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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On Privilege

Last week, I published a blog post titled, ‘Decoding the Qualities of a Great VC.’ The spirit behind the piece was to spark a conversation about what makes a good venture investor and whether that can be predicted. It was generally well received until I saw this Tweet from Nathalie Molina Nino, CEO of BRAVA Investments, an investment platform that cares less about creating the next woman billionaire and instead backs businesses that create wealth for a billion women.

I immediately became defensive because I had good intentions in writing the post and felt I highlighted ‘universal’ attributes of great investors. Without giving it any thought, I quickly replied to Nathalie with the following tweet.

I then felt a backlash from a number of individuals including Katherine Gordon, Founder of The 3% Conference.

At that point, I became uncomfortable because my ignorance was obvious. Growing up in a predominately white upper middle class town in Massachusetts, I was indirectly taught that privilege was about wealth rather than race, gender, sexual preference, etc.. I incorrectly believed I wasn’t privileged because a) I was raised by an amazing single mother who worked two blue-collar jobs, b) I’ve earned an income since my early teens, c) I financed my college education, d) and I’ve worked hard to be self supporting for nearly two decades. It dawned on me through those various exchanges that I have been eating my own bullshit. What I began to quickly realize is that wealth is just one component of privilege and arguably the weakest one.

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Hug O' War

Last weekend, I was hanging out at my twin brother's house. It was early in the morning and wanted to kill some time so I decided to browse his vast book collection. I came across one of our most cherished books from childhood, Where The Sidewalk Ends by the legendary artist and writer Shel Silverstein.

As I was flipping through the book, I arrived at one of my favorite poems, Hug O' War: I immediately Google'd Hug O' War to learn more about what inspired Shel to write the poem. I discovered that he wrote it to widely express nonviolence and goodness to the world.  That expression really resonated with me.

As I reflected on the poem, the words non-violence, cooperation, winning, surrender, love, happiness and goodness kept coming up for me. I felt those words accurately represent what I value as a human being.

Yesterday, I walked into a tattoo parlor near Chinatown in San Francisco and had Shel's Hug O' War illustration etched on the back my arm. My hope is that it'll serve as a reminder to always love, support, serve and cooperate rather than to fight, harm or hurt. Here's to filling the world with more kindness. I can't think of a better purpose than that.

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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)

Why I Invest

Last Friday night after a long week, I decided to go for a long run and listen to a Buddhist lecture on the true nature of existence and the self. About ten minutes into the run, I started to contemplate why I have chosen various paths in life such as becoming a venture investor. Since I have decided to make this my life’s work, I began to examine what really drove this long-term decision and whether I was being honest with myself. As soon as I returned home and showered, I opened up my computer and published the following tweet.

Ryan Hoover of Product Hunt was the first to reply and suggested that I expand on the tweet and provide commentary and context on each one. I hadn’t considered writing a post, but ultimately decided it would be enlightening and cathartic to dive into each reason and expose myself.

Below is an expanded view into all the reasons that I have chosen VC as a career. I’ve also tried to be honest about what drives me. While this list captures how I feel today, I’m sure it will evolve over time as I learn more about myself and my worldview changes.

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My Favorite Products Of 2016

As a professional investor and lover of things, I’m constantly testing new products and sharing my thoughts with coworkers, colleagues, family and friends. This is a daily ritual and one that I’m passionate about. On occasion, I’ll fall in love with a product because it fills a void and finds a way into my routine.Thankfully, 2016 was packed with super useful and enjoyable products that were made with an insane amount of time, love and care. These products connected me, challenged me, educated me, inspired me, and even fed me. Below is a fairly comprehensive list of the digital and physical products that I enjoyed and couldn’t have lived without in 2016.

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Becoming More Human Through Mass Automation

Earlier this week. Amazon announced their latest innovation, Go. Think of Go as a futuristic grocery store. Using sensors, artificial intelligence and computer vision, Amazon is reinventing the shopping experience that we’ve all grown accustomed to for the last seventy years. That’s right. No more check out lines, registers or cashiers. If you want to buy an item, just grab it from the shelf, and then Amazon will automatically add the item to your virtual shopping cart. When you walk out of the store, Amazon will magically charge you for that item. Amazing, right? Yup. It’s also potentially scary when you think of the implications that this, and other forms automation, could have on our society.

Many industries are facing unprecedented changes largely driven by increasing wages and advancements robotics / artificial intelligence. This trend isn’t just limited to retail in the Amazon example but also transportation, food service, manufacturing, and administrative to throw out some examples. The number of jobs on the line is potentially massive. There are 3.4M cashiers nationwide according to the Bureau of Labor Statistics (BLS). There are 3.5M professional truck drivers in the U.S. according to the American Trucking Association. There are 4.7M food service workers in the U.S. (BLS). These are just a few examples. I don’t even need dig up all the numbers to conclude tens of millions of American jobs are at risk due to rising labor costs and automation.

All that said, I’m not here to paint a doomsday picture like many before me have. Hundreds if not thousands of articles have been written about our robot overloads and how we’ll eventually become slaves to them. I’m also not here to look at what we stand to lose. Instead, I’m here to look at what we all stand to gain in a world of mass automation. I believe if managed properly this massive shift could unlock enormous long term opportunities for our society and increase our overall quality of life.

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