Here are my favorite non-obvious paradoxes that startup founders face as their companies grow and they want to keep winning.
1) You experiment wide to start; you narrow in to grow up.
Focus to Grow.
The game changes from the required experimentation and saying Yes when starting and surviving.
Growth and acceleration don’t come from doing more of everything; they come from saying No more often and being great at fewer things.
Focus on the 10% of customers, features, GTM tactics, employees, and marketing messages that give you amazing leverage and results.
2) When you start, you do everything as a founder; you delegate most of those day-to-day tasks when you grow.
Being the CEO of a $10M ARR software company is a different sport than being the founder of a $1M ARR software startup.
Both require real athletes, but the rules and tools change completely.
3) Your major goal of selling your company for a big prize doesn’t make you happy by itself.
You habituated the hard work, teamwork, daily struggle, overcoming crises, progress, impact, and the change you created. And all that clapping and cheering.
Most post-exit founders with big bank accounts would trade most of that to have an exciting challenge again, and many do.
4) You grow your company, team, system, products, and market. They don’t end up where they started, but neither do you.
You have to change your thinking, give up some old habits and beliefs, and sort out what doesn’t work anymore.
Founders end up in different places as their companies grow. If the founders don’t change, the company won’t either.
Most founders are surprised by this.
5) Many technical and product-oriented founders start out building a “platform” they think will work for everyone for all kinds of use cases. But a product is not a business.
Your customers require you to be known as the best at something important for someone specific—the best at what they need right now.
That’s the opposite of where most founders start.
6) Big outside funding doesn’t make life easier or reduce risks. It adds a layer of overhead to your business to raise funds, play the funding game, and pay back investors.
Risks go up with funding when you need to sell your company for 3X more and faster, or you won’t win any prize at all. Big VC funding usually doesn’t work (for founders), and it’s far less common than it appears.
7) When you have more than 50 or 75 employees, CEOs often spend most of their time on internal stuff, such as employees, investors, processes, planning, and communication.
It isn’t just about selling the next customer and getting stuff done like you did when there were 10 of you.
Those are a few contradictions that startup founders learn and understand if they grow their companies above $10M ARR.
The first rule of the game is to know what game you are playing.
The game changes as your business grows.
What other non-obvious paradoxes do you see between startup and scale-up?
