Is Outlier Family and Outlier Career Success Possible?

Last night, my 2-year-old woke up bawling around 1:30 a.m., I think from a nightmare. As I comforted him, and later struggled to fall back asleep, I mulled over an old question, one that resurfaced yesterday again after scrolling through congratulatory Twitter threads about Blake Scholl and Boom's first-ever supersonic flight. A remarkable achievement—perhaps comparable to Tesla demo'ing the first Roadster or SpaceX launching the first Falcon. One image in the replies stood out: Blake and his daughter in an airplane, a nod to his lifelong passion for aviation. For a moment, I thought, Here’s a founder who balanced family and a hard startup. But I learned minutes later that he's been divorced twice since he started Boom.

Here's the old question in question: Can one achieve both outlier career and outlier family success? I personally define outlier career success as fulfilling my ambition of creating outlier economic and societal value through a startup; think iconic once-startups like Tesla, Stripe, or Amazon. Outlier family success to me means having a consistently deep, loving, life's-meaning-enriching relationship with my wife and children for the hopefully-long-time until I die.

"Can you achieve" is probably the wrong start to the question as some people appear to have achieved both. Zuckerberg comes to mind immediately though his family is young and we'll have to see how it plays out; same for Patrick Collison. Bezos, Gates, and Buffett may have counted before their divorces. I'm sure there are other examples. But when someone appears to have achieved both, was it the result of intentional choices, or did they just get lucky?

I speculate that founders who succeed in their careers but not in family life either accept it as an inevitable trade-off or realize too late that something has been lost. Others—Elon comes to mind—simply don’t prioritize family life the same way I do. That’s not my path, so I'll set that case aside.

Assuming Zuckerberg+Chan lasts until death and assuming Patrick Collison will follow, and that all their kids will love them unlike one of Elon's, a few commonalities stand out:

  1. Early success – both struck gold with their first ventures and while very, very young.
  2. Financial freedom from a young age – they could/can afford help—nannies, flexibility, outsourcing all chores and stressors.
  3. Married to childhood or longtime partners – relationship stability before success may insulate their families from turbulence.

Interesting commonalities, but these guys are outliers among outliers, so any conclusions from them or others like them don't apply to me or the vast majority of ambitious people.

Another key factor to consider: What does the other partner want? Given that I haven't yet achieved outlier career success—and there’s no guarantee I will—it would be absurd to expect my wife to downshift her ambitions. This reality likely plays into how sustainable a dual-success path is.

All of the above leads me to a research project idea: assign a "family success" score to the world’s top 1,000 self-made outlier founders from the last 20 years, ideally only those who were navigating career and family growth at the same time to exclude the Zuckerberg types, and analyze them across key dimensions including:

  • Did their spouse give up their career? If not, how successful is their spouse?
  • When did they meet their spouse?
  • When did their first liquidity event happen?
  • Did they experience divorce?
  • How many kids do they have?
  • What’s their relationship with their children like?
  • Were they married before they became successful?
  • How intentional were they and their spouse about maximizing the probability of success in both career and family?
  • etc.

A dataset like this could reveal insightful patterns and help answer whether balancing both ambitions is possible to do with intentionality or if, for most people, one success inherently comes at the cost of the other. For this to be personally insightful, I'd need to find a bunch of examples that fit the mold of Blake Scholl-where outlier success came in their late 30s or 40s, with the path to success including marriage and young kids—and still made it work. I'm sure Blake will say he isn't outlier-successful yet, and that would technically be true compared to Elon/Zuckerberg, but I keep coming back to him as Boom's flight a couple of days ago is what triggered this post (plus, I'm assuming he sold at least a few million dollars worth of secondaries at this point).

The obvious flaw with this project idea is that it needs highly personal interviews with the research subjects and their family members and exes, making it a potential non-starter. But it might not be a non-starter for a pilot version that only includes, say, a dozen people that are willing to be interviewed and are cool with family being interviewed, and while the data from that may not be fully generalizable, it's possible that insightful patterns will emerge. I hope someone does this and publishes the results - I think it would be a bestselling book!