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.

There Is No Perfection

Yesterday, I went for a stroll in Madison Square Park with my friend Dan Kimmerling who was visiting from the west coast. Dan one of the most thoughtful, intelligent and empathetic seed investors I know. Every time I get together with him, I walk away with nuggets of wisdom, insight and/or inspiration about a range of topics including the venture business, startup life and philosophy.

We were discussing that nagging and unsettling feeling that many of us often experience when things don’t seem to be perfect in life. It’s that feeling that ultimately forces us to start considering big life decisions such as making a career change, starting a new venture, leaving a relationship, moving to a new city and so on.

Dan said something that stuck with me and has been on replay in my head over the last twenty four hours:

“There is no perfection. Don’t allow the desire for the future perfect to be the enemy of the present sufficient. Because the future perfect is an illusion, once achieved, will suggest yet another future perfect.”

I’ve fallen into this mental trap more times than I’d probably like to publicly admit. It’s so tempting and easy to find dissatisfaction in our lives especially living in New York where the markers of success are always in our face and constantly moving higher and higher.

That voice in our head is incessantly chirping away: If only I had a better job. If only I made more money. If only my company made these strategic changes. If only I were able to buy that fancy shirt. If only I could date that perfect person. If only my boss didn’t Slack me at 7am. If only I had my own fund. If only I could go to yoga in the middle of the day. If only. If only. If only.

As Dan pointed out, the future perfect is an illusion so once we arrive at that destination yet another one will emerge. We eventually find ourselves in a never ending quest to chase perfection. We never feel at home.

I’m not suggesting that we get complacent and put our hopes and dreams aside. I hope every single human on the planet is able to create a life that is filled with joy, happiness and fulfillment. I genuinely do. I’m purely suggesting that we become aware of when our future perfect is clouding our perspective and simply acknowledge that some goodness does exist in the present sufficient.

How To Conduct A Comprehensive Annual Review

“Without reflection, we go blindly on our way, creating more unintended consequences, and failing to achieve anything useful.” -Meg Wheatley

The holiday season is my favorite time of the year. It symbolizes family, friends, vacation and of course plenty of good food. I also enjoy it because it marks the end of the year and the beginning of a new one. This is an ideal moment to reflect on the past twelve months and to define what we want to achieve in the year ahead.

So much happens over the course of a year. Lessons learned. Victories. Hardships. Physical changes. Special moments. Personal growth. New relationships. But by the time New Year’s rolls around, we often forget most of what happened because life gets in the way.

Many of our employers have us complete an annual review and set goals before year end. This makes good sense. It’s difficult to know where to head if we don’t know where we’ve been. But this leads me to the question: why don’t we conduct an annual review for all the components of our life? The answer is simple: we don’t create the time necessary, feel any pressure to or have a blueprint to guide us.

For the last three years, I’ve carved out time at the end of the year to conduct a comprehensive annual life review. The process has been not only cathartic but also illuminating and empowering. In fact, this exercise has helped me identify what’s important, shed what isn’t, and transform in many ways. As a result, I decided to get sober, leave a job that wasn’t the right fit and pursue coaching as a profession.

Several clients and friends recently asked me to share my annual life review blueprint. What follows is an attempt to provide the framework and hopefully the nudge to complete your own annual life review.

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Startup Pitch Decks

A few weeks ago, Alex Iskold of TechStars NYC asked me to talk with the Winter 2017 class about constructing an effective fundraising pitch deck. I jumped at the chance because this is an important topic that often comes up with first time and even repeat entrepreneurs when they’re about to embark on a fundraising process. In my short career as a VC, I’ve reviewed thousands of pitch decks and helped hundreds of founders refine their pitches. Additionally, I’m often approached by founder friends to provide feedback on their slides before they go to market. Given pitch decks are frequently discussed and they’re essential in the fundraising process, I thought it would be useful to create a simple guide to building an effective pitch deck.

Our goal with ‘Startup Pitch Decks’ is simple: to provide founders with a simple framework and reference guide that can be utilized before kicking off a fundraising process or when you’re in the throes of drafting your pitch deck. We dive into a number of topics including the ideal format, a sample build process, tips and tricks, advice from RRE founders, and even things to avoid. We’ve tried to make the guide as comprehensive as possible but realize it’s impossible to include every piece of advice and address every question. As such, we’d love to hear your questions, suggestions and feedback. Our aim is to evolve ‘Startup Pitch Decks’ with your help and input so it gets more useful over time.

All that said, it’s my pleasure to present Startup Pitch Decks. Hope you find it useful, thought provoking and perhaps even inspiring.

(Finally, I’d like to thank my colleagues at RRE — Jason Black, Alice Lloyd George and Cooper Zelnick — for providing feedback and adding some polish to the final product)

Here’s How My Wife Helped Me Become A Better VC

I am a VC. My wife is a founder. When I walk into our apartment at the end of each day, my role morphs from investor to husband but I also become a motivational coach, sounding board and sometimes even a punching bag. There’s virtually no barrier separating my life from entrepreneurship. It’s a constant. I have a completely unfiltered view into the life of an entrepreneur. I see the wins, the losses and everything in between. This situation has helped me gain a deeper appreciation for entrepreneurs and the daily battles they endure and sacrifices they make.

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The Advice a Cabbie Gave Me The Day I Moved to NYC

On this day nine years ago, I stuffed two huge duffel bags with all my clothes, left my apartment in Seattle for the final time and boarded a red eye in route to NYC. At the time, many emotions and questions were racing through my mind. Do I have what it takes to succeed in the big city? Will I be able to survive in the concrete jungle away from the mountains and lakes of the Pacific Northwest? How the hell am I going to navigate the subway? Will I make enough money to live comfortably? I was nervous about so many unknowns but amped about the endless potential and opportunities of NYC.

When I finally landed at JFK and deplaned, I was still half asleep and took a minute to get my bearings. I then stumbled to the baggage carousel, located my overstuffed bags and hoisted them on to a SmarteCarte so I could make my way to the taxi stand. Since I landed early on a Sunday morning and the airport was virtually empty, I was able to stroll right to the front of the line. As soon as I got to the curb, I was greeted by a middle aged cabbie from the Bronx with a thick New York accent. He got out of the taxi, helped me load my bags into his trunk and slammed the door behind me as I got into the back seat.

We made eye contact through the rearview mirror and he asked, “Where would you like to go, chief?” I fumbled with my tattered itinerary, glanced back at him and relayed, “I’m heading to 48th Street between 7th and 8th Avenue. Do you know how to get there?” The cabbie laughed for a second and glanced back at me. “With all that stuff, you must moving to the city, huh? What brings you here?” I explained that I had just moved to the big city for a new job and was starting a new life. Our eyes met in the rearview mirror once again. He then he became serious and delivered words I’ll never forget:

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Over the weekend I was fortunate to participate in my first “Medi Club,” a monthly gathering of urban-dwelling meditators. Medi Club is the brainchild of Jesse Israel who wanted to create a safe place for modern meditators that achieved three core goals 1) meditate with like-minded meditators; 2) discuss how meditation relates to issues like relationships, creativity, sex and work/life balance; and 3) deepen practice with new knowledge and interaction with the community. Here’s a little more context on what Medi Club is all about: ‘A Place for Modern Meditators.’ Last night’s theme was centered around transitions in life and work. This particular topic has been top of mind for Jesse because he’s in the process of finding a new path.

For many people, going through a career transition can be both exciting and scary. There’s so much unknown. What are people going to think of me? Can I survive without an income? What do I want to do with my life? Who should I talk with? What would make me happy? Who do I aspire to work with? How long will this take? So much is on the line. For many New Yorkers, a big part of our identity is tied to what we do for a living because it provides meaning and context in a dense city with eight million people. When our immediate existence is challenged, it’s only natural to feel anxiety and uncomfortable because there’s so much uncertainty. In my own career, I’ve found change is never easy but it’s a natural step in the process and it’s required to evolve into a better human.  

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Improving Human Interaction

While on vacation I decided to finally read the timeless classic by Dale Carnegie, ‘How to Win Friends and Influence People.’ The book was first published in 1936 and has sold more than fifteen million copies worldwide. It’s the granddaddy of all people skill books. Many of the lessons contained within are still relevant for anyone that deals with people.  Given Venture Capital is a highly social business with thousands of human touch points each year, this book was probably one of the most important I have ever read. 

We have a saying at RRE that our brand is the sum total of the positive and negative interactions that someone has with our team. Every touchpoint matters regardless of the medium (face to face, email, social media, etc.) and those involved (founders, limited partners, other VCs, etc.). At the most fundamental level, we operate in relationship-driven industry so we’re only as good as the interactions that people have with us (and of course the success of our investments). 

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What Jeff Bezos Thinks Is Cool

I just finished reading the book, The Everything Store, which chronicles the life of Jeff Bezos and the rise of Amazon.  Towards the end of the book, the author, Brad Stone, tells a story about Bezos’s quest to understand how Amazon could be admired and not hated as the company raced past $100 billion in annual sales.

As part of this process, Bezos delivered a memo, titled Amazon.love, to his leadership team at a retreat. In essence, this memo outlines how he wants Amazon to conduct itself and be perceived by the world.  Bezos wrote, “Some big companies develop ardent fan bases, are widely loved by their customers, and even perceived as cool. For different reasons, in different ways and to different degrees, companies like Apple, Nike, Disney, Google, Whole Foods, Costco and even UPS strike me as examples of large companies that are well liked by their customers." 

Bezos then went on to make a list of why some companies are admired and others are loathed: 

  • Rudeness is not cool.

  • Defeating tiny guys is not cool.

  • Close-following is not cool.

  • Young is cool.

  • Risk taking is cool.

  • Winning is cool.

  • Polite is cool.

  • Defeating bigger, unsympathetic guys is cool.

  • Inventing is cool.

  • Explorers are cool.

  • Conquerors are not cool.

  • Obsessing over competitors is not cool.

  • Empowering others is cool.

  • Capturing all the value only for the company is not cool.

  • Leadership is cool.

  • Conviction is cool.

  • Straightforwardness is cool.

  • Pandering to the crowd is not cool.

  • Hypocrisy is not cool.

  • Authenticity is cool.

  • Thinking big is cool.

  • The unexpected is cool.

  • Missionaries are cool.

  • Mercenaries are not cool.

Jeff’s "cool” list struck a nerve because I’ve recently been spending a lot of time thinking about branding in the context of both RRE and the companies I’m fortunate enough to work with. Building an enduring and admired company regardless of stage and sector requires not only innovation but also strong values and morals to guide the way.