40 Lessons From 40 Years

I turn forty today. I can’t even believe I just typed that sentence. Over the past month, I've been reflecting on the lessons I’ve learned directly through experience or indirectly from family, friends, mentors and teachers.

I wanted capture and share these learnings for one important reason: I’m now a father to a beautiful baby girl and I’m not going to be here forever. Preserving myself digitally is becoming more important as I enter middle age.

Here are forty nuggets of wisdom that I’ve picked up throughout my first forty trips around the sun. May the next forty (god willing) be as wonderful and enlightening as the first forty.

  1. It’s ok to say, “I don’t know” because it’s impossible to have all the answers. The older I get the more I realize knowledge is practically infinite and I don’t know that much.

  2. Don’t underestimate the power of being the first to truly believe in someone.

  3. Everything rises and passes. It’s a law of nature. Change is constant around us and within us.

  4. Don’t always trust your feelings and snap judgements about others. We’re very good at crafting stories and beliefs in our minds with very little information and context.

  5. Every person is likely struggling with something. Be kind. Be helpful.

  6. Don’t buy something just to buy it. Accumulation of things will never lead to sustained happiness.

  7. When we speak openly about our challenges it can give others the strength and courage to do the same.

  8. Time is the single most important non-renewable resource we all have. Fill your days with what truly brings you alive, fills you with energy and allows you to grow.

  9. The only person you can change is yourself. It is nearly impossible to change other people. However, when they notice your own change, it might give them the courage or impetus to change themselves.

  10. Being a parent is 5x harder but 100x more enjoyable and fulfilling than I ever imagined. Love for a child is boundless. Caring for your child is the purpose of life.

  11. If you want to make progress on the things that matter most, you need to decide who you’re going to disappoint. It’s inevitable.

  12. Real trust and deep relationships can’t be manufactured or rushed. These are built over time through countless authentic and meaningful interactions and experiences.

  13. Traveling is single most effective way to learn about yourself, humanity and the world.

  14. Most of the time, family and friends don’t need you to fix their problems, they just need you to be there with them.

  15. We are all far more powerful, resilient and adaptive than we even realize. It’s never too late to change and remake yourself. We are all a work in progress.

  16. Equanimity isn’t suppression of thoughts or feelings but rather being ok with how a situation unfolds or how we feel in a given moment.

  17. Meditation is surest path to understanding yourself, your feelings, your thoughts and your perceptions.

  18. If you wait for the perfect moment or inspiration to learn a new craft or create something, you’ll never progress. Start now if it’s truly burning within you or else you’ll be exactly in the same place ten years from now.

  19. Listening with your eyes is just as powerful as listening with your ears.

  20. Living a sober life is vastly more enjoyable and liberating than society wants you to believe. You can have fun and be social without substances.

  21. Every single one of us has a different map of the world. So if you want to understand someone then you have to understand their map.

  22. Don’t force things. Apply the just right amount of effort but not too much.

  23. Being uncomfortable will take you to your edge and that’s where real growth and transformation happens.

  24. How you spend your time and your calendar reflects what you truly value in life.

  25. Pick your spots. We have limited time and our brains can only process so much. Focus is key. Choose wisely.

  26. A great teammate always puts the organization and its purpose ahead of their own self interests.

  27. Admit when you’re wrong and/or being an asshole. And when you are, learn from those experiences.

  28. You can’t be everything to everyone so might as well be yourself. Follow your values.

  29. All relationships, even the healthiest ones, are difficult and complex because most humans aren’t ‘compatible.’ The key to making them work is open communication, patience and compromise.

  30. You can likely learn the fundamentals any topic or craft if you dedicate ~100 hours. That’s not much time in the grand scheme of things. Immersion leads to progress.

  31. It’s not about the light at the end of the tunnel. It’s the tunnel. Show up every day and enjoy the process.

  32. Journaling for at least fifteen to thirty minutes is one of the most powerful forms of self care and therapy.

  33. You’ll never get what you don’t ask for or actively seek out. Go for it!

  34. Don’t expect to achieve very much if you spend your life trying to please others.

  35. Good physical and mental health is the single most valuable thing in the world. It starts with a good diet, regular exercise and ample sleep (7-8 hours).

  36. Long walks in nature are amazing for processing thoughts, emotions and important decisions.

  37. The best investment you can make is your own education. Never stop learning. The second best investment you can make is building your network through authentic and meaningful interactions. It is what you know and who you know.

  38. Sometimes you need to slow down to speed up or go backwards to move forward.

  39. Forgiving and making amends are brave and powerful acts that can help you turn the page and begin to move forward.

  40. Life isn’t perfect for everyone but we all have the freedom to choose how we respond to our circumstances. Don’t underestimate the power of faith, hope and positivity.

How Shake Shack Taught Me To Be A Better VC

One of the internal areas I focus on at Primary is what we call the ‘founder journey.’ This is the end-to-end experience that a founder has with Primary. It includes everything from the initial intro email all the way through post investment support. As a startup, we strive to be thoughtful about every touchpoint and interaction. We’re far from perfect and refined but working hard to improve every single day.

At the firm’s annual offsite this summer, I presented an update on our ‘founder journey’ progress and the strategy for the next twelve months. I kicked off the presentation with a quote from Danny Meyer.

“Business, like life, is all about how you make people feel. It’s that simple, and it’s that hard.”

For those who know me well, know that I’m a huge fan of Danny and his company Union Square Hospitality. Danny has created some of the best restaurants in New York including Union Square Cafe, Gramercy Tavern, Eleven Madison Park and Shake Shack.

For many reasons, I believe venture firms are in the hospitality business. This is something that I try to preach internally. In a hyper competitive, cash flush environment, entrepreneurs are likely to go with the firm that gives them the best shot to succeed and the partners they would like to work with over many years. At the end of the day, we’re in a people driven services business.

On the way back from our offsite with hospitality on my mind, I pulled out my Kindle and re-downloaded ‘Setting the Table’, Danny’s memoir and philosophy on business. This is one of the best books on leadership and hospitality that has ever been written. I’m not kidding. It’s so good that I’ve read it multiple times over the years.

Danny’s central philosophy is ‘enlightened hospitality,’ which is how the delivery of a product or service makes its recipient feel. He makes a compelling argument that hospitality is the key differentiating factor for success in a service-driven economy.

Because we now live in an information rich world, the knowledge and barriers required to launch a product and service have collapsed. This is why we’re seeing multiple competitors emerge in just about every category from CPG to SaaS. It feels like every product or service is being commoditized including the venture capital business. In this kind of environment, the difference maker is the internal culture of the organization and end-to-end customer experience.

So how does an organization move from just shipping a product or service to fully embracing enlightened hospitality? It begins by defining, understanding and prioritizing your core stakeholders.

Who do you exist to serve? Who directly benefits from your organization? Which relationships do you prioritize? Why? What implications do these choices have on your strategy and decision making? How do you satisfy and balance the interests of each group? What can you do differently to serve each of them more effectively?

Stakeholders should be different for just about every organization. An obvious example: our stakeholders at Primary are certainly different than those of The City of New York. And for good reason. This is driven by leadership, strategy, sector, values, purpose, culture, philosophy and so on.

In the case of Union Square Hospitality, the organization has five primary stakeholders “to whom we express our most caring hospitality, and in whom we take the greatest interest.” How the organization prioritizes these stakeholders is the guiding principle for every decision they make. According to Danny, this approach has “made the single greatest contribution to ongoing success of our company”

Their stakeholders in order of importance are:

  1. Employees

  2. Guests (a.k.a. diners)

  3. Community

  4. Suppliers

  5. Investors

Danny fundamentally believes that unless he prioritizes and takes care of his top four stakeholders then he won’t be able to take care of his investors and provide them with a strong and long-term return on their capital:

“To prioritize differently breaks the virtuous cycle of enlightened hospitality and seriously compromises the chances that your business will achieve excellence, success, good will and soul. Prioritizing our way has enabled us to offer investors an opportunity to affiliate with a business known for outstanding employees, warm hospitality, strong ties with exceptional supplies and a solid commitment to playing an active, valuable role in its community.”

When you deliver value to each of your stakeholders, it creates a flywheel effect (or virtuous cycle) and positions your organization for long term success and sustainability. Getting this flywheel humming is much easier said than done. For starters, every stakeholder group is different and has unique interests. Additionally, the world is always changing so you have to adapt your approach over time. Finally, these decisions and tradeoffs permeate throughout every function of an organization.

If you’re a founder or leader within an organization, I challenge you to think about your key stakeholders and how you’re delivering both short-and-long-term value to them. Who are you serving? What is the value exchange? Where can you improve? What needs to change?

I’m asking these questions internally at Primary and to some of our portfolio companies. It’s a fun and important thought exercise.

In closing, delivering true value to all of your stakeholders requires a huge amount of buy in, effort, intention, time and money. It’s certainly complicated but it can be achieved as Union Square Hospitality and other great organizations have proven. Doing this well might very well be the difference between building an enduring market leader rather than just an average company.

Adyashanti On Letting Go Of Fear

Last month, my friend Hursh introduced me to Adyashanti, the philosopher and spiritual teacher. I’ve been on break this week so decided to go down a rabbit hole and watch a number of his talks on YouTube.

This one on fear particularly resonated with me. Instead of fighting our fears, Adyashanti suggests slowing down, getting still, and relaxing into the knowledge that you will let go when the time is right and you are ready. He makes a compelling argument that there’s nothing to fear to begin with but we need to discover that ourselves by meeting that fear.

If you’re currently battling fear in your life, I invite and encourage you to take fifteen minutes to watch this short talk. It helped me shift my perspective and let go of a fear I’ve been holding onto for months. May it do the same for you.