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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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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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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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No One Bats a Thousand

I was catching up with someone who had recently received unexpected bad news. He had all the reason in the world to be angry, but he wasn’t. He was focusing on everything else that was going well and what awaits him once he makes it through a tough time. I’m happy he has such a positive outlook.

Two people can look at the same situation and see completely different things. The difference is often one of perspective. We can’t always control what happens to us, but we can control how we think about it. Our thoughts control our actions. In turn, our actions can affect the situation we’re in or at least what happens to us next.

No one bats a thousand. We all strike out at some point. It’s just how the game of life works. When I strike out, I try to keep a positive outlook. So one strikeout doesn’t lead to a lifetime of strikeouts, I move on. I don’t want to lose the game of life.

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Multiple Winners? A Great Market!

I spent time reading an interview of a tech CEO today. He discussed his market and why he’s excited about his company’s growth prospects. Each of the largest players in his industry has no more than 4% market share, yet a few of them do over $100 billion in annual revenue each. It’s a massive market. Large businesses can be built serving a small fraction of it. It’s certainly not a winner-take-all market: there will be multiple winners. This CEO thinks his company can grow rapidly for many years to come without owning a significant percentage of the market.

Market size is something early founders should consider. The size of the market (along with other factors) can have a big impact on the company’s ability to achieve sustained rapid growth. Big or rapidly growing markets are great for building high-growth companies. Small or declining markets usually make sustainable high growth much more difficult.

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Disruption Causes Disruptors

I watched a video featuring a CEO who’s leading a publicly traded insurtech company. He shared his view that disruptors aren’t causing disruption. Instead, he believes that humanity is going through a period of transformation unlike any we’ve seen before. We’re seeing unprecedented change happening at a pace that’s exponential because of technology. This shift has created a wave of disruption that disruptors are riding. As he put it, disruption is causing disruptors.

At CCAW, we built technology that allowed us to offer a better experience to customers at a lower price. Because of the technology, we could do so consistently and in a way that was scalable. I didn’t view CCAW as a disruptor. We were a company bringing much-needed change to an antiquated space via technology.

We’re currently living through a period of stunning transformation because of technology. Over the next decade, we’ll continue to see expansive, blisteringly fast change in human society. One result will be a period of unheard-of entrepreneurial prosperity.


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All-in Founder Story

Today I listened to a founder tell his origin story. He had a dream as a child, and he put everything into making it come true. In high school, he was crushed when that path was closed to him. In college, he decided to start a company around that childhood passion. He went to school full-time and worked two jobs to bootstrap his start-up. He didn’t have the technical background to build the product he envisioned, so he taught himself the tech skills he needed. Eventually, he left college early to work on his company full-time. Fast forward a few years, and he now has customers lining up to give him over $1 million in annual revenue.

This founder has a big vision for his company. It hasn’t been an easy road, and he’s had to make significant sacrifices along the way. At every step, he’s proven that he’ll do whatever is necessary to turn his vision into reality. He’s all in. I have no doubt that he’ll become successful, and I’m excited to watch him continue his journey!

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