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Life Lessons

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Wouldn’t Change a Thing

Yesterday I caught up with a good friend who’s also an entrepreneur. He said he was recently asked, “What would you change or do differently?” We’ve both been asked this question for various reasons, so we had a great chat about it.

Things will inevitably get challenging during the entrepreneurial journey. Entrepreneurs will find themselves making important decisions based on imperfect information. Having lived this scenario many times, we agreed about what matters most:

  • Everything happens for a reason. The reason may not be clear at the time, but there is one. Take time to reflect on what happened, and why, so you can apply what you learn in the future. What seems like a failure today could be a steppingstone to a decision that leads to massive success. Reflection and the understanding it engenders are key to improving your decision-making.
  • Neither of us would change any of our decisions. We don’t second-guess them. We didn’t know then what we know now, and we stand by our decisions because we did the best we could with the knowledge and other resources available to us. Don’t continually relive the past. Focus on the future.
  • It isn’t over until the clock reads double zero. Stay focused on getting the win. Sometimes you’ll make decisions that don’t pan out. That’s OK. Dust yourself off and get back in the game. Remember that it isn’t over yet and you can still make a comeback. If you win in the end, all your turnovers and air balls don’t matter anymore.

My conversation with my buddy was a great reminder for both of us that we wouldn’t change a single thing. As he so eloquently put it, “All windshield, no rearview mirror over here!”

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Closing Windows of Opportunity

Yesterday, I wrote about the insights Eric Feng shared during the Outlander Speaking Series. One of the things that really resonated with me was his answer to a question. For context, I asked him, “What’s one thing you know now that you wish you had known as a first-time founder early in your career?” Here’s his response: closing windows of opportunity. This has been on my mind all day today.

At CCAW, as at every startup, we always had a ton of things we were working on. Looking back, Eric is so right. I wish I had consistently prioritized opportunities based on their closing windows. Early on, we had an opportunity to be one of the first to offer a specific product category for online purchase by consumers. The market for this category is huge and it was primed for disruption. Being first mover would have required our full attention and fighting some battles to change an antiquated space. There were lots of technical challenges and we lacked a thorough understanding of the category and key relationships in the space. Big hurdles, but they were surmountable and worth the effort because of the size of the opportunity.

I chose to instead continue to focus on a product category that wasn’t growing but in which we had established relationships. Fast forward a few years: we tried to play catch-up in the high-growth product category—but we never did catch up. A competitor beat us to the punch and became a household name. That was a $250-million-annual-revenue decision. I should have pounced on the closing window of opportunity to be a first mover. I didn’t, and we paid the price.

Eric’s concept is simple and spot-on. It applies to everyone, not just entrepreneurs. Here’s an example that everyone can relate to: relationships. No one is immortal, so every relationship is a closing window of opportunity. I wish I’d spent more time with certain people who were in my life when I was young but who’ve since passed.

My mother reminds me often of something my grandmother told her: “Give me my roses while I can still smell them and sense the enjoyment they bring me.” I think Eric and my grandmother are loosely saying the same thing: some opportunities won’t be around forever. Be mindful of which ones are important, prioritize them, and make the most of them while you can—in all aspects of life!

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You Can Handle More Than You Think, but It Takes Time

Recently I was sharing with a buddy best practices I used to manage CCAW. Technology systems. Team alignment frameworks. How I structured my day to juggle my multiple hats. And we talked about how my responsibilities expanded as the company grew. When I finished, he seemed dazed. “Sounds like a lot to deal with,” he said. “How do I get the point where I can handle all that at once?”

As I rattled off all the things I did, I realized it was a lot. The days were packed and the to-do list was never-ending. CCAW was a ship and I was the captain, responsible for it sailing smoothly. With so many moving pieces that kept increasing in complexity, it was no small task to manage it all.

I was always busy. There was never a time when I was like ”Hmmm . . . I don’t have enough stuff to do; I think I’ll go find more to add to my plate so I can keep busy.” As the company grew, we were confronted with new challenges that forced me to rise to the occasion. It was uncomfortable, and each hurdle forced me to take on a little more than I thought I could handle. After years of this, my capacity was many times larger. I was able to handle much more than I thought I was capable of when I started CCAW.

My journey as a founder was one of gradual growth—over years—that came about because I kept being put in uncomfortable situations that tested my limits.

If you’re looking to do something great but aren’t sure if you have what it takes, know this: most people who were once in your shoes didn’t have “it” in the beginning. They grew along the way, and you can too!

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Be Intentional

When I was in the corporate world, the path was clear. You show up and do good work and you’ll be promoted. I didn’t have to put much thought into it. It was known. Chatting with a friend today reminded me that I had to unlearn this and take a different approach as an entrepreneur.

My first few years at CCAW, I worked hard. That hard work was rewarded with (in my eyes) marginal progress, and I was nowhere near where I wanted to be. I couldn’t see a path to get there, either. I’d applied what I’d learned in corporate America, but it wasn’t working very well. Our revenue was growing, but I was struggling in many areas. It felt like I was on a hamster wheel spending more time working in the business than on it. I was stressed and working a ridiculous number of hours.

I eventually decided to take a step back. I realized that I was hoping things would just fall into place. It wasn’t working out like that. I spent time crystalizing where I wanted to be and pinpointing what was preventing me from getting there. I realized that to reach my destination in a healthy way, I would have to be much more intentional. I would need to rebuild our operational foundation and change our pricing strategy. I estimated that it would take a few months and that our revenue would decline during that period.

The process ending up taking a year and reduced revenue almost 30%, from $688,000 to $485,000. It was extremely painful and I was scared. I wasn’t sure that we’d survive this self-inflicted pain. Vendors were asking why we weren’t buying as much and we faced a cash crunch. Ultimately, though, it proved to be the right call. We built a stronger operational foundation and were positioned for growth. The next year, annual revenue was $793,000 and the following year it surpassed $1 million. We were rolling. I was still stressed, but I felt like I could work on the business more and continue to grow.

My takeaway from this experience was that intentionality is powerful. If I want something, I need to articulate it clearly (to myself and others), put in time and effort, and align my decisions with what I want to make happen. That means that sometimes I’ll have to endure short-term pain to reach my ultimate destination, but that’s OK. I have to be intentional about what I do in the present to reach a particular destination. I won’t just miraculously end up there.

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Rookie Mistakes 101: Not Admitting That You Don’t Know

Early in my founder journey, I had an overwhelming feeling that I had to have all the answers. I felt like it was expected of me. Whenever the team asked a question, especially about direction, I thought I should know the answer. I worried that they would lose confidence in me if I didn’t. As I worked with suppliers, it was the same. I felt like I had to have an answer or they would look at CCAW differently. Even when speaking with entrepreneurial peers, I felt the same self-imposed pressure. It was ludicrous.

As I settled into running a company and leading a team, I became more self-aware (partly through reflection on failures and partly from people pointing out my shortcomings). I realized there were things I was really good at and felt confident answering questions about. Other things I was inexperienced in or just plain bad at, and I wasn’t well equipped to answer questions about them. As I matured, I stopped trying to come up with a good-sounding answer that would let me squirm out of the corner I was in when the true answer was “I don’t know.”

Those three words are simple, powerful, and scary all at the same time. They’re scary because you’re admitting you have a knowledge gap. This can feel uncomfortable (it was for me), but it helps to think of saying them as acknowledging that you’re human. They’re powerful because they signal self-awareness, confidence, and honesty, and they give you the opportunity to learn something. And they’re simple because . . . well . . . they’re only three words.

Nowadays, when I’m asked about something outside my wheelhouse, I usually admit my ignorance (I still slip up, though). I try to turn it into an opportunity to learn. Usually I say something like, “Honestly, I’m not sure, but I’m actively seeking different perspectives on this. I’d love to hear yours.” People will tell me what they think, which adds to my fund of knowledge. Or they’ll admit they don’t know either, which reassures me that I’m not the only one.

When I speak with entrepreneurs now, I try to tell them what I wish someone had told me early on. It’s OK to not know. In fact, it’s normal. You’re human and no one expects you to have all the answers!

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How Far Have You Come?

At CCAW, I was always thinking about making the company better. How can we make our customers’ experience better? How can we make it easier for our vendors to do business with us? How can we use technology to improve internal operations and make life easier for our team members? It was a relentless decade-long quest to be better. It definitely worked. We built an amazing company and some pretty cool technology. Admittedly, I pushed extremely hard (sometimes harder than my team thought I should!). In my mind, there were all these ways we could be better and I wanted to attack them! I wanted us to reach our full potential.

One day I had a conversation with my mom that put things in perspective. She reminded me of where it all started and who helped me. In the early days of CCAW, I stored product at my parents’ house (and other places too). My mom constantly asked me, “When are you going to get all these boxes out of my house? This isn’t a warehouse, Jermaine!” My parents lived in Louisiana and I was in Atlanta (or wherever EY had dispatched me for the week). I used spreadsheets to track the product I was storing and manage customer fulfillment. When we sold product, I would get on the phone and coordinate with my Dad to get it to customers. The stuff was heavy and bulky. He usually made time to ship stuff after working a grueling day in the sun at a refinery. Without his help, there’s no way I would have been able to get CCAW off the ground. I’m super appreciative of that help—and of him for putting up with me.

That conversation with my mom stopped me in my tracks. I realized that instead of focusing all the time on making improvements, I should recognize how far I’d come and how other people helped me get there. At the time of that conversation, we were probably doing around $7 million in annual revenue. We had built a completely automated system that fulfilled hundreds of daily orders from dozens of warehouses nationwide. Yes, there were still warts on the business, but it had come a long way.

From Mom, I learned that things will never be perfect and there will always be things you can improve. It’s important to remember to acknowledge how far you’ve come and the people who helped you get there (thanks Dad!).

How far have you come? Who helped you along the way?

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Getting Through Your Bad Days

After I published yesterday’s post, I remembered another question from Friday’s Q&A session that stood out to me:

How do you push through when you’re having a bad day?

Someone who asks this in an open forum is probably seriously struggling with the issue. And there are probably ten more people experiencing something similar but suffering in silence. For this reason, I felt it was an important question to take seriously. I answered it Friday during the session, and I’m addressing it again in this post.

The most important thing for entrepreneurs to understand is that they’re human beings. They’re not superhuman or indestructible. They experience the same emotions as everyone else. And like everyone, they have bad days. It’s OK to have an off day. In fact, it’s normal. When entrepreneurs have an off day, they should be honest with themselves and acknowledge what they’re experiencing. Sounds simple and maybe even stupid, but it’s important. Being honest with yourself is the first step in dealing with a bad day.

Then you can be honest with others. I’ve written about this: support systems are critical to entrepreneurial success and mental wellness. Bad days are one reason that’s true. If there’s someone you trust to act as a sounding board, you can talk with them to work through what happened, and why. Such conversations often help you let go of the troubles of the day and move forward.

Even if you’re having a bad day, stuff still needs to get done. Retail stores don’t close because the staff is having a bad day. You won’t have sympathy for your HR department if your paycheck is late because someone had a bad day. What things do you have to get done, regardless? Create a system under which you’ll be held accountable. There are lots of easy ways to do this. Email updates are a simple approach with numerous benefits. Another effective tool is a daily team huddle or stand-up meeting. Any of these can unlock the power of accountability. I credit accountability for some of my more successful periods. Avoiding it is a huge mistake that many early entrepreneurs make (I know I did).

Everyone has bad days. The key is to recognize one and take steps to turn it around in time to prevent a bad day from turning into a bad couple of days or a bad week.

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Adapting to Change

I shared my transition to venture capital the other day. Since then, I’ve talked with several people about the details. (I’m happy to share, listen, and help however I can.) I’ve noticed a pattern. A lot of people are contemplating or already going through serious life transitions. Professionally, personally—you name it; big changes are happening or on the horizon for many folks. The pandemic surely plays a big role in this. The abrupt change forced us to experience something different. Many are now considering what parts of this change they want to make permanent. And I’m sure there are a host of other reasons too.

I personally think the key to navigating change is being adaptable. Don’t get me wrong; I’m not saying to go wherever the wind takes you. I personally try to evaluate and then embrace the change and make it work for me (if that’s possible). I’ve learned to not make the past my baseline. Instead, I try to accept my current reality, which, admittedly, is sometimes easier said than done. All this helps me to adapt in a way that works for me.

Regardless of how you go about navigating change, be adaptable and do it in an way that works for you. And remember there are lots of other people considering or going though something similar. You are not alone.

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Compounding Reflection

Today I had a conversation with a buddy about reflection. He’s thinking of reflecting more and learning about various ways to reflect. He’s looking for the one that suits him best. I’m a huge fan of reflection. Experience is important, but it’s reflecting on that experience that contributes to wisdom. I wasn’t aiming for this when I started writing earlier this year, but my daily posts have become a form of reflection.  

Here’s what I’ve noticed:

  • Thinking – Coming up with a topic every day is hard. I’m forced to replay the entire day in my mind. What did I work on? Whom did I speak with? What did I read? I look for the most important thing and then think about it more. I consider it from different angles, do a bit of quick research, mull over relevant past experiences . . . whatever comes to mind. I try to connect less obvious dots and better understand my experiences. I usually (not always) uncover a nugget that becomes the foundation of my post.
  • Writing ­– Creating the post is an important part of my daily reflection. It crystallizes my thoughts. It’s one thing to have thoughts in your head. It’s quite another to articulate them logically in writing. Writing helps solidify my learning.  
  • Compounding – Identifying the most important thing that happened every day and making small adjustments in my opinions, beliefs, or decision-making is effective. The effect of compounding lots of small changes over time is huge.
  • Frequency – I’ve found that daily reflection is ideal for me. The rhythm is perfect. I only have to think back 24 hours. If I had to reconstruct a week or a month I’d be bound to overlook something worthy of reflection.

My approach to reflecting probably won’t work for most people, which is understandable. If you’re interested in the idea of regular, intentional reflection, I encourage you to test a few approaches to find the one that works best for you. It’s something simple that can have a powerful impact!

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Comparisons Never Help

Today I had a conversation with a friend. He’s questioning himself even though he’s successful. Are my peers passing me up? Should I be striving for more? Why don’t I have the life others have? He’s comparing himself to people who appear to be more successful.

When I was building CCAW, there was a time in 2011–2012 when I compared myself to other founders and kept score. Am I growing as fast as my peers? Who will reach $1 million in annual revenue first? Why didn’t I think to do X? Why haven’t we implemented Y? This period was short-lived. I thought through things and realized the following:

  • Industry – CCAW operated in an industry that resisted change. And I bootstrapped the company, so we had to be capital efficient. Leaning on partners to warehouse products and fulfill our orders was a capital-efficient model. We were attached to their hips for better or worse. We had lots of great ideas but couldn’t execute them without partner buy-in. Our growth was heavily affected by our partners’ willingness to embrace change. They often did so only slowly, after years of conversations.
  • Gaps – My peers all had different backgrounds. Some came from entrepreneurial families. Some had worked in startups before. Others were starting their second or third company. I was from a family of folks who worked for other people, I’d worked in the corporate world, and I was building my first company. They had entrepreneurial knowledge gaps—I had chasms. It took time to learn what I didn’t know, so my path to success was longer.
  • Outside looking in – You never know someone’s full story. Their life may look great, but they could be in debt up to their eyeballs or miserable in myriad other ways. Lots of people fake it till they make it (or don’t make it). It’s foolish to make yourself unhappy by comparing your life, which you know well, to someone else’s facade.

I learned early in the CCAW journey to focus on what was right for my company and me. I acknowledged that my background and circumstances were different than those of my peers. Some things I would never do, or I’d do them at a slower pace. And that was OK. I supported and congratulated my peers on their accomplishments. I tried to focus on our successes instead of dwell on the things we hadn’t accomplished. Life is better when you see the glass as half full.

Comparisons are bad for your mental health. Unfortunately, many people compare themselves to others at some point. If you find yourself falling into that trap, give yourself credit for your accomplishments and recall Teddy Roosevelt’s wisdom: “Comparison is the thief of joy.”

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