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.
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In the Money delivers expert stock picks, market analysis, and
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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
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