Tough Love

At the beginning of my junior year of high school my English teacher, Dorothy Palme, gave me a D minus on a paper I wrote. It was the first grade below a B I had received in my entire academic career. I was flabbergasted and livid. I stayed after class to ask her why she gave me the grade and she walked through all the reasons. What it boiled down to was that I was a poor writer. I left the classroom even angrier after getting the feedback. Like the little brat I was, I brought the paper home to my parents and exclaimed that I had been cheated. They read the paper and I’ll never forget their reaction. They unanimously supported Mrs. Palme’s assessment that I couldn’t write worth a damn. They said so themselves and I knew they were a combination of disappointed and embarrassed.

Mrs. Palme was the best teacher I ever had. Over the course of the year, she worked with me to transform the way I approached writing. She taught me about introductory prepositional phrases, how and when to appropriately use adverbs, how to coherently structure my thoughts, and so much more. She did it all on her own time outside of class, too. Her lessons will stay with me forever and it’s not hyperbolic to say that she changed my life for the better.

Most teachers would have played it safe. Perhaps they would have graded the paper a B minus or a C. But Mrs. Palme wanted to teach me a lesson – that I could and must do better. It was a lesson that required her to be brutally honest, and to roll up her sleeves and take the time to help me if I wanted to fix it. And while I hated the lesson in the moment, it fondly sticks with me to this day.

The Mrs. Palme’s of the world are far and few between. Over the course of my professional career, I haven’t encountered a lot of people who had the courage to tell me how it is. There are two investors and board members I’ve worked with that particularly stand out: David Weiden and Scott Feldman. David once lambasted me for not truly understanding basic concepts around unit economics like payback periods. And Scott once vehemently claimed that I was in the process of running my business into the ground because I was being a poor steward of capital. Both took the time to explain what they meant to me, connected me with people that could help, and also did the hard work of helping me themselves.

When it comes to investors, David and Scott are the exception to the rule. Most egregiously pander to entrepreneurs. For many, telling the brutally honest truth doesn’t have any upside. Why rock the boat and develop a reputation with founders as being the mean investor, especially in the hyper-competitive of the past decade? So much emphasis is placed on supporting entrepreneurs and being “founder friendly” that it’s nearly impossible for most operators to get to the truth.*

The irony is that withholding the truth is the opposite of being founder friendly. There is a market for those who can do this exceptionally well. It’s something I try to do when I invest in companies and work with founders. And to my delight, it’s not just me who appreciates “real-talk.” Entrepreneurs crave it. They may hate it in the moment because it can hurt the ego, but it resonates. When it comes to company building, I want to partner with someone who tells it how it is and isn’t afraid to hurt my feelings than someone who prioritizes simply being liked. In my experience it’s those that dish out the tough love that I’ve grown closest to and admire most.

*The counterpoint to this is that a majority of VCs are terrible at giving feedback, are bad at what they do, have zero compelling or relevant operational experience, and their hands-on involvement is oftentimes destructive. Choose your partners wisely or suffer the deleterious consequences.

Dear Republican Friends

I have been trying my best to have an open mind when it comes to politics and worldviews. I try to understand and question my biases so I can feel confident that my opinions and beliefs are informed ones. I consider my political orientation Left/Progressive. I don’t agree with all Democrat policy. I think most politicians, regardless of party, are inept and care more about preserving power and their jobs than they do legislating. But I do believe that the government can be a remarkably effective tool to make Progress and help people.

As part of my quest to have a more comprehensive and empathetic understanding of people’s political inclinations, I follow a lot of Republicans that I think are very intelligent and successful people. I try to learn about what is most important to them, politically speaking. The common denominator seems to be fiscal policy.

I understand that people don’t like taxes.

I understand that people don’t like it when the government spends lots of money.

I understand why people think the federal government is bloated and ineffective.

I understand why people don’t like their business regulated.

I understand why people are vocal about these issues. But I do not understand your silence when children are regularly massacred in schools in this country. It’s a preventable epidemic and it does not happen anywhere else. And like it or not, this is a political issue.

Is this not your line? And if it isn’t, do you have one? When is enough enough?

Asking for my children and yours.

Constraints and White-Hot Risks

I recently read The Power Law by Sebastian Mallaby. There is a section about how Thomas Perkins, the founder of Kleiner Perkins, approached venture capital. His strategy was to “identify the white-hot risks, then find the cheapest way of going after them.” Essentially, determine where the startup might fail (e.g. is there a foundational technical breakthrough that’s required? Some complex operational execution? A question of market demand? etc.), and maniacally focus on solving for that singular element in the most economically efficient way possible. I very much like this approach to investing and company building. Constraints (i.e. the limited amount of money one has in the bank) force focus and ruthless prioritization.

In the past decade tech entrepreneurs have experienced remarkable market conditions. Money from venture capitalists was seemingly infinite. This created a series of bad behaviors that entrepreneurs will have to unlearn. Mainly, it enabled founders to do too much shit at once without truly understanding and focusing on what was most important to make their business actually work (i.e. what is the white-hot risk?). My strong preference for company building, particularly at the early stages, is to singularly focus on the thing that is mission critical and to tackle that in the scrappiest way possible. I, like every other entrepreneur, have made the mistake of trying to do way too much on more than one occasion. The times things worked best were always when we had a crystal clear focus on the absolute most important thing to accomplish and focused all of our resources and attention towards it.

The recent market turn is going to create new constraints for entrepreneurs. Capital will be much harder to come by, and this will be a forcing function for leaders to do less. Ultimately, I think this is a very good thing. Many founders will struggle to adapt – these are new market conditions for a lot of people and new is always difficult. But those that do embrace these newfound constraints and zealously hone in on the white-hot risks are going to emerge having built industry-defining iconic companies. They will likely build better companies faster in this capital-scarce market than they would have in the capital-abundant one. Call me old-fashioned, but I’m excited about this return to normalcy. In the long run I think it will produce better outcomes for everyone in the ecosystem.

Indestructible Product Market Fit

I left GroupMe/MSFT at the end of 2013. I haven’t been involved with it for a long while now, but around a year ago I caught up with someone who was familiar with how the product was doing inside Microsoft. I was absolutely shocked to learn how popular the app still is. There were roughly 25M MAU, nearly 100m total users, and 13m DAU. Practically every college student in the country uses it. And roughly 10 engineers were supporting the entire operation.

I was shocked because the product hasn’t really evolved in the past decade. There are seldom any updates, and it has really just been in maintenance mode. It’s an incredible asset that for some reason has not been usurped by competitive messengers. It’s sticky. And fun #)

When people ask me about my GroupMe experience I like to say that building something in consumer is 90% luck and 10% executing against that luck. I actually think the luck variable for success in social may actually be closer to 95%. So many amazing teams tackle problems in social but their products never make it and if they do they’re usually a blip – they pop and then fizzle with no staying power.

Another thing I believe about consumer applications that make it is that they capture lightning in a bottle, and there is very little a team can do to fuck things up. Once the lighting is captured, even if you try to deliberately sabotage the thing, you can’t prevent it from growing. We sold GroupMe to Skype, and from what I’m told this was absolutely the case at Skype early on. It was a mess, but that product was going to catch fire no matter how dysfunctional things were. Twitter was the same way. And when I joined tumblr, there was very little the team could do to prevent its success. Constant downtime was never a deterrent. When you strike the chord it’s nearly impossible to dampen the vibration.

This isn’t to say that the early teams behind these companies were not good or deserving. They were. It’s hard to build new things and that alone is a feat. But it is to say that luck is critical, and that when you tap into something powerful it assumes a life of its own that you really can’t control. That’s the beauty of social. When something works, it really works. It’s the one place where product market fit means that even if you try, you cannot destroy your creation.

Musical Group Improvisation

Marc Rebillet is one of my favorite new artists I discovered in the past several years. His energy is infectious, he exudes nothing but positive vibes and fun, and he’s a musical improvisational genius. Normally he does solo live shows that he streams on YouTube (you can check them out here) where he messes around for an hour wearing nothing but a robe and some boxer briefs. It’s quite a shtick to say the least. But where he really begins to shine is when he improvises with other talented musicians. The first time I really saw this was in this video of him, Reggie Watts, and Flying Lotus.

Earlier this week I stumbled on a new collaboration he did with Reggie Watts and Erykah Badu. It’s exceptional. If you want a taste for what it’s all about, start watching at the 17:50 mark (for around 10 minutes), and then again at the 34:30 mark.

I am a huge fan of musical improvisation. My favorite live bands, Phish and The Disco Biscuits, all focus on group improvisation. There’s something uniquely incredible about a group of people making something out of nothing, listening and riffing off one another, and having both the patience and courage to explore uncharted territories together. But when it works, when the group gives it enough time to breathe and evolve, something magical happens. Something spectacular is extemporaneously created out of absolutely nothing.

There are several things I love about this segment with Marc, Erykah and Reggie. First, they’re all remarkably talented musicians in their own right. Second, they are so authentically themselves. They give approximately zero fucks that there are cameras recording them. They just exist in the moment, bringing their uniqueness to the melting pot. And last, this really exemplifies the power of group improvisation. They begin with a prompt – a monkey shaped instrument that makes animal noises – and they fully embrace the weirdness, exploring the motif as they voyage across a whole slew of different musical genres. They’re patient and fearlessly explore where the moment takes them. For me, that’s the purest thing about music, and it’s the thing I enjoy the most about it. Because when it works, magic is real.