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Build a Culture That You Would Want to Work For
Counterintuitive lessons on culture for founders
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When I first started Chezie with my sister, I thought a lot about defining our company culture. I had just left a job in consulting that I wasn’t thrilled about, and I was legitimately excited about building a culture from scratch.
As our team has evolved (currently just two founders and five contractors), I've learned that what most founders are told about company culture doesn't always apply to early-stage startups.
Company culture is the least "hard" of the core components of building a company. While established frameworks for product development, operations, and finance exist, culture is fluid and specific to each company's unique circumstances.
So, instead of sharing conventional wisdom, I want to walk you through how my thinking about company culture has evolved and why you might want to reconsider what "good culture" means for your stage.
Defining Your Culture
The golden rule of company culture is to create a place where I want to show up daily.
Looking at Chezie, I wanted to build a company that:
Promotes a healthy work-life balance (even if that's aspirational in the early days)
Moves quickly and gives people real autonomy
Serves as a career catapult for ambitious team members
That last point is crucial. I understand expecting someone to stay at your company forever is unrealistic. People grow, and you should want ambitious people on your team who will eventually start their things, join another company, go into non-profit work, or chase whatever goals they have for themselves.
Your company should be a springboard that gives them the confidence to go after those goals.
Creating Your Core Values
We didn’t start to think about intentionally crafting Chezie’s culture until about a year later. Around that time, my sister and I created our core values.
The approach was simple; we asked ourselves: "If we could design a company from scratch, how would we want to be able to describe that company?"
We created our lists separately, then came together to combine and refine them into our six core values:
🙌 Practice what we preach We can't sell a DEI software without being inclusive ourselves. Be transparent and put people first.
🤝 Take ownership Be accountable for what you work on and be open to supporting things you don't.
🛃 Focus on customer Keep the customer top-of-mind. Be willing to put their needs above your own desires or ideas.
🏎 Move fast with intention Have a bias to action, but don't be reckless. Target 60% of the information you need to make a decision, then make it.
🏋️ Be resilient Be open to giving and taking feedback, and be ready for pivots.
💼 Work ≠ life Like what you do, but separate work from life. Prioritize yourself so you can be your best when working.
These values gave us a concrete framework to refer to when deciding everything from product features to hiring to how we'd run meetings.
How You Can Do This
If you're starting and thinking about your company culture, here's what I'd recommend:
Start with what you value - Literally write down what's important to you in a workplace. Would you want to work somewhere that prioritizes speed over quality? Or individual brilliance over team cohesion? Be honest with yourself.
Think about the worst places you've worked - Sometimes, it's easier to identify what you don't want. What made those places terrible? Now flip those qualities to define what you do want.
Be aspirational but realistic - Your core values should be something to strive for, but don't set impossible standards to maintain at your company's stage.
Keep it simple - Aim for five or six that you can remember.
Revisit regularly - As I mentioned earlier, your culture must change. Set up time every six months to ask if your values still make sense for where your company is now.
One mistake many founders make is thinking culture happens on its own. But culture is what you deliberately create - otherwise, it happens by default. And trust me, the default isn't usually what you want.
Your core values become the foundation for how you make decisions, who you hire, and, ultimately, what kind of company you build. They're not just words on a wall - they're the principles you live by daily.
Lessons in Building Culture Since Launching Chezie
Looking back at the last few years building Chezie, I've learned some surprising lessons about company culture that don't always match what's in the startup playbooks.
Being Flexible - Your Culture Will Need to Change
One specific example comes to mind when I think about culture being flexible. A fellow founder had a similar value of "work ≠ life,” he hired an engineer who took that value too literally. What seemed like every two or three weeks, she would message the company’s Slack channel saying she didn't feel like working or was slightly under the weather and would take off.
I think about that story often because it helped me realize that what I meant by that core value of work not equaling life isn’t how we stated it. Today, that value means that when you're working, you should be working, and at our stage, you probably will be working long hours.
A typical day for me looks like being online from 9 to 6, taking a break from 6 to 8, and then getting back online from 8 to 9:30. That's about 10 hours – 20 more hours than what you'd call the typical 40-hour work week. But if I'm feeling burnt out, I'll log off early on a Friday, take a vacation, or work from somewhere new to change scenery.
That's what I mean by culture needs to be flexible. You might think you want to build a company in a certain way, but in the early stages especially, you must be realistic. The culture you envision might not align with what's necessary to reach your goals.
You Might Not Need a Culture (Yet)
I've realized that although our team has downsized to primarily contractors, we don't have a formal "culture." And that's okay.
Having a culture without a team outside of the co-founders is difficult. My sister and I have open communication; we take time off when needed, put our heads down when necessary, and take care of our customers. But it's not super formal because it doesn't need to be.
What's interesting as I think more about this is that as AI starts taking the place of positions you would typically hire for, we'll have to rethink what company culture even means.
I look at companies like Gumroad, founded by Sahil Lavingia. He published a manifesto about how he structures Gumroad, and now he has stated that he has no full-time employees. Gumroad has a culture, but it isn't the formally documented culture you'd expect from a startup with as much prominence.
Hire for Culture Just as Much as Skill
Regarding hiring and thinking about culture, I've learned that the decision has to be made just as much on how well candidates fit into your culture as their technical abilities.
With the engineer I mentioned above, that's one thing I didn't assess well enough. Since then, we've had the most success with people willing to get their hands dirty. That willingness to put in the work and be biased toward action is a skill that should be assessed, especially if you consider it part of your culture.
It isn't easy to assess this in an interview process, but I've found a few approaches that work:
Have the person talk about their approach to work.
Ask questions directly based on your core values.
Follow up with their references using those same questions (managers are usually more upfront in reference calls and can give you a better sense of what you're trying to evaluate).
Remember that skills can be taught, but alignment with your values and work style is much harder to change. In the early days especially, one who doesn't fit your culture can have an outsized negative impact on a small team.
The Bottom line
If you follow me on LinkedIn, you'll notice I don't write about company culture much. That's not because it isn't essential – it's because I haven't had extensive experience building one. We've never had more than four or five people on the Chezie team at any given time.
But that's precisely why I wanted to share these thoughts. Most founders are in the same boat – building small teams, figuring things out as they go, and realizing that the "perfect culture" looks different than what startup books describe.
As AI continues to change how we build companies, we must rethink what culture means. Maybe it's less about office perks and team retreats and more about the core principles that guide how you make decisions, treat customers, and work together – even if "together" means two co-founders and a handful of contractors.
What matters isn't whether you have an excellently documented culture deck or fancy values painted on your wall. What matters is building an environment where people can do their best work, even if that environment is just you and a co-founder grinding away in the early days.
Culture isn't something that happens – it's what you intentionally create. Without that intention, you end up with whatever happens by default. And trust me, the default isn't usually what you want.
So while I may not talk about culture often, I think about it constantly. Because ultimately, the culture you build is the company you'll have.
See you next week,
Toby