I’m reading Working Backwards. It was written by two former Amazon executives, who detail why Amazon was able to become one of the most valuable companies in the world. The authors share the principles that guide Amazon, how it practices them, and the backstory on how Amazon arrived at them.

One section about why Amazon prefers small teams stuck with me. Jeff Bezos believes that decisions should be made with 70% of the information you’d like to have. Waiting to amass 90% or more means you’re moving too slow. The key to being successful while making decisions with only 70% of potentially available information is being good at course correcting. If you’re moving fast and catching your mistakes quickly, an incorrect decision is less costly than being too slow is. Amazon believes in small teams because they make it easier to catch mistakes and course correct.

I like Jeff’s thoughts. They reinforce that many decisions can be undone, so it’s better to move fast and undo them if you’re wrong than to wait to identify the perfect decision.

I listened to Sequoia partner Jess Lee share her thoughts (beginning at 12:20 in the recording) on how community can play an important role in entrepreneurial success. She defines community as customers who love the solution so much that they’re willing to talk to peers about it. She views community as the ultimate growth engine for the following reasons:

• $0 customer acquisition cost – When you build a place for people to share their thoughts about something they’re passionate about, they generate word-of-mouth advertising that costs you nothing.
• Feedback – These people are fiercely loyal and will give you candid feedback on what they like and don’t like about your solution. Their feedback is your ear to the ground, helping you find and retain product–market fit.
• Connections – People build relationships within these communities. Among members there’s loyalty and a sense of belonging.
• Underserved users – Even in large organizations, there are often groups of people whose pains aren’t understood and haven’t been solved. Connecting with these underserved users so they don’t feel alone can create loyalty. Solving their pain points further reinforces their loyalty.
• Key elements – The four important elements of a successful community are government, economy, religion (shared ethos), and media.
• Community needs first – The best communities are oriented to the needs of the community, not the needs of the business. Making connections and adding value for users helps build strong communities. The best community builders are customer (user) obsessed.

Jess does a great job of sharing her thoughts on community. I agree with them, and I believe the most successful companies will have a community at the core of their success.

I recently heard someone refer to the start-up world as a young man’s (or woman’s) game. When I dug deeper, he shared that he believes you have to pursue this path young (in your twenties) if you want to be successful.

I don’t agree, for a few reasons. Anyone can be successful as a founder, regardless of age, if they’re willing to put in the work. How you achieve success will likely change with your age and maturity. For example, when you’re younger you can put working hard above most anything else. All-nighters, weekends—they’re doable. You can be selfish with your time. As you mature and have other priorities, you begin to work smart while working hard. The work ethic is still there, but how you deploy it is likely more strategic and incorporates other priorities.

History is full of examples of people having entrepreneurial success in their forties, fifties, and even sixties. Ray Kroc (McDonald’s in his fifties) and Harland Sanders (KFC in his sixties) are two great ones.

If you can solve a problem in a way that creates value, you can be an entrepreneur—no matter how old you are.

A friend asked for my thoughts on accessibility of information, knowledge gaps, etc. Early in my journey, I didn’t know what I didn’t know, so I focused on acquiring knowledge about areas where I wanted to be successful (e.g., start-ups). That was helpful, but I realized it wasn’t enough. I had to take it a step further. I needed to figure out how to apply that knowledge. How do I apply it to my situation? How do I use it to achieve my goals? How do I execute given this new information?

Knowing what to do was helpful, but figuring out how to do it was a game changer because execution is what really matters. Knowledge is without a doubt valuable, but applying it is how you progress toward goals. I wasn’t always sure how to execute based on the knowledge I gathered, but I was determined to figure it out.

I ended up settling on two approaches. The first was to talk to experienced people who’d done what I was trying to do and ask how they did it. Dive into the specifics with them and get a better understanding of what worked, what didn’t work, and why. The second was to test. Come up with a few small things that have a reasonable chance of working and try them. Test them until I hit on the one(s) that work. Double down on what worked and kill the rest.

I still seek to learn and fill my knowledge gaps, but I also think about how to apply my knowledge and move the needle forward

I caught up with a founder recently and we talked about his frustrations. He shared that he’s been having a hard time the last few months. A laundry list of things aren’t going his way—from product, to customers, to managing his team. Some are the result of subpar decisions on his part. So many things aren’t going as he anticipated that it’s starting to wear on him mentally.

He asked my thoughts on his situation, and I shared my founder experience with him. On my journey, there was a pattern: when lots of things weren’t going right and my frustration level was peaking, I was usually on the cusp of a big breakthrough or material change in the business.

For example, we cut off one of our main suppliers because we weren’t aligned culturally. This caused us to start burning cash at a rapid rate. Tensions were high. We had some runway because of cash reserves, and I still believed in what we were trying to accomplish and in our team. Just when we were approaching max pain from cash burn, we identified a new supplier more advanced than our previous one. That situation set us up to go on a growth tear, and we scaled to eight figures in revenue.

When nothing is going right, be mindful that you’re likely on the cusp of a breakthrough if you push through!

I recently met with folks running an emerging fund who shared some interesting insights about their fundraise strategy. Their existing portfolio is performing well, and they’re out raising a new fund. They targeted $50 million, but because of recent market conditions they think they’ll land at $25 million. They’re adjusting the portfolio construction. They plan to do fewer investments and are raising the bar on what it takes for them to make an investment.

I wasn’t surprised to hear that funds are reducing the amount of capital they’re raising, given the macro environment, but the higher bar for investment was surprising given the success of their investments.

Risk aversion has ballooned, and founders should be aware of this and plan accordingly. We’ll eventually move back to embracing more risk, but I believe that will be a gradual process.

I chatted today with a friend who’s in a different industry. I enjoy talking to people outside of start-ups and tech for a different perspective. Our conversation naturally touched on the current macro state. He shared something interesting: in his industry there’s always demand for quality, regardless of what’s going on in the world. People putting out a quality product aren’t affected by the macro environment.

My buddy makes a great point that founders should be mindful of. If you’re solving a problem with a quality product that creates value for customers, customer demand will be there. And with authentic customer demand comes the potential to build a large company—you will be able to get capital from investors to scale.

Focus on quality and things will likely play out in your favor, even in a questionable macro environment.

Some solutions to problems that have the biggest impact on our lives seem obvious once we’re using them—though not before. Summoning a stranger to pick you up in their car or renting a room from a stranger both seem unremarkable now that we’re doing both. But a few years ago, they were nonobvious opportunities that many thought had no chance of succeeding. Uber, Airbnb, and a variety of other impactful solutions have changed how we live our lives and are each worth billions of dollars.

Evaluating a nonobvious opportunity for investment is hard. It requires investors to focus on what they stand to gain if things go right, not all the possible reasons for failure. And before investors can evaluate these opportunities, they have to find them.

I suspect that more nonobvious opportunities from great founders with the potential for outsize returns exist, but the network problem in VC prevents them from being funded. If this problem can be solved, I see more solutions being built that will have a material positive impact on society and create outsize returns for the limited partners that back these founders.

Had a great chat with an investor today. We discussed why some founders struggle when they transition out of big organizations. He shared an observation with me: Employees working at larger companies who don’t have founder friends but want to be a founder tend to focus on working hard at work. They miss the mark on building an outside network—so, when they start their company, they don’t know anyone who can help them.

As I listened to this investor, I thought about my early days as a founder. I quit a job in a big company, only to realize that I didn’t know anybody who was building a company. It felt like I was the lone man on an island. I eventually sought out other early startup founders, we formed a cohort, and my trajectory changed completely.

If you aspire to building a startup, start seeking out people who are building companies or who support people building companies. They will be instrumental in helping you navigate the entrepreneurial journey.

I watched an interview in which coach Mike Tomlin described how he stays at the top of his game. After winning two Super Bowls, he still has the same fire he had when he first became an NFL head coach fifteen years ago. Tomlin shared something that really stuck with me. He resists comfort. In fact, he tells his team, “Don’t seek comfort,” because special outcomes—outsize outcomes—are the result of being uncomfortable. He explained that he views thinking back to his success as a Super Bowl champion as seeking comfort. So, he ignores his past success and the comfort it breeds.

Tomlin may ignore his track record, but it’s impressive and speaks to his credibility as a coach and leader.

Growth often comes from being in uncomfortable situations. You’re forced to think about and do things that are unfamiliar. Succeed or fail, you’ll learn from those experiences. I really like how Tomlin is intentional about resisting comfort. It tells me that he’s a learner and constantly looking for ways to improve himself and the team he leads. It makes sense that after fifteen years, he’s still at the top of his game.

If you’re aiming to do something special, consider asking yourself, “Am I resisting comfort—or seeking it—when I make decisions?”