Rob, founder and host of Digital Asset News, said on The Milk Road Show that he still believed Bitcoin might not have bottomed yet and that the low could arrive around October, potentially near $55,000, $50,000 or even $45,000. The timing was awkward. The episode was recorded on Aug. 19, and on Aug. 20 Bitcoin surged about 10%, briefly moved above $70,000, hit its highest level since early June, and triggered the largest short liquidation wave since 2021. More than $1 billion in short positions were wiped out in a single hour.
That miss on the near-term move was part of the story, but not really the point of the conversation. Rob’s main message was about process rather than prediction: buy harder into weakness, scale out on the way up, and treat missed tops as part of the game.
Recorded before the rally
The episode, sourced from Milk Road and titled Bitcoin Just Pumped… But Is the Bear Market Really Over?, aired on Aug. 19, 2026. Host John Gillen spoke with Rob, who entered crypto in 2017 and has publicly shared his dollar-cost averaging approach for years. The program also disclosed that Rob is an independent content creator who holds Bitcoin and a small amount of altcoins, and that the discussion reflected his own investing practice rather than any fundraising effort or product tie-in.
Rob still sees the 200-week moving average as a buying zone
Gillen opened with Bitcoin’s move back above the 200-week moving average, a level many market participants have historically treated as a bear-market floor. He asked whether the market had already bottomed or whether more downside was still ahead.
Rob’s answer was blunt: he hoped the bottom was not in yet because that would give him more room to buy lower. Looking back, he said the area around the 200-week moving average has repeatedly offered attractive entries. In 2015, Bitcoin only slipped below it briefly. In the 2018 cycle, after the 2017 peak, the break below prompted widespread capitulation talk, but investors who kept averaging in were rewarded later. The same was true during the 2020 pandemic shock. In 2022, he noted, Bitcoin even fell below the 200-week, 250-week and 300-week moving averages.
For him, price action around the 200-week level still looks like a workable accumulation zone. He said he does not want to repeat what he called his "mini DCA" mistake from 2022, when he bought less as price fell because he kept waiting for a much lower level to make a larger purchase. In hindsight, he said he would have been in a far better position had he simply stuck to the original plan and bought more aggressively on the way down.
He pointed to Bitcoin bought around $3,000 in 2018 and Bitcoin bought around $15,000 to $17,000 in 2022 as examples that did not look bad later.
How his Monday DCA system works
Gillen noted that Rob is known for buying Bitcoin every Monday and asked how the strategy is structured when bear markets can move sideways for months. He also asked whether the same kind of scaling logic applies on the way out.
Rob said he uses the risk meter from Ben Cowen’s Into The Crypto Verse as a reference point. As price drops and risk falls, he raises the size of his buys. The framework he described is straightforward:
- He starts buying when the risk level is around 0.5 to 0.6.
- If it drops below 0.49, he doubles the size of the prior Monday’s purchase.
- At 0.39, he buys four times as much.
- Below 0.29, he buys eight times as much.
Those adjustments are manual, he said. Execution runs through Cash App’s recurring purchase feature at 6:30 a.m. every Monday, with fees that are "almost negligible" and solid spreads. At the time of recording, he said the risk reading was roughly 0.3, which put him in what he described as the four-times buying phase. He added that his bank used to call to confirm the larger transactions, but does not anymore.
On selling, Rob said he handled 2021 better than 2025. In 2021 he used price targets and scaled out in stages, taking some profit after a 2x move from the lows and more after a 4x move. In 2025 he tried to be smarter by relying on indicators such as Pi Cycle Top, MVRV and Puell Multiple, but said they all disappointed him. The call that actually lined up with the top, he said, came from a Reddit post written three years earlier that named Oct. 6, 2025 as the absolute peak. He thought that was impossible at the time, but said it ended up being right.
He sold some on the way down rather than at the high and said that does not bother him because he does not believe anyone consistently nails the exact top. Rob also pushed back on blanket claims that Bitcoin should never be sold. Investor goals differ, he said. Part of his reason for taking some profit was to pay off debt and move funds into what he views as steadier assets, including the S&P 500, bonds and real estate, while keeping most of his exposure in Bitcoin rather than altcoins.
Near-term catalysts look limited to him
Gillen pointed out that Bitcoin’s volatility had dropped to record lows in recent months, even below gold and equities, and asked what event might finally break that standoff.
Rob did not sound convinced that a strong positive catalyst was close. On the downside, he mentioned the possibility of an AI bubble breaking or another large-scale hardware wallet hack. On the upside, he said passage of the CLARITY Act would matter, but he does not think it gets through.
His reasoning was political. In a midterm election year, he said, Democrats are unlikely to hand Trump a victory lap on crypto. He also mentioned ongoing institutional developments, including what he had just seen about Citigroup, which he described as the world’s third-largest bank, moving into Bitcoin custody. Even so, he said that while the U.S. has a president who campaigned as pro-crypto, many promises are still hard to deliver, especially on the CLARITY Act.
That leaves him cautious on the near term. Congress has disappointed the industry repeatedly in his view, and while the Securities and Exchange Commission and the Commodity Futures Trading Commission may fill some of the gap, he does not expect that to be enough on its own. He said the larger move may have to wait until later in the year, when the market’s fixation on the four-year cycle starts to ease and sentiment can shift.
White House meeting and CLARITY Act: "posturing" more than breakthrough
Gillen then brought up the policy backdrop. The CLARITY Act had been delayed until September, and on the day of recording Trump was meeting crypto industry figures at the White House. Was anything concrete likely to come from it?
Rob said he hoped so, but was skeptical. He had just seen that World Liberty Financial received a conditional bank charter from the Office of the Comptroller of the Currency and wanted to use that position to move into stablecoins. He added that its stablecoin was already the fifth largest. Stablecoins backed by reserves can strengthen the dollar’s role globally, he said, but he also questioned how smoothly any policy push would go when the president’s own company stands to benefit.
His takeaway was that he can control his own investment universe, not how a U.S. president chooses to run a crypto business. If the White House meeting produces something useful and moves Congress forward, he said, that would be welcome. But his baseline view is that the event looks more like posturing than a decisive step. He is not expecting much from September either.
SEC’s new framework may reopen fundraising, but too late
The discussion then turned to the SEC’s newly approved "Regulation Crypto" framework, which Gillen described as covering ICOs, fundraising and innovation exemptions for networks still under construction. The obvious tension, he said, is that 2017-style ICO cycles created plenty of rug pulls even as they also funded experimentation.
Rob’s answer was that Washington is roughly five or six years late. When he first entered crypto in 2017, ICOs were everywhere. A framework like this at that time, he said, could have helped many legitimate projects raise money earlier and more cleanly.
He said one part of the rule set appeared to allow offerings up to $5 million with little friction, while another tier covered up to $75 million over four years. If those terms hold, capital could return to the crypto sector. Still, he questioned whether the industry really needs more new projects and more altcoins when millions already exist.
His own preference is to stick with assets that have already been tested and to watch what gets built on top of them. He welcomed clearer guardrails from the SEC and CFTC, saying they should help avoid the lawless feel of earlier cycles, but he stopped short of calling the framework a make-or-break catalyst.
Rob also spent time on perception outside crypto. Many people, he said, still see the sector as the place for meme coin speculation and hacked funds. He cited this year’s Coinbase Super Bowl ad, saying the room’s energy shifted to boos when Coinbase appeared because that was where people had lost money. He also mentioned Trump coin and Melania coin as examples that hurt another wave of participants. Guardrails help, he said, but what the sector needs most is not a larger pile of filler projects. It needs projects that actually change the game.
After wallet incidents, he is diversifying custody too
On self-custody, Gillen brought up the recent string of incidents involving Coldcard, Trezor and SafePal and asked what that means for people who want to hold their own keys.
Rob said some observers frame the timing as suspicious, especially with institutional custody services such as Citi’s expected to come online, but he does not think the conspiracy angle matters much. What matters is that people lost money. He pointed to PlanB, who he said moved all of his holdings into ETFs two years earlier. According to Rob, PlanB understands cold storage as well as anyone but simply no longer wanted to deal with the operational burden. On the other side, he said Simon Dixon views the trend as an effort to push users away from self-custody and toward custodians.
Rob said he receives emails every week or two from people who have lost their savings. The problem is not limited to user mistakes. Firms such as Ledger and SafePal have also had breaches that exposed addresses, email accounts and phone numbers. The risk that worries him most is not knowing what he does not know. If a major wallet were to disclose a vulnerability that had gone unnoticed for years and hundreds of thousands of users lost Bitcoin, the damage would be severe.
His response has been to diversify security itself. He said he now spreads holdings across Ledger, Tangem, iTrust custody, Coinbase Prime and ETFs. He added that Coinbase Prime is used by Strategy and BlackRock.
He put the issue in personal terms. He does not want to be the person who has to go home and say that the Lazarus Group stole the family’s savings. He also cited Steve Wozniak, saying Wozniak had put $3.2 million into Bitcoin and still got scammed out of it. Losing 25% hurts, Rob said, but losing 100% with no control is worse.
For altcoins, he mainly watches four chains
Asked whether altcoins are part of his DCA plan, Rob focused less on broad token picking and more on stablecoin activity. He said stablecoins should continue to grow and that the trend supports the dollar.
Citing Visa’s on-chain data, he said the biggest stablecoin traffic consistently sits on four chains: Binance, Ethereum, Solana and Tron. He grouped them together under the label "BEST." Polygon is worth discussing, he said, and he understands the cross-border payments case pitched by XRP supporters, but his capital is finite and he does not want to spread it too thin.
Payments are only one piece of the picture in his view. Speculation remains the larger force, and beyond that he sees tokenization of real-world assets as another major track, spanning bonds, equities and real estate. Ethereum looks like the chain of choice for institutions and Wall Street, he said, even though DeFi hacks hurt perception. Tron, by contrast, is Tether’s heavyweight network, with more than 60% of Tether volume on Tron.
He also mentioned Canton as a major player in tokenization and Hyperliquid as an active venue in perpetuals, but said neither is enough to make him rebalance today. His bottom line was simple: if traditional markets sneeze, Bitcoin gets the flu, and altcoins end up in the ICU.
The next cycle narrative he likes most: AI agent payments
To close, Gillen asked which future narrative looks strongest to him: tokenization, stablecoins or AI agent finance. Rob picked AI agent payments.
His reasoning started with time. Time is the one thing people cannot buy back, he said, so a useful autonomous agent that can arrange a trip to Puerto Rico, pay at very low cost and even earn rewards would be compelling. He tied that idea to Cloudflare’s announcement the previous week that it would support crypto payments for AI agents. In his telling, this kind of machine-to-machine payment would not carry something like PayPal’s 2.9% plus $0.30 fee. It could drop to fractions of a cent.
He did not present that future as risk-free. Rob immediately raised the question of what happens if the agent goes off the rails. He recounted a story about a developer who told an AI system to clean up an email inbox, only to have it delete every file on the computer. The implication was clear: an agent-driven economy may introduce whole classes of failure that people have not thought through yet.
Gillen suggested smart contracts and decentralized identity might become part of the answer. Rob agreed the field is still wide open and said nobody really knows what the end state will look like.
He still expects a possible October bottom under the four-year cycle view
Gillen also asked about Ben Cowen’s Investing Through the Cycles event in Miami this November and whether the market could be out of the bear phase by then.
Rob said Cowen’s original idea was that if the event could be launched in the ugliest part of the bear market, the following year should be better, the year after that would be a halving year, and the next one after that could be a full-blown bull market. In that sense, he said, the conference itself is a kind of test.
As for the market, Rob stuck with the four-year cycle framework. He said the bottom should land around October, with the open question being whether that means $55,000, $50,000 or $45,000. If Bitcoin really fell to $45,000 in October, he said, he would be happy to see it back around $50,000 to $55,000 in November because that would mean he had been buying aggressively at lower levels. His broader expectation, though, was that November would still look sluggish and that more pain could come first.
Near the end of the show, Gillen noted that Ethereum had already broken above $2,000 and Bitcoin had climbed past $68,000 while they were talking, joking that maybe they had just talked the bottom into existence. Rob answered in kind: congratulations, we saved the whole market.