I had a great conversation with a good friend today. We talked about traits we’ve noticed in successful entrepreneurs. He shared some insights from his time in entertainment, while mine were from my time and relationships in tech. Interestingly, they overlapped.

• Learners – Successful people are learners. They’re aware of their gaps and actively seeking to fill them. Sometimes that involves taking on a role in someone else’s organization to set themselves up for future success . . . and perhaps more future success via their own vehicle. They set their ego aside to gain the knowledge they need for the future.
• Partnership – They recognize that they can’t do it alone and actively seek to partner with others who can help them succeed. Both bringing the right people inside their organization and partnering with the right outside people can work.
• Accountability – Successful people want to be held accountable and want their teams to be held accountable. They create cultures and put processes in place that reinforce this.

I always enjoy catching up with people in other industries and picking their brains. Today was no different. It reinforced that there are clear patterns and habits that contribute to success!

Today Calendly announced that it raised $350 million and is valued at over $3 billion. I’ve used Calendy since 2015 and am a huge fan. The team is talented and the product makes scheduling a meeting super easy. A few thoughts on this deal:

• Pandemic – The company already had an impressive growth rate, and it increased dramatically during the pandemic. They were well positioned for revenue redistribution.
• Revenue – They’re now at roughly $70 million in annual revenue. So, they’re eyeing $1 billion.
• Profitable – The company is growing rapidly and profitable—a dynamite combination.
• Hot market – The market is still hot. Investors are willing to pay higher valuation multiples for attractive growth opportunities.

Congrats to the Calendly team on a huge win! They’ve been building a great company and product for years. Can’t wait to see what happens next.

When I created CCAW, I decided to go with an asset-light business model. In so doing, I was attaching myself to suppliers and vendors. We relied on them for operational execution and inventory planning. I referred to them as partners because without them our business couldn’t operate. Knowing this, I made a point of having strong relationships with our partners. I assumed that what mattered most to them was the size of our relationship (i.e., our sales with them). I tracked sales with each partner and constantly talked about ways to sell more.

One day I was talking to an executive at one of our partners. I casually asked, “What does a great customer look like to you?” I was trying to find out if we were doing what was needed to be a key customer and be included in some of their strategic decision-making. His answer was not what I expected: “The ones that pay their bills, and on time. You can buy a ton of stuff from me, but if you never pay or pay late I’d rather you never buy from me.”

I learned that we weren’t their biggest customer, but we were a key customer because of our flawless payment history. Constantly buying inventory required lots of capital, and they had challenges with keeping everything in stock and having enough operating capital (this is the exact reason we didn’t want to hold inventory). I made calls to other partners and they all confirmed that they put a high priority on timely payments. I had assumed all companies were like us and paid on time. Wrong. We were operating in a space where people didn’t pay their bills on time.

We had great accounting processes, but I’d never thought of accounting metrics as key to our strategy. That changed. I put our payables process higher on the list of important metrics and made those metrics visible. Payables was now a huge competitive advantage we could use to enhance our growth strategy.

In hindsight, I wish I’d asked for input earlier. I was aiming for what I thought mattered most (sales), only to find out that my partners valued something different (cash flow). When we started to lead conversations with potential partners with what mattered most to them, we signed up more of them and our growth rate increased.

If you’re a founder trying to do something great, you’ll probably need help (from partners or investors, for instance). Early on, ask them what’s important to them. Don’t assume! You’ll gain valuable insights and cement your relationships with stakeholders.

Yesterday I said that benchmarking is one of the mental challenges founders face. Then today I read this:

Anyone you see succeeding is only succeeding at the things you’re paying attention to—I guarantee they are also failing at lots of other things.”

~Ray Dalio

I like this quote because it’s a reminder of why we shouldn’t benchmark ourselves against others. We often don’t have (or aren’t paying attention to) the full picture. Selective comparisons disregard the reality that failure is likely part of their story. The truth is that failure is more common than we like to admit. Even when it seems that someone is wildly successful, they’re probably failing too. And that’s OK.

Benchmarking is a mental trap that’s common among founders (and people in general). And probably more so now, in the Information Age, than ever before. (We can find out a lot about people’s successes on the web and social media—but much less about their failures.)

Try to avoid this trap. Instead of measuring yourself against an incomplete picture of someone else, pay closer attention to your own situation. Give yourself credit for your success and make it a point to not only learn from your failures but apply what you learn to future decisions. This will help you succeed, while benchmarking yourself against others will depress you. That’s not conducive to success!

I was asked to give my input on a program being developed to help diverse Atlanta entrepreneurs. I’m excited about the program and can’t wait for it to launch. The creators asked me a tough question: “What mental challenges do founders face?” The fact that they’re thinking about this and wanting to help founders address these challenges is encouraging.

Here are a few things I shared:

• Release – Founders should understand the one thing they enjoy and need outside of work to be the best version of themselves. It could be exercising, playing video games, attending sporting events or live concerts, or anything else. Whatever your thing is, make it a priority so you’ll have a mental release.
• Imposter syndrome – Founders are constantly in environments and situations where they feel they’re unqualified and unprepared to handle whatever’s going on. They often fear failing or being exposed to others as a fraud. This is normal and usually unfounded. Most people know entrepreneurs have gaps but still root them on. Not because they’re perfect or have all the answers, but because they have the courage to try to do something great.
• Benchmarking – Founders will sometimes compare themselves to their peers. This is a mental trap. Everyone’s circumstances are different. Timing also plays a huge role in success. Just because someone else is succeeding and you aren’t doesn’t mean you won’t ever. Be happy for them and know your time will come.

There are lots of other mental challenges, but these are a few that I think many founders have had to overcome. Entrepreneurship is a mental game. Going into the game knowing what to expect can . . . well, be a game changer. Entrepreneurs will be able to be more proactive than reactive during their journey. I’m excited to hear that diverse founders will get help with the mental side of entrepreneurship!

Today I met with a successful entrepreneur who recently sold his company. He shared his views on the entrepreneurial journey, which he sees as an evolution. I totally agree. My attention was caught by his term for one stage of the journey: “rebirth.” After you have the idea, build the company, exit the company, and overcome the post-exit phase (i.e., separate yourself and your identity from the company), there’s another phase. He views it as the beginning of a new chapter, which will be different for every person. It’s the “Now what?” phase.

I’ve never heard it articulated this way, but I agree with him. When you’re focused on something for a long period of time and then it’s gone from your life, there’s a time of transition. A time when you think, “Now what?” I think rebirth is a natural part of everyone’s (not just entrepreneurs’) evolving life. Parents whose children have left home. Anyone recently retired. Someone recently laid off. People who are widowed or divorced.

Rebirth can be uncomfortable, even deeply painful depending on the circumstances, but it’s also an opportunity. A chance to steer your efforts in a new direction and grow in a different way.  A renewed existence of sorts. A do-over. Whatever journey you’re on, it won’t end; it will just cycle around.

I’ve been listening to a friend talk about a deal he was considering. It was a big real estate deal, something I’m not experienced in. I didn’t have a stake in it, but I decided to help in a way that leveraged my strengths. I’m a numbers guy, so I built a crude financial model to help clarify the worst-case scenario. We talked it over and he shared his insights on what the model was saying and things it didn’t account for.

Today, I learned that the deal fell apart. Not the outcome we were hoping for, but I realized that supporting my friend had been a great experience. First, it always feels good to contribute to someone else’s success. My assistance wasn’t material (in my opinion), but every little bit helps when you’re trying to do the impossible. Second, helping my friend, who’s experienced in a space that I consider a future area of interest, was a terrific opportunity for me. I learned a lot, fast, from the combination of his wisdom and my own research.

If you’d like to learn about an area or gain some experience in it, try to find a way to offer your skills, free of charge, to someone knowledgeable. Give back by helping a friend or colleague . . . learn about something that interests you . . . it’s a win–win!

I’ve been working on a project for a few weeks. My vision was to use the most advanced tech to make it a success. I wrote down what I was trying to accomplish and began researching. Ideas for solutions came from others along the way. But my vision slowly deflated. To my surprise, my dream technology doesn’t exist. When I talked to people who live the problems I was working on, I learned they’re using manual workarounds or legacy tech. The more I dug, the more frustrated I felt.

I was forced to accept that the perfect solution I envisioned isn’t possible. So, taking a step back, I reviewed my goals for this project. This reset my perspective. I was reminded that I was looking for the solution that best checks certain boxes—it doesn’t have to be perfect. In the end, a legacy technology was the best option. It’s not slick (in fact, it’s clunky) or cutting edge. But it efficiently does what I need done. I embraced it and wrapped up that part of the project.

I was reminded of a common start-up mantra: done is better than perfect. Sometimes the best solution isn’t glamorous. It just works.

Decision-making and quick learning are keys to success. If you can learn quickly and apply your new knowledge to improve your decision-making, you’re more likely to achieve your goals. As I thought more about how I’ve observed others learn, another pattern emerged: great questions.

Whenever I meet with successful people, they ask me great questions. I often leave meetings thinking about things that had never before occurred to me. They usually don’t tell me what to do, but nevertheless they have a huge impact on my decision-making.

Great questions don’t always have to come from other people. In difficult situations, I’ve had some tough conversations with myself. I’m capable of asking myself tough questions! Where am I failing? Why am I doing this? What’s my biggest fear for this project? Answering such questions honestly has clarified things and helped me make better decisions and push through.

Great questions can lead to great outcomes. If there’s something great you want to accomplish, consider putting yourself in position to be asked great questions.  

Decision-making is one of the main responsibilities of leaders (all leaders, not just entrepreneurs). When you lead a team, others look to you for guidance. Making decisions that affect only you is one thing. Knowing that you’re affecting other people’s lives is quite another—and it makes decision-making more difficult.

I’ve had the good fortune to spend time with great entrepreneurs, and I’m always curious about how they approach decision-making. From what I’ve seen, everyone’s style is different and there’s no wrong way to go about it. However, I’ve noticed one pattern: they’re not afraid to change their mind. I didn’t know what to make of this at first. Was it indecisiveness? Lack of focus? Eventually, I figured it out: none of the above. They were learning. They allowed their thinking to evolve based on new information. They were unafraid to admit they’d been wrong and change their mind.

Some people struggle with making decisions that affect other people. And rightly so. There have been times I’ve worried about making the wrong decision, and I still struggle with it from time to time. Over the years, though, making decisions has become easier. I remind myself that they usually aren’t set in stone, and it’s OK for me to change my mind. It’s even OK to admit that I was wrong!

The next time you have to make a decision that affects others, make the best decision you can with the information available to you. That’s all anyone can expect of you. And remember: it’s OK to change your mind as you learn.