HOW is: 

• The fun part of your job

• The adventure

• Messy

• Full of surprises 

• All the interesting problems you get to solve

• All the paths you’ll take that you didn’t know existed 

• Where you hone your skills

• Where you find your confidence and build your character

• Where you grow

Every week at our leadership meeting we review our quarterly goals. We know WHY we’re pursuing them, we can envision WHAT success looks and feels like, but we don’t know HOW we’re going to make them happen. Without fail, at the end of every project cycle, we’ve accomplished all the things we didn't know how to do just a few months ago. 

In every worthwhile project I've brought to life, belief and desire have come before understanding. When I believe in the project and myself, and am eager to do the work, I always figure out HOW. When I don't fully believe or simply don't want to do the work, HOW escapes me. 

HOW is the work of leaders—people who willingly step into the unknown despite their fear. 

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My friend who has a small company is in the process of clarifying and sharing his vision with his team. Sharing your dreams for the future is an exposing process. Not only does it reveal something very personal, it puts you on the hook. I’ve spoken with many business owners who hesitate to share their vision for fear that it might not be well received or that they might not be able to deliver on their promise. 

My friend is starting from a great place though because, like most small bootstrapped businesses, the main reason that his team has chosen to work with him is that they believe in him. They might not even know why, since he’s yet to fully paint the picture of what they're working toward. It’s likely not a rational decision but rather one based on gut feelings or instinct.

While belief in the individual at the helm is essential, a cult of personality doesn’t scale. For a business to grow, the primary cultural touch point has to be with the mission, vision, and values of the organization, and not a specific person. 

If someone needs to interact with me to feel connected to the heartbeat of Cat & Cloud, we’re missing the mark. While it’s flattering that some people believe in me, I’m certain no one's highest calling involves waking up and thinking “I’m incredibly passionate about working for Chris. Working for Chris is my dream!” I do know people wake up and think “I’m incredibly passionate about taking care of people and providing them with amazing experiences that connect them more deeply with the people around them.”

As leaders, we can help our employees achieve their goals by helping them engage with what they’re passionate about at a higher level, but we can’t impose our goals on them, they must willingly accept them as their own. This is one of the great things businesses can do in our culture—be a conduit to connect people with and act on ideas they deeply believe in.

As the owner, you’re still the stakeholder of the mission and will set the standards, but it’s important not to confuse your organization's mission as an ideal, with you, a human.

In small organizations, we often don’t have the bankroll to afford top-dollar talent. Most of us are playing Moneyball: we take passionate, culturally aligned people who love the work, allow them to lean into their strengths, and coach up (or ignore) the weaker parts of their game. 

Sure, we need a certain level of competence—but the idea that we will find the “perfect” person for any given job is unrealistic. This goes for us owners as well. I’m passionate and thoughtful, but I’m no Bob Iger. 

At Cat & Cloud, we’ve gone through different phases of hiring frameworks. In the early years, we exclusively promoted from within. A well-intentioned cultural gesture but we sometimes needed to fill roles for which we didn’t have anyone with even the base level of skill or desire needed. 

So we loosened up the reigns. Here’s what I’ve noticed:

Since giving ourselves permission to hire externally for higher-level positions, in the past three years we’ve only done it once. (Our marketing wizard Micheal Wiser who was also our first guest ever—he’s about as internal as an external hire can get.)

Many gaps can be filled by less than part-time third-party help. (We have someone who helps us work on grocery-specific wholesale who we could never justify bringing on full-time, but has helped us grow in areas where we aren’t experts.)

As we’ve grown as leaders, we’ve become better at clearly communicating expectations to people and identifying good job fits. This has led to us being able to fill most of our positions internally. In the past, I don’t think it was a case of not having the right people but more so us not having strong enough leadership. 

Scars and Scabs

All things being equal (or even slightly unequal), my gut steers towards filling positions from within. There’s something about having someone on staff who is culturally comfortable in your organization and still wants to grow with you despite your scars and scabs. Just as no job candidate is perfect, neither is any organization. Rose-colored glasses and unrealistic expectations can make coming into a small, bootstrapped organization a bit of a shock for outside hires. Plus it’s way more fun to give someone a shot and watch them succeed than to just assume that an outsider with a more “professional” resume will fix all your problems. 

Happy New Year. Happy hiring.

I once had an employee who was enthusiastic and talented. In some ways, he was overqualified for his role, and in others, he was very green. He had a good amount of freedom, contributed to interesting projects, and worked closely with the ownership team. He had a lot but wanted more. 

I’m an advocate of asking for what you want. Think you’re worth three times your salary? State your case and cite examples to back it up*. But the reality of running a bootstrapped independent business is that even when that case is compelling (it usually isn’t), there’s often no way we can meet the demands. 

When these situations arise I do my best to break down the scope of the business and our limitations. I’ve made the mistake of dangling carrots in the past. I believe in Cat & Cloud but the truth is there’s no way to tell what our situation will be in 1, 3, or 5 years, so leading someone on in hopes that we’ll be able to meet their needs in the future is something I refuse to do. We’ve also made the mistake of giving raises we can’t afford based on future projections, making our monthly cash flow numbers out of wack.

In this particular case, the employee was adamant “My time is now. This is what I need.” Fair enough. But we couldn’t meet his demands. There was a mismatch between his life situation and our business's resources.

Not all places of employment are created equally. Some careers simply pay more than others. A brain surgeon makes more than the average cook but less than the CEO of a Fortune 500 company. Even in the same market, some companies have huge outside investment and are larger, or more profitable. 

Not all life situations and expectations are created equally either. Some people have more financial flexibility than others. Some are happy to live a more minimalist lifestyle to work in their chosen field. Some people "need" a Porsche while some are cool with an '85 Camry. 

I’ve taken pay cuts to be where I want to be. I’ve chosen to commute 4 hours a day for average-paying Barista work. I’m also no stranger to running out of runway at work. When what was next for me simply wasn’t on offer at my current job, I was forced to make a change. No hard feelings: every job I’ve quit was a job I’ve enjoyed. 

Employees need not feel guilty for leaving a job to advance their career or improve their life situation. Small business owners need not feel guilty for being limited in what they can monetarily provide. On both sides of the equation staying true to your vision, being grateful for what was, and transitioning gracefully seems to be a solid framework. 

* When you’re advocating for yourself, keep it classy. Approach your pitch from a place of service, focusing on what you can give rather than what you hope to get or feel like you may deserve. Do your best to put yourself in your boss’s shoes. In other words, make your pitch less about you and more about your employer.

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People who create extraordinary things are obsessed. The most renowned chefs don’t have a casual relationship with food. They don’t pigeonhole their work into a 9 to 5 schedule. They constantly ruminate on the details, lose sleep in pursuit of new ideas, and are consumed by their craft. 

This pursuit of excellence has a trade-off. Something has to give. It might be health, personal relationships, or family. If they weren’t willing to let any of these suffer, they wouldn’t be in the spot they are—someone willing to make the sacrifice would be. 

The important thing is not to get caught up in the illusion that being one of these people is better than not (some days I feel like I want to be one of these people, others I’m certain I don’t), or that you can be one of these people and still live a balanced life. You pay the cost either way. As with most things, what you’re willing to give up will determine how far you can go in any one direction.

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I made espresso on a tiny Japanese truck for my friend's open house, here's a peek behind the scenes:

I recently had the opportunity to attend the Blue Bottle Studio experience. It’s a multi-course coffee tasting menu with all details attended to. It’s probably the closest thing to a 3 Michelin Star experience in coffee. 

As I’ve shared the experience with people I’ve fielded multiple questions in the vain of “Was it worth it?” “Was it the best coffee ever?” and “Do you think it’s actually a sustainable business model?” 

All of these questions, while honest, miss the spirit of experiences like these. I see this experience less in terms of strict coffee quality or a new business model that will become the future of coffee and more in terms of pure art: What would it look like to create a place in time where everything else melts away and you’re fully immersed in what you’re experiencing?

Quality and value live in the eye of the beholder. Is a 1970 BMW 2002 better than a brand-new M3? Is a 3 Star Michelin meal better than the best street tacos you’ve ever had? I don’t think it works like that. 

I think more of this artistic mindset would serve us in our personal and business endeavors. Instead of worrying about being the best and constantly comparing ourselves to others, we can focus on the people we seek to serve and approach that service from our personal point of passion. 

A business will always have elements that live outside the purely artistic space but where we start our process informs how it evolves. A business where numbers are the jump-off point looks a lot different than a business in the same industry that puts artistic expression first.

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On-Trend

Trends are momentary bursts of faux cool driven by boredom, short attention spans, or lack of purpose or point of view. If your goal is to be on-trend, you’ll spend your life chasing the dragon and being one step behind. 

On-Brand 

On brand means delivering on your promise—honoring your mission and values. This might not make you the most on-trend company at any given moment, but you get to lead, not follow. When you’re consistently on-brand you have a strong foundation that allows you to play with popular culture rather than being defined by it.

It’s easy to take the things we do every day for granted—another cupping, another shift, another batch. But what if we approached each task at work like it was a class we’d paid for? How much more would we learn if the next cupping wasn’t “just another one of those” but rather a concerted effort to level up our skills?

We’ll fly across the country to attend a tradeshow or spend hundreds of dollars on a workshop, yet stumble through our day-to-day work half asleep focusing on getting through it rather than getting into it. 

Most of us have a wealth of knowledge all around us just waiting to be tapped into—people who are eager to share the things they love with people who share their passion. The formula for tapping into it is simple:  Show up with intention, pay attention, act on your curiosity, and don't take your current opportunities for granted.

How isn’t something you know before you start your project. How is something you figure out along the way.

Why and What are good to know before you get going:  

“We believe positive, memorable experiences bring us together and lift us up—we’re going to start a coffee roasting company with this idea at its core”

But we had no idea how were we going to get financing, find a space, build it out under budget, create our systems hire the right team, train them, etc.

How is the unknown. That’s what makes How the fun part.

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The second Tuesday of each month, we host orientation. 

Orientation is an opportunity for new hires to get acquainted with our culture—we introduce them to our mission and values, the communication tools we use, and we share stories.

Our orientation has been through many evolutions, it’s currently in its most simplistic form and we’re in the process of expanding it, but my advice to business owners who are thinking about doing an orientation is to not overthink it. Something is better than nothing.

A three-part template for creating a simple but effective orientation might include:

• Your history - how did your company come to be?

• Your mission and values - why do you do the work you do?

• How people can contribute to the mission and values through the work they do? 

(Bonus point for putting together a goodie bag - ours has coffee and a gift card)

Orientation also helps relieve some of the tension of being the new person—when you’re thrown into an established team with no cultural context, it’s easy to feel like an outsider. Having an idea of what True North is, even if you don’t know how to get there, points everyone in the same direction and creates an immediate sense of shared purpose and camaraderie. 

Work feels more meaningful when you understand why you do what you do, and an orientation helps lay the cultural groundwork for that understanding.

In the past seven years of running a business, something that’s becoming painfully obvious is I always find what I’m looking for. 

• Looking for evidence of people doing a half-ass job, I can find it. 

• Looking for evidence of my business partners conspiring against me, I can find it. 

• Looking for reasons it’s not worth it to own a business, I can find plenty. 

On the flip side: 

• Looking for people who care deeply about the work they do, I see them every day.

• Looking for reasons I’m lucky to have Jared and Charles by my side, the list is endless. 

• Looking for evidence of why owning a business is one of the best decisions I’ve ever made, I have it in droves.

The story we tell ourselves influences our reality so much that it might as well be a crystal ball. I’m not suggesting we should ignore something that is truly broken, rather I’m suggesting that belief influences action which leads to evidence that reinforces that belief. 

If my interactions with my coworkers are rooted in the presupposition that everyone is out to get me, how do you think those interactions will go? 

• Initial Belief: Everyone is out to get me

• Action: I act like a jerk to my coworkers

• Evidence/Reaction: People treat me like the jerk I am

• Reinforced Belief: Everyone is out to get me

If my interactions with my coworkers are instead rooted in the presupposition that everyone wants me to succeed, how do you think those interactions will go? 

• Initial Belief: Everyone wants me to succeed 

• Action: I am kind and generous to my coworkers

• Evidence/Reaction: People respond positively to me and go out of their way to help me

• Reinforced Belief: Everyone wants me to succeed

Starting Cat & Cloud required belief. If we added up all the positive attributes each of us brought to the table: years of industry experience on both sides of the supply chain, financial expertise, an engaged group of people who followed what we were doing, etc., no combination of them could produce any evidence that could answer the questions: “Will this business succeed?” or, “Is starting this business a smart move?” 

So instead of looking for evidence, we started with belief. Belief isn’t a guarantee, things might not work out with it, but things definitely won’t work without it.

Bad days are inevitable. Days where we don’t feel like doing the work, don’t want to smile, don’t feel like being friendly. How we feel is a part of our experience for sure, but how we feel doesn’t have to dictate how we show up. 

How we choose to show up when we don’t feel like it highlights the difference between a professional and an amateur. The professional makes a commitment and honors it—they show up for their guests and team whether they feel like it or not. The amateur does the work only when it suits them.

The professional is generous, the amateur is selfish. The professional is an adult, the amateur is childish.

We all have baggage. Some days it feels heavier than others. But no matter how much baggage we’re carrying, choosing to be a professional requires we check it at the door.

On a call last week with a specialist in EOS (Entrepreneurial Operating System), we were discussing having the right people in the right seats, and the facilitator dropped an acronym on us: GWC. He explained GWC is a tool that requires you to ask three questions about the people on your team: 

Do they get it?
Do they want it? 
Do they have the capacity? 

“Wanting it” is essentially enrollment, something Seth Godin has painted a clear picture of for me over the past few years. You can dig into his blog or podcast for deep dives but this nugget will get you going: 

When we’re actively enrolled in a journey, it’s on us. That’s the requirement once you choose to act professionally. You know the terms, the dates, the structure. It wasn’t even fine print. It’s simply the structure you agreed to be part of. 

Of course, enrollment is frightening. Because enrollment confers responsibility. “This is something I’m choosing to do.”

Having the capacity to do a given task seems cut and dry although I’ve definitely been guilty of trying to shoehorn people into roles that they simply don’t have the chops for because, well, mostly because I liked them or I felt like they deserved to advance in some way. Of course, this isn’t fair to them, the organization, or myself. 

But it was the “G” that struck me. Do they get it? Do they have that natural intuition for the role? It felt like a question I’d always wanted to ask but never did because I had no way of quantifying an answer. Even something like values alignment falls short of this gut-level feeling. 

I’m not sure quite sure I’m defining “Get it” in the way that the EOS system is using it, nor can I attest to the quality of the EOS system itself, but the call did help me name something that I deeply desire: to work with people who get it, and pushed me to quantify what getting it even means. From the perspective of a business owner, I'd say someone who gets it consistently and naturally produces work that lines up with or improves upon the vision you see in your head. And with people who get it, even when the work is hard, the process is enjoyable. 

Thinking is an essential part of the creative process but it’s also an obstacle. It’s kind of like salt—you need it for your food to taste good, but too much of it ruins the meal.

There’s a sweet spot for thinking and seasoning, but when you’re not sure where that is, I’ve found erring on the side of less is the way to go.

(This isn’t an excuse to do thoughtless work, just a nudge to get out of your own way.)

It’s hard to say if Cat & Cloud started in 2016 when we opened our first brick-and-mortar, in 2014 when my first attempt at business ownership failed miserably, in 2009 when I started working with Jared, In 2006 when I dropped out of school to make minimum wage and wash dishes at my (then) dream job, in 2005 when I entered my first barista competition, or in 2003 when I decided that I was going to take this inexplicable new found love of espresso seriously. 

Although it might seem that your career path is something you’ll start “later,” I promise you, you’re already on it. Even if you switch industries, every time you show up to work you’re laying the foundation that the rest of your career will be built on. 

The advice on how to engage with work is endless: Show up with intention, pay attention, learn as much as you can—not just of your tasks but how the organization runs, share what you’ve learned, and the list goes on. But it all starts with giving a shit. It all starts with knowing what’s at stake: your career, your habits, your reputation. So sure, you could phone it in at your “crappy” job, but it’s important to know that you’re the one who’s missing out.

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Ever notice how difficult it is to write your bio? Whether it’s something formal like an “about” page or something casual like an Instagram bio—trying to squeeze your entire existence into a paragraph feels impossible. And for good reason, because despite how many descriptors we list for ourselves, we are all more than simply a collection of labels. 

I can tell you I’m a business owner, skateboarder, father, husband, and writer, and you still don’t know me. There are scores of other people who are those same things who are almost nothing like me, and there are scores of other people who are not those things that I have plenty in common with.

As a business owner, it's been hard for me to come to terms with the idea that the way people perceive me is mostly out of my control. I can hope that if I show up in service with others' best interests in mind, people will see me in the way I’d like to be seen, but there’s no guarantee. My team's interpretation of me is created by some combination of how I interact with them, my track record, and the story in their heads (with the last one likely being the most powerful).

Perhaps the idea that certain people could or even should, fully know us is a flawed one. In the same way that we can't be everything to everyone, we also can’t be fully seen by everyone—it actually seems a bit egotistical that we could be.

For practical bio advice, I’ll point you to Austin Kelon’s Show Your Work: “Bios are not the place to practice your creativity. We all like to think we’re more complex than a two-sentence explanation but a two-sentence explanation is usually what the world wants.” 

This taps into the heart of the matter—bios aren’t the place to fully express ourselves, they’re useful tools to connect the people we hope to serve to the work we do. This is true everywhere we seek to express ourselves: most people will only know a tiny slice of us, and that’s ok.

On our way to a Santa Cruz community event featuring a smorgasbord of local small businesses, I half-joked to a friend that I’m terrible about showing up for my local community. 

He replied, “You have a space where hundreds of people gather every day to have fun, tell stories, and share laughs. The community is better because of your shops, it seems to me like you’re doing plenty.” 

He was articulating something I already believed. That our work, when done with love and intention, is a form of community service. 

Most of our social interactions day in and day out, revolve around businesses. Going out for coffee, a lunch date, grabbing a drink after work, not to mention work itself. This is why businesses are so powerful—they shape the world around us (sometimes for the worst).

So if you’re feeling the pressure to run a solid business and also do good on the side, a better strategy might be to get clear about what you do and don’t do, and integrate the change you hope to make into your day-to-day work.

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I’ve been lucky enough to have meals at 3 Michelin Star restaurants and despite the cutting-edge preparation techniques, absurd wine lists, and bespoke table wear, none of them have made me feel the way my grandma's homemade tortillas did. Just a few ingredients rolled out with a wooden dowel borrowed from an old clothes rack, cooked in a modest home.

Although worlds apart in some ways, both experiences were created with love, both were gifts from people who care to people who appreciate those gifts, and both formed life-long memories.

Money is a convenient excuse to hide behind because no matter how much you have, what you wish you could do requires just a little bit more. But money doesn’t create experiences, people create experiences, and you're already a person, so you already have everything you need.

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In preparation for a recent family trip, I deleted Instagram from my phone so I wouldn't be tempted to randomly open it up and scroll for no reason. 

When I returned home, I struggled to find a compelling justification for re-downloading the app. Despite considering myself to be disciplined, I find myself mindlessly scrolling (“relaxing”) or sharing mindless memes (“connecting”) far more than I feel comfortable with. 

I definitely see the case for businesses or a tight-knit family or social circle. The waters become murkier when we’re lost in the middle-ground: would-be influencers trading a significant amount of time and mental bandwidth in hopes that they’ll be the next one in a million. It’s not that different than spending all your money on lottery tickets. Sure, someone’s going to win, but it’s probably not going to be you. 

I keep coming back to this question: Is the small amount of attention we’re getting worth the astronomical amount of time we’re spending on these platforms? I’m pretty sure most of us aren’t going to look back in 10, 20, or 30 years and say “I wish I would’ve spent more time on TikTok.” 

Despite all that I re-downloaded the app and posted a few stories of my car today. How’s that for self-control?

Every Friday at 9 am we have our executive meeting. It’s a place where we discuss financials, check in on big projects, do some good old-fashioned venting, and every once in a while, shed a tear. 

Every company-wide initiative we roll out gets shared with the executive team first. Sharing with this team helps us bench-test our ideas and through the conversation, we’re able to understand our own ideas better, all while getting feedback and insight that we might not have. While we can’t outsource our vision for the organization, having people put our ideas through the wringer is invaluable. 

The meeting started its life as a Team Leader meeting—anyone who ran a department or store location, and at some point, it transitioned into the “Executive Meeting.” I don’t love the name—it sounds a bit corporate so I’ll often refer to it as our “upper leadership meeting.” Over the years it’s gone through multiple incarnations both in its format and in the people that attend. Basically, it’s a group of people whose opinions we trust that have earned their spot with the passion they have for sharing our mission and values, the way they carry themselves at work, and who have a track record of turning ideas into reality.

I have a complicated relationship with this meeting. Some days it feels like the highlight of my week, and on others, it feels like we’re wasting our time. Sometimes we come prepared, sometimes we wing it. Sometimes we try a new format and stick to it for a month only to slip back into chaos. Sometimes I talk too much. Sometimes I don’t say enough. Even though my two business partners and I have clearly defined roles, we’re all passionate about every aspect of the organization and it’s not uncommon for us to have different opinions on the best way forward.

While my natural inclination is to have everything completely buttoned up, sitting through a disorganized meeting every once in a while feels way better than feeling disconnected because we have no communication with our team. Despite all its imperfections, the spirit of the meeting is true.