I wrote a post about why I wasn’t scared to leave corporate America. In that post, I committed to providing a detailed list of all the factors that allowed me to transition without fear. Here’s the list:

• What could go right – I focused on this, not what could go wrong.
• Superman syndrome – I hadn’t yet experienced any serious professional failures and basically thought I was invincible (typical early 20’s mentality). Note: I experienced many failures and was humbled many times over while building CCAW.
• Experience – This would be my second “official” company. My prior startup experience, my education, and my corporate experience made me “feel” much more prepared this time around.
• No career path – There was a clear path to being an EY partner in 15-20 years. The downside is that it is (or was back then) an up or out career path. You progress, yearly, towards partner, or you’re out. I didn’t want to be a partner, so I knew my days were numbered.
• Can’t hit what you can’t see - Working in a large company and with other large publicly traded clients gave me a clear idea of what well-run companies looked like. I knew what I was aiming for and felt confident I could replicate it. Side note: They look like well-oiled machines from the outside, but they’re not. There’s always a fire drill, crisis or some critical system failure when you peek behind the curtains.  
• Financially de-risked – I was traveling a ton, so a large percentage of my expenses were paid by EY. I also had two roommates. This allowed me to save a sizeable cushion. Feedback from others heavily influenced how I came up with this plan.
• Business de-risked – I actually started working on CCAW while still employed and using EY resources (which was probably against company policy). I was able to build relationships with suppliers and gain traction with customers before quitting.
• Reputation – I made sure I did a stellar job on all projects and got along with all team members. I never wanted to burn bridges or have a bad reputation. I wanted to leave on great terms.

Looking at this list now, it gives the impression that I was this well-thought-out young person. I wish that was true. In reality, I wasn’t. I was actually stretched super thin and all over the place (literally, too, since I was traveling every single week). What I was actually doing was staying true to my passions (entrepreneurship and personal finance), staying true to the values instilled in me by my family (do your best, treat people well and never burn bridges) and throwing stuff at the wall to see what stuck. Mix in a little luck and good timing and I found myself in a position to take a leap of faith.

Takeaways:

• Venture capitalists like betting on people with entrepreneurial experience. I now understand why. If you have an idea, give it a shot (even if you keep your job). You never know what could happen. Worst-case, you’ll learn a lot that can be applied to the next idea.
• My approach was the product of my young age and lack of responsibilities. However, I do think some (maybe not all) of the things I did might be applicable to others at different life stages thinking about entrepreneurship.
• Making the people who cared about me proud by taking a corporate job was nice, but my heart wasn’t in it. I’m an entrepreneur at heart. I like building things or helping people who are building things.
• Stay true to your passions and values. You never know where they’ll take you.