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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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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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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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

Update My VC

Today we are launching Update My VC - a modern guide on how founders can easily update and keep in touch with your investors. At RRE we always strive to provide the best possible support to our companies, but we realize you’re slammed building product, growing your business and recruiting the best talent. We also understand the last thing you want to think about and have time for is sending a lengthly update to your investors. 

To make this process easier for you, we’ve created a Tumblr blog that outlines the perfect investor update. Our template includes Highlights, Lowlights, Product, KPIs/Core Metrics, Business Development, Hiring, Financing, Press, Help Wanted, and Kudos. The site even has an Email Template button that auto generates a blank investor update as a new email message.

Additionally, we’ve included a library of resources including useful blog posts, slideshares, and Quora discussions.  Our expectation is to update this library so the most useful content and advice is all in one place.  We view this as an evolving site and community so feel free to share your questions, comments and feedback with community@rre.com

Finally, I’d like to thank Amrit Richmond and Kane Hsieh from the RRE team for their help in launching this site. 

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. 

What I've read so far in 2014

One of my 2014 goals is to read at least one book per month. To help me achieve this goal, I decided to buy a Kindle Paperwhite so I could read on the subway and have an uninterrupted reading experience while at home.  Like many people, I’ve struggled reading books on Apple devices because the screen isn’t optimal and I’m constantly being distracted by notifications. The Kindle, which I think is the ultimate single purpose device, has changed my life because I’ve honestly never enjoyed reading so much. While I still have ten months until I achieve my goal, I’ve already read more books in 2014 than I did in all of 2013. Here are the books I’ve read so far this year: 

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Why Saying No Is Hard

Being an investor isn’t easy for a number of reasons. But the hardest part for me is saying “No.” I meet hundreds of entrepreneurs each year, and at RRE Ventures we invest in only a small percentage of them. VC’s generally invest in less than 1% of companies they meet. So if you do the math, you know I have to say “No” a lot.

There are countless reasons why we choose not to back an early stage venture. Market size. Wrong team. Bad timing. Competition. Traction. Lack of monetization. Little or no competitive advantage. Outside our expertise. Valuation. I could go on. 

But regardless of whether I exchange a quick email with a founder or spend hours getting to know him or her, passing is the worst. It’s the only part of my job that I truly hate. And it’s not just because I lose the option to invest down the road. I hate passing because my daily work with entrepreneurs has given me a good look into their struggles…what founders sacrifice daily to ensure that their company is in a better place tomorrow than it is today. It becomes personal, emotional…it's only human to feel for the founders who…

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Breather - Peace & Quiet on Demand

On Friday, all of my meetings were downtown but I had a two hour open window in the late morning.  Instead of schlepping to RRE’s office in Midtown East or sitting in a noisy Starbucks with spotty wifi, I decided to give Breather a try.  Breather is a newly launched mobile app that provides on-demand rooms in large urban areas. It is the brain child of Julien Smith a Montreal-based writer and entrepreneur.  The service currently operates in Montreal and NYC, costs $25 / per hour and is available seven days a week from 6am to 10pm. 

The main goal of the app is to provide a quiet place to hold a meeting, work in private or just take a break for an hour or two. While the service is perceived as “odd,” novel and unproven, I can imagine a growing market for this type of flexible space. Demand will likely come from small companies with virtual organizations, freelancers, visiting executives and employees and even tourists. The timing for something like Breather to emerge couldn’t be any better since asset sharing, co-working and freelancing have become important pieces of the innovation economy for nearly a decade. 

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Nuke Your Twitter Feed In The New Year

One of my 2014 goals is to remove clutter in life and focus on quality. This doesn’t just include physical items like clothing and other random “stuff” but also digital things like the number of apps on my phone or the blogs I actively follow. 

A few weeks ago I realized my Twitter feed was becoming unbearable.  Since 2007 I had followed more than 4,000 individuals, startups, established brands, parody accounts, celebrities and media companies.  The signal to noise ratio had pretty much hit zero. I couldn’t keep up. 

I finally decided to search for a solution that would help me quickly unfollow everyone so I could rebuild my follower list from scratch. The rationale was simple: start over and carefully curate the accounts I follow so my feed would become relevant once again. After all, Twitter is only as good as the people you follow. 

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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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QUESTION(NY)AIRE With Steve Schlafman At Lerer

New York City’s Silicon Alley has claimed a place among the ranks of top tech-hubs across the country such as Boston, Dallas, Seattle, and of course, its namesake and the “mothership”, Silicon Valley. While each of these start-up communities boasts its own set of advantages, Silicon Alley benefits from New York’s buzz and density people, which, in the past few years, has played into the hands of the social media phenomenon. Yet in many ways, the most important feature of any tech boom-town is the availability of funds.

Enter: the venture capital firm. Steve Schlafman is a principal investor at one of these firms, Lerer Ventures, which focuses on funding companies in the “seed-stage”. That is, Lerer trudges through the weeds of all start-up hopefuls to find entrepreneurs with “product vision, consumer insight, focused execution, and unwavering ambition.” Although he is now in the position of the lender, Steve is no stranger to the experience on the other side of the table. His work experience spans from startups such as Stickybits and Turntable.fm, to more traditional environments such as The Kraft Group and Microsoft.

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