POSTS FROM 

November 2020

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Align Your Needs to Your Investor’s Style

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.

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Slow Down to Speed Up

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.

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Picks and Shovels

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?

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Losing a Deal

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.

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Working from Home: Week Thirty-Four

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.

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Bold Decisions Will Make Sense Only to You

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.

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Listening to Understand

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.

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I’m Evolving, Productivity-wise

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!

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Lingo Matters a Lot: Do Your Homework

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:

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!

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You Can’t Have It All At Once

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.

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