1) What you can directly do to help Biden and blue candidates.

2) What we’ve been doing to help save our democracy.

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It would be an understatement to say that a lot of stuff is pretty f’d up right now. I’ll spare you an itemized list. Between your doomscrolling on Twitter and the real-time shitshow you’re living through, you already know.

The good news is that many of today’s messes can be fixed by bringing real leaders back into government. We can take back the White House, hold onto the House, take a real shot at winning the Senate, and flip some state legislatures. However, if we don’t show up, this could be the last free election of our lifetimes. Not kidding. The last four years have revealed how fragile our democracy really is. It’s now or never. 

The truth is, Crystal and I hate politics. However, we are passionate about our responsibility to fight for justice and fairness, particularly on behalf of those who don’t have a voice nor the resources to make change happen. We were deeply involved in the ‘08 and ‘12 Obama campaigns, but since early 2016 protecting democracy has been a year-round job. (And because we work from home and she overhears all of our calls, it’s why our 4-year-old will explain to you the madness of this presidency.) 

Working together with our partner Clay Dumas, who joined our team after four years in the Obama White House, we’ve invested millions of dollars and countless hours helping build organizations and companies that we think have the best shot at giving blue candidates an edge in a game that is rigged against them. More on that below. But first…

What can you do to directly impact the outcome of this election up and down the ballot?

1) Head to Vote Save America: Go right now. Click that link, double-check that you’re registered, and put in your request to vote from home. Now, help your family and friends do it too. You can’t win the lottery if you don’t buy a ticket, and you can’t win an election if you don’t show the F up. While you’re there, sign up for a volunteer shift too.

2) Donate Directly to Biden: If you do nothing else, give a few bucks to the Biden/Harris campaign. We don’t say this lightly. We work closely with the campaign and ensure they are using the best tools and the most effective approaches to putting your money to work. If you want to defeat Trump, your money will actually go further with the Biden campaign than anywhere else right now. One main reason why: They have access to cheaper rates on TV advertising and possess more complete online data than anyone else. Since the next two months will be dominated by advertising on TV and online in swing states, there is simply nowhere else to donate with more impact. Click the link and give what you can. We’ve worked hard to make sure everything you give will go a long way.

3) Swing the Senate: As important as the White House is, save some of your dollars for the Senate. If Joe Biden wins, his ability to pass any legislation at all — from climate to voting rights — will rest entirely on whether Democrats wrest the gavel from Mitch McConnell’s little turtle claws. If Biden loses, a possibility we don’t like to imagine, but one we have to consider, a Democratic-controlled Senate is the only thing standing between us and multi-generational Republican control of the Supreme Court. The good news? We have inspiring candidates within striking distance to win seats in Alaska, Arizona, Colorado, Georgia, Iowa, Maine, Michigan, Minnesota, Montana, North Carolina, South Carolina, and Texas. We need to pick up at least four to flip the chamber. We’ve set it up so your donation on this page will be evenly split 12 ways across the Senate seats where we have the best odds.

4) Defend the House: There are many potentially competitive House races, but we’ve directed our contributions to the 24 races most at risk if the national environment tilts back significantly toward Trumplicans. In other words, if the race fundamentally breaks against us for some unforeseen reason, these are the seats that give Republicans a path back to a House Majority (which are different from the seats you might target if you wanted to maximize the Democratic majority). Do we wish House Democrats had been more aggressive in impeaching Trump and investigating the constantly-expanding list of corrupt behavior? Absolutely. But imagine what happens if the gavel ends up in the other side’s hands. Click here to donate and it will divide your contribution equally among those 24 candidates.”

5) Flip state houses: Not only is our very democracy on the line in the presidential election, but there are dozens of state legislative races that will determine the composition of Congress for the coming decade. Every ten years, after the Census is taken, state legislatures redraw the boundaries of congressional districts. Republicans have a long track record of drawing those boundaries in ways that minimize Democratic representation in the House of Representatives. When Democrats win, we tend to appoint non-partisan committees to draw those boundaries fairly and democratically. These campaigns have an outsized impact on our nation’s laws. Swing Left has made it easy to support the most winnable races in just one click. Make it happen right here.

6) Volunteer your time: Money is helpful, but it only goes so far. From the White House to the state house, campaigns need your time too. Especially in a year when people aren’t exactly clamoring to go out knocking on strangers’ doors, campaigns are in need of volunteers to lend a hand in other ways. Thankfully, the team at Swing Left has taken all the guesswork out of figuring out where to volunteer. Click here, let them know your zip code, and they’ll serve up the very best ways for you to invest your time and organize online. 

7) Sign up to work the polls: Experts are projecting a nationwide shortage of 460,000 poll workers. That’s about half of what is needed. Poll workers tend to be from older demographics who are disproportionately at risk from COVID. Without them this year, the unavoidable outcome is the closure of polling centers, longer lines, and heightened confusion during the highest-stakes Election Day since 1860. So please consider doing your democratic duty and working the polls. Power the Polls has done all the research for you, so all you need to do is sign up here.

**Now, before moving on, stop, go back, and take some action above. We are in the midst of a crisis and way too many people are standing on the sidelines. Don’t feel that same 2016 regret for not doing enough. Instead, be proud of how you helped this time. Get involved now.

What we’ve been doing to help save our democracy

Year-round, Crystal and I, together with our partner Clay Dumas, have been actively funding teams that are rebuilding the tech and organizing infrastructure for the Democratic Party and progressive causes. 

In the wake of the 2016 election, one of the things that stung is that so much of the money raised had been squandered on advertising that didn’t change anyone’s mind, on a data platform that fell painfully short, and on technology that would never again see the light of day after the election. It drove home that political campaigns are like startups with a 100% burn rate. It doesn’t take a very experienced investor to tell you that if all your technology, data, and know-how are held in startups that burn out after a year or two, you’re never going to get very far. 

So instead, we backed scalable, tech-driven platforms and organizations that helped thousands of campaigns in 2018, used what they learned to help thousands more campaigns in 2020, and that will continue to improve, cycle after cycle. In each case, we ask simple questions: For every additional dollar that goes in, are we getting more efficient at winning votes? Are we developing more effective ways to register people to vote? Are we increasing how many conversations volunteers have for every hour they spend canvassing? Are we running more persuasive ads? 

Tech isn’t a panacea, but what Crystal and I knew from investing in startups is that as technology scales, it produces data that refines our understanding of which metrics matter. Over time, this drives dollars toward the tools and organizations that provide the greatest value. This helps campaigns make more informed decisions about whether to spend resources on tools like Mobilize and Reach, or on consultants and mail marketers. Our bet is that, over time, startups inventing new models and building scalable technology will have higher ROI than throwing money at Super PACs and consultants.

After carefully studying the fatal mistakes of 2016 and deploying millions of dollars in 2018 to correct course, we learned a lot. Like many startups, some of the companies we backed early on just didn’t have the chops and flamed out. Others proved effective, but spent too much money to achieve the result. Overall though, companies and orgs that we backed turned out to have incredibly outsized impacts on the race with great ROI per voter.

Armed with that insight, below are the teams we’ve backed for the 2020 election. These investments are focused on: 1) rethinking person-to-person organizing, 2) making it easier to act on the data that informs every decision from which ads to run to which voters to target, 3) upgrading our voting systems so casting a ballot is easier and more secure, and 4) building the bench of Democratic candidates and the tools they use to win elections.

If you’re interested in supporting any of these teams through investments or by working with them, please get in touch. 

RETHINKING PERSON-TO-PERSON ORGANIZING

Mobilize

Enabling campaigns to recruit their supporters

For many campaigns, the primary way to recruit volunteers used to be pasting the office address on their website and hoping people showed up. Mobilize makes it dead simple for hundreds of campaigns and organizations to recruit volunteers and drive them to causes that matter. Today it is one of the most widely used tools in Democratic politics.   

In 2020, Mobilize is powering the largest digital mobilization in American electoral history, driving millions of additional volunteers to Joe Biden’s campaign and fueling volunteer recruitment from organizations like Swing Left to Color of Change. Most critically, as a rapidly growing business, Mobilize has built a platform that will endure for many cycles rather than fade away after the next election.

Reach

Canvass anyone without ever stepping into a campaign office

On campaigns, one of the most important metrics is “doors knocked” or “contact attempts.” To maximize “attempts,” campaigns will send volunteers out to knock on doors even if it’s Tuesday afternoon and they know no one’s home. Common sense might tell you to head to the mall or a college campus, or simply check in with people you already know. Reach allows you to do that, and connects the outcome of those conversations to the campaign’s database.

The Reach founders got started during AOC’s 2018 primary, questioning why a volunteer should have to pick up a clipboard from a campaign office, fill out confusing forms with pen and paper, and drop it back off with campaign staffers where all their work might sit around for a few days before anyone had the time to enter data by hand. Reach built web and mobile apps that provide real-time connections to the voter file so you can “canvass” your friends, family, or a stranger you meet on a subway platform, without needing to go to a campaign office to pick up a clipboard and paper. The data is then immediately available to the campaign, helping to expand and refine volunteer, get-out-the-vote, and fundraising models. With doorknocking obsolete in the time of COVID, Reach’s technology has become a foundational part of over 400 campaigns across the country, who love it because contact rates are 10x higher than when you text strangers.

Swing Left

Connecting you with the top ways to elect Democrats

Swing Left is a national grassroots organization of volunteers working to elect Democratic candidates in the most critical races around the country, from the White House to the state house. When they launched in the leadup to the 2018 midterms, their early insight was to channel people’s energy and dollars into the swing districts closest to where they live. This mission has evolved to help people find the races where they can have the greatest marginal effect on electing Democrats, whether they’re looking to volunteer or donate. 

Swing Left has made political action simple, local, and high-impact, getting hundreds of thousands of people involved for the first time and raising millions of dollars directly for Democratic candidates. We help fund the overhead so that money you give to Swing Left can have more impact in the field.

Team

Persuade friends to vote

Volunteering on campaigns used to mean knocking on doors or making phone calls. Those weren’t always impactful to begin with, and post-Covid going door-to-door and robo-calling strangers is even less viable. Team, built by The Tuesday Company, gives us a new way to volunteer. It draws on social media to help friends persuade friends to vote. In campaign lingo this is called ‘relational organizing.’ All that means is drawing on existing relationships instead of talking to strangers. 

An early focus on messaging, together with the founders’ experience as field organizers, has resulted in one of the best campaign tools to emerge since 2016. Team has been used by everyone from presidential primary campaigns to environmental non-profits to help campaigns reach new voters directly through trusted intermediaries, instead of spammy emails and solicitations from strangers.

MAKING DATA ACTIONABLE

Swayable

Measure content and predict opinion change

One of the biggest missteps of 2016 was failing to measure the backlash of certain messages. What were thought to be persuasive ads only served to alienate certain critical voting segments. Swayable’s mission is to prevent that from ever happening again. Their platform allows campaigns to rapidly measure content with carefully sampled audiences online to make determinations about what to show and to whom.

This is a big deal because ads are usually a campaign’s single largest line item. Swayable’s platform allows campaigns to increase their ROI on that spend by as much as 10x. What really makes it work is that it moves fast enough that customers can test every single ad they’re running. In 24 hours Swayable can show a piece of content to thousands of voters and offer fresh insights. That sort of testing previously would have required six weeks of brand lift tests on paid ads.

Deck

Make presidential-grade analytics available to all Democrats

Deck is a campaign operating system for races from Congress down to the state level. It combines powerful data modeling and targeting tools with best practices in campaign strategy — e.g. how much to spend on ads versus volunteer recruiting — into a single product to give candidates with minimal teams a data-driven strategy right out of the box. The result is to equip campaigns that don’t even have staff with access to presidential campaign caliber analytics and marketing strategies. 

This Spring, Deck partnered with the DNC and is now available to any blue candidate running for state office across the country. Their data is also feeding into other platforms, such as Swing Left’s. In time, this could become one of the most significant advantages of down ballot Democratic candidates.

Stac Labs

Upgrading the data of state Democratic parties

A perennial challenge for Democrats is the inconsistent quality of data from the state parties who often lack the resources needed to maintain and improve their voter files. Stac Labs has gone a long way toward solving this problem by upgrading the technical and personnel resources working on state data. They hire regional data and technology teams with tech industry-level experience to build scalable tech solutions for state parties, negotiate cheaper contracts to tools, and implement best practices in the management of their voter files.

Not only does this allow states to offer the data to more candidates running for office, but it means that insights can more easily bubble up from the local to statewide and even national campaigns. They are now working with 27 states around the country, including all the battlegrounds.

SECURING THE VOTE

VotingWorks

Easy, cheap, and secure voting systems (501c3)

VotingWorks is a non-profit startup and YCombinator alum that builds cheap, secure, easy-to-use voting machines and software. Their team of voting tech and cryptography experts brings together the known best practices — simple UX, paper ballots, and off-the-shelf hardware — into a simple system that is >60% cheaper than current market leaders. During COVID, they expanded their system to include a plug-and-play solution for accessible vote-from-home, available to states with limited experience administering elections by mail. Their soup-to-nuts voting system has the potential to quickly scale across the country in the election cycles to come and restore faith in the physical expression of democracy. 

Most immediately, their biggest impact in 2020 may be through risk-limiting audits, the surest safeguard there is against hacked or faulty voting systems. VotingWorks is providing this software service for free to states — including Pennsylvania, Michigan, and Georgia — who want to assure the accuracy of election results without needing to recount each ballot by hand. VotingWorks is non-partisan and the money you contribute to their work is tax-deductible.

DemocracyWorks (TurboVote)

Make voting easy (501c3)

DemocracyWorks 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 register and vote in national, state, and local elections. If you’re registering to vote on Facebook, Twitter, Snapchat, Instagram, or Google, it’s being powered by TurboVote. 

DemocracyWorks is also the team behind the Voting Information Project, a data collaboration with Google and the states that makes it possible to search online for your polling place and ballot drop boxes. And, critically in 2020, they’ve expanded 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. Once again, this is a non-partisan organization and you can donate money and receive a tax deduction for doing so.

Fair Fight

Defending the right to vote

Fair Fight is partnering with Democratic state parties and others who believe in protecting the right to vote and who work to counter voter suppression efforts around the country. Attempts to discourage and disenfranchise voters take many forms, from administrative barriers in registering to reducing the number of polling locations, from voter ID laws to inventing pretexts to exclude ballots from the final count. These days, it’s whatever it takes for Republicans to prevent young and diverse citizens from voting. This is more than just a matter of partisan warfare. Who can vote gets at the heart of our democratic system: whether people have faith that our government represents the will of the people. 

Fair Fight was founded by Stacey Abrams after her loss by 55,000 votes in the Georgia gubernatorial election where 1.6 million voters were purged from the rolls, hundreds of thousands of votes went missing, 53,000 new voter registrations were never approved, and 30,000 people were forced to vote on provisional ballots, most of which were never counted. Enough is enough.

Voting Rights Lab

Securing voting rights state by state (501c3)

The Voting Rights Lab works to pass laws at the state level to secure and expand the right to vote. They bring together experts from policy, legislative, and civil rights communities to craft strategies tailored to particular states. 

Their efforts span all 50 state capitals, which is where the power to administer elections ultimately resides. This wide reach also speaks to the inherent challenge of defending the right to vote: it is under attack almost everywhere almost all the time. Efforts to disenfranchise voters also take many different forms. This gave rise to the State Voting Rights Tracker, an influential dashboard that tracks changes in voting laws across states throughout the year.

BUILDING THE BENCH

Higher Ground Labs

YCombinator for Democracy

Following the 2016 election, the ecosystem around progressive campaign tech was broken. Rather than build tech and data infrastructure from the bottom up, progressives relied on presidential campaigns to build their own tools. Building tech in-house, with too few resources and too little time, had predictable results. Higher Ground Labs set out to fix this, by incubating and accelerating the deployment of startups that help progressives reach voters, organize volunteers, and manage campaigns, cycle after cycle.

HGL 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 HGL and immediately getting the biggest Democratic orgs signed on as customers. In 2020, products that came out of HGL are serving campaigns at every level, from state house races to the Biden Campaign, and growing significantly year-over-year. No one deserves more credit for fixing Democratic campaign tech than this team.

Run for Something

Get Inspiring Candidates to Run

In 2016, 40% of 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. 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.     

Of the candidates RFS endorsed in 2018 — with money, advice, and coaching — 208 won their races. That represented a 40% win rate (versus about 10% for typical first time candidates). Of the winners, 55% are women and 50% are people of color. Notably, 39 of those victories flipped legislative seats.

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If any or all of these intrigue you, click on their links and dive in. You can donate to the non-profits directly, and if you would like to invest in the other companies and orgs, just let us know. 

Whatever you do, it’s put up or shut up time. America itself is on the ballot. Please, do your part.

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.

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S.T.O.P.

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!
                   
C.I.A
F.B.I.
D.E.A.
N.S.A.
SMH, S-T-O-P…
                   
CDCR, NRA, KKK, F-O-X, OMG S-T-O-P 

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!!

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.

Chris

[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.]