I spoke with a founder who shared some of his plans with me. He hesitated to reveal one detail, but I encouraged him to keep chatting. He planned to sell merchandise to customers in addition to his core technology product. I asked him why he wanted to do that and why he hadn’t wanted to tell me. He was worried, he said, that I’d think the merchandise was a distraction from the company’s core product and that he was scattered and unfocused. He sees the merchandise as important to building a brand and community.

Founders who are talking about their initiatives and ideas often get excited. They dive straight into the details of what they want to do. It’s very common; I used to do it myself. But the person listening usually doesn’t have the same context. They haven’t been thinking about this problem day and night. They don’t understand the customers and the market. Since they don’t understand the bigger picture, they’re left to wonder. Why are you doing this? The missing why prevents them from wrapping their minds around the details the founder is sharing.

Before founders explain what they want to do, they should tell their audience why they want to do it. Start with the high level and then get into the details. It’s a flow that’s much easier for a non-founder to digest because it provides context.

This founder has a great merchandise plan, and it makes sense. I think he should let other people know about it. When he does, he should begin with his big why: to create a moat with loyal customers by building a brand and community. With that high-level context, the merchandise plan doesn’t sound like a distraction. It sounds like a shrewd strategy.

When I decided to leave corporate America, some friends and family didn’t understand. I’d worked hard during college to position myself for a job with a reputable organization. I was walking away from that stability to pursue a risky start-up idea, which sounded crazy to them. It just wasn’t something people in my circle did. I was one of only a few with the tolerance for high risk needed to pursue this path.

As I look around today, I see a different landscape. Many people want to pursue entrepreneurship. It’s a beautiful thing, and I love it. But that doesn’t change the fact that being an entrepreneur is risky. It appears that more people have a higher risk tolerance and are moving forward as founders.

I’m now wondering if this higher risk tolerance is specific to entrepreneurship or more general. If the latter, what impact (good or bad) could this have on society over the next decade or so? I don’t have an answer to this yet, but I’ll be thinking more about it and getting the perspective of others.

One of the things founders hear often is “What is your big vision for this company?” Lots of early founders will respond with how much revenue they hope to reach or how many customers they plan to have. Those answers miss the point of the question.

Your vision transcends money and sales. It’s about impact. If you build a flourishing company, what impact will you, and it, have? Put another way, what does the world look like if you and your team are successful?

If you’re building a company or thinking of building one, consider taking time to think about the impact you can have . . . and the impact you want to have.

I caught up with a founder working on an early version of his product. It doesn’t currently exist in the market. And he’s not sure that the pain point is big enough to justify the product. He’s been focused on getting it in the hands of users and converting them to paying customers. But today he shared a new approach with me. He now realizes that feedback is more valuable than revenue at this point. Feedback will help him understand whether he’s going in the right direction and help him fine-tune the product. He’s decided to give the product away for free (for now) in hopes of acquiring more users so he can get more feedback.

I like this founder’s approach of prioritizing feedback over revenue. For his situation, it makes sense. I suspect the feedback he receives will lead to valuable insights.

Customer feedback is important. It helps you understand what your customers want, which is key to the success of any company. If you never listen to your customers, you’ll never be in tune with them.

If you’re building a company or thinking of doing so, consider incorporating customer feedback into your decision-making early. If you do, customers are likely to thank you with dollars!

I chatted with a founder today about my experience bootstrapping my company. We discussed the pros and cons of various ways of capitalizing a company and factors to consider. Here are the main takeaways:

• Talent – If you’re going after a big opportunity, you can’t do it by yourself. You need a team. You want to find the best and brightest people you can. These A players usually want to be compensated for their talents. They may accept equity and cash compensation, so you may be able to go a little lower on salary. But you don’t want them looking over their shoulder for the next opportunity. You need ample capital to pay people what they’re worth.
• Runway – When you’re executing a plan, it takes time to see a return on your efforts. You want to give yourself enough breathing room for your hard work to start paying off.
• Strategic thinking – When founders aren’t focused on day-to-day survival, it’s possible for them to think strategically about the business. And founders should be thinking long term about the business—which they can do only if they’re not trying to figure out how to pay this week’s payroll.

There isn’t a right or wrong way to capitalize and grow a company, but these are important considerations for founders. Bootstrapping and raising investor capital are common approaches, but there are others. Pick the one that’s right for you and that sets you up for success.

I caught up with a founder friend today. We talked about founder motivations, which can change over time. He made an interesting comment. If money is the main motivation, joining the team of a high-growth company should be considered—it can be more lucrative than starting something from zero. We recalled a few Atlanta start-ups where employees have made life-changing money turning the CEO’s vision into reality.

People have different motivations for wanting to become a founder. The most important thing is to be self-aware enough to understand what your main motivation is. Not being clear on this can make decision-making harder than it has to be.  

If money is the motivation—and there’s nothing wrong with that—be honest about it. Starting a company can definitely pay off financially, but be aware that it’s just one of many paths to potential riches. Choose your path wisely and try to align it with your main motivation.

I had a spirited chat with a friend this week about a house in Atlanta that just hit the market. We debated how long it will take to sell. I think it will sell within a week, and my friend thinks it will take a few months. Surprised, I dug into his why. He things it’s overpriced and that a price reduction will be needed to move it after it sits unsold for a few weeks. I think the price is fair. The true disconnect is what we think the house is worth.

After more back and forth, I got to the root of our disagreement. I’m bullish on Atlanta. I think the city offers qualities other major metros can’t that make it a place people see themselves settling down in and calling home for the long term. And pandemic dynamics contribute to it being a desirable destination. Home prices reflect this and are likely to continue increasing for the foreseeable future. I believe that prices are fair relative to where they’ll be in the future.

My friend has lived in Atlanta for a long time. He remembers a glut of houses on the market after the financial crisis and some now-trendy neighborhoods being seedy. He believes Atlanta is in a real estate bubble and prices will drop at some point. In other words, he believes current prices are inflated relative to historical prices.

As I reflected on our conversation, I realized that we had different perspectives: I was focused on the future, and he was focused on the past.

Looking at an opportunity, I’m a fan of future thinking. I wasn’t always like this. Flipping this mental switch transformed how I analyze opportunities. I’m able to see opportunity and capitalize on it because I can still see it as “cheap.” If things go as I predict, the asset will increase in value, and I will have gotten a deal at its current price. It’s irrelevant that I didn’t buy at the cheapest historical price, a consideration that I view as a mental trap.

I’ve noticed a pattern recently. I was working on something and couldn’t make a decision as quickly as I wanted to. Stopping to think about this, I realized a few things.

When I’m doing something familiar, gut instinct carries more weight in my decision-making. I know quickly what I want to do, even with little information. I may not be able to articulate my reasoning beyond listening to my gut, but I’m still confident in the decision. This is the zone I operated in as a founder for many years. I didn’t start off like this, but as the company grew, I gained confidence in my intuition and decisions.

When I’m doing something unfamiliar, it takes longer to decide what I want to do. I have a gut instinct, but it feels more subtle. To compensate, I try to gather more information that will help me make a decision I can be confident about.

My instincts are usually accurate in either situation, and I’ve historically been able to trust my gut and decide. But I haven’t been exercising this skill enough lately, and that’s affecting my decision-making in unfamiliar situations. I want to listen to my gut in all situations, so I’m going to experiment with exercises to help me get back to the old me: trusting my gut and making a decision, regardless of the situation.  

Personal finance has been a hobby of mine since high school. When I hear founders solving for problems in this area, I’m always interested. Today a founder shared some interesting insights that got me thinking. One of the biggest challenges I’ve seen is that most tools to help people manage their finances are outside the normal consumer flow. If you want to save for a big purchase or just stick to a budget, it can be difficult. Part of the challenge is that these tools are usually independent apps that the user utilizes after a transaction has occurred.

Digital wallets on smartphones are gaining traction. I believe that in the not-so-distant future, we will no longer carry a wallet in our purse or back pocket. Everything—driver’s license, credit cards, etc.—will be in our digital wallet. The digital wallet will be how we make purchases, and it will become the center of gravity for consumer purchases. When that happens, we’ll see the next evolution of personal finance tools, because they’ll be built into the consumer’s purchasing flow. They’ll be able to affect the buying decision before it’s completed. This could lead to sustained behavior change, which many of us desperately need if we’re to improve our financial situation.  

I’m not sure when the digital wallet will be adopted by the masses, but when it is, it could have a big impact on consumer spending habits.

A friend asked me to sit in on a chat with a founder. At the end of it, my friend asked if I thought the founder was right or wrong about the problem and his plan to solve it. I told him I had no idea.

I tend to be more interested in how someone arrived at a conclusion than the conclusion itself. Why they want to do things a certain way is more interesting to me than what they want to do. I shared this with my friend and told him that I think (at least based on this short conversation) that the founder has a solid thought process. He could be right or wrong initially. But his thought process will likely lead to eventually figuring things out and being successful.

Having a strong opinion is a great founder trait, but why you have that opinion is more important. As your share your vision and how you plan to execute it, consider sharing the why too.