When you’re an entrepreneur, you don’t just build a business once. You build your business over and over again as you grow. 

Every time your company enters a new growth stage, there are new lessons to learn. Some are harder than others—usually because you’re more hard-headed about learning them (speaking from experience).

The point is: as much as you would like to build your $100 million business now, you first have to build your $10 million business and even your $1 million business.

The way you grow is by iterating quickly. That’s why iteration is an entrepreneur’s best friend.

How to Iterate in Business

To iterate is “to create something by building on previous versions . . . using each version as the point of departure for refinements and tweaks.” 

Can iterating sometimes feel like deja vu? Sure. But the key is in the “building on previous versions” piece. We aren’t talking about solving the same problems over and over again in your company (that signifies a process problem, btw). 

We’re talking about tackling similar challenges, but each time, being a little wiser and a little further along the path of growing your company.

Where does iteration show up in your company? Let’s look at four key areas (they happen to be our four GROWTH quadrants)


When you think about your organization, you might imagine a team of hundreds of people. Executive assistants and middle management layers abound, all supported by a big company with healthy revenue.

But today, your organization is probably much scrappier. You might have employees sitting in multiple seats. Maybe you own sales and act as the company Visionary. That’s where you are now.

It’s not a straight line between your org chart today and the one you imagine for the future. You scale up in stages, not all at once (Plus, can you imagine onboarding that many team members at the same time?!). That evolution is iteration.

And the people you put in those seats will iterate too. Your dream team of executives may not give you a second look today—but two years from now they might. Two years from now, you might be able to afford them, too. 

In the meantime, you’ll be constantly balancing talent and budget, hiring the best possible people you can afford. And you’ll keep ratcheting those standards up over time.


The more people you have, the more complexity they bring. Process is what standardizes the way your company runs. It ensures that everyone has clear benchmarks and standards to live up to. Today’s simple SOP might iterate into a full-blown manual or video training in the future. 

What you sell may be iterative as well. The easiest example to think about is SaaS platforms, which are constantly releasing new versions of their products. As you incorporate new technology, better systems, or even pivot your offerings, what you’re selling—and what you’re not selling—gets clearer and more refined.

Directly tied into what you sell is who you serve. When your business is smaller, you’ll usually sell just about anything to just about anyone. But over time, you’ll build your reputation. You’ll sharpen your focus, and your offering will become more productized [link to put it in a box post]. Clients who aren’t a great fit will naturally get crowded out by dream clients who are a perfect match for what you’re selling.


This area is all about refinement and sophistication. If you have no financial reporting whatsoever, you get better by reviewing your P&L each month. Then maybe you add cash flow. You build an annual budget, then a 3 year budget.

Eventually, you’ll track metrics like customer churn and lifetime value. But if you bite off more than you can chew at first, you may end up doing nothing at all.


Thinking and acting strategically are definitely skills acquired over time.

For example, we help companies articulate their value proposition (Why Us?) during the first 90 days of our work together. That’s to establish a baseline. From there, you can and should tweak, refine, and update your value prop continually. 

And how about growth strategies? There’s so much to be done, right? Yes, it would be great to double your ad spend AND look into acquisitions AND grow your email list AND revise your pricing AND AND AND. 

You can do those things. You will do those things. But if you try to do all those things at once, you’ll either run out of money, lose your mind, or both.

Personal Iteration for Entrepreneurs

As an entrepreneur, the iteration you need to be most prepared for is your own. None of us have it all figured out (a fact I am much more willing to acknowledge now than I was in my 20s). 

In fact, anticipating failure in iteration can help you ultimately succeed. Being comfortable getting it wrong or falling short gives you the courage to take more swings at bat. And that leads to greater odds of success.

When you iterate, expect that the next version will be better—but never perfect. 

With the right support, you’ll keep getting stronger, and wiser, and better at being a business owner. You’ll continue to evolve and grow. Not being at the endpoint today isn’t an obstacle—it’s the point of the journey. 

I sincerely hope that you enjoy the ride. 

If you’ve identified an opportunity to iterate in your business and need some guidance, let’s talk. Our consulting team is standing by to help.