In this episode of In the Money with Amber Kanwar, investor Daniel Lewis, founder of Orange Capital, reflects on his journey from billion-dollar hedge fund manager to nimble, independent investor building a concentrated portfolio of distressed bets and ‘orphaned’ stocks everyone else is missing. 

Lewis shares how he built his reputation by diving headfirst into some of the most controversial and underfollowed stock stories. From friendly activism to quiet turnarounds, he pulls back the curtain on what it really takes to invest in special situations — and why Canada’s governance quirks make it a “wild west” of opportunity.

He talks candidly about failed bets like Bellatrix and fund burnout, and why that chapter led to richer, more rewarding investing today. He also warns of the "melting ice cube" effect on legacy businesses that fail to evolve with AI, and argues that investors are dramatically underestimating the risk of obsolescence.

Daniel shares three of his latest distressed bets, each with major upside potential — and yes, real risk. He walks through the deep value case for Claros Mortgage Trust (CMTG), a mortgage REIT trading at a fraction of book value; explains why Hippo (HIPO) is more than just an insuretech story and could re-rate as a high-margin fee-based business; and makes the bold bull case for Better Home & Finance (BETR), calling it a true AI-native company hiding in plain sight. With echoes of Carvana and a wild ride of its own, Better could be a 30-50x return — or go to zero.

Timestamps

01:55 Daniel’s investing style and why he thinks Canada is ripe with opportunities
03:30 Daniel on ‘friendly’ activism and why it can be incredibly rewarding 

05:30 Why Daniel talks about this mistakes and what he’s learned over the years 

10:15 Daniel’s involvement in Canada right now
12:45 Daniel on why distressed investing is still relevant
16:15 Why you need to have a high risk appetite for this type of investing but there is the possibility of major upside
20:10: Daniel on distress in large cap stocks
23:00 How to spot the winners and losers and the risk of obsolescence
28:40 Daniel on being opportunistic and why he picked up down and out SPACs
32:00 Daniel’s Pro Picks 

Sponsors

This episode is sponsored by BMO InvestorLine. We all want to make the most of our investments. That’s why BMO InvestorLine is here. Start investing today with BMO InvestorLine. https://wealth.bmo.com/wealth/onboard/onlineinvesting/#/set-expectation?lang=en&ecid=pr-2886232INV1-JNBMO20

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. 

Links
https://inthemoneypod.com/ 

https://instagram.com/inthemoneypod

https://facebook.com/profile.php?id=61569721774740 

https://twitter.com/inthemoneypod 

https://tiktok.com/@inthemoneypod

[email protected]

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.

BMO DISCLAIMER 

Terms and conditions apply. BMO InvestorLine is a wholly owned subsidiary of Bank of Montreal. Member – Canadian Investor Protection Fund and Member of the Canadian Investment Regulatory Organization.

The opinions and views expressed in this presentation are those of the presenter and not necessarily BMO InvestorLine Inc. This presentation is prepared as a general source of information and is not intended to provide legal, investment, accounting or tax advice, and should not be relied upon in that regard. If legal or investment advice or other professional assistance is needed, the services of a competent professional should be obtained. Any information contained in this presentation does not constitute and shall not be deemed to constitute advice, an offer to sell/purchase or as an invitation or solicitation to do so for any entity. The content of this presentation is based on sources believed to be reliable, but its accuracy cannot be guaranteed. BMO InvestorLine Inc. and its affiliates, sponsors and employees do not accept responsibility for the content and makes no representation as to the accuracy, completeness or reliability of the content and hereby disclaims any liability with regards to the same.

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.

Contact: [email protected]

#IntheMoney #Investing #StockMarket #CanadianInvesting #FinancialNews