I’ve thought about what hindered and helped me as an entrepreneur. The list is long . . . really long. One realization: my more-than-a-decade-long journey was segmented. Each segment demanded something different from me. First came ideation. I tested until I found a viable model, persuaded customers and vendors to work with me, and figured out how to finance everything. Later, at $5 million in revenue, came the scaling segment. I needed to expand the team, build scalable systems and processes, and share my vision. There were other segments too. These are just two examples.

In hindsight, not knowing what to expect hindered me. I hadn’t seen the movie. I didn’t understand there would be segments. In fact, I didn’t understand a lot of things. I spent a ton of time figuring out where I was, what was going on, and what I needed to do to progress. Sound like a lot? It was. Doing it all at once slowed me down. Luckily, eventually I was able to surround myself with credible entrepreneurs who illuminated the journey by telling me about their experiences. Then I knew where I was and what I needed to do, and I just had to execute. Of course, I’m oversimplifying, but you get the idea.

Understanding what segment I was in, knowing what skills were important in that segment, and walking it with folks who’d done it successfully were game changers.

If you’re an entrepreneur looking to accelerate your progress, consider learning what the whole journey will look like, identifying what segment you’re in, and learning from people who’ve already navigated it.

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Today marked the end of my thirteenth week of working exclusively from home. Here are my takeaways from week thirteen:

• Reflection – Taking time to reflect and record my thoughts was beneficial. Putting ideas on paper helps me clarify them. And that makes me more comfortable sharing them in conversation.
• Breakthrough – Two people who read one of my posts pointed out a breakthrough I’d made. It hadn’t occurred to me. I realized they were right when I thought about it. Sharing thoughts and being open to feedback can be powerful.
• Focus – The nation is still troubled, but this week was better for me. Not back to normal. Just better. I was able to focus on work. The issues still bother me, but not to the point of paralysis.
• New work normal – Haven’t completely figured this out yet. I did test working from a small private office for a few hours. Mentally, what a huge change! I could concentrate and be more productive. The building was empty and I was alone, so I felt safe. I’d like to do this more often.

Week thirteen was much better than last week. My big takeaway: continue sharing my thoughts and asking for feedback.

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

Achieving entrepreneurial success can take many years. Many things make the journey difficult, but I believe gaps play an outsize role. Big relationship, knowledge, or capital gaps can break an entrepreneur. Maybe you don’t know anyone to introduce you to a decision maker in your industry. Or you’re unsure how to recruit the right team members. Or you don’t have the money to fund your growth plans—and don’t know how to go about acquiring it. I want to be clear: all entrepreneurs have gaps—extra-large ones are what I’m referring to.

To succeed, you have to figure things out as you go along. You must find the ideal path to your destination. If your gaps are yawning abysses, you’re looking for a path that’s in pitch-black darkness. But if they’re minimal, the path is lined with bricks and LED lights. You still have to find it and walk down it, and there will be obstacles along the way, but it will be far less difficult and time consuming to traverse.

My gaps were huge when I founded CCAW. I didn’t realize they were, though, until I surrounded myself with others through organizations like EO. I was able to start filling those gaps with their help. It’s still a work in progress, but plugging my gaps gave me a much better chance to succeed.

I’m a strong believer that Atlanta’s entrepreneurial ecosystem can reach the next level. The city has a lot going for it. Let’s help rising entrepreneurs who have big gaps gain the knowledge, build the relationships, and acquire the capital they need. Together, we can help Atlanta reach its full potential!

What motivates an entrepreneur is important. The journey is tough and full of emotional highs and lows, and it usually takes many years. The right motivations help you make it to the finish line. Yesterday I wrote about my why, which is one of my motivators as an entrepreneur.

I’ve noticed a few things about my motivations over the years. I can have more than one at a time. But one—my why—always dwarfs the others. It’s usually the only one that I have strong convictions about. Historically, I’ve been happier with decisions based on it. I call it my one-to-one rule, and it simplifies my decision-making and how I move forward. When I’ve made decisions to satisfy more than one motivation, it just hasn’t turned out as well.

My motivations change over time. I originally was passionate about helping automotive consumers because I was a car enthusiast (still am). Now, it’s helping entrepreneurs (small and medium-sized businesses). Why? Material things matter less as I mature. I still love cars, but not as much as I love people. These days, I’m motivated to help people I can relate to.

Motivations are important. They helped me stay the course during my entrepreneurial journey. Do you know what motivates you?

Last week I taught Intro to Entrepreneurship at Atlanta Tech Village’s Startup Summer School. My session touched on the need to know your why. Since then, I’ve been in touch with a few of the people who attended, helping however I can. This morning I received a Slack message from one of them. He asked a great question: “So what was your why with CCAW, and is it changing as you start your next chapter?”

This entrepreneur’s business is in its early stages but making great progress. He built a working MVP and then signed twenty or so paying customers within a few months of launching. All during a pandemic. He’s on to something, in my opinion.

When I started CCAW, I was a few years removed from being an undergrad. I had some corporate experience and no real responsibilities. A car enthusiast for years, I had automotive parts relationships. As a parts consumer, I knew how difficult acquiring the right part at a fair price could be. In high school and college, I had a company that developed and executed plans to customize customers’ vehicles (think Pimp My Ride). Having worked with parts manufacturers and distributors, I knew their struggles well. My why was simple: I wanted to help consumers easily connect with parts companies. This would help two groups I was familiar with. There was also a financial motivation, but it was secondary.

Now to part two of his question. What’s my why for my next chapter? I’ve thought a lot about this and it’s simple, too: I want to make life easier for entrepreneurs and small and medium-sized business. Especially those with big gaps in knowledge, relationships, or capital. (In other words, people like me in CCAW’s early years.) I know their struggles. I’m one of them, and I’m passionate about helping them. If I’m successful, I’ll accelerate their success. I’m hopeful they’ll give back to someone else when they’re able to.

My whys were born of my personal experiences. That makes me credible and able to relate well with the folks I seek to help. And it drives the passion behind my why.

What’s your why?

I recently had a conversation with an aspiring entrepreneur. She’s passionate about an idea and has the technical training to execute it. She asked my opinion on various things, which I happily gave. But she still wasn’t quite sure what to do next. I asked, “What’s the single most important thing you can do right now?” She named something. I suggested she start by taking action on that one thing.

As we talked, I thought about my journey as an entrepreneur. Early on, I was full of ideas and didn’t know where to start. When I was working with others, we could talk endlessly. Sometimes the sheer number of possibilities felt paralyzing. Indeed, sometimes I was paralyzed. Over time, I learned that one thing matters: action. It was action that would change a situation. It was action that would turn my vision into a reality. It was action that would separate us from others. At a certain point, I had to stop talking and start doing.

That lesson took me years to learn, but I’m glad I did. Taking action on something, even when the way forward isn’t 100% clear, has been my key to progress. It changed my life.

I’m encouraged by the positive conversations we’re having as a nation about race and police brutality. They’re overdue and they’re helping us gain the understanding of one another that we so badly need. As you have these conversations, consider asking yourself a simple question after each one: “What action am I going to take now?”

Today marks my ninetieth consecutive day of sharing my thoughts in posts. (I previously described how this started.) I recently spoke with a peer about my experience. He’s considering doing it too and wanted to ask me a few questions. By the time we finished chatting, I had had an epiphany: I understand things better when I share my thoughts widely.

I tend to think deeply about things. I try to understand by identifying connections that aren’t obvious. I used to ruminate and perhaps talk with one or two people very close to me. That approach was flawed. It didn’t help me achieve my ultimate goal: understanding.

It was a mistake to not share my thoughts or to do so only with a few like-minded people. I avoided opening up to others with different perspectives who would test my thinking or point out my blind spots (we all have them). I wasn’t really trying to understand, because I wasn’t talking to people who would be likelier to disagree with me. Naturally, I saw things only through the lens of my life experiences. My reality. I would come to understand an issue, or think I did, but since I looked at it only from my own narrow angle, I ended up missing things.

Sharing my thoughts broadly invites feedback. It sparks great conversations—opportunities for me to listen. I get glimpses of other people’s realities. I see things from their angle! I’ve learned that truly understanding something means getting as close as possible to a 360-degree view of it. The more people I talk to who are different from me, the closer I get to that goal.

Sharing my thoughts daily has illuminated all of this. Sometimes my initial thinking is wrong. (Whose isn’t?) When I share my thoughts with the world, I’m inviting others to help me acquire true understanding. Each person bridges a gap in that 360-degree circle.

I didn’t envision understanding things better as a benefit of sharing when I began posting every day, but it is, and I’m thankful for it.

I encourage everyone to share their thoughts more widely. It doesn’t have to be through writing; do it in a way that works for you. When you get feedback, listen. You’ll understand things much better.

This week, I shared some lessons I’ve learned with Startup Summer School attendees. One of the biggest was how important a cofounder is. I started CCAW as a solo founder. Even though it worked out—CCAW was a success—it was painful. Our progress was slower than it could have been and I was stretched super thin. I’ve thought more about why a cofounder is so beneficial. One word sums it up: accountability.

I often hear “not having to report to anyone” and “being my own boss” as top reasons for being an entrepreneur. But the most successful entrepreneurs are accountable to someone: a board of directors, cofounders, investors. Accountability leads to success. No accountability can prevent or slow your success. Why is that?

Accountability means that you’re expected to deliver on commitments by taking action. Others are relying on you. If you don’t deliver, there are clear repercussions for yourself and others. Translation: you can’t do whatever you want, whenever you want.

When you’re accountable to no one, you don’t have to commit. No commitment means no clear repercussions. Translation: you think you can do whatever you want, whenever you want. Entrepreneurship is all about taking action to meet a goal. But when you’re not accountable to anyone, you tend to take action when you want to, not when you need to. Over time, no action or slow action hinders you. And you shortchange yourself and everyone who works for you but doesn’t have the power to hold you accountable.

If you’re starting a company, try not to go it alone. And whatever you’re doing, find a way to make yourself accountable to someone.

Today marked the end of my twelfth week of working exclusively from home. Here is my takeaway from week twelve:

• Focus – We’re experiencing troubling times as a nation. It took a big toll on me. I was distracted and struggled to focus. Talking through this with others helped a lot.  

Week twelve was a rough week. Ironically, it had nothing to do with working from home. My big takeaway: Understanding each other will lead us to appreciate each other.

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

In an earlier post, I shared my views on the power of listening to understand. I’ve continued to think about how we can help each other through this turmoil.

As CCAW grew, our team grew. I was no longer involved in every decision or even aware of every initiative. An empowered team making decisions without me was my goal. Inevitably, some decisions didn’t result in the desired outcome. Translation: things blew up sometimes.

No one is perfect, and my team members had good intentions. We were all in it together, working to build a great company. Naturally, we sometimes had different ideas about how to do it. Our different perspectives were valuable and often lead to amazing outcomes. But sometimes they caused us to miss the mark.

By the time something reached my desk, it usually meant a decision had worked out poorly. Instead of beating a dead horse, I learned to focus on the reasons for the decision. Why did you do it that way? Why was that the chosen path? What led up to you making that decision? Asking these questions was far more valuable than casting blame. I listened with the intent to understand, and ultimately, I did—I understood their why. Then I was able to work with them to develop solutions that supported their why.

Understanding why begets perspective. More importantly, it gives insight into the other person’s perspective. Understanding why someone makes the choices they do is a building block in (or even the foundation of) the positive working relationship required to achieve a common goal.

We’re all in this together, but that doesn’t mean we all see things the same way. Consider listening to understand why. When you do, you can begin to see things from a different perspective.

You might be interested in this short video about Colin Kaepernick's and Army veteran Nate Boyer’s desire to understand one another. It led Nate to “understand that we’re not that different, and we probably want the same things at the end of the day” and to a compromise that incorporated both perspectives.

Be part of the solution. Understand why.