Today marked the end of my eighteenth week of working from home. Here are my takeaways from week eighteen:

• Mental wellness – I’ve noticed that more people are discussing the pandemic’s impact on their mental state. Talking about this openly is a good thing. It’s encouraging to people who are struggling to know they’re not alone. I myself have had days when I struggled. I hope that we continue to discuss this topic at work and at home.
• Little wins – I really wanted a small win to celebrate, and I found one. A few weeks ago, I downloaded a new software tool. It’s extremely complicated and intimidating, so I never started using it. My goal was to use it daily. I accomplished that this week, which was encouraging. I plan to learn more about the tool so that I can take full advantage of everything it offers. This little win was a good way to end the week on a high note.
• Zoom – I like Zoom, but I find myself needing to schedule a break from it. Using it a lot in a day strains my eyes and leaves me mentally drained.  

Week eighteen was positive and pretty normal. No major takeaways this week. In two weeks, I’ll reach the five-month mark.

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

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!

Yesterday I listened to a podcast on which Bill Gurley was interviewed. Bill is a partner at Benchmark, a highly regarded West Coast venture capital firm that made early investments in companies like eBay, Uber, Instagram, Zillow, and Snapchat. It’s in the top tier of U.S. venture firms because of its outsize returns to investors.

Bill has been a technology investor for many years. He experienced the dot-com bust and the financial crisis. On the podcast, he shared what he learned from previous downturns: “the best way to protect against the downside is to enjoy every last bit of the upside.” I was surprised. To summarize his explanation, he said that the biggest returns usually come from investments made at the very end of a cycle. If you pull back too early because you’re anticipating a downturn, you’ll miss the best investment opportunities. He didn’t say this, but I assume he thinks that timing a downturn is nearly impossible so people should stay the course until the downturn happens.

Bill is embracing the current reality. He’s accepting his situation and investing accordingly until trends turn and there’s a new reality.

I’ve thought about this and debated with others it over the last day, and I think Bill makes a good argument. Accepting (rather than fighting) a trend positions you to take advantage of whatever opportunities it presents. So what if you don’t like the trend? The trend doesn’t care. If you fight it because you think it’s wrong, you don’t understand it, or you think it will (should) change, you’ll miss out.

This isn’t applicable to everyone or to all situations, but it’s an interesting perspective and food for thought from a wise and experienced investor.

Last year I observed something about small and medium-sized businesses (SMBs) that got me thinking. Consumers communicate with each other differently than they do with SMBs. They text, FaceTime, and direct message via Instagram, Twitter, and many others all day long. Yet they call, email, or physically visit SMBs. Thinking this was a problem, I did some research. What I learned was that it wasn’t a problem. Customers weren’t asking for different communication methods and SMBs were growing, so they didn’t need to change. In hindsight, it might have been a timing thing. I might have been too early.

The world is different now. Consumers are hesitant to visit physical locations. They’re stuck at home trying to work, watch their kids, and do a host of other things. They’re adapting to a different way of living and searching for new ways to safely satisfy their needs and desires. This changing landscape has caused many SMBs to lose customers. They’re trying to offer the same products and services they always have in ways consumers are comfortable with, but they’re struggling to connect with consumers in this new world. SMBs are facing serious challenges and a massive shift in consumer behavior.

I see an opportunity in the midst of this turmoil. What about a platform through which an SMB and its customers could communicate in ways that resonate more with consumers now? Convenient, effective communication would attract customers. What if you could text the grocery store a picture of the orange juice you want to add to your delivery order? What if you could receive a 10-second video from the UPS driver showing where he put your package? What if you could talk to Alexa or Siri to place a dinner order for delivery?

I’m not sure how difficult it would be to build this platform or how it would work. But I think there’s an opportunity to improve how SMBs communicate with customers. Wouldn’t it be nice to rebuild the connection that’s been taken away?

I’ve been working with an entrepreneur for two months. She’s a developer with an app idea who could never find time to create an MVP to test her idea. We settled on a weekly cadence: she would email a group of advisors about her progress and ask for assistance if she needed it. The plan was simple but gave her the encouragement and accountability she needed to execute on her idea.

All was well for the first six weeks. In week seven, the pandemic affected her personally. She wasn’t able to focus and stopped sending the updates. She had stopped working on her app altogether. This was a huge red flag to me.

After hearing about everything she was juggling and her desire to make the app a reality, I made a recommendation: focus on one thing you can accomplish in a day or two. It doesn’t matter how small it is—it can be anything that moves you closer to your goal. Repeat every few days. The idea was that she could continue making progress while dealing with other responsibilities, and she’d have wins she could celebrate.

Sometimes even the best plans go awry. Life happens. It’s just the way the world works. At CCAW, there were many times when I felt like everything was going wrong at once. It was paralyzing and discouraging. Over time, I learned a few things:

• Focus on what you can control. Don’t dwell on things outside your control.
• Figure out how to keep making some kind of progress in small chunks. Celebrating small wins can change your perspective and give you a much-needed spark.
• Talk to credible people about what you’re experiencing. Keeping your feelings bottled up isn’t healthy. You’ll find that other people have been through similar things and can convince you there’s light at the end of the tunnel.
• No success story is up and to the right all the time. There’s always a period of struggle. This too shall pass.

The next time life prevents you from accomplishing your goals, find one small thing you can do quickly. And do it again in a day or two. Small wins will help you weather the storm!

Lately I’ve been looking for ways to have more efficient meetings. Especially with new entrepreneurs. I’m spending half our time trying to understand what problem they’re solving and how their product or service solves it.

At CCAW, I held weekly one-on-one meetings with direct reports. My days were full, so I kept them to a strict 30 minutes. I spent most of that time peeling back layers and asking questions that would get the other person to reflect on what they wanted to talk about. That meant that the meeting was almost over before I understood what we should be talking about. In the end, the meetings were of little value.

Over time, I started using software to help. The day before each meeting, the software prompted my direct reports to answer these questions:

1. What have you accomplished since the last time we met?
2. What roadblocks have you encountered since we last met?
3. What do you plan to accomplish before our next meeting?
4. What are you most worried about today?

If they didn’t answer them, we wouldn’t meet.

This was powerful. Their preparation made our meetings more effective. They could see their previous responses, including what they’d committed to being responsible for. Formulating their answers required reflection and planning and instilled accountability. All of this made our meetings richer.

My own preparation was equally as helpful. I reviewed the answers beforehand. I compared actual accomplishments to planned accomplishments and made a point of discussing gaps. I set expectations and helped my people prioritize. I learned about challenges early and was usually able to address them before they turned into bigger issues. I went into each meeting ready to discuss the things that mattered most to that person and to CCAW’s objectives. The tone of my meetings changed, and people looked forward to them.

Consider preparing for your meetings more effectively and asking or requiring (depending on the context) the other person to do so too. Your meetings will be more productive and helpful.

Last Friday marked the end of my seventeenth week of working from home. Here are my takeaways from week seventeen:

• Path forward – I had good conversations about the future. I’m far from the only person thinking about what the rest of 2020 and 2021 will look like. People are mulling over how they can achieve their goals in creative ways given the pandemic.
• New companies – Lately I’ve spoken with many entrepreneurs who are working on starting businesses. I predict a surge of new companies in the next twelve to twenty-four months. Some of them will have a big impact on society. There are so many needs not being satisfied right now. The masses are actively seeking out new things to adopt—what a rare opportunity for entrepreneurs.
• Redistribution – The pandemic’s impact on commerce is uneven. Some sectors are thriving and having their best year ever. Others are struggling and businesses may shutter. A redistribution may be ongoing.

Week seventeen was a positive week. I paid attention to trends and stopped projecting what I think should be happening. I also thought more about how to move forward if the current situation is the new normal.  

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

I’ve always been in the habit of asking myself a question: am I doing what I need to be doing? Lately, I’ve struggled to answer it. I usually compare what I’m doing today to what’s worked for me in the past. In recent months, I’ve compared what I’m doing today to what I did before COVID-19. I lifted weights four or five days a week to release stress and stay healthy. I traveled by plane every few weeks to maintain existing relationships and build new ones. I went to the office every day to focus on work. I ate out often because I was busy.

When the past is my baseline, the answer is no, I’m not doing what I need to be doing. It’s not that I don’t want to do these activities. I do, but I’m just not comfortable doing them in this environment. That got me thinking about my approach. Should the past be my baseline?

The world has changed so much over the last few months. Many things that were commonplace aren’t viable today. I decided that using a comparison that isn’t feasible doesn’t make sense. In fact, I think it’s unhealthy.

I’ve started to ask myself a different question: am I doing what I need to be doing in the current environment? I no longer use the past as a baseline. What matters is whether I’m getting what I need in the best way possible given the current reality. For example, I need to relieve stress and stay healthy. I’m not comfortable going to the gym, so weightlifting is out. Instead, I’m running outside. Well, it rains pretty often, so I don’t consistently run four or five days a week. Two or three days is more realistic. Since I’m not as active, I now eat home-cooked meals to keep calories down (take-out is full of them!).

Is running two or three days a week what I’m used to? No. Does it give me the same results as my old workout? No. Are running and eating home-cooked meals what I need to be doing now to stay healthy and relieve stress? Yes.

I realized that benchmarking my life against the past was doing myself a disservice. I couldn’t fully embrace the present—which, after all, is all I’ve got—because a part of me was always holding on to the past.

Next time you’re grading yourself, consider thinking about what you need now, in today’s circumstances. You may realize you’ve been shortchanging yourself.

Last Friday marked the end of my sixteenth week of working from home. Here are my takeaways from week sixteen:

• Month four – Hard to believe it’s been four months. If someone had told me I’d spend four months working from home and a few weeks completely locked down, I would’ve thought they were nuts. This has been an extreme exercise in human adaptability. We don’t like change, but we can deal with it when we must—no matter how drastic it is.
• Holidays – Spending holidays with friends and family is what I miss most. Time away from work just doesn’t feel the same when you can’t enjoy it with the people who matter most.
• Reflection – We’re halfway through 2020 and it’s been a crazy year. The second half of the year will be more of the same, if not worse. There’s been so much change in a short time. I hope there’s a light at the end of this tunnel.

Week sixteen was a good week. I’m glad it ended in a holiday weekend. That gave me time to reflect on the last four months and think about the rest of 2020. I don’t believe that pre-COVID-19 “normal life” will return. Getting back to it doesn’t seem realistic anymore. I also don’t think society will tolerate another lockdown; too many are resisting the very thought. In my opinion, something between those two extremes is likely. I think our current reality is our “new normal.” The longer we live in this “new normal,” the more society will accept it and learn to operate within it.

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

I met with an entrepreneur who is building a platform to help artists master and engineer their tracks. Automation will reduce their production time and costs so they can release more music. The platform leverages data science to make the automation possible.

I was intrigued as he explained the problem facing artists and how his platform will address it. I enjoy music as a consumer but have zero experience in the creative or business side of the industry. I have a high-level understanding of data science but zero experience applying it. I would have never thought to put the two together to solve a problem.

This entrepreneur has experience in both areas, which is rare. He’s been a musician since childhood. He’s passionate about it and has over a decade of learning under his belt. He’s worked in data science roles at start-ups alongside PhDs in data science. That experience taught him the power and capabilities of data science. His passion and experience allowed him to recognize how seemingly unrelated disciplines could be combined to create something wonderful.

This entrepreneur is in a great position. His experience puts him ahead of anyone else who has a similar idea; he’ll be able to move much faster. His passion will motivate him and push the platform to the finish line. The two together give him an unfair advantage that greatly increases his chances of success.

If you’re thinking about entrepreneurship, consider: What are you passionate about? What do you have experience doing? Can you put the two together? Identifying your unfair advantage could put you on a path to great success!