A friend shared an interesting realization with me today. He had a generalist approach early in his career. He wasn’t someone who grew up saying I want to be an X when I grow up. He wasn’t sure exactly what he wanted to do, so he learned about a lot of things. He knew a lot about a lot of things but wasn’t an expert on anything. He wishes he’d known earlier what he knows now. He wishes he’d picked something and gone deep into it earlier. Eventually, he went deep and became a domain expert, and it’s served him extremely well.

Early-stage founders are operational generalists by necessity. Resources are too scant to do everything, so founder(s) fill a lot of gaps. They do sales, marketing, HR—whatever is needed. As revenue (or investor capital) increases, they begin to be able to afford help. Until then, they’re the glue holding everything together.

Founders need to be able to do multiple things in the business, but the great ones know their space cold. They have domain knowledge too. They’ve learned so much about a problem and market that they’re qualified to solve the problem better than others are.  They often have a unique insight that will make their solution superior.

If you’re a founder or considering becoming one, take the time to learn your space and your potential customers well so you can make early strategic decisions that set you up for long-term success. Also be ready to jump into areas that you know nothing about. Learning new things on the fly will be key to surviving those early days when you’re wearing multiple hats.

Had a great chat with a friend today. He reflected on his entrepreneurial path and said something that stuck with me: he had the support of advisors and investors in the early part of his journey, but he may not have been as clear as he could have been about how they could help him or in what areas he needed help.

A lot of founders make this mistake. I’m one of them. I didn’t take the time to process everything that was happening to understand where I was failing. I didn’t ask my team members for feedback, either. When I connected with people who were in a position to help me, I didn’t make the most of those opportunities because I didn’t have a clear ask. Since I couldn’t articulate how they could help me, they didn’t. It was a big miss.

Building a company is hard, and founders can’t do it alone. They need help. Everyone understands that. But it’s not apparent to outsiders how they can be helpful. They must be told.

If you’re a founder, consider taking time to periodically think about what kind of help you need. Then tell other people. Those conversations will make it much more likely you’ll get exactly what you need.

Today I listened to a successful founder share his vision for doing good through entrepreneurship. He’s been an entrepreneur for almost twenty years and has exited his company. Now he wants to help early founders make a positive impact on society through their companies. His strategy for doing this is great, and I think it will be valuable to early founders.

Purpose matters a lot to this founder. It’s a big part of what made him successful. I can’t wait to see the positive impact he has on other founders and, in turn, the impact they have on society!

I listened to an early-stage founder, John, describe how he wanted to emulate a successful founder, Bob. John excitedly recapped Bob’s journey. John was planning to follow a similar path to success with his young company. But I noticed that John’s recap began where things had begun to go well for Bob. I know Bob’s story well. He endured years of painful failure. As I listened to John, I realized he didn’t know the full story. He’d only heard the happy parts.

I told John about Bob’s failures. He was surprised. He’d thought that an entrepreneurial journey that was only up and to the right—a string of successes—was conceivable.

Most successful people have failed miserably, but they kept at it. Failure is usually an important part of accomplishing anything great. What you learn from failure often creates the foundation needed for success. Put another way, you often must lose to win.

If you’re looking to do something great, prepare yourself for failure. Instead of letting it get you down, look at it as an education that took you one step closer to success.

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.  

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!

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?

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.

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.

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.