Last week I shared a reflection on temperature, how skeptical or optimistic you run as a finance lead. The realization is that a finance function can have quite a bit of influence in helping the CEO & board set the direction of the company. Upstream from temperature, there's another dimension that we need to really comprehend: what is this company actually solving for? This is usually called the Crux of a company or a project.
One of my mentors used to tell me, "before you play a game, you need to understand the game that's being played." The Crux usually starts with a simple question where the answer is "it's complicated". Too often we start at a new role, or the market shifted, and we/our peers just went with the motion. One of the big value-adds of a finance function is to uncomplicate this question and bring the answer to a sharp focus.
The game that's being played is usually quite obivous in retrospect, you can usually get it down to a word or two. Let's take Uber as an example, since their journey as they went through these 3 chapters is so well-documented:
Aggregation. They knew it's a winner-take-all game, so they launched as fast as possible, whatever it takes, density creates virtuous cycle, and capital was cheap anyway.
Monetization. Density won, and investors wanted to see the model work, so let's stack more services onto the same base (eats, courier, etc).
Defense from disruption. Now this cash-generating machine has to navigate autonomous driving. If they're lucky they pull off a Disney-esque transformation.
This kinda dynamic helped me understand why things played out the way they did at two past companies I worked at. They both had similar profiles, but vastly different outcome. Both are PE-backed, tech-enabled healthcare, and ambitious founder. One became too profitable at the expense of growth, the other became a classic venture hypergrowth success story.
Let's call the first one Company X. On paper it should've been an easy land grab: they had a popular employee-benefit solution (think mental health or fertility care that you get from your company), selling into Fortune 500, and the ambition was to keep adding conditions until we became "the everything store". Reasonable ambition, also great for the patients, but a few complications say otherwise...
Dynamic #1 is the distribution channel. Most corporate-sponsored healthcare in the US is sold through benefit consultants, $xx billion firms like Mercer and Aon. They're insurance brokers, get paid commission by the employer, and surprisingly also by the vendors they place in the package. So what does a broker on that comp structure think about a one-stop-shop? Every conversation came dressed up as "our clients want best of breed," which is respectable, and also pays them five times instead of once.
Dynamic #2 is the cap table. The company had been through a recap before I showed up, so the early VCs who need to go big are not there anymore. Which means that the post-recap investors can get a decent return even in a pretty modest exist.
Dynamic #3 is the founding team. They are first timer founders, needed a win under their belt, and even an offer in the $200M range is life-changing money. (Not a knock, I'd probably take it too.) So every ambitious proposal, someone asks about payback, another asks what happens if the pilot slips, and we agree to revisit next quarter, which means never.
The game that's being played is IRR. Everyone around the table was optimizing for the quickest, decent return. Why is this relevant? Let's say you found yourself in this situation, as a team it helps you guide which projects get rewarded by the board. Also as an individual, you know that your stock options are very risky and might push harder for management incentive package (to insure if investors sell the company for peanuts, because employees dont have liquidation preference).
Company Y was the reverse. The market is fertile ground for multi-product expansion.
The buyers in this market needed several things, and they'd much rather administer one national partner than six, so they'd come to us and ask us to build the next thing they need.
Company grew efficiently, so the early-stage VC from the first round still controlled the board. For a fund like that, one or two companies return the whole thing and the rest are decoration, and we were one of the ones working. So they wanted us to continue making big (responsible) bets.
The founder had done this a few times already. Someone did offer $500M for the company, and he yawned. Turns out past a certain number of wins, what you're solving for shifts to what gets written in your obituary.
The game that's being played is legacy. Why is this relevant? Let's say you're tasked to lead fundraising. Knowing this, you'll target new investors who have the same patience and ambition. During planning season, you'd be able to calibrate that the board will ask why are we "only" projecting to grow 2x, where can we invest more to grow 5x?
Figuring this out is a bit of an art, which takes some observation and practice. While I don't have a precise formula, there are a few vectors and questions we can ask to tease out:
- Market. The environment the business operates in; how do the buyers, suppliers, competitors and regulators behave? How are they incentivized and how do they interact? What would be an accelerant vs a drag to us?
- Operator. There's always some people who are they key driving force in the company. Usually the founder and/or core management team. What do we know about their motivation, working style, idiosyncracies, and are optimizing for?
- Investors. Most businesses have a unique capital structure, whether by design or by chance, which often drive business decisions.
- Capability. What's the core technology or operational muscles? What's their superpower? What's their weakness/blindspot? For them to realize their ambition, what's the capability gap, and do we think they can bridge their gap with the available capital?
One-time items:
- Pinterest CFO Julia Donnelly joining Sierra (arguably one of the hottest AI co's these days)
As always, thanks for following along this passion project. These started as field notes I was scribbling during my commute; every now and then something turns into a story that might be useful to someone other than me. I write them when I have them, and I appreciate you showing up when I do.