Lessons from 15 Years of Entrepreneurship
As an entrepreneur with 15 years of experience and three agencies under my belt, I’ve learned one essential truth: success isn’t about working harder or chasing every garish opportunity. It’s about reverse-engineering your goals, breaking them into actionable milestones, and staying grounded in principles that guide your journey.
Let me paint a scenario. Imagine you’re in a sailboat, docked in New York Harbor, preparing to set sail for Ireland. Your North Star—the ultimate goal—is to reach Ireland safely within one month.
But how do you get there?F
You don’t just point the bow east and hope for the best. Instead, you split the journey into manageable daily and weekly mile markers. With a clear map and the right resources, you’re ready to face the open sea, staying focused on the path that will get you to your destination.
Learning Through Mistakes
Here’s the thing: as a founder and entrepreneur, you’re going to make mistakes—it’s unavoidable. But what I’ve come to realize is that those mistakes aren’t just bumps in the road; they’re opportunities.
If you take the time to document them, understand what went wrong, and make sure you don’t repeat them, they can become the pillars for better decisions in the future. For me, this process of reflecting and refining has been transformative. It’s shaped how I lead, how I approach decisions, and how I’ve built the culture in my businesses.
At Get Levrg, we’ve outlined values to empower our team to inform how they should make objective decisions, and how they should think and act and respond to customers.
Two cornerstones stand out:
1️⃣Ownership of Decisions
Team members are the first line of defense in solving problems. Whether it’s a customer issue or a project challenge, ownership means taking responsibility, making decisions, and not relying on the founders for every response. If there’s an issue, employees are the first line of defense. They have to own it, take action, and trust their ability to handle it.
2️⃣Radical Transparency
There’s no such thing as over-communicating. Internally and externally, no detail is too small to share. Whether it’s with team members, customers, vendors, or investors, keeping everyone in the loop fosters trust and ensures alignment.
These principles have been game-changers for us, creating a culture where people are empowered to take charge while staying connected to the bigger picture.
First Principles
Beyond values, every business needs first principles—those unbreakable rules that serve as the foundation for how you operate. For us, these principles dictate everything: how we approach our business model, go-to-market strategy, revenue generation, and customer service. Your first principles are non-negotiable, and sticking to them is the key to sustainable growth.
Let me share a lesson I learned the hard way
At my first agency, Sales for Life, we landed six-figure deals but bent on payment terms, offering flexibility like quarterly or semi-annual payments. It seemed harmless at first, but delayed payments led to massive accounts receivable issues and a cash flow crunch that nearly choked the business.
Determined to avoid the same mistake, I implemented credit card payments for recurring revenue at my second agency, Pipeline Signals. While this created predictable cash flow, I compromised again by allowing some customers to use invoices instead.
The result? Chaos. Credit card customers paid on time, but invoiced clients delayed or defaulted, putting 50% of our revenue at risk.
These experiences taught me a crucial lesson: compromising on core principles eventually creates cracks that can break your business.
The Transition
By the time I launched Get Levrg, I had learned my lesson. I knew one thing for certain: bending on payment terms had cost me in the past, and it must not happen again. Payment terms became a first principle—a non-negotiable. Every customer pays by credit card. No exceptions.
The impact was immediate and undeniable. From day one, we’ve been profitable. Cash flow issues? Completely eliminated. That single, unwavering rule has given us the stability and predictability to scale without distraction, allowing us to focus entirely on delivering value to our customers.
Here’s the thing: as entrepreneurs, it’s easy to feel the pressure to bend your principles—to make exceptions for short-term wins or to keep clients happy. I’ve been there, and I’ve learned the hard way—flexibility in the wrong areas can lead to fragility. When you compromise on your first principles, cracks start to form, and over time, those cracks can break your business.
Mistakes are inevitable, but they’re also invaluable if you take the time to learn from them.
Reflect, document, and use those lessons as building blocks to create a stronger, more resilient foundation for your business.
