Over the last year, I’ve been more intentional about giving back to rising entrepreneurs. I try to help fill their knowledge and relationship gaps. I share my experiences and connect them with other people who can help. I remember how difficult the early segment of the journey was for me. Help was pivotal. I’m not sure that I would have progressed to the next segment without it.

One thing I’ve noticed in my mentoring and advising caught me off guard. Some early entrepreneurs don’t ask for help. When connected with people who want to help, they never make contact. I’m not the only one who’s noticed this. I’ve spoken with program managers at accelerators focused exclusively on helping early stage founders who’ve noticed a similar pattern.

I decided to think about the early stages of my own entrepreneurial journey. I was curious about whether I was guilty of the same behavior. I dug through old materials and correspondence and sure enough, I was! I didn’t ask for help after meeting people, or I took much longer to do so than I should have.

I think there are a variety of explanations. Bandwidth is the first. Early-stage founders are wearing ten hats and just don’t get around to everything. Imposter syndrome is the second. I was inexperienced. I felt embarrassed about asking certain questions. I was afraid people would realize how much I didn’t know or how little traction I’d made. I eventually got over this, which changed my life.

Founders should never feel ashamed to ask for help. It doesn’t matter how silly they fear their questions are. Anyone who’s made the journey and is offering to help knows better than to judge. After all, they were in the same place back in the day.

People with experience who want to help are a great resource that founders should take full advantage of. So many don’t ask for help that when you do, you stand out. In a good way. It shows that you’re willing to take action.

The next time you’re introduced to someone with experience who you have reason to believe wants to help, ignore that little voice in your head that urges caution (it’s the voice of fear). Ask them to help you with your most pressing obstacle. They’ll probably be glad you asked and delighted to help!

When I read biographies of people who’ve had an impact on society, I’m always amazed. Their journeys were full of extreme highs and lows that most people aren’t aware of. Somehow, they hung on through the tough times and accomplished something great. The ability to do that is rare, and it stands out. I characterize it as perseverance, and I think the relatively few people who make it big all have it.

The early days of building CCAW were tough. I had no help, the financial crisis was full blown, and there was so much I didn’t know. There were stretches where everything would go wrong. No matter what I did, things blew up in my face. I believed in what I was trying to do, but I’m only human. It became more difficult to keep pushing through failures. When I struggled, I’d try to take a pause to clear my head. The gym was usually my escape. I’d blow off steam there and think about things unrelated to work. It was a mental reset of sorts. The next day I’d get back to work with a fresh mind. That helped.

In my opinion, perseverance isn’t a common trait. Failure hurts, and most people don’t want to experience that pain repeatedly. I think that’s why most people don’t carry on through tough times and keep going. When they fail, they regroup and avoid paths that could end in more failure.

I’m thankful that I pushed through some of my early pain at CCAW. With the help of others, I went on to accomplish some great things and learn more about myself than I have from any other experience in my life. It wasn’t always fun, but I’m glad I didn’t give up.

The next time you face a setback and aren’t sure how to proceed, remember that perseverance precedes greatness!

Today marked the end of my nineteenth week of working from home. Here are my takeaways from week nineteen:

• Month five – It’s been almost five months. This experience has been surreal and there’s no end in sight. Looks like I’ll be working from home for many more months. I won’t be surprised if I’m still doing it next year.
• Focus – A unique opportunity came up this week. I chose to focus on it and forego making progress in other areas. I’m glad I did. But next week, I’ll try a more balanced approach.
• Communication – I use Zoom and email every day, but I’m starting to wonder if there are other communication methods that would also be effective. I’ll do some research on this over the next few weeks.  

Week nineteen was a good week. No major takeaways.

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

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.

‍

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.

A few years ago, I sold an extra vehicle. I’ve been a passionate car enthusiast since middle school, so it wasn’t an easy decision. Here’s my logic:

• I could drive only one car at a time. Owning more than one car was fun but felt wasteful.
• I wanted to simplify life by getting rid of unnecessary things that require time and energy to maintain. I decided I’d rather put that time and energy toward people and experiences that enrich life.
• I began walking to work, so I rarely drove even one car, much less two. If I drove at all, it was usually on weekends. And most weekends I took Uber for social outings to avoid having to park.
• I felt we were at the tail end of an economic cycle. I wanted to prepare for a downturn by reducing my expenses.

This was before the pandemic. Much of this logic is still valid, but some—using Uber, for instance—is up for debate.

Today I read an interesting KMPG report, “Automotive’s New Reality: Fewer Trips, Fewer Miles, Fewer Cars?” It discusses vehicle miles traveled (VMT) going forward. Here are a few highlights:

• A work-from-home norm could reduce commuting and VMT.
• Online shopping and delivery services (for groceries, for example) could reduce shopping trips and VMT.
• Reduced use of public transportation could increase consumer VMT.
• Will mobility services such as Uber and Lyft return to growth? Consumer comfort with mobility-as-a-service could affect consumer VMT.
• Reduced consumer VMT could increase commercial VMT and cause certain businesses (think UPS, FedEx, Amazon) to need more delivery vehicles.

I haven’t driven much in the last five months and I don’t see that changing for the rest of the year. I believe the pandemic is fundamentally changing human behavior. The old norms will cease to exist, and new norms are forming. I envision reduced consumer activity and more time at home. Socializing will be with more intimate groups of family and friends in homes.

Cars aren’t going away anytime soon, but I do think their role in people’s lives will diminish. Industries that support this new reality will grow: e-commerce, logistics, transportation and delivery, etc. Commercial VMT and employment opportunities in these industries will grow too.

What are your predictions about cars and VMT?

Today I caught up with a family member. One of the things we talked about was my habit of posting daily. Bob asked how long I’d been writing, how long I planned to write, and why I had decided to write every day. I told him that I’ve been writing for four months and that I plan to do it for at least a year (hopefully much longer) and explained my reasons. I get asked these questions a lot. Most people say, “That’s nice to know,” and the conversation moves on. Today was different.

Bob shared how my posts have affected him. I really enjoyed the feedback after writing every day for months with little idea of whether I’m doing anything other than whistling in the wind. Bob said he reads my posts every day on LinkedIn’s app. LinkedIn doesn’t provide stats on article impressions or views, so this was news to me. And he said that he has shared some of my posts. With no stats, I had no idea if I’d gotten any shares. Then he told me how my weekly work-from-home posts have helped him manage better. Those are the posts in which I track how many weeks I’ve worked from home (sadly, it’s been eighteen), describe my main observations during the week, and summarize my takeaways. I assumed this post didn’t resonate with others. It was designed to force me to reflect every week and be aware of the pandemic’s impact on my mental state and to be my “easy” post for the week. I thought it would bore people.

I found out that Bob has enjoyed my reflections so much that he’s borrowed the idea. He now reflects about things himself, both alone and with his team. They have a standing virtual conversation that’s become the highlight of their week. They share personal and professional thoughts and open up about their mental state. It’s become a substitute for lost water-cooler talk and brought the team closer.

My conversation with Bob was eye-opening, to say the least. Never in a million years would I have guessed that my posts had helped a team connect. Or that anyone reads them every day. When I began writing, it was to give back and help others by sharing my experiences and thoughts. I reflected on what I’d learned after 60 days. Today, I learned more. Bob helped me understand the reach of my writing and the impact it can have. I’m glad my posts add value to others’ lives, grateful for the experiences and opportunities that I’ve been blessed with, and encouraged to continue writing.

Next time you’re considering doing something positive for others but aren’t sure if it will be helpful . . . do it anyway. You could end up having a much bigger impact than you ever could have imagined!