When I started CCAW, I didn’t have a clear idea of where I was heading. It was the great recession and I was happy to still be in business. Eventually, I met entrepreneurs who were aiming for $1 million in annual revenue. I adopted that as my goal. We surpassed it in a few years and went on to reach eight figures. In hindsight, I was thinking too small in the early days. We were operating in a $40 billion market. If we captured 1% of it, our annual revenue would be $400 million.

I thought small because of what I’d been exposed to. I didn’t personally know entrepreneurs who’d built massive companies, so it didn’t occur to me that I could do it, and anyway I had no idea how to go about it. Sure, I read about it, but I didn’t know anyone who’d lived it. As I built relationships with other entrepreneurs, that changed. I watched their companies grow from two people to tens of million in revenue with hundreds of employees. My eyes were opened to the possibilities and my thinking broadened. What once had seemed farfetched now seemed achievable.

Times have changed. Tons of information about building huge companies is accessible to anyone. Even so, I still encounter talented entrepreneurs who aren’t thinking big. It’s my belief that thinking small can prevent you from reaching your full potential.

If you’re considering entrepreneurship, think big. Don’t focus on what could go wrong. Instead, think about how big your company could be if you’re right and things go your way! You may not know how you’ll get there, but that’s OK. If you have a compelling vision, you’re on the right track. Believe it or not, the world is full of talented people who want to be part of something great and can help you figure it out along the way. Think big!

As a former nontechnical founder, I understand how hard it is to build a company that relies on technology. One popular route to building technology is to use technical talent based outside the United States. We used a hybrid approach at CCAW comprising both US and non-US technical talent. Here are some of the things I learned:

• Fit is key – Finding the right person for the role is hard. Spend time making sure the person is a good fit before you pull the trigger. I’ve used Toptal, Upwork, and other services. Regardless of the service, I’ve always had to spend time evaluating the person or firm for fit. It’s one of the most important parts of the process, and you can’t outsource it. Spend time on the front end.
• Nearshore versus offshore – There’s a difference. Offshore refers to another country that has a different time zone and isn’t close to your country. At CCAW, we had offshore team members in Greece, Poland, and the Philippines. Nearshore usually refers to a country in close proximity with yours and the same (or almost the same) time zone. Nearshore can be easier because it’s more likely they’ll understand your culture and have similar work hours. We had nearshore team members in Nicaragua at CCAW. Both nearshore and offshore worked for us at CCAW.
• Communication – This is more important than technical abilities. You need to be able to easily communicate with someone. If they can’t communicate clearly in your language, orally or in writing, it will become a huge problem.
• Individuals versus firms – There is a difference here, too. A good dev shop will have the processes, systems, and management layers in place that will increase the chances of success. We had success working with individuals early on at CCAW. As we began scaling and needed more structure, we had success with firms that already had management structures. I enjoyed have one point of contact to manage the relationship.
• Product vision – Someone domestic on your team needs to own the vision for the product and they need to work closely with technical talents to make sure their work meets expectations. This may be the founder early on and someone else as the company grows. I originally had this role at CCAW, but transitioned it as we grew. If you can’t articulate what you want built, the end result will be poor, and it won’t be the technical talent’s fault.
• Expense item versus team member – If technology is key to your strategy, treat the people building it accordingly. Don’t treat them like a line item on the budget. Don’t try to get something for nothing. Don’t just give them a bunch of tasks with no context. Treat them like team members and value the technical insights they bring. Include them in conversations and ask for their perspective. Good technical talents can tell whether you value what they contribute. If you don’t, they’ll decline to work with you and you’ll be left working with people of lesser talent.
• Expectations – Know what you expect and communicate it clearly from the very beginning.

I learned a great deal working with a hybrid team at CCAW. Our team members based outside the United States were strong, and I’m happy I had the opportunity to work with them. Without these people, we would not have been able to achieve eight figures in revenue.

I know a number of wildly successful founders of technology companies who have loved using non-US technical talent. Conversely, I’ve known others who’ve had bad experiences. I personally think there are amazing technical talents outside the United States and that working with them is a huge opportunity for founders. And I think the founder’s perspective and approach determine the likelihood of success.

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

• Hybrid college class – This week I presented to an entrepreneurship class at a local university. I attended virtually, but the class was hybrid. Some students were in the classroom (with masks), and others joined in via Zoom. It was interesting to watch. I’m wondering if the hybrid model will be the norm for undergraduate courses.
• Holidays –I noticed that people are talking about holiday plans and scheduling things is becoming more difficult. I think people are beginning to go into holiday mode mentally. This year has been rough, and I imagine lots of folks are looking forward to the holidays more than ever.
• Strengthening teams – I’m thinking more about how teams can build bonds and rapport while everyone is working from home. As I wrote yesterday, I think random unplanned conversations strengthen teams way more than people think, and they’re nonexistent now. It feels like the missing link in this work-from-home world. If this problem is solvable, it’s a massive opportunity.

Week thirty-five was pretty calm and uneventful. I guess I’m starting to adjust my pace to holiday mode too!

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

Many companies embraced employees working from home for the first time this year. Some had resisted because of productivity concerns. I think those concerns have largely been proven unfounded—but now there are new ones. I’ve personally been paying attention to how diminished socialization is affecting many people. People are social by nature, so removing human interaction can have a negative impact.

For example, working in a shared office makes possible unplanned conversations that help teams bond. Think water cooler moments or walking to lunch with a coworker. These serendipitous confabs seem unimportant, but they help people know and understand each other better. Which in turn helps team chemistry and output.

Current work-from-home tools and approaches don’t allow for chatting. Sure, you can use Slack or some other messaging platform, but it’s not the same.

I’m bullish on rethinking how we communicate. And I think that home workers missing out on informal conversations is a huge problem. Tons of companies of all sizes are looking for a way to solve it. Zoom, Slack, and their like are work-arounds. When someone builds a tool that’s a good solution to this problem, I foresee them building a large business that could change the landscape!

In the very early days of CCAW, I was a one-man band. No team. No advisors or mentors. No investors. No peers. Lone man on an island. I eventually connected with other entrepreneurs in Atlanta who became peers. That group was sharp and way ahead of me in many areas (and they still are!). I began trying to catch up. I read everything they were reading, used all the latest tools they were using, and tried to implement the best practices their companies were implementing. I was afflicted with founder’s FOMO. All of this had some benefits. I learned a lot about a lot of things. But there were downsides, too. Some of what I learned didn’t apply to me. And I wasted a lot of time, sometimes felt stretched, and had a team that didn’t like doing something because another company was.

I eventually took a step back and starting gauging for fit. The list of things my peers were doing was ever growing, but so were my responsibilities at CCAW and the draws on my time. It just wasn’t possible for me to keep up with what everyone was doing. I started thinking more about what was right for me and passing on bad fits. Looking back, I missed out on a few cool things. But more importantly, I didn’t wasn’t time on things that weren’t right for me or my team.

People are social. Most of us feel FOMO at some point. It hit me when I was a student, a corporate employee, and a founder. From living it, I’ve learned that giving in to it—doing something because everyone else is—doesn’t work for me. I’ve gotten better at winnowing out bad fits. I’m comfortable missing out on them. No more FOMO.

Relationships—with founders, community builders, other investors, LPs—are at the heart of venture capital. Healthy relationships with these people and others are important to a successful fund. Over the last few months, I’ve had the opportunity to connect with more investors.

One thing I’ve noticed is that investors interact with their investments in different ways. Some take formal roles as board members, some act as informal advisors (and therapists), and others are mostly passive. To be clear, I don’t think there is a right or wrong approach—what matters is what works best for that investor. I’ve learned that each investor has reasons for their approach.

Founders need to be aware of this when raising capital. Ideally, you should think about what you want from your investor, beyond capital, and partner with one whose style aligns with what you’re seeking. Write down what you need help with. As you speak with investors, ask how they can help you—and how they’ve helped others—in those areas. The responses can help you identify the right investor for you.

I vividly remember hitting certain inflection points when I was building CCAW. I can easily pinpoint them now because they occurred when our growing pains became almost intolerable. We were accustomed to doing things a certain way, but once we grew past a certain point it was torturous. We hit these points at around $1 million, $3 million, and $10 million in annual revenue.

At first, I didn’t know what was going on so I was frustrated. Everything was breaking and my team was stretched, all at once. We dug in to find the root cause. This meant taking our foot off the gas, identifying what was broken, fixing it, and then trying to speed up again. Over time, I realized what was happening. We were outgrowing our system and processes. We needed to slow down to improve our infrastructure to support more growth so we could speed up again.

It’s funny to think about this now because I was warned about these inflection points by other entrepreneurs when I was first starting out. Yet I still missed what was happening while I was living it. I guess I needed to learn the hard way.

Founders aspiring to build fast-growing companies should be mindful that inflection points in a business are very real. There are lots of ways to overcome them and reach your destination, but sometimes slowing down is your best option. Sounds crazy, but it’s true. Sometimes you need to slow down before you can speed up.

Building a picks-and-shovels business can make you super successful. Think about the gold rush in the mid-1800s. You might strike it rich mining, but the probability of finding gold is tiny. Or you can sell tools—picks and shovels—to miners. That’s much more likely to bring you wealth!

Lots of founders want to create the next Facebook or Amazon. More power to you! You might be one of the fortunate few. However, I recommend thinking sideways. I’m bullish on workflow management, but I like picks and shovels too. Twilio, Splunk, and Stripe are all massive companies that the average person has never heard of. As of November 8, 2020, Twilio has a market cap of almost $47 billion, Splunk has a market cap of almost $33 billion, and Stripe just raised $600 million at a $36 billion valuation. Their technologies underpin or monitor popular services that consumers use every day. They didn’t invent the next best thing, but they’re critical to the next best things’success.

The pandemic has accelerated change in the world. Things that would otherwise have played out over a decade happened in six months. Rapid change has created a rare opportunity for founders to build solutions that will support the next wave of transformational companies. If you’re a founder or want to be, here’s a good question to ponder: what picks and shovels can you offer that others will need?

This week I had a setback that stung badly. I’ve been working with an entrepreneur on an investment. He’s smart and has built a great product. I was excited about partnering with him to help him reach his full potential. Then, at the last possible moment, the deal fell apart.

The news caught me off guard. I thought about it a bit, and the next day I talked with the founder and wished him well. I offered to maintain our relationship and share my experiences as a founder with him. We discussed some of the things he’s learned and agreed to touch base soon. He even wants to make an introduction to another founder. The conversation ended on a very positive note.

Winning the opportunity to invest was my goal, but it didn’t happen. In business sometimes things don’t work out, and that’s OK. Though I lost this opportunity, I built a good relationship with a strong founder who’ll go on to do interesting things. I’m excited about watching his journey, sharing my experiences when he asks, and helping him if I can.

This was a loss as an investor, but it won’t be my last. I learned a lot. Most important: handle losses the right way and maintain relationships.

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

• Election – Keeping up with the election cut into my productivity quite a bit. Looking forward to a decision so we can all move forward. I foresee Atlanta being on more people’s radar because of its outsize influence on this election.  
• Work-from-home posts – These posts began as a way for me to document working from home during a pandemic. They’ve morphed into more of a weekly reflection. I get more out of this habit than I originally envisioned and really enjoy it. My daily posts cover the last 24 hours, but I’ve benefited from reflecting on my week as well. Numbering the weekly reflections has helped me appreciate how much time has passed. I’ll continue doing these posts even when I’m not working from home anymore. Look for them to be renamed in ’21.

Week thirty-four was an interesting one. I’m ready for the election to be over so I can get back to focusing on other things.

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