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Key Takeaways
- Personal connection and being present in day-to-day operations build trust and strong company culture.
- Continuous innovation and industry education are essential for long-term success and positioning as experts in the field.
I was recently a guest on a podcast where the host asked me a deceptively simple question: “How have your core values shifted over your career as an entrepreneur?” I’ve been thinking about it ever since. Should our core values really change? They might evolve or expand as our businesses grow and we gain experience, but our fundamental values shouldn’t disappear with each pivot. After all, they define who we are and why we do what we do as entrepreneurs.
After reflecting on two decades of building and growing a business, I’ve found that while my company has certainly transformed and adapted over time, the values guiding my decisions have remained remarkably consistent. These five core principles have served as my North Star from day one.
Related: Unlock the Secret to Crafting Compelling Core Values With This Step-by-Step Guide
Personal connection
Time and time again, I’ve watched businesses stumble when leadership is absent — quality slips, culture dissolves and customers start to walk away. In my experience, being present and engaged has had the greatest impact on my company and has been absolutely critical to my ability to lead effectively. It’s not enough to set a vision and step back; the leaders who can truly immerse themselves in the day-to-day realities of a business — listening to employees, connecting with clients and observing operational challenges — build stronger teams and create businesses that thrive over the long term.
Personally, I practice this core value both internally with employees and externally with clients. Whether I’m setting aside time for weekly lunches with my team (no shop talk allowed) or jumping on the phone myself to talk to a client about a new feature request, these meaningful moments of connection build trust, strengthen relationships and reinforce the culture of our company. Maintaining a personal connection to my business, my team and my customers ensures that our team feels supported, our clients feel heard and our business continues to evolve.
Exceptional service
Our biggest differentiator in the software space isn’t the size of our company or the scope of our budget — it’s how we show up for our customers and deliver, every single day. Earlier in my career, I worked my way up the ladder of an internet service provider (ISP), and I watched the owner of that business outsource as many employees overseas as possible to cut costs. I saw employee morale start to plummet, and the vibrant, close-knit culture we had worked so hard to build disappeared as our in-house team got smaller by the day.
While I value my time at the ISP, this experience has always stayed with me. When I founded my own company, I made and continue to make very intentional decisions to do things differently. Ever since I hired my first employee, I’ve committed to keeping our customer service entirely in-house and in-office — a decision that remains true today, almost twenty years later. Not only has this allowed us to build a culture that often feels more like a family than a workplace, but it’s also allowed us to maintain full control and ownership over the quality of service our customers receive. We’re able to stay close to the people we serve, ensuring that feedback is not only heard and valued, but acted on. At our company, service isn’t just a department — it’s a philosophy that guides everything we do.
Related: Core Values: What They Are, Why They’re Important, and How to Implement Them Today
Organic growth
When companies answer to a board of directors, decisions ultimately revolve around satisfying investors — often prioritizing growth and profit at the expense of customers, employees or even the product itself. I’ve experienced this myself in the past and seen it damage others in our industry, which is why I’ve always valued maintaining independent ownership and avoiding outside investment. I’ve turned down hundreds of offers so I can control our focus — which continues to be the happiness of our customers and our employees. Our growth may not have been as explosive as other startups, but we’re still going strong after almost two decades in business — so the formula seems to be working.
Continuous innovation
In the software world, standing still is the fastest way to fall behind. Our customers’ needs are constantly evolving, and the technology that supports them needs to keep pace. Innovation has always been at the core of our business — not by chasing every new trend, but by continuously improving the tools and value our customers rely on to do their jobs.
Many of our most impactful features and enhancements have come directly from customer feedback or ideas sparked in casual team conversations. I still make time to review feature requests and support tickets myself, because I believe that innovation starts with real challenges that deserve thoughtful solutions. For us, innovation isn’t always about being first to market — it’s about being the most responsive, adaptable and committed to delivering lasting value to our customers.
Related: How to Keep Your Team’s Core Values Intact While Scaling Fast — or Risk Your Business Failing
Industry education
At our company, we invest heavily in industry education, both internally and externally. Internally, that means keeping our team knowledgeable and up-to-date, whether it’s technical training in our software platform, customer service skills or the latest property management best practices. Externally, I’m passionate about sharing that expertise with our customers and beyond. Our team spends thousands of hours each year building blog posts, webinars, guides and tutorials that we share for free with anyone in the industry. By empowering others with information, we help elevate the entire industry while also driving impact for our customers. A bonus — this commitment to education has become one of our strongest marketing tools, reaching millions of people every year and positioning our team as experts in our field.
These five core values have been my guiding compass for almost 20 years, and they continue to shape how I lead and how our team operates every day. Staying steadfastly true to them has allowed our business to grow sustainably, adapt thoughtfully and make a lasting impact that extends far beyond our bottom line.
Key Takeaways
- Personal connection and being present in day-to-day operations build trust and strong company culture.
- Continuous innovation and industry education are essential for long-term success and positioning as experts in the field.
I was recently a guest on a podcast where the host asked me a deceptively simple question: “How have your core values shifted over your career as an entrepreneur?” I’ve been thinking about it ever since. Should our core values really change? They might evolve or expand as our businesses grow and we gain experience, but our fundamental values shouldn’t disappear with each pivot. After all, they define who we are and why we do what we do as entrepreneurs.
After reflecting on two decades of building and growing a business, I’ve found that while my company has certainly transformed and adapted over time, the values guiding my decisions have remained remarkably consistent. These five core principles have served as my North Star from day one.
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