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Less Annoying CRM's Tyler King on hitting $3 million ARR and reevaluating his ambitions

🤓 Read this if: You've wondered what you'll do when faced with a choice between your values and profit.

✅ Key Takeaway: As your business grows, you'll probably face situations that challenge your values. Your decisions will set the tone for your company. They may also determine how satisfied you feel with your work a decade in. Choose carefully and remember why you're doing what you're doing.


@tilikang of Less Annoying CRM hits $3 million ARR 11 years in, and he's thrilled about that. But his younger self might not have been so excited. Here's how he reset his expectations of unicornhood and found contentment in having a really solid small business.

It's funny, because depending on how far back I look, this milestone would either be really exciting or sort of disappointing.

In the very early days, just being able to work for myself and pay my bills would have been more than enough. So in that sense, it's surreal to be at $3 million in annual recurring revenue.

But as soon as we started finding traction, my ambitions got much bigger. Too big, actually. We had a couple of years of 5 to 10x growth. That's easy when you're really small, but I was naïve enough to think we were on pace to be a unicorn one day. If you'd told me then that we'd be at $3 million 11 years into the business, I'd have considered it a failure.

Eventually, reality set in.

What Changed

Our growth rate slowed. I wasn't willing to raise money, so we didn't have any growth capital. Our customer service costs were too high. I'd imposed restrictions against spamming and other shady marketing tactics. Each of these decisions was an anchor keeping us from hockey stick growth.

But we decided to stick to our guns and keep doing what we loved, even if it meant lowering our financial ambitions.

The Impact

We lost a couple of people because they signed up for a bigger opportunity. That hurt. One of the few things I'd do differently if I could is set more realistic expectations with the early employees.

Since making that decision, I've been able to appreciate our trajectory for what it is. We fit better as a healthy small business.

The Moral

And I think too many people think the only way to be ambitious is to try to get as rich as possible. There are other forms of ambition. It's okay to be satisfied with modest growth and channel your energy into other things — like the impact you have on customers, employees, and your community.

So yeah, I'm thrilled to reach $3 million ARR, and I realize how lucky I am. But unlike the early days, I'm not desperately fixated on the next revenue milestone. I'd rather focus on other things because I know the revenue will follow in due time.

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