For many years I never thought about my title at CCAW. When people asked, I called myself the president. In truth, I was focused on moving the company forward and didn’t much care about a title. For some reason “CEO” never sat well with me, so I settled on president.

Today I had an enlightening conversation with other founders about titles. Here are a few takeaways:

• External vs. internal – Most internal people know who’s doing what, but others don’t. For this reason, titles (or the impressions they create) matter to outsiders.
• Business partners – Having co-founders adds another element to things. The distinction of an appropriate title is great, but defining in writing who’s responsible for what is the key to accountability, which is essential.
• Title sharing – Some founders share a title with their business partner. Think co-CEO. It’s uncommon, but it can help with transition planning. It gives a rising person the opportunity to learn under the mentorship of a person transitioning out. They can work side-by-side for a while, smoothing the transition.
• Responsibility – Titles are important to some people, and there’s nothing wrong with that. It’s only a negative when they lose sight of or don’t understand their responsibilities. Understanding your role in the company is step number one in setting yourself up for success. Focus on that.

Today’s conversation was great, and I loved hearing other people’s ideas. I’m still not much of a title person, but it changed how I think about this topic. My key takeaway is that what’s being asked of you is more important than what you’re called.

This week, I’ve listened to two founders who are targeting enterprise companies as customers. One, “Alan,” landed a major one with no product and a pitch deck. The other, “ Bob,” has a working product but hasn’t yet been able to persuade anyone to use his platform (which is great, by the way). The big difference? Relationships.

Alan has years of experience and relationships with people who trust him. He leveraged them to land his first customer. Bob is solving a problem in a space where he doesn’t have relationships or experience. He has to earn the trust of potential customers, and that takes time. Alan has founder–market fit; Bob doesn’t. This doesn’t mean Bob won’t be successful; it just means he may have a tougher journey. I learned this lesson the hard way when I was a founder.

Many factors increase or decrease the chance of success. Founder–market fit is one of them. If you’re an aspiring founder with an idea but no founder–market fit, ask yourself if you’re the right person to solve the problem. If you believe you are, forge ahead!

Today I attended Outlander Labs’ Speaker Series. This month’s speaker was Hamet Watt. He has a diverse background that includes being a venture capitalist and entrepreneur. He’s currently CEO of Share Ventures, a venture studio, and used to be co-founder and chair of MoviePass. Here are a few takeaways from today’s conversation:

• Harmony vs. consensus – Harmony on a team is good. It means people respect each other’s opinions. Consensus in decision-making ends in watered-down decisions. The drive to consensus smooths the sharp edge that’s needed for a good idea or decision to get traction.
• Instincts vs. conviction – Founders need great instincts more than they need conviction. If they don’t have good instincts, they’ll be convinced of the wrong things.
• Energy – It’s important for founders to manage their energy. Sometimes you have to sprint . . . but to finish the race, you must pace yourself. You need to be able to continue running even after hearing “no” over and over again. Hamet views this as a mostly mental trait.
• Prioritization – People who ruthlessly prioritize to get things done make good founders. They understand everything won’t get done, but they’re sure to complete mission-critical tasks.
• Conversations – Investors want to have conversations; they don’t want to be pitched. Investors are human beings who want to partner with people. Hard to do that if communication isn’t bidirectional.
• Ideal investor – Founders should look for investors who allow them to be themselves. It’s easier over the long haul to work with someone who accepts you and sees your personality as a strength.

Hamet has a unique perspective on things and it was interesting to hear him explain it. He also shared an interesting story from his MoviePass days.

I’m excited for Hamet and Share Ventures and can’t wait to see the businesses he helps start!

This past weekend, I had an issue with an expensive product I purchased a year ago. I was frustrated that it was defective and worried it might be out of warranty. I called their customer service number on Saturday morning and had a pretty good experience. I sent a few pictures while I was on the call. The rep offered to send me a replacement free of charge and alternatively gave me the option to upgrade to the latest product for a small upcharge. In the end, happy they stood by their product, I decided to upgrade.

A lot of companies focus on getting the customer and closing the deal. I’m of the opinion that how you treat the customer post-transaction is equally as important. Giving your customers a satisfying experience after the deal is how you establish loyalty and turn them into evangelists. In my situation, this company has probably gained a customer for life because of the way they resolved my problem. That’s what I’ll remember, not the problem.

Regardless of the stage of your company, remember to treat your customers well after the sale. Doing so will help you build a base of loyal repeat customers you can count on!

A founder once asked me a question that caught me off guard: “Did you have trouble sleeping when you were building your company?” As soon as he finished asking the question, I knew exactly where the conversation was headed. “Yes,” I said. He told me he’d started waking up in the middle of the night thinking about his company and had a hard time going back to sleep.

He’s not the only one. When my company began to grow rapidly, I started waking up in the middle of the night. At first I didn’t pay much attention to it, but eventually I noticed a pattern. I’d be exhausted from a long day and go to bed at a normal time. I’d sleep hard and then wake up around 3 or 4 with my mind racing. My thoughts usually revolved around two things. One was whatever I was most worried about . . . the thing that might sink my company. The other was ideas. It was weird, but I’d have a burst of ideas when I’d awaken in the middle of the night.

Sometimes I was able to go back to sleep and sometimes I wasn’t. Eventually, I realized that not getting enough sleep wasn’t good for me and was affecting my productivity during the day. I decided to do something about it. I researched sleep (including mattresses) and began working out again. I created the ideal sleep setup (or so I thought), and I had an outlet for stress and a regularly scheduled time when I couldn’t think about work (or I’d drop a weight on my foot). I eventually began sleeping through the night again. My energy level and productivity increased.

During that period, I asked a few founder friends if they ever woke up in the middle of the night. I was surprised to learn that a lot of them did. How they dealt with it varied, but the theme was consistent: they’d be thinking about their company as they lay awake in bed.

I’m not a sleep expert, so I can’t give advice about sleep to founders. I will say that I slept better and was a more productive founder when my routine included two things: scheduled time to release stress and intense focus on something besides my company. The latter is harder to achieve. Luckily, working out checked both boxes for me.

I recently told a close friend about a personal investment I made. We’ve always had a shared interest in the area. It’s not the type of investment I’ve made in the past, so he was curious. Why do I think it’s a good investment? he asked. What were my thought processes leading up to the decision to invest? How did I get comfortable with an investment far outside my comfort zone? Here are a few things I told him:

• Close-to-unique opportunity – In 2020, I told myself that I want to take advantage of a certain kind of opportunity. I listed my criteria and have been looking for matches. I felt this investment is one of those opportunities, which don’t come around regularly.
• Confidence – I wasn’t 100% confident before pulling the trigger. I asked myself if this opportunity met my criteria. It did. Even so, I was still only 70% confident. Most investments carry risk, so I’ll never be 100% comfortable and I’m OK with that (for now).
• Upside – As with lots of investments, this one could drop to zero. If it does, I’ll lose what I invested—nothing more. On the other hand, I knew there’s a big upside potential—if I didn’t invest, the gains I would lose out on could be enormous. I’m focusing on the upside, not the downside.
• Calculated risk – I didn’t bet the farm—only an amount I can bear to lose.
• Learning – Regardless of the outcome, I’ll learn more having made the investment than I would have watching from the sidelines. I guess I could look at it as an expensive education if things go wrong. I’m OK with that too. It could help set me up for a great investment in the future or avoid a disastrous one.

I’m glad my friend quizzed me about this investment. Explaining it to him highlighted some things I hadn’t thought about. I hope this turns out well!

Today marks the end of my fiftieth week of working from home (mostly). Here are my takeaways from week fifty:

• 365 consecutive posts – I’ve been sharing my thoughts via daily posts for a year. That’s a long time. Never would have dreamed I could do something like this. I’m going to reflect on everything I’ve learned from this experience.
• Time blocks – This week I had more blocks of concentrated time available, which was helpful. I was able to make progress on some things that require deep thought. Too often, I block out time on my calendar . . . and then fill it with meetings! I need to do a better job of not doing that.
• Learning – I’ve begun working on some things I don’t have experience in. It’s making me a bit uncomfortable, but I want to close this gap, so I’m leaning in. Looking forward to a time when I’ll know what I’m doing and feel confident and comfortable.

Week fifty was fast-paced. Next week is likely to be, too—I (happily) anticipate making progress in some areas that are important to me.

Many years ago, I was explaining what my company did to a good friend. All she knew was that I was an entrepreneur building a business. My explanation included details about the industry and lots of industry jargon. At the end of it, she said, “I don’t really understand what all that means or what you do, but it sounds cool. I hope it turns out well for you.”

This week I spoke with a founder who made the same mistake. After listening to him pitch his company, I still wasn’t exactly sure what it did. Conveying what you do in simple terms is important, and it’s usually a sign of a strong founder. Making it easy to understand what your company does and how it creates value for customers is the first step in getting people to support it.

All those years ago, when I heard my friend’s feedback, I backed up and rephrased. “We help connect consumers to hard-to-find auto parts using technology.” That time, she got it! And she gave me the names of a few people she thought I should connect with who could help my business.

If you’re a founder or considering entrepreneurship, make sure others can understand what you do. If they don’t, simplify it.

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A few months ago, I met with a founder who asked my opinion on the current state of his company. I said the salaries he was offering were large for an early-stage startup. The people earning them were qualified and deserving, but the company couldn’t afford-big corporation salaries. It was burning too much money every month and needed to double or triple for that level of payroll to make sense. I told him that I projected he would need to either reduce salaries or raise cash.

I caught up with him this week. He told me that he’d just survived a near-death experience. The company is still growing, but the high payroll caused him to run dangerously low on cash. He reduced his team’s salaries, parted ways with some team members, and raised emergency capital. Doing all of that at once was painful and stressful for him and his investors. It taught him to make a point of having a good sense of the trajectory of his company at all times and to make tough decisions early to avoid getting so close to the abyss.

I never raised outside capital for CCAW, but I did have near-death experiences. I concur with this founder: try not to let this happen. They’re awful. They took a toll on my team and me. Some are unavoidable and you have to do the best you can with the hand you’ve been dealt. (A global pandemic comes to mind.) Others are entirely avoidable.

Founders should always have a finger on the pulse of their company. If this isn’t one of their strengths, they should have at least one person on the team who can fill this gap. It sounds crazy, but so much happens so quickly that it’s not unheard of to wake up and realize you’re almost out of cash. The company’s heart just stops beating, and it may be too late to resuscitate it.

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Today marks my 365th consecutive day of sharing my thoughts. Exactly one year ago, I began posting because of a friend's challenge. Little did I know the impact that decision would have. Our sixty-day challenge has gone on for a year and counting.

Thanks, Ethan, for encouraging me to share more. I never would have gotten to this point without your suggestion. I’d also like to say thank you to everyone who’s read any of my posts. Your time is valuable, and I appreciate your spending some of it with me. I hope they were helpful and added value to your life.

Posting over the last year has been one of the most challenging, but also fulfilling, things I’ve done in a long time. It’s become something I look forward to and plan to continue!