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Steve Schlafman

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Friday, December 1, 2017 - 7:30am

Yesterday, I was thinking back to my experience in high school. While I had some amazing teachers and treasure many of the lessons that I learned, I wish I had been taught more fundamental ‘life skills’ during my adolescence. That reflection prompted me to write the following tweet: Less than twenty-four hours later, the tweet […]

Saturday, November 25, 2017 - 5:05pm
Several months ago while I was on my Vipassana meditation retreat, I was captivated by the idea that change is a constant. By unplugging for ten days and increasing my sense of awareness, it became very apparent that objects around us and within us, even at the tiniest levels, are always in a state of […]
Wednesday, November 8, 2017 - 7:35am
(My dad this summer in Woodstock, NY) I recently read an excellent essay by Andrew Kortina titled, “They Say the #1 Killer of Old People is Retirement.” In this piece, he discusses the importance of finding purpose and meaning deep into life. Andrew outlines a confluence of factors that are causing mental and financial hardships […]
Monday, October 30, 2017 - 7:30am

Earlier this month, my good buddy, Mike Karnjanaprakorn, Founder / CEO of Skillshare, stopped by our place in the Catskills for a few hours. He was just coming off his seventh ‘Think Week.’ Over lunch, Mike explained the inspiration behind this annual ritual and outlined the basic structure he has used over the years. He even wrote a useful blog post about his experience a few days later.

Mike initially got this idea from Bill Gates, who takes these weeks several times a year to find inspiration and go deep into a few areas of interest. Bill would also read a variety of essays and briefs written and submitted by Microsoft employees and researchers. In fact, Bill dedicated one of his Think Weeks in the 90s to understand the coming wave known as the internet (see his memo, “The Internet Tidal Wave”). Several other friends have recently taken a Think Week. This includes Dan Teran from Managed by Q who swore by his experience diving deeply into the future of work.

Saturday, October 14, 2017 - 11:35am
Last week, I published a blog post titled, ‘Decoding the Qualities of a Great VC.’ The spirit behind the piece was to spark a conversation about what makes a good venture investor and whether that can be predicted. It was generally well received until I saw this Tweet from Nathalie Molina Nino, CEO of BRAVA […]
Tuesday, October 3, 2017 - 11:35am
Last Friday, I was talking with Parker Thompson of AngelList and creator of Startup L Jackson about a range of topics from investing in pre-seed companies to building a venture firm from scratch. Towards the end of the call, he asked what I thought are the attributes of a successful VC. Rather than answering on the spot because we […]
Tuesday, September 26, 2017 - 7:30am
10 Days of Silence for a Lifetime of Wisdom Dhamma Dhara, Shelburne Falls, Massachusetts Three weeks ago, I returned from a 10-day Goenka Vipassana meditation retreat at Dhamma Dara in Shelburne Falls, Massachusetts. Goenka (1924–2013) was a Burmese-Indian teacher of Vipassanā meditation. His teaching was notable for emphasizing that the Buddha’s path to liberation was non-sectarian, universal, and scientific in character. He […]
Thursday, September 21, 2017 - 5:10pm
Last weekend, I was hanging out at my twin brother’s house. It was early in the morning and wanted to kill some time so I decided to browse his vast book collection. I came across one of our most cherished books from childhood, Where The Sidewalk Ends by the legendary artist and writer Shel Silverstein. As I […]
Wednesday, August 16, 2017 - 7:35am

Everyone struggles with something. For me, it was anxiety, addiction and imposter syndrome. For a long time, I was afraid to seek help because I was worried about what others would think of me and how they’d react since I was extremely functional in all facets of my life. I ultimately healed myself and transformed my life over several years through mediation, nurtrition, radical candor, sleep, exercise and positivity. I also turned to a variety of support communities which were a huge source of strength, meaningful relationships and perspective. I credit much of my transformation to these groups. There’s no way I could have improved my mental health all by myself.

Saturday, August 12, 2017 - 7:30am
Last month, while I was on a cross country flight, I read Ray Dalio’s seminal document, Principles, for the second time this year. For those of you who don’t know Ray, he is the Founder of Bridgewater Associates, the world’s largest and arguably most successful hedge fund. Ray runs Bridgewater according to principles that he […]
Friday, August 4, 2017 - 7:35am

Countless times over the last decade, I’ve heard other venture investors refer to their investments as “bets.” Earlier in my venture career, I was absolutely guilty of this because I wasn’t being mindful and probably lacked some necessary empathy. At the time, I don’t think I truly appreciated what it meant and took to be an active investor and support a company over the long haul. A few years ago after a conversation with my wife, I began to question that vernacular.

Sunday, July 23, 2017 - 5:10pm
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 […]
Sunday, July 23, 2017 - 5:10pm
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 […]
Sunday, July 23, 2017 - 5:10pm
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. […]
Sunday, July 23, 2017 - 5:10pm
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 […]
Sunday, July 23, 2017 - 5:10pm
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 […]
Sunday, July 23, 2017 - 5:10pm
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. […]
Sunday, July 23, 2017 - 5:10pm
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 […]
Sunday, July 23, 2017 - 5:10pm
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 […]
Sunday, July 23, 2017 - 5:10pm
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 […]
People call me Schlaf. I'm a VC in NYC with RRE Ventures. My values guide me every day: intellectual curiosity, hard work, honesty, humility, empathy, and transparency. I blog about trends in tech, cool startups and life in NYC. You can follow me @schlaf.