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We sit down with Zach Holman, one of the early engineers at GitHub, to explore his experiences and insights on scaling culture and the importance of shipping early.

Zach joined GitHub as the second engineer when the company had just nine employees and witnessed the development of its unique culture, which emphasized autonomy, ownership, and a friendly competitive spirit.

Throughout the conversation, Zach shares valuable lessons on being proactive when scaling a company, constantly evaluating processes, seeking feedback, and making adjustments before problems escalate. He emphasizes the significance of shipping early and often, embracing discomfort, and taking risks to seize opportunities.

Zach also discusses the challenges of bringing in outside talent, the value of a diverse team, and the common mistakes startups make when scaling their culture. Whether you're a founder, leader, or someone interested in the inner workings of successful startups, this interview provides a wealth of knowledge and inspiration on scaling culture and the power of shipping early.

GitHub's Early Shipping Culture

Ivan: You've had an impressive career, from being one of the first engineers at GitHub to your current ventures. Let's start with your time at GitHub and the unique shipping culture there.

Zach: Yeah, I joined GitHub very early on; I was the second engineer hired, and the company had around nine employees at the time, including the four founders. We had a strong shipping culture, and it's fascinating to look back on it now because it was so unique.

It's fun to look back at how aggressive we were with shipping, especially when we were sub-20 people. Engineers would disappear for a week or two, code like crazy, and then return with something amazing they had built. It was like a friendly competition to see who could ship the coolest features. This culture stemmed from everyone's exposure to open source, which fostered a sense of self-reliance and motivation to level up the codebase and add new features.

Why the Shipping Culture Worked

Ivan: What are your thoughts on why this worked so well at GitHub, especially in the early days?

Zach: I think a big part of it was the size of the team. When you're small, everyone can be involved in everything, and there's less hierarchy. As the company grew, maintaining that culture became more challenging. We had to start implementing processes and adding managers, which was a bit of a controversial shift internally. But it was necessary for scaling the company.

Maintaining the Shipping Culture with Growth

Ivan: As GitHub grew, how did you maintain that foundational shipping culture?

Zach: As the company got larger, the first step was to ship things internally to our own staff, which could be even more frightening than shipping to the general public. Getting people to actually use what you've built is the main goal. There's always code that's embarrassing, but you know it works (sort of), and you just want to get it into somebody's hands besides your own as soon as possible.

The Importance of Shipping Early

Ivan: Did you see this shipping culture often in other companies you advised or invested in later on?

Zach: There are certainly some companies that make you wonder how they're shipping so much stuff, which is always exciting to see. I think nowadays, with the way teams are structured, you often see the effectiveness of small, cross-functional teams of 2-3 people. In the early stages of a startup, it's best to avoid pre-optimizing for heavy hierarchy and instead focus on letting people split off and work on projects solo or in small groups.

One thing I want to emphasize is the importance of shipping early and often. I don't regret shipping things early at GitHub, but there were times when I wish I had shipped even earlier. It's better to get something out there and then iterate based on feedback and your own observations. That discomfort of putting something out there before it's "perfect" is a good thing because it forces you to prioritize and focus on what matters.

Common Challenges in Scaling Culture

Ivan: Were there any notable instances where not shipping early had a significant impact?

Zach: Well, one example is when we were considering launching a chat feature a couple of months before Slack came out. We were very close to launching it, but ultimately didn't. Looking back, I sometimes wonder what would have happened if we had just shipped it and seen what happened. It's a reminder that sometimes you just need to take that leap and put something out there, especially if it's an interesting and potentially valuable feature.

Common Challenges in Scaling Culture

Ivan: What are some common challenges or mistakes you see companies making when it comes to scaling their culture?

Zach: Everyone's making mistakes in their own unique way! But one common issue is reacting to problems instead of being proactive. Companies often wait until there's a crisis before making necessary changes. It's important to constantly evaluate your processes, get feedback from employees, and make adjustments before things reach a boiling point. Building a company is exhausting because you can never coast; you always have to improve and adapt.

Balancing Short-Term and Long-Term Thinking

Ivan: What advice would you give to startups trying to find the right balance between short-term and long-term thinking?

Zach: It's a tricky balance. You don't want to hire someone you'll only need four years from now, but you also don't want to hire someone who can only work for the next 3-6 months. There's an optimal middle ground. You need to be deliberate about where you are now and where you want to go. Constantly ask yourself what you're missing and what you can improve on. It's exhausting, but necessary.

Key Takeaways for Building a Strong Shipping Culture

Ivan: If you had to sum up the key takeaways for building a strong shipping culture, what would they be?

Zach: Building companies is really exhausting. You have to keep tweaking and improving as you go. When you don't actively think about how you are today and where you want to go in the future, that's when things start going off the rails. Unless you're consciously looking at this, getting feedback from your employees, and staying on top of it, you're going to have to deal with it one way or another - either ahead of time or months after you should have done something, which is much more painful for everybody. It's a really tricky problem, but it's essential to maintain a strong shipping culture and avoid the pitfalls of reactive decision-making.

Building a company is exhausting, requiring constant analysis, improvement, and proactive decision-making to avoid reactive chaos. Being mindful of the present and future, actively seeking feedback, and staying on top of processes are crucial to maintain growth and success.

Zach Holman

You can follow Zach on Twitter at https://twitter.com/holman to learn more about his insights on scaling culture and shipping early.

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