On Startups, Impact, and the Search for Meaning
I turned 50 last year, an event that really did a number on me. It came with the sudden realization that I don’t really have that much time left on this planet, and more to the point, that much time to make the mark on the world that I hope to before, you know, transiting to the next plane of existence. I reckon I have at most twenty years left to do anything really meaningful in my career — at least assuming I don’t plan on working into my 80s like Joe Biden or Martha Stewart. Twenty years is actually not all that much time if you think about it. So turning 50 deeply affected the way I think about my priorities and how I plan to spend the rest of my working life.
The last 6 years, I’ve been experimenting with startups as the vehicle for making my dent on the universe. It’s been amazing, fun, hard, painful — all of the startup things. But here’s the thing: startups can take a long damn time to really make an impact on humanity. And with the proverbial clock ticking, I’m having to reassess whether being at an early stage startup — at my age, at least — is really the best way to achieve my goals.
Like many ambitious people, the focus of the earlier stages of career was on gaining more XP and more gold pieces. At some point it became clear that I had more or less maxed out my character stats, so the question became, what should I focus on next? For the last year or so, I’ve been able to work on things that I find intellectually satisfying and, well, fun — which is of course a huge privilege that not everyone gets in their career. But it doesn’t necessarily get me closer to doing something truly impactful.
The US election in 2024 turned out to be the kick in the gut that I needed to gain some clarity. My feelings on election night gave way to a realization that no matter who our elected officials are, there is a role that I can directly play in making the world a better place, if I choose to apply myself to that end. Rather than just being smug that I voted for the “right” people and watch my country go to hell from the sidelines, I can actively do something that can have a positive impact on the world — to be a light in the darkness. It might seem obvious, but it smacked me in the face on the night of November 5.
So, I updated the objective of my main quest. The question is, how to actually do it?
Move slow and break things
The hard fact of startups is that they can take many years to have any real mark on the world — assuming they doesn’t fail first. I’ve been at four startups: two were acquired, and two are still early stage. If I have to be honest, the amount of real-world impact that I have had working at those companies is, approximately, zero. Even the acquisitions were really acqui-hires, and for the early-stage companies, it’s still years before anyone would be able to tell.
I would hope that nobody joins a startup with any expectation of large-scale impact in a short time period. These things take time. As an example, let’s take OpenAI — they’re hugely successful, right? But OpenAI has already been around for nearly ten years — they were originally focused on things like teaching AI to play video games (anybody remember that?). False starts notwithstanding, startups seem to take on the order of a decade (give or take a few years) before their impact is really felt, if they survive at all. When you combine the long incubation period with the high failure rate, it feels like continuing to do the startup thing won’t give me very many more shots at goal.
The other problem with startups is that, no matter what the lofty goals are when starting out, it almost always turns into a chase for customers and money. So a startup trying to build the next-generation LLM-powered agent framework for enterprises ends up making chatbots for customer service for pet salons. Eventually the startup might get back to chipping away at its earth-shaking mission statement, but it has to earn the right to do so — most startups sadly never do.
Larger companies that have survived the startup phase have earned that right, assuming they didn’t pivot too far away from the original goal. So the obvious thing for me to do would be to go back to Google (or join Microsoft, Amazon, or Meta, or some other big tech). Within a couple of months, I’d almost certainly be able to touch a billion-plus users, at least in theory. But here I am reminded of the downsides of Big Tech for someone, like me, who values autonomy and Getting Shit Done. Yes, the resources and reach are there, but at the (very steep) cost of crippling bureaucracy and risk aversion. So it’s very much a double-edged sword.
I also want to be careful not to confuse “impact” with “making a lot of money” or “launching a product used by a lot of people”. Those are, indeed, kinds of impact, but not necessarily the kinds that I care about. Having done both, it’s a little hard to get that excited about doing a re-hash of the same sorts of things I did at Google, just with someone else’s logo on my business card. I’m not incredibly motivated by what most big tech companies are doing these days: selling ads, selling consumer software, or selling cloud services to banks. Those things aren’t going to get me up in the morning.
The midlife pivot
A friend recently recommended a book called From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life, by Arthur C. Brooks. The premise is that highly successful people often build their careers by leveraging some key strengths that are not always available to them later in life — such as sheer brilliance, boundless energy, or the ability to understand C++ templates. Later in life, those skills tend to fall off, sometimes drastically, due to biological changes — such as a drop in neuroplasticity as we age. It is not common to find someone who was super successful early in their career continuing to deploy the same skills later in their career to the same effect.
Brooks argues that the key to a fulfilling later-life career is to pivot to leveraging a different set of strengths — in particular, those that involve synthesizing knowledge, mentoring others, and sharing acquired wisdom — strengths that can only be acquired through, well, experience. The message in this book spoke to me as someone who is questioning what to do next after having done a lot of cool stuff in my more youthful days.
The next adventure
There are lots of things I could do, most of which I’m not qualified for (fixing the healthcare system, for example), or which don’t really leverage my particular expertise (such as volunteering at a homeless shelter or teaching underprivileged kids how to read). These are worthy causes, but I’m not the best person for them.
As it happens, I got an opportunity recently to join a company applying AI to critical challenges in government and national security. I have some experience working at the intersection of AI and defense, and this is an area that I feel needs much more investment from the disruptive and nimble (i.e., the Silicon Valley-style) elements of the tech sector. The role is highly aligned to my interests and skills, and has a mission behind it that I truly believe has the potential to make a really positive and lasting impact on the world. So I jumped at the chance, even though it meant leaving an early-stage startup that I have loved working at.
I am fully aware that government and defense work can be controversial. The potential for both massive harm and massive good when applying AI to these emerging domains is fraught with risk and opportunity. For better or worse, AI is already being adopted in these domains to a large degree, both within the US and around the world. If I can act as a force for good, shaping future AI systems in ways that preserve privacy, and are ethical, robust, and reliable, this feels like an important place to apply my skills and influence.
There will always be a part of me that wants to build my own thing, without being constrained by working for someone else’s company. I probably have one more startup left in me, but it would make sense only if I had the idea that was worth spending, realistically, the next 10-plus years to make real. For now, I’ll have to be content with the potential for more near-term impact, even if that means less autonomy. I hope it’s the right tradeoff.
Disclaimer: This post represents my own opinion, not that of my employer.
