The importance of iteration for entrepreneurs

"Once I get to that point... everything will be better."

This is a little lie that I have told myself many times in business.

Once I get that salesperson hired.
Once our revenue hits $X per month.
If we could just reduce our churn to X%...

It's easy to imagine that at some point in the near future, everything is going to get easier or better. But that is rarely the case.

Instead, it's an iteration.

In this article, I'm going to share more on the value of iteration for entrepreneurs and how my failure to iterate impacted my own business.

The myth of that perfect moment

Earlier in my entrepreneurial career, I always felt like success was just around the corner. It was just one milestone away...

These days, I realize that's a giant myth.
At every level, there is a new set of challenges.
At that milestone, the challenge you were facing then may fade away, but it will be replaced by new challenges.

This is key to realize because otherwise you will drive yourself mad.

In business, there is no perfect state for your business. There are accomplishments. There are milestones. But it's never going to be perfect.

Perfect is destroyed by the market

Even if you get your business to this amazing perfect state... it won't stay there.
The reason is that markets shift and move.

For a period of time, I thought that Lead Cookie (opens in a new tab) was at this perfect state as a company. We were streamlined, operating, closing sales, driving leads... it was all great.

But the market is shifting.
LinkedIn is shifting.
More competitors are entering.

Even though Lead Cookie may have felt like the perfect company for a period of time, that perfection wasn't going to last. No company will last.

When you hit success, others will follow.
Markets will commoditize.
It's part of business and something you must accept.

When I started Content Allies, it was nothing like the B2B podcast production agency that it is today.

From Inc 500 to trying to stay alive

A few weeks ago, I had lunch with an entrepreneur. He built an amazing business in the photo printing industry in the early 2000s. His company was one of the first to market in printing photos on canvas style art prints.

They had an eCommerce store, insane margins, and even hit the Inc 500.

"My biggest mistake was thinking that was going to last forever."

He had a few years of insane profits... and then the market shifted.

Competitors entered the market.
The big players in the space started offering canvas prints.
And within a window of a few years, he went from Inc 500 to having to downsize the company and move to a new facility.

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Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.

Today, he's just trying to keep the business alive with long-term loyal customers while he works on building a new venture.

As we look back historically, it seems obvious that his market would commoditize.

Yet, as entrepreneurs, we often don't believe it could happen to us.

Iteration is key

So how do you combat this? How do you make sure you don't get commoditized? How do you not become the next "Blockbuster?"

In my mind, it comes down to consistent iteration.
It comes down to talking to your customers.
It comes down to staying on top of the industry trends.
It comes down to giving yourself space to see the big picture.
And it comes down to taking actions on a consistent basis to evolve your business.

There is no perfect state you will ever reach.
And, even if you get there, you still need to keep iterating, because the ground will shift beneath your feet.

And for those of us working in the industry of digital marketing... the ground moves fast.

When I started Lead Cookie in July of 2017, I could find 7 companies specializing in LinkedIn Lead Generation.
Today, there are hundreds, if not thousands, of competitors.

There are even people selling video courses on how to make money selling LinkedIn Lead Generation to your clients.

In the digital world, commoditization happens fast.

Iteration must be a constant activity

My biggest mistake with Lead Cookie was that I stopped iterating once I had hit "perfect." We reached a point where the service was working very well, and I froze.

I was afraid to change things because it was working. And for almost a year, we didn't make any updates or adjustments to the service.

The longer I waited to evolve the service, the scarier it became to do so. I reached a point where I became afraid that I would break what was working if I started to change things.

In reality, this was a giant obstacle in my own mind.

Today, we are consistently iterating on the service. We are expanding our service lines. Each quarter, we target building on a new "feature set" to our service line. We train team members and document processes around new services that we will offer.

We are constantly evolving and constantly iterating.

Iteration is not a one-time thing. It is something that must become part of your organization.

At my B2B podcast production agency (opens in a new tab), iteration has been central to the business. We started out as a LinkedIn content service, then grew to a blog writing service, and eventually pivoted to become a full service podcast agency. It was all an evolution.

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Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.

Don't stop growing or improving

When you hit success, you will want to stop. You will want to just coast with what is working.
Sure, give yourself a break when that time comes.
But don't stop growing or improving your service.

As soon as you stop the momentum of iteration, it becomes harder to start back up again.
So make it a habit.
Implement workshops into your company culture.

Keep growing. And keep iterating. It's essential to building a company that will last the test of time.

In a May 2025 conversation with Alex McClafferty (opens in a new tab), I described what happened to Lead Cookie's market: we got in early, when it was good, and then it became saturated as everyone started doing it. By then my focus had moved to Content Allies, which had become a podcast agency and was growing into wider B2B content and marketing work, and I had sold Lead Cookie to the people running it.