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.

In a previous post, I shared what I learned from my first company. It taught me a ton, but I never figured out how to transition it from a hustle to something sustainable. That realization, my desire to make my parents proud, and an urge to keep up with my classmates resulted in my happily agreeing to work for EY in Atlanta. To be totally transparent, I also wanted to move to a big city and travel on someone else’s dime. (Side note: I almost accepted a job in San Francisco —until they casually mentioned I’d probably need four roommates.)

Personal finance has been a hobby since adolescence; that was a big part of the reason I majored in finance. The summer after college, I was curious what my financial life would look like with a real job in a big city. I’d never lived outside Louisiana, earned a salary, or had benefits before. I decided to create a budget for my new corporate life in Atlanta. My forecast was crude, but the exercise was helpful. Even though I’d studied finance and read avidly about personal finance, my knowledge gap was HUGE. I decided to fill that gap and get perspective from others. My hope was that I could avoid financial pitfalls.

I decided to try to get my forecast posted on a personal finance blog and ask for feedback from its readers. Getting any response from bloggers was a 50/50 proposition, I figured, and I expected a demand for compensation if they did reply. There was no downside, though. From my previous experience, I had learned the value in simply trying.

I emailed my forecast to a popular personal finance blogger. To my surprise, he agreed to post it and didn’t ask for payment. You can see the post, my forecast (don’t laugh), and the feedback here. The feedback came in quickly and was pretty diverse. There were financial suggestions, as expected, but also advice on how to live life. All these years later, I’m still surprised and thankful that this blogger and so many of his readers were willing to help me out by sharing their experiences and perspectives. Their feedback helped me prepare for life in a new city and transition smoothly to corporate America.

Here are my takeaways from the experience:

• ‍Perspectives – Everyone views life through a unique lens. For a variety of reasons, we don’t all see things the same way. There is value in trying to understand other perspectives (even if you don’t agree with them). Listen with an open mind.‍
• Knowledge gaps – Nobody knows everything. Seek knowledge from credible sources and people. It will help you make good decisions.‍
• Right answer – The right thing to do may be something suggested by someone else. Getting to the right answer is more important than being right. This is from Ray Dalio’s book, and I agree 100%.‍
• Ask for help – People are often willing to help. Think carefully about what you’d like them to do for you. A specific ask will make it easier for them to help, so they’ll be more likely to say yes.

After building a company for over a decade, I’ve recently become more intentional about mentoring new entrepreneurs (I’ll explain this decision in another post). They often want to know the story of how I started CCAW Automotive Group. Like most people, they usually don’t realize that CCAW was my second “official” company (the fourth or fifth if you count all my childhood hustles). I’ve never shared this before, but here’s the story of how I started my first company.

In high school, my dad’s close friend (I’ll call him Joe) was visiting for Thanksgiving. He saw me heads down, intensely researching, and asked what I was up to. Joe was an entrepreneur. He was super-curious about new things, and it showed. He always engaged with me differently than other adults. At the time, I was into cars and had been trying to figure out how aftermarket auto shops source their products. I figured I could cut out the middleman and get better deals for my friends and me. Keep in mind that this was 1998—information wasn’t as readily available as it is today. I learned about retail and wholesale relationships but hit a wall when wholesalers asked for my business license.

Armed with my research, I proudly told Joe, “When I become an adult, I want to start my own company selling auto accessories.”

He interrupted me. “Why wait until you’re an adult?”

The question caught me off guard. I was speechless. I assumed there was some age barrier to overcome, but I’d never taken steps to find out if that was true. Joe encouraged me to apply for a business license and see what happened. I took his advice, and two weeks later my first company was registered with the Louisiana Department of Revenue. I officially had a business (well . . . kind of).

My takeaways:‍

• ‍Take action. Take the first step. Confirm your assumptions.‍
• Stay curious. Never stop learning.‍
• Give back. Take the time to talk with anyone interested in entrepreneurship. Encourage them. You could change someone’s life!

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