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09 September 2025

In this Issue

🏖️    Comfort of Success
🥊    Never Waste a Crisis
🏗️    Whole Company Change
Break the routine of success to grow. More in today’s issue. | A24

🏖️  Comfort of Success

The dark side of success is it can make investing in growth harder and scarier.

We see this most often with business owners in their late fifties and sixties. They’ve worked hard on their business for a long time. They’ve made big yet calculated bets, and it has paid off. They’ve grown their business to a stage that affords them a pretty amazing lifestyle.

That success, coupled with what is a reasonably shorter time horizon, makes committing to the investments and changes for the next stage of growth even harder. The owner is looking at growth through the lens of maintaining and protecting what they have.

That tension of growing while protecting can become an inhibitor. Investments get made that go nowhere. There’s talk and plans to grow, but they get undermined by a leader unwilling to relinquish control or set the team up to follow through with the change that is necessary.

If that tension persists for too long, it can actually put the business at risk.

To keep growing at this stage of business requires a powerful “why.” The business owner or family, need to dig deep and ask, “Why do we want to grow to the next level?”

Make it personal. Make it tangible. Make it urgent. If you don’t have that why, the growth strategy will languish.

One Stat to Watch

52.3%

It’s the “silver tsunami.” 52.3% of businesses are owned by people who are at or near retirement age, 55 and older, according to a 2025 Gallup survey.

🥊  Never Waste a Crisis

Winston Churchill said, “Never waste a good crisis.” It’s sage advice to break out of a rut.

Growth strategy is a lot like dieting. People start a diet with good intentions, but after a while they’re like, “I love ice cream,” and they lose momentum. It’s not until there’s a major health crisis, like a heart attack, that the change sticks.

A shock to the system is a powerful catalyst for change. Fortunately, depending on how you choose to look at them, we’ve been experiencing once-in-a-generation events every other year.

Covid, for instance, was one of the greatest entrepreneurial events, because it was a catalyst for change.

At the start of the pandemic I saw a brilliant meme. It was a picture of a multiple choice question that asked, “Who led the digital transformation of your company?”

  1. CEO
  2. CTO
  3. COVID-19

COVID-19 was circled.

The meme captured a truth about what happened during the pandemic. Businesses moved faster than ever. Projects that used to take months or even years to complete were implemented in weeks.

That’s the power of a crisis. When your back is up against the wall, you can change.

The challenge is you don’t want to constantly be waiting for the next crisis to act. We’re not surfers waiting to catch the next wave. Instead, choose the change you want now and act like it’s a crisis.

You can manufacture the desire and behaviors to change without having a proverbial heart attack.

🏗️  Whole Company Change

Sales often takes the brunt of the blame and pressure when a business slows down. The focus becomes:

  • We need more customers…
  • We need more revenue…
  • We need more sales…

I don’t disagree. My dad always used to say, “Nothing relieves pressure like sales.”

But it also has to be stated that this isn’t purely a sales problem. It’s a whole company problem.

When revenue slips, it’s often a symptom of deeper issues:

  • Loss of brand relevance
  • Increased competition
  • Shifting customer expectations
  • Weakening product-market fit
  • Eroding profit margins
  • Delays in production and operations

Or a litany of other issues.

Sales will absolutely step up to the plate, and they have to. The first step in driving a turnaround is to dramatically increase the volume of sales activity.

At the same time, sales has to listen: Your customers will tell you what they want to buy. They may not say it with their words, but you will definitely hear and see it in their actions.

Responding to a market shift is a “Whole Company Change.” Sales starts the conversation, but operations, finance, support, and product all have to work together to rapidly adapt and shift to a new business reality.

🤔  Thoughts on Today’s Issue?

We’d love to hear your feedback. Message with any thoughts, comments, or ideas for future issues.

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