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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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.  

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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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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Tinybop: Educating Kids In Every Country

Several years ago when I was at Lerer Ventures, Sam Gerstenzang, our summer intern, recommended  that I meet with Raul Gutierrez, Founder CEO of a Brooklyn-based creative studio called Tinybop.  When Sam explained that Tinybop was building educational apps for kids, I was immediately skeptical because I’ve seen hundreds of companies in the space and my identical twin brother founded a children’s media studio, CloudKid.  After some back and forth with Sam, I begrudgingly agreed to meet with Raul but promised that I would keep an open mind. Over the course of the next two years, Raul and I spent countless hours talking about the future of children’s media and his vision for building the next great education brand.  To Raul’s credit, he was able to transform me from a skeptic to a believer.  Despite the space being hyper competitive with thousands of app publishers, I truly believe that Tinybop is the one percent of the one percent.  That’s why I’m incredibly excited and proud to announce that RRE has led Tinybop’s Series A Financing with participation from TwoSigma, KEC, Brooklyn Bridge Ventures and Kapor Capital.  

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Standards of Performance & Organizational Values

I recently finished reading the seminal leadership book, The Score Takes Care of Itself, by Bill Walsh, the legendary 49ers Head Coach. In 1979 when Walsh took over the 49ers, the franchise was the laughing stock of the NFL as it managed to win only two games that season. However, in less than two years, Walsh led the 49ers from last place to Super Bowl Champs. A true Cinderella story. When Walsh left the franchise ten years later, the team had won three Super Bowl Championships and completed perhaps the greatest run in NFL history. 

How did Walsh fuel this transformation and build one of the great NFL dynasties? He credited his “Standards of Performance” as the catalyst for driving organizational change and maintaining a high level of performance during his tenure with the team. Walsh codified his “Standards of Performance” and drove them throughout every level of the organization including the administrative staff.  Within the first year, there was a dramatic shift in the way that everyone approached and performed their jobs.  Nothing short of excellence and a team first attitude would be tolerated.  

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On Demand Everything

A few weeks ago, I wrote about the “Uberfication” of the U.S. service economy. Given the positive response from founders, investors and the broader tech community, my partners at RRE invited me to speak about this investment theme at our annual meeting this afternoon.  As part of my talk, I prepared a high level presentation which summarizes the opportunity (see embed below).  As always, would love to hear your questions, comments and / or feedback.  We’re always looking to get smarter about how mobile is simplifying our lives and reshaping our economy.     

https://www.slideshare.net/schlaf/on-demand-everything

Uberification of the US Service Economy

Since I joined RRE Ventures last fall, I’ve spent time researching mobile on-demand services that we are able to access with a push of a button. “On-demand mobile services” (ODMS) is a broad category so I believe it’s important to start with a definition.  My friend Semil Shah defines ODMS as “apps which aggregate consumer demand on mobile devices, but fulfill that demand through offline services.”  I’ll take it one step further:  ODMS deliver a “closed loop” experience by collapsing the value chain including discovery, order, payment, fulfillment (offline but within owned network) and confirmation. In the pre-mobile era we had to search yellow pages (or google), find a provider, call  or email that provider, wait to connect with someone, schedule a convenient time, hope the provider arrives on time, and then pay with a credit card or cash.  Thankfully, a new array of mobile services removes all of that friction we were used to experiencing. Welcome to the uberification of our service economy.

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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. 

Nail Your Seed Round

Several years ago I started teaching a class on raising seed capital at General Assembly and Skillshare.   I initially created the class because friends and founders were coming to me for fundraising advice and I was answering generally the same questions over and over.  

A few months ago, I realized the initial slideshare that I used for dozens of classes was good as long as there was a voiceover but not great as a standalone guide. I decided to speak with a handful of my students and founders to see what they would want in a v2 fundraising resource.  

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My Goals for 2014

A mentor once told me that I should always jot down my intentions and goals so I can hold myself accountable and track my progress in life. Despite this sound advice, I’ve never taken the time to write down my personal and professional goals even though I always enjoy discussing them with others during the holiday season.  

With 2014 less than a day away, it’s time to finally buck this trend and put the proverbial pen to paper.  I’m doing it for three reasons.  First, I intend to check this list throughout the year to see how I’m doing relative to what I think is important right now.  Second, if I make my goals public, I’ll likely feel a big sense of failure if I don’t tackle everything I set out to accomplish.  Finally and most importantly, I hope you’ll get to know me better based on the areas I’m focused on and the things I’d like to achieve in 2014. 

Without further ado: 

Life    

  1. Read one book per month: Because reading tech and business blogs alone doesn’t really feed my brain.   
  2. Travel to two new countries: I’ve found the best way to learn about the world is by experiencing it. 
  3. Volunteer twice per month: Adopt a non-profit and contribute on a monthly basis so I can give back and feel good about it. 
  4. Attend two intensive classes: Explore areas of interest such as painting, cooking, and graphic design.  
  5. Spend less time working at home: Throughout 2013 I spent more time at home working than being focused on my life. 
  6. Get rid of clutter and focus on quality: I find the more “stuff” I get rid of the happier I become (e.g. clothes, twitter followers, etc.).
  7. Build a long term financial plan: I’ve been fortunate to save some cash but now I need to devise a long term investment plan. 

Work

  1. Blog monthly: I’ve had a longtime phobia of writing and it is time for me to get over it. 
  2. Take fewer meetings: In 2013 I took thousands of meetings so I’d like to cut that number in half and spend more time thinking, researching and creating. 
  3. Find a coach / mentor: It has been years since I have had a formal mentor and my gut tells me now is the time to find one. 
  4. Help a founder daily: assist a new founder every single day and expect nothing in return.  
  5. Launch a resource for NYC Tech: I’d like to create a new resource for the NYC tech ecosystem (think online community, newsletter, etc.). 
  6. Invest in fewer companies: I plan to be hyper selective in 2014 so I can focus on providing high-touch support to my founders. 
  7. Build RRE brand: I’m going to implement a half dozen ideas to foster community within the RRE portfolio as well the NYC tech ecosystem. 

The Guide to NYC Tech 2.0

At Lerer Ventures I created the first version of The Guide to NYC Tech after dozens of people asked me the same dozen questions, over and over. What are the best co-working spaces? Which lawyer should I hire? Where are good places to take a meeting? Who are the key investors to know? How do I find out about cool events?  

As much as I enjoy helping people one-on-one, I find it far more satisfying when I’m able to develop and share a resource that can be enjoyed by all New Yorkers and those in other tech communities interested in our ecosystem.  

Eighteen months after publishing V1, and just four months into my role at RRE Ventures, I’m pleased to present The Guide to NYC Tech 2.0.  Yes, it’s a guide to NYC Tech; and yes, it’s a bit of a love letter as well. But, I’ll say this: NYC is better poised now than ever before to make a global impact through entrepreneurship and innovation.

The goal of this guide is to raise awareness of the NYC tech ecosystem and help newcomers (and veterans) navigate the ever changing landscape.  Additionally, I hope it inspires everyone to give back to their own tech communities on a weekly basis. 

Finally, feedback is greatly appreciated so feel free to email me at schlaf55@gmail.com and I’ll try my best to incorporate your suggestions. 

I'm Joining RRE Ventures!

After two exceptional years of seed investing at Lerer Ventures, I’m excited to announce that I’ll be joining RRE Ventures in September as a Principal focused on Series A investments. 

RRE has been at the center of New York’s start-up community since the early 90s and now manages approximately $1 billion in committed capital across five funds.  There are very few NYC-based firms today with more experience finding great founders, helping entrepreneurs, and building awesome businesses. The partners at RRE have invested in innovative companies like Betaworks, Makerbot, WisdomTree, Vine, Paperless Post, Quirky, Bark Co. to name a few. 

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