My Leap

In 2016, I left a lucrative career as a portfolio manager and investment strategist at a Fortune 100 insurance company.

I didn’t wake up one day and decide to quit. The seed was always there. When I interviewed for the job twelve years prior, I was asked the typical question: “Where do you see yourself in ten years?” My answer: “I’ll be surprised if I’m not doing something entrepreneurial.”

I’ve always been a builder. The entrepreneurial fire was there from the start.

I also loved investing. Good investors study how the world works, spotting trends and looking to the future. But as technology reshaped the world, I felt stuck on the sidelines.

The 2008 financial crisis reinforced another truth: the stability of a 9-to-5 job is an illusion. That realization pushed me to start preparing for my own leap.

I wasn’t sure when or even if I’d make the leap, but I wanted to be ready.

Here are the five areas I focused on before stepping fully into entrepreneurship.

Mindset Shift

Re-examine your fears.

The first issue of The Leap was titled Misguided Fear for a reason. The 2008 Financial Crisis flipped my perception of risk. I realized my job wasn’t nearly as secure as I thought and that fear of leaving was often less rational than the risk of staying.

That’s why I recommend using the Fear Inversion Framework I outlined in Misguided Fear. It’s the best way to understand how your current fears may be holding you back.

Failure is a feature. 

You will fail, privately and publicly, even if you ultimately succeed. As an investor, I learned this early: even the best investors are wrong almost as often as they’re right.

The key is internalizing that failure is valuable, as long as you’re learning and not repeating mistakes. Entrepreneurship is often about how quickly you can learn the game by speed-running failures.

The Messy Middle 

Lurking in the messy middle lie trenches of tribulation.

The messy middle is the long, difficult stretch between the excitement of starting and the clarity of success. It’s where you flounder, pivot, and struggle. And sometimes, the trenches get extra dark.

For me, that happened in the summer of 2020:

• Business failure – I had to lay off our entire team on a Zoom call after our deal with Amazon Game Studios collapsed and funding dried up.

• Family health crisis – My father, diagnosed with Stage 4 lung cancer weeks before the COVID lockdowns, was given weeks to live.

• Isolation – My brother and I alternated caring for him out of state. A COVID outbreak at my house kept me away from my family for nearly a month.

It’s no coincidence stoic practices like premeditatio malorum (negative visualization) became popular in startup circles. They prepare you for the worst, so when the trenches appear, you’re emotionally ready to keep moving forward.

Routines

Productivity isn’t about doing more, it’s about creating space for creativity. Before you leap, upgrade your routines.

Health is the foundation.

Months before leaving my job, I completed a half Ironman. I couldn’t maintain that level once I shifted to building a company, but the fitness base mattered. Daily workouts and good sleep became less about peak performance and more about resilience and recovery.

Prime your brain for ideas.

I trained my creativity by writing down ten ideas a day. Everything from business concepts to silly inventions like a better chicken slicer. The ideas themselves didn’t matter. The practice rewired me to spot opportunities everywhere.

Manage your energy, not just your time.

Productivity is about using your best hours well. I reserved mornings for creative work, saved admin for the afternoon, and built in quick recovery practices including walks, workouts, or unplugging from my phone. Energy is renewable if managed, but without it burnout comes fast.

Routines create capacity.

Habits either drain or fuel you. Strong routines in health, creativity, and energy management give you the capacity to endure setbacks and stay sharp long enough to break through.

Network and Community

Start building relationships, both in person and online, with people in the community you hope to join. Long before I left the corporate world, I was already immersing myself in entrepreneurial circles. For example:

• Startup Weekend – a Friday-to-Sunday hackathon where teams launch businesses.

• Local angel groups and incubators – I attended their meetings and networking events.

• Online communities – I followed and interacted with other entrepreneurs regularly.

Make your own list of relevant communities and individuals in your target market. Then actively look for events, groups, or simple ways to reach out. You’ll be surprised how open and welcoming most people are when you show genuine interest.

Skills and Knowledge

I knew I had to upgrade my talent stack before making the leap. My background was deep in financial markets and investing, but I wanted to build a technology company. That meant filling gaps in several areas:

Sales and Marketing Fluency

Reading books was helpful, but not enough. If you’re technically minded, find real sales experience, even fundraising for a charity counts. Nothing replaces the confidence gained from asking someone for money.

Technical and Operational Literacy

I learned basic software development. I didn’t aim to become a technical founder, but I wanted enough understanding to recognize challenges and communicate effectively with engineers.

Meta Skills

These are multipliers: learning how to learn, storytelling, negotiation, and decision-making under uncertainty. My investing career prepared me for most, but storytelling was a blind spot. Books helped, but creating real narratives around selling would have prepared me better.

Domain-Specific Knowledge

This depends on your industry. For me, it was video games. I was a casual gamer but didn’t understand game loops or mechanics. I studied the history of gaming and dug into what makes certain games addictive.

Business Fundamentals

Even with an MBA, most of my training was investment-focused. Brushing up on accounting, operations, and HR was essential. You may never run payroll yourself, but knowing how these functions work builds confidence and prevents costly mistakes.

Do The Thing

Just start, no matter how small.

Through networking, I met a group running a motion graphics studio. They wanted to shift from client work into making video games. I funded and helped build their first title, XPets.

That project became the bridge to my eventual leap. I not only learned the fundamentals of game development, but I also got to know the people I’d later join forces with full-time. Looking back, the skills I gained were valuable but the relationships were even more important.

Your first project doesn’t have to succeed it just has to teach you and connect you.

The Next Step

The hardest part is starting. Don’t wait for perfect timing. Build the habit of doing now. Small actions compound, and each one moves you closer to the leap.

At the same time, honor your current job. How you work now is how you’ll work later. Integrity, discipline, and follow-through are transferable skills.

Use today as training for habits, skills, and character. Then, when you leap, you’ll bring more than ideas. You’ll bring the discipline to see them through.

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.