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 and expose myself.
Below is an expanded view into all the reasons that I have chosen VC as a career. I’ve also tried to be honest about what drives me. While this list captures how I feel today, I’m sure it will evolve over time as I learn more about myself and my worldview changes.
Challenging: I’ve learned that it’s really damn hard to be a great venture investor. One needs to be conversant in many disciplines and have a variety of skills: networking, negotiating, spotting trends, reading founders, understanding psychology, maintaining conviction in the face of opposition, providing advice, analyzing markets, supporting my founders and partners, etc. Additionally, venture is incredibly dynamic because the world is always changing. There are many variables are outside of my control that need to swing in my favor in order to be successful. The only thing I really have control over is my investment decisions. If I’m honest with myself, the difficult nature of this business fuels my engine because I’m afraid of failure.
Competitive: Somewhat related to my first point, venture is insanely competitive. In fact, one could make an argument that our business is more competitive today than ever before. Billions of dollars have flowed into the asset class over the last five years. There are now hundreds of early-stage firms and accelerators all over the country looking to invest in the next great company. Dozens of firms are building insanely talented teams, value-creating platforms and deep networks that span geographies and sectors. I was taught at a young age to embrace competition because it forces me to look in the mirror, adapt and improve. I’d also be lying if I didn’t admit my ego loves to win.
Intellectual: While early-stage VC is technically within the realm of finance, it requires knowledge that extends well beyond any one field: technology, product development, design, branding, psychology, history, mathematics, manufacturing, supply chain, marketing, operations, and human resources.Depending on the company and pitch, I often rely upon a combination of these disciplines, many of which I’m still figuring out. That’s why pattern recognition is so important. Within a given year, I’ll see more than a thousand companies and meet with hundreds of founders. During this span, I’ll make millions of snap judgements and “micro decisions” that results in only a handful of investments. Because markets are constantly changing and innovation never stops, I need to rely upon my intellectual curiosity and desire to learn to keep up.
Social: Early-stage VC is so heavily dependent on working with, helping and understanding people. There are hundreds of social interactions per day across a variety of mediums — in person, on Twitter, over email, etc. The job relies upon a range of social skills and draws out a range of emotions each day. I’ve found being a good communicator and having empathy are two of the most critical skills since this is a human-driven business. I receive so much energy from founders, my partners, other investors, friends and family. I love it. Thankfully, my super power in life is connecting with people.
Inspiring: On a weekly basis, I meet with dozens of founders who believe they’re going to succeed and build something that impacts the world. That’s inspiring. I also witness portfolio companies start from nothing and become large companies that employ hundreds of lives. Finally, I have a front row seat to see my founders develop as leaders, grow their skills and overcome adversity.
Humbling: Building companies is really fucking hard. Not all of them succeed and become unicorns. Whenever I lead a new investment, I usually trick myself into thinking it’s the greatest company ever, but try to understand the opportunity and risks going in. In reality, it’s impossible to predict exactly what is going to happen. Since the large majority of startups fail, investors have to deal with the fallout of our decisions. I’ve had plenty of investment ideas that never materialized. I’ve made a number of investments that went to zero. I’ve had LPs tell me no. It’s pall art of the game. When things don’t go as I expected, a big serving of humble pie is a nice reminder that I’m far from perfect, I have way more to prove, and I have a lot of work ahead of me.
Impactful: VCs play a primary role in deciding what gets funded. We can be enablers and supporters of change. I’ve come to believe that we have an ethical and moral responsibility to be supporters of positive change. While we’re not the builders and creators of change, we vote with our dollars and help advise the companies that are making a dent. Seeing the impact is extremely gratifying. It’s not just about the growth of the company and the benefits to society, but also the growth of the founders and people involved. Driving impact is a huge reason why I love being an investor.
Teamwork: I believe VC is a team sport. Most firms are collections of personalities and experiences. Our long-term success depends on the investment decisions that we make as a team. Our success also depends on the group collectively supporting our portfolios and building the firm. I’ve always believed that our brand is built by the sum total of the positive and negative interactions that founders have with our firm. I’ve always loved team sports like football because everyone has to work together and do their jobs to achieve a common set of goals. VC is no different.
Money: I’d be lying if I said that money wasn’t important. It is. I also realize that money provides freedom and the means to acquire things but doesn’t create happiness. The latter is really what matters. For me, I value freedom and experiences. I didn’t come from a wealthy family. My mom worked two jobs. I paid my way through college. I suppose I chose a career that pays well so I can have freedom and hopefully not have to worry since I’ve seen what that looks like. Perhaps, I’m driven by a deep-rooted fear that stems from childhood. Regardless of what drives me, we’re in the business of making money for our Limited Partners so we need to drive returns and make money for them.
The Hustle: VC is a ground game. It’s won out on the street. Working from the office all day won’t lead to results in my opinion. To be great, I believeit’s a 24×7 job. Blogging. Producing events. Networking. Emailing. Taking meeting after meeting after meeting. Going to conferences. Hosting board meetings. Attending dinners and meetups. Reading blogs, articles and books. And so on. The frenzy is easily one of my favorite aspects of VC.Perhaps my hustle stems from my fear of failure (read: anxiety) and desire to win (read: ego) but nonetheless I enjoy the grind.
Determined: I’ve always had a bit of a chip on my shoulder which helps me as a VC. I was obese as a kid. I grew up in a competitive household. I wasn’t a top student in middle school or high school. I basically flunked my SATs. I didn’t attend a top tier college or get an advanced degree. I haven’t founded a billion dollar startup. All of these and more drive me. Ever since I graduated from college, I’ve been determined to succeed in my career and in life. I’ve done that by working my butt off, being intellectually curious, treating others with respect and honesty, and trusting my instincts. Bottom line: I’m determined to be a great investor by being a good partner at RRE, supporting my founders who are creating impact, and driving returns for our investors who pay us to be great.
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
- Overcast.fm: I spend hours each day listening to podcasts while I’m wandering around the city. Overcast is my go to podcast player.
- Digit: my favorite automated savings bot. Over the last few years, Digit has helped me save thousands of dollars without having to think or plan.
- Audible: In addition to podcasts, I enjoying listening to audiobooks. Audible has a great selection at an affordable monthly subscription.
- Zwift: I’m able to keep my legs in shape during the winter thanks to this virtual world and community for indoor cycling.
- Waze: This year I put nearly 20,000 miles on my car. I’ve turned to Waze nearly ever mile not only to save time but also to avoid speed traps and to receive roadside alerts.
- Amazon: It seems like Amazon packages find their way to my doorstep and office on a weekly basis. I’m hooked.
- Calm: With dozens of meditation apps out there, I turn to Calm to time and track my meditations. I enjoy its simplicity and range of features including breathing exercises.
- Strava: I track all of my bike rides and runs using this app. My favorite part of Strava is the community that provides encouragement and challenges me to pick up my game.
- Apptiv: Over the summer, I started to run again but I found myself having a hard time getting back into shape. Apptiv’s audio workouts have helped me increase my speed, stamina, flexibility and general health.
- Outlook: I practically live in my email and calendar. I’ve tried just about every productivity app on the market and found Outlook to be the simplest and most reliable.
- Brain.fm: Whenever I need to focus and get into a zone while I work, I turn to Brain.fm. Their audio programs are designed to stimulate the brain and help the listener focus.
- Pandora: I found myself completely overwhelmed by Spotify in 2016 so I decided to give Pandora another try. I’m glad I did.
- Giphy*: Very few sites bring me as much joy. Who doesn’t love receiving and giving gifs?
- Dashlane: I found myself reusing passwords and storing them in a document on my hard drive. This lax approach was a security risk so I turned to Dashlane to secure my digital life. I’m glad I did.
- Instagram: Still my favorite social app. Thankfully, this app wasn’t ruined in 2016 by fake news or pro-or-anti-Trump rants.
- Eero: Who doesn’t love wall-to-wall wifi. Eero blanketed our house with a fast and reliable wireless connection. No more dead spots.
- Snap Spectacles: The surprise hit of 2016. What a fun product. I’ve never been the type to capture video but that has changed thanks to Spectacles.
- Kindle: Still my favorite reading device on the planet. Nothing comes close.
- EO1 by Electric Objects*: A beautiful display for digital art. One of my favorite products of the year.
- Bose Quiet Comfort Headphones: Whether I’m on a plane or at work, I turn to these headphones to drown out all surrounding the nose and deliver high quality audio.
- Apple TV: While I feel this device has fallen short of expectations and its potential, we use this product almost daily to watch movies, TV shows and YouTube. It has helped us cut the chord.
- Wahoo Kickr: This smart bike trainer helps my legs stay conditioned over the winter. The Kickr is loaded with sensors and software to replicate the sensation of riding on the road and apply leg crushing resistance.
- Hydro Flask: Earlier this year, I found myself wasting money on bottled water and accumulating waste so I invested in a Hydro Flask. I never leave home without it.
- Trek Domane 5.2: My big bro has been cycling for years and finally convinced me to make an investment in a road bike. With the help of my friends at FitWerx, I selected the Domane and couldn’t have been happier. In 2016, I rode 1,5000+ miles without any issues.
- Foam Roller: The perfect companion that helps my body recover from tough workouts. I can confidently say that not one product has brought me so much pain and joy as the foam roller.
- All Birds: These wool running shoes were a welcome addition to my wardrobe this fall. Probably the most comfortable and warmest shoes I’ve ever owned.
- Topo Designs Fleece: The warmest and coziest piece of clothing that I purchased in 2016.
- Hamilton: Everything about this show is genius. I can’t stop listening to the soundtrack. I’m obsessed.
- Captain Fantastic: Probably my favorite movie of the year.
- FIFA 2016: I don’t think there’s one game that has brought me as much excitement and heartbreak at this one. EA Sports continues to deliver a masterpiece year in and year out.
- Grand Theft Auto 5: While I don’t like violence and don’t have much free time to play video games, I’m having a blast playing the latest installment of GTA.
- The Exponential View: One of my favorite new newsletters of the year curated by Azeem Azhar. It covers emerging technologies that drive exponential change.
- Rad Reads: A solid weekly newsletter by Khe Hy that aggregates articles on living a fulfilled life.
- TheSkimm*: My go-to morning news briefing.
- CB Insights: A daily email that covers company financings, industry research and other tech trends.
- Launch Ticker: A daily email that covers general tech news, product launches and transactions.
- Hip Sobriety: I read everything Holly Whitaker publishes because she’s so authentic and passionate about helping people overcome challenges in life like addiction and depression. She’s a bad ass.
- Andy Stanley Leadership Podcast: A podcast devoted to leading and managing organizations. Easily my favorite new podcast of 2016.
- This Week In Startups: While the host, Jason Calcanis, can be annoying at times, the interviews are generally excellent and insightful about startups and trends in technology.
- Reboot: A podcast that showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. Listening to these is very therapeutic and helps me empathize with others in the startup ecosystem.
- Origins by Notation Capital: A podcast about Limited Partners, the people who back Venture Capital firms. Good insight into an area that doesn’t get much coverage in the venture ecosystem.
- How I Built This: a podcast about innovators, entrepreneurs, and idealists, and the stories behind the movements they built. Super inspiring and interesting to see how some of the best companies were built.
- 20 Minute VC: a podcast hosted by the youngest and hardest working venture capitalist, Harry Stebbings. Harry talks with VCs, founders and startups execs.
- Sapiens: A detailed history of homo sapiens. Easily my favorite book of 2016.
- Powerhouse: The untold history of Creative Artists Agency (CAA). Changed the way I think about the entertainment business and entrepreneurship.
- Leading: Sir Alex Ferguson, the former manager of Manchester United, shares his perspective on leadership and building sustainable winning organizations. Reminded me how principles, values and discipline drive long term sustained success.
- Complexity: This books documented the creation of The Santa Fe Institute and examines how the top minds in computer science, physics, economics and biology came together to examine complexity theory. Reinforced how everything in the universe is somehow interconnected and is driving towards more complexity.
- Healing & Recovery: A collection of holistic lectures focused on recovery in its fullest sense — mental, physical, psychological and spiritual. Realize the mind controls our general health more than we believe.
- When Breath Becomes Air: After a young, talented neuroscientist is diagnosed with terminal cancer, he penned this memoir about life and death. Insanely moving. A good reminder how fragile life is.
- Supermind: A nice overview of how transcendental meditation boots performance and leads to a happier life. As someone who has a daily practice, it was fascinating to learn about the science behind meditation.
- Work Rules: Lazlo Bock, Former SVP of People at Google, provides a behind the scenes view into how Google manages Human Resources. After reading this book, I recommend it to all of my founders because it’s packed with useful tips and strategies.
- Justin’s Maple Almond Butter: My single favorite food in the world. I’d eat some with every meal if I could.
- Ritual Chocolate: My favorite small batch chocolatier that I discovered when I was visiting Boulder.
- Lofted Coffee: I’ve fallen in love with this roaster out of Brooklyn. Every cup of coffee I’ve brewed from their beans has been nearly perfect.
- Fever Tree Ginger Beer: Since I don’t drink alcohol, Fever Tree and a slice of lime is my beverage of choice.
- Van Leeuwen Ice Cream: I’ve tried hundreds of ice cream brands all over the globe. Van Leeuwen delivers the most consistent, simplest and highest quality ice cream I’ve ever tasted. I’m a fan boy.
Thanks for taking the time to read. I’d love to know which products you love and / or I should try in 2017. Happy new year.
*Full Disclosure: RRE is an investor in Giphy, Electric Objects and theSkimm
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, and administrative to throw out some examples. The number of jobs on the line is potentially massive. There are 3.4M cashiers nationwide according to the Bureau of Labor Statistics (BLS). There are 3.5M professional truck drivers in the U.S. according to the American Trucking Association. There are 4.7M food service workers in the U.S. (BLS). These are just a few examples. I don’t even need dig up all the numbers to conclude tens of millions of American jobs are at risk due to rising labor costs and automation.
All that said, I’m not here to paint a doomsday picture like many before me have. Hundreds if not thousands of articles have been written about our robot overloads and how we’ll eventually become slaves to them. I’m also not here to look at what we stand to lose. Instead, I’m here to look at what we all stand to gain in a world of mass automation. I believe if managed properly this massive shift could unlock enormous long term opportunities for our society and increase our overall quality of life. While there’s no doubt some pain will be felt in the short to mid-term, humanity has faced several major technological upheavals over the last thousand years and we’ve walked away every time with higher productivity, more time to focus on new activities and a higher quality of life. The mass automation era will be no different.
But first, how do we get there? Implicit within the concept of mass automation is the reality of significant structural unemployment. People will lose jobs, and those people will need to find new ways to support themselves and to support their families. This means several things, not all of which are bad. First, there’s a huge opportunity that exists around education and retraining. Retraining programs — if executed effectively — will yield not only a growth in talent available for existing American industries, but also an enormous increase in human capacity to tackle new or unsolved problems. As mass automation sets people free from menial work, socially, economically, technologically, and globally meaningful issues will become practically relevant in way they’ve never been before.
Of course, government and private retraining programs will hardly be enough to convert the millions of displaced laborers into newly productive workers in emerging industries, but they are a good start. Business, governments, and non-profits alike are already thinking about how to solve this issue. They’ll continue to do so. And I expect they’ll be successful. But for now, let’s move on. Assuming a large portion of the population no longer needs — or is able to — work in “traditional” industries, what will they do?
That brings us to the most interesting ramification of mass automation. How will we fill our time? Maybe some portion of the population will sit on the couch, drink beer, and watch reruns of Seinfeld ad infinitum. But I have more faith in us than that. I believe that we will begin, evermore rapidly, to solve the problems which have long perplexed humanity. More minds will be put to work against the problems of climate change, for example. Hopefully we’ll be able to invent and implement new responses to large societal issues like poverty, crime, sickness, pollution, the list goes on. But the true promise of increased human capacity goes beyond any one problem. By freeing our time and resources and redirecting them towards our largest problems, we’ll be able to focus on helping one another. Building and rebuilding communities. Engaging with each other emotional and spiritually. Being of service to our fellows. Ironically enough, I believe that mass automation will give us the capacity to be more human.
On top of all that, we get to reimagine the concept of work. What if we didn’t get up each day — 5 days a week — and sit in an office from 9 to 5. What if we engaged with the projects, the people, and the pursuits about which we’re most passionate? What if we did that always? And what if we were compensated not for our hours, but for our impact? What if everyone was guaranteed a universal basic income so that they could focus on these things? Making this shift will be difficult for many of us, but with strong, affordable retraining programs, millions of Americans will be granted opportunities that most of us can’t imagine today.
In the world of mass automation we will have more time than ever before. I don’t believe that this time will be wasted. I believe it will be invested. In self-expression. In art. In education. In service to one another. I believe that our newfound freedom will lead not to the destruction of our society, but to its elevation. So when I hear about a fully automated supermarket, I think not about our robot overlords, but about our potential as humans, and about achieving that potential.
(Thanks you to my trusted RRE colleague Cooper Zelnick for editing this post)
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 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.
Studies have shown the negative effects of excessive social media exposure and usage. This blog post does a nice job summarizing some of the early research conducted. Here are some of the findings presented. In November 2013, as many as 350 million people were addicted to just Facebook.Additionally, a group of researchers discovered a clear relationship between extreme social media usage and mental health issues such as depression.There also seems to be a direct correlation between social media and anxiety. According to a survey conducted by the University of Salford, 51% of users surveyed thought Facebook and Twitter had ‘changed their lives,’ for the worse. 45% responded by saying they feel ‘worried or uncomfortable’ when they cannot access social media. Furthermore, another study discovered that 73% of people panic if their smartphone is misplaced. My experience and the data illustrate we’re becoming slaves to our devices and social networks.
Once all of these stark realizations set in, I made the decision to detox from all forms of social media for the month of July. Cold turkey. I promised myself that I would stay away from any app that had a social feed. Facebook, Instagram, Twitter, Snapchat, Swarm, Strava, etc. were all off limits. I knew removing this clutter from my life wouldn’t be easy and would likely be stressful but I’d have more time to myself and a greater peace of mind. Several hours later, I deleted every social app off my iPhone. I then went to those sites on my desktop browser and logged out of each service. I had crossed the point of no return. I was finally disconnected from the social web.
Not surprisingly, the first few days were a challenge mentally. I had feelings of loneliness, boredom, mild depression and FOMO. A bunch of questions raced through my head. What are people talking about and sharing? What posts, articles and companies am I missing? Who is trying to get in touch with me? How am I going to be effective at work? It was evident that I had become heavily dependent upon social networks for information, interaction and self-validation. There was suddenly a big void in my daily routine. That first weekend, I felt disconnected from the rest of the world and had no clue what was going on outside of my little bubble. I was on an island. While my brain was craving that sweet burst of dopamine from online interactions, I continued to remind myself that these withdrawals would likely subside after the first week.
I even noticed some unexpected behaviors during the initial withdrawal phase. For example, I tried to rationalize why I should still be able to use certain apps like Strava to track my workouts. I also found myself reaching for my phone at least a dozen times daily to post an article, a picture or a specific thought. That behavior was clearly hardwired in me. I also began to notice that I stopped taking photos because I couldn’t share them. My news consumption also shifted. I began to rely upon traditional media sites and aggregators for such as The NY Times, Wall Street Journal, Nuzzel, Hacker News, Launch.co and Techmeme. Most surprisingly, I no longer wanted or felt the need to use my phone because I couldn’t engage online with my friends and followers. My iPhone quickly morphed from a personal device to a work device. The shift I experienced was fascinating.
A week into the experiment, my anxiety and old behaviors began to slowly fade. Even though I was disconnected, I was enjoying the reduced stress and clutter in my life. While I was still on edge, I didn’t mind the void because my world was noticeably slowing down. Additionally, I still had the urge to post and engage online but the cravings weren’t nearly as strong. My FOMO was still present because information is a currency in technology and venture capital, but I didn’t let it get the best of me. I began to rely upon more in person conversations and phone calls to stay on top of work and the venture market. During this period, I gained confidence that life without social media was possible and could be both enjoyable and productive.
When I reached the fifteen-day mark, I had noticed a profound change. I was much more present. My anxiety completely disappeared. I stopped thinking in tweets and visualizing photos to post. I had developed a fresher mind. I stopped comparing myself to others. I no longer felt the desire to reach for my phone throughout the day. In fact, my phone usage decreased by more than fifty percent. I went from taking a few dozen photos each day to none. The phone no longer was a crutch for my boredom. I was becoming more productive and focused with my time. During the second week, I also noticed that I was usually two to three days behind on big national headlines but didn’t seem to care. I was late to hear about movements such as Black Lives Matter and Pokemon Go. Frankly, the FOMO I had experienced only weeks ago was now virtually gone. I was embracing my transformation and enjoying my new mental state.
One morning in the third week of July, I had a major breakthrough. While meditating in Washington Square Park it suddenly occurred to me that I no longer needed others to validate my ideas, pictures, things I read because the validation was coming from within. In that moment, I felt completely free from my dependence upon social media to help me feel smart, witty, creative, etc. Additionally, all of the clutter, negative emotions and old behaviors no longer weighed me down. I had finally reached the outcome I was hoping to achieve when I decided to experience life without being tethered to social networks.
Studies suggest it takes twenty-eight days to start and break a habit. Based on my experience over the last month, I think there’s some validity to that claim. Even though I had undergone positive and unexpected changes throughout July, I missed engaging online with friends, sharing ideas and discovering new content. As the end of July approached, I was excited but a bit anxious jump back into products like Twitter and Instagram. I contemplated the following questions. What if I just remained disconnected? How do I introduce these apps back into my life? How do I use them in a healthy manner going forward? Should I use them at all? Can I control it?Despite some hesitation, I was ready to start over, give it a try and develop healthier habits.
On August 1st, I dipped my toe in the water and downloaded Twitter. I decided to start slowly and evaluate how I felt after a few days. As soon as I opened the app, the feed was both overwhelming and intoxicating. I was amazed by the speed of information (and reminded how many people hate Trump). I was bombarded with articles, ideas, quotes, images and infographics. Interestingly, I consumed more information within the first ten minutes than the previous few days. It was exhilarating. Three days later, I reinstalled Instagram and recalled how much I enjoy sharing photos and seeing other people share their lives. Twenty-four hours later, I posted my first photo of a sunset in Santa Monica. I felt connected to the world once again.
Since my social media detox ended, I’ve been trying to build good habits and moderate my usage but still find myself reverting to old behavior. I’ve avoided spending large chunks of my time within the apps but find myself checking Twitter during brief pauses throughout the day. I’ve also tried to set limits on how often I tweet or post a picture. Despite these protocols and the very best intentions, I caught myself falling back into old behaviors over the last few days. Not only was I taking more photos but I also found myself checking my phone when I was tired and bored. Just like the old days. Perhaps my social media detox didn’t change me as much as I thought it would. Perhaps I’m no longer enlightened. Perhaps I’m just a social animal and can’t resist connecting with others online.
Despite my rocky relationship social media, these products have brought me a tremendous amount of pleasure, entertainment and utility over the years. They’ve helped me forge new relationships and maintain old friendships. They’ve enabled me to be effective at work and access an endless amount of information. They’ve even helped me grow through self-expression and exploration. It’s hard to ignore the impact that it has had on my life and career. In closing, my social media detox has taught me a tremendous amount about myself and human behavior. The process has been a good reminder moderation is necessary for a happy life and behavior change isn’t always as easy as it seems.
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 her career in branding, Eliza noticed that plants were effectively a commodity and that no modern brand spoke to millennials who wanted more greenery in their lives. Despite plants being a multi-billion dollar category, virtually none of the options took a design oriented and customer centric approach. Sensing a gap in the market, she decided to quit her job at Living Proof, start The Sill, and raise some cash on Kickstarter.
Fast forward four years, The Sill now delivers plants to apartments all over Manhattan and Brooklyn, operates a retail shop in the Lower East Side, services large corporate accounts like WeWork and Google, and ships nationwide. While the company’s first office was a tiny, rent-free space in Chinatown, it’s now headquartered in a 10,000 square foot industrial facility in Maplewood, New Jersey. Magazines, blogs and other media outlets have taken notice. The Sill has been featured in just about every major publication including Dwell, Better Home & Gardens, Forbes, Vogue and Refinery29. Most importantly, Eliza has built and groomed a dedicated and passionate team who truly believes in building a category-defining company. They’re like a family.
All of this has been accomplished with blood, sweat, tears and lots of dirt under her fingernails. Literally. The Sill remains bootstrapped and 100% employee owned. In this day and age, when the default seems to be shacking up with cofounders and raising large seed rounds, Eliza decided to travel the path less taken. Single founder. No investors. She, her partner and team, have built The Sill brick by brick. Every dollar The Sill has made has been reinvested in the business so it can continue to grow and thrive.
As you can probably tell I’m super proud of Eliza and The Sill. And for good reason. I have a front row seat into the life of a female founder. Not the watered down stories we all read in blogs but the real stuff. I see the stratospheric highs and deep lows. I’ve see how hard she works. Seven days a week. Three hundred and sixty five days a year. I see how much she cares about delivering an amazing experience to all of her customers, especially when they are unsatisfied. It’s clear that building a successful brand takes an insane amount focus, passion and dedication. The customers always need to come first. There are no shortcuts or overnight successes. In fact, Eliza acknowledges The Sill will be at least a decade-long endeavor.
I witness it all. Running payroll late at night. Taking calls and sending emails at all hours – even while on our vacations. Balancing the books at month end. Being treated differently by suppliers and partners because she’s a woman. Waking up at the crack of dawn to receive a truckload of plants. Creating and sending proposals to clients. Working all weekend to help at the store or a photoshoot at the office. Having an employee quit a few days before a big project. Feeling like the task list is never ending. Dealing with employee matters such as hiring and firing. Losing key clients. Worrying about running out of cash. Crying at the end of the day because some times she feels alone and that it’s just really fucking difficult. There’s very little romance when it comes to being an entrepreneur. From my vantage point, it’s a gut wrenching roller coaster ride.
Many people assume that I advise The Sill given my day job and my relationships. Honestly, I stay out of Eliza’s way. I don’t review financial models. I don’t provide criticism when I disagree with a decision. I don’t dig into business processes. I even restrain myself from pointing out bugs on the website. I realized very early on that The Sill is Eliza’s company, not mine. My job as her husband and best friend is to be present, listen and provide emotional support. I only offer advice and feedback when asked for it. I don’t give her a hard time for working too much. Sure, there are times when I disagree. But I bite my tongue, because putting my ego aside and being there for her is more important for our relationship and the company.
Over the last four years, my advice to Eliza has stayed the same. I tell her to keep on doing what she’s doing. To show up every morning and never give up. To have faith that everything is going to work out. To build a sustainable business so she can control her own destiny. To intensely focus on delivering a great product, experience and brand that her customers love. To believe in herself and her team. To live in the future rather than the past. To move swift when something isn’t working. As I am writing this, I realize most (if not all) founders could benefit from these words of encouragement from those who are invested emotionally and financially.
What has all of this this taught me and how has it helped me become a better investor? This experience has given me an insane amount of empathy for founders and has humbled me in more ways than I can describe here. My biggest learning in all of this is the impact of listening and supporting over fixing and controlling. That’s what entrepreneurs need more than anything. While I’m fortunate to work with dozens of incredibly talented and creative founders at RRE, Eliza is by far the most important entrepreneur that I work with and learn from. Being married to a founder can be frustrating and challenging at times, but it’s also incredibly fulfilling and exciting. This experience has made me a better husband and investor many times over.
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 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.
A few days have passed since the retreat ended and I’m still processing the experience because I found it powerful both personally and professionally. I learned a tremendous amount about myself and the other participants. This was extremely useful for me because I’ve found that investors rarely open up to one another about work, life and everything in between. Throughout the weekend, I was able to recognize that many of the things that I wrestle with as a board member and an investor are quite common. Just as important, I gained more empathy for entrepreneurs and their daily struggles.
As I look back on the weekend, there are many teachings and lessons that I brought back to New York with me.
- When your inner and outer self aren’t in sync, it creates personal dissonance that results in being afraid, feeling unsafe, etc..
- If you ask a founder how you can help, it means you haven’t been listening close enough. Be fully present.
- Being a great board member or investor isn’t about having all the answers and fixing things. Don’t underestimate the power of listening and supporting.
- There’s tremendous power in the question, “How are you?” Show you care. Find out what’s really going on. Be human.
- Many people, including founders and investors, are dealing with things such as depression, anxiety, imposter syndrome, addiction, etc.. People in the startup community are human…not super human.
- Before making a significant decision, visualize the result and impact on your life. In other words, “try on” your decision each morning or night. Act it out. Write it down. Internalize it.
- The human soul is resilient and can recover from nearly anything including massive failures and personal adversity.
- We’re all learning on the job and no one has all the answers.
- Don’t rely too heavily on “playbooks.” You should always question them and / or throw them out the window.
- Having a beginner’s mind is a beautiful perspective because it enables continuous fresh thinking.
- Don’t hide from your shadow qualities. Instead, learn to shed light on and embrace them.
- Be mindful of the pronouns that you use (e.g. you, I, our, etc.) in discussions with founders and partners. There’s a big difference between “I’m sorry” and “How are you doing?”
- Sometimes it’s easy to blame changing industry dynamics, the macro environment, and other actors when things aren’t going well. When you find yourself doing this, take a look in the mirror.
- Journaling is a wonderful and powerful tool that can extract ideas and emotions.
- Finding work / life balance is critical to maintaining healthy relationships and overall wellbeing.
- Every firm is a direct extension of the partners and values. Seek to build a firm that you are proud of and would want to work for.
As you can probably see from these learnings, the bootcamp went deep and had a profound effect on me. I should note that I’m speaking on behalf of myself and not the entire group. These are my conclusions based on the experience that I had. I recognize that everyone sees the world in a unique lens and brings a different perspective to the table.
In closing, I’d like to extend a heartfelt thank you to Jerry, Brad and the rest of the participants for creating and embracing such an open and safe space. It was a truly magical weekend. I have no doubt that many of the participants will be co-investing together and positively impacting the startup community for many years to come. If you’re a founder looking for a mindful investor, I highly recommend you seek out any of the Reboot participants. They’re all special individuals who truly care about being great partners, building quality firms and impacting the world. In fact, I believe this crew represents the future of the venture industry because they’re guided by their values and their hearts.