In my twenties, I made an investment that I learned a ton from. It was the very beginning of the financial crisis. I saw an opportunity, made up my mind, and pulled the trigger. A few months later, the world was in free fall. The value of my investment plummeted, and my startup was struggling to get customers. It felt like nothing was going right for me (or anyone else). I recently reflected on that time with a close friend:

• Experience – I didn’t have experience with the type of investment I was making. In hindsight, I wish I’d connected with someone more seasoned in the space so I could have factored their wisdom into my decision-making. My lack of experience handicapped my decision-making and execution.
• Timing – The impact of timing can’t be underestimated. It’s not something one can usually control, but it can have an outsize impact on returns. In this situation, I was too early.
• Conviction – I didn’t have strong conviction about the investment I was making, so when things began to go differently than I had anticipated, I was ready to sell. I sold way too early for a small profit. Had I held on, my profit would have been huge. If I don’t have a strong conviction about something, I shouldn’t invest in it. Conviction is key to weathering the ups and downs of the journey.
• Horizon – I didn’t have much of an idea how long I planned to hold the investment. That and lack of conviction resulted in a premature sale. I now try to think about how long something might take to reach its full potential and use that as my time horizon.

In the end, this investment turned out fine and I learned a ton from it. I’m glad I did it. Because of it, I gained valuable knowledge that’s been useful over the years.

I was chatting with a founder friend about early-stage entrepreneurs. This person was a founder for over a decade and then sold his company. He’s lived it and achieved what many founders aspire to, a liquidity event. During our chat, he mentioned that early founders need to be committed to the problem they’re solving, not just fixated on being a founder or being part of a startup.

He’s right. He and I both spent over a decade building our respective companies. There were many tough periods and trying moments. Those are the times that test founders, and their commitment to the problem determines whether they pass the test. If a founder cares mostly about the title or the “glamour” of startup life, they probably won’t be motivated to stick it out during tough times.

Starting a company is hard, and building it is often a journey of a decade or more. If you’re considering being a founder, make sure that what you’re working on excites you enough to make you want to push through thick and thin.

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

• April – Time is flying. I can’t believe the month is over already. Or that a third of the year is behind us!
• Thinking time – Lately, I’ve been spending a lot of my time doing and not as much as I would like thinking. So I blocked out time to think this week. It was good to have some bandwidth to reflect. Hopefully I can do more of it going forward.
• Learning new things – I spent a decent amount of time learning something new this week. It’s always fun and exciting to learn new stuff that I’m interested in. I love the challenge, and it feeds my curiosity.

Week fifty-seven was a paced week. Four months down, eight to go. Looking forward to the rest of the year.

I spoke with a sharp founder who has a problem I rarely hear about: he’s turning away customers because he can’t service any additional business. He wants capital to expand his team so he doesn’t have to do that anymore! Having been in his space for a decade, he understands his customers’ needs well.

His waiting list and revenue growth are indicators of a likely product–market fit. His platform is creating value for customers by solving a painful problem. And they’re readily paying for it. All great signs. This founder is entering a phase where scaling the company will be his next challenge.

It’s not often that founders find themselves in the position of having to tell customers no. Congrats to this founder! I’ll be interested to see how he handles the scaling phase of his entrepreneurial journey.

When founders think about capital, venture capital or angel investors often come to mind. I’ve always thought, though, that customers are the best and cheapest source of capital (that’s why I bootstrapped my company). Most people think of selling a product or service as the only way to obtain money from customers. It’s not. (It’s just the most common way.)

If a company’s solution solves an extremely painful problem, customers may be willing to provide capital in other ways. If the solution creates an enormous amount of value, customers will pay for it and may also be open to becoming investors. When you think about it, it makes a ton of sense. Who better to understand the potential upside of a company than someone using its solution? Obviously, this is less likely if your customers are small businesses, but you never know. A company I’m familiar with has an amazing solution that has the potential to eliminate tons of labor expenses. A large customer that spends a lot of money on labor invested and helped refine the solution. The investment was a win–win.

Customers can be a great source of capital. This is just one example. Early founders, don’t forget about them when you’re thinking about raising capital.

A group of founders reached out to catch up recently. I’ve known one of the founders for some time now; he contacted me after I did a presentation and we’ve stayed in touch since, syncing every three or four months.

Our last chat was a bit different. He and his founders have been working on a product as a hobby. They built a solution to a problem they saw and have been slowly getting new customers as their time permitted. Recently, potential partners have asked them for help solving a particularly painful problem. Luckily, their product already relieves this pain. They’re realizing this could be huge and an opportunity to build a big business. They just aren’t sure how they should be thinking about funding to capitalize on the opportunity.

We scheduled a quick chat in which they asked pointed questions and I gave candid answers. Because of the preexisting relationship, the conversation was productive and straightforward. I already knew what problem they were trying to solve and how their solution worked. They brought me up to date on the larger opportunity they’ve uncovered.

Preexisting relationships with early-stage investors can be valuable for founders. These founders initially reached out cold, and we built a relationship over time. I was receptive to them because they were self-starting and demonstrated execution (they’d built a product and had a handful of users). When they had questions about a new opportunity, they had a friendly to turn to for help.

If you’re an early founder, consider building relationships with investors before you need them. All investors might not be receptive or responsive, but someone will probably get back to you. An investor friendly can be helpful when you need advice or honest feedback in the clutch.

Over the past few months, I’ve been hearing more early-stage founders say they have coaches. Some sought coaching on their own. Others did so because it was suggested.

I’m a fan of coaching and have experience with it myself. Quite a few of my founder friends have also been coached. It’s a great way to foster self-awareness and work toward becoming the kind of founder you aspire to be. It’s not always fun or easy. A good coach will tell you things you don’t want to hear and have you do exercises you’d rather not do. But the effort is usually worth it in the end.

It’s great to hear more early founders openly discussing coaching. I think this a big plus for them, and I hope the trend continues!

Working long hours is part of the job description for founders. The to-do list is constantly growing but the end of the runway gets closer every day. Founders often work long hours because they want to—they’re passionate about what they’re doing—and because they must—it’s what’s required to turn their vision into reality. Most founders understand this going in, but they don’t always understand the corollary: when you’re working that hard, you need an outlet.

When I was a founder, I looked forward to exercising. I started because I wanted to stay active, but I got so much more out of it. The workouts gave me a great mental reset and a way to relieve the stress of the day. I never thought about anything related to work, which helped my mindset. I worked out with a close-knit  group of people who had no idea what I did for a living. We just saw each other for the people we were. Looking back, exercising with that group of people gave me the outlet I needed to survive the long work hours.

Exercising was my thing, but it won’t work for every founder. If you’re a founder or want to be one, figure out what your outlet will be and make it a priority from day one.

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I connected with a buddy who built an analytics platform for enterprise clients. (Think billions of dollars in annual revenue.) He mentioned that he’s about to roll out an update to the platform that has nothing to do with analytics. It’s to provide an administrative capability his enterprise clients are accustomed to seeing in other platforms they use. He wasn’t thrilled about using engineering resources for this versus enhancing analytics capabilities, but his enterprise clients have high standards.

When I was running my company, we were always on the lookout for tools that allowed us to do our jobs better. They weren’t always perfect and didn’t have all the bells and whistles, but they saved us time and helped us execute better. We focused on what the tools added to our productivity, not what they were missing. This approach meant that we became early customers of innovative companies building great tools. Over time, we saw some of them evolve into huge successes. As they grew, some of them went upmarket to enterprise customers. We benefited from being along for the ride. Our company was on the cutting edge of some things simply because we were loyal, patient early customers.

Founders who want to target enterprise customers straight out of the gate should be mindful that their product may have to be fully baked for these organizations to even consider trying it. They can be risk averse and less forgiving if the product still needs tweaking or has issues. Companies that plan to go after these large customers often need to spend more time developing the product before they begin selling it, which means they usually need more capital to survive longer without customer revenue. Enterprise customers can be great when you land them, but landing them can require a lot of upfront product development and capital.

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

• Jam session – I had a great conversation with a founder friend. We’re both passionate about helping very early-stage companies, and we came up with some really good ideas that I’m excited about working on. I enjoy jam sessions like this one where I can talk through problems and ideas with someone who’s interested in similar things.  
• Monthly goals – I set a few monthly goals in March and shared them with some other people. I didn’t write them down and actually lost track of what the specific goals were. An acquaintance asked me about them today (luckily, he had written them down). Surprisingly, I’ve achieved each of them or come very close. Achieving goals that I hadn’t recorded or revisited for a month was a sign: they originated from an authentic place. Authentic passion kept me moving in the right direction all month. Looking forward to setting more authentic goals (maybe I’ll write down the next set!).      
• Admin – I didn’t have as much admin time as I needed this week. It feels like some things have gotten away from me. I plan to address this next week.  

Week fifty-six was a busy and exciting week. Lots of things in the works and lots of activity overall. Hopefully next week will have a more normal pace.