The Toughest Lessons I Learned as a Founder
An engineer, entrepreneur, and teacher reflects on what he got wrong, why it mattered, and what he would do differently if he had the chance.
Starting a company was a dream come true. Like many first-time founders, I was driven by passion and the desire to build something meaningful. But the startup journey quickly proved more complicated, more humbling, and more emotionally intense than I ever imagined. Along the way, I made several painful mistakes—some obvious only in hindsight—that cost me time, energy, relationships, and money.
Entrepreneurship is often glamorized as a fast-track to freedom, wealth, or recognition. But as NVIDIA founder Jensen Huang bluntly said in a 2024 interview:
“If we had realized the pain, the suffering, and how vulnerable you feel while enduring challenges—the embarrassment, the shame, and all the things that go wrong—I don’t think anyone would start a company. Nobody in their right mind would do it.”
That quote stuck with me. It validated the emotional rollercoaster I had lived through—and what I’ve come to understand is that these mistakes weren’t just setbacks. They were lessons. In this article, I reflect on some of the hardest parts of my founder journey: what I got wrong, why it mattered, and what I would do differently if I had the chance. Each section begins with a real mistake I made, followed by suggestions for others who might find themselves in a similar situation.
As an award-winning tech entrepreneur and product consultant, I’ve worked with companies across Europe, North America, and the Middle East. I’m also an adjunct faculty member at the Innovation Hub at Florida State University, where I teach entrepreneurship and design thinking to over 100 students per semester. I’ve had the privilege of learning from both global startup ecosystems and the front lines of teaching, and this piece is a bridge between those worlds. My hope is that these lessons offer founders not just advice, but also a deeper sense of honesty, perspective, and practical direction.
Choose a Few Mentors and Actually Listen to Them
One of the most confusing moments in my startup journey came from receiving advice—from too many people. I was fortunate to have access to experienced mentors, but each brought different frameworks, assumptions, and priorities. While their intentions were good, the sheer volume of conflicting guidance left me scattered and second-guessing myself. Instead of building clarity, I built confusion. My team noticed the constant pivots, and I struggled to maintain a clear strategy.
Looking back, the wiser path would have been to intentionally select just one or two mentors who had deep, relevant experience in my industry or business model. Their feedback would’ve carried more weight and offered clearer direction. For anyone navigating this now: Don’t collect mentors like trophies. Choose those who understand your space, align with your vision, and challenge your thinking consistently. Depth of mentorship beats breadth every time.
Keep It Simple and Learn to Say 'No'
One of the most costly mistakes we made was overcomplicating our product too early. In trying to impress users and investors, we kept layering on features, solving adjacent problems, and expanding our scope far beyond what was necessary. The result was a confusing user experience, unclear messaging, and internal exhaustion. Compounding this, I had a habit of saying “yes” to every opportunity—partnerships, features, side experiments—thinking it would help us grow faster. Instead, we ended up scattered, with diluted focus and a bloated roadmap.
What I would do differently is start with a brutally simple offering that solves one urgent problem for one well-defined persona. And I would treat “no” as a strategic tool rather than a missed opportunity. Every “yes” should earn its place by aligning with the core value proposition. To founders in a similar situation: Define your boundaries early. Simplicity isn’t just elegant—it’s effective. And clarity of focus is often what separates a good startup from a struggling one.
Hire Thoughtfully, Scale Slowly, and Value Experience
After we raised funding, I felt pressure to grow quickly and show momentum. We started hiring fast—often without clear roles, cultural alignment, or a defined onboarding process. To conserve budget, we leaned heavily on interns and entry-level talent, assuming they could ramp up quickly and fill gaps. But in reality, this approach backfired. We ended up with an oversized, inexperienced team that required constant training, lacked alignment, and struggled to deliver meaningful results. Instead of accelerating us, it slowed us down and introduced friction at every level.
What I’ve come to understand is that startups should hire slowly and intentionally—especially before product-market fit. I would now focus on building a small, high-performing team with complementary skills and shared values. When funds are limited, fewer experienced contributors will almost always outperform a larger team of undertrained staff. My advice to founders: Validate your core product first, then scale. And when you do grow, prioritize fit, clarity, and quality over speed. Remember, when WhatsApp was acquired by Facebook for $19 billion, its team was fewer than 60 people.
Don’t Try to Do It All—and Don’t Burn Yourself Out
In the early days, I wore every hat—product manager, marketer, fundraiser, support agent. I thought doing it all myself was a badge of honor, and in some ways it was an intense learning experience. But it came at a steep cost. I moved slower, missed opportunities for delegation, and delayed professionalizing the business. Worse, I neglected my health completely. The combination of stress, long hours, and emotional isolation eventually caught up to me—I hit burnout multiple times and even ended up hospitalized. I didn’t realize just how deeply this journey would test my physical and mental limits.
If I could go back, I would reframe my role not as the one who does everything, but as the one who builds systems and finds the right people to execute. For founders in similar situations: ask for help early. Bring in collaborators where possible—even part-time or freelance support can ease the burden. And prioritize your health like a business asset. Sleep, movement, proper meals, and rest aren’t luxuries—they’re productivity tools. A thriving startup requires a thriving founder. It’s not about running harder; it’s about running sustainably.
Track What Truly Matters and Be Ruthlessly Realistic About Money
In the early stages, I paid attention to the wrong numbers. I got excited by vanity metrics—social media followers, likes, website visits—thinking they were indicators of success. At the same time, I was overly optimistic about how quickly revenue would come in. I assumed we’d sign customers faster than we actually did, and I underestimated how much time and effort real sales cycles require. This combination of misfocused metrics and unrealistic expectations led to financial strain, missed targets, and poor decision-making under pressure.
Looking back, I should have set up a clear dashboard of actionable metrics—like customer acquisition cost (CAC), lifetime value (LTV), retention, and burn rate—from day one. These numbers tell the real story of business health. For founders navigating early-stage growth, I recommend embracing financial discipline and planning for a slower ramp-up than expected. Make conservative revenue projections your baseline, and treat early income like a bonus, not a given. Revenue is hard-earned: Plan for that reality, and your startup will stay alive long enough to thrive.
Research Deeply, Then Build Selectively
I jumped into product development without truly understanding my users. I had a general sense of the problem but didn’t sit down for enough one-on-one interviews or dig deep into the emotional triggers and real-world behaviors of the people I was building for. As a result, we built a product based on assumptions. Later, when we finally conducted proper research, we discovered major disconnects between our features and what users actually needed. We had also prioritized features based on internal brainstorming, not on user pain points or business value. That led to wasted time, bloated development cycles, and resources spent on features no one used.
If I could do it again, I’d start with rigorous customer discovery. That means structured interviews, shadowing potential users, testing early prototypes, and validating problem-solution fit before writing a single line of code. Once that foundation is in place, I would use frameworks like the RICE or MoSCoW method to prioritize features based on value, effort, and alignment with core user needs. For founders today: Don’t just build what sounds good—build what’s needed, and let real user data lead the way. The earlier you listen, the less you’ll waste later.
Don’t Fake Certainty—Stability Takes Time
In the early stages of building my company, I felt a constant pressure to “have it all figured out.” Even when I wasn’t sure, I pretended to be. I made commitments I couldn’t fully deliver on because I thought that showing hesitation would undermine confidence in me as a founder. But that approach backfired. Instead of earning trust, it strained relationships and set unrealistic expectations. I underestimated how long it takes to build true operational stability, both within myself and across the team. In trying to move fast and appear capable, I ignored the importance of being honest about what I didn’t know—and that slowed our long-term growth.
If you’re in a similar position, know this: it’s okay to not have all the answers. You don’t have to promise certainty to prove your worth. What matters more is being grounded, honest, and thoughtful about your decisions. Say “I’ll get back to you” when you’re unsure. Surround yourself with mentors or advisors who have done it before. Most importantly, give your company—and yourself—time to evolve. Sustainable success isn’t built on charisma or speed alone. It’s built on clarity, humility, and the steady work of learning and improving day by day.
Final Remarks
Building a startup is an exhilarating but challenging experience. The mistakes I made taught me invaluable lessons, and I hope sharing them helps others navigate their own entrepreneurial paths more smoothly. The key is to stay focused, adaptable, healthy, and committed to learning at every step. Success isn’t just about speed. It’s about resilience, strategy, and making the right decisions along the way.
