Serious News

Chris Duff

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I Lost Millions: What Drawdowns Teach You About Real Risk Tolerance | Ep. 278

In this episode, In 2021, I was making $200k in passive crypto cash flow; by 2022, it was gone in the Vault collapse. This is a post-mortem on greed, the failure of due diligence on counterparties, and how it reshaped our land fund’s risk profile.

Key Takeaways:

  • The Recovery Trap: $90M was recovered by Vault, but distribution is stalled by ego battles and legal red tape, never bank on a “quick” bankruptcy payout.
  • Liquidity First: We now operate with 41% margins and hold excess liquidity because true risk tolerance is only found after you lose money.
  • Boring is Better: We are rebuilding wealth through boring, high-margin land deals rather than chasing the next hype cycle.

Watch the full episode to hear why mental toughness is your greatest asset in a society of comfort seekers.

(Podcast transcript below)

Welcome to Get Serious over at Serious Land Capital. We have funded over $6 million worth of land deals with industry leading 41 % operating margins. So today I wanted to do a read through of my latest Serious News newsletter. I got some excellent feedback on that recently, so I’ll dive right in if you haven’t already read it

Or if you want to hear the audio version instead, this is for you. So it was titled, I Lost Millions and What I Learned. What I’m Thinking About Reflections on Comically Bad Business Decision Making. Everything’s disjointed during the holidays, so I’m going to share a couple of stories you’re bound to get a kick out of and learn from.

For background, I’ve experimented with various private investments over the past roughly 15 years. One of the most significant has been within crypto, having started in early 2014 when Bitcoin was under $1,000 per Bitcoin FYI. And during a historic bull run across most assets,

I was sighing in fond remembrance as I was writing this. Throughout much of 2021, there was a roughly six week period in late 2021, just prior to the Fed raising rates, when my liquid net worth was surging by millions of dollars and my interest earning crypto accounts were generating about 200K in annual cashflow with real time distributions.

all on top of our healthy land business income. Everyone knows the Warren Buffett quote to quote, be fearful when others are greedy and greedy when others are fearful. Though rare is the investor who obeys that, particularly in periods of extreme greed or fear. Needless to say, I didn’t take anything off the top.

And what followed was a slow moving train wreck of net worth destruction in the neighborhood of 80 % plus. For what it’s worth, all of my other friends and investor colleagues were caught in a similar situation or worse. The Fed gave plenty of advance notice on where rates were going and we all hand waved it away or didn’t have the experience to comprehend the impact. To make matters worse,

By mid-2022, most of my crypto holdings got tied up in one of those crypto bank collapses, think FTX, Celsius, BlockFi, et cetera. There were several of them. Though mine was within a platform called Vault, where I had direct access to the CEO. Even with ample opportunity to remove my holdings to self-custody as the crypto market was melting down, I placed my trust in the wrong people and institutions.

and Vald entered a restructuring that is still ongoing three and a half years later. And you can Google all of these details if you’re interested. All this while real estate and land flipped to a nasty market by the second half of 2022. Toughest year personally and professionally to date.

With crypto rebounds over the past few years, most of those restructurings have resolved and made creditors whole. And while Vault has returned significant assets back to us so far, the process has been far from smooth. To catch you up on the current status, Vault has recovered $90 million worth of liquid assets from the largest counterparty that owes us funds almost four months ago.

And per the legal documentation, this was due for distribution to creditors immediately thereafter. And as one of the largest creditors involved, that portion of the $90 million pile due to me personally would be a windfall, I can assure you. What ensued was a major boardroom dispute over which platform to distro the assets and the Vald CEO and creditor representative

which as the name implies was a fellow creditor with more than $3 million locked up involved himself, went rogue against Kroll, which is a large global risk advisory firm. Many of you probably have heard their name and Kroll had been managing the collection process. Tons of detail I’m skipping over, but suffice to say the dispute continued to escalate.

The CEO was fired and the creditor representative seems inclined to self-destruct with significant collateral damage for the sake of his ego. And the longer I’ve been in business, the more I realize how common this behavior is. And I’ve been guilty of that myself, in truth. Right now, awaiting resolution in the Singapore court, best case is a distribution by mid February.

be much longer. Meanwhile, there’s about a 10 % net loss on that $90 million pile given the recent crypto downturn compared to when the funds were recovered. I was relaying over that vault update to a friend recently, and it serves as a reminder on how dysfunctional and messy any human venture can be, regardless of the money involved.

If we’re able to routinely put our egos aside and stay focused on building from a we-first mentality alongside servicing our customers and investors to the best of our abilities, we’ll position ourselves better than 90 % of other businesses. My estimate, but sure feels about right for long-term profitability and impact.

And personally, as quote, financially rich, as I felt in that short span in late 2021, key friendships were in a rocky place and I was lonely. If the universe had presented me a trade where I could go back in time and sell all my investments at their peak at the cost of those friendships, I wouldn’t take the deal or spend more than a second thinking about it.

Rebuilding financial wealth is inevitable, but never at the cost of sacrificing the relationships most important to me. Also, as Ray Dalio notes, pain plus reflection equals profits. 2022 brought a ton of pain and reflection, and I know I’m not the only one. If I had acquired a bunch of wealth quickly,

I may not have been as incentivized to build a much more sustainable long-term profit engine like Serious Land Capital. Plus, no one ever understands their true financial risk tolerance until they lose money. While I’m certainly not seeking it out, I now know that I can stare down millions of dollars of losses and not lose my nerve to steady the ship and start the rebuilding process. Never.

Let your pain go to waste. Your mental toughness is your greatest advantage in a society of comfort seekers. Let’s not ask, what does 2026 have in store for me? Rather, what do you have in store for 2026? Looking for a funding partner who understands the pain of loss and will do whatever it takes to avoid that?

We’re funding deals from 50K to over a million dollars. Land investing experience is preferred, but not required. Feel free to submit any deals on our SeriousLand.Capital website or email funding@seriousland.capital. Hope you all enjoyed this one. Looking forward to next time. Subscribe and share everybody. Take care now. Bye.

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