What I learned from interviewing 230+ people

In the last 2 years, I have published interviews with over 230 incredible founders, investors, and operators. Here are the most common themes in the advice, learnings, and key takeaways they shared.

Learning is currency. “Optimize for learning” is an often thrown around phrase, but what does that truly mean? How do you put that into practice? What I learned is that successful people are curiosity driven. Instead of following the money or following their peers, they follow their own interests. They have a lifelong love for learning. When they enter new companies, teams, and industries, instead of feeling discouraged, they feel excited about the prospect of learning. Instead of waiting for other people to educate them, they go find resources, both content and people, to learn from. Regardless of pay or title, when they learn something new each day, they feel satisfied. Learning is the currency through which they measure success and the north star to which they are driven.

Asking questions leads to deeper understanding. Successful people are not afraid to ask questions, even the most seemingly basic or obvious ones, especially as they are learning about new spaces. They do not worry about how others will perceive their lack of knowledge. They know asking questions is the best way to navigate steep learning curves.

Everything comes down to people. Companies, organizations, and departments are not abstract entities or objects. Successful people realize that all of these groups are just collections of people. When you realize that the outcomes of companies come down to how the people within work together, you invest everything into finding the best people, developing a great culture, and cultivating strong talent.

Communication is not about what you say but about what people hear. When you communicate with diverse audiences, it is crucial to meet people where they are. Successful people put themselves in the shoes of their audience, understanding what makes them tick, what they know and do not know, what they care about, and what they are worried about. When they share information with them, they use analogies to make more complex concepts easily understandable and relatable. They get people excited through speaking about what is most important to their audience. They also know that what matters more than the words they use is the feelings they elicit. They focus on the emotional resonance behind their communication, ensuring they leave everyone with positive energy.

Overplanning is overrated. Don’t overplan your life. Some exciting areas where you find new opportunities 5 or 10 years from now may not even exist today. Moreover, it is in these newer industries and domains where you can build more comparative advantage for yourself. In these newer areas, everyone starts on equal footing with no time based advantage. Use this to your own advantage by keeping an open mind, learning about new exciting areas quickly, and doing all you can to create something of value for the ecosystem.

Trust is built in pieces. Details matter. Every little thing you do and every little thing you put out there goes into your brand and your company’s brand. Every interaction and everyday is an opportunity to build trust. Successful people know that trust building work is never complete, and they put their all into everything they do, no matter how seemingly insignificant.

Kindness is crucial. People can sense your attitude through your expression, your tone of voice, and your follow through. Be kind to everyone you meet, regardless of who they are. People want to feel heard, and people want to feel like they matter. Successful people know that every interaction is an opportunity to make people feel appreciated. When someone asks a question or asks for advice, instead of sounding dismissive or condescending, be excited and engaged in supporting them. People will never forget those who gave first to them and especially those who helped them when they were just starting out. Being kind costs nothing and means everything.

First impressions set the foundation for everything. Pretexts matter. Your actions and your words are always interpreted in the context of the impression you set and the brand you build. Invest in building trust with people from the very start.

The context of your work matters more than the work itself. Successful people understand that no task is ever done in isolation. There are always upstream inputs and downstream impacts. Instead of just doing their assigned work heads down, successful people aim to understand the why behind what they do and where and how their work fits into the broader company and ecosystem. In this way, they are able to propose ideas for ways to do things more efficiently and are able to better service the mission.

Health and family are what ultimately matter most. Successful people know what to prioritize at the end of the day: their physical and mental well being and their loved ones. They are great at what they do but don’t let themselves get carried away by their work. They know that we are all nothing without our health and without our parents, partners, and children. They set goals to shut off their phone, show up for their children’s sports games, and spend time reading to them at night and chatting with their partners every morning.



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