I have seen a lot of young first-time founders play it fast and loose in their fundraising processes the past several years. It’s been frothy times, so I think it brings out a lot of strange behavior. It got me thinking of when I was a young founder and the things I’d do, particularly one specific story that I tell people when I get asked “what not to do” when fundraising.
Back in 2010 Steve and I launched GroupMe to much fanfare. It got a lot of attention out the gate because we built it at the first TechCrunch Disrupt Hackathon in NYC and the press thought it was neat that something could be built in a night and actually work. It was a good story. We raised a round of financing really quickly ($850k on a $2.5m pre-money - those were the days!), and then immediately got more inbound interest from VCs as the service began to take off.
We were invited to demo some new features at TechCrunch Disrupt SF (here's some video footage I found) so we flew out to the west coast and took some investor meetings before our presentation. We thought our next round was going to be preempted by a16z or Sequoia. We had met with Alfred Lin several times and loved him (as most entrepreneurs do) and we took a meeting with Roelof Botha at Starbucks across from the convention center. Vinod Khosla walked in while we were pitching and we felt like royalty being showered in attention. We certainly thought we were hot shit. I was 23 years old.
We walked out of that meeting absolutely certain Sequoia was going to be our lead. We were a small team so everyone knew what was going on, and after the meeting they asked us how it went in our GroupMe group. “Sequoia wants it hard” was our response.
Fast forward two hours - Steve and I are onstage presenting some new groupme features. We pride ourselves on live demos. Our teammate Pat is driving the presentation and on the screen in front of the entire conference he opens up our team group chat for everyone to see: “Sequoia wants it hard.”
We had no idea. But the second we walked off stage Pat pulled us aside panicking saying, “Guys, we have a problem.” Our stomachs hit the floor. I am surprised neither of us puked. Our friend Matt in the audience sent us a text that just said, “Holy shit.”
Lucky for us, not many people saw it, and nobody made a fuss about it. We asked TechCrunch to pull the video of the demo and they politely obliged. We saw some Sequoia partners afterwards backstage and nothing was mentioned. I don't think they ever caught wind of it. Crisis narrowly averted.
So I was a young founder who played it fast and loose. We do dumb things. It’s okay, sometimes. And this is an example of something I tell founders not to do when fundraising.
My favorite part about this story is that Sequoia passed on investing in GroupMe and promptly invested in WhatsApp, a move that would net them billions of dollars and go down as one of the greatest investments in VC history. It turns out that Sequoia, in fact, did not want it hard.
I am so tired of the current political discourse and its inescapability.
I am tired of our two party system that is objectively failing us.
I am tired of being told what to think, what to say, what to believe, who to like, who to oppose, what is right, what is wrong, etc. It’s too much.
The Republican Party was dismantled with the arrival of Trump and MAGA. Now the Democratic Party, of which I have been a member of my entire voting life, is being dismantled by the far left which consists of socialists, communists, and people who seem to detest the very idea of America.
And I get it. Capitalism is failing people and exacerbating wealth inequality. It is leaving people behind. Our education, healthcare, and housing systems are failing people. Our leaders are failing people. The vibes are overwhelmingly negative, pushing people to the extremes and believing that the only solution is a strongman authoritarian country or one where the government embraces a version of socialism or communism.
This is not the way.
We need a new center—one that lifts the floor for everyone, evolves capitalism, and restores a sense of shared purpose.
Capitalism has been a gift to the world and it works marvelously well. But it needs to evolve in order for our democracy to flourish. We need to turn the best ideas from the margins into policy that works for the mainstream. The only way out is through.
As Garry Kasparov said, "We need to grow the pie for everyone, not dismantle the bakery." Or as the extremes would have it: have the government seize and operate the bakery and allocate everyone a fixed piece of pie, or detain or deport the immigrant baker.
I constantly find myself lamenting Trump and the rise of MAGA on the right or fearing the rise of socialism, communism and antisemitism on the left. I get angry about it. The anger is all consuming. And I end up spending more time stewing in it than thinking about a positive path forward. I believe a lot of people feel that way, too. It sucks. I am trying to change that.
Nearly a decade ago, a product manager told me about the phrase "Slow is smooth, smooth is fast." It's a military motto that refers to how elite forces traverse ground and infiltrate enemy lines. The premise is that a deliberate and highly coordinated series of interconnected movements is significantly more effective and fast than an all-out storm the battlefield approach. While the former seems to move at a relatively slow clip, it is actually meaningfully faster than any alternative because of its meticulous movement.
This concept can be applied to doing things inside a company. Working with other people and being highly aligned and moving as one is a smooth way to do things. The coordination costs may be high, but the motion is smooth, and when you look back at the end of the day it's a hell of a lot faster than people flailing independently at warp speed.
Stylistically, it's also applicable at the individual level. My son is dyslexic, and he has a tendency to read through text as quickly as possible. This sometimes results in him reading a word like "turn" as "run" which can completely change the meaning of a sentence to the point it is nonsensical. The thing I tell him is that slow is smooth and smooth is fast. It's easier, more effective, and leads to better comprehension if you just take a beat as you flow through things. It's a really hard thing to do when we are wired to run.
Yesterday, I read an incredible article called AI 2027. I highly recommend taking your time and reading it. It goes through a variety of different scenarios about how the development and integration of AI into our world can and will unfold over the next several years. It reads like science fiction, and any prognostication of this sort has a tinge of fantasy, but it certainly feels quite real (Josh Wolfe likes to say sci-fi is becoming sci-fact and I believe that to be true at an accelerating rate). The outcomes range from utopian to armageddon, and the thing that determines where on that spectrum we end up is how deliberate we are along the way.
Every incentive right now encourages foundational AI companies to move fast. There are a slew of domestic competitors that are vying for AI supremacy and raising tens of billions of dollars to build the latest and greatest models. They range from incumbents to extraordinarily important startups filled with the world's best researchers. There is also a geopolitical force where China is moving at an alarmingly fast clip, too. The country with the most advanced AI is the country with the most influence and ability to align the rest of the world to its goals and values. The stakes could not be higher, so the incentive is to rush and "win the race."
I also believe that an overwhelming majority of the country has no political home. We are governed by the extremes of each party, and those extremes, while they are ironically much more similar to one another than dissimilar, are splintering the USA and compromising our ability to create a better future for everyone.
And with the emergence of all this turmoil, I have never felt more patriotic than I do today. I love this country. It’s a big mess, but it is our mess. And I know our future can be bright.
But in order for that to happen we need to fix the way capitalism works and deliver results for the 99%, not just the 1%. We need to lift the floor for everyone. We need the wealthiest people and biggest companies, those who have benefited from and in many cases exploited capitalism most, paying more to lift the floor for everyone. It is in their long-term interest to do this. If they don't, there is a clear path from where we are today to the pitchforks coming out. History may not repeat itself but it surely rhymes.
In our lifetime we have the unique opportunity to lift the floor for everyone, not create artificial ceilings. This is the best way forward, and we can do a lot of things that people in both parties want and need:
Make the cost of living and housing affordable by increasing supply
Create an exceptional education system with personalized learning for every child
Provide remarkable, cheap (or free), and personalized healthcare to the broader US population over the upcoming decade
Make our towns, cities, states and country safe for all of our residents
Provide universal basic income so a cracked phone or flat tire doesn’t derail someone’s existence
Provide universal childcare to those that need it
These are things an overwhelming majority of the country want. People have been tossing around the terms “abundance” and "growth agenda" for a lot of this. Those are great words. The spirit of all of this is that a rising tide lifts all ships, and we can rise the tide. We must.
Now is the time to make this happen because people are tired of feeling like shit. The extremes are fueled by anger, not hope or vision, and that is a recipe for disaster. The middle 70-80% of the country deserves a party or multiple parties that break away from the polarizing forces of politics and focuses on helping the USA to navigate what will be the most volatile and tumultuous decades of the past fifty years. We are hungry for this.
We have a generational opportunity to lead with vision, not vitriol. To build a movement of respect, resilience, and results.
One that lifts the floor for everyone—not with anger or ideology, but with optimism and action.
I love our bakery. Let's invest in it so everyone can get a piece.
But AI is non-deterministic. Nobody really knows what's going to come out of it when we put something into it. So alignment of AI with our goals as human beings is priority number one. Being right can mean a beautiful future where everyone is happy and prosperous and being off by one degree can mean sayonara human civilization. While every external force from capitalism to international relations to the innate human need to pioneer the frontier is pushing us to go, go, go, it is very much in our interest to take our time and do this right. In the long run, that will get us to where we want to go because slow is smooth and smooth is fast.
