Rob, founder and host of Digital Asset News, said in a Milk Road interview recorded on Aug. 19 that he still treats the area around Bitcoin’s 200-week moving average as a buy zone, even though his short-term price call was quickly overtaken by the market.
In the interview, Rob said a four-year cycle model suggested Bitcoin could find a bottom around October, with possible downside targets at $55,000, $50,000, or even $45,000. A day later, on Aug. 20, Bitcoin rose about 10%, briefly climbed above $70,000, reached its highest level since early June, and set off the largest short liquidation wave since 2021. More than $1 billion in short positions were liquidated in one hour.
Rob’s near-term outlook was wrong on timing, but the main point he kept returning to was not prediction. He framed the discussion around a long-term retail discipline: buy more when price falls harder, take profits in pieces on the way up, and accept missed tops as part of the process.
Why he still watches the 200-week moving average
Host John Gillen opened by noting that Bitcoin had moved back above the 200-week moving average, a level that has often lined up with bear-market bottoms, even if price can spend a long time churning around it.
Rob said he actually hoped the market had not bottomed yet because lower prices would let him buy more. Looking back, he said the 200-week moving average has repeatedly marked attractive accumulation territory. He pointed to 2015, when Bitcoin only briefly broke below it, to the 2018 drawdown after the 2017 peak, and to the 2020 pandemic sell-off. In 2022, he said, Bitcoin even fell below the 200-week, 250-week, and 300-week moving averages.
For that reason, he said the current area still looks like a good place to buy if price is moving around that long-term average or only recently reclaimed it.
Rob also said he did not want to repeat what he called his 2022 mistake. At that time, he used a “micro DCA” approach, buying less as price fell because he was waiting for an even lower level to deploy more capital at once. He said sticking to a plan of increasing size into weakness would have left him in a much better position. In his view, Bitcoin bought near $3,000 in 2018 and Bitcoin bought in the $15,000 to $17,000 range in 2022 both still look fine in hindsight.
His DCA system: lower risk reading, bigger buys
Rob has publicly shared his accumulation approach for years. In the interview, he said he uses the risk indicator from Ben Cowen’s Into The Crypto Verse website and scales his purchases as the reading falls.
He described the framework this way:
- He starts buying when the risk level is around 0.5 to 0.6.
- If it falls below 0.49, he doubles his buy size versus the prior Monday.
- At 0.39, he goes to four times the size.
- Below 0.29, he increases to eight times.
He said those multipliers are his own manual adjustments. Execution runs through recurring purchases on Cash App at 6:30 a.m. every Monday, with fees that he described as almost negligible and with solid spreads. At the time of the recording, he said the risk reading was roughly 0.3, which put him around the four-times-buy phase.
He added a personal detail: when his purchase size used to jump, his bank would sometimes call to confirm the transactions. Now it does not.
Selling, in his view, means staged profit-taking rather than trying to nail the top
On exits, Rob said he handled 2021 better than later periods because he used fixed price targets and sold in pieces. In his version of the strategy, he took some profit after a 2x move from the lows and another portion after a 4x move.
He said that by 2025 he thought using indicators would be a smarter approach, so he watched Pi Cycle Top, MVRV, and Puell Multiple. Those signals disappointed him. The call that he said ended up matching the top came from a three-year-old Reddit post claiming Oct. 6, 2025 would be the absolute top, and he said that date did in fact mark it.
Even so, Rob was explicit that he did not sell the exact high. He took profits on the way down and said he does not believe people reliably sell the top anyway. He also pushed back on blanket claims that Bitcoin should never be sold. His own goal, he said, was to pay off debt and rotate some gains into assets he sees as steadier, including the S&P 500, bonds, and real estate. Most of his exposure, he added, remains in Bitcoin rather than altcoins.
Few near-term catalysts, and little faith in political theater
John noted that Bitcoin’s volatility had fallen to historic lows over recent months, even below gold and equities, and asked what could break the stalemate.
Rob said the answer was not obvious. On the downside, he pointed to the possibility of an AI bubble breaking or another major cold-wallet hack. On the upside, he said passage of the CLARITY Act would help, but he does not expect it to pass. His reasoning was political: in a midterm election year, he said Democrats would not want to hand Donald Trump a victory lap.
He also mentioned seeing news that Citigroup, which he described as the world’s third-largest bank, was preparing to offer Bitcoin custody. Even with institutional developments in the background, he said he does not see many near-term bullish catalysts. Congress has repeatedly disappointed the market, and while the U.S. Securities and Exchange Commission and the Commodity Futures Trading Commission may fill some of the gap, he said their contribution would be limited.
His broader point was that a larger move may have to wait until the year is over, because market psychology is still heavily shaped by the four-year cycle.
CLARITY Act and the White House meeting: “posturing” in his view
The conversation also turned to the CLARITY Act, which had been delayed to September, and to a White House meeting on the day of recording between Trump and crypto industry executives.
Rob said he would like to see tangible progress, but he was not optimistic. He brought up World Liberty Financial, which he said had just received a conditional national bank charter from the Office of the Comptroller of the Currency and was looking to move into stablecoins. He added that its stablecoin had already become the fifth largest. He said this would support the global role of the U.S. dollar because stablecoins require reserve backing.
At the same time, he argued that any push from a president becomes harder when it is tied to the president’s own company interests. He said that is not something he can control as an investor, and he can only control the scope of his own investment decisions.
If the White House meeting helps move Congress even slightly, he said, that would be positive. But his own conclusion was blunt: the event looked more like posturing than a breakthrough. As for the September legislative window, he said he was not expecting much.
SEC’s new crypto framework and the return of ICO-style fundraising
On the SEC’s new “Regulation Crypto” framework, Rob said regulation was arriving five or six years too late.
He said the 2017 market was full of ICOs when he first entered crypto, and that many legitimate projects might have been funded more cleanly if a framework like this had existed earlier. Based on what he had reviewed, he said offerings up to $5 million would face minimal barriers, while another tier would allow as much as $75 million over four years. If implemented as described, he said, the framework would bring capital into crypto.
Still, his concern was not whether money would come in. It was whether the industry actually needs more new projects and more altcoins. He said there are already millions of them. His own preference is to stay with projects that have already been tested and to build on top of those ecosystems.
He said it would be better if the SEC and CFTC put proper guardrails in place, rather than leaving the market as lawless as it was before. But he stopped short of calling that a decisive catalyst. He also argued that outsiders still tend to reduce the industry to meme coins and hacks. As an example, he referred to a Coinbase Super Bowl ad and said the crowd reaction turned into boos when Coinbase appeared because that was where many people had lost money. He also cited Trump coin and Melania coin as products that burned another wave of participants. Guardrails help, he said, but what crypto needs is not more filler tokens. It needs projects that materially change the market.
After problems involving major wallets, he now diversifies security too
When John asked about self-custody after issues involving Coldcard, Trezor, and SafePal, Rob did not give a simple all-or-nothing answer.
He said some people will dismiss the timing as coincidence and others will connect it to the rollout of new institutional custody products from firms such as Citigroup. Either way, he said, people did lose money. He brought up PlanB, saying that two years ago PlanB said he had moved everything into ETFs. Rob’s point was that even someone deeply familiar with cold storage may still decide the operational burden is not worth it.
He contrasted that with Simon Dixon, who has argued that such events push users away from self-custody and toward custodians. Rob said he receives emails every week or two from people saying they lost their life savings. In his telling, the problem is not limited to user mistakes. Firms such as Ledger and SafePal have also suffered breaches that exposed addresses, email accounts, and phone numbers.
What worries him most is the unknown risk. If a mainstream hardware wallet one day discloses a long-undetected vulnerability and hundreds of thousands of users lose Bitcoin, he said, the damage would be catastrophic.
His answer has been to spread risk across different setups: some assets on Ledger, some on Tangem, some in custody with iTrust, some on Coinbase Prime, and some in ETFs. He noted that Coinbase Prime is also used by Strategy and BlackRock.
Rob said he does not want to be the person who goes home and tells his wife that the Lazarus Group stole all of their savings. He also cited Steve Wozniak, saying Wozniak put $3.2 million into Bitcoin and still got scammed out of it. Losing 25% is painful, he said, but losing 100% while having no control is worse.
On altcoins, he focuses on four chains
Outside Bitcoin, Rob keeps his list short. He said stablecoins will keep growing and will strengthen the dollar’s role. Citing Visa’s on-chain data, he said stablecoin activity is consistently concentrated on four chains: Binance, Ethereum, Solana, and Tron. He refers to that group as “BEST.”
He said Polygon is worth discussing and that he understands the cross-border payments pitch from the XRP community, but his capital is limited. In his view, payments are only one part of the story, while speculation remains the larger force.
On the next layer of crypto use cases, he highlighted tokenization of real-world assets, from bonds and stocks to real estate. He described Ethereum as the chain institutions and Wall Street appear to prefer, even if DeFi hacks continue to hurt its public image. Tron, in his view, is the giant in Tether’s network footprint, with more than 60% of Tether activity on Tron.
He also mentioned Canton as a significant player in tokenization and Hyperliquid as active in perpetual futures, but said neither is enough to make him rebalance now.
His summary of cross-market stress was simple: when traditional markets catch a cold, Bitcoin gets the flu, and altcoins end up in the ICU.
Why AI agent payments stand out to him
Asked which future narrative he likes most among tokenization, stablecoins, and AI agent finance, Rob picked AI agent payments.
He said the appeal comes down to time. If a reliable software agent could plan a trip to Puerto Rico, pay for services at very low cost, and even earn rewards, that would be genuinely useful. He pointed to Cloudflare’s announcement the prior week that it would support crypto payments for AI agents. In his telling, such payments would not carry fees like PayPal’s 2.9% plus 30 cents. They could be done for fractions of a cent.
But he also said that promise comes with risk. He cited a story in which an AI tasked with cleaning up an email inbox ended up deleting every file on a computer. The broader point, he said, is that the age of autonomous agents will create many failure modes people have not considered yet.
John suggested that smart contracts and decentralized identity may help solve some of that. Rob agreed that the field is still wide open and that nobody knows what the final form will look like.
He still thinks October fits the cycle better than August
Late in the interview, John asked whether the market might be out of the bear phase by November, when he plans to attend Ben Cowen’s Investing Through the Cycles conference in Miami.
Rob said Cowen had framed the event as a kind of test: if a conference can work in the worst part of a bear market, the next year should be better, the following year would bring the halving, and the year after that would be the major bull run.
As for price, Rob said he still sees October as the likely timing for a cycle low. He repeated the same possible bottom levels: $55,000, $50,000, or $45,000. If Bitcoin were to hit $45,000 in October, he said, then a move back toward $50,000 to $55,000 in November would make him happy because it would mean he had been buying aggressively at lower levels.
His base case, though, was that November would probably still look weak and that more pain could come first.
There was an ironic turn at the end of the discussion. As they were talking, John said Ether had broken above $2,000 and Bitcoin had moved above $68,000, joking that perhaps the show itself had called the bottom. Rob answered with a joke of his own: “Congratulations, we saved the whole market.”
That exchange captured the tension in the episode. Rob’s short-term call did not survive the next day’s rally. His larger message did: for a long-term investor, the focus is not on claiming perfect forecasts but on sticking to a buying, profit-taking, and risk-management discipline through the full cycle.