In the Money with Amber Kanwar Downtown Josh Brown: Stay Invested and Shut the F**k Up
Wall Street meets real talk in this week’s In the Money with Amber Kanwar, featuring none other than Downtown Josh Brown — the CEO of Ritholtz Wealth Management, CNBC regular, and host of the hit podcast The Compound and Friends. From surviving the chaos of the 2008 financial crisis to building a wealth management firm with billions under management, Josh shares how storytelling, not spreadsheets, shaped his investing journey.
Amber and Josh dig into today’s market vibes — from AI-fueled rallies to why valuations “don’t have to rhyme with 2000.” Josh tells us how he thinks about managing risk, and what he really thinks about gold, tariffs, and America’s new brand of “mercantilism.” Importantly he tells our listeners to stay invested, diversify and offers his most important rule: shut the f**k up!
In Pro Picks, Josh opens up his own portfolio and explains why his biggest bet is on Uber (UBER) — the “cheapest large-cap tech stock,” and his play on the future of autonomous delivery and driverless mobility. He’s also adding to Amazon (AMZN), confident that its partnership with Anthropic and growing cloud presence will make it a bigger AI winner than investors realize. Then there’s Rocket Companies (RKT), which he calls a top way to play a housing rebound and the refi boom he expects once rates fall. And finally, Toast (TOST) — his pick for the restaurant tech revolution, building a sticky ecosystem from payments to payroll that could make it the “Amazon of hospitality.”
Timestamps
00:00 Show intro
02:00 Downtown Josh Brown tells us how he he fell in love with the stock market
05:30 Why Josh started the blog The Reformed Broker, and how it changed his life
08:30 It’s hard to remind yourself that history doesn’t repeat
10:30 Is Josh worried right now?
13:00 Where does the market go from here? The mean reversion you’re waiting for isn’t going to happen
17:00 Stay invested, respect trend and shut the f**k up
20:40 Why Josh & Ritholtz make tailored, bespoke portfolios for clients
23:40 What is the gold rally telling Josh?
33:15 Cross-Border investing with Raymond James
35:35 What does Josh think about Canada? He loves it
37:55 Why Josh thinks the most dangerous place to be is a shareholder in the biggest company in Canada
40:05 Risk is to the upside when it comes to tariffs
42:10 Josh says Trump is not a capitalist, he’s a mercantilist
45:15 Josh’s Pro Picks (UBER, AMZN, RKT, TOST)
Sponsors
For over 25 years, Raymond James has been helping Canadians achieve their financial goals. Visit https://raymondjames.ca today to discover how you can live a life well planned.
Pro Picks is brought to you by ATB Financial. Visit https://ATB.com/inthemoney for more information
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DISCLAIMERS
The information provided in this podcast is for informational purposes only and does not constitute financial, investment, or professional advice.The views expressed by the host and guests are their own and do not necessarily reflect the opinions of any organization or company. The host and guests may maintain positions in any securities discussed on the podcast. Always consult with a qualified financial advisor or professional before making any investment decisions.
Raymond James Ltd. is regulated by the Canadian Investment Regulatory Organization ("CIRO") and is a Member of the Canadian Investor Protection Fund.
In the Money delivers expert stock picks, market analysis, and timely investing insights. Hosted by business journalist Amber Kanwar, each episode features interviews with top portfolio managers and financial experts. Covering everything from ETFs and Canadian stocks to global investing trends, dividend strategies, and risk management, this show is made for DIY investors, stock market enthusiasts, and anyone looking to sharpen their financial strategy.
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