A conversation with a crypto OG who entered the market in 2017: Bitcoin's 10% surge was unexpected, and AI-assisted payment is the narrative for the next bull market?

Guest: Rob, founder and host of Digital Asset News (X: @NewsAsset), entered the crypto market in 2017, and has long been publicly sharing 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?

Broadcast Date: August 19, 2026

Disclosure of Interests: Rob is an independent content creator. He has disclosed in the program that he holds Bitcoin and a small amount of altcoins. He is sharing his personal investment practices and has no interest in external fundraising or related products.

Key points summary

This episode was recorded on August 19th, the day before the Bitcoin surge. The guest, Rob, is the host of the YouTube channel Digital Asset News. He entered the market in 2017, completed a full cycle, and publicly disclosed his investment methods: referencing Ben Cowen's risk meter, buying more as prices fell. His core judgment was simple: the area around the 200-week moving average has historically been a buying zone. In the short term, he maintained a "healthy pessimism" about the market, believing that based on a four-year cycle, the bottom would be around October, potentially falling to $55,000, $50,000, or even $45,000. However, the day after the recording, on August 20th, Bitcoin surged by about 10%, briefly breaking $70,000, a new high since early June, triggering the largest short-selling liquidation wave since 2021, with over $1 billion in short positions liquidated in just one hour.

Rob's short-term price level predictions were quickly proven wrong by the market, but what he really wanted to talk about wasn't prediction, but the real discipline of a long-term individual investor: buy more as prices fall, take profits in batches, and treat selling too early as tuition. This episode also discussed the Clarity Act and the White House meeting (his conclusion was "posturing"), the new SEC framework and the return of ICOs, how to diversify self-custody after the cold wallet collapses, altcoins only recognizing four blockchains, and the narrative of AI-assisted payments as the next bull market.

200-week moving average: Is the bottom here, or halfway up the mountain?

John: Bitcoin has climbed back above the 200-week moving average, which historically often marks the bottom of a bear market. But sometimes the price lingers around that level for a long time. Do you think we've bottomed out, or is there more of the bear market to come?

Rob: I hope it hasn't bottomed out yet. Looking back, the 200-week moving average has always been a good buying opportunity. In 2015, we barely dipped below it; after I entered in 2018, it dipped below it once after the 2017 high, and everyone said it was over and would never come back, but the smart people just quietly continued dollar-cost averaging. Then there was the 2020 pandemic, which also dipped below it, another good buying opportunity. By 2022, we even dipped below the 200-week, 250-week, and 300-week moving averages. Now the price is hovering around the 200-week moving average, and it's probably above it right now. **For me, this is a pretty good time to buy.** I don't want to repeat the mistake I made in 2022, when I did something stupid called "mini DCA," buying less as the price went lower, thinking I'd wait until it dropped very low before buying all at once. If I had stuck to my original plan and bought more as the price fell, the position would be much better now. **Buying Bitcoin at $3,000 in 2018 and then at $15,000 to $17,000 in 2022 would have been profitable in retrospect.** So, back to your question: I hope it hasn't bottomed out yet. Let's see if this four-year cycle follows the script again, or if this is just a good buying opportunity.

Weekly DCA: The steeper the drop, the more you buy.

John: You're known for your weekly DCA on Bitcoin. In a bear market, the price can stay sideways for months. How do you design this strategy? Do you also use the same method to sell in batches during a bull market?

Rob: I look at the risk level, which I refer to from Ben Cowen's Into The Crypto Verse risk level indicator. As the price goes down, the risk level also goes down. I start buying around 0.5 or 0.6; if it falls below 0.49, I double my purchase based on last Monday's levels; at 0.39, I quadruple; and below 0.29, I quadruple. These are all manually adjusted by me. I buy through Cash App's recurring purchase program, which executes automatically at 6:30 AM. The fees are almost negligible, and the spreads are good. Currently, the risk level is around 0.3, so I'm roughly in the quadruple buying phase. **Whenever I bought a lot, the bank would call to ask if it was me making the purchases, but they don't call anymore.** On the selling side, I did quite well in 2021 by setting price targets and selling in batches, using fractal analysis. I would take profits when the price doubled from the low, and then take profits when it quadrupled. By 2025, I felt I should use indicators, which seemed smarter, so I looked at Pi Cycle Top, MVRV, and Puell Multiple, but they all disappointed me. The one that truly predicted 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 it really was. So I took some profits during the decline, not selling at the absolute peak, and I don't think anyone can truly sell at the absolute peak. I know many people say never sell Bitcoin, but everyone's goals are different. I sold a portion to pay off debts and move it into safer assets, like the S&P 500, bonds, and real estate, so I could sleep soundly at night. The majority of my holdings remain in Bitcoin, not in altcoins.

With volatility ridiculously low, what can break the deadlock?

John: Bitcoin's volatility has hit record lows in recent months, lower than both gold and stocks. What immediate events do you see that could break this trend?

Rob: It's hard to say. On the downside, the AI bubble might burst, and cold wallets could suffer another large-scale hack. On the upside, it would be great if the Clarity Act passed, but I don't think it will. It's a midterm election year, and the Democrats won't let Trump win this round, giving him a chance for a victory tour. There's been a lot of news from institutions; I just saw that Citigroup, the world's third-largest bank, is starting to offer Bitcoin custody. We also have a president who promised to support crypto during his campaign, but he hasn't delivered on many of his promises, especially the Clarity Act. **In the short term, I don't see many positive catalysts. Congress has consistently disappointed us. The SEC and CFTC will fill the gap, but that help will be limited.** A major market move will have to wait until after this year, because everyone's mindset is dominated by the four-year cycle. Only after this cycle ends will market sentiment shift, and prices will truly begin to rise.

The Clarity Act and the White House Meeting: Don't Have Too High Expectations

John: The Clarity Act has been delayed until September. While we were recording today, Trump was meeting with a bunch of crypto industry leaders at the White House. Do you think there will be any substantial results?

Rob: I hope so, but I just saw that World Liberty Financial got a conditional banking license from the OCC. They want to use it to enter the stablecoin business; their stablecoin is already the fifth largest. This is beneficial for strengthening the dollar's global position, as stablecoins need reserves behind them. But the president wants to push it forward because it's good for his own company, and I don't think it will go smoothly. **I can only control my own investment scope, not the US president running his own crypto company. If he can make some progress with the industry and get Congress to move forward, that would be great, but to me it seems more like a gesture.** The bill might pass in September, but I don't have high hopes.

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

John: The SEC has passed a framework called "Regulation Crypto," which covers ICOs, fundraising, and grants innovation exemptions to projects with networks still under construction. What are your thoughts? The ICO boom of 2017 also brought a bunch of bad pulls. How can this contradiction be resolved—wanting industry vitality on one hand and investor protection on the other?

Rob: The government is about five or six years late this time. When I first entered the crypto space in 2017, ICOs were everywhere. If this framework had been in place earlier, many good projects could have secured funding. I looked at the details; there's basically no threshold for investments under $5 million, and another tier is $75 million over four years. If this were implemented, money would flow into the crypto industry. But I'm worried about one thing: do we really need more new projects and more altcoins? There are already millions. I'll stay on proven projects and build upon them. It's good that the SEC and CFTC have installed the safeguards; they won't be as lawless as before, but I don't think it's a decisive catalyst, though I might be wrong. As for how outsiders view us: they'll just say, "That's the one that plays with meme coins and just got hacked." Watch the Coinbase ad during this year's Super Bowl; it started with a chorus, but when it switched to Coinbase, the whole audience booed because that's where they lose money. Trump coin and Melania coin have scammed a lot of people again. Barriers are a good thing, but what we need are projects that can truly change the landscape, not just more filler projects.

Following the series of cold wallet failures: Even self-custodied wallets need to be decentralized.

John: Last week, Coldcard, Trezor, and SafePal all ran into trouble, making people uneasy about self-hosting. What are your thoughts?

Rob: Some might say it's a coincidence, since Citibank and other custody services are about to launch. But remember, Coldcard has been around for years. Conspiracy theories don't matter; what matters is that many people have actually lost money. **PlanB said two years ago, "I've moved everything to an ETF." He knows more about cold storage than anyone, but he said he didn't want to deal with these headaches anymore.** Simon Dixon on the other hand said this is to drive people from self-custody to custody. In my case, I receive an email every week or two from someone saying they've lost all their savings. It's not just because of operational errors and being hacked; companies like Ledger and SafePal themselves have been hacked, with addresses, emails, and phone numbers all leaked. The scariest thing is "not knowing what you don't know." What if a mainstream cold wallet suddenly says in the future, "We've had a vulnerability we haven't discovered," and hundreds of thousands of people's Bitcoin is gone? So now I'm diversifying my security: part in Ledger, part in Tangem, part in iTrust custody, part in Coinbase Prime (the one Strategy and BlackRock use), and part in an ETF. I refuse to be the kind of person who goes back to his wife and says, "Lazarus Group stole all our savings." Steve Wozniak invested $3.2 million in Bitcoin and still got scammed. Losing 25% is painful, but the worst is losing 100% and having no control over it. I'd rather protect more people than leave them all to bear the burden alone.

Altcoins: I only recognize these four chains

John: Besides Bitcoin, are altcoins also on your DCA list?

Rob: Stablecoins will thrive, especially strengthening the US dollar. Looking at Visa's on-chain data, the four chains with the largest stablecoin traffic are always Binance, Ethereum, Solana, and Tron—I call them the BEST. Polygon is worth discussing, and XRP people will talk about cross-border payments, which I understand, but my funds are limited. **Payments are only one aspect; the biggest factor is speculation.** Further down the line is the tokenization of real-world assets—bonds, stocks, and real estate can all be on-chain. Ethereum seems to be the choice of institutions and Wall Street, although the DeFi hacks have negatively impacted its image; Tron is a behemoth of Tether, with over 60% of Tether's trading volume on Tron. Canton has a large share in tokenization, and Hyperliquid is very active in perpetual contracts; they're all good, but not enough for me to adjust my portfolio right now. **A sneeze in the traditional market, Bitcoin catches the flu, and altcoins go straight to the ICU.** This is the transmission path of digital assets.

The next narrative and "bottoming out in October": AI agents pay, who will cover the losses?

John: Tokenization, stablecoins, AI-assisted finance—which of these narratives do you favor the most? You're going to Miami in November for Ben Cowen's Investing Through the Cycles conference. Do you think we'll emerge from the bear market by then?

Rob: I love AI-powered payment agents because there's one thing you can never buy: time. If I had a robot that wouldn't destroy me, could plan my entire trip to Puerto Rico, pay with incredibly low fees, and even give me a commission, that would be fantastic. Cloudflare just announced last week that it will integrate AI agents for cryptocurrency payments, with fees not like PayPal's 2.9% plus 30 cents, but only a fraction of a cent. **But the problem is, what if the AI agent goes crazy?** There's a story about a developer who asked AI to clean up his email inbox, and it ended up deleting all the files on his computer. The age of robots will bring many more "unforeseen" things. John is right; smart contracts and decentralized identities might be the solution, but it's still a blue ocean market, and nobody knows what it will look like. Returning to Ben's conference, he said that if he could hold the conference during the worst of the bear market, next year would be better, the year after that would be half a year shorter, and the year after that would be a massive bull market. This conference is a litmus test. Based on a four-year cycle, we should bottom out around October. How low? 55,000? 50,000? Or 45,000? If it really drops to 45,000 in October, then November will likely be between 50,000 and 55,000, which would make me very happy, because it means I've been buying at very low prices. However, I predict that November will still see prices hovering at low levels, and there may be some more pain ahead.

John: As we were talking, Ethereum broke through $2,000, and Bitcoin reached over $68,000. Maybe we'll figure out the bottom for Bitcoin today.

Rob: Congratulations, we saved the entire market.