Today I had a great conversation with an Atlanta founder. He casually mentioned that he was calling from Africa. We were talking for the first time so I could learn more about his business, and this caught me off guard. After I heard his story, it made sense. He’s passionate about a space and created a startup to capitalize on an opportunity he saw. After a few months, through networking he realized there’s a huge problem in Africa that his startup experience qualifies him to solve. He immediately flew over to learn more and establish local relationships. The opportunity was much bigger than he had thought, and he decided to stay and build his company and team in Africa. He comes back to the United States periodically but spends significant time in Africa. The company has grown ten-fold since early 2020, has more than fifty employees, and is still hiring. By all accounts, it’s very successful.

This entrepreneur took a huge leap of faith. He moved to a different continent to tackle a big problem and has built a massive company. I’m pretty sure that when he first went to Africa, people close to him couldn’t make sense of it. They didn’t understand why he would take the huge risk of going to a foreign place. Fast-forward to today: his company is thriving and his decision looks perfectly logical.

Founders have vision. They see things others can’t. Sometimes turning that vision into reality means making decisions that others won’t understand. Even if you don’t move to another continent, your decisions will often go against the grain when you make them. If you’re passionate about something and you see an opportunity that other people don’t seem to, don’t be afraid to make tough decisions. People won’t “get it” now, but they will when they’re celebrating with you at the finish line.

I recently chatted with a startup team. I wanted to know how they resolve disagreements. They all said they first listen to each other’s points to understand the different perspectives. Then they discuss what’s in the best interests of the customer. They’ve disagreed over the years on some pivotal issues that changed the company’s trajectory, but it never hurt the team. If anything, it helped build trust because each person felt heard and understood even if the ultimate decision wasn’t what they wanted.

Listening with the intent of understanding different perspectives is effective. I’ve consistently seen that teams who handle disagreements this way resolve them more effectively and make better decisions.

The next time you don’t see eye to eye with someone, consider taking the time to listen to them. Don’t interrupt. Keep listening until you understand their perspective. This simple but powerful approach can lead to a compromise that everyone can live with.

Productivity is something I think about often. Am I being productive? Is my time being applied to the things that matter most right now? Are there hacks or tools that can help me be more productive? This is driven by my perspective on time. I’ve always viewed time as precious. You can’t create it, buy more of it, or get it back once it’s gone. You can only manage it. I’m not always successful, but I do my best to manage my time, and I’m always trying to improve in this area. I don’t want to take time for granted.

I try to make the most of each day (though, of course, I have off days) by working from a to-do list. In the morning, I think about the things that need to be done and prioritize them for the day. I try to keep the list short—three to five things—to increase my odds of success, but even so there are many days when I don’t accomplish everything I wanted to.

Today, I met two founders who are rethinking the to-do list. Their approach is interesting and could make executing tasks across different platforms more efficient. I’m excited and curious about what they’re working on and looking forward to trying their product.

I’ve never mastered time management and productivity. Recently I’ve come to realize that I probably never will. I now believe that I’ll continually work at improving for many years, learn, and adjust my habits accordingly. Hopefully, when all is said and done I’ll be happy with how I used my time!

I was a nontechnical founder who used technology to scale CCAW. I’m often asked how I went about it. Full transparency: I got lucky. I was fortunate enough to be in the right place at the right time to build relationships with talented technical founders. But I also made a point of researching and preparing. I was determined to understand the tech-y world they lived in. It wasn’t fun or easy, and I went through a period of discomfort, but I grew from it. In the beginning, I had a bad case of imposter syndrome. I felt out of place and often had no idea what they were talking about. But as I’ve written before, I took mental notes and made a point of researching and understanding (at a high level) concepts that were new to me. There were some embarrassing moments, but over time I gained a decent understanding of things.

To this day, I’m still learning. When I meet with early technical founders, I use the same approach: I ask questions and research what I don’t understand.

One of the things that used to trip me up was terminology. I simply didn’t know what certain things meant. This can be detrimental to early founders trying to raise capital. Fair or not, investors expect founders to know certain acronyms and other terminology. Here are two good resources for this:

• The Ultimate VC Glossary
• 16 Startup Metrics

As Roman philosopher Seneca said, luck is what happens when preparation meets opportunity. If you’re an early-stage founder considering raising capital, make some time to prepare by learning the lingo of the investor world. Your efforts could lead to the luckiest break of your life!

An elder once told me, “You can have whatever you want, but you can’t have it all at once.” I didn’t appreciate the wisdom in that statement back then, but I do now. I learned how right he was from some painful experiences. People have a finite amount of time and energy, so accomplishing an infinite list of things at any given time isn’t realistic. Prioritization is the key.

Here are a few things I’ve learned about prioritizing over the years:

• Start with the end in mind – I first try to determine where I want to end up or at least the direction to head in. This compass helps me when I’m struggling to prioritize.
• Time sensitivity – If something is time sensitive or its window of opportunity is closing, I try to assign it a higher priority. Everything isn’t time sensitive.
• Things will drop off – Some stuff won’t make the cut and that’s OK. If I know something won’t get done because it isn’t one of my priorities, I try to communicate that to anyone else who’s involved.
• Small number of priorities – I do best when I have a list of three to five priorities. More than that and I’m less effective.
• Impact on others – I’ve caused and been on the receiving end of collateral damage when too many things are forced at once. When you don’t prioritize, others can be affected as much as or more than you are.

I’m still a work in progress. I haven’t mastered prioritization yet, but it’s become a little easier now than I’ve learned these things. I hope you’ll find them helpful too.

In the early days of a startup, the founders are the glue. The vision for the company is in their head. They understand better than anyone how all the pieces fit together. With minimal resources, they’re usually involved in all aspects of the business because the team is so small, junior, or part-time (e.g., composed of contractors or interns). Founders are holding it all together and driving it forward. Founders are the duct tape and the bubble gum. If they aren’t around, things go sideways or screech to a halt. Fear becomes ingrained in their head: if they don’t do it, it won’t get done or it won’t get done right.

This is normal and can be beneficial in the early days. It can be the key to finding product–market fit. Being involved in everything allows the founder to get feedback directly from customers and adjust the entire business quickly. They can continually do this until product–market fit is achieved. Achieving product–market fit before the company runs out of runway is many times harder if the founder isn’t around.

Once product–market fit is achieved, though, this quickly starts to work against the company. Once you’ve fine-tuned your solution and your customers see its value and readily pay for it, it’s time to scale. As you scale, or try to, everything gets bigger. The team, number of customers, and initiatives all grow. With this complexity, the small startup that once relied on its founders is now it’s own living thing. It becomes impossible for the founders to have their hands in everything. There’s too much going on for it to all flow through founders. There aren’t enough hours in the day. If founders insist on continuing to be the glue, they become a bottleneck. Decision-making and growth slow drastically. Team members may become frustrated and leave.

Lots of founders don’t realize their insistence on being the glue is thwarting growth. It happened to me at CCAW and to many other founders I know. Once a founder figures this out, they should adjust quickly. I did this at CCAW, putting my trust in direct reports to make the right decisions to achieve our metrics. I was relieved. It was hard to not know everything, but I soon realized that it freed me up to think more strategically and see the business through a different lens. I was no longer in the weeds. I wasn’t even worried about the trees. I was looking at the forest!

If you’re a new (or newish) founder, you should understand that being the glue for your company is important. But when the company has entered its next phase, you need to put the right people, systems, and processes in place to allow the company to grow. It’s OK if you don’t know everything, and you’re not involved in everything. It’s means you’ve done a good job and your baby is becoming an adult!

Today marked the end of my thirty-third week of working from home (mostly). Here are my takeaways from week thirty-three:

• Election – Next week’s election is top of mind for me (and many others. I’m encouraged by the high voter turnout so far. More people are exercising their right to vote, which I love (regardless of their views).
• October – The month is over tomorrow, and it’s been a whirlwind. I’ve settled more into my second act as an investor and started to get into a groove that works for me. I still need to work on lots of things, but October was better than September.
• Points of failure – This week, many in Atlanta were without power because of Hurricane Zeta. It disrupted things, for sure. I’m now wondering how working from home and more points of failure at each worker’s home (e.g., power outages and internet connectivity issues) are interacting. Working from home is here to stay in some form, I believe, but large companies will be thinking about helping their teams mitigate these problems as much as possible.

Week thirty-three was a good week and October was a good month. Looking forward to finishing out the rest of the year strong, safe, and healthy!

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

In 2013, I read an article about Cash App. It was described as a way to easily send money to other people. I was intrigued. I’m notorious for never carrying cash, and my friends always end up spotting me. Settling up with them was always a pain. I tried Cash App and that pain went away! I loved its simplicity and how the app made digital transfers of money to friends easy.

I haven’t paid for anything with cash (or even seen a dollar bill) since March. I barely carried cash before the pandemic, but now I never do. I probably won’t need to go to an ATM until 2021. Today I was chatting with an entrepreneur who’s working to modernize payment options available to consumers on websites. Reflecting on my own habits, I realized how crucial digital payments to merchants have become. I pay for almost everything online. Then I started thinking about how painful some of those experiences are and how that friction affects how much and how frequently I spend with a merchant. The easier it is, the more I spend. Amazon captures so much of my spend that it’s ridiculous. But even its payment processes could be improved.

The pandemic has accelerated many trends, and upgrading the way we pay for e‑commerce purchases is no exception. Consumer habits have changed—many permanently—and I predict that how we pay will evolve and more closely align with everyday consumer habits (e.g., sending text messages). I’m excited about this evolution and can’t wait to see what great fintech solutions entrepreneurs come up with!

A few months back, I shared that CCAW’s technology became the secret sauce that allowed us to scale quickly. At a very high level, our technology focused on workflow management. We built it for internal use over many years. It was customized to our needs, so we never considered offering it for sale.

Over the last few weeks, I’ve had a few conversations with entrepreneurs who also built workflow technology internally. They now believe their technology has broader applications, and they’re building platforms to help other companies standardize and automate aspects of their businesses. I think they’re on to something and will build large businesses themselves.

Workflow-management technology is a great foundation upon which to build a tech company. The concept can be applied to numerous aspects of a business. And many things are still done manually or inefficiently, so the opportunity for improvement with technology is significant. A number of technology companies have built wildly successful workflow-management technology businesses that serve as blueprints for early entrepreneurs. (Click on the link to my previous article, above, for specific companies.)

I’m a nontechnical founder, but with my team I was able to build a large company underpinned by technology. And I’m not the only one. Nontechnical founders who want to build a great technology company as their second act can do well basing it on workflow-management tech. If they’ve lived the problem in their first company, they’ve amassed invaluable knowledge. With it, they have a ready-made founder–market fit, and they’re perfectly positioned to solve the problem better than others. (If you’ve been reading my posts for a while, you may recall that I’ve talked about this—a founder’s unfair advantage—before.)

This organic knowledge also helps these founders clearly articulate a compelling vision that they’re genuinely passionate about. They’re usually looking to create a world without XYZ problem in it so other people don’t have to experience the pain they did. Such a vision is a great recruiting tool, especially for attracting a technical co‑founder. Their remembered pain can also help these founders empathize with what their potential customers are experiencing, which can help drive the vision for the product.

Today I had a great conversation with a founder friend that reminded me of something. The journey of a founder is an evolution. The needs and priorities of a founder will change.

Founders who build successful companies often end up selling them. What then? Many struggle to decide what they want the answer to that question to be. Do they start over with another company? Do they retire to a tropical island? Do they use their experience and skills to re-focus their efforts on giving back?

And it’s not just their professional lives—all aspects of a founder’s life evolve. I was 100% focused on CCAW as an early founder. I worked all-nighters and prioritized CCAW’s success above most other things. I don’t recommend that approach, but it’s what I did. As I’ve gained more experience, a lot has changed. I don’t do all-nighters anymore. My brain and body don’t respond to them like they used to. My priorities have also changed. Family and friends rank higher than professional success. And how I define success has even changed. I now think of success as helping others reach their full potential as opposed to building my own successful company. As I continue to live, I’m sure more changes will come.

Evolution is part of life. From my experience, it’s important for founders to recognize this evolution, embrace what comes from it, and adjust accordingly. I didn’t recognize that my needs and priorities were changing—I carried on with the same approach, the same habits. It took life slapping me in the face to change and make a ton of adjustments quickly. I wish that I’d taken time to regularly reflect on this and make gradual adjustments periodically. Now, I plan to reflect annually during the Christmas holidays. It’s a perfect time to think about the past year and the one coming next.

Founders should begin their journey with the understanding that who they are now probably isn’t who they will always be. This will make it easier to recognize their evolution, process it emotionally over time, make practical decisions, and implement changes gradually. Life never stands still!