Substack

My First Exit

James BaileyLeave a comment

I invested in my first private company in 2022; my first opportunity to cash out of a private investment came this year when Our Bond did an IPO, now trading on Nasdaq as OBAI.

I’m happy to get a profitable exit less than 4 years after my first investment, given that I’m investing in early-stage companies. Venture funds tend to run for 10 years to give their companies time to IPO or get acquired, and WeFunder (the private investment platform I used) says that “On average, companies on Wefunder that earn a return take around 7 years to do so.” The speed here is especially striking given that I didn’t invest in Our Bond itself until April 2025.

Most private companies that raise money from individual investors are very early stage, what venture capitalists would call “pre-seed” or “seed-stage” companies looking for angel investors. Later-stage companies often find it simpler to raise their later stages (Series B, et c) from a few large institutional investors. But a few choose to do “community rounds” and allow individuals to invest later. This is what Our Bond did right before their IPO, allowing me to exit in less than a year.

This helps calm my biggest concern with equity crowdfunding- adverse selection:

The companies themselves have a better idea of how well they are doing, and the best ones might not bother with equity crowdfunding; they could probably raise more money with less hassle by going to venture funds or accredited angel investors.

My guess is that the reason some good companies bother with this is marketing. Why did Substack bother raising $7.8 million from 6000 small investors on WeFunder in 2023, when they probably could have got that much from a single VC firm like A16Z? They got the chance to explain how great their company and product is to an interested audience, and to give thousands of investors an incentive to promote the company. Getting one big check from VCs is simpler, but it doesn’t directly promote your product in the same way.

All this is enough to convince me that the equity crowdfunding model enabled by the 2012 JOBS Act will continue to grow.

Still, things could have easily gone better for me, as these markets are clearly inefficient and have complexities I’m still learning to navigate. Profitability is not just about choosing the right companies to invest in, but about managing exits. I expected the typical IPO roadshow would give me months of heads-up, but Our Bond surprised its investors with a direct listing. The first thing I heard about the IPO was a February 4th email from “VStockTransfer” that I thought was a scam at first, since it was a 3rd-party company I’d never heard of asking me to pay them money to access my shares. But Our Bond confirmed it was real- VStockTransfer was the custodian for the private shares, and charges $120 to “DRS transfer” them to a brokerage of your choice where they can be sold.

I submitted the request to move the shares to Schwab the same day, but Schwab estimated it would take a week to move them. Neither Schwab nor VStockTransfer ever sent me a notification that the shares had been transferred, and by the time I noticed they had moved a week later, the stock price had fallen dramatically:

As I write this on February 18th, the OBAI price represents a 1.3x return on the price I invested in the private company at last April. When I was first able to sell some stock on February 11th, the price represented a 3x return; if I’d been able to sell right away on the 4th without waiting for the brokerage transfer process, it would have been a 10x return.

By the Efficient Market Hypothesis this timing shouldn’t be so critical, but I knew there would be a rush for the exits as lots of private investors would want to unload their shares at the first opportunity, an opportunity some would have waited years for. Sometimes old-fashioned supply and demand analysis is a better guide to markets than the EMH: demand for OBAI stock had no big reason to change in February, but freely floating supply saw a big increase as private shares got unlocked and moved to brokerages.

Getting a 10x return vs a 1.3x return on one of your winners is the difference between a great early investor and a bad one. I always thought such differences would be driven by who picks the best companies to invest in, but at least in this case it could be driven by who is fastest on the draw with brokerage transfers.

If I ever find myself holding shares in another company that does a direct listing, I’ll be doing whatever I can to make sure the transfer goes as fast as possible (pick the fastest brokerage, check on the transfer status every day, et c). This process also seems like one reason to do fewer, larger private investments- a fixed $120 transfer fee is a big deal if the initial investment was in the low hundreds but wouldn’t matter much for a larger one.

Being accredited would help there, allowing access to additional later-stage, less-risky companies. But I’ll call OBAI a win for equity crowdfunding, and a big win for asset pricing theories based on liquidity and flows over efficient estimation of the present discounted value of future cashflows.

Disclaimer: I still hold some OBAI

Woodstock for Nerds: Highlights from Manifest

James Bailey4 Comments

I’m back from Manifest, a conference on prediction markets, forecasting, and the future. It was an incredible chance to hear from many of my favorite writers on the internet, along with the CEOs of most major prediction markets; in Steve Hsu’s words, Woodstock for Nerds. Some highlights:

Robin Hanson took over my session on academic research on prediction markets (in a good way; once he was there everyone just wanted to ask him questions). He thinks the biggest current question for the field is to figure out why is the demand for prediction markets so low. What are the different types of demand, and which is most likely to scale? In a different talk, Robin says that we need to either turn the ship of world culture, or get off in lifeboats, before falling fertility in a global monoculture wrecks it.

Play-money prediction markets were surprisingly effective relative to real-money ones in the 2022 midterms. Stephen Grugett, co-founder of Manifold (the play-money prediction market that put on the conference), admitted that success in one election could simply be a coincidence. He himself was surprised by how well they did in the 2022 midterms, and said he lost a bunch of mana on bets assuming that Polymarket was more accurate.

Substack CEO Chris Best: No one wants to pay money for internet writing in the abstract, but everyone wants to pay their favorite writer. For me, that was Scott Alexander. We are trying to copy Twitter a bit. Wants to move into improving scientific publishing. I asked about the prospects of ending the feud with Elon; Best says Substack links aren’t treated much worse than any other links on X anymore.

Razib Khan explained the strings he had to pull for his son to be the first to get a whole genome sequence in utero back in 2014- ask the hospital to do a regular genetic test, ask them for the sample, get a journalist to tweet at them when they say no, get his PI’s lab to run the sample. He thinks crispr companies could be at the nadir of the hype cycle (good time to invest?).

Kalshi cofounder Luana Lopes Lara says they are considering paying interest on long term markets, and offering margin. There is enough money in it now that their top 10 or so traders are full time (earning enough that they don’t need a job). The CFTC has approved everything we send them except for once (elections). We don’t think their current rule banning contest markets will go through, but if it does we would have to take down Oscar and Grammy markets. When we get tired of the CFTC, we joke that we should self certify shallot futures markets (toeing the line of the forbidden onion futures). Planning to expand to Europe via brokerages. Added bounty program to find rules problems. Launching 30-50 markets per week now (seems like a good opportunity, these can’t all be efficient right?).

There was lots else of interest, but to keep things short I’ll just say it was way more fun and informative doing yet another academic conference, where I’ve hit diminishing returns. More highlights from Theo Jaffee here; I also loved economist Scott Sumner’s take on a similar conference at the same venue in Berkeley:

If you spend a fair bit of time surrounded by people in this sector, you begin to think that San Francisco is the only city that matters; everywhere else is just a backwater. There’s a sense that the world we live in today will soon come to an end, replaced by either a better world or human extinction. It’s the Bay Area’s world, we just live in it.

Is Equity Crowdfunding Beating Adverse Selection?

James Bailey2 Comments

Most new businesses are funded with a combination of debt and the owners’ savings; equity funding has traditionally been relatively rare:

Source: Kauffman Foundation

Partly this has been a regulatory issue. Raising equity adds all sorts of legal burdens. Traditionally businesses could only accept equity investments from accredited investors and a small number of friends and family unless they did a full IPO and became public (hard enough that there are less that 5000 public companies in the US out of millions of businesses). This changed with the JOBS Act of 2012, which allowed small businesses to raise money from large numbers of non-accredited investors without having to register with the SEC.

Following the JOBS Act, equity crowdfunding sites like WeFunder emerged to match new businesses with potential investors. But equity crowdfunding has taken off relatively slowly:

Total dollar amount raised by regulated CF crowdfunding campaigns. Source: FAU Equity Crowdfunding Tracker

Its seen more success recently with some additional regulatory relief and the overall market boom of 2020-2021. But at ~$400 million/yr, its still well under 1% of all venture investment (~$300 billon/yr), which is itself tiny relative to the public stock market ($40 trillion market cap).

Why has equity crowdfunding been slow to take off? Partly its new and most people still don’t know about it. Partly early-stage companies aren’t a good way for most people to invest a significant fraction of their money; you probably want to be at least close to accredited investor levels (~$300k/yr income or $1 million liquid wealth) for it to make sense, and those at the accredited investor level already have other options. WeFunder is up front about the risks:

The other issue here is with asymmetric information and adverse selection. Its hard to find out much information about early-stage companies to know if they are a good investment; part of the point of the JOBS Act is that the companies don’t need to tell you much. The companies themselves have a better idea of how well they are doing, and the best ones might not bother with equity crowdfunding; they could probably raise more money with less hassle by going to venture funds or accredited angel investors.

I’ve long thought this adverse selection would be the killer issue, but my impression (not particularly well-informed and definitely not investment advice) is that there are now quality companies raising money this way, or at least companies that could easily raise money elsewhere. WeFunder has a whole page of Y-Combinator-backed companies raising money there. This week Substack, an established company that has already raised lots of venture funding, offered crowd equity and reached the $5 million limit of how much they could legally accept in a single day.

Overall I think this model is working well enough that I’m no longer in a hurry to become an accredited investor. Accredited investors have many more options for companies they can invest in and aren’t subject to the $2,200/yr limit on how much they can invest in early-stage companies. But even if I completed the backdoor process of getting accredited without being rich, I wouldn’t want to put more than $2,200/yr into early-stage companies until I was a millionaire, at which point I’d be accredited the usual way. And while most companies aren’t raising crowd equity, enough are that there seem to me to be no shortage of choices.

Best Books 2021

James BaileyLeave a comment

I read 23 books in 2021, but none that were written in 2021. Tim Ferriss stopped reading new books deliberately but for me it just happened, something about this year made me want to hang out in the ancient world instead.

I read about how five thousand years ago the Indo-Europeans figured out how to ride horses and use wheels, and so ended up spreading their language to half the world. I read about the Bronze Age Collapse three thousand years ago. Also set three thousand years ago are the semi-mythical events of the Aeneid and the Odyssey; I particularly enjoyed Emily Wilson’s new translation of the latter. From two thousand years ago, Caesar’s Commentaries reads like an action-packed fantasy novel but gives real insight into history and strategy. It was also a good year to go back to the Biblical events of two to three thousand years ago, though I didn’t make it cover to cover.

The one book about the modern world I gave 5 stars in 2021 was The Dictator’s Handbook: Why Bad Behavior Is Almost Always Good Politics. The short version of my review is that it’s secretly a development economics book:

Bueno de Mesquita, author of The Dictator’s Handbook, is a political scientist but his analysis is very much economic, in both the methods (rational choice & methodological individualism) and in the focus on material incentives as the main driver of behavior. The book is good as a manual for aspiring tyrants, but suprisingly great as an explanation for why many poor countries stay poor.

So overall compared to 2020 I don’t have many good books to share, apart from things like The Odyssey that you presumably already know about. The best new writing in 2021 probably isn’t happening in books at all, but in Substacks. Many bloggers switched to the Substack blogging/newsletter platform last year because it makes it easy to monetize their writing, while many professional journalists switched over as a way to keep being paid to write while enjoying near-complete editorial freedom. I recommend Byrne Hobart on finance and business strategy, and Razib Khan on history and genomics. Probably my favorite writing of 2021 was the return of Scott Alexander to blogging, now at Substack as Astral Codex Ten. He is also a great demonstration of just how much the monetization game has changed, as less than a year into the new Substack he is making enough money to start giving large amounts of it away.