I’ve been giving advice to John on his start-up (it’s a reboot, actually). We worked on articulating his new vision clearly and making specific asks for help. I caught up with him today, and he told me things are going well. He’s pursuing a few strong opportunities that recently presented themselves. I asked how they came about. The answer was that he started asking for intros to specific people at the companies he’s targeting.

People say early founders should always have their elevator pitch ready to go, and I agree. Quickly helping others understand what your company does, and why, is important. Founders should also have something else ready: a specific ask. People want to support people and things they believe in, but they don’t always know how. By laying it out clearly, you fill that gap and make it easier for them to help. Instead of hearing “Oh, that’s nice; I hope it works out for you,” you may get the intro or land the customer that changes your trajectory. All you had to do was ask!

‍

I spent time talking with an acquaintance about his career. He’s not in technology or start-ups, so I was interested to learn about an industry I don’t have exposure to. During our conversation, it hit me that he’s accomplished a lot and has the accolades to back it up. He’s super successful, and this got me wondering: what did his path look like before he had success? I learned that he was exposed to his industry as a child. His father worked in it and made him aware of the possible paths he could pursue. He decided on one of them straight out of high school.

He’s had outsize success, for sure. He told me most people think it happened overnight. It annoys him that people don’t realize he spent over a decade learning and fine-tuning his approach before it started to pay off.

His story is similar to that of other successful people I know. None of them had overnight success. To the contrary: they spent years working and learning before things came together for them.

There’s no shortcut to success. You must be committed, and you must put in the work, even when others aren’t paying attention. If you aspire to be successful, settle in—it’s going to be a long ride!

I went to my local grocery store today and had a great chat with one of the employees. I’ve gone to this store for a long time and built a good rapport with this person. Today he told me it was his last day. I was sad to hear it but happy for him because he’s moving on to a better opportunity. The labor market has been on my mind as of late, so I was interested to hear the details of his situation. A few highlights:

• Multiple opportunities – He’s been evaluating three opportunities: offers from his current employer, one of its competitors, and a company in a different industry.
• Evaluation – He’s evaluating compensation, benefits, and the likelihood of the company setting him up for success in retirement. He has a great understanding of the benefits and retirement details of each employer. He wants to work somewhere he can stay for a while and retire from at some point.
• Frustration – He likes his current employer but is frustrated that new hires with less experience are being paid more than existing employees. He is training these employees, yet their compensation is higher than his. That doesn’t feel fair. He believes employers need to adjust compensation for existing employees to market rate or risk losing them to better opportunities elsewhere.
• Fit – He has a good idea of the type of work that’s best for him based on his experience and the stage of his career. He’s comfortable declining opportunities that don’t align. He’s looking for something that’s a good fit for him and the employer.
• Excitement – He’s genuinely excited and feels like he’s in the driver’s seat of his career (maybe for the first time). He has the chance to work for a company that values his contributions and will set him up for success during and after his time with them.

It’s impossible for a company to be successful without a good team. As a founder, I saw firsthand how others contributed to the success of my company. The current labor dynamic is changing how companies go about building good teams. While anecdotal, today’s interaction gives me the feeling that we’re on the cusp of a change in how some companies approach recruiting.

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.