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.

One of the biggest mistakes I made at CCAW was not having a cofounder. When I speak with early entrepreneurs, I share my experience and how difficult things can be as a solo founder. Fortunately, many understand the importance of a cofounder—but they struggle to find one. I’ve been thinking a lot about this common challenge. And I recently met a team that was the result of a different approach to solving it.

The CEO was passionate about a particular space and wanted to build a technical product to solve problems he saw in it. He was nontechnical, so he couldn’t build it himself. He let people in his network know what he was looking for, and he also did something else that was highly effective: he shared his thoughts about the space in blog posts. In them, he explained how he viewed the space and the problems customers were experiencing. And he described his vision for how these problems could be solved. The posts showed his passion for the space and that he was committed enough to take the time to write and share his thoughts.

As I got to know the team, I learned that those posts were pivotal in his recruitment of three cofounders. The other founders were also passionate about the space and came across the CEO’s posts while researching it. The blog posts weren’t intended to recruit others, but they did just that. They attracted like-minded people who reached out, wanting to be part of his vision.

There are lots of strategies for finding a cofounder. I really like the blogging approach because it’s a passive way to recruit that continually works in the background and at the same time adds tons of other value for readers and the author. Medium and other platforms make blogging quick and easy.

If you’re a solo founder looking for a cofounder, consider writing some blog posts about your space and your vision. You never know—they just might help you find the perfect cofounder!

Capital is one of the highest hurdles early entrepreneurs encounter. Most people won’t work without compensation and most vendors won’t give away goods or services. It’s easy to see why lack of capital can be a challenge. When I meet with founders at the idea stage, though, I often remind them that capital alone won’t lead to success.

Capital is a tool. It helps you acquire the resources you need to build a vehicle that will carry you (and others) to your destination. The tool and the vehicle are cool, but what counts is the destination. Without it, the tool and vehicle have no purpose.

The most successful entrepreneurs I know all had a vision for their company early on. They saw a problem and envisioned a solution. Where others saw obstacles, they saw opportunity. In my opinion, it was their vision that allowed them to become successful. Sure, the capital they raised along the way (if any) was helpful, but the vision was indispensable.

If you’ve identified a problem you want to solve, consider taking time to develop and expand on your vision. If you’re successful in solving this problem, what does the world look like? Share it with people who can battle-test it and help you make it better. This simple exercise will be valuable and help you convince others (including investors) to join you on your journey.

Yesterday I caught up with a good friend who’s also an entrepreneur. He said he was recently asked, “What would you change or do differently?” We’ve both been asked this question for various reasons, so we had a great chat about it.

Things will inevitably get challenging during the entrepreneurial journey. Entrepreneurs will find themselves making important decisions based on imperfect information. Having lived this scenario many times, we agreed about what matters most:

• Everything happens for a reason. The reason may not be clear at the time, but there is one. Take time to reflect on what happened, and why, so you can apply what you learn in the future. What seems like a failure today could be a steppingstone to a decision that leads to massive success. Reflection and the understanding it engenders are key to improving your decision-making.
• Neither of us would change any of our decisions. We don’t second-guess them. We didn’t know then what we know now, and we stand by our decisions because we did the best we could with the knowledge and other resources available to us. Don’t continually relive the past. Focus on the future.
• It isn’t over until the clock reads double zero. Stay focused on getting the win. Sometimes you’ll make decisions that don’t pan out. That’s OK. Dust yourself off and get back in the game. Remember that it isn’t over yet and you can still make a comeback. If you win in the end, all your turnovers and air balls don’t matter anymore.

My conversation with my buddy was a great reminder for both of us that we wouldn’t change a single thing. As he so eloquently put it, “All windshield, no rearview mirror over here!”

Entrepreneurs are sometimes held to a standard that isn’t realistic. Some people think of them as superhuman and hard-charging, with everything figured out. This is only partly true! Most are hard-charging, but they experience the same emotions as everyone. And they definitely don’t have everything figured out—figuring it out as they go is par for the course.

Like everyone, entrepreneurs have to do things they aren’t good at doing. Unfortunately, when you’re building a company your weaknesses are exposed early and how you mitigate them can be very public. For example, if you’re not great at communicating, that will be quickly apparent to your team. They’ll see firsthand your evolution—the ups and the downs—as you become a better communicator.

I myself spent many years unaware of (or ignoring) my weaknesses at CCAW. I thought founders had to be strong and show no cracks. I was trying to live up to an image that was ridiculous. And I wasn’t alone. Other founders (in my opinion) were doing the same. Over time this charade wore on me mentally. I was failing in key areas and trying unsuccessfully to figure out why. It felt like I was drowning.

When I joined accountability groups with other entrepreneurs and listened to them describe challenges and acknowledge weaknesses, my perspective changed. As time passed, I began to open up and share my own weaknesses. I got feedback and learned from their experiences. Being more self-aware helped improve my decision-making and leadership. I no longer expected perfection because I accepted that I’m far from perfect myself.

I’m sharing this because I want to help early founders avoid this kind of self-inflicted pain. From the other side of the table, where I am now, it’s great when a founder is self-aware and willing to articulate what kind of help they need. We know they have weaknesses because everyone does (we’re not shocked or disappointed!) and we appreciate not having to guess what they are. Often, we can help by making an intro, sharing a resource, or describing a similar experience—but only if we know what would be useful.

In August, I taught a lesson lab for Start It Up Georgia. The experience was great and the turnout was huge. There’s clearly a desire for something that helps people start companies in these uncertain times. Today I had the opportunity to connect with five entrepreneurs who are participating in the program. One question everyone was asked: “What piece of technology do you take for granted?”

I learned a lot from this discussion. Most of them chose their cell phone, for various reasons. With less in-person communication and people tired of Zoom meetings, phone calls are more appreciated. The ability to do tasks on a phone while walking in the fresh air was also mentioned. Very interesting altogether.

Also mentioned was high-speed home internet. With so many working from home (and spending all day on Zoom), it was a great choice. Without high-speed internet, productivity wouldn’t be what it’s been over the last seven months. I believe it’s one of the reasons many companies are considering allowing working from home indefinitely.

What piece of technology do you take for granted?

I’ve written about how important finding a co-founder is for entrepreneurs. But equity (company ownership) is a big concern. Specifically, what happens if things don’t work out? If one founder isn’t pulling their weight, do they own as much of the company as they would if they were contributing mightily?

It’s a valid concern. But there’s a simple tool to mitigate it: a vesting schedule. A vesting schedule outlines when each person’s equity is theirs, free and clear. Keep in mind that equity should be earned, not granted, for early employees and founders. The vesting schedule is a great tool to set expectations about equity.

The most common vesting schedule is time-based. You typically see a four-year schedule with a one-year cliff. What does this mean? No equity vests until after a year of employment. If someone leaves in month eleven, they receive zero equity. On their one-year anniversary, 25% of their equity will vest (they stayed for one of four years, or 25% of the four-year schedule). After that, their equity vests in equal monthly increments until the forty-eighth month.  Carta has a good article with details and examples.

At CCAW, we used a milestone-based vesting schedule with revenue as our milestone. As we reached certain revenue targets (while maintaining profitability), equity for leaders would vest. We had a minimum revenue threshold (i.e., cliff) the company had to hit before any equity vested. This schedule was very helpful because everyone was aligned. Our approach was specific to what we were trying to accomplish at the time and may not work for everyone.

Many investors will want to see that founders are on some sort of vesting schedule, which ensures that they’re committed to building the company. There are lots of details that I won’t get into, but the takeaway is that founders should have a vesting schedule (in some form or fashion) if they’re raising investor capital.

A vesting schedule is a great way to protect against someone who isn’t contributing having equity in a company. Finding a co-founder is hard, but vesting schedules overcome one hurdle.