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 Continue reading “Startup Pitch Decks”

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 this tweet into a blog post 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 Continue reading “Why I Invest”

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.

Apps and Digital Services

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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.

Apps and Digital Services

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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, Continue reading “Becoming more human through mass automation”

I am a social media addict and I quit for a month. Here’s my story.

Originally published on Medium on August 8th, 2016

ad·dic·tion əˈdikSH(ə)n/ (noun): a brain disease characterized by compulsive engagement in rewarding stimuli, despite adverse consequences.

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 Continue reading “I am a social media addict and I quit for a month. Here’s my story.”

My wife is a founder. Here’s how she has helped me become a better investor.

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.

Nearly four years ago, Eliza started The Sill after struggling to decorate our home with plants. The online options felt antiquated, uninspiring and purely transactional. The offline options weren’t any better. Plus they required serious plant knowledge and a fair amount of manual labor. As someone who always enjoyed plants and spent Continue reading “My wife is a founder. Here’s how she has helped me become a better investor.”

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 RebootVC 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-f0under of Techstars, decided to run a bit of an Continue reading “A bunch of VCs went on a retreat. Here’s what happened.”

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 Continue reading “Investing with a new purpose”

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 right 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, Continue reading “The lesson money couldn’t buy”

What I read in 2015

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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 Continue reading “What I read in 2015”

Introducing RRE’s New Director of Platform

Over the summer RRE kicked off a search for a Director of Platform. After reviewing hundreds of resumes and meeting with more than a dozen candidates, we were fortunate to find a candidate with deep operational chops, a innate passion for the startup ecosystem, a strong willingness to help founders and a super positive, team-first attitude. This candidate also demonstrated tremendous hustle, drive and raw emotional intelligence that our founders and partners deserve and expect in this role. With that being said, I’m incredibly excited to welcome Maria Palma to the RRE family and community.

Maria brings a wealth of operations, strategy and business development experience to the RRE community. Prior to RRE, Maria, was Executive Director of Business Development and Chief of Staff at NYC-based Eyeview. There she was involved in numerous aspects of the business including strategy, partnerships, and revenue to name a few. Before she joined Eyeview,

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Continue reading “Introducing RRE’s New Director of Platform”

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

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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 Continue reading “The Advice a Cabbie Gave Me The Day I Moved to NYC”

Don’t Congratulate Me For Writing A Check

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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 Continue reading “Don’t Congratulate Me For Writing A Check”

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 Continue reading “On Writing: Growth Through Resistance”

Hightower: The System of Record for Commercial Real Estate

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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 Continue reading “Hightower: The System of Record for Commercial Real Estate”

The Robot Factory & Digital Toys

Just a few days ago, Tinybop, the Brooklyn-based children’s app studio and RRE portfolio company, launched their latest creation, The Robot Factory. For those of you who don’t know, Tinybop is developing a magical constellation of apps for kids that is global, timeless and universal. The company’s goal is to create a global media brand that teaches kids in 150+ countries about the world through play, exploration and self-expression. Their fourth app, The Robot Factory, enables kids to build any robot imaginable from 50+ parts, test their cyborgs in a virtual world, and then proudly display their creations in a digital trophy case.  The purpose of the app is to let kids imaginations run wild and engage in open ended play.  The Robot Factor is the first app in Tinybop’s Digital Toy series.


Raul Gutierrez
, Founder of Tinybop, recently wrote about empowering kids to create and explore.  He Continue reading “The Robot Factory & Digital Toys”

Apple Watch Venture In Residence

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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 Continue reading “Apple Watch Venture In Residence”

Weekend Reading: The Designer Behind The NYC Subway Map

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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. 

In August 1972, the MTA unveiled a drastically different subway map designed by Vignelli. It showed the transit system as a series of straight lines that sometimes veered at 45 degree angles, rather than a more realistic tangle of curved paths. Most other metro systems in the world, such as London, used a diagrammatic, not a geographical approach.  New York, with its system of local and express trains, presents complications in mapping that no other transit system faces. Vignelli’s diagram, along with the MTA’s neighborhood maps that came along later, were intended to work together to guide customers through the system, then to their street destination. He later argued against that decision by saying the map should focus on the subway system and not include distractions like geographic references.

Millions of New Yorkers are exposed to Vignelli’s work on a daily basis and I’d bet few actually pause for a moment to appreciate its brilliance. Many of us take getting around the city for granted, but it’s a scary and intimidating place if you don’t know where you’re going. Vignelli’s simple and elegant designs helped make New York easier to navigate and a better place to live and visit. I’m fascinated and inspired by the designers, artists and thinkers that have helped shape New York City into what it is today. Vignelli is one of those people that I admire.  

I’ll leave you with this quote of his: 

“One of the problems they had in New York is that the people, they couldn’t relate the geography with the station, with the lines, and they were confused by that. But it’s just because they shouldn’t. There were neighborhood maps in the subway stations, so really there’s no reason why this map had to be literal—it could be completely abstract. But I think that it would’ve been even better if I had pushed the envelope even further and not had anything, just the lines and the stops.”

Transitions

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“Death is very likely the single best invention of Life. It is Life’s change agent.”

-Steve Jobs

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.  

In my own experience, career transitions have led to an incredible amount of personal growth. Most change forces us out of our comfort zone so we’re required to adapt. These moments provide us with a catalyst to learn new skills and explore new spaces. I’ve also found that transitions lead to meaningful new relationships. The people that we choose to spend our time with have a huge influence on our mental state and being. Building new relationships is one of life’s greatest gifts. Additionally, transitions provide an opportunity form new habits and break old ones. When we start something new, we can take a fresh approach and discard what hasn’t been working. Finally, being in a new environment often leads to enhanced creativity because we’re now able to see and connect more of the dots. 

Since I’ve been through a number of life transitions including a few very scary ones, I wanted to share some bitesized advice for dealing. Continue reading “Transitions”