Almost exactly 10 years ago, I threw myself off the cliff of starting a company. I did it because: a) of where Ian helped me realize I was on the risk/experience curve (i.e., more risk tolerant than inexperienced); and b) I was optimizing for minimal regret. In other words, I was very privileged to have had a lot more to gain than I had to lose.
10 years later, I’ve been extremely fortunate to have gained a lot–though not necessarily what I set out to. Most importantly, I now have an incredible wife and 2 amazing healthy kids. Gratitude has become central to my worldview, but being truly grateful also means acknowledging what you have to lose.
I used to never question that every new day could be better than the last if I made it so. But I’m now grappling with the reality that time doesn’t just give indefinitely. At some point, it starts to take too. Yes, some things will hopefully continue to get better: every day our kids get older brings new joys; and I’m excited for what lies ahead in my career. But I’ve also reached the point where my obliviousness to mortality is being steadily chipped away: the older family members or friends’ parents or even friends we lose continue to move from rarity to reality with each passing year. It’s a tautology to say that our time becomes more precious as we get older, but it’s still a hell of a thing to experience for yourself.
I’ve found it challenging to reconcile 30+ years of ambition and competitiveness with the fear of missing out on time with my wife and kids. I used to primarily define my success by achievement, but I now find enjoyment increasingly important. I guess I’m still using a regret minimization framework, it’s just what I don’t want to regret that’s changed.
I’m hopeful that 2019 will be my best year ever just as 2018 has been. But I’m aware that one day–hopefully many years from now–will be as good as it ever gets for me, and I likely won’t realize it until long after the fact. We cannot freeze time to savor those perfect moments. So what can we do other than what the beautiful Ted Rheingold made it his mission to teach us: #EnjoyEveryDay?
Today is a great day for Virginia and for our country. It’s also the first day since my son was born 16 months ago (the day after the Brexit vote) that I am more hopeful than anxious for the world in which he will grow up.
Wait, you guys…are things…not…fucking horrible? What is this feeling I am having? I am unfamiliar with it.
Post-bath Election Night celebration in our house!
I leave it to the people who know a lot more about politics than I do to analyze all the many and complex factors that contributed to last night’s Democratic “tidal wave” in Virginia. I’m not a professional politico, I’m not even a “political junkie” – I’m just a citizen who is concerned for our country and privileged enough to have the time and skills to hopefully be part of the solution (if we need a label, I guess I’m a 5+ Activist). But through Tech for Campaigns, I had the honor of working with and getting to learn about a number of Democratic candidates for the Virginia House of Delegates in this election. And this tweet by @slaby inspired me to share some of their amazing stories.
Last night was a great night for Dems all over. If you're one of the groups and teams who's been helping and experimenting with new models or tech — in the clamor to claim credit, please remember the voters, the candidates, and dozens of other orgs you're sharing credit with.
When I first told Mark Suster about my interest in the Virginia state elections this cycle, I led by talking to him about the policy implications of taking back control of a gerrymandered state legislature like Virginia’s and how it would enable Democrats to enact policies that would benefit the majority of Virginians and be empirical evidence for the benefit of those policies in the rest of the country. In classic Mark fashion, he cut right to the chase and started explaining to me that policy was all well and good but people vote for candidates not policies. And in classic Jonathan fashion, I listened but didn’t fully believe. After the last several months, I’m a believer: It’s the candidates, stupid!
I’ve talked to a number of professional Democrats about state politics. Every one of them admits the Democratic Party hasn’t made state politics a focus for more than a decade. This year was different, to say the least. I spoke with several candidates who told similar stories: they were catalyzed to get involved after Trump’s election, researched their Delegate, didn’t like what they learned, and committed to supporting his/her opponent – but an opponent never came, and so they decided to run themselves. Others were encouraged and trained by fantastic organizations like Run for Something, The Arena, and Emerge Virginia. In most of my conversations with political operatives on the importance of state politics, they would invariably mention “building the bench” of future national candidates. One thing I didn’t hear from any of the candidates I worked with in Virginia this cycle was ambition for higher office. That’s not to say none of them aspire to it, but rather their primary goal was to serve their communities and stand up for their values. And it worked!
The passion, authenticity, and commitment of these candidates was palpable to everyone they encountered. As someone helping get their respective messages to constituents online, I got to learn their stories and hear them speak on the issues important to their communities. And frankly, it made our job relatively easy – no need to massage it or punch it up, just get their already compelling message to as many voters as possible.
So with all that said, it is my great pleasure to share some of their inspiring stories with you (bold denotes winner; * denotes incumbent):
2017: D 62.59% (12,544) – R 37.26% (7,469)
2015: D 49.35% (5,714) – R 50.43% (5,839)
2013: D 50.56% (8,189) – R 49.18% (7,966)
Jennifer is truly a force of nature and an inspiration. When people talk about living a life of service, she is what they mean. Jennifer is foster mother, a public defender, and was one of the first women (let alone women of color) to graduate from the Virginia Military Academy. We worked very hard to make sure everyone in her district knew that part of her story. What very few knew until recently is that Jenn is also a new mom to twins who were born premature during her primary campaign (oh yeah, she wasn’t even the favored nominee) and spent the entire general election campaign in the NICU. The thought of her going to visit her sons in the hospital every night after a long day of campaigning brings me to tears every time (including while typing this).
Wendy’s story also makes me cry. She’s a working mom who responded to Trump’s election by founding an Indivisible chapter in her Republican county. She attended a town hall for her Delegate and asked him pointed questions about his positions, especially on gerrymandering. When she went home and found that his voting record didn’t match with his answers at the town hall, she decided to support his opponent…and you know the rest. Wendy also endured great personal tragedy early in her campaign when her brother – who had struggled with addiction and mental illness, and had been denied Medicaid multiple times – passed away. Instead of doing what most of us would have done and take time to grieve, Wendy rededicated herself in her brother’s honor to her campaign to unseat a man who had repeatedly voted to deny Medicaid expansion to her brother and 400,000 Virginians.
2017: D 54.33% (12,478) – R* 45.52% (10,454)
2015: D 41.55% (6,587) – R* 58.31% (9,245)
2013: D 47.42% (8,650) – R* 52.31% (9,541)
I didn’t work directly with the Hurst campaign, but I got to know his story indirectly through the work Tech for Campaigns did with them. The murder of his fiancée was national news and political inaction on gun violence catalyzed Chris to run. His district has nearly 30,000 college students, yet no Democratic candidate has successfully appealed to them in the past. Chris was able to break through and get 144% (!!!) of the vote total as the Democrat in the last similar election (2013).
2017: D 53.94% (11,888) – R* 45.66% (10,064)
2015: D 43.86% (5,592) – R* 56.05% (7,147)
2013: D 48.47% (8,448) – R* 51.33% (8,946)
As the nation’s first openly transgender state legislator who unseated the sponsor of Virginia’s transphobic bathroom bill, Danica’s story is already national news – and deservedly so. Tech for Campaigns didn’t work with her campaign, but I was told of the many hateful things her opponent did throughout the campaign, including constantly misgendering her. She routed an incumbent who had been in office since 1991 (!!!), and she also wins my vote for the classiest response to hate in this election:
When asked about Bob Marshall, Danica Roem said “I don't attack my constituents. Bob is my constituent now.”
2017: D 49.78% (14,323) – R* 50.21% (14,447) 2015: D 41.40% (7,472) – R* 58.46% (10,551) 2013: D N/A – R* Unopposed
Larry Barnett is just an amazingly nice guy who truly cares about his community. The first phone call I was on with him left me feeling like I’d known him for years. He has spent over 30 years working in his county’s department of Mental Health Support Services and volunteers his time to train local first responders in coping with crises. Medicaid expansion and mental health/addiction were cornerstones of his inspiring campaign against a 3-term Republican incumbent (uncontested twice), who had voted against Medicaid expansion and sponsored a bill to conceal the toxic chemicals used in fracking from FOIA requests. Despite being such a longshot that even the Governor’s race didn’t spend any time in his district, Larry nearly doubled the vote total of the last Democrat to run in the district and came within 124 votes of victory.
2017: D 53.55% (14,907) – R* 44.62% (12,420) 2015: D 46.54% (8,287) – R* 53.38% (9,506) 2013: D 49.40% (11,280) – R* 50.40% (11,508)
Elizabeth Guzman is a naturalized citizen originally from Peru, who became one of the first two Latina Virginia Delegates (along with Hala Ayala). She came to the US as a single mom with her daughter, and initially struggled to keep a roof over their heads. But through her intelligence and harder work than I can even imagine, Elizabeth earned not only her college degree but then 2 Masters degrees and created the comfortable middle-class American life she had dreamed of for her family. Not content to merely enjoy her success, Elizabeth dedicated her career to helping others as a social worker and active volunteer in her community. She defeated a Republican incumbent who had held office since 2002 (!!!) and sent campaign mail accusing Elizabeth of supporting illegal aliens being able to buy guns.
2017: D 58.48% (17,850) – R* 41.41% (12,639) 2015: D 46.86% (8,596) – R* 53.06% (9,734) 2013: D N/A – R* Unopposed
This is another campaign that I didn’t work with directly but know of through the work Tech for Campaigns did for them. David came from rural poverty and was raised in a state-run group home and foster care. He became the first member of his family to attend college and rose to the rank of Commander in the Navy before retiring and becoming a successful entrepreneur. Even with all the odds David beat, he credits his success to the help he received along the way and is committed to giving back and creating opportunities to follow him. He crushed a 4-term Republican incumbent (uncontested once) and more than doubled the vote total of the last Democrat to run in the district.
2017: D 50.74% (11,832) – R 49.05% (11,438) 2017 (Special Election): D 47.05% (2,939) – R 52.76% (3,301) 2015: D N/A – R* Unopposed 2013: D N/A – R Unopposed
Cheryl has been a local high-school science teacher for 24 years, currently teaching AP Environmental Science. Virginia Beach is ground-zero for climate change, yet her opponent – who received over $200k from the Republican party – voted to make Virginia more appealing for fracking. He was also an ally of for-profit schools and an opponent of women’s reproductive rights, who proudly campaigned on his vote to commemorate the Day of Tears when Virginians are encouraged to fly their flags at half-mast on the anniversary of Roe v Wade.
Immense credit goes to the countless volunteers (especially the amazing Tech for Campaigns teams that worked on these campaigns), outside organizations, tireless campaign staff, and of course the voters of Virginia who truly answered the call yesterday (even in the rain!). But my amateur opinion is it all starts with the candidate and their ability to relate and inspire.
If you think activism doesn't matter and that we can't fix what we believe is broken, just take a look at the Democrat, female, Latina, transgender, African-American and Sikh officials newly elected across our country today. Keep fighting. Election 2018 is one year away.
I wish our country wasn’t where it is right now, and I know the immense and in some cases irreparable harm this administration is causing many of our friends and neighbors. But if this is what it takes to motivate honorable and altruistic people to run for office again – up and down the ballot, then that’s at least a silver-lining. And it’s the clearest path I know back to the place this country should be.
I leave you with this victory speech by Jennifer Carroll Foy:
Ted Rheingold is the most inspiring person I have the honor of knowing. I’ve thought about it quite a bit these last 24 hrs, and the superlative is appropriate.
Ted’s power to inspire is his normalcy – he isn’t Elon Musk or Mark Zuckerberg – Ted is just like us in that he hasn’t had that life-changing exit or been catapulted to celebrity status. But unlike many of us, Ted has truly lived his life for others, and it’s brought him a level of love, respect, and admiration that no amount of money could ever buy.
Last year, I got roped into fighting in a charity boxing match shortly after Ted shared his diagnosis. I needed to pick a charity to raise money for and I wanted to dedicate my fight to Ted. So I texted him to explain the situation and ask for what charity he’d like me to raise money. I was expecting an organization doing research that could help treat him, or maybe a fund for the hospital where he was receiving treatment, or maybe the American Cancer Society. I guess I shouldn’t have been surprised when he responded with a list of organizations helping the homeless in the Bay Area, because it was typical Ted – even in his darkest days, thinking of others first.
He never said it, but I understood from our text conversation that he didn’t want a fundraiser in his name. He and I decided on a great organization called Lava Mae, which provides showers to homeless people. And thanks to Ted’s help promoting the fundraiser and the generosity of some amazing people, we raised $2,825 for them. As always, Ted eschewed the spotlight and did the actual work of helping people.
I have learned so much from Ted and he has been essential to my transition to a purpose-driven career path. I know I’m one of many who have been graced by Ted’s boundless generosity in advice, introductions, and discussions. And I’m sure they agree it’s impossible to overstate the value of Ted’s counsel in work and in life.
When he first got sick, I asked Ted how I could help and he told me to send him photos of pretty flowers. So I started paying more attention as I walked around and Tweeting photos to Ted of flowers that caught my eye. As with everything else, this was as much something for me as it was for Ted. He gave me the gift of opening my eyes to the everyday beauty that surrounds us. And it’s a habit I don’t plan to give up.
Life is so fucking unfair! Horrible tragic things happen to the best people. #EnjoyEveryDay and fight for justice at every opportunity. ❤️
I am eternally grateful for everything Ted has given me and to have a constant reminder of Ted and his lessons in my son, Teddy. When I told Ted about our son’s name shortly after he was born last year, I explained that his legal name isn’t actually Ted or Theodore but we just decided to call him Teddy because we like it. To which Ted replied that his name isn’t actually Ted either and his parents did the same thing as us. Elizabeth and I couldn’t imagine a better person to be an unintentional namesake for our son.
I texted Ted 2 weeks ago when I was coming to San Francisco for the day to see if he was up for a visit. He told me it was Mabel’s first day of school and he wasn’t making any other plans that day – that was our last conversation. Ted’s love for Molly and Mabel is infinite, and my heart is so broken for their unimaginable loss. Knowing Ted, I believe leaving them was probably the only thing with which he couldn’t make peace.
May we all strive to be as kind and brave and wonderful as Ted and to live by his example and words:
Per usual, gifts in Ted’s honor are for us all:
My husband @tedr was a king among men. He made the world better. Consider a donation in the name of Ted Rheingold https://t.co/6MG0HjPGeO
Imagine a reality in which the first female president succeeded the first African-American president. Imagine a reality with taco trucks on every corner, without an administration pushing every legal and ethical boundary, without our global standing diminished, without the mass undoing of years of progress in criminal justice reform, financial regulation, and protecting the environment, without ICE agents ripping apart families, without White Supremacists emboldened enough to march by the thousands in Charlottesville. That sounds like a much better world to me.
But that world probably is also missing the incredible counter-protest that happened in Boston yesterday, the beautiful response from the community of Charlottesville, multiple Presidential Commissions resigning en masse, GoDaddy, Google, Zoho, Cloudflare, and Namecheap banning the Daily Stormer from their respective services, James Damore having the chutzpah to write that memo prompting a much needed acknowledgement of discriminatory beliefs within the tech community. In that reality, people speaking out against hate would probably still be derided as “Social Justice Warriors” and those of us who weren’t direct objects of discrimination could still plausibly deny how widespread it continues to be.
That reality may sound better, but this is the one we needed to truly make progress as a society and a nation.
With the benefit of current events, it’s impossible to ignore that hate and prejudice are deeply rooted in a much larger percentage of our fellow citizens than many of us (by virtue of our privilege to not be discriminated against) believed just a few months ago. As President Obama said recently of his election in 2008:
“I think some, you know, white voters, who sincerely were glad to see that the country had made this breakthrough, there was also made an unrealistic notion that somehow, ‘Okay, that means discrimination’s over.’”
But the truth is the discrimination, both systemic and individual, has always been there. And as long as we were having a debate about whether or not it was still an issue, we couldn’t have the much more pressing debate about how to truly irradicate it. As long as we wanted to believe that every case of police killing people of color, of sexual discrimination or assault, of homo- or transphobic rhetoric or legislation were isolated incidents and not part of a broader pattern, we were delegitimizing the lived experience of every one of our fellow citizens not born into our same privilege. We were also giving cover to the metastasis of “the Alt Right,” “Ethno Nationalism,” or whatever other normalizing euphemisms we’ve allowed White Supremacists to rebrand themselves as.
Everything horrible and regressive that has come from Trump’s election, which includes preventable deaths and other irreparable harm that cannot be trivialized, can be the foundation of much more meaningful progress if we answer the call. Hatred and prejudice derive their power from silence and fear in the rest of us, from the myth that they are the “silent majority.” And while it saddens me to now have proof that 1/3 of our country are actively or tacitly racist, I’m pretty good at math and that means there are still twice as many of the rest of us than there are of them.
Let us continue to raise our voices to show them to be the vocal minority they really are and to drown out their message of hate with our embrace of love, equality, and justice.
President Trump has just announced the United States will withdraw from the Paris climate accords against the advice of the entire global scientific community, much of the American business community, and even many of his own advisors. There has been no shortage of ink spilled analyzing why 63M Americans – mostly white, less educated, and non-urban – voted for Trump, and the (somewhat patronizing) consensus of the left is some combination of outright racism, fear/anger, and deception. But what about the Trump supporters and enablers who haven’t been hoodwinked, who have no reason to be blinded by rage, and who likely know firsthand much worse behavior than we have observed from the outside?
What motivates the Republican politicians that endorsed (and now shield) Trump and the large conservative donors that continue to tacitly if not explicitly condone his actions? These are largely educated, wealthy, urban elites – exactly the same type of people they have mobilized millions of Americans to despise. What explains this schism among the “elites” who, unlike most of the country, share both a clear-eyed understanding of the consequences of Trump’s actions and huge financial incentives to support them? If the most fundamental human motivators are fear and greed, why do identical circumstances inspire greed in conservative elites and fear in liberal elites?
Coastal elites thank U for surrendering your family's healthcare to cover tax cuts, even if you only did it out of spite. Enjoy the buffet.
— Downtown Josh Brown (@ReformedBroker) May 24, 2017
Staggering irony that rural conservative Trump Voters are giving up health care so rich urban liberals like me can get a huge tax cut.
It’s not that the liberal elites have embraced and benefited from free-market capitalism any less – WarrenBuffett, Michael Bloomberg, George Soros, Tom Steyer, Chris Sacca, Mark Cuban, Reed Hastings, and Reid Hoffman among many many others opposing regressive conservative policies are some of the most ambitious and successful businesspeople of our time. And it’s not that the conservative elites have less to lose from potential longterm environmental and/or social catastrophe – the Koch brothers and Robert Mercer have children and grandchildren that will long outlive them, as must many of the 700 donors that contribute >$100k per year to the Koch’s conservative political organization.
I believe the answer lies in a key passage of the Trump administration’s recent WSJ editorial:
The president embarked on his first foreign trip with a clear-eyed outlook that the world is not a “global community” but an arena where nations, nongovernmental actors, and businesses engage and compete for advantage.
This is an unambiguous statement of their zero-sum worldview – in order for us to win, someone else has to lose. In the Internet age, this is widely considered to be an archaic approach to business that opens incumbents to disruption from startups seeking to “grow the pie” rather than fight a war of attrition. It is also at the heart of the divide between conservative and progressive mindsets. By definition, conservatives believe this is as good as it gets (or, worse, that our best days are behind us) and we must defend the status quo against the future (or attempt to reclaim the past). Whereas progressives inherently believe the future should be better than the past, that innovation can empower us to create a tomorrow superior to today.
So is the difference between the conservative and liberal elites that for some reason one group is driven by greed and the other is more altruistic? No, both are greedy otherwise they wouldn’t be millionaires and billionaires. But, to borrow a distinction first made by Gus Levy when he was head of Goldman Sachs (of all places), conservative elites are “short-term greedy” while liberal elites are “long-term greedy.” Those who are happy to pay more taxes than the direct government benefits they receive are rejecting the zero-sum worldview and embracing the progressive mindset that their investment in public goods* can deliver a better future for themselves than they could achieve just by hoarding their wealth.
This enlightened self-interest is fundamental to the American experiment, as observed by Alexis de Tocqueville nearly two centuries ago. And if we let our country become one governed by the zero-sum worldview, we will lose everything that has made it great.
* A common conservative objection to investment in public goods is that government is inefficient and free-market solutions are superior. This is a disingenuous argument, because the free-market will never provide for many public goods necessary to a well-functioning society (even Hayek agrees). So yes, government is inefficient and can be greatly improved but that does not obviate our need for it.
I don’t discuss politics on the Internet. This is different. This is my small strike back against the evil that manifested in Paris last night.
I’m generally dismissive of social media activism for often over-simplifying discussions of complex issues into us vs. them shouting matches. This is different. This is very much an us vs. them shouting match, in which we are members of a multi-cultural global civil society and they are zealots who want to start an “apocalyptic ‘war of civilizations.'”
I share the belief that the goal of the Paris attacks is to eliminate the “grayzone” of Moderate Islam by triggering Islamophobic backlash in the non-Islamic world. It is the same goal of the other recent atrocities attributed to the self-proclaimed Islamic State: the bombings in Beirut; the downing of the Russian airliner; the bombings in Ankara. These terrorists believe in a black and white conflict between Radical Islam and the entire rest of the world, and these attacks are their way to make that vision a reality.
This is our opportunity to fight back! Do not allow the perpetrators of these attacks to be proved right by our words and deeds, nor our inaction against the words and deeds of others, in response to their horrible acts of evil. This is a time when spreading messages of tolerance and love on social media actually can have an impact.
I stand with the majority of Muslims in the world, who are equally devastated by these attacks, to show the enemies of civilization that it is *all of us together* versus them.
By no means is this alone a panacea. These events have made clear that the threat from the self-proclaimed Islamic State is much bigger and closer than most of us had hoped. Unfortunately, the hard work and sacrifice required of government officials, diplomats, armed forces, and first responders all over the world may be far from over. But this is also a propaganda war being fought on our home turf, and those of us not in a position to take direct action IRL can make a difference with our voices online.
That there may be the last awe.sm pun I make on this blog, because today we’ve announced that Unified has acquired awe.sm!
Every opening line I originally came up with for this post was clichéd as hell (“proud to announce…”, “ending one chapter, beginning a new one…”, etc). I guess the reason why these posts are so full of clichés is that it’s common to express a lot of the same emotions in these circumstances:
Pride – It’s impossible not to be nostalgic at a time like this. Just 5 years ago, awe.sm was little more than whiteboard sketches and notes on napkins. I once read a great blog post about the importance of celebrating the small victories in a startup. And when you add up all those victories – from every incredible hire, to the customer wins, to the amazing investors who backed us – this moment is the culmination of all the fantastic and gratifying moments that have led to it.
Excitement – Unified is an extremely impressive company. As a first-time entrepreneur, I appreciate all too well the value of the experienced leadership team Unified has in Sheldon, Jason, and Calvin. In our conversations with Unified, there were 3 specific things that convinced me this deal was the best way to take what we had built to the next level:
Their understanding of and appreciation for the power of the technology we’ve developed at awe.sm;
Their proven sales and marketing machine running at full speed as we were just assembling ours; and
What sealed the deal for me was talking with David and Jeff, co-founders of PageLever which was acquired by Unified last year. Over a year after the acquisition, the PageLever technology and team are flourishing inside Unified and that is a big part of the reason we think it’s a great home for awe.sm.
Gratitude – I am most proud of and grateful to the world-class team we assembled. Not only because of their amazing talent and commitment but because of the incredible (and incredibly enjoyable) culture they created. To Laurie, Jeremiah, Bennett, Jonathan, Randal, Tim, Beth, Mason, Tilly, Andrew, Cole, Bryon, Johnny, Curtis, Ginevra, Jeremy, and Fred, thank you for everything you’ve done to make awe.sm so much more than I could have ever imagined! I am still in awe of the investors who have supported us in every possible way on this sometimes bumpy road: Mark Suster @ Upfront Ventures; Jerry Neumann @ Neu Venture Capital (best VC site evar!); Jennifer Lum & Peter Wernau @ Apricot Capital; Taylor Davidson & Darren Herman @ kbs+ Ventures; Howard Lindzon & Tom Peterson @ Social Leverage; and Ryan McIntyre @ Foundry Group. Finally, I want to thank every awe.sm customer for trusting us and helping us improve every day. One of the key reasons we’re doing this deal is that we believe we can deliver you even better products and services as part of Unified, and we’re excited to dig in and start showing you what we can do together. As always, you can reach us at support [at] awe.sm with any questions or feedback.
I am very happy to announce that Fred McIntyre has joined awe.sm, the company I founded and have led for the last 4 years, as CEO (read more about it on TechCrunch). My new role is Head of Product Development in which I will continue to lead product, strategy, and engineering.
This is at once one of the hardest and best things I’ve ever done.
There’s a lot of great writing out there on hiring non-founder CEOs from a business perspective: if you don’t want to have to do it, do these things (I definitely didn’t do enough of them); if you think you might need to do it, think about these things; and if you’re going to do it, try to do it like this. So what I really want to talk about is the personal side of this process from my perspective as the founding CEO.
I wish I could say this was my idea, but frankly I wasn’t self-aware enough to come up with it. To be an entrepreneur I believe one must have a somewhat irrational belief in your own capabilities, otherwise you’d never be dumb enough to start a company. Regardless of any perceived glamor, most entrepreneurs I know will tell you that starting and running a company is fucking hard and there’s often more misery than joy. But there’s just something broken in us that makes the prospect of doing anything else seem even worse. For those of us with this particular defect, I think the Peace Corps slogan sums it up: entrepreneurship is “the toughest job you’ll ever love.” The thing in me that drove me to quit my job, move in with my parents, and start awe.sm is the same thing that kept me going through incredible stress and the lowest of lows to make it to our Series A and it’s the same thing that kept me from asking for the help it was clear to everyone around me that I needed.
I put hiring a CEO in the same category as taking an acqui-hire or just closing up shop and moving on — things I would think about at 4am in the office on those darkest nights when I’d have a bout of sobriety about the insanity I’d turned my life into. And ultimately, things that represented the one unacceptable option motivating me to push even further beyond my limits I’d long surpassed: failure. In the early days, the only way for me to keep awe.sm from failing was to tie my fate with the company’s. If awe.sm failed, I failed. But as we switched from lean startup to growth company, I didn’t fully realize how making my ego a shareholder went from being necessary for survival to being a limitation on what we could achieve.
Fortunately, I have an amazing Board that cares about me as a person as well as an investment. Mark, Ian, and Ryan took the time to help me see why something needed to change, and, to their great credit, gave me the decision of what to do. I will never forget the emotional tornado (roller-coaster doesn’t do it justice) of that day. After 3 and a half years of fusing my self-worth with the success of the company in the crucible of startup survival, it was impossible to tear them apart without pain. But while my first reaction was disappointment and failure, it was almost immediately washed away by a wave of relief. I knew everything they were saying was true, arguably better than they did, and I knew change was inevitable, but I had no idea how stressful and exhausting maintaining my internal reality distortion field had been until they gave me permission to turn it off.
The basic choice we had in front of us was to sell the company or hire a CEO. We had plenty of money in the bank, a great engineering team in an impossible hiring market, and real valuable hard-to-build technology, so we were in a better position for a sale than many acqui-hires. Personally, I still owned 30% of the company outright and selling would have kept me from having to give up the CEO role. On the flip-side, we would be starting from scratch on the CEO search and it would ultimately mean signing up for a Series B (i.e. more dilution) and several more years of awe.sm. The Board said they would support either decision, but only I could make it. Talk about a gut-check!
Guess which one I picked :-). It was far from an easy decision, I agonized over it for weeks and got advice from a lot of smart and experienced people (thanks everyone!). I made the choice and told the Board; they asked me if I was sure and I told them I was; I had second thoughts and talked about it with a bunch more people; the Board asked me again if I was sure, I said I wasn’t but I was committed. And all this was before we even started recruiting a CEO! I ran the search process, screened all the candidates, and ultimately had the final say on who we hired.
I chose not to sell because I believe the opportunity for awe.sm is too big to ignore, and I chose Fred because he shares that belief. When Fred accepted his offer, Mark Suster said that he thought this would be the best year of my career. I hope he’s right, but I’m at least certain it will be the best year of my life since starting the company.
Spear phishing is an extremely potent hacking vector that combines social engineering with phishing. Basically, an attacker tries to learn enough about a specific victim to inform the design of a fake email that the victim is more likely to think is legitimate and thus open and engage with. For a detailed example of spear phishing in action, see this account of how the Onion’s Twitter account was hacked.
Standard phishing is generally thought of as a brute force attack in which the attacker crafts fake emails meant to fool the broadest set of people possible (e.g., you’re much more likely to see a phishing email claiming to be from a large national bank, like Chase or Bank of America, than a small regional bank). Whereas spear phishing has conventionally been viewed as a more bespoke approach that is targeted at a specific individual or organization. So the current conventional wisdom is that normal phishing attacks are relatively easy to spot, and only relatively sophisticated attackers going after high-value targets, like access to government or corporate systems, use spear phishing. But what if that’s changing?
Over the last several months, I have been the target of what might be a new, more scalable, approach to spear phishing. I have been receiving phishing emails that are sent using the names of people I know but not their email addresses (see below).
I was at first confused at how the attackers were coming up with these names. My first fear was that they had hacked my email account and thus had access to my address book, but I have 2-step verification enabled and I didn’t see any suspicious access in the Last account activity.
Then as I was looking through my spam folder this week, I noticed a pattern: the names being used were all people who had recently commented on my Facebook posts. This is just a hypothesis and there’s a lot I still don’t understand about the attack, like how they associated my email address with my Facebook profile, how they are scraping the comments on my Facebook posts, and most of all why they would target me.
But if in fact they are scraping Facebook activity to come up with the names to use as senders, this opens up a much more scalable (and thus dangerous) vector for spear phishing. I’m very curious to hear if anyone else has experienced similar attacks and/or has any other information to add.
Last month, I had the honor of participating in the inaugural Foundry Group portfolio CEO summit where we had an enlightening discussion on leadership. To kick-off the conversation, one of the other CEOs volunteered the story of a time he felt he failed as a leader: he had a disagreement with some of the engineers on his team about the complexity of a given feature; and when their conversations reached an impasse, he took matters into his own hands and coded the feature himself.
I found the most interesting part of the ensuing discussion to be the disagreement over whether this CEO’s act of digging in and coding the feature himself was a leadership success or failure. We didn’t do a formal survey, but the group appeared to be divided into two camps: one that felt he should have focused on solving the communication and process (and possibly staffing) issues that prevented his team from executing as he desired; and the other that saw value in the example he set by showing he was capable of and prepared to do what he asked of others.
Earlier this week I read Zach Bruhnke’s excellent post You’re not the CEO – you’re the Fucking Janitor, and it took my mind back to that discussion about what good leadership looks like in a startup. My answer: it depends. It seemed to me that the folks at the summit who felt this CEO failed by doing instead of managing were leaders of more mature companies, while the ones who admired his leadership by example tended to be running earlier stage startups. As someone running a company that had recently raised our Series A and was growing from a team of 5 in January to 14 today, I found myself agreeing with both sides of the debate.
For a boot-strapped or even seed-funded startup, I think Zach’s post is spot on. The “CEO” in Zach’s story is a total douche, and my business cards say “Co-founder” precisely because calling myself the Chief Executive over 4 of my friends made me think of Yertle the Turtle. My dad always told me “the fish stinks from the head”, which is just his graphic way of saying great leaders lead by example. In my relatively short leadership career thus far, I’ve taken this to heart and always jump at the opportunity to do things myself.
In addition to the mutual respect and motivation Zach mentions in his post, one of the greatest advantages I’ve found in this approach is the intimate understanding a leader attains of how things are done within their team. Across the many failures of leadership I’ve observed (I was at Yahoo! for 4 years 😉 ), there’s a recurring theme of the leader being too removed from the actual doing. Especially in the technology world, the means of production can be just as important as the output. I can’t tell you the number of product and business leaders I’ve dealt with who treat engineering like a commodity instead of a potential competitive advantage. You only need to look to the world’s most valuable company to see what great supply chain management (i.e. caring how the sausage gets made) can do for your business. And when you’re a software company, every architectural decision your team makes has a bearing on essential business considerations like performance, reliability, time-to-market, and agility in responding to new threats and opportunities. That’s why awe.sm is, above all else, an engineering-driven organization (and looking for even more great engineers 🙂 ).
Never trust a "startup" CEO who doesn't know how their product is built.
But in a later stage company, the leadership challenge is greater because you need to figure out more scalable ways of achieving these same goals. There was one particular line of Zach’s post that stuck out for me in this regard:
If you want to be a CEO in the sense that you dream of then you should remember to be the Fucking Janitor too.
A couple months after raising our Series A, I was washing dishes in the office and caught myself feeling self-satisfied because here I was, CEO of a company that had just raised millions of dollars, doing the dishes. I thought about my dad’s smelly fish saying and how he’d be proud of me. Then I thought about our investors and what they’d think of this…and it struck me they’d be pissed. Here I was, CEO of a company in which they’d just invested millions of dollars, doing the dishes instead of the dozens of other things only I could be doing to make their investment successful.
In the few months since then, my leadership focus has shifted. I still do the dishes when it’s my turn; when AWS shits the bed at some inhuman hour, I’m in our IRC room doing what little I can to help; and I always want to understand the gory details about why we made one architectural decision over another even if I wouldn’t know how to implement either of them myself. I am proud to continue to be a colleague to my team above all else. But leadership in a larger organization requires more than that. Our goal is to achieve on a scale bigger than what one person can achieve alone, and that means the leader needs to lead not just do. Doing is good, but when it turns you into a micro-manager or takes you away from leading, it can be counter-productive.
Delegation is hard. I’m finding delegating well to be much more challenging than doing things myself. Leading purely by example just requires effort and a willingness to do things that aren’t fun or glamorous, and as the leader you’re usually the most incentivized to get those things done. But effective delegation requires much more than mere will, it is a skill set developed with patience and learning and painful trial and error. It requires finding great people, training them in the skills you need them to have, motivating them to share your goals, empowering them with the resources and information to be successful, trusting them to do their jobs, and then giving them feedback on how to improve. I have come to believe my primary job as a leader is to enable the members of our team to deliver what the company needs from them, and that’s a lot harder and even less glamorous than being the Fucking Janitor.
