hasn't seen me for over a year but greets me and remembers to add an extra salsa to my bag, Lizzy & Stacey, some of the best hospitality focused enjoyable baristas in the world, Cole Billings a mastermind of quality, professionalism & fun, Paul Halvorsen, Alissa Rezendes, Sarah Shirley, and so, so many more magical people who make experiences shine, spaces feel attractive, awesome, lynchpins of connection who are consistently asked to be more than, or different, to expand and flex who they are in order to "Fit". These sensitive souls built for connection and empathy, who want to be seen and talk to by all...burn out.
I see our world, our businesses to people into managers, expecting progression by way of position. Force people away from the spotlight they are naturally bringing, the gravity that essentially revolves around their energy when they fill a room with joy. Why? We pay by position, not impact. We look at the wrong metrics and no one has figured out how to do otherwise. Metrics of old, of production. When we only take to impact by way of a P&L method invented for profit efficiency, we miss multipliers, things that are very tangible to human experience, but immeasurable in that P&L, scorecard or business statement. Banks, Upper Management, and those who aren't seeing it personally and daily can't grasp it in the daily stat sheets and statements so through time, we lose the magic. Especially as we grow. We don't bet on or invest in the exact thing that we are looking for and then eventually....we lose it. I fucking hate our way.
Our art and connection becomes lost in things like chatgpt because our need to survive, desire to thrive, to get ahead in order to get back to feeling like we can create and be our authentic self seems to force us into dystopian system of distraction that favors robotic thinking, output, hustle culture & Self absorption. This being counter to who we all want to be at our core as humans. Completely at odds with our true human needs, while in ever pressing stress to connect to human needs. Completely rewarded by algorithms, we slowly isolate more in "success". "Successfully" seen, successfully paid, successfully spending 50 of 52 weeks a year at work...perhaps more because of our side hustles, to take 2 weeks for ourselves in an attempt to get back to baseline, always depleted.
There has to be a better way. These magical people are everywhere and I believe many people haven't been able to access the magic they have at their core because of this system and my heart hurts for it all. The magical people we do have, like the ones I mentioned and the ones you can picture are worth 2x-5x more by way of the impact they make every day compared to those who fall in line with gray behind those eyes. Does anyone else see or resonate with once glowing, to feeling suffocated, trying to fight for the way to break this cycle? The alternative is walking away, but that seems to be the easy way, and often the way that most take. I think there is a different model, I think there is a different way. Do you?