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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Transitions

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.