POSTS FROM 

September 2021

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Which Is Better, Many Specialized Tools or a Few That Multitask?

I use many digital tools every day. There’s a specific tool for everything I need to do. I don’t complain because it’s better than doing tasks manually.

I had a chat with a founder that got me thinking about something. Is it better to create solutions that help people use a variety of tools effectively or to help them consolidate by using one tool that does the job of many tools? This founder thinks it’s not a good idea to ask people to change tools: the friction would be too high because people don’t like change. It’s better, in his opinion, to help them make the most of their current tools.

As I’ve thought about this more, I’ve decided that the right answer for me boils down to time. What will allow me to do more with the time I have? Most things I do daily don’t need to be perfect; I just need to complete them. The path that leads to more productivity is the one I’ll go down.  

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Entrepreneurial Itch

It’s a great time to be an entrepreneur. We’re in a period of change when people are looking for new solutions to old problems. A lot of capital is being deployed to early-stage companies. Over the last few weeks, I’ve discussed this dynamic with founder friends. I’ve been asked if I have an itch to get back in the game. Translation: am I itching to start another company?

Reflecting on this a bit, I recognized that I’m an entrepreneur at heart. As a kid I mowed lawns, sold bales of hay (another story for another day), and sold mix CDs. In college, I sold automotive parts to friends. Post-college, I grew an e-commerce automotive parts company (after a stint in corporate America).

Entrepreneurship changed my life trajectory. It allowed me to met amazing people, changed how I think about the world, and helped me become more self-aware. Without it, I’m not sure where I’d be. After experiencing this incredible journey, I find myself in a different place. I want to help others interested in entrepreneurship change their life trajectory. I want to help other people reach their full potential through entrepreneurship.

I’ll always be in the entrepreneurial game. What that looks like will continue to evolve over time, but I plan on staying in the game as long as it will have me!

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What Keeps You Up at Night?

When I meet founders, I like to know their background. It helps me understand how they arrived at the problem they’re solving. In a recent conversation, a founder told me he’d turned down an opportunity to be one of the first hires at another company. That opportunity was valued at over $1 billion a few years later. When I asked why he’d turned it down, he said he wanted to work on something that keeps him up thinking about it all night. He has no regrets because he isn’t passionate about the problem the other company is solving.

I immediately got what this founder was saying. Starting a company isn’t for the faint of heart. It’s a multiyear journey full of extreme highs and lows. Having passion about what you’re doing is essential. It helps you push through the exhaustion after years of grinding and low points when nothing is going right. Passion is a main ingredient of entrepreneurial success (and of success in life, for that matter).

So, what keeps you up at night?

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A Space Ripe for Disruption

For the past few weeks, I’ve been putting off finding a service provider to transport something a long distance. I need a specialty transport company. When I started looking, I remembered why I put this off. I’ve been looking at providers online, and all of them have outdated websites and require a phone call to get a quote. I have a short list of companies now, but I still need to carve out time to call each one and then schedule the job. The customer experience hasn’t been great so far, and I expect this to continue until the task has been completed.

This industry is an entrepreneur’s dream. It hasn’t embraced technology although it has a huge market and many customers are companies who will do repeat business. They’re looking for a better alternative.

This industry isn’t cool or attractive from the outside looking in, but I think a savvy founder could build a massive business disrupting this space.

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More on the Rise of the Individual Investor

A friend read my post about individual investors becoming more of a force. We had a good chat about it today. Here’s my takeaway:

Investor knowledge gap – Just as early-stage founders have gaps in their knowledge about raising capital, lots of investors have gaps in their knowledge about deploying capital into early-stage tech companies. They see what’s happening, want to participate, and have the capital, but they don’t know where to start. This is beginning to change. Information is more readily available. More platforms are making it easier for would-be investors to find and participate in tech deals and connect with and learn from other investors. As more individual investors learn about and gain access to investment opportunities and find their community, they’ll start deploying capital.

Great chat today with my buddy. We’re both looking forward to the rise of the individual investor.

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The Rise of the Individual Investor

I’ve been interested in personal finance and investing since adolescence. I’ve always read about them as much as possible, and I even crowdsourced financial advice when I got my first job offer. Usually, I was in the minority in my circle of friends. Finance and investing just weren’t things that many were interested in or cared to talk about. Over the past eighteen months, that has changed drastically. Investing and finances are regular topics in my various friend groups.

Consumer interest in investing and personal finance will continue to expand. Information is more readily available, fees have been virtually eliminated, and access to platforms is easier. This is leading more people to take a hands-on approach. They’re learning and applying their knowledge. I think this will be a positive trend in the long term, but there may be a period of adjustment in the short term.

Public investments like the stock market are most accessible, and that’s where many consumers have recently gotten their feet wet. As they get more comfortable investing, I suspect interest in investing in private companies will grow. If that happens, entrepreneurs will likely see more willingness among their friends and family to invest in their early ventures. This will have pros and cons but, I think, net out as positive. Founders will have access to more capital to build businesses. Consumers will be able to invest in private companies that serve their communities and hopefully see financial gains that they can reinvest in more founders.

I think the next decade or so will be one of change and disruption like nothing we’ve ever seen. Investing will look radically different in the future. I’m excited to watch the rise of the individual investor and how their capital will change the entrepreneurial landscape.

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Weekly Reflection: Week Seventy-Eight

Today marks the end of my seventy-eighth week of working from home (mostly). Here are my takeaways from week seventy-eight:

  • Inbox zero – I’m more effective when I work through my inbox daily. I haven’t been doing as good a job with this as I’d like. This week, though, I was more consistent about checking something as done, delegating it, or deferring it to a later date (i.e., snoozing it to remove it from my inbox).  
  • Perspective – I focused on getting the perspective of credible people this week. Their feedback was insightful, and I’m glad I did this. Looking forward to continuing it.
  • Focused – I had clear written goals that I needed to accomplish by the end of the week. I made a point of revisiting that list every morning, which helped me focus on the activities that mattered most. The week ended up being productive in the ways that I’d aimed for.

Week seventy-eight was active. Lots of good things going on. I was more intentional and focused this week, which paid off.

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20-Year-Old Expert

Today I listed in on a conversation between two guys named Chris and Tom about a topic I’m interested in. The more I heard, the more amazed I was at how deep Chris’s knowledge is. Toward the end of the chat, I learned that Chris is a 20-year-old recent college dropout. He wasn’t satisfied with what he was learning in school. He felt his professors weren’t up-to-date on the latest trends and thinking. His education wasn’t equipping him to navigate what he was seeing in the real world every day. So, he dropped out and started educating himself by reading books and consuming online content from thought leaders. And he used his newly acquired knowledge to get a job in the field he wants to be in. Most likely he’s on his way to a lucrative career.

That may sound extreme, but stories like Chris’s will quickly become commonplace. More students will choose to bypass a traditional four-year education for a more customized path. They will go deeper into the topics that interest them much faster and begin to apply their new skills in the real world much faster than previous generations.

I suspect this dynamic will have a big impact on the workforce, as well as other parts of life. I’m not exactly sure how yet, but I’m curious to watch this play out.

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Knowledge Sharing

I had two unrelated conversations today in which the same issue was discussed: knowledge sharing. Both people I talked with believe that a knowledge-sharing deficit is having a negative impact in various areas. In some instances, it’s widening existing gaps; in others, it’s slowing the pace of progress.

When I started my company, my knowledge gaps around start-ups and technology were massive. I was lucky enough to be able to surround myself with other founders who were open to sharing their knowledge. I credit their willingness to share with accelerating the success of CCAW. Without them, I think it would have taken twice as long for us to reach $10 million in revenue—if we ever had.

Sharing knowledge can have a profound impact. My founder journey is a testament to that. For that reason, I try to share what I’ve learned (for whatever it’s worth) through daily posts and other means. I hope it’s helpful to some people and helps them get closer to achieving their goals.

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Blind Spots: We All Have Them

I caught up with a founder who’s working on a big problem. Things haven’t gone as he planned, and we talked about why. He had thought he was well equipped to solve the problem, but now, after reflecting on setbacks, he understands how certain blind spots in key areas and the industry hindered him. He’s working to address them and continue building.

I can relate to this founder. As an early founder, I learned the same lesson. I too thought I was well equipped to build my company until things didn’t go as planned. I didn’t have anyone else to blame, so I took a hard look at myself. I realized that I didn’t know everything and needed help. Over a period of time, I got a coach, joined EO Accelerator, and recruited other leaders into the company. I tried to fill my blind spots as best I could. Luckily, it worked. Things turned around and we scaled to over $10 million in annual revenue.

Everyone has blind spots, and that’s okay. If you’re a founder, it’s important to understand what yours are so you can find alternative ways to see everything clearly.

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