I never raised capital at CCAW, but I do remember having conversations with investors. They weren’t looking to invest, but they wanted to better understand the business. I vividly remember the nature of their questions. They asked about the most private, guarded details. Things no one else asked about (or knew to ask about). How much of the company do you own? How much cash do you have on hand? What was last month’s revenue? The questions always made me feel a bit uncomfortable. Not because I didn’t know the answers; I did. It just felt weird giving detailed information about my business to someone I’d just met and might never speak with again. It made me feel vulnerable.

In the end, I’m glad I was asked and answered these questions. My answers helped the investors benchmark my company against other companies they evaluated. They were able to point out the areas in which I was doing well—and the things that concerned them. The true value of their feedback was why they felt the way they did. They were able to explain what they’d seen with other companies (or their own companies if they were former founders). I was able to essentially learn from the experience of other founders (albeit through investors).

If you’re a founder looking to raise capital or get outside opinions about your business, get ready to feel slightly vulnerable and uncomfortable. If you’re talking with credible investors or former operators, they will ask tough questions. Rest assured that being forthcoming in answering them is likely to result in good things for you and your business. Get comfortable being uncomfortable—it means you’re learning!

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Today marks the end of my forty-eighth week of working from home (mostly). Here are my takeaways from week forty-eight:

• February – February was a busy month. January felt like an off month—for me and most people I know. We just weren’t as active as usual. But February was different. Most people I spoke with felt like things returned to normal. Looking ahead a bit, I’m anticipating a busy summer.
• Deals – This week Terminus raised $90 million at around a $400 million valuation. Another huge deal for a great Atlanta company. I know there are rumblings about the sustainability of valuations, but I think this trend will continue.
• Valuations – I’ve had a few conversations about valuations this past week. Not just of start-ups, but all asset classes. This topic seems to be top of mind for many people. Not sure what will happen, but I’m confident it will be watched closely all year.

Week forty-eight was a productive one. I worked at a brisk pace, and I feel like I closed the month out on a high note. Looking forward to March.

Today marks the end of my forty-seventh week of working from home (mostly). Here are my takeaways from week forty-seven:

• Compromise – Getting everything you want all the time sounds good, but achieving something great is usually the result of compromise. This week was a reminder of that.
• Weather – The weather was extreme this week in many parts of the country. I’ve talked to friends and family enduring unimaginable conditions. I hope that everyone who’s affected by all this weirdness will soon be able to feel safe in their homes and return to normalcy (whatever that looks like).
• Relationships – Other people’s help has been instrumental in my journey so far. This week was a reminder that healthy relationships are bidirectional. It made me appreciate my relationships and look for ways to add value to others’ lives.

Week forty-seven was about focus. I worked steadily and was productive. Next week, I hope to replicate that.  

Today marks the end of my forty-sixth week of working from home (mostly). Here are my takeaways from week forty-six:

• Tools – I often look for tools to help make me more efficient. I was reminded this week that I should take the time to learn the tools I use. A great tool that isn’t used properly is of limited usefulness.
• Accountability – We don’t always want it, but we always need it. Another reminder this week: accountability is key to outsize success. I do a decent job holding myself accountable, but I push myself more when I’m accountable to someone else.      
• Culture – I had a great conversation with a friend about how working from home will affect company culture. I believe that workforces working from home exclusively or for long periods will have a negative impact on culture. My friend does too. I’ll be watching this and discussing it with company leaders throughout the year.

Week forty-six was a hectic one. It’s over now. Whew!

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

• January – Today was the last business day of the month. January was an eventful month full of extremes. It felt like an extension of 2020 with a twist. I’m curious about whether we’ll continue to see extremes the rest of the year.
• Work from home – I worked exclusively from home this week. It wasn’t terrible—but it wasn’t great, either. A change of scene is important to me and I definitely notice when I don’t get it.  
• Wall Street & Main Street – Developments in the stock market this past week were astonishing. And I think the situation is far from over. In what direction will this saga go? What topics will it put at the forefront of popular culture? I hope it doesn’t lead to a repeat of 2008 and 2009.
• Ideas – Had some great conversations this week about some ideas I’m excited about. Looking forward to working with others to put some of them into action.

Week forty-four was pretty crazy—normal for me personally, but historic and extreme at a macro level.

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

• Optimistic – I’m not sure how 2021 will play out, but I’m optimistic. I’m hopeful that we’ll begin to trend in a positive direction. I know the country’s problems won’t be resolved overnight, but it appears we’re pointing the right way.
• Work from home – I may soon return to working exclusively from home. I’m not excited about this, but it may be the prudent decision.
• Year of change – I’ve had a few conversations with people close to me who are considering making big changes in their lives. This year, 2021, may be a year of change for a lot of people.
• Groove – It’s been hard for me to settle into a good working rhythm since the holidays. I’m hopeful that next week I’ll have my groove back.

Week forty-three was a short week because of the Monday holiday but otherwise pretty normal (well, what passes for normal these days).

Today marks the end of my forty-second week of working from home (mostly). Here are my takeaways from week forty-two:

• Schedule – I thought about my schedule in 2020. There were some things I liked about my schedule but others I didn’t. I’ve adjusted it a bit and am blocking off bigger chunks of time. I’ll see how this works and finalize something at the end of the month.
• Community – I’ve been thinking about community and talking to people about it more. It’s top of mind for people personally and professionally. It’s a real problem—that is, lack of community in this pandemic age is a problem—that people are actively trying to solve in a safe way.  
• Founders – I enjoyed my conversations with founders this week. Their energy and passion was refreshing.

Week forty-two was a steady week. Looking forward to celebrating (virtually) the MLK holiday on Monday.  

The journey of an entrepreneur is one of constant experimentation. Some experiments will succeed and some will fail. Regardless of the outcome, entrepreneurs will have many learning opportunities along the way. When I think about it, what propelled my founder friends to success was learning. Not the ability to learn, but the speed at which they learned from experiments and applied those learnings going forward.

A close friend had a marketing business focused on small businesses in a particular niche. He worked closely with his clients to learn their challenges in acquiring customers. Soon, he realized that one of their specific problems was shared by tons of other small and medium-sized businesses. He experimented with solutions until he found one his customers valued. The rest is history. Today that company is valued at hundreds of millions of dollars.

Everyone can learn, but great founders learn quickly and apply their new knowledge quickly. The next time you wrap up a project (whether the outcome was good or bad), make it a point to look for takeaways and think about how you can apply them in the future. If you do this regularly, you’ll learn rapidly and increase your chances of success.

Today marks the end of my forty-first week of working from home (mostly). Here are my takeaways from week forty-one:

• Weekly reflection – These weekly posts were originally intended to document my experience of working from home during the COVID-19 pandemic. They’ve done that and more. They’re now a way for me to reflect on the week, which I really enjoy. I’m renaming them to reflect this evolution.  
• 2021 – This year is off to a crazy start. I was mentally exhausted from all the extremes in 2020. I hope these first five business days aren’t an indication of what we can expect for the rest of the year.
• More deals – This week Salesloft raised $100M at a $1.1B valuation. Another great Atlanta company doing a huge deal! I expect we’ll see more deals in the first quarter.
• Slow start – I had almost two weeks off and it was hard to get back into the swing of things this week for a variety of reasons.

Week forty-one was a crazy busy week. I’m hopeful that it will turn out to be the exception rather than the norm.

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

Today is the last day of my holiday vacation. This is the first time since I became an adult that I haven’t traveled for Thanksgiving or Christmas. Compelled to stay home by the pandemic, I spent time recharging. I’m not happy about not seeing my family, but this quiet holiday was a much-needed break after a hectic 2020. The year was full of so many extreme changes that I think I was mentally worn out. The unusual holiday gave me a chance to recover from 2020.

Change is good and I embrace it, but 2020 has taught me to be aware of the magnitude and number of changes and the time frames they occur in. I’m sure 2021 will be another year of change, but I’m hopeful that it will be more moderate.