Principles for Lasting Success: Lessons from 30 Years as a Tech Entrepreneur
Over the last 30 years, I’ve had the opportunity to help build two technology companies from the ground up — Evolving Solutions and Keyva. Along the way, we’ve experienced plenty of wins, made our share of mistakes, and learned a lot in the process.
With that in mind, I’d like to share some of the most important lessons learned from my years of creating and running two successful tech companies and provide my perspective on what every entrepreneur should know to build a business that can stand the test of time.
Defining Moments That Shaped My Business Approach
Two pivotal experiences in the months before launching my company fundamentally shaped my entrepreneurial journey.
First was a meeting with SCORE (Senior Corps of Retired Executives), a volunteer advisory group for new entrepreneurs. My experience with SCORE was incredibly valuable, but in one case, I am glad that I trusted my gut. While reviewing my business plan worksheet that asked for our key business differentiator, an advisor said, “By the way, your differentiator can’t be your people, everyone has people.” This rocked my world since a key element of our model centered on hiring the best technologists in the industry within their respective field. Somewhat daunted, I continued to focus on people as a differentiator, and I’m glad I did. The experience taught me a couple of things: First, every business is different and has its own unique differentiators. Second, listen to experts, but business owners need to make their own decisions from their head, heart, and gut.
The second defining moment came when seeking financing. The bankers reviewed my business plan and expressed support of it, so they approved the financing with one condition. I had to deposit the same amount that I was requesting into my business account. While that was hard to get excited about, I did it because it was about making a personal investment in my business.
Good banking relationships are essential to entrepreneurs. But this experience taught me to build my own financial reserves and not be dependent on a financial institution. This principle has enabled us to weather numerous economic storms and to provide strategic financial offerings to the benefit of our clients.
Avoiding Common Tech Entrepreneurship Pitfalls
Entrepreneurs are often drawn to what’s new and exciting, and I’ve been no exception. About 10-15 years into building Evolving Solutions, we made a bet on cloud and managed services, which were both emerging areas at the time. In hindsight, we didn’t lay the right foundation. We moved too quickly without doing the deep planning, hiring, and strategic alignment that the situation required. We had to make some tough decisions and step away from some of those investments. And, while I’m glad that we did, I wish we had done it sooner. The lesson was that when you are exploring new areas, be deliberate and do the necessary due diligence up front. And if things don’t go as planned, be honest with yourself — make the call and move forward with what you have learned.
The experience taught me the importance of focus. I’ve come to think of our business in terms of concentric circles. The center circle represents our core strengths where we know we can consistently deliver value. As we move outward, we move into less familiar territory and risk grows. It’s tempting to chase opportunities in the outer circles, especially when others are finding success there. But I’ve found long-term success comes from staying close to where your expertise, people, and values align.
Essential Mindsets for Entrepreneurial Longevity
Maintain a Healthy Perspective
The entrepreneurial journey can seem like a roller coaster. The ups can be exhilarating. The downs can hit hard. But riding your entrepreneurial journey in this manner isn’t a recipe for success. I’ve adopted a mindset that’s served me well: Things are rarely as bad as they seem and they’re never quite as perfect as they appear either.
In 30 years of building a business, I’ve faced some challenges that felt overwhelming in the moment but seem small in hindsight. I’ve learned to operate within an emotional range — to stay steady during the wins and centered during setbacks. This doesn’t eliminate stress — there is no shortage of that when you are leading a growing company — but it helps keep things in perspective and leads to better decisions.
Develop Core Values and Stick with Them
One of the most important realizations I came to — later than I would have liked — is the value of identifying and committing to authentic core values as early as possible, and staying true to them. I’m not talking about feel-good statements you hang on a wall, but genuine principles that guide how you build your culture, make decisions, and lead your team.
In a previous blog, I discussed how foundational our core values have become at Evolving Solutions and Keyva. Looking back, I wish we had formalized them earlier. They would have helped us avoid some missteps and made hiring decisions more straightforward. When your values are clear, they act as a guide that provides direction at every stage of growth.
Balance Innovation with Consistency
Innovation must be intentional, not reactive. The sooner you develop and commit to a clear innovation approach, the faster it becomes integrated into how you plan, prioritize, and grow. For us, that means using a structured innovation process called the Business Evaluation Approach (BEA). It gives us a consistent lens to evaluate new opportunities and decide where to invest our time, energy, and capital. It doesn’t limit creativity, it focuses it, so we invest in the areas where we can truly differentiate and succeed.
I received a piece of advice years ago that I’ve never forgotten: “Just because you’ve been successful in what you’ve done thus far, don’t think for a second that you have the Midas touch where everything you touch turns to gold.” That reminder has helped us avoid countless missteps over the years, and it is something I think every entrepreneur should keep in mind.
For tech entrepreneurs just starting out, I often recommend taking a Goldilocks approach. Identify what you’re good at, understand the market and competition, and don’t get pulled to extremes. Oversaturated markets or unfamiliar areas may look exciting, but they can drain your focus and resources quickly. Stay focused on your core strengths.
Final Thoughts
Our companies have reached a point where momentum is on our side. We’re financially sound and we regularly compete and win against companies many times our size to deliver solutions to the most complex global clients. At a recent meeting, one of our partners shared their admiration for what we’ve built. This external validation reinforces something I’ve believed all along: When you stay focused on your core strengths and strategically expand, real growth, and success follow.
If I could sum it up with a few guiding principles, they would be: Stay focused on your core strengths, maintain financial independence, define and live your values, and approach innovation strategically. Most importantly, trust your instincts — they’ll be your best guide.
Building a business that lasts isn’t easy, but for those with the passion and perseverance to see it through, there’s nothing more rewarding than creating something that stands the test of time.
