Ride It to the Sky

Last year I publicly shared my goals for 2022. I like having a public record of this. Diving in, here’s how I stacked up against my goals from last year. I am really happy with my achievement rate. If these were OKRs I’d consider it a successful year.

I like a tops-down approach for personal goal setting, beginning with answering the question: “If I were 80 years old, what would I regret / not regret having done over the course of my life?” From there I like to list out my ten-year goals at a very high-level, and then dig into annual goals.

This year I have updated my regret minimization framework:

By the time I’m 80 years old, I won’t regret having spent an abundance of quality time with my family, having read and retained the learnings of terrific books and being knowledgeable about the world (both the way things work and why they work that way), knowing myself and what makes me truly happy, having traveled and explored the world to my heart’s liking, spending time in nature, feeling like I’ve made people’s lives better and contributed to civilizational progress through my professional endeavors, and investing in the relationships that matter most with friends and family.

I’ve also updated my long-term (10 year time horizon) goals. I really like how these are simple and more about the way I will feel in ten years instead of objective numerical measures of success.

And finally, I modified my goals for 2023. These aren’t a major departure from 2022, they’re really more of a continuation of what has been. I think it’s good that these are iterative and evolutionary – it makes them feel doable and realistic and hopefully will enable the progress to compound over a ten year period.

Here’s to a fun and meaningful 2023!

Today is my official last day at Fundera / Nerdwallet.

For the first time in my life, I have absolutely no clue what will come next. This is a new experience for me and it fills me with anxiety. But I am eager to learn how to explore and embrace the uncertainty.

When I was a teenager I played tennis competitively. I was a nutcase and would regularly throw tantrums and break rackets when I lost. I saw a sports psychologist and he told me about an ancient Chinese phrase called wu wei which he described as meaning “go with the flow.” While it’s a minor perversion of this Taoist concept, Westerners have adopted it to represent an orientation of “effortless action,” “non-doing,” or “action through inaction.” I love it and it has served me well.

As a Type-A-Control-Freak-INTJ, wu wei doesn’t always come naturally, but when it does it’s beautiful. I am ready to go with the flow.

Every once in a while I interact with a new product and have an epiphany: “Ah! This is it. This is the future and how the world will work.”

Over the summer I caught up with one of my favorite entrepreneurs, Howard Lerman, and he said he had something to show me. It was a new product he and a bunch of colleagues from the various companies he had previously founded were building. He gave me a high-level overview of what they were doing, but showing always beats telling. And when Howard demoed Ro.am, I knew that I was witnessing what the future of work looked like for companies that operate out of an office, remotely, or a combination of the two. There has already been a lot of good coverage of Roam and I encourage you the check it out: Howard’s remarks, CNBC, TechCrunch, Squawk Box, and IVP.

Many companies are trying to find ways for people to work better together remotely by creating some version of a browser-based HQ. We’ve seen everything from Meta’s futuristic avatar-based version of the workplace metaverse to various permutations of gamified work experiences. Most of them come across cartoonish and impractical. But Roam actually feels like a HQ, but in the cloud. It’s a viable virtual office.

I fell in love with it for several personal reasons. First and foremost, it mimics a physical office. I can see who is present, who they’re meeting with, “knock” on their “doors,” and have spontaneous conversations. It’s the only thing I’ve seen that comes close to the in person experience. It’s intentionally skeuomorphic, or as Howard describes, a “breakthrough office graphical interface,” the same way Apple designed for the iPhone when they were acclimating the world to transitioning from desktop to mobile.

I need to be around people in order to feel energized, productive, and happy. If I ever were to build another company, I’d want to work from home 1-2 days per week and be in an office surrounded by people 3-4 days per week. Roam is the tool that creates a seamless experience transitioning through these modalities, ensuring nobody loses out on the magic of collaboration. It also eliminates roughly 50% of Zoom meeting time by making quick hallway conversations practical – the average meeting time in Roam is ~8 minutes!

The shift to distributed teams, remote work, and an asynchronous cadence has been confusing and hard for most founders and leaders. There’s always a creeping suspicion in the back of your mind that people are phoning it in and that you’re losing the magical moments that make building things so special and rewarding. And for those who value a performance based culture, the transition to remote or hybrid is a steep learning curve with few best practices. Roam is a happy equilibrium. It’s the solution we’ve been waiting for that needs to exist. It’s not that Roam enables managers to surveil, it’s that it creates a work setting that enables people to flourish regardless of where they are. Some people and roles will always be able to operate asynchronously and that’s great. But that’s the exception, not the rule. And Roam empowers different configurations to embrace best practices and develop new ones for a rapidly changing work world.

I believe that Roam will be the platform that enables more magic moments between colleagues and helps us to do even better work together. I’m lucky to be an investor backing Howard and the incredible Roam team. Sign your company up here.

This weekend this tweet appeared in my timeline and it deeply resonated with me:

pic.twitter.com/mvf7T0ayOH

— Sid Yadav (@sidyadav) October 16, 2022

Over the past several years I have noticed a trend that people are starting companies for the sake of starting companies. I am a big proponent of entrepreneurship and believe it is a very positive thing for more people to feel empowered to start companies. It’s how we make more progress faster. But I do not think it’s a good thing to be a founder simply for the sake of being a founder. And this tweet characterizes how most people who fall into that bucket go about it. Because the gravity of wanting to start something is so strong, people do tons of research across a variety of different problem spaces until they land on something they think may have potential. And they do this without a deep passion and vision for the problem they are trying to solve.

I think this is a sub-optimal and time-wasting path of entrepreneurship. In my experience, the best founders start with a bold vision of how something in the world should work and what the end-state of the problem they are trying to solve looks like. They have a strong product vision and relentlessly pursue it. They are obstinate about what success looks like, but pragmatic enough to know that they may need to modify the course of their journey in order to succeed. Stubborn about vision, strongly opinionated about where to start, and flexible enough to make modifications once learnings are accumulated.

Loading up on research and constantly pivoting based on feedback before taking a first step can be a negative indication that a founder lacks conviction. And it also deprives founding teams of developing the most important muscle they need when getting something from zero to one and beyond: shipping things. Talking to potential customers is important, but shipping is better. Sometimes you need to will something into existence, and there’s zero substitute for a strong vision coupled with the ability to ship. No amount of customer research can compensate for a lack of this.

This doesn’t just apply to the earliest stages. In companies that have reached product market fit, I have seen customer research become a substitute for vision + shipping. It leads to inertia. Again, research is important, but if you truly have conviction about something, the best way to test it is to build it. There’s no right way to build a company, but I have a strong bias towards doing the things that will generate the momentum you need to accomplish ambitious goals.

For technology companies, the market has drastically shifted from prioritizing growth above all else to the quality of the underlying business and its growth. This is healthy and grounded relative to the irrational exuberance over the better part of the past decade.

One of the things I have been thinking about recently are the parallels between this market correction and the way we think about the broader economy. So much of our capitalistic orientation over the past century has been focused around growth: “Growth in GDP equals good.” It’s a simplistic point of view that doesn’t account for underlying flaws, medium and long-term instability, and negative externalities associated with that growth. It was significantly more good than bad by any measure of progress, but we are beginning to see the objective measures of its limitations.

As more of the global population comes around to the consequences of the perils of the climate crisis, economic inequality, and the rapid attack against democracy, it is incumbent upon us to reevaluate our growth at all costs mindset and begin to value the quality of growth above arbitrary measures of it. We (i.e. Western Civilization) have operated like a company that spends money to grow top line without accounting for the health of the underlying business and its constituents. And that is now completely unsustainable.

While I am no fan of presenting problems without solutions, I do believe this is a critical concept to collectively wrap our heads around in the decades to come. We have an entrenched set of behaviors and way of life that is comfortable, but not healthy. We produce significantly more foods than we need, and as a result there is an obesity epidemic. To our hearts’ content, we manufacture and buy an unfathomable amount of shit we do not need and let much of it go to waste. We partake in activities daily that are enjoyable, but detrimental to long term health and sustainability of virtually every natural and human made system.

When I first dug into the upcoming energy transition, it became obvious just how much and how quickly we need to improve the way we produce energy in order to continue to flourish as a civilization. There is a profound difference in scaling energy and scaling quality energy. We are entering an era where the quality of growth matters exponentially more than growth in and of itself. While this is admittedly a rather highfalutin and subjective musing, I do think there is merit to it and I am particularly energized by the concept and think that not only is it a good thing in the long run, but it is absolutely necessary. More than anything, I am committed and excited to support entrepreneurs and causes that share this sentiment to make it a reality.