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!

Today I had an interesting conversation that opened my eyes to a new problem. I was speaking with an entrepreneur who understands transportation better than most. It’s evolving rapidly. I’ll use myself as an example. I used to drive to work every morning like everyone else. And I’d drive on weekends and evenings to check things off my to-do list. Then, a few years ago, I began walking or riding a scooter to work. On weekends I’d use Uber to meet friends. I’d drive to run errands only if I couldn’t walk or take a scooter. My car became only one of many viable transportation options.

As the use of scooters and car sharing surged, infrastructure (roads, sidewalks, street signs, etc.) and planning didn’t change much. Scooter riders had to choose between sharing roads with cars and sharing sidewalks with pedestrians. In fairness, lanes were added in some parts of Atlanta, but not broadly. And it became common for traffic to be held up as Uber or Lyft customers began or ended their rides. Places like the airport and malls made changes but, again, changes weren’t evenly adopted.

As the disconnect between transportation and infrastructure was explained to me, I was amazed. There’s a huge opportunity to bring them back into alignment. Doing so—correctly—could change how we commute forever. Changing physical infrastructure isn’t the likely path—using software and other tools to rethink how we use infrastructure is.

The pandemic has inserted an additional variable into this problem, which isn’t yet fully understood. I believe transportation will change as a result of the pandemic, but I don’t think transportation and infrastructure will be brought back into sync. The pandemic will only increase the disconnect.

The entrepreneur I was speaking with today has a great handle on this problem and a creative solution in mind. I can’t wait to see it in action and find out what effect it will have on transportation.

Today I had a great conversation with an entrepreneur about training. He noticed while working in corporate America that retention is a big problem. Companies spend tons of money educating their employees. They want to introduce the latest and greatest thinking to help their teams be the best they can be. Unfortunately, the employees don’t have time to apply what they’ve learned. More than 90% of knowledge is lost because it isn’t revisited promptly.

I’ve personally experienced this many times. I attend a conference, read an article, or watch something online. The information is great, so I’m excited and can’t wait to put it to use. Then I get back to everyday life. The materials stay bookmarked on my computer or filed in a binder. Usually, I never look at either.

Retention isn’t a new problem, but I think it will become more top of mind for company leaders. With so many people working independently from home, I think companies will be rethinking not only how to promote retention of training but also how to deliver it effectively.

The entrepreneur I talked with has a great idea for a solution and I’m eager to see the customer feedback once he launches an early version of his product.  

Steve Jobs was a great entrepreneur who made a huge impact on society. He changed human communication globally and ushered in a new technological wave. People often refer to his reality distortion field (RDF) when describing his work style and discussing why he was able to achieve such great success. Steve had vision and translated it into successful products. He did what most entrepreneurs aim to do, but at a larger-than-life level.

Entrepreneurs are innovators. Part of innovating is figuring out how to make the impossible possible and convincing others to believe. In some instances it works out. In others it doesn’t. When it works out it’s joyous and amazing. When it doesn’t, it can be crushing, and this is when  it’s more important than ever for entrepreneurs to step up. The team needs it.

I’m not Steve Jobs, but I’ve had my RDF moments. I had a vision for my company, but there were huge obstacles. I convinced our team we could figure out how to push through them. I give them credit for believing and supporting me. Unfortunately, some of those obstacles were insurmountable and we failed. I failed because I underestimated the challenge.

Acknowledging these failures and taking ownership as the leader were some of my biggest learning moments. It was painful and something I hated doing, but I did it anyway. I didn’t realize it at the time, but this was invaluable. By acknowledging my shortcomings, I showed the team that it was OK to not be right all the time. I noticed that when I opened up about what I missed or got wrong, others chimed in with what they’d learned from the experience. It started a reflective team conversation. I view reflection as critical to gaining wisdom.

I also apologized for my shortcomings. My team put so much into these efforts that it was devastating when they didn’t pan out. The apology acknowledged their efforts but also helped us move past the experience as a team. Apologies are simple, but they can be powerful. They can quickly remove the tension from situations.

If you’re working with others on something and it doesn’t go well, consider acknowledging your part in the failure. It’s likely to be painful but also an amazing growth and bonding opportunity!

Adapting has been top of mind for me during the last few months. The world has experienced monumental change in a short time. I’m constantly thinking about how I should adjust to my current reality.

During a conversation last week, Tom shared a professional realization. He has long believed that great partnerships lead to success in his line of work. Therefore, identifying great partners is crucial. He has always established relationships with and evaluated potential partners through in-person interaction. That approach served him well for over a decade. He had a lot of success working with some great people he got to know face to face. Relationships are still key in his world, but in-person dealings aren’t an option anymore. He has to find partners in a new way. He’s actively looking for ways to identify and evaluate partners virtually.

As I reflected on the conversation, a few things jumped out at me. John’s former approach was highly effective but also highly restrictive. He was limited by geographic boundaries. Sure, he could travel and whatnot, but there’s a realistic limit to how often and how far he would travel. I’d imagine there are lots of great people he never considered over the years because they weren’t near him.  

The pandemic has upended life as we knew it, but humans are adaptable and I think it could lead to many amazing things. One in particular strikes me at the moment: opportunities may no longer be geographically constrained. Learning to build relationships, evaluate others, and collaborate virtually could be a game changer. Eliminating spatial boundaries could help spread opportunity more evenly. Qualified people at a geographic disadvantage could have an equal chance to get in the game. The ripple effects could be huge, reshaping our workforce and the economy.

We’re in the early phases of adapting. Lots of questions still must be answered. But the more I think about the potential of virtual work to remove boundaries, the more excited I get. This is a difficult time for everyone, but it could result in seismic change that has a long-lasting positive affect on society.

Today marked the end of my twenty-third week of working from home (mostly). Here are my takeaways from week twenty-three:

• Eye strain – This week I had a record number of video meetings, including one that lasted four hours. My eyes feel a bit strained, which probably isn’t good. I’ll avoid screens this weekend (as much as possible).
• Virtual showcase – I attended my first event in a virtual venue: Square One Startup School’s Startup Showcase. The organizers had arranged networking via one-on-one conversations, a DJ, and even exhibition booths. I was impressed and would attend another one of these.  
• Pace – This week was another busy one. I’m looking forward to returning to a more normal pace next week. (Truly! Yes, I know I said that last week.)
• Large projects – I planned to attack some big projects, but I couldn’t find the concentrated blocks of time it would take. I’ve blocked out chunks of time on my calendar to try to prevent this from happening again.

Week twenty-three was hectic. I didn’t accomplish what I wanted to, which was disappointing. I’m looking forward to having some uninterrupted time to focus next week.    

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

Yesterday a close friend connected me with a new founder. This founder, John, has a background in logistics and wants to apply that knowledge to help businesses in his underserved community. He talked to a few restaurateurs about their specific challenges and figured he could help.

I spent about thirty minutes with John and learned a ton about the opportunity he sees and about him as an entrepreneur. John noticed a few things about restaurateurs in his community. One, many don’t have any online presence. No website. No anything. There are a variety of reasons for this, but lack of familiarity with technology is part of it. Two, they don’t have the ability to accept online orders for pickup. Customers stand in long lines or are stuck on hold when they call in orders. Three, most of these restaurants are looking for a delivery option that better meets their customers’ needs. Four, the pandemic has stoked their desire to find solutions to one, two and three. They need these solutions quickly so they can survive in this new world. But they don’t have the knowledge, relationships, or capital to execute on them quickly.

John figures he can solve some or all of these problems. Now, a few things to take note of. He doesn’t have a technology background, but he knows technology will be key (knowledge gap). He doesn’t have a lot of money (capital gap), so he needs a cost-effective technology solution. He doesn’t know any developers (relationship gap). He was able to find the help he needs via . . . wait for it . . . Google. He connected with technical talent overseas. He described his problem and they suggested an off-the-shelf solution. He is now able to offer the following to every restaurant he targets:

• A website for ordering
• A mobile app for ordering

All for a small amount of capital. Now, the technology isn’t DoorDash or Uber Eats quality, but it’s good enough. He can offer restaurants an online presence with their own mobile app and the ability to offer online ordering for pickup. He used his logistics background to assemble a small team of delivery drivers. Add it all together, and voilà! He created an MVP that solves all three problems he learned about. And he did it all in about a month.

He has signed up a handful of restaurants as customers and is delivering a significant number of orders daily. Every day he’s learning more about his customers and their problems. He’s adjusting his solution based on those learnings.

John is a great example of an entrepreneur looking for a product–market fit. He’s trying to find the ideal solution to his customer’s problems using an MVP he cobbled together quickly. Is the current solution perfect? No. Is it scalable? In the long run, probably not. Is he learning and adjusting quickly? Absolutely. Will his adjustments lead him to a great solution that customers readily pay for? The way he’s going about things makes success more likely.

If you see a problem and have an idea about how to solve it, consider starting with an MVP. It doesn’t have to be perfect or pretty.

During my journey with CCAW, I experienced some extreme highs and lows. There were times when we were on top of the world and had more customers than we could handle. There were other times when we wouldn’t survive unless I figured something out quickly. I know from talking with other entrepreneurs that extremes are a normal part of the journey. Apparently, it’s part of the package deal you get when you sign up for achieving something great.

People often believe that entrepreneurs are different than everyone else. This is (somewhat) true. Where others see a problem, we see an opportunity to fix a problem. When others avoid a situation with a high probability of failure, we grab onto it. Mostly, though, we’re just like everyone else. Entrepreneurs experience the same emotions and have the same thoughts as everyone else. Yes, we motivate our teams to push through adversity. Yes, we believe we can pull a rabbit out of a hat. But we also have the range of emotions you’d expect when things are going better than anticipated or horribly.

My first few years as an entrepreneur, I struggled a bit with this. I felt like I always had to have the answers. I had to be constantly optimistic. I couldn’t express how unsure or worried I was. I couldn’t openly say that I didn’t know what I was doing. Eventually I learned that this wasn’t sustainable or realistic. I was human, so acting like I was a machine just wouldn’t work. Through luck and networking, I found my saving grace: a support system.

Support systems are critical to help entrepreneurs (and everyone else for that matter) keep going through extreme times. Peer groups, family, business coaches, and mentors can all serve as part of your support system. They give you a way to talk through what you’re experiencing and feeling. They help you make sense of things. And really good ones help you come up with a path forward. All of this helps you maintain your mental wellness.

If you’re thinking about doing something great (or are already doing it), consider who could support you during the inevitable highs and lows.

Email has always been a challenge for me to manage. I’ve tried a variety of approaches over the years but never found one I could love. Inbox zero was always my goal, but I never got there. As I’ve embraced messaging through other platforms (Slack, LinkedIn, etc.) and added email accounts, my frustration has intensified. These days I’ve gone beyond annoyed to exasperated enough to seek a solution (and I’ll happily pay for it). I’m not doing anything unique, so I assume others experience this pain too.

With less in-person interaction in the foreseeable future, I think written communication will remain elevated (along with video). Email, Slack, text messages, direct messages, and more . . . they all require the user to manage an inbox inside an application. And the number of applications is growing by the day. I foresee more people struggling to communicate effectively via all these different apps.

Today I had a great conversation with a fellow entrepreneur about this. He feels the same way. Every day, he keeps multiple browser windows and tabs open for all his different inboxes. We dug into the problem more, discussed the shortcomings of existing products, and debated the desire for a solution to this in the market. We have a ton of questions we couldn’t answer but agreed there could be something here.

I don’t know what a solution would look like or how it would work, but I believe there’s a problem waiting to be solved. In my opinion, there’s a real entrepreneurial opportunity to build a sizeable business around the solution to too many inboxes.

In CCAW’s early days I was constantly trying to convince vendors to work with us. They’d never heard of CCAW and I was asking them to do things they weren’t doing for other customers. I sounded like that annoying customer who would be a pain to work with. Many said no, but a few said yes. Often the terms and pricing were unfavorable because I wasn’t in a position to negotiate. The opportunity, though, was worth paying inflated prices.

Over time our spend and reputation with vendors grew. Our use of technology meant that our relationship required minimal interaction. Translation: our account was highly profitable. Vendors loved working with us. We eventually became the largest customer of some of them.

One day I realized that our relationships had evolved from customer–vendor to more of a partnership. We had a unique perspective (and data to support it) on their operations across many states. We also had customer insights nationally. None of their other customers provided these things.

We began to embrace our strengths. We started providing data to our vendors, but we also made an ask. We had been bearing the brunt of their operational mistakes and eating the costs. In our minds it was a cost of doing business. As we scaled, the error percentage stayed the same, but the dollars were material (e.g., an 1% error rate went from a loss of $1,000 to $100,000 annually). We asked them to assume this financial burden. We thought they would say no. After all, it wasn’t something they did for any other customer. To our surprise, they quickly agreed. No negotiation. Just a quick yes. Apparently, the value we brought to the relationship far exceeded the cost of our request.

Healthy relationships are bidirectional. This experience taught me a valuable lesson about managing healthy business relationships. Ask for what you need to receive from the relationship. Good partners will recognize your value and want to reciprocate by saying yes.