Yesterday I spoke with a close friend about the current business landscape. He’s an avid investor and regularly trades his own stocks. Throughout the day, he checks the market’s performance, and he always knows how each of his positions is performing. The conversation turned to the market downturn and all the negative economic news. I asked him how his portfolio was doing, and to my surprise he said he didn’t know. I probed a little more and he admitted being too scared to look.

Reflecting on this, I realized I had once done something similar. Every morning at CCAW I was provided with and reviewed a series of reports and metrics. They detailed our current state (MTD revenue, cash position, A/P balance, etc.) and projected our future revenue and profitability. These reports were critical to my understanding of our current performance and where we would probably end up. If I didn’t like our trajectory, I could be proactive and initiate actions to change it.

We had a rough patch when we were constantly being hit with bad news. Week after week, macro things were happening that affected us negatively. After a while, I stopped reviewing the daily metrics and reports. I told myself I was too busy and tired, but the truth was that I didn’t want to see the data quantifying how bad things were.

I realized that I didn’t have the experience to navigate these rough waters on my own. I owed it to the team to do better, so I hired an advisor with experience in grappling with challenging business environments. One of the first things he asked me was how bad it was. I told him it was bad, but I didn’t have exact numbers because I hadn’t looked at the data. I expected him to chastise me, but he told me that was normal. (In fact, he had done something similar when one of his companies struggled.) It’s human nature, he said, to avoid bad news during difficult times. He encouraged me to start looking at the data regularly and discuss it with him. I did.

Takeaways:

• Don’t avoid – A bad situation doesn’t get better because you avoid it. Look at important information regularly so you can make better decisions.
• Data availability – If you don’t consistently have access to critical information, you can’t plot a course. Consider taking time to put processes in place to make that information available.
• Communication – Whether your numbers are good or bad, share the news. People will appreciate not being kept in the dark. You never know—someone may have an idea that could change things.

Have you ever found yourself avoiding during a difficult time? If so, what did you learn?

Today marked the end of my first week working exclusively from home. My normal routine has always included working at home part of the time, but until now I’ve worked mostly in an office.

Here are my takeaways from week 1:

• Physical activity – I like being active and usually work out in a gym. Since I couldn’t do that (thanks, coronavirus), I adjusted by taking up running outside (I hate running). Surprisingly, I enjoyed the fresh air and constantly changing scenery.
• Time – Not having to take time to “get ready” and then commute was refreshing. I had more productive time.
• Social interaction – Not being around people affected me initially, but video calls and meetings provided enough social interaction for me to feel normal.
• Meals – I typically have lunch with friends or colleagues a few times every week. I didn’t care for not being able to. A friend mentioned they had done a virtual lunch via FaceTime. I haven’t tried it, but I may if this becomes the new norm.
• Focus – There are distractions at home, so I have to make more of an effort to focus on work.
• Separation – Traveling from my office to my home has always helped me shift my mindset from work to my personal life. Now, I must create that separation within my home. Having a dedicated home office has been helpful.

During this first week, anyway, working from home all the time hasn’t been as bad as I imagined. I’ve learned what I need in order to feel normal, and I look for alternatives that work in the current environment. I pay attention when people mention what they’re doing to help their teams adjust to working from home (for example, video happy hours and breakroom channels in Slack). I can't control this situation, but I can make the best of it. I plan to learn from this, adjust as necessary and share my experience with others.

Today I participated in a conversation among successful entrepreneurs in a variety of industries about COVID-19’s impact on businesses. COVID-19 is bringing crisis to most companies.

As we talked, I reflected on a perfect storm in my past. Macro political changes were negatively affecting my business, a member of my immediate family had an unexpected life-threatening medical situation, and I was facing personal headwinds with the potential to upend my private life. It was not a fun time. The stakes were incredibly high across the board. One bad decision and life could spiral out of control quickly. I was stressed, to say the least.

I learned things then that I shared today:

• 80-year-old’s lens – Fifty years from now, when I’m in a rocking chair telling my story, what will matter most? Relationships, not accolades or wealth. I needed to align my current actions with this future perspective.
• Priorities – I’m only human. My time and energy are limited, and I can’t be effective in every domain at once. Viewing things through the lens of my elderly self, I prioritized the headwinds pushing at me and put family first. I got comfortable with the idea that other balls would drop and things would get ugly before they would get better.
• Communication – I couldn’t immediately focus on lower-priority headwinds, and there were people I cared about who would be affected by that. I clearly explained my thoughts to them. Some agreed with my priorities and appreciated my honesty. Others were extremely upset. I made sure they all knew what my top priority was, how I would be allocating my energy, and how I came to that decision.
• Focus on the light – I focused on the light at the end of the tunnel, not the darkness of the tunnel I was in. I figured that once I was out of the tunnel, I’d have plenty of time to reflect on why I’d been in it.
• Experienced advisors – I pulled together an informal group of people I respected who had experience in areas in which I was inexperienced (I even sought out and paid one person). I asked them to share their experiences with me and incorporated them into my decision making.
• Emotional control – Emotionally, I was riding a rollercoaster. But I was purposeful and made sure my emotions didn’t dictate my decision-making, my actions, or my words. I took time to talk through my decisions with people I trusted and asked them about my blind spots before I took action.

Did everything turn out perfect? No. Was the process painful? Yup. Could I have done some things better? Absolutely.

In the end, it all worked out. It took a while, but looking back, I’m happy I addressed each headwind separately. The passage of time with no action on some of these problems made them worse in the short-term. But what I would have gained from trying to solve them all simultaneously would have been outweighed by the toll it would have taken on me and the people around me. I don’t think this approach would work for everyone or every situation, but it worked for me in that perfect storm.

If you find yourself buffeted by a perfect storm (and you will if you’re an entrepreneur long enough), take time to think. Navigate it your way—not someone else’s way—consistently with your ethics and morals.

Today I had a conversation with a friend and fellow founder who’s active in the Atlanta start-up community. We shared our views on the macro landscape and what it means for the entrepreneurial community locally and nationally. Here are some of our takeaways:

• Communication – Founders should communicate often with their teams, investors, banks, and partners. If you don’t have all the answers, communicate what you do know. There’s nothing worse than being in the dark, at risk of being blindsided, during a time of crisis.
• Capital – Capital will be less abundant. I assume that banks will honor previously extended credit, but they probably will be reluctant to extend new credit. Venture capitalists are also likely to pull back in the short term until it’s clear how (IPO, M&A, etc.) and at what valuation they can exit their investments and return capital to LPs.
• Delayed closings – Venture capital deal closings could be affected if LPs default on capital calls. If this occurs en masse (which I believe is unlikely), VC deal activity will slow.
• Contingency plan – Start working on a plan and define the thresholds that will trigger it. It’s better to have a plan and not need it than be caught without one.
• Experience – The last economic downturn was more than a decade ago. If you didn’t experience it, seek out entrepreneurs who survived it and learn from them.
• Cash is king – Monitor your balance daily.
• Accounts receivables – Know who owes you, how much they owe, and when their payment is due. Reach out to each customer with a past-due account to gauge their ability to pay.

The business landscape is changing at an unprecedented pace. I encourage entrepreneurs to be proactive. If you’re an entrepreneur who lived through the last downturn and you have bandwidth, I encourage you to reach out to other entrepreneurs. Sharing your experience or just lending a listening ear could change someone’s trajectory.

Today I met with an entrepreneur who’s starting a SaaS company that will automate business processes for small and medium-sized businesses. He’s considering raising venture capital to build the technology, so my experience developing CCAW’s technology without raising capital interested him. Bootstrapping admittedly made it ten times more challenging. Here are some of the things I shared:

• Platform as a service (PaaS) – We couldn’t afford to develop or maintain the infrastructure underlying our applications, so we used a PaaS provider. It worked perfectly. One major downside was not owning 100% of our intellectual property.
• Spaghetti code – A high-profile investor recently told me that most early-stage companies he’s invested in were built on spaghetti code that wasn’t improved until later financing rounds. Duct tape and bubble gum are OK early on, when technical perfection is unreachable.
• Technical wisdom – I’m not technical by training, so bringing in a senior technical person was a game-changer. I could describe how I envisioned our system working and rely on them to make it happen.
• Technology wasn’t our product – Our revenue was generated from sales of physical products. With our technology, we consistently sold ever-larger quantities of them. If our revenue had come from selling technology, we might have chosen a different approach.
• Testing – We tested things manually to gain clarity about what exactly our engineers needed to build. Test before committing tons of engineering resources (if possible).

This approach worked for us and allowed CCAW to scale. Every business must forge its own path but whatever direction is chosen, technology costs have plummeted so much in recent years that more can be done with a fraction of the capital. AWS, Azure, Google Cloud, and Salesforce are just a few of the cost-effective options available. I encourage new entrepreneurs to think creatively about how they build their technology.

As I write this, the coronavirus pandemic is forcing companies to rethink how their employees work. They must embrace the work-from-home option like never before. I managed a mixed team of remote and in-office workers at CCAW, so I thought it might be helpful to share what I learned:

• Right person in the right seat – This is important wherever the seat is located, but it carries extra weight for team members who work from home. Make sure the person you hire is a good fit for the job.
• Experience – Seasoned team members tend to do better in remote roles. They often (but not always) need less hand-holding to work productively.
• Video communication – You can never replace face-to-face conversation, but video tools like Zoom are the next best thing.
• Cadence – Weekly or even daily team stand-ups keep information flowing and help resolve issues quickly.
• One-on-one meetings – Regular meetings with each remote worker are critical. They give the team member a chance to say what they’re thinking (good or bad) and connect personally with their manager. We did our meetings weekly.
• Alignment – Communicating what’s going on with the company is difficult. We published dashboards displaying key performance indicators (KPIs). We then discussed the KPIs during our regular meetings.
• Chat – Tools like Slack that allow you to create rooms or channels are great for communication. People like sending quick messages instead of emails.
• Visibility – Knowing who’s working will help you set expectations for responsiveness by remote team members. Tools like TSheets can help.  

It’s hard to replace the in-office experience, but there are things you can do to make everyone feel welcome and be productive. When done well, remote work raises team morale in a big way.

I wrote a post about why I wasn’t scared to leave corporate America. In that post, I committed to providing a detailed list of all the factors that allowed me to transition without fear. Here’s the list:

• What could go right – I focused on this, not what could go wrong.
• Superman syndrome – I hadn’t yet experienced any serious professional failures and basically thought I was invincible (typical early 20’s mentality). Note: I experienced many failures and was humbled many times over while building CCAW.
• Experience – This would be my second “official” company. My prior startup experience, my education, and my corporate experience made me “feel” much more prepared this time around.
• No career path – There was a clear path to being an EY partner in 15-20 years. The downside is that it is (or was back then) an up or out career path. You progress, yearly, towards partner, or you’re out. I didn’t want to be a partner, so I knew my days were numbered.
• Can’t hit what you can’t see - Working in a large company and with other large publicly traded clients gave me a clear idea of what well-run companies looked like. I knew what I was aiming for and felt confident I could replicate it. Side note: They look like well-oiled machines from the outside, but they’re not. There’s always a fire drill, crisis or some critical system failure when you peek behind the curtains.  
• Financially de-risked – I was traveling a ton, so a large percentage of my expenses were paid by EY. I also had two roommates. This allowed me to save a sizeable cushion. Feedback from others heavily influenced how I came up with this plan.
• Business de-risked – I actually started working on CCAW while still employed and using EY resources (which was probably against company policy). I was able to build relationships with suppliers and gain traction with customers before quitting.
• Reputation – I made sure I did a stellar job on all projects and got along with all team members. I never wanted to burn bridges or have a bad reputation. I wanted to leave on great terms.

Looking at this list now, it gives the impression that I was this well-thought-out young person. I wish that was true. In reality, I wasn’t. I was actually stretched super thin and all over the place (literally, too, since I was traveling every single week). What I was actually doing was staying true to my passions (entrepreneurship and personal finance), staying true to the values instilled in me by my family (do your best, treat people well and never burn bridges) and throwing stuff at the wall to see what stuck. Mix in a little luck and good timing and I found myself in a position to take a leap of faith.

Takeaways:

• Venture capitalists like betting on people with entrepreneurial experience. I now understand why. If you have an idea, give it a shot (even if you keep your job). You never know what could happen. Worst-case, you’ll learn a lot that can be applied to the next idea.
• My approach was the product of my young age and lack of responsibilities. However, I do think some (maybe not all) of the things I did might be applicable to others at different life stages thinking about entrepreneurship.
• Making the people who cared about me proud by taking a corporate job was nice, but my heart wasn’t in it. I’m an entrepreneur at heart. I like building things or helping people who are building things.
• Stay true to your passions and values. You never know where they’ll take you.

I previously wrote about my transition to corporate America, which people never actually ask me about. Most people are more interested in my transition to entrepreneurship, which I’ll detail in a future post. When I tell my story, people always ask me if I was scared. I always politely say no and continue telling the story. In my mind, I’m baffled and wonder, “Why would they ask if I was scared?” It never made sense to me. Recently, I reflected more on this and asked myself “Jemaine, why weren’t you scared?” For me, personally, the “why” is more valuable than the “what.” If I can understand why a decision was made or an action was taken, regardless of the outcome, I learn a lot more. Unfortunately, I hadn’t taken the time to understand “why” I, in fact, wasn’t scared to leave corporate America.

After unpacking this a bit, I realized there were a variety of reasons why I wasn’t scared. I had technically been an entrepreneur before. I knew I didn’t want to be an EY partner (great job, just not for me). I had started to de-risk my situation and my business idea, etc. I’ll provide a comprehensive list of all the reasons in a future post. My aha moment, though, was realizing the main reason I wasn’t scared was super simple: I was focused on what could go RIGHT.

People often focus on all the things that can go wrong (I’m guilty of it on a daily basis). It’s natural and part of how people assess things, but it can also be the death kiss to promising ideas if left unchecked. I was thorough in my assessment and aware of all the things that could go wrong, but I didn’t focus or dwell on them. For whatever reason, when it came to this particular decision, all I focused on was what could go right and where that could put me.

Next time you feel strongly or passionately about something, consider thinking about all the things that could go right and where you could end up as a result. You never know, the upside may outweigh the downside.

Today I had the opportunity to meet with an up-and-coming Atlanta entrepreneur, “Stephanie,” who has a growing company that she’s bootstrapped for the last three years. She recently participated in an Atlanta start-up competition and did well. Because of that exposure, local venture capitalists have shown interest in her company. Stephanie is currently evaluating if venture capital is the right path for her. It took many years, but I eventually bootstrapped CCAW to eight-figure revenues. Because of my experience, a mutual acquaintance asked me to chat with Stephanie.

I always like to start these conversations by learning about the entrepreneur’s background, business model, technology, and vision for the company. Here are some things I learned about Stephanie’s situation:‍

• ‍Solo founder – There is no cofounder or team member at her level intellectually.‍
• Scalable – Her business model is scalable—others in the market have proved it.‍
• Unique advantage – Stephanie has lived and breathed two unrelated industries for years. She’s uniquely positioned to see how linking the two can create value for customers. Others don’t realize this yet.‍
• Competition – Her business model isn’t new, but her implementation of it is unique. Highlighting this difference is critical to achieving healthy margins.

Stephanie has clarity about the destination she’s aiming for because the competition required her to pitch her destination to others. Now she has to figure out how to reach the destination quickly. She has ambitious goals, which will require a sharp team and a variety of resources. These things don’t come cheap.

In the correct situation, venture capital can help accelerate growth. Investors will also provide experience gained from prior portfolio companies, access to relationships, and accountability via a board of directors. Unfortunately, venture capitalists typically invest only when companies have the potential for outsized returns.

Everyone has to figure out what path is right for them, so my goal wasn’t to tell Stephanie what to do. Instead, I shared my bootstrapping experience—the good, the bad, and the ugly. I described the lessons I learned and the things I would do differently if I had it to do over (hindsight is 20/20).

Takeaways:

• ‍Capital source – Venture capital isn’t for everyone, nor is bootstrapping. Consider the pros and cons of all funding sources and pick the one that’s best (none will be perfect) for your company and your situation.‍
• Partnership – To build something great (a company or anything else), it’s VERY difficult to do it by yourself. Be open to partnership (cofounder, investors, etc..). Some of a lot is better than all of nothing.‍
• Timing – You can be too early, too late, or there at just the right time. Consider timing when making decisions about your capital sources or anything else.‍
• Consistent execution – When you’re executing on a growth plan, starting and stopping on the basis of cash flow—bootstrapping—makes everything exponentially more difficult.

In a previous post, I shared what I learned from my first company. It taught me a ton, but I never figured out how to transition it from a hustle to something sustainable. That realization, my desire to make my parents proud, and an urge to keep up with my classmates resulted in my happily agreeing to work for EY in Atlanta. To be totally transparent, I also wanted to move to a big city and travel on someone else’s dime. (Side note: I almost accepted a job in San Francisco —until they casually mentioned I’d probably need four roommates.)

Personal finance has been a hobby since adolescence; that was a big part of the reason I majored in finance. The summer after college, I was curious what my financial life would look like with a real job in a big city. I’d never lived outside Louisiana, earned a salary, or had benefits before. I decided to create a budget for my new corporate life in Atlanta. My forecast was crude, but the exercise was helpful. Even though I’d studied finance and read avidly about personal finance, my knowledge gap was HUGE. I decided to fill that gap and get perspective from others. My hope was that I could avoid financial pitfalls.

I decided to try to get my forecast posted on a personal finance blog and ask for feedback from its readers. Getting any response from bloggers was a 50/50 proposition, I figured, and I expected a demand for compensation if they did reply. There was no downside, though. From my previous experience, I had learned the value in simply trying.

I emailed my forecast to a popular personal finance blogger. To my surprise, he agreed to post it and didn’t ask for payment. You can see the post, my forecast (don’t laugh), and the feedback here. The feedback came in quickly and was pretty diverse. There were financial suggestions, as expected, but also advice on how to live life. All these years later, I’m still surprised and thankful that this blogger and so many of his readers were willing to help me out by sharing their experiences and perspectives. Their feedback helped me prepare for life in a new city and transition smoothly to corporate America.

Here are my takeaways from the experience:

• ‍Perspectives – Everyone views life through a unique lens. For a variety of reasons, we don’t all see things the same way. There is value in trying to understand other perspectives (even if you don’t agree with them). Listen with an open mind.‍
• Knowledge gaps – Nobody knows everything. Seek knowledge from credible sources and people. It will help you make good decisions.‍
• Right answer – The right thing to do may be something suggested by someone else. Getting to the right answer is more important than being right. This is from Ray Dalio’s book, and I agree 100%.‍
• Ask for help – People are often willing to help. Think carefully about what you’d like them to do for you. A specific ask will make it easier for them to help, so they’ll be more likely to say yes.