The Questions Everyone Was Asking — Finally Answered

I buy my Bitcoin on River. Alex Leishman is the CEO, and he’s one of the most grounded, data-driven people in this space. I sat down with him in New York, and what he shared with me was really useful because it was honest — even if it wasn’t all optimistic.

Most River clients have not sold through this bear market. On net, they’re still buying. But recent volumes are among the lowest they’ve been in about a year and a half, around where they were at the peak of the previous bull market. For a company that has grown a lot since then, that tells you something about how heavy this grind has been.

The more telling number is what’s happening across the whole market. River’s estimates show that in Q2, individuals net sold roughly 78,000 Bitcoin. Businesses and institutions net bought around 115,000. Institutions, including ETF buyers, are accumulating. Retail, on balance, is letting go of some of their coins.

Alex actually isn’t worried about that. He said it’s how every mature asset class evolves. As Bitcoin grows, a bigger share of it will end up on institutional balance sheets, the same way most equities, bonds and real estate are. What matters is whether those institutions actually understand Bitcoin. The ones he talks to do. They know turning it into Wall Street coin would undermine the very thing they’re buying.

There are a lot of target buy orders sitting in River’s system at $50,000 and below. But there are actually more target orders above current prices than below, which means more people are positioned to buy on the way up than to catch a falling knife.

And new clients are still coming in. Slower than a year ago, but meaningfully higher than any previous bear market at this stage.

Only about 15% of River clients withdraw their Bitcoin to self-custody. Alex had a great take on this. Telling everyone they must self-custody, he said, is like a chef telling everyone they must cook all their own meals. Some people will and should. For a lot of others, what matters most is that they’re somewhere they genuinely trust, with clear, easy paths to withdraw if they ever want to.

His security advice for right now is practical. Keep your information footprint small. Don’t hand your details to exchanges you don’t actually use. Treat every unsolicited phone call or email as potentially malicious. If someone says they’re contacting you from River or any other institution, don’t respond to them. Log into the app yourself or call the number on the website.

“The people who are happiest that they hold Bitcoin did not get in when everyone else was really excited about it.”

Worth remembering.

Last week I had the honor of moderating Strategy’s second live retail investor Q&A, putting unfiltered questions directly to Michael Saylor and Phong Le that were submitted by shareholders — people with real money invested in the company and real questions they deserve honest answers to.

I want to say upfront that some of these questions carried strong emotions. One investor wrote in to say he had invested $73,000 for each of his three children into MSTR, and today those investments are worth about $20,000 each. He expressed concern that MSTR was the company’s lowest priority and asked whether Strategy was considering adding a dividend for common stock holders.

Phong’s response was that since Strategy began its Bitcoin strategy in August 2020, Bitcoin is up roughly 32% and MSTR is up about 41%. The equity has actually outperformed Bitcoin over that time. But MSTR is what he called amplified Bitcoin, which means when Bitcoin falls 50%, MSTR tends to fall further. That amplification is the product. And what fixes MSTR, he said, is fixing the credit side of the business — getting STRC back to health — which is where all of the company’s energy is focused right now.

Michael added something worth sitting with. If you’re holding the equity and your time horizon is less than four years, you’re probably in the wrong instrument. If you want a dividend, he said, you should be looking at one of the preferred stocks. MSTR was always designed as amplified, long-duration Bitcoin exposure. That’s the product.

Both Michael and Phong were candid about what they’ve taken away from the recent STRC drawdown and recovery. The biggest lesson was the importance of holding U.S. dollar liquidity as a backstop to dividends, which is why Strategy now holds $4.8 billion in cash. Going forward, a portion of every STRC raise will go toward growing that reserve, giving institutional investors the cushion they need before allocating serious capital.

The second lesson was about flexibility. Strategy has always been willing to buy Bitcoin and issue STRC. What the market needed to see was that they could also sell Bitcoin and buy back STRC when the situation calls for it. As Phong put it, you can’t just have a right hand — you have to have a left hand too. Michael added that if Strategy isn’t willing to sell Bitcoin, then Bitcoin isn’t being fairly valued on the balance sheet, and neither is the credit backed by it. Being able to trade both sides of every instrument is what makes the whole system work.

A shareholder asked about MSCI’s recent proposal to remove Bitcoin treasury companies from their indices. Phong’s answer was matter-of-fact.

MSCI indices represent 3 to 4% of Strategy’s current shares, so removal would create some selling pressure but ultimately be immaterial. More interesting was his view of the proposal itself — that MSCI is out of step with the SEC, FASB, and other indices, all of which have already defined Bitcoin as a legitimate operating asset for Strategy.

He’s hopeful MSCI will reconsider, but even if not, it isn’t a real concern for the company.

One shareholder asked whether modeling Strategy after J.P. Morgan contradicts Bitcoin’s founding philosophy.

Phong’s answer was that Strategy doesn’t want to be J.P. Morgan. The company wants to be the “J.P. Morgan of Digital Assets.” The trust, the scale, the central role in the financial system — those are worth building toward, but in the Bitcoin-native world rather than the traditional one.

The path to get there is holding the most Bitcoin, building products like MSTR and STRC on top of it, and creating a foundation strong enough for others to build on.

Michael said something worth quoting directly: “Don’t invest in Bitcoin unless you’re going to hold it for more than four years. Ideally, hold it for ten.” The more Bitcoin Strategy buys, in their view, the higher the price goes over time. The duration of their credit book is roughly 33 years — that’s the timeframe they’re operating in.

I am so honored to be the very first guest on Dishing Up Bitcoin, the first Bitcoin cooking show ever made, hosted by Norma Chu — the founder and CEO of DDC Enterprise, the NYSE-listed global Asian food platform that has become one of the most active Bitcoin treasury companies in the consumer space.

Norma and I made dumplings together. And in between wrapping them, we talked about the things you don’t usually get to hear on a typical interview — where we come from, our families, the moments that shaped who we are. I opened up about my family’s bankruptcy after the Great Financial Crisis and how that experience shaped the way I think about money, and eventually how it led me into the Bitcoin space.

Norma shared her own story building DDC and what it’s been like leading a public company that’s also stacking Bitcoin.

It was one of the most fun and genuinely open conversations I've done recently, and honestly, it reminded me how much of Bitcoin is really about people, families, and the values we’re trying to protect for the next generation.

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