I'm Social Media Addict And I Quit For A Month

A few months ago, I was completely overwhelmed. My brain felt like it was on overdrive and I was having difficulty processing tasks and information. There were just too many inputs bombarding my brain. Too many meetings and events. Too many emails. Too many articles. Too many apps. Too many social media feeds. I couldn’t keep up and stay focused. I had reached a tipping point. Something needed to change. I knew I badly needed to reduce clutter and distractions from my daily routine. Several days after this realization, I began to track how I spent my time and paid close attention to those activities which caused stress and anxiety.

A week into this exercise, a number of things became abundantly clear. I was spending at least two to three hours a day on social media. Anytime I had a free moment, I’d reach for my phone to engage on Twitter, Facebook or Instagram. I’d often feel guilty because this time rarely felt productive and fulfilling. I also realized that more time in social media led to more digital clutter (articles to read, people to engage, companies to track). There was always a sense of FOMO (fear of missing out) gnawing at me so I was constantly checking my feeds throughout the day. It also occurred to me these apps took me out of the present moment. I’d constantly be thinking about my next post, stopping to capture that perfect picture, or ignoring whoever I was with. Worst of all, I realized social media was a vehicle to feed my ego, escape reality and flood my brain with quick bursts of dopamine.

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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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A Bunch Of VCs Went On A Retreat. Here’s What Happened.

This past weekend I had the good fortune of participating in the first Reboot VC Bootcamp. For those of you who don’t know Reboot, it’s a values-driven organization led by Jerry Colonna that primarily helps founders and their teams deal with the constant ups and downs of startup life. At the most fundamental level, Reboot is a personal development company that offers bootcamps, executive coaching, 360 reviews and a variety of other programs to help leaders discover their true selves. Reboot also publishes useful and powerful content including a phenomenal podcast hosted by Jerry. I can’t say enough great things about this organization, its team, and their mission.

This formula is the essence of Reboot:

PRACTICAL SKILLS + RADICAL SELF-INQUIRY + SHARED EXPERIENCES

= ENHANCED LEADERSHIP + GREATER RESILIENCY

Jerry and Brad Feld, a Partner at Foundry Group and Co-founder of Techstars, decided to run a bit of an experiment. Instead of facilitating a boot camp for founders, they tailored a program designed specifically for venture investors. Jerry and Brad have over forty years of combined investment experience. They’ve seen the good, the bad and the ugly. Most importantly, they deeply care about the startup ecosystem and believe in paying it forward. When they’re in a room together the discussion is always authentic, insightful and inspirational.

Over the weekend, sixteen investors from funds of all sizes and both coasts descended on Boulder, CO to speak openly about our challenges and to learn how to improve our interactions with our portfolio companies and the founders we work with. Jerry and Brad worked closely with the group to help us uncover our authentic leadership styles and provided practical skills for managing the array of feelings that can be triggered as we navigate the startup ecosystem. The goal of the weekend was to help each of us become the best board member, investor, supporter that we can possibly be.

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Investing With A New Purpose

Several weeks ago, I was hanging out with Lindsay Ullman of Sidewalk Labsand we were talking about some of the companies I’ve backed at RRE andLerer Hippeau Ventures. She paused at one of them and asked, “Do you believe this company is good for the world?” Candidly, I was caught off guard. I wasn’t expecting such a direct question and didn’t consider it much when I was making the initial investment. I didn’t know what to say.

Over the last few weeks, I’ve thought about my conversation with Lindsay at least a dozen times. Her question forced me to be honest with myself about the reasons why I funded this startup, and the rationale behind some of my other investments too. I realized that my investment philosophy had been slowly changing for some time, and our conversation was a kind of tipping point. I finally arrived at the following conclusion: If a company doesn’t solve a worthy problem and make the world a better place, then I have no business investing in it.

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The Lesson Money Couldn’t Buy

It was a warm spring morning in 1992. At the time, I was a pudgy and hyperactive seventh grader at Swampscott Middle School. The bell had just sounded and I was slowly meandering to my next class when my best friend, Josh Grab, intercepted me in front of the principal’s office. For some reason I can’t recall, he got in my face and began to push my buttons. I tried to continue on my way but Josh wouldn’t let up. He was relentless. He went on and on and on. After about three minutes, I had finally reached my tipping point and lost control.

In a flash, everything went white. Before I even knew what was happening, I turned around, made a fist and swung my arm with every ounce of energy I had in me. Instead of taking my frustration out on Josh, which I totally should have, I struck a plexiglass art display containing a chaos pendulum built by students at M.I.T. It was a perfect strike. As soon as my tightly clenched fist hit the display, I heard a crack and felt the large object buckle under the force of my haymaker. Within a second, I knew that I had broken something. Thankfully, it wasn’t my hand but then I realized it was an even worse outcome. The large plexiglass case splintered and one of the large panes split in half. The damage had been done. The severity of my stupid behavior hit home when I came to my senses and realized a group of my classmates were suddenly gathering in front of the principal’s office to witness my carnage.

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What I Read In 2015

Last holiday season, I shared my first annual reading list which was an overview of all the books I devoured in 2014. I’ve always been a big advocate for lifelong learning so I’m constantly trying to practice what I preach by reading one or two books at any given time. There’s no question it’s a big commitment but the investment pays off in so many ways. I find reading helps me go deeper in my work as a VC, develop greater self awareness, build historical perspective, and most importantly escape from the world. I’ve always believed that buying (and reading!) books is by far the best and most rewarding investment that anyone can make in themselves.

Many of the titles on the 2015 list were recommended by close friends, colleagues, Twitter followers and my wife. The topics ranged from innovation to healthcare, history, science fiction and urban planning. As you’ll see, I devoted a considerable amount of time learning about addiction since I decided to get sober in 2015 and led an extensive research project on the topic. Not only was I interested in the science of addiction but also the war on drugs, the rehab industry and new approaches to treatment.

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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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Don’t Congratulate Me For Writing A Check

On Thursday we announced our Series A investment in Managed by Q. Throughout the day, I received countless congratulatory emails and tweets from friends. “Amazing investment.” “Love that company.” “Nice win.” “HUGE CONGRATS.” And so on. On my way home, as I reflected on these kind messages, it occurred to me that I don’t deserve a pat on the back. There’s a long road ahead for the company, and I really haven’t done shit. Sure, I built a relationship with Dan and Saman, hustled to help Q win new customers and key employees, and gave them a generous term sheet. But writing a check is easy. Being an engaged board member and a supportive partner in good times and bad is the hard part. And building an enduring, category-defining company is nearly impossible.

Mark Cuban once said, “the magic in business isn’t raising money but making money.”

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On Writing: Growth Through Resistance

I have a confession to make. I hate writing. It scares the shit out of me. Since I started this blog a four years ago, I’ve had hundreds of ideas but they’ve remained stuck in my head. When I finally muster up the courage to start writing and I commit to a post, I tend to over analyze every word, every sentence, every paragraph. I always know what I want to write but the words don’t flow easily. Every post seems to take hours. The voice in my head is always doubting and questioning. What will people think of me? What if I’m wrong? What if my grammar is incorrect? Who will disagree with me? What if I offend someone? Who is actually going to read this? The simple act of writing comes naturally and is liberating for others but it’s paralyzing for me. That sucks. It feels awful. I’m sick and tired of holding myself back and giving in to the voice in my head. 

After some reflection over the last few weeks, I’ve decided that being open honest with myself and facing my anxieties will eventually lead to greater fulfillment and personal growth. For many years, I’ve used my phobia of writing as an excuse not to share my thoughts with others. This negative mindset has admittedly weighed me down with inaction, anxiety and self doubt. If I don’t fight this perceived weakness and face it head on, I’ll never be able to grow personally, improve as a writer and share my ideas with family, friends, colleagues and strangers. What a shame that would be. Those days are over starting right now. I’m making a commitment to myself to start writing more frequently. I’m finished caring what people think. I’m finished worrying about perfect grammar. I’m finished comparing my writing to others. I’m finished holding myself back. I want to grow. I want to share my ideas. I want to learn. I want to write from the heart. I want this for myself.  

Hightower: The System of Record for Real Estate

A few years ago, Brandon Weber, CEO and Cofounder of Hightower, and I were catching up over a casual dinner in Brooklyn. We had met ten years earlier when we started our careers at Microsoft and quickly became friends.  A few months before our dinner, Brandon left the commercial real estate (CRE) brokerage powerhouse CBRE, where we was a Vice President, to start Hightower because he saw that the industry was broken. He explained in fine detail the great paradox facing the industry. Despite CRE being a fifteen trillion dollar market and highly data intensive, many of the processes were manual and relied heavily on paper, excel and email.  Additionally, existing industry standard solutions such as Yardi, MRI and Argus were siloed and 20 years old. Brandon explained that he and his cofounders, Donald and Niall, were starting Hightower to solve these problems.

I was initially skeptical because I had seen dozens of real estate tech startups and many of them struggled to gain adoption with institutional landlords and brokers. CRE remained one of the major industries that hadn’t embraced the cloud and mobile.  My gut told me there was a huge opportunity because at some point in the near future “software would eat” CRE. After spending more time with Brandon and his cofounders, they convinced me the time had come and they were the right team to back.  They argued the market was ready because brokers and landlords were using iPhones, Google, Facebook and other cloud-based tools in their personal lives.  These customers now wanted and expected the same quality of tools at work.  As we dug deeper, it became obvious that Brandon, Donald and Niall were the right team to invest in because they had the unique blend of domain expertise and world-class product experience. A few months later, RRE Ventures was lucky to invest in Hightower’s seed round along with strategic investors Thrive, Bessemer, The Box Group, and Red Swan among others.

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Apple Watch Venture In Residence

In just two weeks from now, the Apple Watch finally comes to market after months of anticipation and speculation. You may recall back in November, Apple released its WatchKit SDK to developers and companies to ensure there would be a large selection of apps when the wearable computer hits the market. In fact, Tim cook wrote in a memo earlier this week that more than a thousand apps have already been submitted to the App Store. Based on intuition and early screenshots, many of the initial apps will be geared towards communication, news, payments, transportation, health and productivity. Like with any new platform, it’s mind bending to think about the range of apps and services that we’ll now be able to access with a flick of our wrist. 

The big question that everyone’s asking is: Does Apple still have the magic to create a category defining product that will ship hundreds of millions of units? People much smarter than me believe Apple Watch will be a flop. Additionally, many of the early reviews have been mediocre because the user interface has a steep learning curve. Taking a contrarian angle is understandable given we’ve become tethered and addicted to our smartphones and Apple Watch feels like a nice to have rather than a must have. I personally struggle with making predictions and betting against Apple before a single unit has shipped. What I do know today? Thousands of developers are building apps, Apple Watch is beautiful and hyper personal, and Apple is putting all of its marketing might behind the launch. In my limited experience, that’s a recipe that I probably wouldn’t bet against.    

Given the developer interest we’re seeing, I strongly believe that thousands of watch-specific apps will emerge over the next few years and several large companies will be built on top of this new platform. I don’t pretend to know what the winners will look like and where value will be created but I do know that RRE Ventures is eager to learn and invest in the ecosystem.  As part of this process, we’ve decided to establish the RRE Venture In Residence Program which will initially focus on Apple Watch.

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The Designer Behind The NYC Subway Map

This morning while I was browsing Fast Company Design, I stumbled upon a rare interview with graphic design legend, Massimo Vignelli. For those of you who don’t know Vignelli, he was a versatile Italian designer who worked across a broad range of disciplines including interior design, environmental design, package design, graphic design, furniture design and product design. Vignelli’s ethos was, “If you can design one thing, you can design everything.” His most famous body of work is arguably the New York City Subway Map and the New York City Transit Authority Graphic Standards Manual. 

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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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Shuddle: Scheduled Rides for Busy Families

When I was a kid my mom always used to complain how she had to schlep us around town. Often times she had to be in three places at once and finding alternative transportation wasn’t easy.  Not much has changed twenty years later. Talk with any parent today. Many will admit that safe and reliable transportation is one of their biggest challenges. The reality is households are busier than ever and the stay-at-home mom is a relic of the past.  

Last October I stumbled across an article in Recode that featured a new startup called Shuddle. The piece described Shuddle as “Uber for kids.” It occurred to me that Shuddle was trying to solve the transportation problem that has haunted families for decades. Several hours later, the article was emailed around the firm because the idea of providing safe and reliable transportation for kids resonated with the group. Everyone agreed that we had to meet this company.    

The following month, Rebecca Kaden of Maveron introduced me to Nick Allen, Shuddle’s Founder and CEO. Prior to starting the company, Nick co-founded Sidecar, a popular ride sharing application. At Sidecar, he observed many families were using Sidecar to transport their kids. Upon further research, he discovered that traditional ride sharing companies aren’t built to handle that customer segment.  They typically don’t have the right insurance and it’s against their terms of service since passengers must be at least 18 years old. In discussions with many parents, he discovered they don’t trust the existing brands since safety isn’t built into their products. While Nick isn’t a parent, it was clear to me after the first meeting that he was going to build the safest and most reliable transportation product in the world. 

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My 2014 Reading List

At the beginning of the year, I set a goal to read one book a month in an effort to break free from my routine of reading only tech and startup blogs. My wife, Eliza, had also been trying to get me to read more fiction in the seven years we’ve been together. This seemed like a goal worth pursing and easy to accomplish with very little effort. 

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Products I Couldn't Live Without in 2014

Every year around the holidays, my buddy and fellow Patriots fan, Ryan Spoon, compiles a list of his favorite products. I’ve always enjoyed reading his annual post so I’ve decided to follow his lead and curate my own list. Given I review and test hundreds if not thousands of new products each year, I’m fascinated by the ones that create enough value that I come back to over and over again.  These are the apps, tools and gadgets that cut through the clutter and ultimately made my life more productive, happier and healthier in 2014. 

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New Investment: theSkimm

About three years ago when I was at Lerer Ventures, I first met Carly Zakin, Co-Founder of theSkimm, through my friend Rob Fishman. At the time, she was working at NBC News as a Producer and wrestling with her next career move. We discussed a number of her options including joining a startup or building one from scratch. Later that winter, Carly was back in my office explaining that she was hours away from quitting her job to start a media company with her best friend Danielle Weisberg. Carly and Danielle ultimately launched theSkimm because they could not ignore a huge void in the market — they saw that their friends, who are intelligent and super busy, were not engaging with news in a way they enjoyed, fit into their routine, or made them keep coming back for more. 

theSkimm is the first company that has been able to transform news and information into a lifestyle brand.  The team is obsessed with making it easier to be smarter and finding ways information can be streamlined into their audiences routines. Their first product, the Daily Skimm, is an email newsletter that arrives in your inbox every morning and provides all the news you need to know for the day. In essence, theSkimm is recreating what morning television means for their target audience. The numbers prove that Carly and Danielle are on to something big. theSkimm now boasts more than one million active readers, thousands of volunteer Skimm’bassadors in more than twenty cities, and an authentic voice that its readers trust. 

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Radical Transparency: Review Me on Dunwello

Earlier this year, Dunwello, a review and ratings site for people, quietly launched to provide more transparency into how effective people are at their jobs. The service is the brainchild of Boston-based serial entrepreneurs, Matt Lauzon and Matt Brand. They founded the company on the core belief that every person at every company should be both happy and productive. In essence Dunwello is a lightweight review platform that enables anyone to receive “micro feedback” from customers, colleagues and partners. If Yelp and Glassdoor are used for reviewing businesses, Dunwello is used to review people at businesses. Think of it as a Net Promoter Score (NPS) for professionals. The company is currently targeting beauty stylists and fitness coaches but just about any worker can have a profile: therapists, lawyers, doctors, freelancers, handymen, cleaners and even VCs.

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How I Meditate

This Q&A originally appeared on the Lift App blog

Why did you start meditating? What was your goal?

I started to meditate because I desperately wanted to spend less time in the past and the future and more time in the present.  Additionally, I tend to be a very anxious person so I was looking for a daily practice that ground me and calm my mind.  When I initially started, my goal was to practice least once a day and record how I felt after each session. I found it very easy to incorporate it into my daily routine.

What is your meditation routine?

The style of meditation that I learned is called Vedic. The idea is to practice twice a day for about twenty minutes.  I’ve adopted that schedule and have found it super easy to incorporate into my busy life.  I’ve made this a priority so each day I block out enough time to make sure I get in my fix.  In the morning, I’ll roll out of bed, drink a glass of water and immediately start my practice.  No email.  No TV. Just water and mediation. It’s the first thing I do every day.  In the afternoon when I’m about to hit a wall and I usually reach for sugar and caffeine, I’ll lock myself in a conference room or my office for a quick session. Before I started to meditate I’d usually take fifteen to twenty minutes in the afternoon for coffee so finding a bit of extra time wasn’t an issue.

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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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