This week, I talked to some students at Duke about:

• My journey from Minnesota to Silicon Valley

• How to find a job you love

• The recent miracles achieved by the space industry

• My deficiencies as a supply chain manager

Huge thanks to Jackson Kennedy for making this possible! Full transcript, edited for clarity and brevity, below.

Good evening all, and welcome to Engineering Entrepreneurship: a Startup in Space. My name is Jackson Kennedy, and I'm here as a representative of the Duke AERO Society talking with Christian Keil.

Christian is the Chief of Staff at Astranis and writer of Silicon Valley Outsider. He did his undergrad at the University of Michigan, earned an MBA from UC Berkeley, worked as a consultant at Deloitte, was the co-founder of the Tuesday Company, founder of Direct, and joined Astranis in 2019.

Astranis builds geostationary satellites to deliver internet connectivity and can do it cheaper and better than its legacy competitors due to a variety of technical improvements. Tonight we'll talk about his path to Astranis, thoughts on new space, advice for students, and trends to follow.

Thank you so much for joining us tonight, Christian.

Well, thanks so much for organizing this Jackson. I plan to spend most of this time in question and answer, but figured it'd be good to tell you a little bit about what sorts of questions I might be good at answering.

I have a blog today called Silicon Valley Outsider, and I'm currently living in San Francisco. I came here because I wanted to be a part of the crazy startup thing.

I didn't have a space background, I didn't have a technology background — I'm a business person, I was an economics major in undergrad, but I was always interested in startups. Silicon Valley was this mythical place that could make me the next Steve Jobs, and then I'd be famous and rich and happy. That was the plan.

Where Silicon Valley brought me, though, was to space. I ended up finding this amazing company called Astranis that was doing something that I literally didn't even know existed: satellite internet.

In the beginning, I grew up in the Midwest. I'm originally from Minnesota, and after I graduated from Michigan with a couple of business degrees, I went back to Minnesota to become a management consultant.

Management consulting basically is people who get airdropped into the biggest companies in the world to help them. It was my job for my first couple of years after undergrad, and most of the work I did was with telecommunications companies (AT&T, Verizon, Sprint). It was a great way to learn about a ton of different things — like “what is business?” My degrees didn't teach me a whole lot about what business was in the real world, but Deloitte did.

A really important thing I learned near the end of my time at Deloitte was that my preferred incentive model was different from what works for most consultants.

At Deloitte you would get a rating at the end of each year. Everyone there is such a gunner, they're all high achievers, and everybody was gunning for the best scores that they could get. An unfortunate by-product is that you needed to do two things to get a high rating: good work, and networking, aka going to people and telling them how good your work is.

Around year two, I wasn’t doing as well as I thought I should, and figured that I should do an experiment. In year one, I would try as hard as humanly possible: pour myself into my job, and absolutely crush it as hard as I could, but ignore the networking stuff. And then in year two, I would not work hard, but I would network my brains out, tell everybody how smart I was, and try to find connections to the right people.

And lo and behold, in the second year, I got a higher performance rating than I did in the first.

At that point, I figured out the game — I had hacked the code. And I could have just stayed there, I suppose, but that wasn't what I was trying to do. I wanted to be at a place where super hard work was rewarded and you didn't have to tell people how cool you were.

I was looking for something different, and my hypothesis was that it would be in Silicon Valley.

I took the most risk averse way to move to Silicon Valley: going to business school. I ended up getting into Berkeley, which is a really great school that’s not full of a bunch of stereotypical business school students. Berkeley’s thing is “Confidence Without Attitude.”

Berkeley was a great way for me to move to San Francisco and to learn everything about Silicon Valley. I was an intern at a VC firm, and I started my own company.

This is a picture of me as an MBA student, and I'm pitching at a blockchain event.

I did as much as I could to try to make it work, but it was ultimately a beautiful failure.

I learned so much from those experiences. What they taught me was that I was absolutely in the right place. Even in failure, I wanted to do startups even more… even though it wasn’t the Steve Jobs scenario that I had dreamed up.

Once it became clear that my startup was winding down, I started looking and I started looking far and wide for companies that I thought would be a good fit. I knew a lot about telecom and I wanted to find a startup in that space, and the first company that I found was Astranis.

It was doing telecom in space, which was so cool, and the idea was to bring internet to the next 4 billion people that don't have access to it, which is perfectly mission-aligned for me. And I hoped that Astranis would be a rocketship startup: you join when it's small, and then it gets really big and you get to be there for the whole ride.

But unfortunately, Astranis rejected me.

I applied and they said no. And that just threw my whole plan up in the air. I was like, “What the heck? This is the perfect company for me, and I know that I'll be good at it.” But they wanted somebody who had a ton of supply chain experience, like twenty years of managing vendors and negotiating with them. So it wasn't meant to be that first go around.

But then, of course, after a very long and painful process of applying to a million companies and getting rejected, I finally got an offer at a different company. It was set to expire in two weeks, so I went back to Astranis and begged them to take me. And miraculously, it all worked out.

Since then it's been an absolute miracle. Last April, we raised $250 million at a $1.4 billion valuation. We now have over 200 employees, we've hired 120 people in the last eight months, we've moved into this new facility. It's crazy. It's actually happening.

The dream that I had moving to Silicon Valley is actually coming true. Fully recognizing that I've been extremely lucky — but it can happen. And as long as you know what you're getting into, startups can be a great bet for your career.

Great. Thank you so much for the intro. We have a couple of questions lined up and I definitely encourage everyone to submit their questions. I see we have one already.

I wanted to ask a little bit more about the role of Chief of Staff and what have been some successes that you've had, and what's been your toughest day on the job.

The Chief of Staff role is a very interesting one. I actually wrote about it this week in Silicon Valley Outsider.

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6 days ago · 1 like · 4 comments · Christian Keil

After reflection, I think that the reason why the role is so confusing is because it is a service role. The Chief of Staff role is not independent. I don't have any authority of my own. Yet I'm a “chief” officer of the company, one of the leaders, and I'm on the executive team.

It is my job to be the Chief of Staff for the CEO, and to make the CEO better in everything that he does. And what does a CEO do? No one knows what a CEO does. They just run a business, right? They do everything.

And in the same way [as the CEO], the Chief of Staff just runs a business and does everything — all in support of this other person.

It's my job to know my CEO better than anybody else knows him, to know his strengths and his weaknesses, to know the places that he's looking and the places he's not looking. And then I either supplement or compliment that to the best of my abilities.

The role pushes your skills and abilities to the max. And that's where a lot of those bad days come from. I'm constantly way out over my skis and leaning as far into the job as I possibly can. There are definitely some times where I've crashed and burned, trying to do things that are either beyond my skill set or just hard. And it's just painful to run a company. Elon Musk famously said:

It's the most grim quote of all time, but if you're here and you see what it's actually like to have 200 people's jobs ride on your ability to execute on whatever task, and to do it without help… that's scary.

One thing I was really interested in is you used the term “beautiful failure” earlier. What does beautiful failure mean to you?

In my life I've optimized for how fast I can learn things. I just want to learn all the time. I want to be good at everything.

I wanted to find a way to learn as fast as humanly possible about: 1) what startups are, and 2) how to be good at them. I wanted to be a 90th percentile start-up performer as fast as humanly possible.

The thing that taught me way more than anything else was just being there and doing the thing: trying to raise money, trying to put together a team, and trying to convince AT&T and Verizon that me, a dude with a PowerPoint deck, could solve their problems. It was crazy.

One of the most interesting parts of that whole failure was the fact that my idea worked. There's a company that is currently doing exactly what I was trying to do that.

That's a really interesting thing about startups: you can be exactly right with the idea and still fail if you don’t execute well enough to get the job done.

The fact that I started a failed startup was a huge thing in my favor when applying to jobs. People thought it was great experience and that I would be way better on the job, as opposed to if I just twiddled my thumbs in business school.

Speaking of being a generalist, there was a question about wanting to exit consulting. When you were getting into consulting, did you plan to exit so soon? Did it just happen? And how did people at tech look at you coming from consulting?

When I joined consulting, I was sort of an unserious person.

Kids these days are crazy. Like there are students that I know now that are at one internship, already recruiting for the internship the next summer.

And I was the opposite. I was not that serious when I was a college student or even right when I graduated. I got so lucky landing in consulting. I can't claim to have had a master plan at that point.

I definitely became a more serious person throughout being a consultant. Particularly in that second year, when I got like a bad performance rating, I had a crisis of the soul moment where I thought I was a failure and was wasting my life.

My solution at the time was to pour myself into goals. To create a crazy bucket list and just tick down them as fast as possible: run a marathon, write a book, and learn Spanish. And I really committed myself to doing them, achieved the goals, and at the end of it, I was still the same person with the same self doubt. But at least by the time that I left, I was leaving consulting for a very intentional reason.

To answer the second half of your question: consulting is fine, but people don't like MBAs out here. There's a bit of degree elitism for sure. The MBA is like ultimate non-technical degree: it's a bunch of hot shot, young people who want to leave and then become the strategy lead of something.

Astranis has both hardware and software. It's a very technical company. And if you've had to learn any of those skills, how did you try?

Today, I am starting a program to try to build my technical skills. Is that necessary? Yes and no. I've definitely helped my company, even though I am a non-technical person.

I understand our technology pretty well; if you're just smart, you can figure out a lot of stuff. But I certainly lack a specialty. Everybody at Astranis is T-shaped: they have a base level of understanding about everything and then they're super specialized in one area. But I certainly lack a specialty. You definitely have to be at least technically literate.

When you're looking for a job, it's a two-way search, right? So you're looking for the best fit for you and they're looking for a great fit for them. When you were looking for that perfect rocket ship company.

Were there any particular qualities you were searching for? Did you have a checklist or was it really a gut-feel?

There was what I was looking for and what I found. And those were two different things. What I was looking for was a startup at a particular stage.

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a year ago · Christian Keil

I wanted there to be an existing product and an existing technical team, because I had just personally experienced being that lone person in the garage without a team. And I was like, “please give me some backup.”

I was looking for a Series A company, because I figured there was a lot still to build and I'm a generalist.

But then I found a bunch of other stuff at Astranis that I just couldn't have imagined. I was one of the first business people, but like the 50th member of the company. There was a huge technical team. And that ratio was awesome. That was amazing for a business person to come in and have super high leverage.

Another question is what helped you build a network outside of business school, which I imagine helped a lot to start a startup as a new person in the valley.

There was no secret. It was just a whole lot of hustle and that's what Silicon Valley rewards. There's tons of communities of founders, and this whole entire place is built around trying to get people from anywhere to be able to start a Silicon Valley startup.

Maybe one thing that you could do to cut the line is to find somebody else who's already doing a startup you find interesting.

When I started my startup, I wanted to be the main character.

I was going to be the founder, and I was going to have the idea — and that was a self-centered way of starting a company.

But it doesn't have to be like that. You can go and tap into existing networks of technical people, for instance, or find communities that are trying to collectively build companies.

It sounds like you learned on the job how to be a Chief of Staff and in a new industry, that's high pressure. Did you network with other Chiefs of Staff at other organizations to figure out how to do it?

Totally. I mean, you have to, and one of the biggest and most important things you can do in Silicon Valley is learn from the other startups.

For all the talk that Silicon Valley is about first principles thinking, it is very interested in learning about what other successful startups are doing.

We're not listening to the outside world, but we're all talking to each other.

And that's a really cool thing to witness in person. And it's a big part of my job now. Whenever we're doing anything we haven't done before, I'll go out to Chiefs of Staff and I'll say, “Hey, you're at a similar company to me, we're doing this thing. I think you probably did this because you're a little bit bigger than us. What did you do? What worked? What didn’t work?”

That's one of the best reasons to start your own company if you're trying to learn about startups: you have plausible deniability to reach out to people for a real reason, as opposed to “let me pick your brain.”

Do you have any suggestions to help deal with the pressure of a startup, any ways to make the glass more appetizing or the void a bit brighter?

That's awesome. That's such a good question.

[It’s so good, I’m going to write about it next week! No spoilers in this transcript.]

You wrote an excellent Silicon Valley Outsider piece on choosing a startup versus big company X. And I was hoping you could talk about that a little bit for the attendees.

There's many, many, many dimensions on which you could like or dislike a job:

• You could really like the working style: are the people staying up late at night and working into the wee hours of the morning, or are they strictly nine to five?

• You could be a fan of their communication style: are they going to pick up the phone and call each other, or Slack, or email? Are they going to schedule meetings for everything or nothing at all?

• You can like the incentive structure. This is what I talked about with consulting. Consulting incentivized certain behaviors; startups incentivize certain behaviors.

• You can like the problem the company is trying to solve. One of my best friends from Deloitte went to Tesla because his biggest thing that he cares about in the entire world is the environment.

• You can like the people you work with, and have a style that really meshes with your boss.

Across all those dimensions, you should have opinions.

What are your opinions about all those things? It's extremely hard to just think about it and come up with the right answer.

If I ask you right now: would you rather be at a company that has super immediate communication or a super asynchronous communication? You might not think about all the ways that it actually affects you in practice. Immediate communication sounds better until someone’s calling you at 7:00 PM and you're like, okay, I'm just trying to have dinner.

Once you have those opinions, you'll notice that there are trends of where you can find those things at different companies. The size of the company matters.

At a big company, things will be more asynchronous. Things will take longer to do. You'll be a part of a bigger team. You'll get more mentorship, because there's more people at the level right above you. You'll get less responsibility because there'll be more people that are experienced and doing the things already. And there'll be a lot more structure. So your career path will be super well-defined and you'll know that at two years, I'm going to get promoted — and even if I'm awesome, I can't accelerate it, but if I stink, I can't decelerate. Maybe that sounds awesome. Maybe you're the kind of person who learns best from being taught.

But maybe you are the opposite. At a small company like a startup, you're just thrown into the problems. There's much less structure, so there's not as much overhead. You can make bigger mistakes. And you get to learn by experience because you're getting real work to do from day one. Your actions will be known. You can't hide.

I wouldn't say there's one thing that's best. It's all about finding your preferences.

How is Astranis responding to the launching of Starlink, which brings into some of the intricacies of a certain value proposition?

We're celebrating it to be totally honest. Starlink is a miracle. It is super cool.

Traditionally, for satellite connectivity, you would put a big, huge satellite really far away from earth. Rocket launches were super expensive, so to justify the cost of that launch, you put a huge satellite really far away, and it covers a third of the earth and it hovers there.

The benefit to that is that you can do it with just one satellite. The cost of that is that the satellites are really expensive and they take forever to build. And they're so far away that literally the speed of light takes a while to get there and back.

The Starlink idea is to put satellites closer to earth. Then the main benefit is that that latency is lower because light doesn’t have to travel so far. The trouble is when you put satellites closer to earth: 1) after 3-4 years, they’re going to fall back into Earth's atmosphere and burn up, and 2) you need a ton of them. You need like hundreds or thousands of these satellites, cause they're whipping around the earth at massive speed. It's kind of like the International Space Station. You can see it flying in front of the moon; it's moving relative to somebody on the ground.

So the fact that Starlink has succeeded in putting up almost a thousand satellites is a miracle. And they deserve all the accolades they can get, because that is such a cool achievement. But in my mind, it's sort of the same thing as the big satellite model. The big satellites costs hundreds of millions of dollars and take years to build. And Starlink costs billions of dollars and took many years to build.

Our idea is to make the big, stationary satellites really small. Instead of covering the whole earth, they just cover a country.

Our basic insight is that every telecommunications project to date has been a mega project. It's either you're laying fiber for billions of dollars, or you're putting a satellite up for billions of dollars, or you're putting a constellation of small satellites up for billions of dollars.

It's all mega projects. But Astranis is building micro satellites.

We're building small ones to target them exactly where they're needed. We can put things up for much less cost. And then in the end, we can charge less to each user.

Starlink offers $99 plans across the entire world, no matter where you are. And that is a miracle. There are so many people that are gonna use that — if they can afford it. But in a country like Peru, where we’re launching a satellite, people only spend three bucks per month on internet.

So our value proposition is different. We can still make money when we offer conductivity for that cheap.

In the ambiguous Series A environment, how do you find and stick to what's important to do and remain true to your values?

That’s something I've taken for granted at Astranis. A lot of software companies, have the ability to anything. There's a million different places they can focus.

But Astranis has been extremely focused from day one. It's probably traceable to the fact that all of our resources were just dedicated on building literally one physical object for one customer. That's super weird. Not normal at all for startups.

Now we're building four additional satellites: one for Peru, two for the United States, and one that we haven't announced yet.

The world is now our oyster. We have much more that we can do with all the satellites because we're building them at a higher rates. So ask me again in like two years and I'll have a much better answer because for now we're just like Alaska, Alaska, Alaska, Alaska.

So one issue that I imagined may have popped up very recently is the global supply chain. And how in the world has Astranis been coping with those disruptions?

Well, as I mentioned before, I was not hired for the supply chain role, so I'm probably the worst person to ask.

Well, I just wanted to ask one final question as we're wrapping up. You've mentioned Steve jobs a couple of times, but who's really inspired you throughout your journey. Have there been any great books you read and just in general, who do you look to?

I've read every book that I can get my hands on about Silicon Valley.

As I mentioned, I had this weird, manic phase that I started eight years ago when I was in consulting. And ever since then, I've tracked every single book I've read and they are all on my website, PronouncedKyle.

That's a huge source of information and inspiration for me. I love reading.

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9 months ago · 1 like · Christian Keil

But beyond books, a lot of my inspiration these days comes from other entrepreneurs and people who are a little bit more advanced than me.

I'm finding more inspiration from people who are less traditionally “inspirational.”

I find that it's just not that helpful for me to look at people that are like Elon Musk or Steve Jobs because the distance between me and them is so unfathomable. It’s like you're on one continent, looking across to someone in Europe, and you're like, okay, how do I get there? There's a million ways.

What I found more helpful is finding people that are just one or two steps ahead. One of my friends who was a Chief of Staff just started his own company; he launched literally yesterday, I think, or two days ago. It’s called Seis. It’s a Spanish-language-first bank. And he’s hiring, so go apply if you’re interested.

I don’t know if founding a company actually interesting to me; I know exactly how hard it is now, and maybe I don't want to do it, but he's a great example.

My closing ask to you all is to go find those people.

If you're interested in going to Silicon Valley, or working in new space, I can be one of those people that's there for you. I’m an actual example of a real human that’s a couple steps in the direction that you want to head.

But if you don't want to go into Silicon Valley or space, who are those other people? Who are those real people that you can point to and say, “yeah, from me to them, I have to do this. That's exactly what they did. So I'll just go do it.”

Don't look too far in the future. Don’t say you want to be Steve Jobs, because how the hell does anyone know how to become Steve Jobs?

But it isn't that hard to become me. I know exactly how ended up in my spot. So if this sounds interesting, subscribe to Silicon Valley Outsider and I'll teach you how I did it.

Thanks for reading Silicon Valley Outsider! I’m Christian, the Chief of Staff of Astranis, and I write this newsletter for folks who are interested in startups and live outside of the SF Bay Area. Subscribe now to join 600 people in getting an email from me each Monday.