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!

One of the most difficult things any early founder has to deal with is transitioning a team member. I struggled with it and every founder I know struggled with it at some point. Early teams are close knit and can feel like family. Here are a few things I’ve learned over the years that may be helpful:

• Everyone knows – When someone isn’t pulling their weight or they’re struggling to keep up, it’s not a secret. Especially on small teams. Most people won’t say anything to the founder, but they’re thinking about it. A players want to work with A players. A C player can pull down the productivity of the entire team. No one wants to give 100% if they know others give only 70%.
• Company needs evolve – Companies go through growth stages just like people. What’s needed to be successful changes with each stage. Someone’s skills may be great at stage one but insufficient at stage two. It’s common for people to outgrow a company, and vice versa.
• Trust your gut – With every person I’ve transitioned, I knew long before the day came that it would need to be done. Most founders say the same thing. I often waited quite a while to make the change, which was a mistake. It wasn’t good for the person or the company. It’s better to rip the bandage off and allow people to find a role (internally or externally) that sets them up for success than to allow them to continually fail.
• One step ahead – Founders are captains of a ship. They should be looking far out and adjusting course to reach the destination while avoiding icebergs that might sink it. Staying a step ahead can give your people the opportunity to grow their skill set before they’re needed (if you tell them what skills they need to work on). Or it will give you time to find someone with the right skills for the role.

What I’ve said doesn’t apply just to non-founders, but to founders as well. Companies can outgrow the skills of their founder. Founders need to be self-aware and constantly working to make sure their skills match the company’s needs. When people see founders working to make themselves better, they tend to want to do the same.

People are critical to the success of any company and you should always treat everyone fairly and with dignity. Early founders need to realize that keeping someone on too long can harm them, not help them. It’s terrible for their confidence to continually fail. Transitioning them to a role they’re better suited for may be painful in the short term but it will set them and the company up for long-term success.

I caught up with a good friend yesterday. He’s an entrepreneur who has attained what I consider to be an elite level of success. He said something that stuck with me. Business conquests are great, but they haven’t brought him joy. Celebrating life’s moments and sharing experiences with people who matter most are what truly makes him happy.

Entrepreneurs have a vision that they’re trying to make a reality. Often, they think about little else—and sometimes that’s not a good thing. For example, one of my closest friends once invited me to join him and another college friend on a trip to South Africa. It was an opportunity to see a special part of the world with people I’m close to. But I was so focused on making CCAW a success that I thought I couldn’t afford to take the time off. To this day I regret that decision.

I agree with what my friend said. For all the success I had with CCAW, it’s the moments with friends and family that I cherish most. If you know what brings you joy, don’t routinely sacrifice it to your work. Faced with a decision like mine, make it carefully. The opportunity to go to South Africa with friends—or whatever version of such an opportunity turns up in your life—may never come again. Even ordinary chances to enjoy a meal, a concert—whatever floats your boat—with your family or friends are gold. Yes, if you’re an entrepreneur, you must work super hard. But don’t sacrifice your relationships. Make time for what matters most.

Friday marked the end of my thirty-second week of working from home (mostly). Here are my takeaways from week thirty-two:

• Pitch events – This week was busy because of events. Techstars, Venture Atlanta, and others gave companies opportunities to pitch to investors and the community. I wasn’t able to attend everything, but I enjoyed what I did make it to. These events are a great opportunity for entrepreneurs to introduce their companies to a wide variety of people. Lots of companies present when they’re raising capital.
• Outlander event – Our team is working hard to bring interesting events to the Southeast. We have some great stuff in the pipeline. I’m excited about our pitch competition for female founders. Can’t wait to see what problems they’re solving.
• Progress – I couldn’t make progress on everything on my list this week. I guess that was to be expected because of all the events. I’m looking forward to getting back on track next week. I’m going to try Jean-Michel Lemieux’s “1, 3, and 5” approach.
• Relationships – Relationships came to the fore this week. I helped a few connections with projects they’re working on, and others did the same for me. Healthy relationships are bidirectional, and I enjoy helping others however I can. It’s great to see someone become successful and know you played a small role in helping them get there.

Week thirty-two was full of events. I’m looking forward to putting my head down and focusing next week. My goal is to wrap up a few big things before the holiday.  

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