Conversation w/ Ron Santella, OpenAI ($852B) Bigger Than JPMorgan, & Prediction Market Lawsuits

Summary

Rich Habits Podcast – April 3, 2026
Episode: "Conversation w/ Ron Santella, OpenAI ($852B) Bigger Than JPMorgan, & Prediction Market Lawsuits"
Hosts: Austin Hankwitz (A) and Robert Croak (B)
Special Guest: Ron Santella (C), founder of Equable Shares

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Episode Overview

This week’s Rich Habits Radar dives into the biggest financial headlines affecting investors:

• President Trump’s primetime address on the Iran conflict and its effects on global markets.
• OpenAI’s colossal $122 billion funding round, pushing its private valuation to $852 billion—larger than JPMorgan and Visa.
• A landmark legal clash between federal regulators and states over prediction markets, which could redefine gambling and financial market boundaries.
• Special in-depth interview with veteran hedge fund manager Ron Santella, unpacking market volatility strategies for uncertain times.

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Key Discussion Points and Insights

1. Trump Address on Iran War and Market Turbulence

(Timestamps: [00:15]–[06:27])

• Summary: President Trump’s nationwide speech on the Iran conflict failed to provide a strategic path forward, reiterating previous talking points. Instead of offering clarity, his comments increased market uncertainty.

• Market Response:

  • S&P 500 futures lost $550B in market cap within 25 minutes post-speech.
  • Oil surged above $100/barrel; global markets dropped 2–4% overnight ([02:47]).
  • Asian indices, e.g., South Korea and Japan, saw significant losses.

• Takeaways for Investors:

  • Robert: “Markets hate uncertainty more than they hate bad news.” ([03:19])
  • Austin: Reiterate importance of capital preservation and discourage trying to time market headlines. Encourage recurring investments in index funds/ETFs and building a ‘shopping list’ of undervalued quality names (e.g., Microsoft) ([04:20]).
  • Robert: “Arm yourself with the best information. But most importantly, don’t try to time the markets and have knee-jerk reactions.” ([05:41])

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2. OpenAI’s Record-Breaking Funding & AI’s Investment Landscape

(Timestamps: [06:27]–[11:18])

• OpenAI Milestone:

  • Closed a $122B funding round; now valued at $852B ([06:27]).
  • Main backers: Amazon, Nvidia, SoftBank contributed $110B; retail investors got in via banks ([07:05]).
  • Purpose: Building a base of shareholders ahead of a highly anticipated IPO.
  • OpenAI to be included in certain ARK Invest, T. Rowe Price, and Fidelity funds ([07:37]).

• Strategic Pivot:

  • Shuttered their Sora video generation tool, pivoting to super-apps and enterprise software, particularly coding assistants ([08:17]).
  • Disclosed $2B/month revenue, projecting $24B/year ([08:17]).
  • Massive spending: Projected to burn $115B by 2029 ([09:02]).

• Investment Implications:

  • Austin: Highlights evolving business model—moving away from consumer to enterprise focus for stronger revenues.
  • Robert: At current valuation, OpenAI trades at ~35x sales. “Bulls say generational shift, bears point to profit timeline...” ([11:18])
  • Quote/Outlook:
    • “122 billion in a single funding round means the smartest money in the world is making the biggest bet in venture capital history that AI is here to stay and it is definitely worth it.” – Robert ([11:18])

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3. Prediction Market Lawsuits: Gambling or Financial Innovation?

(Timestamps: [11:18]–[18:01])

• Regulatory Showdown:

  • CFTC sues Illinois & Connecticut to stop them from applying gambling laws to prediction markets (e.g., Kalshi, Polymarket, Crypto.com), setting up a potential Supreme Court case ([11:18]).
  • Federal View: CFTC argues these are federally regulated derivatives, not gambling ([12:38]).
  • States’ View: Bipartisan attorneys general say they're gambling disguised as finance ([13:09]). Arizona even filed criminal charges against Kalshi’s parent company.

• Why It Matters:

  • Robert: “Prediction markets are a great indicator...it’s people betting with real money on what they think the outcome is going to be.” ([15:35])
  • Supreme Court may decide who regulates multibillion-dollar markets; outcome could instantly legitimize national prediction markets ([17:38]).

• Investor Takeaways:

  • Prediction markets generate leading information on elections, geopolitics, Fed actions ([14:11]).
  • Growth will benefit data companies, payment processors, and exchanges (e.g., Polymarket’s data partnership with Dow Jones).

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4. Rapid Headlines: Rich Habits ‘Radar Points’

(Timestamps: [19:54]–[28:45])

Robert’s Radar:

• SpaceX Files for IPO: May be “largest initial public offering of all time,” seeking $1.75T valuation ([19:54]).
  • Early Rich Habits Network investors may have an 8x return since 2024.
• Microsoft: Investing $5.5B in AI/cloud infra in Singapore and $1B in Thailand ([21:10]).
  • “Microsoft stock selling off so aggressively, now could be a time to nibble back in.” — Robert
• Tokenized Stocks/Real Estate:
  • Securitize partners with BlackRock, Apollo, KKR—tokenized $16B of assets in 2025.
  • Expect $3T in tokenized real estate by 2035.

Austin’s Radar:

• Oracle Layoffs: Up to 30,000 layoffs as Oracle doubles down on AI infrastructure, funded by new OpenAI partnership ([24:54]).
• Google’s “Gamma 4” Model: New open-source model for advanced reasoning & agentic workflows. Over 400 million downloads of prior versions ([24:54]).
• Bond Market’s 68-Month Drawdown: The longest bond bearish stretch ever, fueled by energy/inflation risks post-pandemic. “Type in agg on your platform...Not good, not good.” — Austin ([26:55])

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5. Special Interview: Ron Santella on Market Volatility, Hedging, and Investor Mindset

(Timestamps: [29:09]–[43:52])

Ron Santella’s Background & Approach

• 40 years in options, arbitrage, and risk management.
• Focus: Help investors stay invested but hedge downside via strategies like HEDG ETF.

Notable Quotes & Insights

• On headline risk: “We’re in a much more news sensitive environment than we’ve ever been before.” ([31:13])
• On market timing: “It’s very hard to time markets... picking the right time to enter or exit can be pretty tricky.” ([31:13])
• Strategy:
  • HEDG ETF: Long S&P 500 (via SPY & IVV), overlays call writing and put spreads for defined outcome, rules-based hedging ([33:31]).
  • “We’re that solution right in the middle for those who want exposure to the S&P 500.” ([33:31])
  • Insurance analogy: “If you own a car, you’re going to have car insurance...[HEDG] is like insurance for your portfolio.” ([41:59])

Biggest Investor Mistakes & Lessons

• “Every investor should start with a plan... [otherwise], that’s quote: a mistake.” ([37:07])
• “Emotions drive markets...I had to really extricate emotion from the decision process.” ([37:07])
• The classic 60/40 portfolio was exposed in 2022 as not always resilient; liquidity risk is underappreciated ([39:20]).
• Importance of understanding one’s personal risk tolerance: “Most people just want to get rich, but they don’t have a real plan.” – Robert ([38:09])

Diversification and Staying Invested

• “Don’t try and time a hedge.” HEDG can provide consistent, defined protection in up or down markets ([41:59]).

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Highlight Quotes & Memorable Moments

• Austin on Market Overreaction ([05:41]):

  “Don’t try to time the markets and have knee-jerk reactions. Build that muscle to not be reactive to headlines, especially bad news.”

• Robert on Information Edge and Prediction Markets ([15:35]):

  “These are real people betting with real money… a great indicator and tool for people to know where the markets are going.”

• Ron Santella on Planning ([37:07]):

  “Every investor should start with a plan... emotions drive markets… extricate emotion from your decision process.”

• Ron Santella on Portfolio Construction ([41:21]):

  “An investor should have their money in growth areas of the market and benefit from positive moves… but… have some insurance in your portfolio.”

• Robert on Tokenization ([24:21]):

  “As more and more asset classes get put on blockchain rails and become tokenized, it’s going to make things quicker, more effective, better cost structures... better for the everyday investor.”

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Actionable Takeaways

• Don’t panic-sell or time market headlines; stick to a disciplined investing plan.
• Consider diversified exposures: index funds as a core, with satellites in emerging asset classes (AI, tokenization, hedged products).
• Monitor AI investments—even if not directly buying OpenAI, be aware of indirect exposure through funds.
• Use prediction markets as an information edge, but treat them as tools, not gambling.
• Assess personal risk tolerance, plan portfolio construction, and ensure you have liquidity and downside protection.

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Notable Timelines

• [01:20] – Trump’s Iran speech and markets’ whipsaw.
• [06:27] – OpenAI’s $122B raise; enterprise pivot.
• [11:18] – Prediction markets face regulatory test.
• [19:54] – Radar Points Lightning Round.
• [29:09] – Ron Santella interview begins.
• [33:31] – Explanation of HEDG ETF strategy.
• [37:07] – Santella on investor mistakes.
• [41:21] – Hedging in a balanced portfolio.
• [43:13] – Wrap-up with Ron's lasting advice.

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This episode delivers practical wisdom for riding market volatility, insight on transformative developments in AI investment, and a front-row view of regulatory battles shaping the next decade in finance. For any investor, these are the conversations—and habits—that can shape generational wealth.

Transcript

[A]

Protein is now at Starbucks and it's never tasted so good. You can add protein cold foam to your favorite drink or try one of our new protein lattes or matcha. Try it today at Starbucks.

[B]

You are listening to the Rich Habits Radar, a Friday episode of the Rich Habits podcast where every Friday morning we're coming at you with the biggest headlines impacting you and your money. This episode is brought to you by vcx, the public ticker for private tech. My name is Austin Hankwitz. I'm joined by my co host Robert Kroke. And the three things sitting at the top of our Rich Habits Radar this week include Trump addressing the nation on the Iran conflict, OpenAI's $122 billion in funding that was just announced, and the federal government suing states to keep prediction markets legal. That one's going to be fun to talk about, Robert. And be sure to stick around to the end where we talk about the 68 month bear market that bonds are finding themselves in right now. We also have a very special conversation with a former hedge fund manager who might have a solution to that problem. Cannot wait. So please stick around for that conversation. It's going to be a blast. Robert let's kick off this episode diving into our first story.

[A]

You yes, on Tuesday night, President Trump delivered his first primetime address to the nation on the Iran war, now in its third day. And what was billed as a major update turned out to be a defense of the war's progress with no clear strategy for any of us.

[B]

Trump said US Military objectives are nearing completion and predicted the mission would wrap up very shortly. But in that same breath, he said the US Would hit Iran extremely hard over the next two to three weeks with the goal of bringing them back to back to the Stone Ages. He threatened to strike all of Iran's electric generating plants very hard and probably simultaneously if no deal is reached. And he added that the US could hit their oil infrastructure as well on

[A]

gas prices, which crossed $4 a gallon this week for the first time since August of 2022. Trump called the increase short term and blamed it entirely on the Iranian attacks against commercial oil tankers and neighboring countries.

[B]

The entire setup going into Tuesday night was speech would de escalate things. Stocks had already rallied 2.9% the day before on Tuesday, the best days in the stock market since last May on hopes that Trump would signal an end to the conflict. But instead, he essentially repeated the same four talking points he's been making for weeks, which is the war is necessary. It's already been Won. It must continue, but it will also wrap up pretty soon.

[A]

And as expected, markets reacted immediately. S and P 500 futures erased fed $550 billion in market cap. Within 25 minutes of the speech, oil surged back above $100 a barrel and crude jumped to roughly $104. Asian markets got hammered as well overnight and South Korea's market dropped around 4% and Japan's Nikkei also fell around 2%.

[B]

So Robert, what does this mean for everyone listening right now? They got portfolios like we do. How should we be thinking about this stuff?

[A]

It means stay away from your screens right now and all of this settles down. No, really, it means this speech was supposed to be a catalyst for a sustained rally. Instead it reminded everyone that we don't have a clear exit strategy as of yet. And markets hate uncertainty more than they hate bad news. We all know how it happens. You see the headlines, they're bad. Everyone panics, they sell and they just don't know what to do. So that uncertainty really takes its toll on the markets. As we've seen as of late, oil is the variable that controls everything right now. When crude oil was at $119 earlier this month, the S and P was at its lows when it briefly touched $100. On ceasefire hopes we got the biggest rally in years. So you can see where this goes. And Tuesday night it pushed right back up above $103. Until there's an actual ceasefire, expect oil to whipsaw between $95 and $115 and, and expect stocks to follow.

[B]

Yeah, it reminds me, Robert, you know we've been talking about this theme of capital preservation for months now inside of the Rich Habits Network. And that playbook has not changed whatsoever. If the war does genuinely end right within the next two or three weeks, oil drops back to the 70$80 a barrel. We could see a snapback, right? Just like what we saw last April. It was with the Trump tariff tantrum headlines moving the markets like crazy. Then maybe we'll do any tariffs too quickly and the market snap back. V shaped recovery. So we're in a very headline driven market right now. But the key here for our listeners is do not try and time these headlines. Have a plan. You should be dollar cost averaging all the time, every week, every month into those long term index funds and ETFs that we talk about in your retirement accounts. And if you are someone who finds themselves a little bit of cash on the sidelines, maybe you're a little scared. For whatever reason, now is a Wonderful time because I've done this. So is Robert to find and make a shopping list of quality names that are trading just way below where they should be. I think Microsoft's a great example of this. We talked about how it's trading close to the 200 week moving average. They're crushing it right now. Microsoft seems undervalued to me. I bought a couple thousand dollars worth this week, but it's in that long term portfolio. Robert?

[A]

Yeah, I've never seen in 35 years of doing this, not the podcast, but being in the equity markets, I've never seen such reactive markets as it plays out to the headlines in the news. It's just crazy. We talk about this all the time and Austin, you and I have been doing this for over three years now and we're always telling people to be prepared and arm yourself with the best information. But most importantly, don't try to time the markets and have these knee jerk reactions all the time. So I'm really glad you brought that up because I think it's one of the hardest things for people to do is they have to be willing to build that muscle to not be reactive to headlines, especially bad news news, because it's just too difficult to try and get in and out of the markets all the time and try to figure it all out.

[B]

So let's now jump to our next story, which is OpenAI raising $122 billion in funding, which is the largest private funding round in history. So earlier this week, on Tuesday, OpenAI closed that largest funding round in Silicon Valley history at that $122 billion added to the bank account and $852 billion valuation. Mind boggling numbers here. To put that in perspective. OpenAI is now valued more than JP Morgan Chase, valued higher than Visa and valued about the same as Tesla, all while still being a privately held company.

[A]

Yeah, and it's crazy because Amazon, Nvidia and SoftBank committed to $110 billion of that total. The remaining 12 billion came from Silicon Valley and Wall street investment firms, plus a notable $3 billion from wealthy individual investors through banks. That retail slice is the tell because OpenAI is building a shareholder base ahead of the expected IPO by the end of the year. And they want everyday investors bought in before the listing, not after. And that's a key point here.

[B]

Yeah, I mean, we've seen some rattlings of different ways to invest in OpenAI right now on the public. Here's another couple ways. Right. So as part of this deal, OpenAI is going to get added to several ETFs that are managed by Cathie Wood. Ark Invest Ark's flagship $6 billion innovation ETF will have about 3% exposure to OpenAI. First time a private company has been held in that specific fund. Shares are also already small positions and mutual funds that are run by T. Rowe Price and Fidelity. So if you own those, congrats, that's cool. You might not even know you have expos. Pretty fun.

[A]

Well, let's talk a little bit about what they're doing with the money. Austin. OpenAI is in the middle of a major strategic pivot. They killed Sora, I think it was last week, the video generation tool. They hyped for over a year. And they are consolidating everything around this super app built for developers and business users. And so the focus is on productivity tools, particularly coding assistants. So the company said it expects roughly half of the revenue to come from enterprises by the end of this year already. And the revenue is real. OpenAI disclosed it's generating $2 billion a month, which puts it on a roughly $24 billion annual run rate. So big numbers here, lots of expectations in the works. So we'll see what happens.

[B]

The revenue's not just real, but so is the spending, Robert. OpenAI is projected to spend a total of $115 billion through 2029. And 17 billion of that, just scaling to 35 billion in 2027, 45 billion spent in 2028, that is more than Uber's entire annual revenue. And the cash from this round is going to give them the Runway to achieve that. But at that burn rate, right, you go spend 35, 45. Like that's a lot of money when you're not making that in revenue. So 122 billion. It's a good war chest. We'll see how it goes. Kind of a thought of as a down payment, maybe we'll get some more money from this ipo. But it's, it's an interesting one to say the least.

[A]

Yeah, it is crazy to think because we're so deep in AI right now and the world is betting the farm, as they say, on this AI sector. So, Austin, I can't wait to hear what does this mean for you and your money?

[B]

Yeah. So to your point, the world is betting on AI, and I think AI is real. I think it's okay to bet on that. Obviously, AI is going to be here to stay. It's not just a research project anymore. OpenAI very much is a full blown business. And the Business model is a lot more clear today than it was maybe two or three years ago. It's not consumer chatbots or Sora video generation apps. It's enterprise software. When OpenAI kills their flashiest consumer product, Sora, and they pivot to these hard coding tools and developer infrastructure, they are telling you that consumers, they'll pay 15, 20 bucks a month, but the businesses will pay 200, 400, 500. And that is where the value is derived from. That's the same playbook we're seeing from Microsoft, Salesforce, Oracle. They've run it for decades. Sell to businesses, not people. Now, for investors, it's an access question. You cannot go buy OpenAI stock right now. They're not publicly traded. But you can go buy Ark's Innovation ETF and get that 3% exposure. You can own those T. Rowe Price and Fidelity funds that hold those small positions. And of course, when that IPO hits later this year, very anticipated, you can go buy equity in OpenAI right on

[A]

public.com but here's the tension for me. At an $852 billion valuation on $24 billion in revenue, OpenAI is trading at roughly 35 times sales before it's even a publicly traded company. And that's expensive by any historical standard. The bulls will tell you AI is a generational shift and normal valuation metrics don't apply. And the bears will point to the $115 billion in projected spending and ask when this company actually turns a profit. Both sides have a very valid point. And that's the one thing that's not debatable on this scale. 122 billion in a single funding round means that the smartest money in the world is making the biggest bet in venture capital history that AI is here to stay and it is definitely worth it. That brings us to our next point. On Thursday, the CFTC sued Illinois and Connecticut in federal court to block those states from applying their gambling laws to prediction markets like kalshi, polymarket and crypto.com. it's the first time a federal regulator has sued states to defend these prediction markets. And it sets up what could become a landmark Supreme Court case over who gets to regulate the fastest growing corner of the financial markets here in the USA and abroad.

[B]

Markets have exploded since Trump's reelection in 2024. Platforms like Kalshi and Polymarket now let user bet on everything from MLB games to the reopening of the Strait of Hormuz. These platforms are registered with the CFTC as exchanges, and the bets on those exchanges are technically structured as financial derivatives. So the CFTC's argument is pretty straightforward. Federally regulated financial contracts and states have no authority to treat them as gambling.

[A]

The states see it differently. 39 attorney generals, Democrats and Republicans, signed a brief earlier this year arguing that these platforms are just online betting dressed up in financial language.

[B]

At stake is billions of dollars in tax revenue that these states are collecting from gambling that's already permitted in their states. Arizona took this one step further. Their attorney general filed criminal charges against Kalshee's parent company for operating a gambling business without a license.

[A]

Nevada also forced Kalshee to temporarily stop accept new sports bets, the first time the platform had to retreat under the state regulatory pressure. Now, here's the part that makes the story much more complicated. The Trump family has a direct financial interest in prediction markets. And one of Trump's sons serves as an advisor to both Kalshi and polymarket. And the CFTC Chairman Michael Selig was appointed by Trump last year and has been actively supporting these platforms all along.

[B]

Robert, why does this all now feel like an insider party we weren't invited to? The legal battle is likely headed to the Supreme Court. The CFTC said that Illinois and Connecticut lawsuits that are going through right now are intended to expedite a resolution of the multistate conflict. And a 9th Circuit hearing is scheduled for later this month involving Kalshee, Robin Hood and the North American Derivatives Exchange. The CFTC just announced they're hiring more enforcement staff specifically to police and insider trading on prediction markets, which tells you they expect this space to get much, much bigger, not smaller. So, Robert, for everyone listening, you know, we had that episode recently on the podcast talking about how people should be thinking about prediction markets, not as these like gambling platforms because we don't want anyone gambling on them. But there's a lot of useful information shared on these platforms about, you know, expectations on the Federal Reserve cutting interest rates when we think the Strait of Hormuz might be opened. I just saw, actually, if you read Rich Habits newsletter yesterday, we had a call out in there about how these prediction markets are expecting Democrats to sweep in 2028 for the first time, like ever. So it's really interesting stuff that's getting shared in bet on right now. But Robert, as these lawsuits come about, how should people be thinking about this from their own perspective with. With their money in their portfolios?

[A]

Yeah, I love this call out from you because I think it's really important for anyone leveling up their information and their knowledge about how to invest and where Prediction markets are a great indicator because it's not just some person at a news channel or at some newspaper or some blog telling you something. This is real people betting with real money on what they think the outcome is going to be. And I think it is a great indicator and tool for people to know where the markets are going and what people are thinking. I love them whether you're betting on them or not because of the informational strategies within there, I think is a great way for people to level up their knowledge. So, but let's get back to it. Prediction markets are creating a new asset class in real time right in front of us. You can already bet on geopolitical events, elections, sports, economic data releases and corporate outcomes. And if the federal government wins this fight and the Supreme Court rules that the CFTC has sole authority over these platforms, prediction markets will go from that gray area to being a fully legitimized national market overnight. Which I think is great, great, great to see these new ways for people to invest. Some may say gamble, but just giving more tools to the everyday person to better their financial lives.

[B]

Yeah, I'm not going to say using those platforms or investing. So I will let you be the one that says that. I will say though that for investors thinking about how can I profit from the rise of prediction markets. At the moment, Kalshi and Polymarket, privately held companies, join the Rich Habits network. Maybe we'll have an opportunity to invest in them in the future. We've actually been offered it a couple times, but we passed because of the weird fees associated with some of that. But the infrastructure companies that are going to benefit from prediction market growth are public exchanges, payment processors, data companies. For example polymarket, they already have a data partnership with Dow Jones, which means as this market scales, you should expect more partnerships, more data products and maybe even their own public like listings.

[A]

So the bigger question is philosophical. Are prediction markets gambling or are they financial instruments? The answer to that question will determine whether this becomes a multi trillion dollar industry or gets regulated into irrelevance. Right now the federal government is betting on the former and they're putting the full weight of the CFTC behind it. So we will keep a watchful eye and keep all of you updated.

[B]

Now before Robert, we jump to our radar points and the awesome conversation that we will have with the former hedge fund manager. Got to give a shout out to vcx, the public ticker for private tech.

[A]

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[B]

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[A]

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[B]

Visit get VCX.com for more information. That is get VCX.com Please carefully consider the investment material before investing, including objectives, risks, charges and expenses. This and other information can be found in the Fund's [e-mail] this is a paid sponsorship. Please go listen to our conversation with Ben Miller, the CEO of fundrise, who is also the CEO of vcx. If you think about it that way, tons of great information in that interview. We'll link it in the show notes below. Understand the risks. Understand everything that comes with owning shares of vcx. Robert let's jump to the radar points. I know you've got some good ones here, so I vote you go first.

[A]

I will gladly go first in my three points today are SpaceX officially files to go public, Microsoft plans to invest $5.5 billion in Singapore, and tokenized stocks are coming to America sooner than you think. Let me get into it right now. Elon Musk SpaceX is one step closer to staging what could be the largest initial public offering of all time. The company has confidentially filed IPO paperwork with the securities and Exchange Commission. SpaceX is aiming for an IPO that could raise between 40 billion and $80 billion, and the Wall Street Journal has reported the filing puts the company on track to potentially list shares in July. I'm so excited for this one, especially as they aim to raise at this $1.75 trillion valuation. I can't believe I'm saying that for an IPO, but if you're part of the Rich Habits Network, you might remember us offering an investment opportunity in SpaceX at a $220 billion valuation. And there were dozens of our members that invested and now are up theoretically an 8x on their investment made back in September 2024. So join the network. We have all kinds of really cool opportunities for all of our members. My next one today that I'm super excited about is Microsoft is on Track to invest $5.5 billion in cloud and artificial intelligence infrastructure in Singapore through 2029. Their Vice Chair and president Brad Smith said the following Our ongoing investment in cloud and AI infrastructure reflects Microsoft's long term confidence in Singapore as a long term global digital leader. We're focused on helping people and organizations use AI by strengthening skills, increasing cybersecurity and resilience, advancing trusted governance. The announcement came a day after Microsoft said it plans to invest over $1 billion in Thailand. With Microsoft stock selling off so aggressively, now could be a time to nibble back in and have 2029. You can thank yourself you did. And my last point today that I want to cover that I think is very important for the future of US equities in real estate and everything else is that tokenized equities, which are essentially digital replicas for stocks traded on blockchain rails, allow people to trade 24, seven and clear trades in seconds rather than days. US regulators don't permit American investors to own tokenized stocks yet, but is allowed in many international markets. And platforms like Robinhood Markets in Kraken are making tokenized trading available currently to foreign customers. The US isn't far behind with the New York Stock Exchange and NASDAQ readying their tokenized platforms, qualified investors can already access other tokenized assets such as money market funds, private funds and commodities like gold. Also, I want to point out that Securitize, which is a publicly traded company that is partnered with BlackRock, Apollo, KKR and many others that profits from this tokenized Trend. They tokenized 16 billion of assets in 2025 alone. And also I want to mention that tokenized real estate is also going mainstream with continued adoption over the next few years expected first expect that growth to come from under $300 billion to $3 trillion in tokenized real estate by 2035.

[B]

Yeah, my call out here on this one, Robert, is that Securitize? I know there's SPAC right now and the ticker is very volatile. Be careful. This is not an investment recommendation, but I think people have made the mistake of only associating tokenization with crypto and oh, I have to go use or buy Ondo or whatever these like cryptocurrencies are to profit from tokenization when in actuality there's a real company called Securitize that is going to SPAC on the stock market here pretty soon also projecting to have $9 billion of securitized tokenization of assets just through them here in 2026 and then revenue of 110 billion in 2026. So like this is a real company. Hear about the tokenization and all this stuff that's going on. Like, cept I already have, you know, a couple shares here in the 1112 range. Right now it's like 1095, whatever. But if you believe like Robert and I do in the long term of this tokenization stuff, they could be a very clear winner in the space.

[A]

Yeah, my main takeaway with tokenization is I believe as more and more asset classes get put on blockchain rails and they become tokenized, it's going to make things quicker, more effective, better cost structures because it's going to be cheaper to process these items and it's going to make it better for the everyday investor who wants to invest in bigger projects but can only do it with smaller amounts of money. So tokenization is a long way off. I love the call out and I think long term it's going to be great, especially for real estate stocks and maybe some fine art and some of these other asset classes.

[B]

Very cool. So let's now jump to my radar points, Robert. I've got Oracle laying off a ton of people, unfortunately. Google unveiling their Gamma version 4 open source model. We'll talk a bit about that. And then now, of course we alluded to it before. The longest bond market drawdown on record, 68 months. Let's now jump to that first headline about Oracle. The cloud computing and database company is cutting jobs across all of their business lines. Full scope of the layoffs aren't yet clear, but some employees said that those internal metrics are showing a count of reduction in the thousands. An analyst at TD Cohen earlier this year predicted that Oracle would shed as many as 30,000 jobs and even have to sell some of their assets as they try and finance this AI infrastructure project. Oracle's project with OpenAI, known as Stargate, calls for several data centers in the next few years. Investors and analysts also consider the deal to be very risky because again, Oracle is taking on tens of billions of dollars in debt and they've partnered with this unprofitable AI company called OpenAI. Maybe analysts and investors get a little bit more excited about the partnership now because OpenAI has raised 122 billion and will potentially IPO. But regardless, Oracle is really doubling down on this AI infrastructure and it's sad to see that another big company is laying off workers because of AI. Now something not sad is Google unveiling their gamma version 4, which are these sort of open source models. I definitely did not pronounce that correctly, but it's pretty cool Regardless, google wrote in a blog post, these are purpose built for advanced reasoning and agentic workflows, delivering unprecedented levels of intelligence per parameter. This breakthrough builds on incredible community momentum. Since the launch of our our first generation, developers have downloaded Gamma over 400 million times, building a vibrant Gamma verse of 4th and 100,000 variants. Keep the Gamma verse melted. I don't want any of that verse stuff.

[A]

Metaverse GEMA Verse where are we going here? Where are we going?

[B]

That's so 2021. But Google says the Gamma 4 model family can handle complex logic and agentic workflows with the largest models such as the 31B model currently ranking as the number three open model in the world. So if you're looking for an open sour model to run on your Mac studio, maybe Gamut four is a good way to think about it. And finally, this headline I think is really important because it ties into our conversation with our former hedge fund manager. Coming up shortly is the Longest Bond Market Drawdown on Record the bond market has now been in a drawdown for 68 months as of March 2026, by far the longest in history. The Milestone puts the post2020 bond bear market in a category all of its own. As a sign of structural repricing, the Bloomberg US Aggregate Bond Index drawdown started in August of 2020 and has persisted much longer than any previous fixed income slump. Historically burning out within a year or so. Bonds absorbed the initial blow from the pandemic induced inflation shock. Then they of course had to weather the Federal Reserve's fastest tightening cycle in decades. But now they're facing markets that keep questioning how low rates can actually go in the future, as this war with Iran sends energy costs surging. We all know higher energy costs, higher inflation. Fed's not going to cut rates if inflation is sticky. The question for the bond market and its investors is whether that sticky inflation is around and the new oil shock keep the post 2020 drawdown alive even longer. If you want to keep an eye on this one, go type in agg on your platform. That's the iShares Core US Aggregate Bond ETF. You click the five year chart on that. Not good, not good.

[A]

My biggest takeaway, and I love your points today, is that oracle laying off 30,000 workers and I did some research and it says they laid off 30,000 of 162,000 workers. So that's not just a small percentage. That is a large chunk of their workforce. And it just goes to show you, AI is here to stay. It is real, it is efficient, and people need to get ahead of it.

[B]

All right, Robert, let's now jump to our conversation with a former hedge fund manager. Today we are joined by Ron Santella, founder and CEO and CIO of Equable Shares. Ron brings over 40 years of experience managing equity options and volatility strategies, something very important right now across any and every type of market cycle. He began his career in 1985 at O' Connor Associates as a list options trader before going on to serve as head trader and portfolio manager for arbitrage strategies at Grace brothers.

[A]

And in 1990, he founded SAM Investments, a hedge fund focused on convertible bond and volatility arbitrage strategies, and spent the next 15 years managing a series of hedge funds throughout different market environments. He later launched a family office to invest his own capital alongside a select group of partners, refining his approach to alternative strategies and risk management. And in 2008, Ron stepped in as CEO of Fox River Execution, an institutional brokerage firm where he rapidly grew the business before leading it to a successful sale to SunGuard in 2010. Today, through equitable Shares, he's focused on building strategies designed to help investors stay invested while managing downside risk, positioning his approach as an alternative to reactive knee jerk reactions that we talk about all the time. So, Ron, welcome to the Rich Habits podcast. For the very first time. We're excited to have you and chop up what's going on, what should our listeners be thinking about and what's next in the markets?

[C]

Appreciate you and Austin having me today. I'm very excited to be here from Naples, Florida. And as you said, there's a lot going on in the market. So ready to jump right into it?

[B]

Let's jump right in. We're seeing a lot of mixed signals right now between sticky inflation, uncertain rate cut expectations, geopolitical tensions, everything moving up, down, left, right and in circles. Personally, as someone with 40 years of experience in these markets, how are you thinking about positioning in this type of environment?

[C]

As I was listening to my history that you and you and Robert read over 40 years, one thing really hit me that we're in a much more new sensitive environment than we've ever been before. You know, for those of us been doing this for decades, we didn't have these social media real time news all the time. And so we get headlines and the market reacts pretty quick. Quick when you step back from it, you know, the S and P is still only down about 4% for the year. So just in terms of the broader market, it has not really been a catastrophe. With that said, as, as you rightly point out, between what's going on in the Middle east right now, bonds have ticked up to 10 years, up 30 or 40 basis point this year. There's little angst in the market right now. And I think people are sort of searching for a way to navigate that volatility and still stay invested, which is one of the things that we provide a solution solution for. One of the lessons I learned going through market cycles going back to the 87 crash is that it's very hard to time markets. Even for those that are right and know which sectors invest in or what stocks, picking the right time to enter or exit can be pretty tricky. And so one of our fundamental principles is to create a product, which I think we did successfully hedge, that's not really a market timer. So whether the market's going up, whether the market's going down, whether volatility is increasing or decreasing, we believe this product is a solution for any type of environment. And I think that's the key. I think for those who want to stay invested, you want to keep your money in the market, you don't want to pull it out. And so you need that balanced portfolio to give you that kind of conviction to stay invested. And that's where I think we provide a solution.

[B]

Yeah, I think something that Robert and I talk about a ton on, on the show and everywhere else, of course, is time in the market beats timing the market. And a lot of people make that mistake of saying, I can jump in, I can jump out. I know exactly when to sell, when to buy, and nine times out of 10, they're doing it wrong. I think there's a stat out there too that says if you miss the best, like 10 days in the stock market over the last decade, you would underperform dramatically. But no one knows when those best 10 days are. I think we just had the best day of the year recently. I think was a 2.9 day in the NASDAQ or something just earlier this week. Right. A lot of people might have been on the sidelines for that. Well, you mentioned, you mentioned your product hedge. I think it's, it's a really awesome product. But why not take maybe a moment here to explain to our audience what is the H E D G ETF and how does it allow investors to stay invested during times of volatility.

[C]

You know, a hedge is aligned with the name of our company. Our company is equitable shares. And, and if you pull out your old Webster's dictionary, you just want to go Google equable, you're going to see what it means. It means come it means keeping things steady. That same principle just sort of is underpins what hedges H E D G. You know, it's an ETF listed on New York Stock Exchange. On the long side we're exposed the S&P 500. We're long two ETFs, Spy and IVV. It's a pure play in the market. And I, I think in the current environment it's kind of important to recognize we're having record levels of dispersion right now. If you look at the numbers through Q1, if, if you happen to be in energy you might be up 30% or more. If you happen to be in financials you might be down 8 or 10%. Right. We're that solution right in the middle for those who want exposure right to the S&P 500. We then overlay an option hedge on on it. So we're selling call options every 90 days that are struck at the money. One important footnote to that is we do manage the portfolio in a rules based fashion. You're not going to be surprised by our outcome, sort of a defined outcome strategy, quarter to quarter. And then the last piece of the portfolio is we layer in a put spread and out of the money put spread for additional protection. We look at that as like an insurance policy for those dramatic moves that we might get into a quarter if

[B]

it comes down, you got that put option spread. That's going to to your point Ron, act as a little bit of insurance to keep keep your equity up versus having a crazy whipsaw effect in your portfolio. Over to you, Robert.

[A]

Yeah. I want to ask, you know, you've been doing this a long time. I've been at this a long time. How do you typically approach times like this in the market? Like is there a specific time you can remember from a war in the past or anything that reminds you of the current market conditions or is this one completely unique because we have AI and all of this new technology that's changing the course of how people invest their money?

[C]

A very interesting question. Right. We can spend a lot of time with that. And you're right Robert. When we've been doing this as long as you have and I know Austin, you're a student of the financial Markets. When I look back, I think every situation seems unique, whether it's a 87 or 98, you know, Russian default and long term capital management tech bubble crash in the early 2000s to me was a very big event in my life when I was running a hedge fund. When I look at the current environment, it's a single issue market. Right now the market for the most part is reacting to what's going on on in the Middle East. And so if I just look at recent history, it's pretty similar. If we just roll back to last year at the same time, a little bit of deja vu. If you go back to Q1 of 25, the single issue at that point were the tariffs. Incidentally, the market, The S&P 500 was down about 4% in that quarter. Market down about 4% Q1 of this year. We also, we were down less than 1% in both periods, which again that we try provides. So I guess in terms of single issues, that's how I relate. If you look at how wars have impacted the market, you'd go back to 9, 11, which I think would be one of the most dramatic. Right when the market reopened after four days, I think we'd won the biggest single drawdowns on a single day. And then certainly when you fast forward to early 2022, the Russian invasion of Ukraine was another catalyst for getting the market or certainly increasing market volatility that time. And then of course 22, until the Fed started hiking rates and that turned into the worst year since 2008.

[B]

So as it relates to maybe mistakes people make during times of volatility, you just kind of, you know, walked us through a couple of them. What have you learned over time as an investor? What mistakes do you now avoid that you see other investors making during times of volatility? If it's an overreaction to a headline or maybe it's, you know, Austin, I

[C]

think every investor should start with a plan. It might not be a fully vetted plan, but I think you need a plan to get started. I'm personally a fan of having an allocation strategy that includes some risk capital where you might invest in some private deals that's become easier to access these days. Perhaps you get into the public markets in higher growth and then you have a more defensive part of your portfolio. When you have a plan and you have conviction in that plan, it allows one to navigate the rocky periods because they do have conviction in the plan. I think for those that don't start with a plan, that's quote A mistake. I think the second thing, which I think is just human nature is emotions drive the market markets. And when you get, particularly when you get knee jerk or quick reactions in the market, people tend to respond with emotions. The old cliche, greed and fear, I've learned over my investment experience, particularly running a hedge fund when we were in the absolute return business, is that you had to really extricate emotion from the decision process. So I guess they would be the two biggest lessons for me. Have a plan and eliminate emotion when you're making decisions.

[A]

One of the things relative to a personal finance plan is I don't think 90% of the people out there, if you say what is your personal risk tolerance strategy? I don't think they know. They all just want to get rich, but they don't have a real plan. And that's the most important thing for me is trying to define, and I love that you talked on that. What is your risk tolerance for you, not what the world says it should be. And what is your plan can. Because if you can define those two things, I feel like you can take a lot of the emotion out of this. And trust me, Ron, I. In Austin we are talking people off the ledge daily in these volatile markets and I'm sure you are as well. And it's frustrating because if we can get people to build that muscle and set aside the emotion, they end up performing so much better because they're not in and out constantly trying to time things things because of their fear related to the headlines. So with markets still at near all time highs, but risks are clearly elevated, how do you feel personally investors should think about protecting on the downside without fully stepping out of equities and sitting in cash.

[C]

It's okay. I'm going to start with the second question. The classic 60 40, sort of a metaphor for just having a balanced approach to investing. You want a long growth strategy in equities and you want a little bit less volatility in income by having exposure to fixed income or something like fixed income. I think for a long time that worked. You could just throw it in there. I think 22 was the wake up call, particularly when you add the longer dated bonds pulling back dramatically. And so that would be the biggest example, I think Austin for our strategy which was down 6% that year versus about an 18% drawdown, S& P where we just totally outperformed the 6040 index, that some 6040 indices were actually down 25% that year. And so I think that gets back to what Robert just Said an investor has to know what they have. They know where the risk in their portfolio lies. Personally, I think one of the bigger risk that does not get talked about is liquidity risk. And I think right now the current environment, private credit is shining a light on that because I don't think private credit has a credit issue right now. At least I think it has liquidity issue. And so that's another part of hedge that's important.

[A]

It's.

[C]

We put in an ETF wrapper for a reason. It's a liquid wrapper for investors. Our underlying securities are some of the most liquid ETFs on the market. That's a risk reduction tool. I think when one invests, they should really try not to step out of that corner. Equities. Getting back to one of your initial comments about not trying to time the market is really important. And so to me, an investor should have their money in growth areas of the market and benefit from positive moves in the market. But it gets back to having some insurance in your portfolio. So when I look at hedge, there were three consecutive years, 23, 24, 25, where the market was up double digits, hedge was up double digits every one of those years. Not as strong as the market, but there's still upside participation. But I think when one looks at the down period periods and whether it was Q1 of last year, Q1 of this year, Q3 of 23, you're going to see that we're down less than 1% for a period when the market's down almost 12%. And I think when you have a part of your portfolio that's actually performing well, it gives you the confidence to maintain the other portion of your portfolio and ride out some of those rocky periods.

[B]

I like that. Right. It comes down to portfolio construction because we talk about this all the time on the show where we believe in the core satellite portfolio strategy. 65 to 85% of someone's portfolio should be invested in long. And the index funds and ETFs we talk about like the S&P 500, the NASDAQ, the Dow Jones and then that call it 15 to 35% could be diversified into other maybe non correlated asset classes. We talk about real estate, we talk about fine artwork, we talk about the private stuff that you were alluding to. And now as people think about that true portfolio composition, maybe some of that diversification should be inside of your ETF hedge.

[C]

We don't think that's appropriate to try and time a hedge. I equate it to if you Own a car, you're going to have car insurance. You probably don't think about it too often. You just pull it out when you need it. I don't think it's any different having a hedge in your portfolio. I think you want it there. You may not think about it a lot when you need it, you're going to be glad you have it. At the core. There just needs to be a rational and reasonable portfolio construction plan. And whether the market's down or up, we don't differentiate. We think hedge belongs in a portfolio no matter what the market condition is.

[B]

Well, I think you were just alluding to something very interesting which is like we don't try and time the hedge. And when people think about hedging their portfolio, those theoretically what they're essentially asking themselves in their mind is like, do I sell my equities and sit in cash? Right. It's like a black and white where I look at hedge your ETF as sort of the in the middle gray area. You can still be long while also having some downside protection.

[C]

The bottom line is when you look at our portfolio, Austin, it's a combination of market participation on the way up, hence the double digit returns that we've had in 23, 24, 25 and down more markets you're going to see, at least historically, very good protection on the way down and also low volatility. Volatility of hedge is much closer to fixed income, yet the returns have been much greater, at least for the last three or four years.

[A]

Ron, what an incredible conversation. I love having you on the show chopping it up, talking about what's happening because you know, kind of the old joke from our earlier days in these markets was is the best performing portfolios are those from people that lost their password, were and dead people because they don't overreact. They don't have these knee jerk reactions that Austin and I talk about every single day. And I think what you've built really helps them tactically prevent themselves because you're giving them hedge, you're giving them this hedge in their portfolios. I think it's a really, really smart play of what you built here. And we appreciate you coming on the show.

[C]

Great conversation. Look forward to the next one.

[B]

Robert, 10 out of 10 conversation with Ron. I think it's never been more important for people listening to the show to have diversification. We talk about about it till we're blue in the face. We talk about the portfolio strategy, how you should be diversified into real estate, into precious metals. Into venture into insert other fine artwork, have some a slice of the portfolio into some of these hedged products. So when times are good they're doing just fine but when times are bad they are holding up and hedging your portfolio. Massive. Shout out to Ron for joining us on the show. I've had hedge in my own portfolio for a while while please consider checking it out. We think it's an incredible product. It's going to do awesome stuff for everyone especially as we navigate the volatility that is the mid term election year 2026.

[A]

Yeah, it was a great conversation. I love episodes like this because we're very specific on the types of guests we bring onto the show and Ron did a really good job and I really like hearing it for other legends in the space that have been doing it for decades because because they've wavered all the storms like I have, they've been through all the dot com booms and busts and all that. So we have a really good take on how to USA and step back from the ledge and not have those knee jerk reactions we talk about all the time. So what a great episode. Such a good interview. Take some notes. Ron had some really good nuggets in there. But as always we appreciate each and every one of you, thousands of you, you stopping by every single week for these new Friday episodes.

[B]

And do not forget the Rich Habits Retreat. We have literally, I think six tickets left and their only general admission. Everything else is sold out. Like we are down to the last six here. Only GA tickets remaining. If you're interested in joining us on May 1st and 2nd in Austin, Texas at the Rich Habits Retreat, all about venture capital investment dusting. Our friend Chris Camillo is going to be there. Zaded Moni from the Rundown is going to be there. It's going to be fun. We're going to have a blast. If you're interested in learning more about, there's a link in the show notes below. Thanks everyone for tuning into this week's episode of the Rich Habits Radar and we'll see you on Monday.

[C]

The wrongs we must right. The fights we must win. The future we must secure together for our nation. This is what's in front of us. This determines what's next for all of us.

[B]

We are Marines.

[C]

We were made for this.