From Skyscrapers to Garages

Why I Left Investing for Rockets

Alexander Kwan
5 min readFeb 1, 2021

Four years into my career in private equity, I was developing a pretty advanced case of imposter syndrome. I sat in an antique adorned conference room on the 78th floor of one of Hong Kong’s landmark neon skyscrapers.

Hong Kong: Office harbor views with crushing rents

Sitting across the table from me was a mobile tech entrepreneur. I was hard selling a vision, trying to convince him to enter into a business joint venture with one of my portfolio companies, a large retail real estate asset manager. He’d get access to some of the highest-end malls across Asia, if he assigned the JV exclusive licensing rights of his technology.

With 15 years of experience on me, he was skeptical of the (admittedly draconian) terms of the deal and had reservations on the exclusivity. I argued that the combination of my firm’s capital and real estate network, alongside his company’s technical acumen would enable us to create a successful online-to-offline retail rewards company. I talked a lot about pies: shares of pies, growing pies, blueberry pies. I projected a wizened sense of knowing what it took to build great businesses — yet, in reflection, I clearly didn’t know what I was talking about.

During the course of my career in investing and advisory, I had only really worked with established companies, and had primarily focused on executing financial outcomes, rather than scaling a product or operations. I lacked exposure to true start ups. So I really wanted this JV to be signed. See, I had sourced the deal and, if it went through, I would be positioned to personally help create its strategy and run it.

But the deal fell through. In the end, the entrepreneur deduced that it wasn’t in his company’s best interest, and would focus on building this new business organically, as he had done with his other companies for more than a decade.

Fearing that my lack of hands-on business experience would eventually expose me, I started to look at business schools back in the United States. I was motivated to switch to a role within a company, where I could get the entrepreneurial experience that I so desperately craved. Enamored with tech startups, I told myself I’d go work at the hottest company out there.

When I told my boss I was leaving for B-School he grinned and said:

“You know that people go to business school to get jobs like yours?”

Finance professional coveting the greener pastures of rose-tinted tech — I know, not a very unique story.

Landing at SpaceX

Weighing admission offers in Los Angeles and New York, I chose to attend UCLA Anderson in order to find a way to network my way into Hawthorne-based SpaceX. Elon had given a speech on Falcon 1’s hardships and eventual success at the University of Pennsylvania during my undergrad, and I had followed his ascent ever since.

1952’s “Explorers on the Moon”

SpaceX was all over TechCrunch and the NYTimes in 2013 with Falcon 9’s spectacularly fiery landing attempts. I was captivated by the practical audaciousness of it — a rocket that could land had seemed so sensical to me ever since I had read TinTin as a kid.

I told my new classmates that SpaceX was my only real target. They’d chuckle skeptically, but I was determined. As a complete newbie to space, during business school I set out to work with a couple satellite startups to amass enough jargon to finagle my way into a gig with SpaceX’s Commercial Sales and Business Development team. Luckily, they took a flier on me and bit.

Entering SpaceX, I had a naive preconception that I’d be joining a start up where I could learn how the “successful company” sausage was made and have an outsized impact on its recipe. This illusion soon dissolved after I received my first mission flight patch in December 2015, which was serendipitously for Falcon 9’s first successful landing. It listed my employee number in the 5000s.

While I was blown away by its spectacle and energy, SpaceX was a start up in culture, but an established company in structure. It was already built, with all roads paved, all street lamps lit, and all tales (and parties) of a big city. Countless others had built the Company long before I arrived.

SpaceX: Big Holiday Parties with 10,000 attendees

Enter Relativity Space

Giving a tour one day of the rocket factory floor to a VC mentor of mine, I lamented that while I had landed at my dream company, I was worried if it was the right longterm fit for me. His eyes lit up and he shared that he had just been at Y Combinator Demo Day. A couple of young aerospace engineers had pitched a 3D printed rocket and had stolen the show. They were starting a Series A financing, and could use an investor-minded set of eyes on their diligence materials. He’d make the intro.

I met with the two co-founders of Relativity, Tim and Jordan, in a nondescript, beige warehouse in San Carlos where their sawhorse desks were surrounded by metal 3D demo prints, small robotic arms, and CAD schematics of a rocket. They had just raised seed funding from Mark Cuban Companies and Y Combinator, and had fantastically big plans to build the world’s largest metal 3D printer to manufacture and launch a rocket. They took me up on my offer to help on their upcoming raise, and I set out talking about the dynamics of the satellite market to prospective investors and copy editing one pagers.

Two months later, they had a signed a term sheet and were planning to move Relativity down to LA. Tim, Relativity’s CEO, and I grabbed coffee in Venice, and while we caught up, he measuredly declared, “It makes the most sense for you to join us now.” Trying to contain my excitement, I shifted our conversation onto what we needed to do first. He replied, “We need a hundred miracles to make this work, and you can start on most everything non-engineering that entails.”

To say I ran toward this opportunity would be an understatement. I sped toward it in a high speed chase involving the CHP and a helicopter. I jest. But here, at Relativity Space, was exactly what I was looking for — a blank canvas. I could learn on the job and by doing.

After having felt like an imposter throughout my investing career, I could finally take my shot at building a business. I mean, with a MBA and my investing background, how hard could it be? …I may have lacked the imagination.

Next: “Non-Engineer at a Rocket Start Up: Mapping out Business Operations”

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Alexander Kwan

Starting something new | Ex-Head of Finance and Business Operations at Relativity | Ex-Private Equity