Dialogue with Crypto OG: BTC's 10% surge was unexpected, but averaging in near the 200-day moving average while DCA-ing is never wrong

Compiled & Edited by: Deep Tide TechFlow

Guest: Rob, Founder and Host of Digital Asset News (X: @NewsAsset), entered the crypto market in 2017, has long publicly shared his personal DCA practices

Host: John Gillen, The Milk Road Show

Podcast Source: Milk Road

Original Title: Bitcoin Just Pumped… But Is the Bear Market Really Over?

Air Date: August 19, 2026

Disclosure: Rob is an independent content creator. During the show, he disclosed that he personally holds Bitcoin and a small amount of altcoins. He shares his personal investment practices and has no external fundraising or affiliated product interests.

Key Takeaways

This episode was recorded on August 19, the day before Bitcoin's massive surge. Guest Rob, host of the YouTube channel Digital Asset News, entered the market in 2017 and has been through a full market cycle. His investment approach is fully transparent: he references the risk meter on Ben Cowen's website, buying more as prices drop. His core thesis is straightforward: the area around the 200-week moving average has historically been a prime buying zone. In the short term, he maintains a "healthy pessimism" about the market, suggesting that based on the four-year cycle, the bottom could arrive around October, potentially falling to $55,000, $50,000, or even $45,000. But no sooner were those words out of his mouth than the very next day, on August 20, Bitcoin surged roughly 10% in a single day, briefly breaking through $70,000—hitting a high not seen since early June—and triggering the largest short squeeze since 2021, with over $1 billion in short positions liquidated in just one hour.

Rob's short-term price calls were quickly proven wrong by the market, but his real message wasn't about predictions—it was about the genuine discipline of a long-term individual investor: buy more as prices fall, take profits in tranches, and treat missed gains as tuition. The episode also covered the CLARITY Act and the White House meeting (his verdict: "theater"), the new SEC framework and the return of ICOs, how to diversify self-custody after the string of cold wallet incidents, why he only trusts four chains for altcoins, and AI agent payments as the next bull market narrative.

Key Highlights & Quotes

On the Bottom

• "I hope it hasn't bottomed yet, so I can buy more at even lower prices."
• "Buying Bitcoin at $3,000 in 2018 and at $15,000 to $17,000 in 2022—looking back, neither was a loss."

DCA Discipline

• "When the risk level hits 0.49, I double my buy; at 0.39, I quadruple; below 0.29, I go eight times."
• "Sometimes after a buy, my bank would call to confirm it was me. Now they've stopped calling."

Regulation & the White House

• "In a midterm election year, Democrats won't let Trump have a win, so the CLARITY Act probably won't pass."
• "When Congress fails us, the SEC and CFTC will step in to fill the gap."

The Self-Custody Dilemma

• "PlanB moved all his holdings into ETFs—he just doesn't want to deal with these headaches anymore."
• "Losing 25% hurts, but the worst is losing 100% with zero control over it."

Altcoins

• "I only recognize four chains: BNB, Ethereum, Solana, and Tron—they have the largest stablecoin flows."
• "When traditional markets sneeze, Bitcoin catches a cold, and altcoins go straight to the ICU."

Cycle & Next Narrative

• "Based on the four-year cycle, the bottom should come around October. Is it $55K, $50K, or $45K?"
• "When AI agents need to pay, they won't use PayPal's 2.9% plus 30 cents. It'll be fractions of a cent."

The 200-Week MA: Is This the Bottom or the Midpoint?

John: Bitcoin has reclaimed the 200-week moving average, which historically has marked bear market bottoms. But sometimes price lingers around that level for a while. Do you think we've bottomed, or is there more bear market ahead?

Rob: I hope it hasn't bottomed yet. Looking back, the area around the 200-week MA has always been a great buying zone. In 2015, we barely dipped below it. In 2018, after I got in, we broke below it following the 2017 peak, and everyone said it was over and it would never come back. Smart people just quietly kept dollar-cost averaging. Then in 2020 during COVID, we broke below it again—another great buying opportunity. By 2022, we even went below the 200-week, 250-week, and 300-week MAs. Right now, price is hovering around that 200-week MA, possibly just above it. For me, this is a pretty good time to buy. I don't want to repeat my 2022 mistake, when I did something stupid I call "micro-DCA"—the lower the price went, the less I bought, thinking I'd dump a lump sum when it got really low. If I'd stuck to my original plan and bought more as prices dropped, I'd be in a much better position now. Buying Bitcoin at $3,000 in 2018 and $15,000–17,000 in 2022—neither was a bad decision in hindsight. So back to your question: I hope it hasn't bottomed, to see if the four-year cycle plays out again this time, or if this is just a decent entry point.

DCA Every Monday: The Lower It Drops, The More You Buy

John: You're known for your weekly Monday Bitcoin DCA. In a bear market, prices can trade sideways for months. How did you design this strategy? And do you apply the same approach to selling in tranches during bull markets?

Rob: I look at risk levels, a metric I reference from Ben Cowen's website, Into The Crypto Verse. As price goes down, the risk level goes down. I start buying around 0.5 to 0.6. Below 0.49, I double my purchase from the previous Monday. At 0.39, I quadruple it. Below 0.29, I go eight times. These are all manual adjustments on my end. My buys run through Cash App's recurring purchase, auto-executed at 6:30 AM with almost negligible fees and decent spreads. Right now, the risk level is around 0.3, so I'm roughly in the quadruple-buy phase. Back when I was buying larger amounts, the bank would call to confirm it was me. Now they don't even bother. On the selling side, I did well in 2021—I set price targets and sold in tranches, based on fractal analysis. Take 2x profit off from the low, then another tranche at 4x. By 2025, I figured I should use indicators to look smarter, so I watched Pi Cycle Top, MVRV, Puell Multiple—and they all let me down. What ultimately nailed the top was a Reddit post from three years ago saying October 6, 2025, would be the absolute top. I thought it was impossible at the time, but that was exactly the day. So I took some profits on the way down. I didn't sell at the very top, and I don't believe anyone truly can. I know a lot of people say never sell your Bitcoin, but everyone has different goals. I sold a portion to pay off debt and move into safer assets like the S&P 500, bonds, and real estate, so I can sleep better at night. Most of my holdings remain in Bitcoin, not altcoins.

Historically Low Volatility: What Breaks the Stalemate?

John: Bitcoin's volatility over the last few months hit all-time lows, even below gold and equities. Do you see any near-term events that could break this pattern?

Rob: Hard to say. On the negative side, the AI bubble could burst, or there could be another massive cold wallet hack. On the positive side, CLARITY Act passing would be great, but I don't think it will. It's a midterm election year; Democrats won't hand Trump a victory lap. On the institutional side, there's been a steady stream of news—I just saw that Citi, the world's third-largest bank, is starting Bitcoin custody. We also have a president who promised to support crypto during his campaign, but many of his promises won't materialize, especially the CLARITY Act. In the short term, I don't see many positive catalysts. Congress keeps disappointing us, and the SEC and CFTC will fill the gap, but that only helps so much. The big move will have to wait until after this year, because everyone's mindset is dominated by the four-year cycle. Once we're past that, market psychology will shift, and prices can truly start rising.

CLARITY Act & the White House Meeting: Keep Expectations Low

John: The CLARITY Act has been delayed to September. Today, while recording, Trump is meeting with a bunch of crypto industry leaders at the White House. Do you think anything substantive will come out of it?

Rob: I hope so, but I just saw that World Liberty Financial received a conditional banking charter from the OCC. They want to use it to get into the stablecoin business—their stablecoin is already the fifth-largest. This strengthens the dollar's global position, with stablecoins backed by reserves. But the president wants to push it because it benefits his own company. I don't think that's going to go smoothly. The only thing I can control is my own investment scope, not a U.S. president running his own crypto company. If he can actually broker something meaningful with the industry and get Congress to move the needle, that would be great. But to me, this looks more like theater. The bill might pass in September, but I'm not holding my breath.

The SEC's New Framework & ICOs: Regulation Five or Six Years Too Late

John: The SEC passed a framework called "Regulation Crypto," covering ICOs, fundraising, and innovation exemptions for projects still building their networks. What are your thoughts? The 2017 ICO boom also brought a wave of rug pulls. How do you reconcile the desire for industry vitality with the need for investor protection?

Rob: The government is about five or six years too late here. When I entered in 2017, ICOs were everywhere. If this framework had been in place earlier, a lot of good projects could have gotten funded. I looked at the details—up to $5 million with essentially no hurdles, and another tier at $75 million over four years. If this actually goes through, money will flow into the crypto industry. But I have one concern: do we really need more new projects and more altcoins? There are already millions out there. I'll stick with battle-tested projects and keep building on top of them. It's good that the SEC and CFTC are putting up guardrails—it won't be the Wild West anymore—but I don't see this as a decisive catalyst. I could be wrong, though. And let's consider how outsiders see us: they just say, "Oh, that's the thing where people play meme coins and just got hacked." Look at Coinbase's Super Bowl ad this year—it started with a choir, and when it cut to Coinbase, the whole stadium booed because that's where they lost money. Trump coin and Melania coin screwed over a ton of people. Guardrails are good, but we need projects that actually change the game, not just more filler.

After the Cold Wallet Breaches: Diversify Your Self-Custody

John: Last week, Coldcard, Trezor, and SafePal all had incidents, making people uneasy about self-custody. What's your take?

Rob: Some people will say it's a coincidence, especially since custody services like Citi are launching. But remember, Coldcard has been around for years. Conspiracy theories don't matter. What matters is that a lot of people actually lost money. PlanB said two years ago, "I've moved everything into ETFs." Nobody understands cold storage better than he does, but he said he doesn't want to deal with these headaches anymore. On the other side, Simon Dixon says this is about pushing people from self-custody toward custody. In my case, every week or two, I get an email from someone saying they lost their entire life savings. It's not just user error leading to hacks—companies like Ledger and SafePal themselves got hacked, leaking addresses, emails, and phone numbers. The scariest thing is "I don't know what I don't know." What if a major cold wallet company suddenly announces, "There was a vulnerability we never found," and hundreds of thousands of people's Bitcoin is gone? So now I diversify my security too: part on Ledger, part on Tangem, part with iTrust custody, part on Coinbase Prime—the same one Strategy and BlackRock use—and another portion in ETFs. I refuse to be the guy who goes back to his wife and says, "Lazarus Group stole our entire life savings." Steve Wozniak put $3.2 million into Bitcoin and still got scammed. Losing 25% hurts, but the worst is losing 100% with zero control. I'd rather protect more people than have them all tough it out on their own.

Altcoins: I Only Trust These Four Chains

John: Besides Bitcoin, are altcoins part of your DCA list?

Rob: Stablecoins will do very well, especially in strengthening the dollar. Look at Visa's on-chain data—the chains with the highest stablecoin flows are always those four: Binance, Ethereum, Solana, and Tron. I call it BEST. Polygon is worth discussing, and XRP folks will talk to you about cross-border payments—I get it—but my capital is limited. Payments are only one piece; the biggest driver is speculation. Beyond that, there's