S.T.O.P. – a poem from the prison yard

As you know, Crystal and I put a lot of effort into helping reform the racist and wasteful criminal justice system. This work ranges up and down the stack from helping people navigate the court system, gain access to early legal support, providing bail for those who don’t have it, funding lawsuits to eliminate cash bail systems that punish people for being poor, advancing legislative efforts to rationalize sentencing, and much more. But some of our most rewarding work comes from our time spent inside both juvenile and adult maximum security prisons in partnership with the Anti-Recidivism Coalition.

Within those walls, we encounter some of the most stunning examples of redemption and personal growth. The emotions can be confusing as you balance intense empathy and admiration for someone who is describing violent, even murderous crimes in their past. In the words of Bryan Stevenson, we believe that “We are all better than the worst thing we’ve ever done.” Being inside a prison puts those words to the test, and never more than during therapy and restorative justice programs, where offenders meet with their victims and/or their families and work through unresolved emotions. “Hurt people hurt,” as the saying goes. Restorative justice initiatives can break the cycle. They give the incarcerated the chance to heal themselves and turn their lives toward positive outcomes. Add job training to that, and we’ve seen remarkable results with recidivism rates of almost zero following release.

Through this work, we’ve made some good friends and been exposed to some downright inspiring characters. One of those is the poet Samuel Nathaniel Brown. He has recited verses that I find to be some of the most thought-provoking poetry I’ve encountered. Guys inside don’t usually have any access to computers, and as a result  their work often never leaves those walls. What a shame it would be in this era of mass communication that you would have to be standing in a prison yard to hear his wisdom. So, I asked my friend Sam if I could share one of his pieces with you here.

While you read this, please imagine the poet standing on a box and screaming “STOP” so loudly and gutterally that activity on the dusty prison yard ceases and everyone, inmates and guards alike, turn their attention to listen. Nothing can stop time and bring us together like words done right.


By Samuel Nathaniel Brown

Bloods and Crips, Starz and Zillas, Sureños and Norteños, Vicelords and Gangster Disciples, Democrats and Republicans – STOP.

Atheists and Believers, Muslims and Christians, Proletariat and Bourgeoisie, I’m above you and your beneath me – STOP. 

Native, Immigrant, Lover, Fighter, men and women, rich, poor, sinner and savior, hated and hater…

Palestinians, Jews, clicks, klans, crews, Boko Haram, Isis, Taliban, Hamas, Hezbollah, and the United States with your White Supremacy military coups…STOP, STOP, STOP!!!
With the hating, the arguing, the backbiting, the slandering, the posturing, the fighting, the murdering, the massacring. 

It’s time now, now is the time to heal from a place of realness – STOP  – racing towards our collective demise and practice stillness. 

For there is a light that shines for you and me, that is something we all have in common so let’s just be

A lot more cognizant of the fact that we are all we got and if we got and if we don’t watch each other’s backs

Then we’re gonna watch each other get buried…by the droves

Moment of silence for all the Lost Souls________

That died behind jealousy, racism, policy brutality, religion, oppression, gender discrimination, drug wars, and the color of their clothes
Or natural resources, ‘cause (geopolitical) powers commit genocide behind natural resources too, and if you thought that war was really about what they said it was really about, then I really doubt that you ever really had a clue – STOP!
…Letting people stick their fingers in your skull to reach inside your brain to seize hold of your mind, and mold your thoughts: Bring to remembrance the pure of heart, summon the spirits of the fighters that fought

In order to evolve us as a species to a higher level of consciousness…
In my own game of life I will not be a bystander, meaning I will not stand by: as another child loses their innocence, a woman is violated, or another unarmed man dies

That’s why, I stand by Black Lives Matter, cause we do, I stand by #metoo, I stand by the Fair Chance Project, The Family Project, The NAACP, ARC, the Poor People’s Campaign, Code Pink, and the ACLU, and if you are an individual or an organization dedicated to effectuating positive social change, then I stand by you too

I stand by the asylum – seeking, oppressive country defectors, by the god women and men in law enforcement that protect us, the firefighters, the freedom fighters, the school teachers, the Imams and Preachers that try to reach us through spiritual verses, our beloved nurses, and the water protectors.
With them I S-T-A-N-D. We strive together against negative development because we all agree. That is, we advocate gender racial and economic equality

Y’all can say I’m a man of many acronyms, synonyms, and spirituals hymns, I just know that when their cold minds apply pressure, they produce a lotta gems

And we are them

With our Golden Hearts, Silver Tongues, and eyes of Onyx, from English Speakers as a second language hooked on phonics, to those relegated to broken English and evolutionary Ebonics

When I say stop, it’s not stop as in sit on your hind quarters and accept the status quo, but rather, come together as a people to see how much mo’ we can grow

and further we can go…
An Ancient African Proverb says “If you want to go fast – go alone, but if you want to go far…go together”

Putin, Assad, Trump, Netenyahu, Kim Jong-un, will y’all just chill? If a mill got peeled in the battlefield would you then feel the need to be still or would y’all still just kill?

I mean on – the – real

What is it that y’all cherish? Is it the long-term existence of us as a species or are you too selfish and fulla pride to see the greatness that resides inside of being selfless?
Well, as long as their greed persists, we resist , and we insist, they cease and desist with their cataclysmic, catastrophic, characteristics centered at the core of the problems that plague us all – come on now – let’s read the list…

Mass school shootings, ocean polluting, reef killing, ozone layer destroying, genetically modified organism producing, cancer causing, terminal illness perpetuating, prejudicial, stereotypical mischaracterization of strangers from target groups from which you don’t know a soul, but’chu claim that you hate’m and despise’m and detest’em because the negative attitudes and beliefs that you inherit as a youth now that you are an adult you haven’t taken the time to reassess ’em…………STOP!

Big Oil, Big Tobacco, Big Alcohol, and all the rest of y’all…

Drug dealing, coffin filling, orphan making, profit raking, Uniform Commercial Code spawns-of-Satan, mega-corporations such as Monsanto, Agri-Corp, Dupont, Pfizer, Sanofi, GlaxoSmithKline, Purdue Pharma, Bayer, Bank of America, Wells Fargo, Wall Street…Y’all need to stop.
…Cause your paper chasing, nuclear arms racing, natural resource wasting, mass incarcerating, gender discriminating, social-economic subjugating, biased immigration, vindictive deportation, bullying and intimidation , negative socialization, neo-colonization in your quest for validation you’re ripping apart our nation

Even worse, you’re destroying the underpinnings of human civilization…
…our waterways, our trees, our wildlife, our air quality, Global Warming

Climate change is real, I don’t need the ocean to super tsunami me, or the Earth to open up and swallow me…for me to get it…

From the East to the West, the North to the South, the bottom to the top: we need to S – Stand, T – Together, O – Or, P – Perish…STOP!!

An email I will never open

Foreword to Startup Opportunities: Know when to quit your day job by Brad Feld and Sean Wise

Last year, my good friend Brad Feld published Startup Opportunities: Know when to quit your day job, another in his series of incredibly helpful books for entrepreneurs. When I was getting started in the business, I hung on every word of Brad’s blog. So I was utterly flattered by his invitation to write the foreword to his book and thought it would be fun to share here…

“Dear Chris. I have an idea that will revolutionize a $34 billion industry…”

Do you know what that is? An email I will never open. No matter how elegant the prose that follows, I see a snippet like that in Gmail and immediately hit Archive.

Why? As you’ve heard me say for years, “Ideas are cheap. Execution is everything.”

As some point, each of us has had that moment where we say, “Wouldn’t it be cool if…?” Every single human being is capable of churning those out. In fact, I am certain some of you once thought, “Wouldn’t it be cool if I could push a button and have a car and driver show up?” Wouldn’t it be cool if people could rent out their houses for just a couple of days at a time?” “Wouldn’t it be cool if there were an API for payments?” “Wouldn’t it be cool if you could make phone calls and text into your app by using just a little bit of HTML?”

You came up with those ideas, so why aren’t you a billionaire founder on the cover of a magazine? You even bought the endearingly vowel-free domain name, so why aren’t you going public?

Because all the value, all the magic, all the accomplishment, and everything else that matters in entrepreneurship comes in the grueling months and years following the “Wouldn’t it be cool if…?” question.

Since I started making seed investments in 2007, I have been obsessively focused on founders. I spend tons of time with them and go deep in the areas I know well. I never worked on Wall Street or at P&G, and I suck at Excel. So, if we team up, I’m not your supply chain manager or ads optimizer, nor will you catch me estimating Q3 sales five years out.

If we work together, I am there to help you make your product easy and real.

Back in the day, it was expensive to start building a company. Software was proprietary, founders had to buy pricey servers, and they even had to run their own equipment racks in a speedy data center. All of this meant entrepreneurs needed to raise lots of money before they could build anything.

The result? Ideas were splayed across 60-page business plans written by investment banking trainees. Aspiring CEOs were forced to run the investor gauntlet and have every assumption questioned. Hand-wavey bullshit artists with dog-eared copies of Getting to Yes and Starting with No on their genuine faux leather coffee tables drove the painstakingly Socratic process.

Today, with open source, AWS, GitHub, and coffee shops with free Wi-Fi, there are few barriers to taking an impulse and slapping some code on it. Just $99 will get you a solid logo and smooth-looking homepage that makes it look like you know what you’re doing. No more professional networking connections needed, no fancy B-school degrees, and no slick-talking pitch doctors. These days, builders gonna build.

Raise a glass to the democratization of it all! And best of luck to all the now unnecessary investment bankers with incredible PowerPoint and personal grooming skills who have since moved back to New York City to apply their talents to some predatory lending scheme or mass layoff.

But the downside? Too many of you who are founding stuff are skipping the part where smart people beat the shit out of your idea over and over again before anything gets built.

When I first got into this investing business full-time, I was holed up at Brickhouse on Brannon in San Francisco hearing back-to-back pitches. Small teams who could show me live code were impressive. I loved being able to play with a site or an app rather than merely considering a hypothetical.

Yet, almost everything they showed me was irretrievably misguided from the get-go. I met hundreds of entrepreneurs who didn’t even know their own competitive landscape, let alone have the ability to describe to me in plain English why they would win the space. It was devastatingly clear: They hadn’t done the intellectual work that would be the foundation for everything that came next.

In 2008, I’d had enough of these frustrating conversations, so my wife and I moved to Truckee, a small mountain town near Lake Tahoe. Our thesis was that instead of running from coffee to coffee, we’d identify the most intriguing minds in startups and invite them up to our house for weekends. We would go deep with the founder whose thinking challenged ours. Whether we were skiing, hiking, cooking, playing music, or snowshoeing, we were also spending that time batting around visions and predictions and controversial points of view. For days at a time, we just jammed on ideas, pushing one another’s reasoning, testing assumptions, and forging moments of clarity and inspiration.

We soon realized that this worked elsewhere as well. Whether we were in Austin, San Francisco, Montana, New York, Paris, Oxford, Boulder, or Vancouver, making time for meaningful group discussion was not only the most fulfilling way to spend time, but it was leading to more genuine friendships and, ultimately, much better ideas across the board.

So who was in those jam sessions? Founders from Twitter, Instagram, Twilio, Uber, Lookout, Stripe–you get the picture. Sure they are legendary companies today, but consider what those early jams were like. For example, as obvious as Uber may seem today, extensive creativity, original thinking, and robust debate were necessary to hone in on the real problems in the industry and focus on a solution to build.

These great entrepreneurs didn’t just come up with a great idea. They started with a notion and bounced it around a lot before ever starting up the business. Who they bounced it around with was vital. Early co-founders, advisors, friends, and mentors made a huge difference. What they did with the idea mattered. If they just sat on it, it died. But if they ran around and talked to a bunch of prospective customers or users, it got better. If they actively listened to feedback and incorporated some into their plans, it got even better.

The most successful founders are listeners, thinkers, and tinkerers. They are iterative, reflective, and rigorous. They passionately believe they are right but enjoy when their assertions or conclusions are shredded. The very best feel that yes is boring, and they thrive when wrestling with no.

So take that cute, native idea of yours and throw it to the wolves. Ask your peers to tear it up. Meet with fellow entrepreneurs and invite them to bury it. Take what’s left after your mentors spit it out and head back to the whiteboard. Stay up all night jamming. Do this again and again and again, and you’ll realize why founders of billion-dollar companies may be lucky, but their success is never an accident.

I hope to see your name among theirs soon.



[I wrote this post almost ten years ago for my old personal blog, What Is Left? I thought about abridging it because our attention spans aren’t what they used to be, but here it is reproduced in its full, unadulterated glory save a few edits for the sake of clarity.]

Over the last few months, I have felt a strong urge, and almost responsibility, to share with my friends why the Obama campaign and presidency meant and mean so much to me. However, each time I’ve attempted to spill my thoughts onto a page, I’ve been intimidated and paralyzed by the breadth of possible approaches and the profundity of each of our experiences and motivations. The scope and gravity deterred me, and this blog has remained stale.

Scattered across various hard drives, journals, and throughout my Gmail account are snippets of reaction and inspiration from each stage in which I participated. While a tech adviser to the campaign, I detailed arms-length paragraphs of intellectual assurance and optimism. Service as a campaign surrogate triggered notes of trepidation that soon evolved into a deep feeling of privilege and gratitude. Of course, the inauguration itself was a singularly impactful event to witness. I could, and did, draft pages of real-time reflections at each of these stages. Yet, I think the notes from my time on the road leading up to election day serve as the best illustration of my thoughts…

When my truck and I left San Francisco, my original aim was to spend some a couple of weeks driving around the Rockies interleaving time on my mountain and road bikes with campaigning for Obama in places it mattered, such as Nevada and Colorado. My parents had bestowed upon my brother and me a youth hallmarked by consecutive summers in the mountains of the American West. I had sorely missed them and needed a booster inoculation of the awe and humbling context they uniquely inject. In parallel, I saw a mounting number of friends Twittering about their contributions from the trenches, and their labor left me feeling like a free-rider.

Fueled by a freshly compiled road trip playlist (a lost art, I would argue), I drove straight through the night to Winnemucca, NV. The next morning, awakening at the Red Lion Casino, I did some impromptu and unofficial canvassing. The folks who spoke to the unmistakable San Franciscan likely self-selected and I enjoyed our polite banter. I will cop immediately to profiling those whom I approached as well.

After a few hours of glad-handing in greasy spoons on Winnemucca’s main/only strip, I grabbed my bike and peeled off to some wonderfully isolated and meandering single track on the infamous Bloody Shins Trail. Oh, to be out of the city and unmitigatedly alone on my bike breaking trail and wrestling sage. When I got back to the parking lot, I was spent, but bursting with endorphins and assured I had made the right choice in making this trip.

I dropped back into town to grub and consider my trip’s next stop. Food in my belly, and with an eye on making it to Elko that evening, I paused to fill up my tank, still wearing my favorite bike jersey and a peaceful grin that always follows a few hours on the pedals.

I didn’t notice their truck when I pulled in, and couldn’t describe the driver or passenger. I have no idea whether they were wearing the clothes you would stereotypically associate or playing the music our own prejudice might lead us to expect. All I can say with certainty is that as that white Ford F150 accelerated past the pump island in retreat, I was called a “n***** lover” and an empty beer can hurled at me fell limp to the concrete within a few feet of release, its depleted mass no match for the slight breeze.

As a white man from Middle America, [with a burgeoning and in retrospect somewhat naive sense of what we might now call wokeness], I grew up with a very academic perspective on race. White dudes like me see the prescribed Oscar-nominated dramas preaching color blindness. We seek out the black kid in our school and feel exonerated when he greets us with a demonstrably soulful handshake. We are convinced that the poignant lyrics from activist hip-hop resonate with us and we grow unwaveringly confident that we understand the struggle. Yet, the privilege of our skin color does not prepare us to ever be the object of hate.

Thus, I was knocked on my heels by that epithet. I felt shaken, angry, scared, paranoid, sad, and dozens of other emotions simultaneously. I fled Winnemucca and headed West. I’d like to say it immediately strengthened my resolve to work that much harder on the campaign. That would indeed be the honorable reaction. However, initially, it just freaked me out and made me want to desert the reality of this era in our nation.

On Interstate 80, I was soon clocked doing 88 in a 75, the radar likely underestimating my true speed. The cop issued me a ticket without any protest on my end. As he released me from his charge and sent me on my way, I gently interrupted him and told him what had just happened in Winnemucca. I wanted another human being to sympathize, I guess. Upon hearing my account, without hesitation, the officer uttered incredulously, “Well, what’d ya expect?”

Reflecting back, I think that was the impetus for a renewed resolve to do my part to get Obama elected. I pulled up the campaign web site on my iPhone, found the next field office, and charted a course for Elko, NV (a decidedly straight course with no turns, actually).

Elko is a strangely conflicted and anachronistic place. It is essentially a mining town combined with a handful of truck stops, cheap flophouses, and a few casinos. The citizenry is working class, yet notably evidencing poverty at every turn. Those who aren’t employed in serving the transients in need of gas, chow, and lodging, are primarily ranch hands and miners. This was the high desert and I awoke my first morning there to find tumbleweed cartoonishly wedged under my truck.

I walked in to the local Obama office, a clearly improvised outpost just off of Main Street. Greeted by a pair of impressively optimistic volunteers, I was soon introduced to Brendan Ballou, a bone thin 21 year-old college student on leave from school to run the Elko HQ. This kid was brilliant. He moved deliberately and thoughtfully, and operated with an almost obsessive inclusiveness.

Elko’s population is fervently Republican and has a unique ability to be harsh and hateful. Their beliefs are often untenable, but trying to convince them otherwise is frequently futile and has apparently threatening consequences. Nevertheless, at each turn, Brendan stayed remarkably cool. It made more sense when I learned that his first posting of this contest was in a little northwestern town known as Wasilla, AK. Talk about battle-hardened.

Brendan and his trusted organizer Kenny Wyland (coincidentally, a Google engineer) would send us out on canvassing missions issuing each of us lists of names and addresses from voter registration rolls as well as Obama platform enunciating leave-behinds. My routes often took me into the most sparse ‘suburbs’ of Elko with a mile separating dwellings.

I must admit, walking up on the porches on many of the poorest permanent dwellings that exist in this country scared the hell out of me. As a child, I had gone door to door selling candy bars to raise money for sports teams and even then I knew to skip the curmudgeonly old man in my neighborhood’s corner house who used to yell at us if we merely approached his property. Being told I was a terrorist, a n*****, and a traitor just burned that fear deeper into my marrow. Though I struggled to never show the authors of such disdain any returned disgust or reproach, they wore me down. On my second day out going trailer to trailer, I returned to find dogshit had been hurriedly rubbed onto the passenger side of my truck.

In just a short time, Elko was taking its toll on me. At night, in my hotel, I would find myself so angry. The uncomfortably loud Fox News they played in the breakfast room never helped. Only intermittently would I visibly hint at the outrage provoked by the theater of security and patriotism that was destroying my country, a place in which my pride has only ever been strengthened by my time abroad.

I decided to leave. I needed a break. I was eating like crap and acutely depressed. I punched my wall on one night. I didn’t recognize myself. I had worked incredibly nasty jobs growing up, and am quite comfortable in what we white collar folks consider to be the stresses of our coddled employment. However, nothing had prepared me for the daily personal assault from the mouths of these vitriolic people.

I had never been to Moab, UT before, though it had been a goal of mine since I fashioned my own mountain bike out of my dad’s ten speed by attaching a BMX wheel on the front. Google Maps told me I could get there in a long drive and arrive the next morning. Thus, I took some time off of the campaign. Though ‘escaped’ is probably a better and more honest word.

Along the way, I stopped in Bryce Canyon, a favorite place to which my parents first took me at 6 or 7. Within hours, I started to feel “normal” again–a privilege that belonged to me as a white person. The beauty and persistence of nature was washing the negativity from my mind. I ran along the canyon floor and then up around the rim, clearing my head and restoring some focus. But, I was still afraid.

I didn’t know if i had the strength to go back to Elko. I had invited a pile of friends to rendezvous in Vegas and thought that might be a delightful place to celebrate an Obama victory. But, I hated the weight of self-doubt knowing that Elko had tested me and I failed.

Once again I stalled, rationalizing the realization of a vintage fantasy by heading to the renowned undulating mountain bike trails of Moab. I arrived as a stormy curtain fell dramatically on the park. With the sky unapologetically pouring, all riders on the course frantically made for the parking lot. I tried to head out, but the ‘Moab slickrock’ was living up to its name and my wheels could find no purchase.  Lightning came and I fortunately found a small cave in the rock hoping to wait out the veritable hose. My patience paid off and as the dry rock soaked up that water, I, in turn, flowed up and down over those surreal surfaces for hours, entirely alone for the duration of my adventure.

I choke up now reflecting on that beauty. The unreproducible light of magic hour dancing in a ballroom where millions of years of weather had perfected its own steps. Just to ensure I was permanently tattooed with the memory of this unique and solitary event, a rainbow emerged, and all of ROYGBIV winked at me, acknowledging the vast catharsis we had to ourselves.

I don’t believe in god, but I do believe in church, and I couldn’t help but bow at this altar. Humbled. Vulnerable. Grateful. The ride back in was in a dark of rare purity, my wheels undulating in surprise waves of rock that escaped my headlamps. Tossed and bucked, I clung to my steed and laughed at my merciful fortune.

Back in the parking lot that night, I had no doubt: I needed to go back and do my work. I thought about the brave people who came into that office every day undaunted. I remembered the determined faces of volunteers who lived in that community and who didn’t have my comparative luxury of leaving. People who never had the education and countless chances and repeated forgiveness I’ve been offered. Citizens whose misfortune was unrecoverable. Yet, they showed up each day ready to knock on more doors, in the cold, in the dark, and past foreboding dog fences. I drove back to Elko through the night.

In my career, I get heaped with empty praise I don’t deserve. Papers get carried away in a flurry of colorful and prophetic adjectives bathing me in baseless optimism. Venerable universities and corporations ask me to come spout scraps of blather raked from the confined yard of my experience so far. But, here I was, back in Elko, a worker among workers. Each astonishing American walking through that door another reminder of how much I undoubtedly had to learn and of how unjustly lopsided my life has been.

Inspired, the remaining few days until the election went by more quickly and purpose overrode the pettiness of the local citizenry’s attacks. In a way, I began to appreciate their fear, their yearning for control, their desperation for some sense of self-determination — even when it expressed itself in vile racism. To the degree possible subject to the hypocrisy and myopia of my comfort, I sympathized.

On election eve, the carnival came to Elko. At 10:30 pm, Sarah Palin strode into the Elko High School gymnasium, there to deliver her proprietary blend of xenophobia, division, and exclusion. Though she feigned confidence and assured the room of her impending triumph, we could nevertheless feel the failure of her message. She underestimated America and her naïveté made me smile.

The Obama team arose exceedingly early on election day, our hands warmed by a box of donut holes and the exhaust heat from the printer spooling names and addresses of those whom we needed to ensure found their ways to the polls. Voting hours ticked by without major incident, the unfriendly lot having now learned to not answer their doors when the obvious interloper came knocking.

With 30 minutes left to vote, I approached the porch of what my tattered list told me was a 91 year old female Democrat. Was she able to get herself to the ballot box that day? I rapped on the door and she answered leaving the flimsy aluminum and wire screen between us. “Hi, I’m Chris from the Obama campaign and I just wanted to make sure you had a chance to vote.”

She didn’t utter a word. Instead, she inched toward the handle, pushing it loose and motioning for me to perform the rest of the opening. As I stepped onto her weathered rug preparing to make my pitch, she reached her frail arms around me and hugged. Silently.

I lost it. I didn’t just let a tear or two slip. I audibly let out 8 years of embarrassment and helplessness. She quickly hoped to comfort me by leading me inside where her family was gathered watching the returns and smiling with the anticipation of an Obama victory. She offered me soup.

Wiping my cheeks, I got back in the car with the local retiree who was driving me from one far flung address to another in our last minute harvest of votes for the good guys and we returned back to the warmth of our field office nook, tucked a block from the formerly main drag that Nevadan sprawl had left behind.

Our orders were to remain at the post until an outcome was deemed certain. Nervously, we hesitated to celebrate any forthcoming success, many of us bearing scars from 2000 and 2004. When the call from campaign headquarters finally came, we erupted, but not in the self-congratulatory jubilation that comes with vanquishing a competitor. Rather, the room was consumed by embrace and tears. Disbelief. Shock. Relief. Wonder.

We spent the next hour hearing tales of the two years many of these selfless and saintly individuals had spent grinding out each vote for our candidate. For the first time in years, it wasn’t my turn to give the speech, to thank everyone for their contributions. Instead, I shut up, listened, and admired.

The official Elko Democrats celebration was held in a room off the casino floor at yet another Red Lion. A large projection screen was tuned to the networks reviewing state by state results and the cavernous room emphatically contextualized the mere 15 attendees of that party. I think you’ll understand my insistence on reclaiming the term McCain resigned to expedient cliché, and express that these other folks in the room were indeed the true mavericks.

The next morning, driving home across stretches of snow-dusted desert with exactly no bars of phone or data service, I struggled to digest what had just taken place. I couldn’t play music and I wasn’t singing. My sense of self was overwhelmed as I reflected upon our privilege. We are the luckiest people in history.

My hero and posthumous mentor, Buckminster Fuller wrote:

“We are blessed with technology that would be indescribable to our forefathers. We have the wherewithal, the know-it-all, to feed everybody, clothe everybody, and give every human on Earth a chance. We know now what we could never have known before-that we now have the option for all humanity to make it successfully on this planet in this lifetime. Whether it is to be Utopia or Oblivion will be a touch-and-go relay race right up to the final moment.”

Revolution still flows through our blood and is baked into our firing nerves. Yet, we had become a nation of rationalizing, complacent, discouraged victims. Along comes a black man with a most politically inopportune name and he stirs within us the pride, courage, and defiance that we had conceded to the reaches of our past esteem.

It will undoubtedly be a relay race until that final moment, and Barack Obama stirred each of us to seize back the baton. With this opportunity, each of us inherits a responsibility. To act. To listen. To empathize and care.

President Obama is not a panacea. However, he is the catalyst for our seemingly final attempt at redemption. Our collective prosperity will not be awarded by some roll of dice or drawn numbers. It must be earned. Sweat, humility, and diligence will produce our grace and will convince the fates to return to us our shared destiny.

In that spirit, I hope that this year, and each that follows, I can simply be helpful. Each of us owes nothing less to each other. Thank you to our President, and each of the indescribably estimable souls who toiled to get him elected, for reminding me of that.

[Damn, I miss that guy.]

How You Can Help Us Save Democracy

Like most Americans, Crystal and I were hoping rationality, fairness, and compassion for our fellow humans would prevail in the 2016 elections. Whoops.

Since then, as our democratic way of life is under assault every day, many of you have asked, “What do we do now?” Early on, we didn’t have good answers to that question. So we rolled up our sleeves and got to work.
Together with our Chief of Staff, Clay Dumas, who joined us from the Obama White House, and countless advisers and researchers, Crystal and I dug into what went wrong.

In 2016, Democrats made some fatal errors. A lack of good data combined with old-school insider bias led to bad decisions about which races to invest in. Failure to adapt to an evolving media landscape meant Democrats were using weak and costly tactics in trying to reach voters. Even worse, the establishment’s intuition about which messages would persuade and inspire voters was dead wrong. All of this was compounded by too many local races without Democrats on the ballot. You can’t win the lottery if you don’t buy a ticket.

Understanding what went wrong has honed our approach to 2018 and beyond. We found we need to:

Focus on the House.

We need to win back at least one chamber of Congress, and the expected likelihood of turning the tides in the House is higher than in the Senate. Don’t get us wrong, America would be in much better shape if we won the Senate, and we’ve personally contributed to multiple efforts on that front. But, the best bang for the buck is in the House races. As part of this, we also know that compelling down-ballot candidates can bring more voters out when it matters and position us for fairer redistricting in 2020.

Spend our money smarter.

As much money as Democratic candidates are raising from the grassroots, SuperPACs and dark orgs will ensure the other side has a lot more cash saturating traditional and digital media. Campaigns with better creative, research, testing, and mobilization tools will be much more effective and efficient.

Persuade more people to vote for Democrats.

In many districts, we won’t win just by turning out our base. We need to find support in the middle and across the aisle by using smart and well-informed messaging to help voters understand why it’s in their best interest to choose us, and we need to get those voters to show up.

Run everywhere.

A failure to recruit candidates for hundreds of local, state, and federal races in 2016 cost us seats in Congress and state houses across the country. Running for and winning these seats means we will have more power to shape legislation, we will be able to reverse the most egregious cases of gerrymandering, and in the long run we will have a bench full of candidates with integrity and a commitment to service.

With these principles as our guide, we spent the last year-and-a-half going deep with the entrepreneurs, organizers, and volunteers who are working to elect Democrats. Dozens of new startups and organizations have launched to help run better campaigns and turn out voters. We made it our mission to find the teams and services that will make the biggest difference in the 2018 midterms and beyond. Rather than only supporting individual candidates (which we’ve done a lot), we’ve been funding tools that will help literally every Democrat running for office.

In that light, we’ve been giving millions of dollars to organizations and democracy startups that are building a new generation of tools for engaging voters, creating and testing the messages that actually get people to vote, making certain that someone great is running in every damn race, and ensuring that the will of the majority of Americans is never again ignored.

Here’s what you can do to help

After meeting with a staggering number of teams, studying their product roadmaps, evaluating how they’ve performed in special elections, and cutting a bunch of our own checks we were able to draw some solid conclusions. What follows are our recommendations for how you can donate your time, talents, and dollars to help save this country we all love.

Swing Left

Take Back the House, District by District

Swing Left is a national grassroots organization of volunteers supporting Democratic candidates to flip the House in 2018. They channel people’s energy and dollars into the swing districts closest to where they live. They’ve done the hard work of figuring out which districts actually have a chance of flipping to blue. In each district, they’ve been hard at work 1) recruiting and training volunteers to walk door-to-door and make calls and 2) raising money into “District Funds” where it was held until the Democratic primaries wrapped up. This ensured that millions of dollars in grassroots donations didn’t fund Democrat-on-Democrat fighting.

It works: In Conor Lamb’s special election in Pennsylvania last Spring, Swing Left volunteers generated half the calls (200k), knocked on roughly 8,000 doors, and raised $124k for the campaign—directly resulting in hundreds of additional votes in a race whose margin was only 627. Swing Left is hustling to ensure upsets like Lamb’s play out across the country on November 6th. Overall, giving to Swing Left is the most efficient way to invest your time and money in politics in 2018.

Volunteer: No one makes it easier to change hearts and minds in key races when it matters most: We promise nothing will make you feel more connected to democracy than talking one-on-one with your fellow Americans.

Donate: If knocking on doors isn’t your thing, Swing Left makes it easy to donate directly to the most competitive races where Democratic challengers are in need of resources: Crystal and I have helped fund Swing Left’s operations, so your donation goes further and directly into the field where it will be immediately effective.


Persuade Friends to Vote

If you’ve ever volunteered on a campaign, you know the roles and resources can be limited. Team, built by The Tuesday Company, gives us all a new way to volunteer. It draws on social media to help friends persuade friends to vote. Frankly, it’s the tool the Hillary campaign wish they had in 2016.

In campaign lingo this is called ‘relational organizing.’ All that means is drawing on existing relationships instead of talking to strangers. There are a few different startups working to bring it online, and we believe Team is the most effective. An early focus on Facebook and texting, together with their experience as field organizers, has resulted in one of the best new campaign tools to emerge this cycle. Team is being deployed in the most competitive Democratic campaigns in the country, with a special focus on House races.

Download the app: If you have a few minutes and you want to help connect your friends with your favorite campaigns, start using Team today by downloading the app here:

Jobs: They have a number of full-time roles and internships in New York: If you’re interested in applying, send your resume and a sample of your work to


Connect Volunteers with Campaigns

MobilizeAmerica is the indispensable platform for campaigns and political organizations to recruit volunteers. Before Mobilize, the best way for Conor Lamb’s campaign in Western Pennsylvania to get people in the door was to list the office address on their website and hope people showed up. Mobilize made it easy for Swing Left and nearly 100 other grassroots organizations to recruit volunteers on behalf of the campaign. Between late February and the special election in March, campaigns and organizations on the MobilizeAmerica platform scheduled 4,041 volunteer shifts for the Lamb campaign, helping to turn out thousands of additional voters in a race that was ultimately decided by just 627 votes.

This Fall, MobilizeAmerica is directly supporting more than 300 of the most competitive congressional and statewide elections, and they’ve got deals in place with everyone from Swing Left and MoveOn to the DNC and DCCC. Together these partners have more than 20 million members that they’re pushing to volunteer on hundreds of campaigns. With MobilizeAmerica as the backbone of volunteer recruitment, there’s the potential to book more than one million volunteer shifts in competitive races across the country. We’ve never had a tool like this before, and it could prove to make all the difference.

Volunteer: Chances are the campaigns closest to you are already running on Mobilize. Find the highest impact opportunities to volunteer here:

Jobs: They’re hiring for engineering, design, and partnerships roles: To apply, interested candidates should email:

Democracy Works (TurboVote)

Makes Voting Easy

Democracy Works is a team of software developers and civic organizers working to upgrade the infrastructure of American democracy. Their best-known product is TurboVote, an online service that helps anyone in America vote in national, state, and local elections.

This year, they’ve quintupled their users from one to more than five million. That includes 486,966 on National Voter Registration Day (September 25th) alone, thanks to deep product integrations with Facebook, Twitter, Snapchat, Instagram and Google. Working with these platforms along with companies like Starbucks and Salesforce with lots of employees and even more customers, they’ve set a challenge to increase voter participation to 80% by 2024.

Democracy Works is also the team behind the Voting Information Project, a data collaboration with Google and the states which makes it possible to search online for your polling place, and Ballot Scout, a digital tool that helps local election administrators keep track of millions of mail and absentee ballots so that they make it to voters in the first place and get counted in the final tallies.

Sign up for Turbovote: Make sure you’re registered and receiving updates about elections by signing up here: Send that link to all of your friends and share it on social media.

Donate: You can donate here to support Democracy Works: This is a 501(c)(3) tax-deductible organization that spends every dollar it raises building technology that makes voting simpler and more seamless for all, so you can be proud of the impact your contribution will have.


Democracy via SMS

Resistbot started out with a simple premise: make it easier for people to contact their elected representatives. In the early days of the Trump regime, ResistBot built an SMS bot on Twilio that turned text messages into faxes, allowing constituents to register their opinion with Congress. As old school as it sounds, Congressional staffers all say that faxes go a long way in influencing representatives. Working with a volunteer force of engineers, Resistbot grew to more than 4.3 million users in year one — the biggest SMS list in politics.

The next test for this incredibly lean team comes this fall as they work to convert all that energy into votes. First, they built tools to check if you’re registered, remind you about keys dates, lookup your polling location. Now, they’ve launched the first ever SMS voter registration tool. It’s currently live in California, Colorado, Florida and Illinois.

Sign up: Text VOTE to 50409 and pledge to vote on November 6 and contact your representatives. Then tell your friends to sign up too.

Volunteer: Resistbot is churning out new features, and they could use some extra hands. Email them at if you want to move fast and fix civic engagement with them.

Donate: You can donate here: Confidently know that every $1 you give funds messages to over 100 people.

Run for Something

Get Inspiring, Meaningful, Authentic Candidates to Run

In 2016, 40% of down-ballot state legislative races went uncontested. Run for Something is fixing that by recruiting young and diverse candidates to run in each and every down-ballot race across the country, from school board to state senate. So far, 18,000 people have registered their interest to run for office with Run for Something, and this November they’ll have 406 candidates on the ballot, exactly half of whom are women and nearly 40% are people of color.

In addition to recruiting people to run, they help them win. They’re on the lookout for candidates who are progressive, rooted in their communities, and focused on making face-to-face contact with voters–the scientifically-proven most effective way to increase voter turnout.

In 2017, they endorsed 72 people across 14 states, and 50% of their first-time candidates won. The win rate for first-time candidates is usually closer to 10%. Of those winners, 51% identify as women, and 40% as people of color. In 2018, they’ve already endorsed over 630 candidates in 48 states, making them essential to taking back the state houses and local governments that can keep America on track. Run for Something will turn out voters for school board and state rep which has a documented reverse-coattails effect on candidates higher up on the ballot. So this is as important as anything else we support.

Donate: Knowing that every dollar raised helps bring down the barriers for more young and progressive candidates to run for office, make a donation here:

Run: The surest way to make a difference? Run for something yourself:

Higher Ground Labs

YCombinator for Democracy

Higher Ground Labs incubates and accelerates companies that help progressives reach voters, organize volunteers, and manage campaigns. Think of them as a YCombinator for democracy. In just over a year, this lean team of Obama campaign staff-turned-entrepreneurs has established itself as an indispensable clearinghouse for Democratic campaigns and a center of gravity for political tech. Higher Ground Labs is both a magnet for the most talented startups and a trusted brand among the old-school party committees. That means the best new tech is coming out of Higher Ground Labs and immediately getting the biggest Democratic orgs signed on as customers. We have funded both the accelerator itself, as well as some of the companies that have graduated. These investments are already paying off for Democrats, but more innovation and scale depends on support from you.

Jobs: Their jobs page is full of opportunities across their portfolio:

The Arena

Coaching the Next Generation of Leadership

The Arena coaches promising first-time candidates in storytelling, organizing, and campaign management to help them reach voters with their most compelling messages. They’re a diverse team of former Obama appointees, campaign managers, and technologists who recognized the need to invest in new blood. They work on both federal and state races, helping candidates like Lauren Underwood, who captured the Democratic nomination in Illinois’ 14th congressional district. In March, Lauren–who is 31, black, and a former appointee to the Department of Health and Human Services under Barack Obama–captured 57% of the vote in a 7-way primary where the six other candidates were white men. In addition to coaching candidates, they’re publishing toolkits and templates that help a broad set of young and first-time office-seekers get up and running.

Use Your Talents: If you’re a creative who can help candidates tell their stories through words, design, or video, your talents are needed. Please email Ravi Gupta:

Donate: Every dollar they raise helps the Arena add candidates to their roster and increases their chances of winning. Donate here.

Creative Action Network

Art with Purpose

The Creative Action Network is a community of artists and activists making art with purpose. They run crowdsourced campaigns around causes, inviting artists of all stripes to contribute their own meaningful work. After the election of Trump, they ran the What Makes America Great  campaign to focus on the many things that truly make this country so special. Then they turn campaign designs into posters, apparel, and home goods that they sell online and in retailers across America. Proceeds from every purchase go to support causes, from national parks to civic engagement. The Creative Action Network grew out of a grassroots collective of artists and designers during the Obama campaigns who discovered the power of art to make change.

Use Your Talents: Calling all artists and designers to contribute work to one of their campaigns:

Purchasing Power: Check out the many inspiring pieces of art and books that have been contributed by artists from across America. Buying and displaying art like this where you work and live will both support the underlying cause and remind all who see it of what matters most.

One special note, Crystal created this Everyone Welcome art which has gone on to be one of their most popular works and frequently can be seen in store windows or on classroom doors.

The vast majority of Americans agree–this childish fraud has been a disaster. His policies are cruel and ignorant. The damage he’s doing is traumatic and potentially irreversible, yet the GOP is complicit and fully embracing the trampling of American history, values, and norms.

To see him separating kids from their families at the border, stoking the flames of racial bigotry, prying healthcare away from hard-working Americans, shrinking public lands, legitimizing white supremacy, starting pointless trade wars, defiling the environment, bullying his opposition, appointing craven hacks to the Supreme Court, and denying the climate crisis are among the countless things that make us sick.

On top of that, he’s abusing his power, assailing civil servants, de-funding critical programs, undermining law enforcement, encouraging violence against the press, shattering our global alliances, embracing despots, and outright lying to the American people multiple times a day all while lining his own pockets with fraud and corruption right out in plain view. He is a dark stain on the fabric of this great nation.    

If you are also furious, anxious, and just downright exhausted by this evil, feckless tyrant and his enablers, please take these actions right now to unseat his power and save the United States of America.



I hung up my spurs.

A few years ago, my wife Crystal and I were cleaning out our garage in Truckee when we came across an old notebook of mine from when I lived in Ireland at age 20. Back then, a friend had asked me, “What do you want to be when you grow up?” and I jotted down an answer.

Despite never having heard of venture capital, I went on to describe a job that would involve “a lot of time on the phone negotiating” and overall “high risk, high reward.” I envisioned it as a very lean operation, possibly working out of a bare warehouse, and I would do it half-time from the mountains and half-time from the beach. Last, I predicted that whatever this job was, I would “be the best” at it and then “quit at 40 to try my hand at something else entirely.”

Well, though these days most of the negotiation takes place over email and not on the phone, I did go on to risk every dime I had, more than once, and I built Lowercase Capital. As prophesied, Lowercase has earned its spot among the best funds ever, landed me on the Forbes Midas List, and changed my life forever. All this despite never having actual office space. Instead, I’ve always worked out of my homes in Truckee, California, and Big Sky, Montana (mountains), and Los Angeles near the water (beach).

Thus, in April of 2017, I retired from startup investing. I was 42 and had missed my deadline by two years.

It has been hard to leave all this behind right when things are going so well. I’m good at what I do and still improving as I learn from mentors, founders, partners, friends, family, strangers, my own investors, and the experience itself. The better I get at investing in and helping companies, the result is more founders who are excited to work with me and more of my wonderful limited partners insisting I take piles of their loot to keep it all going. People offering you risk-free money is generally considered a positive thing. But, as I increasingly realized…

Startup investing is one of my things, but it’s not my everything.    

For a few years, I tried to do this job part-time. But my personal style of startup investing doesn’t work when I’ve just got toes dangling in the water.

The only way I know to be awesome at startups is to be obsessively focused and pegged to the floor of the deep-end gasping for air. I succeeded at venture capital because, for years, I rarely thought about or spent time on anything else. Anything less than that unmitigated full commitment leaves me feeling frustrated and ineffective.

As you’ve heard me say on Shark Tank, if I’m not all-in, I’m out.

So what does this mean for Lowercase Capital itself?

We still passionately support our current portfolio companies as well as the countless startups that we have sold or that died off along the way. When we invested in startups, we made a commitment to help them for years and years. That hasn’t changed and we are busier than ever being helpful. We just aren’t investing in any new companies and we won’t accept any new money from investors.

So, all this sad news aside, when are you going back on Shark Tank again?

The love I got from you guys during my seasons on the show was incredible. It choked me up at times. When I first sat in that chair, I wasn’t sure what might happen and what you all might think. Turned out, the Twitter feedback was teeming with high fives, my episodes’ ratings were strong, the press and critics loved it, I invested in some fantastic companies, and most importantly, I had so damn much fun. We even won some Emmys! You all made Friday nights so special for me.

But no more Shark Tank. There simply wasn’t a way to do Shark without investing in a bunch more companies. 

Funny enough, the person who is most bummed out to hear I won’t be back is Mark Cuban. Despite what you might surmise from on screen, he and I are actually good friends, just really competitive good friends. I miss working with Mark, and all of the other Sharks. Each of them has been incredibly generous and warm to me and I am proud of all the episodes we made together. (Oh, and for anyone paying extremely close attention, I did come back for one episode and a couple of update segments in Season 9. But who’s counting?)

Really? You just walked away from Shark Tank?

I loved taping the show. You can’t necessarily tell when watching at home, but those pitches are each usually an hour long and many are emotional, hilarious, and inspiring. Watched by millions every week, across red and blue states alike, it’s refreshing how many new people from outside my bubble continually reached out to talk with me. The show quite simply embodies the American Dream. You might still catch me doing some TV like the Zach Braff’s series that cast me as myself and I always enjoy a good podcast episode. But no more Shark. 

Wait, is quitting all this stuff a prelude to running for political office?

No. If you follow my Tweets, you know my attention and anxiety have been intensely focused on the plight of our democracy. I don’t say that lightly. I think the institutions, principles, norms, and traditions that make the United States of America genuinely exceptional are at serious risk. It has been hard to think about anything else.

As a rich white guy, being an activist/loudmouth in the #resistance often means taking up political positions that are against my own apparent self-interest. These oppressive zealots in the White House are giving people like me a massive tax break and adopting policies that make my already charmed life even easier all at the expense of those Americans who most need our help. But I was raised by parents who instilled in me a deep sense of gratitude and an obligation to give back the gifts I’ve received. My life has been guided by experiences here and abroad that highlight how much we are all in this together.

This is a good time to note that my success would not have been remotely possible without robust public education, access to healthcare, government creation and nurturing of the Internet, federally funded research and science, and the talents of brilliant people from literally around the world. My career would not have progressed without the leadership and contributions of immigrants of virtually every race, ethnicity, and faith. Period.

So, I owe it to do what I can to help, now more than ever.

That kinda sounds like you’re running for office.

I assure you, that’s never going to happen. Nevertheless, I am spending a great deal of time meeting with all of the beautifully spontaneous and decentralized organizations that have been popping up in the wake of our electoral calamity as well as dozens of candidates at all levels of government. I find so much hope in the new wave of leaders and builders who are standing up during these times and I am investing and donating millions of dollars to support them. More to come on this.

So how else are you going to spend your time?

You mean beyond fighting a despotic regime while raising three wonderful kids under seven? Fair question. My favorite author, Buckminster Fuller, wrote:

We are blessed with technology that would be indescribable to our forefathers. We have the wherewithal, the know-it-all, to feed everybody, clothe everybody, and give every human on Earth a chance. We know now what we could never have known before-that we now have the option for all humanity to make it successfully on this planet in this lifetime. Whether it is to be Utopia or Oblivion will be a touch-and-go relay race right up to the final moment.

Buckminster Fuller, Utopia or Oblivion

Crystal and I are committed to doing all we can to ensure Utopia wins. We are passionate about solving our climate disaster, criminal justice reform, and women’s issues. We are also deeply committed to paying forward the luck and opportunities we have enjoyed in our space. So we’ve been quietly backing the next generation of investors, but specifically women and people of color who have been starting venture funds. A lot more to come across all of these areas.

Anything else to add, Chris? Or are you just stalling?

Someone must be dicing onions in this room because it’s getting hard to see my screen. I feel so grateful for all you have given me. Not just our investors and entrepreneurs. But all of you. I am very lucky.

Thank you,