On Privilege

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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 Investments, an investment platform that cares less about creating the next woman billionaire and instead backs businesses that create wealth for a billion women:

I immediately became defensive because I had good intentions in writing the post and felt I highlighted ‘universal’ attributes of great investors. Without giving it any thought, I quickly replied to Nathalie with the following tweet:

I then felt a backlash from a number of individuals including Katherine Gordon, Founder of The 3% Conference.

At that point, I became uncomfortable because my ignorance was obvious. Growing up in a predominately white upper middle class town in Massachusetts, I was indirectly taught that privilege was about wealth rather than race, gender, sexual preference, etc.. I incorrectly believed I wasn’t privileged because a) I was raised by an amazing single mother who worked two blue-collar jobs, b) I’ve earned an income since my early teens, c) I financed my college education, d) and I’ve worked hard to be self supporting for nearly two decades. It dawned on me through those various exchanges that I have been eating my own bullshit. What I began to quickly realize is that wealth is just one component of privilege and arguably the weakest one.

Later that night, I was talking with my wife, who happens to be Asian American (and more self-aware of her life’s privileges), about the exchange on Twitter. Eliza immediately called me out for lacking empathy and explained that I was wrong on many levels. She pointed out that I’m oblivious because I don’t even see how my own privilege as a white man in America has contributed to my success. Eliza asked me how many opportunities in life I’ve received because I look and talk like those who made the decisions. I didn’t respond to her because I knew the answer. This was difficult to hear and accept because she was right and there was no logical argument that I could make.

Several days later, Nathalie’s tweet and my conversation with Eliza were still weighing on me. I’ve since learned that the idea of privilege dates back to the early 1900s. Famed American civil rights activist W. E. B. Du Bois wrote that although African Americans were conscious of racial discrimination, white Americans did not think much about the effects of racial discrimination. The concept didn’t really enter the mainstream until 1988 when activist Peggy McIntosh published her seminal article, ‘White Privilege and Male Privilege: A Personal Account of Coming to See Correspondences Through Work in Women’s Studies.’ McIntosh describes her understanding of “white privilege” (unearned advantage based on race) which can be observed systemically and individually, like all unearned privileges in society (e.g. privilege related to class, religion, ethnicity, sexual orientation, age, ability).

One year later she published a shorter version titled, ‘White Privilege: Unpacking the Invisible Knapsack.’ These words in particular struck a chord: “After I realized the extent to which men work from a base of unacknowledged privilege, I understood that much of their oppressiveness was unconscious.” In this particular essay, McIntosh outlines twenty-six privileges which she, as a white person, experienced in the United States. Many of them are powerful examples but this one stood out: “If I want to, I can be pretty sure of finding a publisher for this piece on white privilege.” After reading her piece and starting to educate myself, it was impossible to refute that being born white and male and American (the birth luck trifecta!) provides me certain unearned privileges in life that people of other gender and skin colors simply are not afforded.

After I read these essays, I began to contemplate the privileges I experience on a regular basis. Like Peggy McIntosh, I composed a list of these to shed light on what I take for granted. The list included everything from ‘I don’t often think about the personal safety of myself or my loved ones.’ and ‘I don’t have to think twice when asked a question by the police.’ to ‘I don’t have to worry about finding work that is both fulfilling and financially rewarding.’ While I still have much more to contemplate, this exercise has also put things into perspective.

What I’ve also come to understand is these dynamics run DEEP. Really deep. So deep they’ve been systematically engrained into our way of living over hundreds of years. So deep they’re unconsciously programmed into our brains. So deep they perpetuate capitalism, globalization and power. So deep they transcend race, gender religion and national boundaries. In fact, so deep that I’ll likely never understand them regardless how much empathy I develop, how many conversations I have and books I read. These dynamics are extremely powerful, complex and twisted.

Warren Buffett famously said, “I won the ovarian lottery.” So did I. I don’t want this to make me a bad person and I don’t want to feel ashamed. I also don’t want to discount the thousands of hours of hard work I’ve put in over the years. Like others, I don’t know what to feel sometimes. This is very complicated. What I know is this: I have a good heart, an open mind and a desire to expand my worldview. Thankfully, this experience has been humbling and enlightening. I have no doubt it’ll have a lasting impact on me.

In all honesty, I’m still processing all of this and I don’t truly know what I’m talking about yet. I understand this is an awkward conversation and I’m willing to risk saying things incorrectly so I can learn to say them right. I’m certainly open to feedback and criticism. This certainly doesn’t make me special or a hero. I don’t expect a pat on the back. I’m writing this because I believe I need to speak up about this topic and express how I feel. Raising my daily consciousness about the realities of privilege and acknowledging that it’s not an even playing field is an important first step for me.

Finally, I’d like to apologize to Nathalie, Katherine and others for getting defensive about their tweets rather than initially taking a step back and considering their perspective. I’m grateful that these women and my wife forced me to look in the mirror and think about such an crucial topic that’s often swept aside out of habit, ignorance, fear and/or hatred. Thank you for speaking up and challenging me. We need more of this. Not less. I’ll end with this:

“Our lives begin to end the day we become silent about things that matter.” Dr. Martin Luther King Jr.

Decoding the Qualities of a Great VC

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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 were essentially out of time, I told him that I’d give the question more thought and I’d email him my thoughts over the weekend.

Later in the day when I had some downtime, I began to consider Parker’s question and asked myself the following related questions: What makes a good VC? What’s important to venture firms, limited partners and founders? Who are the best VCs and what makes them special? After considering those questions, I grabbed my notebook and wrote down the attributes that I felt were essential.

  • Curiosity — thirst for knowledge and learning.
  • Expertise — business, engineering and/or product chops developed through experience.
  • Passion — genuinely excited by new ideas, innovation and entrepreneurship.
  • Focus — ability to drown out noise and spend time on what matters.
  • Network — authentically develop and maintain relationships at scale.
  • Sales — ability to sell and build consensus internally and externally.
  • Emotional intelligence — empathize and assess motivations, desires, needs and intangibles.
  • Conviction — ability to maintain excitement in the face of opposition and skepticism.

Rather than sending Parker an email with my thoughts, I decided to share the list on Twitter, cc him on the post and participate in the conversation that unfolded. Several founders and investors chimed in publicly and privately to share their views and expand the list I started. While I don’t necessarily agree with all of the suggestions, the other attributes that were mentioned included:

  • Quick learner — ability to quickly consume, learn and absorb information about a wide variety of topics.
  • Friendly — generally pleasant to be around and likable (while I try to respect everyone, I’m not sure this is a prerequisite for being a great investor).
  • 1st principle thinker — someone who can boil complex ideas and phenomena down to their fundamental truths.
  • Stoic — remain calm under pressure and turbulence.
  • Humble — modest in behavior, attitude or spirit.
  • Vision — can see where the world is heading.

This combined list of fourteen attributes is far from comprehensive but I believe it captures many of the important ones. I wonder how the world’s best VCs — investors like Michael Moritz, John Doerr, Marc Andreesen, Shana Fisher, Fred Wilson, Bill Gurley and Chris Sacca — would describe themselves and their most successful peers. I also wonder if their institutions have developed a system to identify the next great generation of investors based on a set of attributes and experiences. Their firms have managed to stay on top for multiple cycles and I don’t think it’s by accident. Given people and networks are at the center of the VC business, perhaps they’ve discovered the hidden answer to the talent equation through identifying, hiring, training and retaining remarkable people.

Several years ago, Jerry Neumann, a respected angel investor in NYC, catalogued the background of every great VC firm’s founders, trying to answer this question. Here is the output from that effort which he titled, VC Genealogy. According to Jerry, the most interesting thing he found is that aside from the expected bankers and lawyers and tech-company execs, there were some journalists in there (Moritz being the most prominent). The qualities of journalists stood out to him because they’re able to track down the right people to interview, ask the right questions, validate the answers they receive and communicate their findings succinctly. Clearly being an effective communicator is critical.

That brings me to the million dollar question: Is it possible to create a platform or system to identify and train the next crop of top venture investors in the world? What would it look like? Perhaps the system is driven by software. Or perhaps it’s a new type of organization in the vein of YC that identifies, trains and networks investors. Maybe it’s a hybrid. I could imagine such a system would score, weigh and rank the candidates based on criteria, attributes and experiences. How would such a program or system grade intangibles or soft skills? Could it identify the power of someone’s network? What are the potential inputs of such a system and what could the output look like? The questions are seemingly endless but it’s a fun thought exercise worth considering.

Maybe this is a pipe dream given there are so few truly great investors and VC is considered to be an apprenticeship business where the learnings take place over many years and throughout cycles. VCs face so many different problems over their careers or even over the course of a portfolio company’s path — that even the best suited have to do a few years of on-the-job learning to be great. Would Fred Wilson be the same investor if he hadn’t experienced the dot com boom and crash at Flatiron Partners? Did Bill Gurley receive years of unique mentorship from the founding partners of Benchmark? What were the key insights Shana Fisher developed while at IAC? Did Michael Moritz discover the ideal founder archetype by writing about Steve Jobs and Lee Iacocca or did he learn from Don Valentine and his predecessors at Sequoia Capital? How did those experiences and interactions shape their investment tastes and philosophies? Given experiences play such an important role in shaping an investor, I’m honestly not sure if it’s even possible to develop a system that delivers alpha by finding and training future investors unless it’s a longer term endeavor.

All that said, experimentation and time will tell us if this is possible. I have a hunch we’ll witness the emergence of a ‘YC for investors’ in the next few years. While venture investors don’t match the speed of innovation as our founder peers, VCs have attempted to create new models and programs over the last few decades. For example, DFJ franchised (brand), 500 franchised (brand), 500 has a VC class (edu), Kauffman Fellows (edu), AngelList syndicates (tech, network), and scouts (network). We’ve seen tech, network, education, and brand as things that people have tried in various combinations to make new VCs. The obvious other options being “hire and train” and “learn on my own dime.” I suspect there’s more to come which is always a good thing.

In closing, I hope any new innovations will be intelligent enough to find the next great VCs based solely on proven attributes and experiences. I also hope these efforts will expand the pool of candidates (think: gender, race, geography). Given the ceiling to break into VC is extraordinarily high — capital, networks, experience, geography — I believe expanding the talent pool would be a good thing for funds and limited partners. That could very well be one of the lasting benefits and contributions these innovations bring to the industry. It’s my hope that in twenty years the list of the great venture capitalists is a diverse set of humans with strong attributes and abilities that have been validated by the giants who helped build the industry.

If you have some thoughts on what makes a great VC and would like to contribute to the discussion, please hop into our thread on Twitter. I’d love to hear from you.

(thanks to Parker Thompson, Jerry Neumann and Leo Polovets for reading an early version of this post) 

10 Days of Silence for a Lifetime of Wisdom

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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 became an influential teacher and established meditation centers, like the one I attended in the Berkshires, all over the world.

S. N. Goenka

My time at Dhamma Dara was easily one of the most brutal and intense yet profound and rewarding experiences in my life. When I signed up, I didn’t expect the retreat would help me solve my problems or discover my purpose in life. My goal going into the course was simply to gain a greater appreciation and understanding of my mind. However, I walked away experiencing and learning so much more. I didn’t fully appreciate how intertwined our minds, emotions and bodies truly are.

So what exactly is Vipassana? The Vipassana philosophy is built around a technique of meditation focusing on the breath and self observation of the sensations on the body. It’s a method of ‘mental purification’ which allows one to face life’s tensions and problems in a calm, balanced way. Vipassana aims to eliminate the three causes of all unhappiness: craving, aversion and ignorance. With continued practice, the meditation releases the tensions developed in everyday life, dissolving the knots formed by our habit of reacting in an unbalanced way to pleasant and unpleasant situations. Although Vipassana was developed as a technique by the Buddha, its practice is not limited to Buddhists. In order to penetrate the deepest levels of the unconscious mind and heal our complexes, students are expected to work diligently and observe the code of discipline prescribed by Goenka.

During the ten days, we were stripped of all conveniences and comforts. We also had to abstain from any unwholesome behaviors. Before the course, all students agreed to abstain from killing, stealing, engaging in sexual activity, telling lies, consuming intoxicants, eating after noon, engaging in sensual entertainment, wearing revealing or fancy clothing, and sleeping on luxurious beds. Additionally, we agreed to practice the technique taught by Goenka, observe noble silence (read: no verbal or non-verbal communication), adhere to separation of genders, and limit physical exercise to walking. Finally, we had to turn in our devices, books and journals before the course kicked off. Simply put: all distractions were removed. The purpose of the code of discipline isn’t to punish but rather to create the optimal environment and frame of mind for meditation. I was excited to unplug but also a bit anxious.

For ten days, we followed a super rigid and strict schedule.

Source: Sophia Ciocca

That was our routine each day with few variations. We practiced nearly a hundred hours of meditation while on retreat. During our limited breaks, we were able to eat (breakfast and lunch), walk the grounds, wash up, think or rest. That’s really all we could do when we had downtime. The only other ‘escape’ was an evening video discourse from Goenka. During these hour-long lectures, Goenka shared the philosophy behind Vipassana, previewed what’s to come the next day and provided actionable insight about the practice. As you can probably tell from the schedule and the code of discipline, there wasn’t much about this ‘retreat’ that was relaxing or fun.

For the first three and a half days, we engaged in ‘Anapana’ meditation. Anapana means ‘mindfulness of breathing.’ The technique is simple but challenging: concentrate on nothing but inhales and exhales. When the mind wanders simply return to the breath. This form of meditation sharpens the mind and develops the concentration required for Vipassana. The first three days were physically brutal. My knees, hips, back and neck were sore from sitting on a cushion with no back support. But by the end of the third day, my mind was beginning to quiet and I was experiencing extremely subtle and gross sensations inside and around my nose and upper lip. Sensations such as heat, cold, itching, tingling, pain, blockage, throbbing, hardness and softness. Once I could feel that my mind was sharpening and sense subtle sensations, I knew we were ready to begin practicing Vipassana.

Vipassana means ‘insight’ or ‘clear seeing.’ On the forth day, we were instructed to expand our awareness from the nose to the entire body by using a body scanning technique that stresses developing a heightened sensitivity to a variety of gross and subtle sensations such as the ones I mentioned above. The technique prescribes starting at the top of the head and scanning every body part down to the toes. Once we reached the tips of the toes, we calmly scanned the entire body back to the top of the head. Over and over and over for six days.

As sensations surfaced, pleasant or unpleasant, we were instructed to note them and remain equanimous (not good, not bad, it is what it is). Throughout the retreat, Goenka reminded us not to judge, oppose or cling to any of the sensations. By removing emotions and feelings from bodily sensations, the ego begins to dissolve and we begin to remove the underlying causes of craving and aversion.

By day six, I had reached an altered state of consciousness unlike anything I’ve ever experienced outside of limited experimentation with hallucinogens in college. I became so in tune with my body and mind that I could feel both pleasant and unpleasant sensations from my head to toes and even deep inside my body. Some pains and cramps were so intense that I had to learn how to develop equanimity which wasn’t in my vocabulary before the retreat. I completely underestimated the power and physical intensity of the Vipassana technique.

By the seventh day, I was telling myself that I wish I had ‘read the label’ and done more homework about the technique and its effects. I was obviously past the point of no return but was overwhelmed by the intensity of the sensations. I even went to the teacher at one point and asked him how I could ‘turn down the heat.’ Throughout the last few days, I experienced chest and abdomen pain that I used to suffer from many years ago. I was clearly deep into my subconscious and the meditation caused it to resurface. The practiced forced me to deal with the root causes of the issue — mainly stress and anxiety related to childhood and adolescence.

By the end of the retreat, I was able to sit with these painful sensations, observe them and literally feel them dissolve inside of me. I was also able to sit for hours without moving or feeling much structural pain. The mind body connection is incredible. I was healing myself by focusing on and accepting these physical pains that I’ve been afraid of for more than a decade. Instead of running, I had no choice but to surrender and in many ways kill my ego. In retrospect, that was the obvious solution but it took me ten days to figure it out for myself. In some ways, I felt like performed surgery on my mind and body. It was a surreal and deeply moving experience. Thankfully, I was able to face some deeply rooted and underlying issues that had been bothering me for nearly two decades.

About midway through the tenth day, noble silence was lifted and we were able to communicate with the other students. This helped ease us back into reality. I found it really valuable because I was able to hear about other’s experiences and begin to process my own. One conversation in particular was very helpful. I had told one of the participants that I was ‘penetrating and attacking my pain’ over the last few days in an attempt to fix myself. She got emotional and tears welled in her eyes. She responded, “Don’t say that. You should never attack yourself. You’re healing yourself through self care.’ That one comment was incredibly helpful and really helped put the entire experience in perspective. I dedicated the remainder of the last day and my final meditations to self love and self care. That’s the piece of the puzzle that I was missing. At that point, I knew that I received what I came for. I was ready to go home.

Despite being home for three weeks, I’m still processing my time at Dharma Dhara. I expect that it will take a few months to fully appreciate and internalize what I learned about my mind, body, spirit and ego. Maintaining an hour of meditation each day is certainly helping me go deeper and unlock a sense of awareness I never thought was possible. As I anticipated when I signed up for the course, my problems haven’t disappeared and I didn’t find my purpose in life. But I’ve emerged stronger, calmer, more patient and more resilient. I also feel way more present so I can be in service of and available for others. Best of all, I now believe I can tackle any challenge and find equanimity in good situations and bad. While I’m just starting on the path, I’m enjoying the moment and the process.

In Closing: Lessons & Learnings

When I returned home, I wrote for a few hours to capture the essence of my experience at Dhamma Dhara. I noted everything from the food to all the business ideas I dreamed up. One of the sections was ‘Lessons and Learnings.’ I’ll leave you with what I jotted down that afternoon. If any of these ideas or my experience resonates with you, I’d be honored to hear from you. Without further ado:

The 10 days were the equivalent of 10 years of life lessons and therapy.

Everything rises and passes. It’s a law of nature. Change is constant around us and within us.

Craving, aversion and ignorance are the roots of all issues and lead to suffering.

The world doesn’t stop for you when you’re away or offline. It just keeps moving.

The mind, emotion body connection is more accessible and far deeper than you believe.

Changes often provide temporary relief but pain and suffering always returns.

The mind wants to take us into the past or the future with pleasant or unpleasant thoughts. Remaining in the present is reality so embrace it.

Don’t trust all of your feelings and snap judgements towards people. We’re very good at crafting stories and beliefs in our minds with very little context.

Nothing is more sacred and precious than family and friends.

Developing a sincere desire for all beings to be happy is incredibly powerful and liberating.

We can survive on far less comfort and food than we’re used to.

Consume enough to sustain but not more.

Limit waste and embrace conservation.

Don’t force things. Apply the right amount of effort but not too much.

Take and consume only what you truly need. Not more.

Humans are far more resilient and adaptive than we believe.

We can heal ourselves mentally and physically using mindfulness and meditation. It just takes commitment and an investment of time and energy.

You can learn the basics of anything if you dedicate 100 hours over a few weeks. Immersion and focus generate results.

Find appreciation in the mundane.

These four words repeated over and over can get you through anything: patience, persistence, awareness, equanimity.

Most pain is a function of the mind and created by feelings such as anxiety and fear.

Sitting with both physical and mental pain for long periods of time is strangely liberating and builds resiliency.

Our bodies adapt to changing stimulus far more quickly than most believe.

Our capacity to deal with emotional and physical pain is far greater than we believe.

The only person you can change is yourself. When others notice your changes, it might give them the courage or the reason to change themselves.

Perception is powerful .You often see only what you want to believe.

Pause before speaking or acting. Sometimes you’ll change your approach with just a bit of time and reflection.

The more emotional and physical pain that is suppressed, the deeper it’s driven into our subconscious and bodies.

Be mindful anytime you use the words me, mine, my, I. They signal attachment.

We are a collection of dualities (love vs hate, joy vs pain, happy vs sad, comfortable and uncomfortable, etc.)

Love yourself. Focus on self care.

The subconscious is very accessible.

Expectations set us up for clinging and disappointment.

Equanimity isn’t suppression of thoughts or feelings but being ok with how a situation unfolds or how we feel in a given moment.

Spending time alone is very underrated.

Creating time and space to process is essential for the spirit.

Be kind to others. Goodness is contagious. Life is too short to be mean.

/Fin

Hug O’ War

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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: 

hug-o-war-shelsliverstien

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 with more kindness. I can’t think of a better purpose than that.

hugs

Introducing Huddle: Peer-to-Peer Support Groups for the Masses

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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.

Embracing Radical Candor to Overcome Your Worst Habits at Work

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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?

Venture Investments Are Not Bets

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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)