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

• Big vision – A few years ago, I had an idea and a vision for it. Others thought it was too big, not possible. This week they realized that my vision is possible and there’s a clear path to get there. Excited to see how this develops.
• February – This month started off at a brisk pace. I have some good stuff lined up, and I’m looking forward to the rest of this month. I think it will be a great one.
• Alignment – When people are aligned on the end game, it’s easier to trust one another. You may not agree on how to get there, but because you’re aligned on the destination, you’re more likely to try each other’s approaches. When alignment isn’t there, neither is trust. This week reminded me that alignment is important.

Week ninety-seven was a lively one. It kept me on my toes. Lots of good things came together or started coming together.

A friend shared a major accomplishment with me. He’s been working on a project for months. Pain. Frustration. Minimal progress. At times, he questioned whether what he was doing was right, and so did others in his orbit. In the end, though, he was convinced he was on the right path, so he stayed on it. Then, suddenly, all the hard work paid off and everything came together in one week. He got a series of wins in rapid-fire succession.

As a founder, I was in many situations like this. I ground it out for a few years before I had something material to show for it. I had conviction about what I was doing, but my friends and family thought I was nuts until the company got a big win. From this and other situations I’ve learned a few things:

• Winning doesn’t happen overnight. It’s usually the result of effort over time.
• Celebrate the wins. Building a company is hard and full of times when things aren’t going well. When they finally go your way, it’s important to stop and celebrate, especially when others contributed to your success. It’s a great opportunity to acknowledge the hard work everyone has put in and enjoy the moment.
• Reflect on what got you the win. Take time to learn from it. Think about what worked and led to the win. Identify those things so you can focus your efforts going forward. Said another way, lean into what’s working so you can have more wins.
• Don’t get complacent if you want to continue winning. It’s easy to relax a little and take your foot off the gas when you get a win. I’ve learned to do the exact opposite. Celebrate the win and then get back to doing what’s working. I’ve learned the hard way that complacency can quickly negate a win and lead to losses. Stay hungry and keep working toward your goal. You’ve won a battle, but you’re still fighting a war.

Everyone loves to win, but few think deeply about what it takes to get there or what to do after they’ve won. The above are a few things I’ve learned. I hope they’re helpful.

I talked today with some company representatives about their new-user pipeline. Their platform has self-serve onboarding with a free trial period (seven days). The team—tracking the pipeline pretty well—noticed customers getting stuck in the last step before converting to paid plans. Digging in a bit, I learned that customers could continue using the product for free after their trial period ended. With little incentive to decide to either buy or pass, many took the easy road and continued their free trials.

This company is very early in its journey. Its leaders want to get as many paying customers as possible. They also want to get feedback so they can make the product better. Allowing users to continue free trials longer than advertised accomplishes neither. The people who get value from the product aren’t paying, so you don’t who they are or how many of them there are—or even if they exist. The people who don’t get enough value from the product to pay for it don’t have to signal that. The founders can’t reach out to investigate the why behind “no” decisions so they can improve the product. Everyone is lumped together in the same bucket.

If you’re an early founder, consider having a hard end date for your free trial. The insights you gain could be invaluable.

I love listening to the origin story of a company. It’s always interesting to hear how founders came across a problem and figured out how they wanted to solve it. But sometimes I hear the opposite: a founder decided to build a solution and then tried to figure out how it could help customers.

I call this the solution-in-search-of-a-problem challenge. When founders build a solution without keeping the customer or problem in mind, they end up in a gray area. They build what they think people want instead of what people actually want. The solution ends up doing an OK job of solving a few problems but not a great job of solving any. Customers are reluctant to pay for it because it doesn’t create much value for them. The founders find themselves talking to different customers with different profiles in search of one that loves the product. They’ve often put so much time into building the solution that it’s hard for them to see that it’s not likely to succeed because it’s only an average solution.

If you’re an early founder, keep your focus on the problem and your customers so you can avoid building a solution in search of a problem.

I met with a founding team today to learn about their journey to date. They excitedly shared that they’d had a big realization that led to a breakthrough. The realization was insightful. I was curious to know how they came by this key piece of info, so I asked.

The founders had been building a product and getting feedback from customers for months. They thought they were building something that solved customers’ pain points, but the user sign-ups and engagement weren’t good.

The customers were still complaining about the problem, so the team was stumped. They had been asking customers how they could improve their app to make solving the problem easier, and they incorporated the responses in their product. One day, the CEO explained, he began asking different questions. He asked customers to share with him their current behaviors in running their business. He then asked what they were already doing to solve this problem (nothing). He learned they used many apps and were loath to try another one. He stopped asking how his company could make its app better and began asking how it could make life easier for them.

The team realized they were trying to get customers to change behavior and use another app. But their target customers are small businesses. The owners are stretched thin; they don’t have tons of free time. They’d rather lean into old habits than learn new ones.

The team noticed that the business owners communicated extensively via text messages, so they built a feature that allowed customers to communicate with the company’s app via text messages. Next thing they knew, engagement and sign-ups surged. Because the team asked the right questions and built a product that leverages existing behavior, it finally solved the problem in a way customers embrace.

The early parts of the founder journey are all about understanding the problem and your customer. Asking the right questions and paying attention to what your customers are already doing can be the key to building something they’ll love.

Chatting with an early founder about his plans to grow his company, I noticed he kept mentioning where the stock market could go if the recent downturn continues and the possibility of a recession in the short to medium term. This founder’s decisions are being affected by hypothetical future scenarios that are out of his control.

I quit my job and went full-time on my start-up just as the financial crisis was kicking into full gear. It was a scary time, but I didn’t let that stop me from pursuing the opportunity I saw in front of me. Because of the crisis, I was able to negotiate very favorable terms I otherwise wouldn’t have gotten and gain access to relationships I otherwise wouldn’t have had access to. During all the macro turmoil, I focused on growth. The business grew throughout the crisis, and I felt somewhat insulated from the macro dynamics because I focused on the opportunity I saw rather than the broader doom-and-gloom environment. When the crisis ended, we were in prime position to benefit from the ensuing economic uptick.

While not an ideal time for many, the crisis ended up helping my start-up and positioning us for greater success. If you’re an early-stage founder, be aware of the macro environment and how it could develop but focus more on the things you can control and on creating value by solving a problem. If you do, your company is likely to grow despite the macro headwinds.  

As an early founder, I often got backed up on email. After I finished working on the business all day, I couldn’t consistently respond to all my emails. That came back to bite me a few times when I missed some that were important. I either saw them too late or didn’t see them at all.

Effective communication is important, and email is one of the main forms of business communication. As I matured as a founder, I learned the importance of good communication, including managing my email effectively. And I learned a few tricks. These two worked the best:  

• Inbox zero – This is the best but most difficult approach. You clear your email inbox out every day. You deal with every email, even those that don’t require a response. I checked emails once a day in the middle of the afternoon to accomplish this.
• VIP senders – This was effective when I was pressed for time. Most email clients allow you to designate certain contacts as VIPs and segregate emails from them. I called it my VIP inbox. If my day was busy and I couldn’t get through my entire inbox, I made sure to deal with every message in my VIP inbox.

Managing email remains one of my least favorite tasks. I still struggle with it at times. But I realize that it’s difficult to be a good communicator if you don’t have a good email strategy.

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

• Iterative learning – This week was a reminder that getting to the ideal state of something is an iterative process that isn’t guaranteed to be smooth.
• January – Monday is the last business day of January—this month has flown by! This year is beginning very differently than 2021: we’re hitting the ground running. Last year, things ramped up slowly.
• Habits – Sticking with my new daily habits has been working well. It will take time, but I’m starting to see some of these habits produce positive results.

Week ninety-six was a busy week that required me to juggle competing priorities. I’m looking forward to next week being more normal.

I’ve shared my views on the digitization of distribution and its impact on banking. Today I read about Apple’s new service that will allow small businesses to accept payments on their iPhones. No hardware (i.e., payment terminal) will be required. Consumers will be able to tap a credit card or another iPhone against the business’s iPhone to send payment. The service hasn’t been launched as of today, but it’s coming, and it shows how Apple is inching closer to being a bank.

Helping consumers and small businesses with financial services is an enormous market—one of the few that could move the needle for a company the size of Apple. Banking is about to go through rapid change. Don’t be surprised if Apple ends up being the go-to bank for consumers and small businesses.

I spoke with a founder today who’s going after a consumer market after others have tried and failed. This founder is super excited and passionate and unconcerned about the competition. I eventually asked why he’s so confident he’ll succeed. He smiled and shared something he learned from his early customer interviews.

This founder has ferreted out a key insight. It’s something all the others missed and probably one of the causes of their failure. He’s using this insight as the foundation for his company. It informs what he’s building. He’s confident that if he stays true to it, he’ll be successful.

Key insights are an entrepreneurial competitive advantage. If you’re an early founder, consider asking yourself, What’s my key insight?