Met someone earlier this week who has had a bunch of major outcomes as an angel investor. This sparked my curiosity and I asked him about his backstory and career trajectory. Turns out these venture outcomes were a result of a series of parlays and things coming together over a decade-and-a-half:

1. He was early at a leading startup in the mobile supercycle, which was acquired by a BigTech in a marquee transaction. He continued at the BigTech for a few years (which in hindsight, was still relatively small at that stage), thus rapidly compounding both his net worth and network.
2. His spouse was an early engineer at a now-leading BigTech, then left to become an early engineer at a startup that was acquired in another OG marquee transaction. Through this journey, she also built a deep relationship with one of the OG Tier 1 venture firms in the Valley.
3. The couple used the capital acquired from this track record to start writing angel checks. Alumni of all the companies they worked at gave them access to some of the best deals.
4. The guy also went on to join a venture firm later, which further added to his creds and network.

Essentially, as a direct outcome of their early individual successes, this couple benefited from a self-compounding flywheel of relationships and capital. Pooling these assets as a married-team further magnified their impact. To their credit, in addition to being highly capable, they had the hustle, risk appetite, and foresight to keep taking shots at various opportunities that came along their way.

Btw, this story is not that uncommon in Silicon Valley. Though the extent of financial outcomes might vary, I know of many such stories where people have benefited from similar flywheels in their tech careers. In fact, this is one of the things that makes the Valley a unique place as there is an adequate density of talent, capital, networks, positive intent, and implicit trust within a small geographical region, which enables such flywheels to take shape in people’s lives. PS: I had written about this idea in my post ‘The Success Flywheel‘.

This story also highlights the importance of something I think about a lot, even from reflecting on my own career – there is a massive advantage to putting points on the board early on in life.

Life is cumulative. It unfolds in a geometric progression and therefore, the timing of your initial wins has a major impact on future outcomes down the road.

Mark Spitznagel, famous tail-risk trader and Taleb’s Partner at Universa, talks about this concept in the context of financial portfolio management and risk mitigation in his book ‘Safe Haven‘.

We are not a casino, or a portfolio of our distribution of possible simultaneous returns. Rather, we are one wager compounded through time. We only get one chance, and, if we shine a bright light on that, we will avoid many mistakes—start thinking about the right things, with a better internal valuation metric: making sure this chance maximizes its chance.

Safe Haven (by Mark Spitznagel)

The idea is simple but powerful – having early wins enables the player to parlay the fruits of that win into the next opportunity while also having a long enough time runway for significant geometric compounding.

Being in the right zipcode like Silicon Valley in tech or NY in finance, also provides a large enough sample set of opportunities for continuous parlaying as well as high rates of compounding given the inherent leverage in these ecosystems.

This idea also makes the case for why students try so hard to get into Ivy Leagues, or why VCs try their best to get into prominent logos early in their track records. It also frames the competitive advantage folks get by starting as a fresh undergrad Analyst at Goldman, engineers who joined Google in the mid-2000s straight out of college, or those in their 20s joining OpenAI right now. The difference in getting these early wins starts showing up a decade later when the slope of the curve of these folks is markedly steeper than those who didn’t.

Of course, logging early wins isn’t by itself a sufficient driver or a definite leading signal of holistic success later in life. Everyone has their own unique journey and has to walk their own path. Still, given the sheer leverage these early points provide, it’s worthwhile to have this at the back of your head while executing your career strategy.

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