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.

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.  

Today I spoke separately with an investor and a founder who both mentioned how timing beyond their control had an big impact on them.

The investor has been at it for many years. When he started raising his first fund, it was tough because his thesis didn’t resonate with many people. Today that same thesis is popular and has allowed him to raise his latest fund quickly.

The founder has been solving a painful problem for years. When he began, his target customers weren’t open to a digital solution (yes, industries like this still exist). The pandemic has forced them to adapt, and they’re readily using his digital solution.

These two people haven’t changed what they’re doing. They’ve stuck to the same script. The difference is that the timing is right—the market now values what they’re doing.

Make no mistake. Timing is a big factor in success. It may not determine success, but it heavily influences it. Unfortunately, people are usually at its mercy. Everything can be right except the timing, and there’s not much you can do about it. We can’t control timing, but we can be aware of it and act accordingly. I’ve seen founders know they were on to something big but also aware enough to know the timing wasn’t right. Some of them chose to spend their time and energy on something else. Others worked on perfecting their solution until the timing was right. I’ve seen both approaches lead to success. The key was awareness, which allowed them to make proactive decisions that factored in timing.

The next time you’re trying to do something, ask yourself, “Is the timing right?”

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.

In my post yesterday, I shared my thoughts about success requiring not only luck (preparation + opportunity) but also the ability to recognize an opportunity and the willingness to act on it despite the risks inherent in doing so.

Today I had a chat with a close friend about people’s mindsets. We talked about how important mindset is to outsize success. Your mindset can prevent you from taking action when you get a lucky break—even when it’s staring you in the face.

I’ve noticed a pattern in the mindsets of people who’ve achieved big successes. They realize they could fail. The time and energy—not to mention money—they put into something could be all for nothing. Yet they don’t dwell on that. They accept it and focus on the upside potential. If everything goes right, how big could this be? They look for opportunities that have massive upside.

The next time you get a lucky break or evaluate an opportunity, be aware of your mindset. (In other words, think about how you’re thinking . . . something, it’s believed, humans are uniquely able to do.) Take a second to ask yourself: if everything goes right, how big could the upside on this opportunity be? The change in mindset could lead you to outsize success!

Someone made a point in a debate I listened to today that gave me pause. He said luck is what happens when preparation meets opportunity. The Roman philosopher Seneca said that first, and I agree with him. The debater took this one step further, though. He said you have to be willing to take risks to capitalize on luck. He gave the example of a backup quarterback who practices hard and is ready when the starting QB is hurt. The backup gets a lucky (for him) break to show what he can do on the field. But playing involves risks that he must accept to take advantage of his luck. He could fail by performing poorly (this trips a lot of people up) or being injured.

I spent more time thinking about this and I generally agree with what was said today, but think they missed something. In speaking with entrepreneurs (not just techies) and investors who’ve had outsize success, I’ve noticed a distinct pattern. They all have the ability to recognize when they’re in a lucky situation and take action—rapidly, if they’re among the best. (Most lucky situations aren’t as obvious as the backup QB’s was.) Sure, things can go wrong, but they mentally set that possibility to the side, focus on the upside, and accept the risk.

When I think about what it takes to succeed, I view it as a two-step process:

·     Preparation + Opportunity = Luck

·     Luck + Recognition + Action (i.e., accepting risk) = Success

Following this two-step process doesn’t mean you’re guaranteed to be successful. But being aware of it will make success more likely.

If an athlete practices hard and finally gets the chance to play, that’s not enough. He has to jump at the opportunity, play his best, and risk failing or being injured. Otherwise, his luck isn’t going to lead to success.

This week I caught up with an entrepreneur working on an interesting problem. When we first met months ago, he had just launched his MVP and was targeting both corporations and consumers. This immediately stood out to me. He was trying to serve multiple masters.

Corporations and consumers are totally different types of customers. Their needs are different and the sales processes used with them are different (if the solution isn’t self-serve). It’s certainly possible to have both as customers—if a company has adequate resources. Early founders should use limited resources wisely and efficiently.

This founder shared his 2021 plans with me. His team developed annual goals and strategized on how to achieve them. The data told them that targeting a specific consumer profile would likely be their best path. The founder also got feedback from his team that to provide an ideal experience to a broader customer base, they would need more resources. The founder listened. He narrowly defined the company’s target customer for 2021. His team rejoiced!

It’s hard for companies to be everything to everyone, especially in their early days. If you’re an early founder, consider focusing on one type of customer and one solution first. You don’t hear about many companies failing because they solved their customer’s problems too well or exceeded their expectations.

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.

I’ve seen founder friends build massive companies that started with a simple goal: to improve workflow. They took a manual process and developed software that made it simpler, more visible, and more conducive to collaboration. This great startup approach for nontechnical founders can be the secret sauce that propels a company to success.

Today I met with a founder who’s pursuing an idea about improving a very specific and highly technical process involving lots of parties (internal and external to the company). The costs of errors to many stakeholders are high. He’s spent over a decade learning the space and has deep relationships (his unfair advantage). He has a unique insight that differentiates his solution from that of competitors. And he’s built an early version of his product to test with customers. This founder is well positioned to build a large software company by making a specific process easier for his target customers.

I’m not an idea person, nor are many other founders. Fortunately, you don’t have to be brimming with creative ideas to be a successful founder. Aspiring founders can easily find ideas that could lead to terrific companies by looking around for inefficient processes that take tons of time or cost lots of money to execute. The more painful the better! The next time someone is complaining about something that annoys them about their job, listen. It could be the seed you need to grow the next billion-dollar workflow management company.

I’ve previously shared my thoughts on founders feeling like they have to come up with an Amazon-caliber idea to start a company. That’s a path, but there are others. I often meet with entrepreneurs who aren’t idea people but still make it work. They find (or stumble upon) a problem they want to solve. They research who else is solving the problem and learn how effective their solutions are in the eyes of customers. If customers are only partially satisfied, they set out to close the gap. These entrepreneurs don’t dream up a completely new solution; they make a better iteration of what’s already out there. They know what customers like and don’t like about it, so it makes sense. There are countless examples of companies like Facebook, Zoom, and others who used a similar playbook, and for good reason . . . it works.

If you take this path, you need to acknowledge that’s what you’re doing. When you explain your solution and vision, your pitch will go over much better with investors and recruits if you acknowledge that you have competition and articulate precisely how they fall short of customers’ expectations. You’ll be demonstrating that you have a unique insight that the market has missed. Your unique insight differentiates you from your competitors and will become the flag that others rally behind in support of you.

Unless you’re creating a new market, you have competition. Find a way to understand what your customers think of your competitors’ product or service. Being able to articulate this insight clearly could change the trajectory of your entrepreneurial journey!