Don’t Be a Blackberry: Why Iteration Keeps Your Business Alive
Ever notice how some businesses skyrocket while others fade into obscurity? One minute, you’re the hottest thing on the market, and the next, nobody remembers your name. Just ask Blackberry.
Once the must-have business phone, Blackberry lost its grip when Apple and Android came along. The problem wasn’t a lack of talent or resources—it was a failure to adapt. That’s exactly what we’re talking about in this episode of The TrustBuilt Podcast with John Shrewsbury, co-founder of Gen Wealth Financial Advisors.
If you want to build a business that lasts, you’ve got to be willing to evolve. John shares why iteration—not reinvention—is the key to long-term success and how small, smart adjustments can keep your business thriving.
Adapt or Get Left Behind
John Shrewsbury’s career path proves that growth comes from pivoting, not standing still.
He started in radio—a notoriously tough industry with no guarantees—before transitioning into financial services, where he built Gen Wealth into a company managing over $1 billion in assets. That leap wasn’t about ditching one career for another; it was about paying attention to market shifts and adjusting accordingly.
"Comfort is the enemy of success," John says. "If you stop evolving, you start dying."
And that’s exactly what happened to Blackberry.
They owned the business phone market… until they didn’t. When Apple and Android disrupted the industry, Blackberry hesitated to change. Instead of adapting, they clung to what worked before—until it didn’t.
John’s advice? Never assume what works today will work tomorrow.
The Difference Between Iteration and Reinvention
A lot of business owners think that when things go wrong, they need to scrap everything and start over. But big wins don’t come from massive reinventions—they come from small, strategic tweaks.
John learned this lesson early from one of his mentors, Dan Arnold, at LPL Financial, who drilled into him the importance of iteration.
"Take your best path forward," John says. "If it works, great. If not, iterate again. The worst thing you can do is stop trying."
That’s the secret behind every successful business. Continuous improvement keeps you ahead of the curve, whether you’re adjusting your marketing, fine-tuning customer service, or tweaking your operations.
Keeping Your Team Engaged Through Change
Let’s be honest. Change freaks people out.
When you’re constantly tweaking and improving, it’s easy for your team to feel overwhelmed or disengaged. That’s why John focuses on hiring the right kind of people who embrace growth instead of resisting it.
At Gen Wealth, he looks for three key traits in every hire:
Hunger – The drive to grow, learn, and push forward.
Humility – Willingness to adapt and take feedback.
People skills – The ability to connect, build trust, and work as a team.
"If we hire well, coaching and motivation become a great experience," John explains. But that’s not all—keeping employees engaged means making them feel valued.
"You can’t treat people like cogs in a machine. If they feel like just another resource, they’ll mentally check out long before they physically leave."
Growth is Uncomfortable—But That’s the Point
What is the biggest lesson John wants entrepreneurs to take away?
Get comfortable being uncomfortable.
"The biggest wins in my career came from stepping outside my comfort zone," he says.
His own journey—from radio to finance—wasn’t exactly a straight line. It was full of calculated risks, smart pivots, and continuous adjustments.
His best advice? Slow down so you can speed up. Instead of chasing every shiny new idea, focus on making strategic, intentional changes that move your business forward.
The Blackberry Test: Is Your Business Stuck in the Past?
Want to know if your business is at risk of becoming irrelevant? Ask yourself this:
Are you changing with the times, or are you holding on to the past?
When was the last time you adjusted your strategy based on real customer feedback?
Are you iterating and improving, or are you running the same playbook from five years ago?
The businesses that thrive are the ones that are always looking ahead, testing new ideas, and refining what works.
So don’t be a Blackberry. Be an iPhone. Be an innovator. Be the business that keeps moving forward.
Listen to the Full Episode
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