Having worked with highly successful entrepreneurs, consulted for well-funded start-ups, invested in private ventures, and bootstrapped two thriving companies of my own, I’ve had a front-row seat to everything from 9-figure exits to complete demise. Through these experiences, I’ve learned what it takes to build a sustainable company—and how great ideas can crash and burn.
Last month, I had a conversation with one of our newer team members to recognize his impact and check in on how things were going from his perspective. He shared how his new role on the Rivvit team was unlike anything he’d experienced before. He thanked me for the autonomy he’d been given (and rightfully earned!) and shared how rewarding it was to work with a small team of A-players executing on a single, shared vision.
As a leader responsible for defining the firm’s strategy and vision, I couldn’t help but take this as a compliment. Having worked in chaotic environments throughout my career, I know that every team member has a choice about where and with whom they work. His feedback reinforced my leadership style, which is shaped by lessons from both incredible mentors and less-than-stellar managers.
Reflecting on this conversation, I began to think about the major factors that I believe lead to success and failure. Here are some lessons I’ve learned along the way.
“Paint the target. Don’t shoot the arrow.”
This is one of my favorite quotes from a mentor I deeply admire. Strong leadership is the cornerstone of any successful business. A clear vision serves as a North Star, guiding both the company and its people. This advice reminds me to focus on defining a clear vision and letting my team chart the best path to achieve it. Leadership isn’t about micromanaging—it’s about empowering your team and enabling success.
As a hands-on leader, I come with strong opinions about how things could be done, but I’m just one voice. Investing in top-tier talent and then stifling their creativity would be counterproductive. Striking a balance builds trust and fosters a collaborative culture.
“Know what you don’t know.”
“And build teams around you to fill the gaps,” a group executive told me in 2007 as he promoted me into a role I had doubts I could handle. That advice has shaped my perspective on leadership and team-building. It taught me the power of diverse skill sets—you don’t need to be the best at everything. Recognizing your limitations and surrounding yourself with complementary talent is a strength, not a weakness.
Trust is everything
Entrepreneurship is about building relationships. Clients value honesty, even when the truth isn’t what they want to hear. Transparency and realistic expectations build long-term trust and loyalty. Over the years, this approach has helped my businesses earn and retain lasting client relationships.
Leverage your network
“Don’t burn bridges” is timeless advice, but an even better approach is to pay it forward. I cannot count the number of small favors I’ve done for others without expecting anything in return. Time and time again, those same people have reached out with opportunities, introductions, or collaborations when I least expected it.
Your network isn’t just a list of contacts—it’s a source of mentorship, opportunities, and support when you need it most. Whether it’s learning from seasoned professionals or gaining access to potential partners, nurturing relationships—both personal and professional—can be a game-changer in entrepreneurship.
Play the long game
Successful entrepreneurs prioritize sustainable growth over quick wins. I’ve seen companies fail by focusing solely on immediate results. Playing the long game and delivering incremental value is crucial for building something enduring. Short-term sacrifices often pave the way for long-term success.
Gather feedback and solve real problems
Focusing on specific use cases and solving real problems is one of the most impactful strategies in entrepreneurship. It’s easy to speculate about what customers might want, but the best insights come from gathering direct feedback. Constantly listening to clients and prospects ensures that your solutions stay relevant and valuable.
Learn from failures: what not to do
Failures teach lessons that success cannot. Having seen two companies crumble firsthand, I’ve noticed recurring patterns to avoid:
- Shifting priorities and lack of focus. Constantly changing direction or trying to be everything to everyone creates confusion, hinders execution, and dilutes your strengths. Success comes from consistency, clarity, and specializing in what sets you apart.
- Dictator-style leadership. CEOs who stay disconnected from day-to-day realities while making unilateral decisions risk alienating their teams and undermining progress. Leadership requires humility and collaboration.
- Swinging for the fences. Chasing grand slams instead of building momentum through smaller, consistent successes can derail progress. Steady singles and doubles lay the foundation for sustainable growth.
- Mismanaging external funding. Raising outside money can be a major accelerator, but spending it without strategic discipline can quickly lead to financial instability. Treat every dollar as if it were your own.
- Scaling without strategy. Hiring too quickly or bringing on the wrong talent can lead to inefficiencies and dilute team performance. A lean, highly skilled team will always outperform a larger, misaligned one.
Stay grounded
Entrepreneurship is an emotional journey. It’s important not to get too high on the ups or too low on the downs. Staying grounded not only keeps you connected to the business but ensures your team feels supported, even during challenges. Joining daily meetings, participating in client delivery, and rolling up your sleeves when needed sets the tone for the entire team.
Closing thoughts
Being an entrepreneur means constantly learning, adapting, and growing. It’s about taking calculated risks, staying focused on your vision, and building something lasting. Whether you’re just starting out or refining your approach, the most valuable lessons often come from failure, and the most enduring success comes from focusing on people, trust, and long-term impact.