Rob, the founder and host of Digital Asset News, said Bitcoin trading around the 200-week moving average still looks like a sensible place to build a position. Short term, though, he said he is "healthily bearish." Using a four-year cycle framework, he said the market could bottom around October, with possible levels at $55,000, $50,000, or even $45,000.
Those remarks came during a Milk Road episode released on Aug. 19, 2026. The summary says the recording happened one day before Bitcoin ripped higher on Aug. 20. After the taping, BTC jumped about 10% in a single day, briefly pushed above $70,000, reached its highest level since early June, and set off what the summary called the biggest short liquidation wave since 2021. More than $1 billion in short positions got liquidated in just one hour.
The talk featured Rob and The Milk Road Show host John Gillen. The summary says Rob entered crypto in 2017 and has spent years publicly documenting his personal dollar-cost averaging approach. The episode also said he is an independent content creator who owns Bitcoin and a small amount of altcoins, and that he was walking through his own investing process, not pitching a fundraising campaign or related product.
Rob still sees the 200-week moving average as a buy zone
John Gillen started by pointing out that Bitcoin had climbed back above the 200-week moving average. That level has often matched bear-market bottoms in earlier cycles, even if price can drift around it for a long time. So he asked the obvious question: was the bottom already in, or was there still more downside left?
Rob answered directly: "I hope it hasn’t bottomed yet, so I can buy more at lower levels."
He said the zone around the 200-week moving average has shown up again and again as a strong area to buy. In 2015, Bitcoin only slipped below it briefly. In 2018, after the 2017 peak, the market fell under it again and sentiment cratered, but people who kept buying were rewarded later. During the 2020 pandemic shock, Bitcoin dropped below the line once more, which he also sees as a good buying point. And in 2022, he said, Bitcoin even fell below the 200-week, 250-week, and 300-week moving averages.
Right now, he said, price is still trading around the 200-week line and may now be holding above it. For him, that still counts as "a pretty good time to buy."
Rob also said he does not want to repeat what he considers a 2022 mistake. He called it a kind of "mini DCA." Basically, he bought less as price fell because he wanted to wait for an even lower level and then put in more capital all at once. Looking back, he said he would be in a better spot today if he had just kept buying more aggressively as price dropped.
He used earlier cycle examples to hammer that home: buying Bitcoin at $3,000 in 2018, or at $15,000 to $17,000 in 2022, does not look bad in hindsight.
His DCA system scales up as risk falls
When Gillen asked how he handles weekly Bitcoin purchases during long stretches of sideways bear-market trading, Rob said he uses a risk metric from Ben Cowen’s Into The Crypto Verse. As price falls, the risk reading falls too, and he increases his position size based on that shift.
- He starts buying around 0.5 to 0.6 on the risk scale.
- Below 0.49, he doubles his purchase size versus the previous Monday.
- At 0.39, he takes that to 4x.
- Below 0.29, he moves to 8x.
He said those multipliers are his own manual tweaks. The buys happen through recurring purchases on Cash App, which run automatically at 6:30 a.m. He said the fees are almost negligible and the spread is fine. At the time of the discussion, he said the risk reading was around 0.3, putting him roughly in the 4x buying phase.
And one more thing. Banks used to call and check whether the larger purchases were really his, but "now they don’t call anymore."
On selling, he prefers staged profit-taking over calling the exact top
Rob said he handled exits better in 2021 because he set price targets and took profit in stages, using fractal-style thinking to guide the process. In his version of it, he would take some profit after a 2x move off the lows and then another portion after a 4x move.
In 2025, he tried to get fancier and leaned on indicators like Pi Cycle Top, MVRV, and Puell Multiple. He said they let him down.
What actually called the top, he said, was a Reddit post from three years earlier claiming that Oct. 6, 2025 would be the exact top. At the time, he said, that sounded impossible. But the date ended up matching the peak.
Even then, he said, he did not sell the exact top, and he does not believe most people can. He took some profit on the way down instead. Rob also pushed back on the idea that Bitcoin should never be sold no matter what, saying every investor has different goals. He said he sold part of his holdings to pay off debt and move capital into what he described as safer assets, including the S&P 500, bonds, and real estate. Most of his exposure, he said, still sits in Bitcoin rather than altcoins.
He sees few near-term positive catalysts
John Gillen pointed out that Bitcoin volatility in recent months had dropped to record lows, even below gold and equities, and asked what might break the stalemate. Rob said it was hard to say.
On the downside, he mentioned two possible triggers: an AI bubble bursting or another major hack involving hardware wallets. On the positive side, he said passage of the CLARITY Act would help, but he does not think that is likely.
Rob said: "In a midterm election year, Democrats are not going to let Trump win this one and hand him a victory lap."
He also said institutional news keeps showing up. He added that he had just seen Citi, which the summary described as the world’s third-largest bank, getting ready to offer Bitcoin custody. At the same time, he said, the U.S. has a president who campaigned as pro-crypto, but many promises still may not get delivered, especially on the CLARITY Act.
His short-term view was blunt. He does not see many obvious positive catalysts. Congress, he said, has let the market down again and again. The Securities and Exchange Commission and the Commodity Futures Trading Commission may cover part of that gap, but only to a point. The bigger move, he said, may have to wait until this year is over because trader psychology is still ruled by the four-year cycle story.
CLARITY Act and the White House meeting: more posture than progress, in his view
Gillen also asked about the CLARITY Act being delayed until September and about Trump meeting crypto industry leaders at the White House on the day of the recording. Would any of it produce something real?
Rob said he hoped so, but what he was watching looked more like political theater. He pointed to World Liberty Financial getting a conditional national bank charter from the Office of the Comptroller of the Currency, saying the company wanted to use that opening to move into the stablecoin business and that its stablecoin had already become the fifth largest. He said moves like that could help strengthen the U.S. dollar’s global position because stablecoins need reserves behind them.
Still, he said, efforts pushed by a president that also benefit that president’s own company are not likely to go smoothly. In his view, that part is outside his control. If the White House can produce meaningful talks with the industry and push Congress forward, he said, great. But his own read was that the meeting looked mostly like "posturing."
As for the September legislative timeline, he said he was not expecting much.
SEC’s new framework and ICOs: useful, but years late
The conversation then moved to the SEC’s proposed "Regulation Crypto" framework, which covers ICOs, fundraising, and innovation exemptions for networks still being built. Gillen asked how investor protection could be balanced with the need to keep room open for legitimate project funding, especially after so many rug pulls followed the 2017 ICO boom.
Rob said the government was probably five or six years late. Back in 2017, when he entered crypto, ICOs were everywhere. If a clearer framework had existed then, he said, plenty of stronger projects might have raised money under more orderly conditions.
He said he had gone through some of the details. Offerings up to $5 million face very few barriers, and another tier allows $75 million over four years.
If the rules are applied that way, he said, money will come back into crypto. But he also wondered whether the industry really needs more new projects and more altcoins at this stage, saying there are already millions of them. His preference is to stick with battle-tested projects and keep building on top of those networks.
Rob said it would be a good thing if the SEC and CFTC manage to put guardrails in place so the market is not as lawless as it used to be. But he did not go as far as calling that a decisive catalyst. He also talked about how the public still views crypto. In his telling, outsiders often boil it down to meme coins and assets that keep getting hacked.
He used Coinbase’s Super Bowl advertisement as an example. According to Rob, the room felt upbeat at first, but when the Coinbase segment appeared, the reaction turned into boos because that was where many people had lost money. He also mentioned Trump coin and Melania coin as projects that hurt even more participants.
Guardrails matter, he said. But what the industry really needs are projects that can change the game, not just add to the pile.
After recent wallet incidents, he is diversifying security too
On self-custody, Gillen noted that Coldcard, Trezor, and SafePal had all run into issues the previous week, leaving users rattled about managing their own coins. Rob said some people would call that timing a coincidence, especially with firms like Citi preparing custody services, but he did not think conspiracy theories were the main issue. The real point, he said, is that people did lose money.
He brought up PlanB, saying that two years earlier PlanB had moved all of his holdings into ETFs because he no longer wanted the headaches that came with cold storage. He also mentioned Simon Dixon, who argued that these events were pushing users away from self-custody and toward custodians.
Rob said he gets emails every week or two from people saying they lost their life savings. In his view, these incidents are not just user error. Companies like Ledger and SafePal have also had breaches that exposed addresses, email accounts, and phone numbers.
What worries him most is the unknown. Simple as that. He put it this way: "I don’t know what I don’t know." If a major mainstream hardware wallet one day revealed a long-undetected vulnerability and hundreds of thousands of people lost Bitcoin because of it, the damage would be severe.
That is why he now diversifies his security setup too. He said part of his assets are on Ledger, part on Tangem, part in iTrust custody, part at Coinbase Prime, which he identified as the provider used by Strategy and BlackRock, and part in ETFs.
He said he refuses to be the guy who has to go home and tell his wife, "The Lazarus Group stole our entire savings." He also mentioned Steve Wozniak, saying Wozniak put $3.2 million into Bitcoin and still lost it in a scam.
Rob boiled the trade-off down this way: losing 25% hurts, but losing 100% with no control is far worse. He said he would rather help more people protect themselves than insist everyone shoulder the full self-custody burden alone.
He only really focuses on four chains for altcoins
Asked whether altcoins are part of his DCA list too, Rob said stablecoins are set up for strong growth and will keep reinforcing the dollar. Citing Visa’s on-chain data, he said the biggest stablecoin traffic consistently runs through four chains: Binance, Ethereum, Solana, and Tron. He calls that group "BEST."
He said Polygon deserves discussion, and he understands the cross-border payments case often made by XRP supporters, but his capital is limited and he has to make choices.
Payments are only one piece of it, he said. Speculation is still the bigger force. Beyond that, he sees real-world asset tokenization as another major area, including bonds, equities, and real estate moving on-chain.
On network positioning, he described Ethereum as the institutional and Wall Street choice, even if DeFi hacks have damaged perception. Tron, he said, is Tether’s huge base, with more than 60% of Tether’s volume on Tron. He also said Canton has a large share in tokenization and Hyperliquid has strong perpetuals activity, but neither is enough to make him rebalance right now.
His shorthand for how risk spreads across digital assets was simple: "If traditional markets sneeze, Bitcoin gets the flu, and altcoins go straight to the ICU."
For the next cycle, AI agent payments stand out to him
When Gillen asked which story he liked most out of tokenization, stablecoins, and AI agent finance, Rob picked AI agent payments.
His reasoning was practical. Time is the one thing you cannot buy. If he could use a robot that would not turn around and create new problems, and that robot could handle a full Puerto Rico trip booking for him, pay with extremely low fees, and even earn rewards, that would be compelling.
He pointed to Cloudflare, which he said announced the previous week that it would add support allowing AI agents to pay with cryptocurrency. Fees, he said, would not look like PayPal’s 2.9% plus 30 cents. They could drop to fractions of a cent.
He also made it clear that the model comes with risk. What happens if the AI agent goes off the rails? To make the point, he mentioned a developer who told an AI system to clean up an email inbox, only to watch it delete every file on the computer. Rob said the age of autonomous agents will bring more failures that people have not even imagined yet.
Gillen suggested smart contracts and decentralized identity could help offer a solution. Rob agreed the area looks promising, but said it is still wide open and nobody knows what the final form will be.
His October bottom thesis is unchanged, but he still expects weakness into November
Near the end of the discussion, Gillen noted that Rob was set to attend Ben Cowen’s Investing Through the Cycles conference in Miami in November and asked whether the market would be out of the bear phase by then.
Rob recalled Cowen saying that if the conference could succeed during the worst stretch of the bear market, then the following year would be better, the year after that would be the halving year, and the year after that would be the major bull market. In that sense, Rob said, the conference itself acts as a kind of test.
As for Bitcoin, he stuck to his cycle view. The bottom, he said, should arrive around October under the four-year framework. Whether that level is $55,000, $50,000, or $45,000 is still uncertain.
He added that if Bitcoin really dropped to $45,000 in October, he would expect it to be back around $50,000 to $55,000 by November. That, he said, would make him happy because it would mean he had been buying consistently at lower prices.
Still, his broader November outlook stayed cautious. He said Bitcoin would probably still be moving around low levels by then, with more pain still possible.
As the episode wrapped, Gillen remarked that while they were speaking, ETH had already broken above $2,000 and Bitcoin had climbed back above $68,000, joking that maybe they had talked the bottom into existence. Rob fired back with a joke of his own: "Congratulations, we saved the entire market."