Today marks the end of my forty-fourth week of working from home (mostly). Here are my takeaways from week forty-four:

• January – Today was the last business day of the month. January was an eventful month full of extremes. It felt like an extension of 2020 with a twist. I’m curious about whether we’ll continue to see extremes the rest of the year.
• Work from home – I worked exclusively from home this week. It wasn’t terrible—but it wasn’t great, either. A change of scene is important to me and I definitely notice when I don’t get it.  
• Wall Street & Main Street – Developments in the stock market this past week were astonishing. And I think the situation is far from over. In what direction will this saga go? What topics will it put at the forefront of popular culture? I hope it doesn’t lead to a repeat of 2008 and 2009.
• Ideas – Had some great conversations this week about some ideas I’m excited about. Looking forward to working with others to put some of them into action.

Week forty-four was pretty crazy—normal for me personally, but historic and extreme at a macro level.

Over the last few days, we’ve heard about the GameStop Reddit WallStreetBets saga playing out in the stock market. If you’re not familiar with it, you may want to read up on it. It will likely be remembered as a major historical event. The story centers around a Reddit community called WallStreetBets.

I’ve been a fan and user of digital communities since high school, and I’ve shared my thoughts about them in one of my daily posts. Some of these communities have helped me accelerate my learning and navigate unfamiliar situations, including my transition to corporate America and a new city.

What we’re witnessing is how powerful digital communities can be. Let me be clear: I’m not taking a position on current events. What I’m saying is that the fact that a group of ordinary people online can organize a call to action so big that it shakes Wall Street is a testament to the impact digital communities can (and will) have on our lives.

Love them or hate them, the people have spoken and digital communities are here to stay!

I had a great conversation with a good friend today. We talked about traits we’ve noticed in successful entrepreneurs. He shared some insights from his time in entertainment, while mine were from my time and relationships in tech. Interestingly, they overlapped.

• Learners – Successful people are learners. They’re aware of their gaps and actively seeking to fill them. Sometimes that involves taking on a role in someone else’s organization to set themselves up for future success . . . and perhaps more future success via their own vehicle. They set their ego aside to gain the knowledge they need for the future.
• Partnership – They recognize that they can’t do it alone and actively seek to partner with others who can help them succeed. Both bringing the right people inside their organization and partnering with the right outside people can work.
• Accountability – Successful people want to be held accountable and want their teams to be held accountable. They create cultures and put processes in place that reinforce this.

I always enjoy catching up with people in other industries and picking their brains. Today was no different. It reinforced that there are clear patterns and habits that contribute to success!

Today Calendly announced that it raised $350 million and is valued at over $3 billion. I’ve used Calendy since 2015 and am a huge fan. The team is talented and the product makes scheduling a meeting super easy. A few thoughts on this deal:

• Pandemic – The company already had an impressive growth rate, and it increased dramatically during the pandemic. They were well positioned for revenue redistribution.
• Revenue – They’re now at roughly $70 million in annual revenue. So, they’re eyeing $1 billion.
• Profitable – The company is growing rapidly and profitable—a dynamite combination.
• Hot market – The market is still hot. Investors are willing to pay higher valuation multiples for attractive growth opportunities.

Congrats to the Calendly team on a huge win! They’ve been building a great company and product for years. Can’t wait to see what happens next.

When I created CCAW, I decided to go with an asset-light business model. In so doing, I was attaching myself to suppliers and vendors. We relied on them for operational execution and inventory planning. I referred to them as partners because without them our business couldn’t operate. Knowing this, I made a point of having strong relationships with our partners. I assumed that what mattered most to them was the size of our relationship (i.e., our sales with them). I tracked sales with each partner and constantly talked about ways to sell more.

One day I was talking to an executive at one of our partners. I casually asked, “What does a great customer look like to you?” I was trying to find out if we were doing what was needed to be a key customer and be included in some of their strategic decision-making. His answer was not what I expected: “The ones that pay their bills, and on time. You can buy a ton of stuff from me, but if you never pay or pay late I’d rather you never buy from me.”

I learned that we weren’t their biggest customer, but we were a key customer because of our flawless payment history. Constantly buying inventory required lots of capital, and they had challenges with keeping everything in stock and having enough operating capital (this is the exact reason we didn’t want to hold inventory). I made calls to other partners and they all confirmed that they put a high priority on timely payments. I had assumed all companies were like us and paid on time. Wrong. We were operating in a space where people didn’t pay their bills on time.

We had great accounting processes, but I’d never thought of accounting metrics as key to our strategy. That changed. I put our payables process higher on the list of important metrics and made those metrics visible. Payables was now a huge competitive advantage we could use to enhance our growth strategy.

In hindsight, I wish I’d asked for input earlier. I was aiming for what I thought mattered most (sales), only to find out that my partners valued something different (cash flow). When we started to lead conversations with potential partners with what mattered most to them, we signed up more of them and our growth rate increased.

If you’re a founder trying to do something great, you’ll probably need help (from partners or investors, for instance). Early on, ask them what’s important to them. Don’t assume! You’ll gain valuable insights and cement your relationships with stakeholders.

Yesterday I said that benchmarking is one of the mental challenges founders face. Then today I read this:

Anyone you see succeeding is only succeeding at the things you’re paying attention to—I guarantee they are also failing at lots of other things.”

~Ray Dalio

I like this quote because it’s a reminder of why we shouldn’t benchmark ourselves against others. We often don’t have (or aren’t paying attention to) the full picture. Selective comparisons disregard the reality that failure is likely part of their story. The truth is that failure is more common than we like to admit. Even when it seems that someone is wildly successful, they’re probably failing too. And that’s OK.

Benchmarking is a mental trap that’s common among founders (and people in general). And probably more so now, in the Information Age, than ever before. (We can find out a lot about people’s successes on the web and social media—but much less about their failures.)

Try to avoid this trap. Instead of measuring yourself against an incomplete picture of someone else, pay closer attention to your own situation. Give yourself credit for your success and make it a point to not only learn from your failures but apply what you learn to future decisions. This will help you succeed, while benchmarking yourself against others will depress you. That’s not conducive to success!

I was asked to give my input on a program being developed to help diverse Atlanta entrepreneurs. I’m excited about the program and can’t wait for it to launch. The creators asked me a tough question: “What mental challenges do founders face?” The fact that they’re thinking about this and wanting to help founders address these challenges is encouraging.

Here are a few things I shared:

• Release – Founders should understand the one thing they enjoy and need outside of work to be the best version of themselves. It could be exercising, playing video games, attending sporting events or live concerts, or anything else. Whatever your thing is, make it a priority so you’ll have a mental release.
• Imposter syndrome – Founders are constantly in environments and situations where they feel they’re unqualified and unprepared to handle whatever’s going on. They often fear failing or being exposed to others as a fraud. This is normal and usually unfounded. Most people know entrepreneurs have gaps but still root them on. Not because they’re perfect or have all the answers, but because they have the courage to try to do something great.
• Benchmarking – Founders will sometimes compare themselves to their peers. This is a mental trap. Everyone’s circumstances are different. Timing also plays a huge role in success. Just because someone else is succeeding and you aren’t doesn’t mean you won’t ever. Be happy for them and know your time will come.

There are lots of other mental challenges, but these are a few that I think many founders have had to overcome. Entrepreneurship is a mental game. Going into the game knowing what to expect can . . . well, be a game changer. Entrepreneurs will be able to be more proactive than reactive during their journey. I’m excited to hear that diverse founders will get help with the mental side of entrepreneurship!

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

• Optimistic – I’m not sure how 2021 will play out, but I’m optimistic. I’m hopeful that we’ll begin to trend in a positive direction. I know the country’s problems won’t be resolved overnight, but it appears we’re pointing the right way.
• Work from home – I may soon return to working exclusively from home. I’m not excited about this, but it may be the prudent decision.
• Year of change – I’ve had a few conversations with people close to me who are considering making big changes in their lives. This year, 2021, may be a year of change for a lot of people.
• Groove – It’s been hard for me to settle into a good working rhythm since the holidays. I’m hopeful that next week I’ll have my groove back.

Week forty-three was a short week because of the Monday holiday but otherwise pretty normal (well, what passes for normal these days).

Today I met with a successful entrepreneur who recently sold his company. He shared his views on the entrepreneurial journey, which he sees as an evolution. I totally agree. My attention was caught by his term for one stage of the journey: “rebirth.” After you have the idea, build the company, exit the company, and overcome the post-exit phase (i.e., separate yourself and your identity from the company), there’s another phase. He views it as the beginning of a new chapter, which will be different for every person. It’s the “Now what?” phase.

I’ve never heard it articulated this way, but I agree with him. When you’re focused on something for a long period of time and then it’s gone from your life, there’s a time of transition. A time when you think, “Now what?” I think rebirth is a natural part of everyone’s (not just entrepreneurs’) evolving life. Parents whose children have left home. Anyone recently retired. Someone recently laid off. People who are widowed or divorced.

Rebirth can be uncomfortable, even deeply painful depending on the circumstances, but it’s also an opportunity. A chance to steer your efforts in a new direction and grow in a different way.  A renewed existence of sorts. A do-over. Whatever journey you’re on, it won’t end; it will just cycle around.

Time is often called the great equalizer. You can’t buy, sell it, or trade it. Everyone gets the same 24 hours a day. The only thing you can do with time is manage it. As a youth, I was often reminded of this by elders, but it didn’t resonate with me. It wasn’t until I was a founder that I learned how managing time effectively can change your trajectory.

When I was asked recently for my views on this topic, I shared a few habits and tricks I’ve adopted over the years. Here they are:

• Mortality – I use this Chrome extension to remind me how much time I have left to live. It’s a (yes, somewhat morbid) subtle daily reminder to not waste time.
• Weekly reflection – I reflect on the past week in blog posts, numbering these weekly posts so I can keep track of the weeks. I started doing this early in the pandemic to track how many weeks I’d been working from home, and it morphed into a broader reflection. Here’s a recent post.
• Schedule – I try to think about what types of activities I want to work on each workday. I’ve blocked out time for certain things and I use this technique as a guideline and reminder about what I should be focusing on.
• No – I say not to a lot of things to protect my time.
• Time vs. money – When I have the option of paying (a reasonable amount) for something that saves me time, I normally decide to pay. I figure I’m going to pay in time or in money. I can make more money, but not more time. I understand that I’m fortunate to be able to make this choice and that not everyone is. I appreciate my good fortune and don’t take it for granted.

These are some things I’ve learned and adopted over the years. I understand that they won’t work for everyone, and I’d love to hear how others manage their precious time.