Arianna Simpson

Zimbabwe's hyperinflation: currency lost 50% of value daily

Simpson explains that under Robert Mugabe's reckless money-printing, Zimbabwe's currency devalued by 50% on a daily basis at its peak, wiping out savings and emptying hospitals and stores. The experience sparked her interest in non-state currencies.

“And so what this caused was massive hyperinflation, which at its peak had the currency devaluing by 50% on a daily basis. So basically people's savings were completely evaporating. Stores were not able to keep any merchandise in stock. Hospitals could not stock medicine. Doctors were not getting paid. People were dying from very preventable things.”

Bet on explosive upside, not managing downside, when you're young and broke

Simpson's rationale for going all-in on Bitcoin: when you're young with little to lose, asymmetric upside beats protecting a small downside. Losing half a small net worth is recoverable; being right about a generational bet is not.

“To me, I've always felt that it was more interesting to have explosive upside potential than managing downside risk. And so I was like, okay, I'm quite young. I don't have that much money to begin with. I think this is incredibly powerful and important, and most of the world has not yet caught on to this fact. And if it goes to zero, well, whatever, I've lost half of my net worth, but it wasn't that much to begin with, and I'll make it back over the course of my life slash career.”

Steal thisWhen young and low on capital, size bets for asymmetric upside instead of preserving a small downside.

Arianna Simpson cannonballed 50% of her net worth into Bitcoin

Early-stage investor Arianna Simpson recounts that her first Bitcoin purchase, around 2013-2014, was 50% of all the money she had in the world at the time.

“It was, I won't say the number, but it was 50% of the money I had in the world at the time.”

KKR partner's model: Bitcoin worth $200K-$800K per coin

Simpson cites John Pfeffer's paper 'An Institutional Investor's Take on Crypto Assets', which models Bitcoin penetration of M1 money supply and backs into a $200K-$800K per coin valuation. (Episode aired 2019 when BTC was ~$10K.)

“And basically he does the math looking at what is M1 money supply, what if Bitcoin achieves, you know, 10%, 50%, 100% penetration of these various kind of segments of the money sphere that you could look at. And he backs into a $200K to $800K-ish prediction or, you know, potential.”

KKR partner's model: Bitcoin worth $200K-$800K per coin

Simpson cites John Pfeffer's paper 'An Institutional Investor's Take on Crypto Assets', which models Bitcoin penetration of M1 money supply and backs into a $200K-$800K per coin valuation. (Episode aired 2019 when BTC was ~$10K.)

“And basically he does the math looking at what is M1 money supply, what if Bitcoin achieves, you know, 10%, 50%, 100% penetration of these various kind of segments of the money sphere that you could look at. And he backs into a $200K to $800K-ish prediction or, you know, potential.”

1,800 applicants for the Facebook sales role she landed

Simpson says the hardest part of working at Facebook was the interview gauntlet: roughly 1,800 applicants and 8 rounds of interviews for the job she got. The job itself was easier than her prior startup work because she was selling a known product.

“I mean, frankly, the hardest part of working at Facebook was by far the interview process. So there were about 1,800 applicants for the job I ended up getting, which is, you know, very, very low percentage hit rate.”

Waking up terrified of complacency pushed her to quit Facebook

Despite a comfortable, well-resourced job, Simpson woke up every morning afraid she'd make nothing of her life by getting too complacent. Getting deep into Bitcoin gave her the push to leave faster than she otherwise would have.

“I remember waking up every morning terrified that I was going to make nothing of my life in terms of what I wanted to do because I would get too complacent. It was a distinct— like every morning I had that feeling. And so I knew I needed to leave. I think I probably wouldn't have left as quickly as I did if I hadn't gotten really into Bitcoin.”

Blog post that turned into a BitGo job offer

Simpson wrote a blog post about multisignature wallets, mentioned BitGo in it, then emailed it directly to the CEO. That cold outreach led to lunch, then a surprise job offer making her employee number 3.

“And so I wrote a blog post about it and mentioned the company in the post. And then because I'm a little bit shameless, I just emailed it to the CEO and I was like, "Oh, you might want to publish this on your blog." And they were like, "Who is this girl?" And so then they were like, "Oh, this is quite good. Would you like to come have lunch?"”

Steal thisPublish a sharp piece about a company, then email it straight to the CEO as a warm-up for a job.

Minimum-credentials thinking: what's the least I need to do this?

Simpson's default question before any goal is the minimum knowledge or credentials needed to accomplish it, rather than over-preparing first. She argues confidence, not skill, is usually what's missing.

“I think oftentimes, like my approach has generally been, what is the minimum amount of knowledge and/or credentials I need in order to accomplish this thing rather than the other way around? And I, I think, you know, the world has room for a lot of different types of approaches, but I think oftentimes that is lacking is, is confidence more than any actual skills.”

Steal thisAsk the minimum knowledge needed to start, then start; assume confidence is the real gap, not skill.

Pick an emerging niche where you can research your way to expert

Simpson's playbook for fast credibility: choose a new field with no established experts (crypto in 2013), so genuine research makes you one of the few authorities. In a mature field, someone with 20 years of track record always outranks you.

“So in my case, because I was interested in Bitcoin and crypto and there were like 4 people— no experts yet. No experts. Exactly. It was a much faster ascent, if you will, because if you knew some stuff and you had done your research, which I— to be clear, it's not like— you have to know your stuff.”

Steal thisGo deep on a brand-new field with no incumbents so research alone makes you a recognized expert.

Twitter drove 25% of her career success and LP money

Simpson credits at least 25% of her career success to Twitter, including landing LPs and investments directly from the platform. She favors tweetstorms over blogging because she'll actually do them rather than wait on a 'magnum opus'.

“I've had LPs from Twitter. I've had— investments come from Twitter. I've like, honestly, I probably, I could ascribe 25% of my career success at least to Twitter.”

Steal thisPublish your thesis publicly and consistently; ship tweetstorms instead of waiting for the perfect essay.

Zach Park: Kickstarter hustler who replied to a cold email in minutes

Cubcoats co-founder Zach Park raised millions across Kickstarter campaigns and built an online presence as a self-evident hustler. Simpson cold-emailed him offering a value trade; he replied within minutes because, unlike the hundreds of cold emails he got, hers offered something back.

“And he wrote back within a few minutes and was like, I get hundreds of cold emails. Like, nobody ever offers anything back. Right. And that was why he reached out. And so we ended up meeting and became very good friends. Now I'm an investor in the company.”

Steal thisIn a cold email, lead with what you can give, not what you want; it's why you'll get a reply.

Don't 'pick your brain' — lead with a specific question

Simpson's advice for reaching out to busy people: skip 'hi' and 'can I pick your brain' (overplayed, gets ignored among hundreds of messages weekly) and open with a specific question to build rapport.

“I would encourage people not to say, hey, let me pick your brain, because I think that's a little overplayed. And I think if you start with a specific question, it's a better way to kind of build rapport and kind of go from there.”

Steal thisWhen DMing someone busy, open with one specific question instead of 'hi' or 'can I pick your brain'.