Decade in Review

07 Jan 2024

In the summer of 2016, after a 1.5-year sabbatical, I concluded that (1) I would dedicate my life to extending the longevity of humanity and (2) I would spend up to a decade methodically preparing myself for maximum impact.

Now, at the end of 2023, I consider that preparation over. So, this annual review will be special; it’s not just the end of the year of my life but the end of an era of preparation.

Decade of Preparation

When you zoom out to universal time scales, it’s clear that Earth is a temporary home because every moment that life is only on Earth, there is a risk that life in the universe could end.

Chaos Theory tells us we cannot predict calamity, only that the certainty of types of calamities for a given year, like earthquakes, war, and so on, will go up. Thus, every quiet year that passes increases the odds of doom the following year as instabilities accrue.

With this in mind, it becomes clear that (1) domesticating space and (2) mitigating the risk of destruction in the meantime are the only two activities worth thinking about.

When I think about the longevity of humanity as a whole, I find myself drawn to the meta technologies. Especially these three areas:

our biology
our tools
our ability to collaborate towards common goals over long time horizons

If I empowered individuals by either giving them control over their biology or the ability to scale out their impact with tools, then overall progress would tick up.

When I was conceiving of this, I was working as a carpenter with almost nothing, living in a room smaller than my closet now with no money. I was still determining exactly how I could tackle these problems.

What could I do? What would I need to become? Politician? Activist? Scientist? All too low power, with no control, with long, long roads to power but I thought the path of tech founder viable because:

it was possible to generate vast resources quickly
I’d have control over the deployment of those resources
I could have an impact along the way

So, I studied startup successes and failures; how do big companies get born? How do they go wrong? How do they go right? Who are the founders who succeeded, and how can I be like them? Who are the founders who failed, and how can I avoid being like them?

One insight was that mega-successes like Amazon aren’t simply a great idea, executed expertly for decades, but created at the right time and evolved at the proper intervals. Furthermore, there are only a few specific business models that can get that big. The growth curve potential of a company is limited by these factors. This is good news since it tightens the options for the strokes of my life – if I want to swing as big as possible the paths to doing so are few.

If I wanted to go as big as possible, I would need an internet moment, a great idea, and to be the person to exploit the opportunity.

So, I drafted a high-level plan:

liferaft – get a job in software (1 yr)
prodigy – become a world-class engineer (2-4 yrs)
founder – be seen as a high probability bet via prior success or startup experience (2-6 years)
rocketship – build 1st unicorn startup (10+ years)
scale – continue to grow and spawn initiatives to tackle the above three problems (remainder of life)

Each one of these blocks was non-trivial and terrifying for who I was at that time. But arming myself with this simple rubric, I had sharp razors to slice decisions. Ah, what zen.

Life Raft

In the summer of 2016, I did my first raise of ~$10,000 to study web development full-time. I was so terrified; I’d never asked for help before. But delaying months meant millions or billions in future value destroyed or delayed. So, I presented my plan to friends and family, collected $500-$3000 checks, and then executed. Eight months later, I had multiple 6-figure offers in Silicon Valley.

I took a job at Counsyl because it was in genetics, and manipulating biology is urgent. What greater tyranny is there than the genetic lottery? What greater tragedy than our own bodies vibrating apart?

While I was there, I deepened my study of genetics; I took organic chemistry through Khan Academy and Molecular Biology through MIT open courseware, as well as a half dozen other courses. But despite all the advancements we’d made, I realized that biology required too much upfront capital because the entire industry was approaching biology wrong. It was demoralizing.

I became convinced that if we wanted to control our bodies, we needed to start not by trying to change our bodies but by creating life and biology from scratch. As we built synthetic life, we could build models, tools, and approaches that would enhance our ability to do molecular engineering in a fine-grained way. Then, with this wealth of tools, we could edit legacy systems (our bodies) as an engineering discipline as opposed to the fancy gambling we engage in now.

I resolved to gather the necessary capital and prominence to steer biology in this direction.

Prodigy

In mid-2019, I left Counsyl after being acquired by Myriad Genetics. My plan called for ideally working with world-class engineers doing an early-stage startup so I could both become the best possible engineer and also learn as much transfer from successful founders.

But boy, it is hard to find successful repeat founders at the right time. I didn’t get the two-in-one so I went with the backup plan – working at one of the best companies on the planet. I had offers from Amazon, Meta, and Twitter, in addition to the startups I was looking at.

I went with Meta because I was interested in XR; the boot camp model let me pick and choose my team, and they paid well. A year later I was a better engineering pillar lead for the VR product org (300 engineers). A year after that, I was expecting a promotion and had been floated the idea of being a better engineering lead for all of Oculus (1000 engineers).

It was strange to think about, making nearly 10x what I had as an electrical engineer out of college after four years of work. Curious what the right motivation can accomplish.

But how would this help my goal? I felt I’d reached diminishing returns, and I needed to keep my derivative growth high.Being exposed to a large organization was helpful, but startups are about running a squad. I’d never have the millions or billions I’d need to tackle the three areas of interest, and I had little faith they’d be done “right” if I didn’t do it. The extra cash would be nice, but I had $ 300+k in savings – that’s years of ramen.

So, I published this post in the summer of 2020 and quit.

The conventional wisdom is to line up something before you move on but that’s a scarcity mindset. The reality is every moment you delay going full out on your goal pushes out the time horizon of reaching your goal.

Founder

I had an issue; I needed to figure out what startup to do. I gave myself six months to figure something out or join a program. I iterated on ideas, made prototypes, and did some early testing, but I was crippled by self-doubt. I felt intimidated by the problems I was genuinely interested in and unmotivated to truly pursue what I was confident about.

So, I began looking at venture studios when I got recruited by Fractal. Foundership on training wheels. The equity deal was horrendous, but I wasn’t there for equity. A friend and mentor at Meta asked me, “I could get you $3 million to do a startup; why are you going to be a bullet in their machine gun.” I responded, “I want to learn how their machine gun works.” if it was a bad deal, I could walk away. I was there to learn to be a founder and get validation with the side benefits of upside potential and downstream halo effects. Given the structure, I thought a quick exit was possible, and if it didn’t make sense for the business, I would replace myself once profitability was reached.

In January 2021, I speed-dated with Khaled. We hit it off, got our funding, and started LeftLane. We walked into dealerships, designed the product, and in April, we hired our first three engineers: Alejandro Frias, Fritz Copes, and Brandon Antonelli.

By July, we’d shipped to our first dealership. By August, we signed a 6 figure contract with a $1 billion dealership based on our progress. It was a huge validation and a fun deal to work on! I was instrumental in getting 10x better terms, again and again I’d prove out my own judgement in high stakes situations – especially long term planning.

By January 2023, we closed our seed and grew the team up to 10 when I fired our 4th hire. Over 2023, I’d let two more go until we were back from 10 to 7 – six without me.

I learned that experience matters very little at a startup if it is not coupled with a high growth rate. Our best hires combined both, and our second best hires just the latter. Our worst hires were from larger companies; they didn’t have the hunger, the pace, or the capacity to change. Less can be an advantage, less people, less experience, less nonsense.

As I write this, the company is in full sales mode, growing fast.

After our round in Q1 2023, I came up for air and was feeling disgruntled:

I didn’t particularly appreciate how the round had been advised on – a key value prop. Fractal made claims about “contractually” obligated round valuations, i.e., it’d be zero or X, but the company got a different valuation.
Their research had been flat wrong about our industry – core ACVs were an order of magnitude less than expected – which forced us to pivot to a different market that would take longer to penetrate.
I also had gotten little value from them outside the first three months.

I looked at the equity they were taking for what they were putting in and questioned why I should continue. If they were a true “third founder,” I would have moved to get them out and claw back the vest, but oops, there was no vest for them. I realized that, whether I was there for learning or not, I’d agreed to a poorly structured deal that put dead equity on the cap table.

At that moment, a deal was being discussed to change the equity structure, which made me pause. But I wasn’t going to sit on my hands waiting for a contract and began to lay contingencies. For one, I’d commit to making the team as autonomous as possible. If I left, they would be well prepared; if I didn’t, I could assist with sales/onboarding.

This was now in Q2 of 2023, and ChatGPT had emerged not too long ago. It was exciting, but I’d seen demos of the earlier models. The growth rate was impressive, as was the generative AI – the tech had become magical since I’d last checked in on it. My eyes popped at the money flowing into the space. It reminded me of the ICO craze, but where that was nonsense, there was real magic in AI.

I checked in to see the progress in my areas of of interest and began reading and seeing fascinating papers. By the end of Q3, I began to evaluate different ideas for working on problems I was passionate about with these emerging technologies. I saw mind-boggling potential if I could just connect the dots.

I felt that the first real “internet” moment was here, and we were on the precipice of a globe altering technical revolution.

Around this time the discussed deal finally materialized concretely from Fractal, and I had to make a choice. Could I leave this company I’d built? That’d given me my first gray hairs? This team I’d sold on the mission? Trained and groomed?

But even if this moment hadn’t arrived:

the opportunity cost was too high; given my equity stake, logically, I should do another startup better and faster with 2x the stake
I didn’t want to work with Fractal

While advising someone else about making their own leap at the Redwood conference, I realized all that was holding me back was fear. Fear of disappointing others, and once I realized this, I gave notice and left the company seven weeks later.

At the end of the day I have a greater duty to not disappoint my mission. I was bleeding the future millions earned by future me by dawdling.

I was eager but the reality was that I needed a break. I hadn’t taken more than a week off since 2015. I had been fighting eyestrain ever since a crunch in December 2022. I’d always had inexhaustible stamina and incredible health, but in 2023, I felt fatigued during the day, no matter what I did.

When I ran my first marathon, I broke both of my feet. My left on mile 15, and my right on mile 23. I waddled the last three miles, crying and sunburnt. For weeks, I couldn’t stand up without my eyes watering. You only redline when you aren’t prepared, so you have to burn yourself up to make up the difference. You spend the future for the present, and you pay exorbitant interest.

A marathon pales in comparison to a startup; it’s just a few hours of running.

As much as I loathed it, I needed to reset. If not now, then when? So, I fought down a feral impatience, allowed myself two months off, and traveled to Japan and Korea.

I still studied, I still read papers, but I didn’t require it of myself. No expectations, no schedule, and no taskmaster – I just did it for fun.

Conclusion

These years went by fast but also took too long. I fret on spending 2,400 days this way. I’ve wondered how I could have moved faster. What time could I have reinvested? What extra hours could I have worked? What could I have done better?

I could have never missed a self-review; I missed monthly rollups here and there, and that led to delayed decisions
I could have enlisted founder mentors; I shudder to think how fast I could have progressed with a mentor like myself
I could have shared my thinking publicly sooner to find feedback, friends, and allies
I could have avoided ever letting myself redline in that Dec. crunch
I could have considered a few different options besides Fractal
I could have considered a few more options for a startup apprenticeship
I definitely should not have locked up cash, i.e., retirement accounts, private equity, etc. Why? The expected value of my startups is orders of magnitude greater than the alternatives
I should have fired faster
I could have aged at a lower rate, I was imperfect in my schedule, I didn’t measure soon enough or rigorously enough

Still, while I normally operate from a place of chronic dissatisfaction, at this moment, I look back on the last six years and six months, and I’m proud. I laid long plans, and I executed them. How many can say the same? Few can say they can work at any company they want to. Fewer become founders and 90% of those who do build companies that fail. Time will tell, but I believe LeftLane will make it.

I have learned so much and become an entirely new person, and while I’m not satisfied with who I am (I’ll never be) I’m glad to look back and see so much ground covered:

I leaned into my fears and built the habit of courage
I executed a decade long plan and became who I needed to become
I gave up an easy life for an incredibly hard and stressful life
I got validation from building a startup
I stacked cash for seed funding
I studied, assessed, and prepared for the mega-trend 5 years before it arrived
I met and married Bri
I established a longevity protocol and assessment plan
I mostly aged at about 0.8 yrs/year, not on goal, but pretty good

But I also didn’t make progress in a vacuum but alongside many wonderful friends. I look back at the last 6.5 years with awe and gratitude.

I want to thank everyone who funded me at rock bottom. A special thanks to my wife Bri, who, after dating me for three months, gave me her life savings ($3500) when I was fundraising to get into software. Her parents, Steve and Mechelle, for letting me live in their basement for a year. Your generosity and support meant the world.

Thank you to Jon Quisenberry and everyone else who cut me a $500 check. I know you didn’t do it for the 10% interest.

Thanks to my brother Eric and my parents, Chris and Cindy, for letting me live with them during my sabbatical when I was figuring this all out. Making board games and self-publishing a novel didn’t give any indication of where I was going.

Thank you to Chris Lee at LaunchSchool and his co-founder Kevin for talking me down from taking that engineering job in Mexico!

Thank you, Daniel Kim, at Meta, for singling me out and offering me the role of pillar lead for better engineering in VR product. It set me up to lead a team at LeftLane.

Thank you to Fractal and Bienville for entrusting me with one of your companies. Thank you to Khaled and my team: Alejandro, Brandon, Simon, Fritz, Kevin, and Matthew at LeftLane for trusting me and for taking LeftLane forward.

Thank you, David Price, for inviting me to the startup club and building the Redwood community. Thank you to the Redwood core team, especially Danny, for always taking my many criticisms with a smile. Thank you to Tom for investing in LeftLane.

Finally, I have immense gratitude for all the giants that have recorded their experiences across time. I would have never had the courage to live as I have without these people and the legacy they left behind. What generosity of spirit. Thank you.

It’s crazy to think back to all the moments I felt like putting my head between my legs and hyper ventilating – those scary moments feel so trivial to me now.

As for the plans I’ve laid for the next 10,000 days? I’ll discuss that in a follow-up post.

I can’t help but feel a sense of inevitability, like a boulder that’s just been tipped over the edge of a slope. I am certain I’ll look up X years from now with progress that dwarfs these past 6.5 years. I feel that I am in the knee of my growth curve.

After having raised seven figures at an eight figure valuation, nine, or even ten seems very attainable.