Taking the Leap

Entrepreneurship is Hard

Starting a business is a challenging endeavor, often ignited by a simple idea. Perhaps you’ve jotted it down on a napkin during a brainstorming session with close colleagues. Whether you’re a software developer, a consultant, a salesperson, or just someone who’s spotted an untapped opportunity, you decide to venture into a side hustle. Before you know it, you’ve acquired your first few customers and things are going surprisingly well, even if you’re not entirely sure why.

Then comes the next phase: you start building a team. And suddenly, you realize your role has evolved. You’re no longer just an expert in your field; you’re a leader. Your days shift from doing the work you’re accustomed to, to guiding and empowering others to do that work effectively. You realize at some point that Entrepreneurship begets Leadership. For me, my largest challenges were as a leader so I plan to share those experiences in this series of articles.

Make no mistake, stepping into the shoes of a founder, small business owner, or first-time leader is incredibly rewarding. I believe it’s one of the most fulfilling journeys you can embark upon in your professional life. But let’s not sugarcoat it — leadership is hard. You’re also not alone in your journey. I hope you find some of these experiences relatable and come to realize that the challenges are surmountable and your fellow leaders are here to help.

Leaders are not Alone

If you’ve had some experience in the world of business, you’ll know that the most significant challenges often come down to people. As someone who has founded multiple companies — some successful and some failed — I can attest that the early stages of building a team are crucial.

It’s even more essential how you handle the stormy debates that naturally arise and how you establish norms. These early decisions have long-term effects on a team’s performance and, ultimately, your company’s success.

In my journey, I have noticed one challenge that all of us seem to face and it’s something

I’ve faced several times myself, The Peter Principle.

Navigating the Peter Principle

The Peter Principle, first coined by Dr. Laurence J. Peter, is a stumbling block that many first-time founders, small business owners, and new leaders encounter. The idea is that people often get promoted to their “level of least competence.”

Generally, you have performed very well as a senior individual contributor and it seems like the next steps for career advancement are into a Leadership position. However, once you move into your first Leadership role, you find out it’s almost a new career field and you may be woefully unprepared for the next few steps in front of you.

Before we dive into the traditional scenario, it’s crucial to note that this principle can apply in various contexts, not just when transitioning from a hands-on role to your first leadership position. It’s something that a person can work through and learn from — in fact, the best leaders become stronger from their time wrestling with the Peter Principle.

In my own career, I’ve hit this wall multiple times — whether as a new team leader, a first-time small business owner, or even midway through my tenure as Co-founder and CTO of Horangi Cyber Security.

The First-Time Leader’s Challenge

Stepping into my first leadership role was nothing short of daunting. I found myself in the role of the first Forward Deployed Security Engineer at Palantir, a position that carried with it a considerable amount of informal leadership responsibilities.

Before this, I was deeply immersed in my technical role — my comfort zone — and the assumption was that my technical acumen would naturally translate into leadership prowess. This couldn’t have been further from the truth.

In this new role, I found myself liaising between our unit and other business units within Palantir. I was no longer simply responsible for code or data; I was responsible for relationships, timelines, and cross-functional collaborations. And these were waters I had never navigated before.

Technically, I felt at home. But leadership is more than technical knowledge; it’s about people management, communication, and, more importantly, relationship-building. Early on, I struggled with managing relationships among my peers in other business units.

I was adept at talking tech, but when it came to aligning our objectives with theirs, prioritizing tasks, or even just effectively communicating our team’s capabilities, I fumbled.

I had the added challenge of understanding that my colleagues in other business units had their own agendas and priorities.

The ability to negotiate, compromise, and come to a mutual agreement was something I had not anticipated needing in my toolkit. I realized, perhaps a bit too late, that leadership isn’t about having all the answers but about fostering an environment where answers can be found collectively.

Eventually, it became clear that my inability to transition smoothly from a technical role to a leadership one was affecting not just me but the productivity and morale of the teams I interacted with. And that’s the moment the Peter Principle really hit me: I was competent in my previous role but less so in my new one, especially when it came to navigating the complexities of inter-departmental relationships.

This experience was a wake-up call. While I thought my technical skills would be my greatest asset in a leadership role, I learned that the soft skills I had overlooked were equally, if not more, important. I had to accept that I was a work in progress as a leader, and that was okay. It was an invaluable lesson in the endless journey of leadership. And it was a lesson not just in humility but in the importance of continual self-improvement and adaptation.

The First-Time Business Owner’s Challenge

Having cut my teeth as a new leader and then hitting my comfort zone again, I decided to start a side hustle that has deep familial roots — Metalworking. I knew that starting a business is tricky, and new owners often don’t realize just how many things can go wrong.

Whether it’s sales, marketing, or the nitty-gritty details of operations, you’re bound to mess up somewhere. Having grown up watching the entrepreneurs in my family, I knew facing these challenges was effectively a rite of passage for every entrepreneur, including me.

When I teamed up with my friend Oliver in 2015 to launch Prohibition Metalworks, I thought I had it all figured out. We had a clear service, welding stainless steel glycol coolant lines for new craft beer breweries in North Carolina. Our state had the fastest rate of growth for new breweries at the time and we wanted to capture the opportunity.

I assumed my cyber security background and having been around business-savvy people all my life would make me a pro at running a metal fabrication business. To top it off, I was confident I could juggle this new venture while keeping my full-time cyber security job. Gosh, was I wrong.

Time was not on my side, and that was just the start. Taxes confused me, and I didn’t get how invoicing was related to actual cash in the bank. Terms like ‘operational expenses’ and ‘capital expenditures’ were foreign concepts. I was also pretty clueless about the metalworking side of things, which meant I wasn’t giving Oliver the support he needed. I also didn’t want to admit my lack of competence to either Oliver or myself.

But it wasn’t all bad — I’m just honest with myself and a bit too harsh sometimes; I had a strong network, I was good with people, and I had determination. Oliver is an amazing guy, and we could have achieved more if I had been a better support.

This time, my failure wasn’t due to a lack of “soft skills” like people management. Instead, I stumbled on the “hard skills” — the technical know-how that I didn’t even realize I was missing. So, in a different twist, the Peter Principle struck me again: I was competent in my old job but out of my depth in this new venture.

When The Business Outgrows You

In 2016 I had an opportunity to take a big swing and Co-Founded Horangi Cyber Security Singapore alongside Paul Hadjy. With all that I had learned, I felt prepared to face new challenges 12,000 miles from home with limited resources and a limited network. It was FUN! We crushed it, we did a lot of things in Singapore for the first time, we helped grow the start-up community, and we built a great team. We were doing awesome things and growing fast.

However, it would only be 4 or 5 years before I learned my hardest Leadership lesson to date. Sometimes, it’s not you but the landscape that changes. Your business, your team, or the market can evolve, leaving you ill-equipped for your transformed role. That’s what happened to me at Horangi.

The company grew; we hired skilled people and began narrowing our focus. We stopped doing the type of work I had the most experience with and had to stretch my skillset and start working on things I didn’t find intrinsically rewarding. Suddenly, I found that I wasn’t just unfit for my role; there was no role where I could continue providing the same level of value to my team.

The company had grown faster than I could and, as much as I didn’t want to admit it to myself, it was time for me to step down and get out of my team’s way. This is one of the hardest situations a founder can face and one of the hardest decisions a founder is forced to make.

After sharing my story with several other entrepreneurs, I’ve discovered that I’m not alone in this and there are quite a few founders who have faced the same situation. Just remember folks, leadership is hard but you are not alone. Ultimately, Paul and the Horangi team were acquired by Bitdefender earlier this year and I couldn’t be more proud of the team’s accomplishments and how well they grew the things we built together.

Remember, there is also no final destination in leadership. It is a lifelong journey of continuous learning and immense reward. There’s never a point when you’re entirely ready for what’s next, which rings especially true for entrepreneurs.

How to Navigate the Pitfalls

I don’t pretend to have all the answers. All I have is a bit more wisdom than I used to have and some methods that have worked for me to overcome the Peter Principle. If you find yourself in a situation where you’re no longer competent in your role, consider the following:

• Mentorship: Keep a circle of mentors whose advice you trust and respect. Make sure you have mentors who can help you bolster your strengths and identify areas of weakness. These individuals should be comfortable giving you the hard truth and you should have an open mind as they share their experiences.
  

• Self-Assessment: Be honest with yourself about your skills and areas where you fall short. Self-reflect regularly. Adopt one of the frameworks out there from John Maxwell, Gino Wickman, Stoicism, etc. The framework you adopt doesn’t matter so much, it’s just important to self-reflect and know if you’re headed in the right direction or not.
  

• Feedback Loop: Regularly seek performance reviews not just from your team but also from peers and superiors. This is just as important if not more so than mentors. Doing it effectively requires building rapport with your team and creating a culture of honesty and candor. Sometimes these are called 360 reviews, however, I have found that the leaders who build these feedback loops into their natural working habits rather than regularly scheduled business processes are more effective with their teams.
  

• Role Adjustment: If you find that you’re more of a hindrance than a help, it may be time to redefine your role, move to a new role, or even step down. I’ve done this in my career. I was a Co-Founder and CTO, then I was a Chief Incident Response Officer, but now I am in a role as a Principal Investigator with a couple of extra entrepreneurial duties. There’s nothing wrong with taking a step back and reevaluating yourself, in fact, sometimes is the best thing you can do. You just need to have the courage to do it.
  

At the very least, by working through these techniques, you’re not just acknowledging the challenges you face; you’re actively working to overcome them.

Conclusion

In closing, leadership is not for the faint of heart. It is complex, demanding, and at times, intensely challenging. But you’re not alone. The life of a leader is not as lonely as it was once described and we can walk the path together.

For those willing to embrace the intricacies of leadership, the payoff is not just success in the traditional sense, but a profound impact on people, communities, and perhaps even the world at large. So, if you find yourself in an unexpected yet privileged position of leadership, brace yourself for a fulfilling, albeit rugged journey. Take a deep breath, roll up your sleeves, and get after it!

Lastly, I am here to help you folks and I only grow with feedback. So please leave a comment below and let me know what you thought of this article (good or bad) and if you would like me to share more experiences.

Special thanks to my friends, mentors, and colleagues.