How to Maintain a Strong Culture While Your Startup Grows

Whenever a startup finds success and starts to grow, there are going to be changes and challenges. One of the biggest challenges is maintaining a strong culture. After all, it’s always easier for a founder to build the right culture and put their stamp on a company when it’s only 10 people. It’s another thing when it’s grown to 50 or more people.

In my countless interviews with startup founders, most of them talked about the importance of establishing values and building a strong culture. Many of them put a lot of time and energy into establishing the right values so that they could build a strong culture. It also remained a point of emphasis while the company was growing. After all of my talks with founders, I was able to pinpoint three keys to maintaining a strong culture while your startup grows.

The first key is to always hire based on your values. Obviously, you should be doing this from the start, because if you do, things will be much easier when you grow. Andrew Bruce, the founder of Data Gumbo, explained to me that one of his startup’s values was to “be comfortable with chaos.” By only hiring people he believed were comfortable with chaos, he was a step ahead when things began to change.

The second key is to avoid becoming outcome-oriented. This may feel a little counterintuitive for some founders. After all, if the end result is positive, the method must have been flawless, right? But that’s not exactly how it works. The three-person founder team at CodeCov told me: “A bad outcome with the right decision-making principles, in our estimation, is better than a good outcome via a bad decision.” They understand that by staying true to themselves and true to their process, they can build a strong culture, even if the results aren’t always ideal.

Last but not least, it’s important to recognize that values may need to change with time. Andrew Bruce of Data Gumbo told me about his team reviewing their values regularly to see if they’re still relevant. After all, the values that a startup grew up with may not be what that business needs after reaching a certain level of success. By sticking to those same values for too long if they no longer make sense, a company’s culture is bound to suffer.

Of course, there is a profound level of complexity when it comes to a company’s culture. It’s why founders need to devote time and attention to building the right culture. It’s also why Niels Martin Brochner of ContractBook once told me that cultures are a living thing.

Since the culture within the business is a living thing, you must take steps to make sure it remains strong while your startup grows. As you decide how to maintain a strong culture, always consider the advice from founders who have been in your shoes before.

Before I founded the Midstage Institute, I spent years helping high-growth startups navigate the complex journey of scaling. I’ve worked with more than 50 companies as they moved through the midstage, including over 10 that became unicorns. In that time, I’ve seen how easily momentum can slip after passing $1M ARR. Execution gets harder, team alignment starts to fade, and what used to work suddenly doesn’t.

In a free 30-minute Breakthrough Call, I’ll help you uncover the real issue that’s slowing things down. Whether the root cause is structure, accountability, or strategy, you’ll walk away with one or two clear next steps that can shift your trajectory. There’s no preparation needed and no sales pitch—just a straightforward, founder-to-founder conversation focused on getting you unstuck.

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