When we opened Cat & Cloud we hired eight people. It wasn’t a stretch for me to look at those eight people and imagine that one day they could retire with us. I wasn’t sure how it would work, but it felt reasonable—if they grew as the organization grew, they could have lifelong careers with us.

Six years later our upper leadership team is exactly eight people. Two of them have been with us since day one but most of them were brought into the fold at different points on our journey.

We currently have seventy employees, and it’s much more difficult for me to look at those seventy people and imagine they could all retire with us. Not because of some size cap we have but because our pace of growth considering our resources (we don’t have huge amounts of external funding), and standards (quite high), make us more of the tortoise than the hare.

It’s tempting to try and solve the lifelong career equation. What kind of growth would be necessary to provide an A-Z path for everyone on staff at all times? Since that equation spins the growth flywheel, it’s easy to see how the numbers scale exponentially—if we solve for seventy, we’re faced with a problem of hundreds and then thousands.

This also makes a lot of assumptions. It assumes that everyone who experiences what we have to offer would decide to stay. That every person, each one with their own hopes and dreams, will discover that the best place to bring their dreams to life is with our organization. As business owners we tend to be proud of what we’ve created, and rightfully so, but it’s a bit egomaniacal to think this way.

Shuffling the Deck

Although people start companies, I’ve always found individuals to be far more interesting than organizations. Maybe it’s the compromises that come with the realities of business or that chasing popularity and growth tends to (counterproductively) water down a strong point of view. I feel a world in which more people are speaking directly about what they believe in and can do it in a financially viable way is richer than a world in which we all work for “Big Corporation X”.

Don’t get me wrong, there’s a place for the big. I like that Disney has the resources and team to be able to create Frozen II, but for me, this is more of an exception than the rule. Small is personable, small has a point of view, small is nimble, and small in size doesn’t mean small in impact.

Taking into account all of the above, it’s clear what our opportunity is.

We can choose to be a place of growth. A place where people can learn about themselves, learn skills that will help them on their journey, and learn what it means to be of service. A place where people can see the magic of their contribution and begin to realize their potential.

For most people who walk through our doors, we’re more of an incubator than a forever home. This isn’t a trivial role to play—the experiences we create for the people around us shape our lives and theirs. The journey matters.

A certain percentage of people will stay. The journey on offer and the journey they’re looking for will be a perfect fit. This blows me away. The fact that we’ve created a place that someone wants to make their forever home is incredible.

People will always leave. As business owners, part of our challenge is to embrace the fact that keeping people isn’t as important as helping them find their voice and ultimately their happiness.

If we’re doing it right, every time the deck shuffles we’ll draw a better hand than before.

“And now we get to officially start this company for real.”

This is something my business partner says when we discover a way to push past something that’s been holding us back.

This happens often so the phrase gets thrown around often.

I was poking fun at him yesterday after a brainstorming meeting: “You say that every week!” It felt even more ridiculous given this Friday is Cat & Cloud’s sixth birthday.

It made me chuckle and reminded me that today, right now, is a moment you can decide to do something you’ve been meaning to do, say something you’ve been meaning to say, and be who you ought to be.

The opportunity in front of you doesn’t care if you’re how old you are or how long you’ve been in business. Every day you can make the choice to embrace that opportunity or not.

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I made a video to commemorate Cat & Cloud's sixth birthday. Get a peek inside all our locations, some fun flashbacks, and a look at WHY we do what we do.

The question isn’t: Will there be problems?
The question is: When you notice a problem, what are you going to do about it?

Paths to consider:

Taking Action To Fix A Problem

• Empowers you

• Makes the problem your responsibility (even if it’s not your fault)

• Problem gets solved 

• Life is better for you, your team, and your guests

Complaining About A Problem

• Strips you of your agency

• Makes the problem someone else's responsibility 

• Problem still exists 

• Life hasn’t changed for you or anyone around you

I’ve been guilty of being the complainer in the past, and while complaining gives the illusion of productivity in the short term, it’s not a great strategy for making things better. 

Sometimes ignoring the problem is the best solution for the time being. Multiple problems always exist and some need to be actively ignored so we can focus on what’s most important. 

So while noting, logging, and ignoring is a viable option, simply complaining without offering a path to improvement is selling yourself short.

We all have blind spots so a certain amount of truth-telling is necessary to improve, but if you only ever bring problems to the table and not solutions, you might be the one with the biggest problem.

I created my first crude cafe business plan in 2005. Cat & Cloud’s first retail store opened in 2016. At some point in this time window I knew enough to get started but didn't believe in myself enough to follow through.

There were other factors in creating something that worked—my great business partners for example. But I’d known them for years at this point. It’s not like they weren’t around, it’s that they couldn’t appear as business partners until the choice was made to start the business.

So while a certain level of expertise is needed to create impact, if you find yourself continually stalling on your projects, it’s prudent to ask yourself if you’re preparing or simply avoiding responsibility.

Two things stick out to me here:

1. You get to pick your pain. The pain of moving forward despite the uncertainty (that hurts now), or the pain of not trying (that hurts later).

2. The only way to honor your future self is by trusting your current self.

A package deal.

I’ve gambled with my reputation by creating garbage and it usually doesn’t go well. On the rare occasion that it does, it still doesn’t feel satisfying.

So two questions I’ve learned to ask myself before taking action are: Who do I want to help, and who do I want to be?

In a static environment, it might be enough to know our systems and execute them every time.  

In a dynamic environment (think guest service), we need to understand our systems and the intention behind them, execute them nearly every time, and occasionally bend them in a way that still showcases the spirit of those systems. 

The Professionals Paradox: Once you get to a certain level, playing it by the book holds you back. 

There are a couple obvious problems here:

1. Mediocre performers often think they’re much better than they actually are. (see the Dunning–Kruger effect)
2. It’s easy to fall into the routine of bending the rules more often than you should. 

So what to do?

Barry-Wehmiller CEO Bob Chapman provides one of my favorite nuggets: “Machines, systems, and processes exist to serve people, not the other way around.”

If I were forced to make a list I'd say to bend the rules you must at minimum:

• Know the rules

• Understand the Why behind the rules

• Do it in a way that makes the guest feel completely taken care of

• Do it in a way that doesn’t disrupt other people's workflow

• Understand that bending the rules never means skimping on quality

• Understand the difference between cutting corners and creative problem solving

If it’s unclear how you might bend the rules while doing all of the above, play it by the book for now.

A six-point cultural business plan framework.

For Your Organization

• This is what we do.

• This is why we do it.

• This is how we do it.

For Your Team

• This is how you can contribute. 

• This is the impact of your contribution.

• This is how you can grow while contributing.

Get clear on these things and you’re on your way.

We were sitting around the roastery reading industry trade publications when one of our roasters asked: “When are we gonna be in that magazine?”

My answer: “When you write something worth sharing.”

I rifled off six or seven ideas for articles that this person was more than qualified to write.

Of course, that was the easy part. Brainstorming might be part of the creative process, but ultimately to be creative you have to create.

So go ahead, write that article. Yes, I’m talking to you.

Two Kinds Of Value

In his 2002 Dartmouth Commencement Address, Fred Rogers taps into the idea that we are all incredibly special, and the things that make us so go beyond what we can see or touch.

How does that specialness manifest?

It isn’t celebrity or fortune. It manifests as love. Not necessarily love given or received, but the worthiness of all of us to be loved.

As he puts it: “You don’t ever have to do anything sensational for people to love you.”

This speaks to one kind of value: our intrinsic value as human beings.

But there’s another kind of value. The value that others assign to us not because of who we are at our core, but because of the work we do.

Think of your favorite musician or artist. You probably don’t know them personally and they probably don’t know you, but that doesn’t take away from the fact that what they create has a very real impact on your life.

They have shown up in service to you and you assign them value because of that.

It’s a trap to conflate the two types of value. We must make the distinction between the value of our service and the value of ourself.

People won’t automatically spend their precious time and energy engaging with the work you do—you have to earn that opportunity.

On the flip side, if you’ve just had a project go down in flames, that doesn’t make you a failure.

Your Work

While I understand the sentiment of self-help quotes like “You are not your work.”, I think it’s problematic to completely dissociate ourselves from our work.

Case in point: You are not your friends, but the company you keep has a huge impact on your life. Best to choose your friends wisely.

When I say work I’m not talking about a specific job, but about the attitude, energy, and intention we carry into any given project. The job we have isn’t directly in our control, how we approach our work is.

You can have what most people consider to be a menial job (I don’t think there is such a thing), and still do great work.

The connective power of our work is what gives it meaning beyond ourselves. If we have no personal connection to our work, it seems absurd to expect other people to connect with it.

So while I hope you find value in being you and having the people around you love you just as you are, I’d also love to see you engage deeply with your work and create something inspired.

One of the things I’ve been working on the last couple of years is letting go of this overly-apologetic coaching style I developed somewhere along the way.

I can trace this to two things:
1. An unnecessary overcorrection of my natural, incredibly direct style.
2. An insecurity that what I’m bringing to the table might not be the best idea.

Feeling compelled to soften the feedback blow by being apologetic with our asks betrays us.

It reinforces the idea that feedback is a punishment for doing something wrong and not the opportunity for growth that it is, and it erases the chance for us to share our passion with others.

Approaching someone with your head down, wearing a frown, and leading with “I’m sorry, I know this is annoying and totally extra but…” isn’t the way to inspire.

Holding your head high with a confident smile, and leading with “Let me show you something.” is a better strategy.

I see these same apologetic disclaimers pop up in creative work as well.

"If I had more time it would have been better."
"It’s my first try so..."
"I wish it looked like..."
"It’s not as fancy as..."
"We don’t have a ton of investors so..."
"It didn’t come out exactly how I wanted."

Telling us how your work has fallen short of your expectations isn’t helping us connect more deeply with it. It doesn’t make your work more compelling or help us feel sympathy for your creative challenges.

We don’t need your work to be perfect. We need it to be inspired and have a point of view.

We need it to change us in some way—to take us somewhere we didn't even know we could go and that’s unlikely to happen if our delivery is self-sabotaging.

As a creator, you’ll still see the flaws, learn from your experience, and know that next time will be better—but this is where you are right now, and it pays to own it.

Create something and share it with no excuses. Because if you don’t back your work, who will?

Things I’ve learned about solving problems while running a business:

One person can come up with a workable, even amazing solution.

A small team can generally come up with a better solution than an individual contributor, provided the group members are skilled.

A large team will generally come up with a worse solution than an individual contributor.

Some opinions carry more weight than others.

To have your opinion count, you must have expertise in the area in question. Not everyone gets to weigh in on every issue.

Fresh eyes can be good at certain points, but fresh eyes too often can bog a project down.

Not everyone will be perfectly happy with every solution, and that’s OK.

Fostering growth means letting people take swings before they're ready. Pick their projects thoughtfully—the goal is to empower, not overwhelm.

My problem-solving prescription:

Make decisions with the smallest viable team of experts who have the perspective needed to effectively put the decision into action.

Once a course of action is decided on, take the time to share the Why behind the What. This creates a learning moment, connects the decision to the values of your organization, and expands the capability of your team over time.

One of the perks of sitting at the bar is the theater—watching the bartender build something for you in real time.

Last night I ordered a quite expensive Manhattan only to find it was pre-mixed. The bartender shook a few dashes of bitters into my glass, poured in my Manhattan from an unmarked glass bottle, plopped in a cherry and called it a day.

No seeing the bottles of spirits, no mixing glass, no stirring, no straining, no theater. 

I felt a bit robbed. 

I took a sip.
Delicious.
But anticlimactic. 

While the drink was worth what I paid for it, the experience was not. 

It’s the square–rectangle relationship.

While all great experiences require a high degree of quality, quality alone doesn’t guarantee a great experience.

Note: Sitting at the bar I watched the bartender build dozens of drinks from scratch but none of them were for me, so while entertaining, the action didn’t quite connect. It's like watching a cooking show and seeing the chef finish prepping a cake, pop it in the oven, then immediately pull a different finished cake out of the other oven. You definitely baked a cake, but you didn't bake it for me. 

It’s easy to fall into the trap of thinking that making something better for you is the same thing as making something better.

Before you create a new system or destroy an existing one, take a beat, identify who else this change will affect, and seek out perspective from those people.

Then ask:

Is this change net positive?
Is this change worth the effort?

There’s always an infinite list of things that could be marginally better, and most of these things are worth ignoring. The goal isn’t to simply do work, but to do work that will move the needle in a meaningful way.

Workplaces are ecosystems. Your actions affect your team, your organization, and your guests.

Focus on the things that will create the biggest positive change for the most people, and leave the rest alone.

This isn’t to say that details don’t matter, they do, but I’ve found when you attack the big things, the details have a way of sorting themselves out.

How to make meaningful progress:

Get really good at ignoring all the things you’re supposed to be doing and focus on the things that need to get done.

At any given time there are more things that could be improved on than things you can possibly do. Action is required for progress but restraint is just as important.

You can do anything, but you can’t do everything.

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Things feel different from the other side of the counter.

Go stand in line at the coffee shop you work at, call the customer service line of your company, or put on a disguise and sit in the reception area of your office.

You'll likely see something you don’t like, and that’s good, now you can fix it.

Some of my favorite experiences revolve around seemingly ordinary things done in extraordinary ways.

A confidence-inspiring haircut. The coffee shop that feels like it was built just for you. A dining experience that blows your mind and brings you closer to the people around you.

The people that create these experiences are more than just a Barber, a Barista, or a Chef. These people are artists and leaders.

These people have decided their job title has nothing to do with the level of pride they take in their work or the attention to detail it commands.

These people choose to go above and beyond because that’s the kind of person they want to be and because they understand how their work impacts the lives of the people they serve.

These people respect their craft.
These people respect their guests.
These people respect themselves.

Will you choose to be one of these people?

I wanted to make skate videos in high school.

At the time, there was no widely available or affordable video editing software (I didn’t have a computer anyway), so I improvised.

I connected my Hi8 camera to a VCR with AV cables.

I used the record button on the VCR to record clips onto the tape in the order I wanted them.

This was tricky to do because the Record button had a lag—I’d push it, then about a second and a half later it actually started recording, so I had to build in that buffer time, and if I messed up, I had to start all over from the beginning.

I had no way to generate titles, so I wrote them on a piece of paper, filmed them, and edited them in with the above method.

That was phase one. I now had a collection of rough sections - one for each of my friends.

To add music and make the master tape, I borrowed another VCR from a friend.

I connected the first VCR (containing the rough sections) to the second VCR. I bought a cheap audio Y cable from Radio Shack and I ran the skating sounds from the first VCR into one input, and audio from a tape player in the other.

I repeated the recording process above, timing the starting and stopping of the music into the mix. Again, if I messed up at any point, I had to start all over from the beginning.

When it was all said and done I had a skate video of my friends, complete with titles, music, and a credits section. It didn't look like a professionally done video, but that wasn't the point.

I invited everyone in the video to the “premiere” (pizza and soda at my dad's shop).

It’s one of my favorite memories.

It’s easy to see this as a “back in my day” rant, but it’s not. It’s a story about commitment and creativity. Despite how much of a pain in the ass making the video was, it never occurred to me that not doing it was an option.

I’ve used this method with various projects—doing things that most people would see as more trouble than they’re worth. But they were worth it to me, so I found a way to bring my ideas to life.

Most of these projects didn’t require brute force, they required making a commitment and being happy to work within whatever limitations existed.

Commitment takes excuses off the table. When there’s no option for excuses you’re forced to get creative.

What could you create if you decided you had to?