Update emails are a great tool for founders. They’re just what the name suggests: emails that highlight important recent information about the company or founder. They’re an electronic way of answering the “What’s new?” question from investors and advisors. When I meet with founders, I usually request that they add me to their update email list.

Here are some ways update emails add value:

• Efficiency – One email communicates your updates to many people . You can’t beat that ROI. Imagine having to bring each person up to speed individually.
• The luck factor – Opportunities tend to be offered to people who are top-of-mind. Sending updates regularly puts you on people’s minds.
• Accountability – Nobody wants to disappoint people they hold in high regard. Knowing that you have to send an update will push you to complete things you’ve committed to in the last one.  
• Help – It’s hard for people to help if they don’t know what you need. Updates bring awareness of your needs to a broad audience. I’ve seen founders receive help from someone on their update email list who was the last person they anticipated would be helpful. You never know what or who someone knows.
• Reflection – Experiences—good or bad—are valuable, and reflecting on them will help you grow and gain wisdom. But it’s all too easy to succumb to the daily whirl and never stop moving long enough to think deeply. Writing an update email forces some degree of regular reflection.
• Team building – People like to know what’s going on outside their area of responsibility, and that can be difficult for founders to communicate. Especially while everyone works from home. And I’ve seen founders benefit from including their teams on their updates. Again, you never know what or who someone knows. Team members can be great resources.

So, what makes update emails successful? Here are a few of my thoughts:

• Consistent rhythm – Send them regularly to stay top of mind. Consistency also helps keep the length down. Cramming six months’ worth of updates into a single email will ensure that few people will read it.
• Consistent structure – Organize and format your update emails the same way every time. This will allow readers to quickly find the info that matters most to them. And they’ll be more likely to read them.  A progress report, future plans, and requests for help are good things to include.
• Conciseness – Get straight to the point. The more concise the update, the better. People will stop reading if you ramble.
• Transparency – Don’t sugarcoat bad news. Include the highs and the lows. Nobody expects perfection from founders. Revealing problems opens the door for others to share the wisdom they gained from similar experiences.

I love it when a good update email lands in my inbox. If you’re thinking about starting a company (or you’ve started one), sending regular update emails is a good practice.  

Over the last few months I’ve heard a number of entrepreneurs express concern for the mental wellness of their team. They’re unsure how working from home is affecting them. Are they sad . . . anxious . . . happy . . . neutral? A few of them began conducting one-on-one video meetings with every team member (not just their direct reports). This is thoughtful, but it won’t scale. If more than 50 or 60 people are on the team, there’s not enough time in the day to meet with them individually.

Understanding employee morale has always been a priority for leaders. In the past they could walk the halls and get a pretty good idea. No more. Gauging the morale of employees who are working from home is a pressing problem.

Today I met with an entrepreneur who’s looking to solve it with software. A few years ago, he realized employers had a retention issue. He predicted that an early understanding of how employees are feeling about things could prevent team turnover. If a manager is aware of an issue early on, it can be addressed before it causes the employee to resign. This entrepreneur has raised some funding from investors and I’ll be excited to see the next version of his product.

The pandemic is challenging everyone, but it’s also creating opportunities for creative entrepreneurs. People still have the same needs, and they’re actively seeking new ways to get them met.

Opportunities like this don’t happen often. If you’re an aspiring entrepreneur, seize the day!

I’ve been asked a few times to name one game-changing thing I did to help myself. Easy question: I sought out people MUCH smarter than I who were directionally aligned with me. This changed my trajectory, and it’s something most people can do.

Directional alignment was key, and it required me to think about where I want to be in 10, 15, and 20 years. I didn’t get granular and say I want to be at X place by Y date; I kept it high-level. When I was thinking of leaving corporate America, I decided I wanted to build a company and be an entrepreneur. I didn’t want to be shady or exploitative. I wanted to be successful while treating others the way I wanted to be treated. Super high-level; clear direction.

Once I knew where I was headed, I looked for groups of people smarter than I was. Some, like EO, were formal. Others were informal. I’ll admit this was tough to do. I was very uncomfortable when I first interacted with these groups. I was used to being at the top of my game. I’d done well in school and ranked high among my peers in the corporate world. I soon learned how big my knowledge gap was!

I was inexperienced and embarrassed when I couldn’t answer questions about topics that were basic in these circles. I often had no idea what they were talking about and experienced imposter syndrome. I powered through it, though. I noted things I was unfamiliar with and Googled them later. I had one-off conversations with people to dive deeper into specific topics. I eventually realized that when I was uncomfortable, it meant I was learning. Over time I became comfortable being uncomfortable.

Smart people introduced me to many new things and better ways of doing old things. Over time, I formed great relationships with many of them. Looking back, I see how critical my decision was. These groups helped fill my knowledge and relationship gaps, which gave me more opportunities to be successful.

One thing I didn’t do well early in my career was recognize greatness quickly. Someone close to me had to point it out (much later, typically). People . . . opportunities . . . accomplishments—it didn’t matter. For whatever reason, I wouldn’t see it as soon as other people did. And when I did, sometimes it was too late.

During my journey building CCAW, I realized that I didn’t recognize greatness quickly. I didn’t like this about myself and decided to change it. My knowledge gap was my first issue. I tackled it by reading widely in areas I deemed important personally and professionally. This gave me a baseline. When something was superior to that baseline, I could readily identify its greatness. My personality was another obstacle. I tend to be laid back and have blind spots when it comes to people. I can’t change how I’m wired, so this was more challenging to solve. I learned to ask the opinions of colleagues or friends who deeply understand people when I encountered someone I wasn’t sure about. Their observations helped me recognize when the person was great. Not the most scientific approach, but it works for me.

Not being able to recognize greatness hindered me in a few ways. It slowed my decision making, so I missed out on some great opportunities. And I didn’t allocate the appropriate time and resources to great people and opportunities.

Times change. Today I had a conversation with a buddy about an investment I made that has done well. He asked how I knew the company would succeed before other people did. I told him that I quickly recognized its uniqueness because I’ve seen lots of companies in the space and done lots of reading about the space. This company’s performance was rare when I baselined it against what I usually see. I believed this company was great and invested in it confidently.

Some opportunities really do come along only once in a lifetime. Learning to know them when you seem them can be life changing!

Today a friend reached out and offered a suggestion. He’s watched me share more over the last few months and had an idea. He sent me a text about it and we hopped on the phone. The suggestion was a small tweak that would expose my content to more people. I had no idea it was possible. I thanked him and asked if he had seen anything else I could do better, and he made more suggestions. All of them were great.

I reflected after the call. In ten minutes, he told me things that would have taken me weeks to figure out. What a huge amount of time saved! I just had to open my mind and be receptive to someone pointing out an area I could improve in.

Early in my entrepreneurial journey I was overconfident. People would make suggestions, but I wouldn’t heed them. If I had a vision for something and a suggestion didn’t mesh with it, I wouldn’t take it seriously. Instead of listening to what the person was saying, I would fixate on their not buying into my vision. Often, I learned the hard way. Eventually I’d do what they had suggested, but only after my vision had failed. Over time, I learned to appreciate credible people and listen when they make suggestions.

My friend is a very credible entrepreneur and respected in his field, so I was receptive when he reached out. In fact, I was excited to be critiqued by him and hear his perspective. Sure, he pointed out things I wasn’t doing well. But more importantly he showed me a better way and explained why it was a better way. I thanked him for taking the time to contact me and implemented the change while we were on the phone. I wanted him to know that I took his suggestions seriously.

The next time someone credible offers to critique your work, jump at the chance and listen to them. If such offers aren’t coming your way, consider asking someone credible to critique your work. You could save yourself a lot of time and energy and learn things you might not have otherwise!

I recently spoke with a friend who happens to be an entrepreneur. One of his businesses is in commercial real estate. We talked about my journey with CCAW and how my real estate needs evolved. When I started CCAW, it was a small desk in the corner of my apartment. I worked from home for about three years. When I expanded the team, I sublet space from a much larger company for a few years. Next we moved to coworking space at Atlanta Tech Village.

My friend thought about all the rent I’d paid over the years and couldn’t understand why I hadn’t bought a building. In fact, I considered purchasing a commercial space and drove around many times looking for the perfect place. Each time I decided against pulling the trigger. Here’s some my reasoning:

• Community – We had a very small team, so creating a sense of community was difficult. Subleased and coworking space provided instant community, which was a huge plus in recruiting. Learning events, socials, friend groups, etc. boosted team morale. People liked coming to work.
• Flexibility – I couldn’t predict the future. Being in a space that could accommodate change was appealing. We grew and contracted many times over the years. Not owning space helped minimize the stress of those periods.
• Location – I couldn’t afford a building in a nice part of town. Subleasing and coworking allowed CCAW to be located in a desirable, walkable area. This was a huge plus during recruiting and visits from vendors.
• Amenities – Being in a space used by many companies allowed for amenities we could never have afforded if I had bought a building. A gym, a rooftop deck: density made them possible.
• Facilities – We didn’t have to worry about maintenance or upkeep because building management handled everything. Owning a space would have introduced a set of issues that I wasn’t interested in.
• Serendipity – Working alongside other companies made regular chance encounters possible. This may seem insignificant, but some of our luckiest breaks came from those encounters. Owning would have eliminated any chance of such luck.
• Founder relationships – I built solid relationships with other founders who worked in the same space, often through random interactions. Over the years, these relationships have helped me navigate challenging times and have turned into friendships. Owning would have made this many times more difficult.

Could I have paid a lot less per square foot by owning? Yup. Could I have built equity in a real estate asset? Absolutely. Looking back, do I wish I’d bought? Not a chance.

My criteria weren’t based on cost. They were based on value. I regularly asked myself if the value CCAW received from not owning exceeded the cost. The answer was always yes. In the end, the way most things are priced ensures that you get what you pay for.

Next time you’re considering a purchase, ask yourself if the value will exceed the cost.

Today I had a conversation with a fellow entrepreneur that blew me away. We started our companies around the same time, so our paths have crossed in Atlanta’s startup community over the years. Recently we’ve gotten to know each other better and have discussed how to improve the ecosystem for future entrepreneurs.

Today, we each talked about our background and our entrepreneurial journey. We wanted to help each other understand how our experiences shaped us and how they fuel our passion to help others. As we talked, we realized that we’re connected not only as entrepreneurs but also in various ways on a very personal level. We have close personal relationships with people who in turn have close personal relationships with each other.

Honestly, I was surprised. I didn’t anticipate the deep level of personal connectedness we uncovered. I had no idea we knew the same people. I’m thankful for the conversation. It allowed us to connect in a different way and develop a deep understanding of each other. I anticipate that it will prove to be the foundation of a great relationship.

Relationships are central to entrepreneurship (and, more broadly, to life). Entrepreneurs continually build relationships as we participate in various unrelated groups. Across many years, paths will cross. Inevitably, relationships will bleed over from one group to another and between business and our personal lives.

Relationships make the world go ’round—and the world is much smaller than we realize. Be mindful of this, entrepreneurs, in all your endeavors.

Accomplishing anything significant usually requires a team. Sure, one person may be able to do it, but it will be many times harder and take much longer. The thing that makes teams so special is their synergy. Teams comprising members whose strengths and weaknesses are complementary in important areas are strong and may make the difference between the business succeeding or failing.

Not embracing this fact—or, for that matter, even knowing it—hindered me at various points in CCAW’s journey. You’d think I would have learned my lesson, but I didn’t. I didn’t know any better and didn’t have people pointing out this oversight until late in the journey. It was a huge knowledge gap.

Early on I had an idea, but I didn’t know if it would work. I focused on testing and figuring everything out myself. The end result was good: I got a product/market fit. But it took much longer than it should have. Like, years longer. I missed out on first-mover advantage in our space. We played catch-up while key vendors benchmarked us against a competitor.

Years later, we were at around $7 or $8 million in annual revenue. We had developed a reputation for being well run and fair to customers and vendors. We reached a point where a comprehensive go-to-market strategy was needed to get to my $100 million goal. How should we market to customers and installers? How could we most effectively partner with suppliers and manufacturers? How could we acquire customers cost-efficiently and predictably? All extremely important questions! I didn’t have experience in these areas, nor did anyone on the team. I tried to find people to bring on board, but I didn’t make it a top priority. So, we had a huge weakness in a critical area because I didn’t add the right people. We never hit the $100 million goal.

Creating a vision for CCAW was important. Honestly, It took me years to figure it out—much longer than it should have. Operating in our space was difficult because it was constantly shifting. My big mistake was in not thinking deeply about the skills required to achieve my vision and making it a priority to add people who had them to our team.

If you’re thinking of accomplishing something significant (personal or professional), consider what skills are needed to make your vision reality. Then figure out who has the skills you lack. Answering these questions could put you on the path to greatness with a great team.  

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.

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.