Your 250th-ish Reminder That Success Takes Time
Your 250th-ish Reminder That Success Takes Time
Entrepreneur Office Hours - Issue #250
You might have noticed this is the 250th issue of Entrepreneur Office Hours. I don’t know what it is about round numbers, but us humans really seem to love them. Because of that, I can’t help seeing this “250” milestone without wanting to take a moment to wax poetically about something. For all of your sakes, I’m going to try to make it something that’s important for you to know!
Let’s start by doing some math…
If this is the 250th issue of EOH, and if I’ve been posting once per week with an occasional stint of twice per week, it means I’ve been publishing this newsletter every week for something like four years.
Think about how long four years is. Sure, in the scope of human existence, it’s a tiny speck of time, but, in terms of a human lifetime, four years is the amount of time kids spend in high school or college. Four years is the length of a presidential term (and two congressional terms!). For years is longer than most TV shows last.
I mention this because four years, in the scope of a successful entrepreneurial venture, isn’t even the halfway point. And this is something lots of entrepreneurs forget.
We’re so used to “moving fast and breaking things” in the entrepreneurial world that we often forget the importance of putting progress in it’s proper temporal context. Just because we all want to be “successful” as quickly as possible, we also have to remember that successful outcomes aren’t magical. They require work, skill, and execution. All of those things take time. Lots and lots of time.
So, as you read this 250th issue, I want to take a moment to remind you that entrepreneurship isn’t a sprint. It's not even a marathon. It's more like an ultra-endurance event — a series of marathons strung together, each one requiring new strategies, new energy, and a constant willingness to keep going even when the finish line feels impossibly far away. The most successful entrepreneurs aren’t the ones who found success in a year or two, but the ones who had the patience to keep building, learning, and adapting over the long haul.
If this newsletter has taught me anything over the past four years, it’s that consistency is one of the most underrated skills in entrepreneurship. Not every issue has been groundbreaking. Not every idea has landed. But the act of showing up, week after week, learning, and continuing to engage, grow, and contribute is what moves the needle in the long term.
So, here's to 250 issues. And here's to you — whether you've been here from the beginning or just joined recently, I hope you're in it for the long haul, too. Because that’s what building something truly lasting is all about.
-Aaron
This week’s new articles…
Dear Entrepreneurs: Please Give Up On Your Dreams of Being CEOs
Forget the stories about successful founders leading companies to billion dollar exits — being CEO isn’t a job you actually want.
The Entrepreneurial Superpower Every Founder Needs to Develop as Soon as Possible
When you can get really good at this one thing, it completely changes your effectiveness as a leader.
Office Hours Q&A
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QUESTION:
Aaron -
I’m building a new software, and one of my co-founders (my technical cofounder) thinks it’s really important we make it multilingual from the start. He argues it’ll broaden our appeal to more markets, which, of course, will make us more money.
I’ve been reading your content for long enough to know how you feel about this. Clearly it’s not a good use of time or resources early on. Eventually, once we’ve got some good traction, sure. But not from Day 1.
My struggle is trying to convince him of this. How would you explain why it’s a bad idea to spend any time supporting multiple languages this early in our startup process?
- Anthony
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Yeah… navigating co-founder dynamics can definitely be tricky, especially when you’re both passionate about scaling but perhaps see different paths to get there. And, honestly, based on what you’ve shared, this is less a “right” versus “wrong” issue and more of a misconception about how startups fundamentally work, so convincing him to change his mind is going to be tricky. If I were to try it, I’d likely be focused less on telling him he shouldn’t do something and instead focus more on simply convincing him to hold off.
To do that, start by giving props to his vision: “I love that you’re thinking about scale and reaching as many people as possible right from the start. It’s ambitious, and that’s what we need.”
After that, gently steer the conversation to immediate priorities: “But let’s make sure we nail it with our initial users first. We need to get our core features so spot-on that adding languages later becomes a no-brainer because everyone will want what we’ve built.”
If you need help convincing him, a good analogy can also work wonders: “Think of it like building a house. You wouldn’t start painting the rooms before we’ve laid a solid foundation and put up the walls, right? Let’s get our foundation solid with our primary market, and then paint it with all the languages we want.”
Finally, as I mentioned, don’t make it a “no.” Make it a compromise that keeps his idea on the table: “How about this? We focus all our energy on getting things perfect with our first market. Once we hit [specific milestone], we take a day to look at our data and seriously talk about expanding languages. That way, it’s not off the table—it’s just timed right.”
This way, you’re not shooting down the idea but aligning it with your startup’s immediate needs and growth strategy. It shows you value his input and you’re on the same team, just pacing the features to match your resources and current market understanding.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!
