“If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”
I worked as an Associate Partner at McKinsey for three years before starting Meanwhile. Folks often find that surprising. I wasn’t the only YC graduate there but there weren’t many of us.
I did this for both practical and aspirational reasons.
Let me get the practical reasons out of the way:
I wanted to make money and provide stability to my family after having worked four jobs in three years.
McKinsey is prestigious.{1} I had never worked at a traditionally recognizable company, so I wanted to derisk my resume by working somewhere with high signaling.{2}
The work was more interesting than {insert name brand tech company, and the people were, on average, more curious.
Let me unpack the aspirational reason I joined. I wanted to understand my competition. I thought McKinsey would be a great way to see many concrete challenges inside large banks and insurers. I could then pick a problem to tackle in my next company. That didn’t quite work out exactly but I learned deeper truths about where startups can win and compete.
A common criticism of McKinsey is that clients hire them to give answers they already know. It’s all just cover-your-ass. I am sure that happens (perhaps a lot), but in my ~25 engagements at McKinsey, I can honestly say that not once did I think the client already knew the answer.
Most of my time was split across two types of projects: building new things inside incumbents and helping incumbents address deep-seated risk/compliance topics around or through technology.
On the first, McKinsey has this practice called “Leap by McKinsey,” where a client hires them to build a new business unit, a new division, or a new “startup” within the company. I would go in and be the “entrepreneur in residence” along with a core startup team, like a CTO or head of product. I’d serve as the interim “GM” or “CEO” of this new initiative. The team would grow with folks from the client. Then we would slowly replace ourselves with leaders from the company, coaching them through the transition until we were out of a job.
This was really fun, actually. I got to start one startup a year for three years. And the big lesson here is that if you can create a team that ships inside one of these companies, you can grow very quickly. Two of those three projects got to $25M in ARR (or equivalent) in my time working on them. If you launch something decent (I won’t even say good) inside a big incumbent, they will sell the hell out of it. They have an install base, they have salespeople, and they have enterprise relationships.
The adage that "first-time founders are obsessed with product, and second-time founders are obsessed with distribution" took on new meaning for me through these projects. What I discovered wasn't just that distribution matters—that's obvious—but that the relationship between product development and distribution advantage is symbiotic rather than sequential. At McKinsey, I witnessed how even incremental product improvements could achieve remarkable traction when paired with established distribution channels. But I also observed the limitations: when incumbents tried to disrupt themselves or their industry genuinely, organizational gravity often pulled them back toward the familiar. This tension revealed a critical insight that would later shape Meanwhile: to break into a highly-regulated, commoditized market like insurance, you need both a truly differentiated product that incumbents can't easily replicate and an associated distribution strategy that leverages their blind spots.
On the second project type, I worked on risk transformations for two of the Big Four banks.{3} These projects are very high-profile, critical projects that no one is happy about. They are driven by some regulatory mandate from the Fed or the OCC or whoever, who has made clear that the bank doesn’t have control of their risk and compliance issues. Usually data, technology, tracking, metrics, etc, is a huge part of both the problem and the presumed solution.
This work was less “fun’ but perhaps more instructive. On one level, it made me wonder whether any scaled institution is governable. If you have hundreds of thousands of employees, whether you're a huge bank or the California State Government (where I was inaugural Chief Data Officer), I’m not sure there is any system you can set up to make it work. I’ve become sympathetic to Brandeis’s notion of a Curse of Bigness.
To be less abstract, though, there is no fixing institutions that have gotten so big. They can build a new business unit that does something innovative (well, if they hired me), but reforming their core business is impossible. Just too many people, too many processes, too much regulatory overhang. But if you start from scratch…
Which gets me to my actual theory of the world right now. AI and automation create a significant opportunity in developing vertically integrated, full-stack solutions to compete effectively and capture substantial market share.
Our vision at Meanwhile is to build the world's largest life insurer as measured by customer count, annual premiums sold, and total assets under management. We aim to serve a billion people, using digital money to reach policyholders and automation/AI to serve them profitably. We plan to do with 100 people what Allianz and others do with 100,000.
And though when we started our business in January 2022 (ChatGPT wasn’t out yet), you could begin to feel that something like that was possible in a way it wasn’t before. Every day, we feel closer to that vision as AI tooling improves. But it’s a mistake to think the easier thing to do is to build an AI tool for the incumbents. My experience tells me that won’t work. The path of building yourself anew is much harder, but the prize is much bigger.
Footnotes
{1} McKinsey has had a lot of scandals uncovered since I started there, particularly around their historic work on opioids. That work was quite bad.
I never witnessed anything unethical or unexpected at McKinsey; folks were generally thoughtful and well-meaning. Internal self-reflection and debate (“uphold the obligation to dissent”) were celebrated. I remember when one of the NY Times exposés came out, a member of the Shareholders Council (the board of McKinsey) was fielding questions/comments/reactions in the San Francisco office. A Business Analyst got up and ripped him apart. I thought the BA was naive, to be honest, but there aren’t many professional settings where the most junior person can honestly debate the most senior with applause.
{2} I grew up somewhere between working class (my Dad as a postman) and “elite” poverty (my Dad as a college and then graduate student). The point is that where I grew up, I didn’t know any professionals: none of my friends' parents were lawyers, doctors, accountants, professors, or whatever. It was entirely outside my experience until I went to Brown. There was undoubtedly a part of me that saw the opportunity through McKinsey to get a credential that is part of that pull-myself-up-by-my-bootstraps narrative.
{3} At McKinsey, there are usually stringent rules around not working for competitors, or even talking to folks who work with competitors. This is taken very seriously, but on work that is considered non-competitive back office like risk, compliance, people/organization/HR, these rules (with client permission) are relaxed.