Member-only story
Leadership
What Keeps Founders Up at Night
The most dangerous threats to your business are the hardest to share, and often, no one else gets the full picture until it’s too late.
When you’re a founder, your mind never fully switches off. From the day you form your company, you’re in a fight to survive and you’ll have many sleepless nights.
In this article, I’m going to share some of the most common dilemmas that founders face when they’re building a successful startup. There are no easy answers to these existential questions, but if they’re keeping you awake at night, believe me, you’re not alone.
Pre-seed stage dilemmas — less than $500k raised
They say that taking the first step is the hardest part. But once you’re a few months in, you realise that the hardest parts of building a company are always yet to come.
1. How do I clearly describe what my startup does?
Somehow, it was easier to describe your big idea before you started working on it. But now, people are impatient to learn about what you do, and summing it up in a sentence or two is hard. When people give you confused looks and offer ever more conflicting advice, you start to doubt whether this was a good idea after all.
2. Should I take on a co-founder?
Common wisdom says that starting a business is too hard for most mere mortals and co-founding teams have an edge over sole-founders. But taking on a co-founder is a heavy decision. Our brains are wired to focus on what we might lose: control, ownership, credit. What happens if it all goes wrong?
3. Are we ready to launch yet?
As you build your early product, you’re overwhelmed with possibilities. Despite pizza-fueled all-nighters, launch date has come and gone and you realise that if you can’t get something out there, you’ll never learn from real customers. Perfectionism may have worked in college, but now it’s stopping you from getting stuff done.
