Schlaf.me

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 was flipping through the book, I arrived at one of my favorite poems, Hug O’ War: 

I immediately Google’d Hug O’ War to learn more about what inspired Shel to write the poem. I discovered that he wrote it to widely express nonviolence and goodness to the world.  That expression really resonated with me. As I reflected on the poem, the words non-violence, cooperation, winning, surrender, love, happiness and goodness kept coming up for me. I felt those words accurately represent what I value as a human being.

Yesterday, I walked into a tattoo parlor near Chinatown in San Francisco and had Shel’s Hug O’ War illustration etched on the back my arm. My hope is that it’ll serve as a reminder to always love, support, serve and cooperate rather than to fight, harm or hurt. Here’s to filling the world more goodness! I can’t think of a better purpose than that.

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.

That’s why I was excited to meet Tyler Faux and Dan Blackman of Huddle. They shared their plans to build a video-based peer-to-peer support network and change how the world communicates about mental health issues. They explained their product would have public and private channels for people to engage about the things in life they are dealing with. They also explained, that Huddle will allow people to be anonymous or themselves so they can engage however they’re most comfortable. In that moment, I wished I had access to this product many years ago when I struggling but wanted help. I was also captivated by their mission of breaking down conventional perspectives of how people are supposed to get help by creating a community of real people, talking about real things, supporting one another.

As they were describing their product and vision, I believed millions of people would potentially see the value in a digital peer-to-peer support network. Support groups are incredibly effective but haven’t evolved in decades. There are more than 500,000 offline support groups in the U.S. alone. At any given time, more than 6.5 million Americans engage in these groups. They have numerous benefits including accountability, perspective, community, emotional support, service, mentorship and empowerment. Despite these benefits, support groups today tend to be antiquated, fragmented, geographically limited, infrequent, offline, stigmatized and difficult to discover. That’s why I felt there was a real need to modernize these therapeutic communities.

Support groups exist for good reason. 44 million Americans struggled with mental illness in 2016 but more than 60% didn’t seek treatment. That doesn’t even include those who are impacted such as family, friends and co-workers. People seek help for many life situations such as addiction, depression, death, illness, PTSD, body image, eating disorders, obesity, divorce and many more. The more I thought about the problem and the need, Huddle seemed to be a potentially appealing solution that could transcend race, religion, ethnicity, socioeconomic status and boarders.

And let’s be honest: traditional social media isn’t helping this problem. In fact, one could make the argument that networks like Facebook are only making the problem worse despite their best efforts. Additionally, most people aren’t comfortable broadcasting their problems to family, friends and co-workers due to stigma, fear of being judged and potential negative consequences both personally and professionally. One could also make the argument, that people aren’t comfortable seeing other’s struggles in their social feeds. A void seems to exist in the world.

That’s why I’m thrilled to share that Huddle is now a reality. I’m also thrilled to share that I’ll be playing a small role in the company as an advisor. As you can probably tell, mental health is an incredibly important cause for me and I believe that digital tools like Huddle can be a significant part of the solution. The app launches today so anyone with an iPhone can join the community, get strength from others or lend your support to those in need. You can download it here. While the community is just getting started, I believe digital peer-to-peer support groups will be the norm in the next decade.

Life is hard, messy and unpredictable. Every single one of us or people that we love are struggling with something whether it’s depression, divorce, anxiety, addiction, fear, anger, resentment and / or imposter syndrome. Instead of grandstanding on social media (of which I’m guilty of myself), why not embrace our imperfections? Why not start an internal or external dialogue about what’s really going on in our lives. The impact would be massive. Here’s a big secret: when you speak openly about your challenges it gives others the strength to do the same. I realize it’s frightening but the rewards are boundless. We can start to relate to one another. We can support each other. We can heal each other. That to me is way more powerful and beautiful than pretending everything is perfect.

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 has developed over his 40+ year career. Some would suggest his approach and views of the world are radical but it’s hard to argue with Bridgewater’s success. Ray is a big proponent of radical transparency in order to arrive at the truth. His principles include embracing failure, being in synch, building teams carefully, and running an organization like a machine. While I don’t share all of Ray’s views, I do believe that just about every organization imaginable would dramatically improve if they read and adopted even half of the principles.

After I finished reading the document, I began to reflect on my own values and principles. I also began to question my own effectiveness as an investor and as an employee in the spirit of radical candor. What am I good at? What drives me? What are my blind spots? What are my bad habits? Where am I falling short? What am I currently struggling with? By asking myself these questions and investing the time to reflect, I was able to shed light on some of the areas at work that I should focus on. This process was both cathartic and enlightening. What I found was surprising and incredibly transformative but it required a structured process and heavy doses of reflection and self inquiry.

Several weeks ago, I developed a process to identify my poor work habits, understand the underlying causes and then create a plan to redesign how I respond to situations, make decisions and spend my time. The spirit of this exercise was simple: to drive more productivity, to try to understand myself better and ultimately gain a greater peace of mind. Here are the steps I took to change some of my least productive and most limiting behaviors on the job:

1. Identify the fears that impact my work
2. Note my big struggles and then tie them back to my fears
3. List all my bad habits that contribute to my struggles and feed my fears
4. Brainstorm practical solutions to ‘cure’ each bad habit
5. Ranked the list of cures based on priority, impact and pain
6. Implement a plan to fix three to five of my worst habits
7. Measure my progress monthly and reevaluate the list

Keep in mind this is not a once size fits all approach and it’s certainly not scientifically proven. I simply developed a process that I believed would work for me. It’s important to note that a) I devoted at least an hour to each step, b) I removed all distractions during each session such as shutting off my phone, and c) I sequestered myself at the library so I could intensely reflect and focus without any interruptions at home and work. I found journaling for steps 1–4 helped me let down my guard and channel inner candor and creativity.

I’m amazed how much I learned about myself in these short sessions over the last few weeks. I essentially put a magnifying glass on my fears, struggles and worst habits that have been causing mental friction and seriously limiting my productivity. The process so far has been both illuminating and liberating. Here is a peek into my exploration and some of the things I discovered.

Fears: After two hours of reflection and brainstorming, I generated a list of six primary fears that effect me at work and force me to react. It turns out that I have a fear of people not liking me so at times I try to please people even when it’s not in my best interest or what I feel like doing. Like many other investors, I also suffer from FOMO (fear of missing out) in certain situations. I’m also petrified of failing and not delivering results which is why I tend to overwork. These are just some of my fears but it should give you a sense of how honest I was throughout the process.

Struggles: Once I listed my fears, I was able to reflect on the high-level problems that I cause for myself. These are the areas where I feel the most pain or a drain on my productivity. At the end of the exercise, I identified six big struggles which include saying yes too much, being a slave to my calendar and email, and not maximizing every minute. This exercise set the stage for me to identify the underlying habits that were causing these overarching problems.

Bad Habits: I carved out three hours during a long trip to brainstorm which habits have been holding me back. I identified these habits by reflecting on my struggles and asking myself the following questions. Where do you feel the most pain on a daily basis? Which problems are self inflicted but within your control? What activities are limiting your work quality and output? The list was fairly comprehensive. By the time I finished, I identified and categorized thirty five habits. Each of these ultimately tied back to my struggles and then to my fears. One worth noting is daily breakfast meetings rather than going to the office early. These breakfasts can be a huge drain and distraction because I often won’t accomplish much until the late morning. Another negative habit I’ve developed is reacting to email based LIFO (last in first out) rather than prioritizing based on sensitivity. Many of the these limiting behaviors centered around communication, time management, goal setting and prioritization.

Cures: Once I identified the roadblocks to productivity and peace of mind, I generated at least two cures for each habit. For breakfast meetings, I have decided to avoid them at all costs with very rare exceptions. For reacting to email, I created a detailed prioritization system. For example, I now to respond to portfolio companies, any fire drills or my partners before anything else. By cataloging practical and immediately actionable remedies, I’m able to attack my deep rooted fears while also changing how I approach work. This section alone could be a separate blog post.

Implementation: Here’s where the rubber meets the road and the real change happens. I took the list of my habits and fixes, and then ranked each of them based on priority, pain and impact. Remember, my criteria will likely different than yours so I’d encourage you to focus on what you’d like to optimize and change. Once I developed my ranking, I immediately focused on the top five most limiting habits. My is goal to attack five over the course of a month and then move down the list every thirty days. If I’m able to overcome even half of the list then I’ll dramatically improve my output and mental state.

Re-evaluate: The final step will be to measure my progress on a weekly and monthly basis. I’m not quite there yet since I’m only a few weeks into the exercise, but I’ve taken some steps to ensure I stay focused. For example, I’ve blocked out 15-30 min each Friday to assess my progress and to review the list of cures so they remain fresh in my mind. I’m still working on the first batch so time will tell how much progress I’m able to make before the end of the year.

As you can probably tell, this exploration requires a significant time commitment, ruthless honesty and a strong desire to improve. I also found it requires a healthy dose of humility and maturity. But so far the process and the results have been well worth the time and emotional investment. While I’m not even a month into this experiment, I’m already seeing huge results and developing a better understanding of who I am. Looking in the mirror and acknowledging my flaws certainly hasn’t been easy, but I’d much rather shine light on them so I can grow and improve as an investor, partner and husband. To me, that’s much more exciting than pretending I’m flawless.

How do you change your worst habits at work?

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.

Regarding an investment as a bet certainly makes sense on the surface. According to Merriam-Webster, a bet is, “something that is laid, staked, or pledged typically between two parties on the outcome of a contest or a contingent issue.” The more I thought about labeling venture investments this way, the more I began to realize it was a bit lazy, potentially insensitive and didn’t necessarily align with my values. Simply put, this label didn’t feel right to me.

In my role as a venture investor, I don’t make bets. Bets tend to be passive unless you’re playing the hand. When I put a friendly wager on a game such as the Super Bowl, my involvement has zero bearing on the outcome. My job as a venture investor is to actively partner with and serve founders. There is nothing passive about this. Professional venture investing shouldn’t be confused with gambling even though a lot luck and a little bit of skill are required for success. Essentially, betting implies gambling and investing implies taking calculated risks.

After a founder has trusted me to serve his or her company and the investment closes, I do not passively wait for and expect a positive outcome. This is when the real work begins. Every company regardless of the stage requires a shit ton of patience, support and effort by everyone around the table. I felt characterizing an investment as a bet mentally excused me, the investor, from the real work ahead.

Here’s what I’d like to know from the venture community: What do you mean when you call it a bet? Are you impatiently waiting on the sidelines to see if you beat the odds? Or have you simply adopted the vernacular since many of our peers have? That’s where I found myself earlier in my career.

We, myself included, should never view our work as gambling given how much time, effort and energy goes into building companies and long-lasting relationships with founders. Instead, we should characterize our work as investing, partnering, supporting and serving. Founders put everything they have on the line — years of their life, physical and mental health, financial security, and family and friends— to bring their vision to reality. These are enormous and important sacrifices which is why I believe referring to an investment as a bet doesn’t reflect what we do.

(A special thanks to Alice Lloyd George and Jerry Neumann for reading an early draft)

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.

Connected Devices

• 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.

Physical Products

• 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.

Entertainment

• 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.

Newsletters

• 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.

Podcasts

• 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.

Books

• 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.

Food

• 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