Ask Me Anything

You mention you're "using [your] work to practice communication and influence, and to get better at defining problems and deciding which ones are worth solving." This definitely sounds to me like you're making progress toward real entrepreneurship. Those skills will transfer well.

The biggest question I have about whether you're making "real progress toward entrepreneurship" is whether you, like many people, keep telling themselves this for decades until they lose the motivation, or whether you will take that concrete leap at some point. I have a friend who has been talking to me about his life desire to start a company of his own... for literally two decades. There's a way in which the idea of a future self who's an entrepreneur can be a form of work escapism that quiets some dissatisfaction within us, a sense we aren't doing all we're capable of.

The only way you will know whether you're making real progress is if you set a timeline for yourself and keep it. You can definitely start your own company; literally anyone can. And if you save enough, you'll definitely be able to go a year without income given your strong past track record. The real question, which only you can answer, is whether you'll set that timeline for yourself and keep it.

Starting a company is in a way like pregnancy. I don't think anyone is truly ever ready for parenthood. Yet it's done all the time, sometimes successfully. I bet you'll find 90% of the learning is on-the-job.

You sound to me like someone who'll follow through on this. I'd love to hear back from you once you've started your company!

Some of the best engineers I've worked with have been Serbian! I hope to visit Belgrade one day.

Your approach sounds wise — building the fundamentals will position you better for getting a job at a FAANG company. There's unfortunately no magic to getting those jobs, but you stand a good chance if you often find yourself the smartest person in the room. One of the things I've enjoyed most about working at major tech companies is the amount of interesting conversation that can be had. I've often been on teams where I learned so much — not just about technology, but about many other fields — simply by listening to what others on the team had to share.

My sincere hope is that you find the same opportunity for yourself. It has become increasingly harder to get jobs at some of the top companies, especially as layoffs continue, so remember that it's largely a numbers game. You have to take enough shots at goal for something to work out. Stay persistent. Even the best people get rejected often. I was rejected in the very first round the first time I applied to OpenAI; I was rejected multiple times at Microsoft when trying to switch teams. When it feels hard, remember that the top companies are biasing strongly towards false negatives because the current market allows them to.

Build those skills and stay persistent!

So sorry to hear about the layoff. It's wonderful, however, that you have the flexibility to stay at home a bit, especially in the very labor-intensive period of newborns and toddlers. I hope you have a chance to rest and to spend some precious time with the toddler and the upcoming baby.

Interestingly, my inclination is to recommend you deliberately stay out of the job market the next year+ precisely because of the pace of change. This might feel counterintuitive, but I'll explain.

A major risk right now, when choosing any employer, is that you'll bet on the wrong employer who'll soon be outmoded by some development in AI. For instance, two years ago, OpenAI was the clear leader in LLMs; if you had signed on to a company whose enterprise license meant you had to use only Codex this whole time, you would have fallen behind where the industry is going.

The time you have at home comes with the great benefit of the opportunity to try all the AIs and all the latest tool approaches. For instance, OpenClaw was clearly just a beta of where independent agents will ultimately take us. By exploring on your own, you'll have the flexibility to try multiple products and approaches. The other benefit, in my experience having worked exclusively with AI at home over the past 18 months, is that you objectively learn much faster how to use AI most effectively because you're empowered to own the entire stack of whatever you're building, end-to-end. My time off has given me the chance to dabble with Supabase and Vercel, whereas I used to be exclusively Firebase and GCP. I've released a game on Reddit; integrated with Stripe; expanded through Resend and Twilio. There's just a lot more opportunity to adopt the latest: not only in LLMs, but in the entire services ecosystem.

During this time of rapid change, I think you're well positioned to become a much stronger candidate by exploring broadly and adopting the very latest things as opposed to trying to bet on the right company to have policies that allow you to use a certain tool or approach. This time off might be the best opportunity to take your career even further, positioning your skillset well for your next job.

Deciding when to step away

In some ways the decision to step away from OpenAI a year and a half ago was very easy: my mom had advanced liver cancer, and I moved my parents into my house so I could take care of her full time. That was a great decision, and very easy to make because I knew it was the right choice. Zero regrets on that.

The thing I struggle with more is how and whether to get back into industry. I still love building things and am working full time on a variety of side projects. But it's not the same as having coworkers. I'm a bit unsure if joining a traditionally structured company is the best thing for me right now, since AI enables us to work in much smaller teams. Part of me wonders whether the best work environment for me might be a team of 3-5 people.

A little part of me wonders whether I should also try a completely different profession, the way I've been teaching at the University of Washington part-time for the past 8 years.

Managing intensity

I think I did an ok job at this during the period of my life when I worked a lot longer hours. But some things made it easier:

• In the period of work where I had a sleeping bag in the office, I was married without kids. So I had far less responsibilities.

• I was a lot younger in many of those crunch periods, which made daily energy less of a problem.

• I think I was objectively less effective on a per-hour basis during those sprints where I worked very long hours in the office. More effective in totality, but less effective per unit time.

• I'm not convinced all that intensity was positive. I suspect I could have reached similar career goals without pushing quite as intensely had I chosen better how to spend my time (e.g. oftentimes during my early 20's, my extra hours were spent doing things that weren't that important).

Internalizing feedback

You're right that not all feedback is good or wise. The difficulty is in differentiating the two. I think that if you only ever implement feedback you already agree with, you arguably might not need the feedback at all. We should at least occasionally try to implement some feedback we didn't at first agree with, just to witness the empiric results. But ultimately, not all feedback is good, and some feedback might be downright harmful.

I don't have any wisdom around this other than to say it helps to triangulate amongst a few people. For instance, I've recently gotten feedback from two different sources, one professional and one social, that I jump too quickly into the next topic of conversation without letting emotionally heavy things have some quiet space to sit. The fact that this came unsolicited from two different sources is a strong indicator that the feedback is consistent and accurate. I'm going to try to change this.

Could it be that I am not trying hard enough to find projects that both allow technical growth and are well-aligned to team priorities? Any tips for doing that?

Companies like Meta, Microsoft, and Google are so large that there should often be teams with opportunities that better fit where and how you want to grow. This becomes harder during certain times, like around layoffs, since people become risk-averse such that:

1. People don't leave teams as much as they usually do, and

2. Managers sometimes pause hiring until the future funding picture clarifies

Despite those dynamics, the strongest people always have choices. Managers will often bend over backwards to get someone who's consistently outperformed in the past. So, to your question: a) I'm pretty sure there are other projects within Meta that suit your growth ambitions, and b) those opportunities will be easier for you to secure the better your performance track record (which is incidentally why you should do a great job no matter where you are, even if you know you're leaving soon).

In terms of thinking about what to learn / how to grow, do you see certain technical disciplines as having more 'AI longevity' than others, given the rate of how quickly coding models are improving?

People answer this question way too confidently, IMO. For instance, you might recall all the breathless articles two years ago about how the future was all going to be "prompt engineering." Or the current talk around "taste" being everything, and PMs inheriting the earth.

These perspectives have all captured elements of what's true -- but if the dot com experience taught us anything, it's that it's very hard to call the winners during times of rapid change. VCs are in the full-time business of trying to call winners, and yet the average VC performs terribly. How are people who only occasionally think about these dynamics supposed to do any better?

All that said, my intuition is that hard things will always build more valuable skills, simply because they're hard. I have a tough time imagining a lay vibecoder stumbling out of a mediocre business school doing better, on average, than someone who invests deeply in understanding how to build large scale systems with the help of AI. Hard things are often profitable if not simply because most people aren't willing to work that hard. So during times of uncertainty, I'd bet on the person who:

• Embraces instead of resists change

• Works harder than others to stay on top

• Switches their approach based on high alertness about trends of change

How have you navigated a growth/risk-reward tradeoff in your career? When did it pay off in direct or surprising ways, when did it not?

My personality is very open to new experience, so I've rarely been risk-averse. I'm much more open to change than the average person, so perhaps I've had an edge this whole time. But FWIW, I've found every major change in my career to be a positive shift. Some might say it's just my perspective (i.e. perhaps I'm making lemonade out of lemons), but I think there's a very real way in which changes, made for the right reasons, are of course likely to yield benefits given selection bias (i.e. that's presumably why you chose a specific change in the first place).

Far more importantly than choose the right change, though, is probably the wisdom to differentiate which changes are reversible vs. not (i.e. "one-way doors"). It's far more important to be sure about the latter, whereas in the former case, it behooves you to simply take action quickly and be ready to change again when things don't go the right direction.

Most of my career could not have been predicted from the outset. So in a very real way, nearly all of it has "paid off in direct or surprising ways." I truly wish you the same.