RiskReversal Pod

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Dan Nathan sits down with Paul Costolo, former CEO of Twitter and current VC. They start with Dick's early comedy days (Second City alongside Steve Carell, two SNL auditions that didn't pan out) and his stint writing for HBO's Silicon Valley, before diving into his path from founding FeedBurner to running Twitter through its IPO — including candid stories about the culture shift from private to public company life, and a surreal late-night run-in with Jack Dorsey in Paris in the middle of Elon Musk's takeover drama.

From there they get into Dick's venture firm, 01 Advisors, and his thesis on investing in the AI "enablement layer" (the infrastructure sitting above the models) rather than chasing the flashiest apps. Dick shares his read on today's eye-popping valuations — including Stripe's $7 billion acquisition of OpenRouter and a leaked investor letter claiming "the singularity happened on New Year's Day" — and gives his predictions for the coming wave of AI IPOs, arguing Anthropic and SpaceX are well positioned while OpenAI could face a tougher road given its executive turnover and messaging challenges. They close by talking about prediction markets (and the striking gap between how well people think they're doing on platforms like Kalshi versus reality), before wrapping up with a plug for Dick's own podcast, the Dick and Paul Show.

—FOLLOW USYouTube: @RiskReversalMediaInstagram: @riskreversalmediaTwitter: @RiskReversalLinkedIn: RiskReversal Media

The financial opinions expressed in Risk Reversal content are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on Risk Reversal.

Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in Risk Reversal carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money that you can afford to lose.

Derivatives are not suitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell or retain any specific investment or service.

Dan Nathan hosts FirstMark Capital partner David Waltcher at the firm’s HQ to discuss Waltcher ’s path from an Accel internship to investing in enterprise software, security, and AI. They compare the consumer-to-SaaS shift, the post-2021 “SaaSpocalypse,” and how public markets can overreact to AI narratives, using Salesforce as a system-of-record case study. Waltcher argues many incumbents will prove durable due to switching costs, ecosystems, and trust, while M&A is accelerating amid volatile publics, strong buyers, and fast-growing AI businesses, citing deals like Stripe–OpenRouter and interest in Workday. The conversation turns to Chinese and open models driving token cost deflation and model routing, and to rising security threats, including agent-related incidents, fueling demand. Waltcher highlights FirstMark investments Onyx (agent security), Nebulock (agentic threat hunting), and Tracebit (assume-breach deception), and says innovation risk is highest if recession or a market crash hits, not from AGI timing debates.

—FOLLOW USYouTube: @RiskReversalMediaInstagram: @riskreversalmediaTwitter: @RiskReversalLinkedIn: RiskReversal Media

The financial opinions expressed in Risk Reversal content are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on Risk Reversal.

Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in Risk Reversal carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money that you can afford to lose.

Derivatives are not suitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell or retain any specific investment or service.

Learn more about Astraeus Wealth Management: http://astraeuswealth.com/partner-with-us

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Dan Nathan and Guy Adami are joined by Peter Boockvar, CIO at OnePoint BFG Wealth Partners, to unpack recent inflation data and why yields remain resilient, with the curve steepening as the two-year dips while the 10-year holds around 4.65%. Boockvar argues the Fed must weigh PPI alongside CPI, noting persistent producer pressures and limited pass-through that squeezes margins and hiring, contributing to weak consumer confidence and “running to stand still” wages. They discuss why the S&P 500 continues to levitate, attributing much of earnings and market leadership to massive AI CapEx spending and its spillovers into financials. The conversation previews key retail earnings (Home Depot, Lowe’s, Target, TJ Maxx, Walmart) and highlights strong energy stocks amid high gasoline prices and inventory drawdown risks. They also debate U.S.-China AI competition, pressure on OpenAI/Anthropic business models, and Japan’s yen intervention, rising odds of a BOJ rate hike, and potential repatriation flows.

—FOLLOW USYouTube: @RiskReversalMediaInstagram: @riskreversalmediaTwitter: @RiskReversalLinkedIn: RiskReversal Media

The financial opinions expressed in Risk Reversal content are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on Risk Reversal.

Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in Risk Reversal carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money that you can afford to lose.

Derivatives are not suitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell or retain any specific investment or service.

Checkout the WAWD Substack: https://whatarewedoingonthedesk.substack.com/

Dan Nathan welcomes Vincent Daniel, partner at Seawolf Capital and one of the investors who called the 2008 housing crash, for a deep dive into where markets stand heading into year-end. They break down new Fed chair nominee Kevin Warsh's "immaculate economy" problem, why passive fund flows are quietly the most powerful force in the market, and the hedge-fund blowup that briefly rattled the S&P. From there, Dan and Vincent get into the real meat of the episode: the new wave of GPU-backed financing deals from Nvidia, Apollo, and Blackstone, why Vincent thinks the AI trade is less a Ponzi scheme and more a "debt-infield CapEx initiative," and where the credit risk is really hiding. They also debate capital availability, return on invested capital, which software names survive the AI shakeout, and whether this all ends up looking more like the dot-com bust or the GFC. Plus: an unprompted case for why Vincent should be the next GM of the Mets.

—FOLLOW USYouTube: @RiskReversalMediaInstagram: @riskreversalmediaTwitter: @RiskReversalLinkedIn: RiskReversal Media

The financial opinions expressed in Risk Reversal content are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on Risk Reversal.

Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in Risk Reversal carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money that you can afford to lose.

Derivatives are not suitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell or retain any specific investment or service.

Click the link http://kalshi.com/r/MOSES or download the Kalshi App and use code MOSES to sign up and trade today!

Checkout WAWD on Substack: https://whatarewedoingonthedesk.substack.com/OTT

Sonali joins the podcast on the one-year anniversary of moving from Bloomberg to iCapital, discussing her media series “The Bridge” and iCapital’s reach across wealth and asset managers. The conversation centers on AI economics, especially how declining token costs shift value along the “AI food chain,” with hyperscalers capturing a large share while software and enterprises benefit as costs fall, and with demand (Jevons paradox) potentially sustaining aggregate spend and CapEx. They address rising APAC innovation, why frontier labs pursue IPOs amid heavy cash burn and broad access to debt and equity, and the new NVIDIA-led $500B compute financing platform as Wall Street crowds into AI while investors struggle to diversify as infrastructure, power, and data centers converge. They discuss abundant 2026 liquidity that may tighten, oil’s impact on consumers and second-half caution, hedge fund crowding and the situational awareness leverage unwind, valuation dispersion (semis vs financials/utilities), and rate risks including Treasury basis-trade leverage, a 10-year yield range of 4–4.8%, Japan’s carry trade, and selective interest in Japan and parts of APAC for international exposure.

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ABOUT THE SHOW

For decades, Danny has seen it all on Wall Street and has built his reputation on integrity, curiosity and skepticism that he will bring with him each week. Having traded through the Great Financial Crisis and being featured in "The Big Short" is only part of the experiences Danny wants to share with the listener. This weekly podcast cuts through market noise, offering entertaining and informative discussions with expert guests giving their views of the financial world and the human side of it. Whether you're a seasoned investor or just getting started, On The Tape provides something for all listeners.

Follow Danny on X: @dmoses3

The financial opinions expressed are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on this content.

Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in 'On The Tape' carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money that you can afford to lose.

Derivatives are not suitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell or retain any specific investment or service.