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I share what I learn each day about entrepreneurship—from a biography or my own experience. Always a 2-min read or less.
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Entrepreneurship Is about Learning
Building a company is hard. There’s so much you don’t know that you have to try to figure out. I recently connected with a founder who’s building his second venture capital–backed startup. He raised over $100 million from investors for his first company and scaled quickly. During our conversation, it was clear that he’d learned a ton and planned to apply that knowledge to this new company.
A lot of people are interested in entrepreneurship but wait on the sidelines until they think they’re on to something that could be massive. Nothing’s wrong with this approach, and it works well for some people. I do think there’s another approach, though, that can increase your long-term chances of being a successful founder. Start working on building a company around a problem you’re passionate about. If the market ends up being smaller than you hoped for or customers won’t pay for your solution, that’s okay. Regardless of the outcome, you’ll gain valuable knowledge that will help you in your next entrepreneurial endeavor. That knowledge will help you avoid mistakes and save you tons of time the next go-around.
Being a founder is about learning as much as anything else. If you want to be a founder, put yourself in position to start learning as soon as you can. The more you learn and the earlier you learn, the more you increase your odds of succeeding . . . if not this time, next time.
Weekly Reflection: Week Sixty-Two
Today marks the end of my sixty-second week of working from home (mostly). Here are my takeaways from week sixty-two:
- Short week – Having Monday off was a nice break, and it made the workweek shorter. I like shorter workweeks, especially in the summer. I suspect a lot of people will be aiming for as many four-day weeks as possible this summer.
- Summer – June usually kicks off the summer travel and vacation season. I think this year will be especially active, and I’m curious about how business activity will be affected.
- Finish line – This week was a reminder to keep pushing, especially when I’m in the last leg of something. It’s important to persevere all the way to the finish line.
Week sixty-two was a short week. It was good and productive even though it feels like more people have a summer-vacation mindset.
Weekly Reflection: Week Sixty-One
Today marks the end of my sixty-first week of working from home (mostly). Here are my takeaways from week sixty-one:
- Opportunity – When an opportunity presents itself, someone who recognizes it and takes advantage of it can change the trajectory of their life. Sometimes it’s strategic. Sometimes it’s being in the right place at the right time.
- Holiday weekend – I’m looking forward to the three-day weekend. An extra day can make a world of difference.
- Travel – Lots of conversations about travel this week. People are excited about traveling again.
Week sixty-one felt like a short week even though it wasn’t. I think lots of people were in holiday mode well before the weekend. It felt like a productive but calm week, which was nice.
Weekly Reflection: Week Sixty
Today marks the end of my sixtieth week of working from home (mostly). Here are my takeaways from week sixty:
- Perspectives – I got some great feedback from people who have a different perspective than I do. I always learn a ton when I listen to others who see things differently. I don’t always agree, but I always get value from the exercise.
- Teamwork – Outlander’s pitch competition was this week. It took a lot of planning and hard work by the team to make the event happen. It was a testament to what can be accomplished when people work together.
- Idea session – I participated in a great session this week that was helpful to everyone involved. Lots of good things can happen when good people get together and focus on a single goal.
Week sixty was a busy week. Lots of long Zooms and other events, but a good week nonetheless.
Weekly Reflection: Week Fifty-Nine
Today marks the end of my fifty-ninth week of working from home (mostly). Here are my takeaways from week fifty-nine:
- Negotiations – Two parties advocating for their own interests: always interesting to watch it play out. Usually, the party with the most leverage gets more of what they want. But sometimes what you expected and what happens are different.
- Communication – This is the key to any healthy relationship. When people are proactive communicators, working with them is much easier. It won’t guarantee a good working relationship, but it’s necessary to one.
- Summer – I’m hearing lots of friends talk about their summer plans. This may be a very active summer with lots of people away from work. Makes sense, given the last year. I’m curious about business activity levels relative to past summers.
Week fifty-nine was a good week. No highs or lows. Just evenly paced and productive, which I liked.
Look for the Golden Nugget
When I’m facing a challenge, I’ve learned to ask credible people to tell me about their experiences and give me feedback. I’ve left some of these conversations, though, feeling like I didn’t get what I was looking for. I was talking with a founder yesterday and this topic came up. He shared a great insight with me. When asking for input, he aims to leave the conversation with a single golden nugget. No to-do list or pages of takeaways. He’s looking for one insightful thing that he hadn’t considered before.
This clicked with me. It made perfect sense. We chatted about how he landed on this approach. He made some great points. One was that most people are likely to act on only one thing from a conversation (for a variety of reasons). I agree. And if you’re going to act on only one thing, why look for ten?
I began replaying conversations in my head that I had deemed somewhat unproductive. I was able to identify a single golden nugget in most of them. Some of those nuggets had already proved helpful in navigating challenging situations, but I hadn’t given those conversations the credit they deserved because my expectations for them hadn’t been realistic.
I love this founder’s approach to getting feedback. Early founders have a never-ending to-do list and they often talk with lots of people. How beneficial would it be to learn one thing or get one idea from most if not all these conversations? When you leave a conversation, ask yourself: what’s the golden nugget?
Weekly Reflection: Week Fifty-Eight
Today marks the end of my fifty-eighth week of working from home (mostly). Here are my takeaways from week fifty-eight:
- Unfocused start – This week was productive, but I don’t feel like I got the month off to the start I’d planned. I’m behind on some things and need to refocus next week.
- Deadlines – Sometimes a hard deadline helps me get through a large amount of work in a short amount of time. It’s stressful, yes, but my brain clicks into another mode when it’s facing a hard deadline. I had an unexpected one this week and was able to meet it.
- Helping founders – I enjoy helping founders fill gaps and overcome obstacles. Sometimes, to reach their full potential, people just need a lucky break. I had a chance to give someone a lucky break this week, and it felt great! I’m looking forward to watching the founder’s journey.
Week fifty-eight was super busy. Next week I plan to be more focused and intentional to get back on track for the month.
Weekly Reflection: Week Fifty-Seven
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.
Weekly Reflection: Week Fifty-Six
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.
The Curious Entrepreneur
In the early days of my company, I had to figure everything out. I was often doing things in areas where I had zero experience. Some tasks were intimidating and complex. Other were simple but time consuming and tedious. All of it had to get done if I wanted my company to be a success, so I dug in. The tasks themselves weren’t always fun, but I enjoyed learning about new things. That’s true to this day.
I spoke with a former founder who’s now in corporate America. When he started his company, he too mastered learning new things. That skill has been invaluable over the years. It helped him take on new challenges in his own company and now in a large organization. Time and time again he’s been successful. When we spoke, he mentioned learning and executing new things as one factor that’s gotten him where he is today.
I believe curiosity is a trait that helps founders succeed. It helps a lot to have a genuine desire to learn about new things and get things done by applying that learning.
If you’re considering entrepreneurship, ask yourself, “Am I naturally curious?” If the answer is yes, it might be a perfect match.