Today I met, virtually, a rising entrepreneur. The pandemic has negatively affected Sarah’s company, but it’s also presented her with an opportunity: programming created specifically for a niche audience and delivered OTT. She’s working on this idea and asked for advice on her operational plan. She wants to have her ducks in a row and be able to answer every question her team members might ask her.

Sarah hasn’t yet turned this idea into a product. She needs to secure a small amount of funding before she can afford to pay her team to build the MVP. Like most entrepreneurs at this early stage, she has tons of ideas and a lengthening to-do list. As we talked, I realized that Sarah is focused on the wrong things. She’s working on tasks that won’t help her turn her idea into a product. It’s too early for an operational plan—there is no product and therefore no operation.

This is a common challenge early in the entrepreneurial journey. I was guilty of it and so were many of my successful peers. Entrepreneurs hear about many random things they should be doing to “make it.” They usually pick the things that resonate with them or worry them the most and start working. They don’t know about these important concepts:

• The entrepreneurial journey is made up of sequential segments.
• You usually need to make it through one segment before working on the next.
• The work of each segment comprises different tasks.
• What you’re working on should relate to the segment you’re in.
• Your time and energy are limited. Train them on what matters most. Ignore the rest . . . for now.

Sarah and I talked about what she should focus on to progress from where she is—the idea segment—to the MVP segment. She clicked off with actionable things to do and she’s shelving others that won’t move her closer to an MVP. I’m excited for her and can’t wait to see her MVP in the hands of users.

Focus is important when you’re trying to do the impossible. Especially when it’s your first rodeo. When you’re trying to accomplish something big, focus on what you need to do right now to move to the next stage. Before you know it, you’ll look up and have accomplished something great!

When I started CCAW, I left a pretty comfortable corporate job. I spent four years getting a degree, worked every summer as an intern, and did tons of networking. All so I could land a “prestigious” job at EY. Not only did I quit that job, I did it with impeccable timing. I quit in the midst of the financial crisis.

When people hear that story, they assume I have extremely high risk tolerance. I don’t. I’m wired to have little tolerance for risk. I think in terms of logic, facts, and probability. So how does a guy with low risk tolerance quit his great job to start a company during a recession?

Easy . . . I saw a clear path. I understood the needs of automotive consumers and the struggles of parts distributors and manufacturers. I figured I could solve all their problems by connecting them. I tested my thesis while I still had a day job. I eventually figured out how to convince people to give me money. I didn’t know it at the time, but I’d loosely found product–market fit. With paying customers, I thought my chances of success were pretty good. I saw quitting as a low-risk decision (everybody else thought I was crazy).

I now think of risk tolerance as being natural or adaptive. By nature, I’m risk averse. But my experiences (both successes and failures) have made me comfortable with embracing more risk. My adaptive risk tolerance is medium in most situations and high in areas where I’m experienced. I still don’t bet the house on a single decision and I try to use guardrails where appropriate. One thing that helped me get to this point is recognizing that succeed or fail, what I learn from any experience will be immensely valuable. I accept that it will be painful to learn some things—painful, but valuable. That knowledge sets me up for eventual success, which happens only if I continue to take risks.

I guess the old saying is true. No risk, no reward.

The next time you’re skittish about doing something risky, consider the value in what you’ll learn. It could be the stepping-stone to breakout success!

As I built CCAW, I wore multiple hats, especially in the early days. It’s part of the entrepreneurial journey and I was fine with it until we reached $5 million or so in annual revenue. As the team and the company’s complexity grew, I began to struggle. It was common to have back-to-back meetings, approve large payments, take calls, and talk to a steady stream of team members who wanted my feedback on an idea. Every day. I was mentally exhausted at the end of most days.

One day when I took time to reflect, I realized what the problem was. Not wearing multiple hats—I was used to that and often enjoyed the variety. The issue was constantly switching between mental modes. One moment I needed to think strategically and high-level. The next moment, tactically about a specific problem. And then back to strategic thinking. I’d often be working on something requiring deep concentrated thought and abruptly stop because someone had a question or I needed to run to a meeting.

Over time, I concluded that I couldn’t keep working that way. I was functioning, but it was wearing on me. I felt like the quality of my work had declined. I decided to address the issue and make a change.

I tried a few approaches that didn’t help much. Eventually I hit on something simple that worked. I realized that lunch was the most consistent part of my day. It also served as a natural mental break and change of scene. So, I segmented my days: before lunch and after lunch.

I could focus better in the morning, so I decided to work on things requiring concentration (strategic planning, presentations, new initiatives, etc.) before lunch. I’d find a quiet space in our co-working building most mornings and work until lunch. Just before lunch I’d join the rest of the team in the office. After lunch I worked in the office on tactical tasks, held meetings, and did everything else.

The difference was like night and day. My days were productive and proactive instead of chaotic and reactive. I was able to make consistent progress on all fronts. Because I wasn’t constantly shifting mentally all day long, I no longer felt mentally exhausted. I was back to enjoying the variety in my work.

I doubt if this approach will work for everyone, but it worked for me. If you’re juggling lots of things, consider: are you managing them proactively or reactively?

Today I discussed product–market fit strategies with a rising entrepreneur and another advisor. The entrepreneur is addressing in a unique way a problem she’s passionate about. The pandemic has disrupted her vision for solving it, though. Today we explored the feasibility of digitizing her solution. She referred to this idea as a “digital first, physical second” approach.

After the meeting, that characterization stuck with me. I thought about it. Before 2020, life was “physical first.” Most people shopped in brick-and-mortar places like malls and grocery stores. Online shopping was growing rapidly, but it was still secondary. People regularly met up with friends and family to socialize. Phone calls and other digital communication methods were common, but only when seeing someone wasn’t feasible. Work meetings often took place face-to-face. Some people even flew regularly to conduct meetings (salespeople and consultants, for example). Tools like Zoom and Google Hangouts existed and were used, but only when travel wouldn’t work. Students went to schools and universities for their education, even though e-learning tools have been around for a decade or so.

The world has been flipped. We’ve moved to a “digital first” society.

Like everyone else, I’m living this every day, so it shouldn’t have been a surprise. But hearing it expressed so simply and clearly opened my eyes. I now recognize how big a change we’ve made in a short time. This change has had an enormous impact and will reverberate through our society for the foreseeable future.

As entrepreneurs look to solve old problems in new ways, they should consider embracing a digital-first approach.

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Yesterday I had a great conversation with a fellow entrepreneur. One thing we talked about was sick leave and employee wellness. The Families First Coronavirus Response Act mandates employer-provided benefits through the end of 2020 for COVID-19–related sick and childcare leave, but there is a strong possibility that a more comprehensive approach will be needed going forward.

Employees in jobs that can’t be performed remotely are facing a challenge. Sick leave historically meant taking a few days off. Common colds, sore throats, and coughs were common in most workplaces. If someone did take time off for a serious illness, it was usually for just a few days. Now, these and other symptoms could be leading indicators of COVID-19.

Companies are complying with the Act and have temporarily modified leave policies. People can receive paid time off to quarantine, provide childcare, and recover from COVID-19 symptoms, among other things. Like the Family and Medical Leave Act, the Act doesn’t apply to businesses with fewer than fifty employees in certain circumstances.

I’m wondering if this is the time to rethink how we as a society approach work. Is forty hours a week ideal for full-time workers? Does the standard 9:00 to 5:00 workday make sense? Do we need to rethink sick leave from a public health perspective? Can we do more to support parents who need childcare? You get the idea.

I don’t have the answers and I’m not well versed in the details of employment law. But the pandemic is playing havoc with the world of work and it seems like a good time to discuss these broad issues. Maybe it’s worth rethinking the status quo.

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.