424 episodes

Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com

Invest Like the Best with Patrick O'Shaughnessy Colossus

    • Business
    • 4.6 • 13 Ratings

Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com

    Michael Simanovsky - A Platform Approach to Real Estate

    Michael Simanovsky - A Platform Approach to Real Estate

    My guest today is Michael Simanovsky. Mike is the Managing Partner of Conversant Capital, a real estate investment firm he founded in early 2020. Conversant aims to be the most flexible capital provider in real estate, investing across public and private markets as well as equities and credit. The firm will also incubate platforms where they see an opportunity to take advantage of a compelling theme that lacks existing business models for investment. We cover the most undersupplied part of the market, why he’s building Conversant to be so flexible, and the surprising appeal of billboards. Please enjoy my conversation with Mike Simanovsky.

    Listen to Founders Podcast

    Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19.

    For the full show notes, transcript, and links to mentioned content, check out the episode page here.

    -----

    This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick.

    -----

    Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

    Follow us on Twitter: @patrick_oshag | @JoinColossus

    Show Notes
    (00:03:32) (First question) - Real estate investing through the lens of the capital cycle
    (00:06:50) - The capital cycle in practice
    (00:12:07) - Using evaluation of supply to determine where you are in a capital cycle
    (00:13:16) - Why real estate drew Mike in 
    (00:15:35) - The quality of investors in real estate
    (00:16:41) - What the US market needs most
    (00:20:26) - The range of returns in real estate
    (00:23:01) - Insights that stand out
    (00:26:45) - Starting a new company vs. building a portfolio of assets
    (00:28:46) - Key trade-offs and choices when building a firm
    (00:31:10) - Where things go wrong
    (00:33:59) - Best investment decision he ever made
    (00:38:06) - Philosophy on CapEx
    (00:39:52) - Misconceptions about real estate investing 
    (00:41:31) - Cold storage real estate
    (00:43:13) - The most interesting corners of the real estate market
    (00:46:13) - AI and its impact on the future
    (00:48:30) - Common investor missteps 
    (00:50:51) - Three guests Mike would invite to a dinner party 
    (00:52:34) - The most impactful questions to ask a real estate investor
    (00:53:17) - A defining moment of his career
    (00:53:17) - The premise of the platform approach
    (00:56:20) - Possible opportunities and an understanding of the current landscape
    (01:03:38) - Lessons Mike learned from basketball coach John Wooden’s philosophies 
    (01:04:30) - The kindest thing anyone has ever done for him

    • 1 hr 6 min
    David Senra - In Service of Founders

    David Senra - In Service of Founders

    My guest today is David Senra, the creator and host of Founders Podcast. With an incredible appetite for biographies, David has delved into the lives of over three hundred entrepreneurs, extracting invaluable wisdom that he shares with his audience each week. Throughout the conversation, we discuss David’s love of podcasts, and what can be gained from studying the lives of not just entrepreneurs, but of athletes and film directors alike. I hope you enjoy this conversation with David Senra.

    Listen to Founders Podcast

    Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19.

    Our first interview with David, Episode 292: Passion & Pain

    For the full show notes, transcript, and links to mentioned content, check out the episode page here.

    -----

    This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick.

    -----

    Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

    Follow us on Twitter: @patrick_oshag | @JoinColossus

    Show Notes
    (00:02:43) - (First question) - David's journey so far
    (00:05:13) - Why there are no negative surprises linked to his work
    (00:07:13) - Being bullish on podcasts
    (00:13:27) - The importance of storytelling to the entrepreneurial journey 
    (00:17:43) - The impulse of entrepreneurs who are world-builders 
    (00:23:03) - The universal trait of successful entrepreneurs 
    (00:27:43) - What David has learned from filmmakers 
    (00:31:23) - The dark side of the Type-A personality
    (00:35:13) - What he has learned from athletes
    (00:42:27) - The effects of early childhood on success
    (00:43:48) - Insights gained from conquerors 
    (00:49:33) - Ranking the importance he places on power, wealth, and fame
    (00:56:13) - The possibility of episodes on spiritual figures
    (01:02:17) - How Henry Ford created something bigger than himself
    (01:05:43) - His thoughts on ‘high agency’ people
    (01:11:57) - Why David is not afraid to talk about anything publicly
    (01:16:27) - His favorite line from Game of Thrones

    • 1 hr 24 min
    Will England - A Primer on Multi-Strategy Hedge Funds

    Will England - A Primer on Multi-Strategy Hedge Funds

    My guest today is Will England, the CEO and Co-CIO of Walleye Capital. Walleye is a multi-strategy hedge fund headquartered in Minnesota that manages around $5 billion. Our conversation is a primer on multi-strategy hedge funds, which have become a force in markets through the success of firms like Millenium, Citadel, Point72, and Balyasny. We discuss the operational complexity behind the model, which managers best fit this type of investment style, and what happens in stress events like the Gamestop short squeeze in early 2021. We also talk about performance culture, the All Blacks, and Will’s experience as a US National Team rower. Please enjoy my conversation with Will England.

    Listen to Founders Podcast
    Founders Episode 311: James Cameron

    For the full show notes, transcript, and links to mentioned content, check out the episode page here.

    -----

    This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick.

    -----

    Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

    Follow us on Twitter: @patrick_oshag | @JoinColossus

    Show Notes
    (00:03:22) - (First question) - His fascination with Robber Barons
    (00:04:49) - He explains the style of investing he has built at Walleye Capital   
    (00:08:51) - The importance of scale and what it means for firms like this 
    (00:13:01) - A breakdown of the component parts of a 15% return structure
    (00:16:56) - His advice to new portfolio managers trying to succeed with long/short investments
    (00:21:23) - His reaction to an efficient market hypothesis   
    (00:27:33) - He tells us what happens above the individual manager level
    (00:29:42) - The universe of talented people behind the business
    (00:35:26) - The backstory of Walleye Capital and why he chose Minnesota    
    (00:42:37) - He discusses the felt experience of being at Walleye versus other firms 
    (00:47:25) - Whether he identifies more as an entrepreneur systems builder or as an investor
    (00:50:04) - What he says about the half life of successful quantitative strategies  
    (00:54:03) - A breakdown of style allocations and the percentage of managers within each 
    (00:56:30) - How he determines how much leverage to use and how to be great at applying it 
    (00:59:59) - How the firm handles tough investment periods
    (01:02:34) - How he knew Citadel wasn’t taking down gross during the GameStop short
    (01:03:51) - What he looks for when hiring a portfolio manager
    (01:06:37) - His philosophy on performance and how he blends that into his firms culture 
    (01:09:21) - Inspiration he’s taken from the All Blacks team
    (01:11:25) - Addition aspects of the firm he believes are important
    (01:13:46) - Historical finance pioneers that inspire him 
    (01:16:07) - The kindest thing anyone has ever done for him

    • 1 hr 19 min
    James Cameron: The Futurist

    James Cameron: The Futurist

    Almost exactly a year ago, Colossus entered into a partnership with David Senra and the Founders podcast to join the Colossus network. The show has since exploded with more devoted fans than any podcast that I've encountered. With that in mind, we are excited to share an example episode from his show here today on the director, James Cameron. It's my favorite recent episode of David's. Please enjoy this episode, and if you haven't already, subscribe to Founders.

    This is what he learned from reading The Futurist: The Life and Films of James Cameron by Rebecca Keegan and The Return of James Cameron, Box Office King by Zach Baron.

    Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19.

    For the full show notes, transcript, and links to mentioned content, check out the episode page here.

    -----

    This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick.

    -----

    Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

    Follow us on Twitter: @patrick_oshag | @JoinColossus

    Show Notes
    (00:04:00) - I watched Titanic at the Titanic. And he actually replied: Yeah, but I madeTitanic at the Titanic.
    (00:07:10) - I like difficult. I’m attracted by difficult. Difficult is a fucking magnet for me. I go straight to difficult. And I think it probably goes back to this idea that there are lots of smart, really gifted, really talented filmmakers out there that just can’t do the difficult stuff. So that gives me a tactical edge to do something nobody else has ever seen, because the really gifted people don’t fucking want to do it.
    (00:07:20) - At 68 years old, Cameron wakes up at 4:45 AM and often kick boxes in the morning.
    (00:07:45) - Self-doubt is not something Cameron has a lot of experience with. His confidence preceded his achievements.
    (00:09:00) - I basically gave myself a college education in visual effects and cinematography while I was driving a truck.
    (00:16:00) - Every idea is a work in progress.
    (00:17:30) - He's been on a planet of his own making ever since.
    (00:18:00) - The Return of James Cameron, Box Office King by Zach Baron
    (00:22:00) - His outlook is that we can take fate in our own hands.
    (00:34:00) - Cameron had only been at Corman's for a matter of days, but he was already taking charge. He seems constitutionally incapable of doing otherwise. (What a line!)
    (00:35:30) - Your mediocrity is my opportunity.
    (00:37:40) - Cameron finds writing torture. He does it anyway.
    (00:43:00) - Cameron is willing to let ideas marinate for decades.
    (00:55:30) - I'd just made T2 for Carolco and I admired how they rolled, being their own bosses, mavericks, entrepreneurs.
    (00:57:30) - Mute the world. Build your own world.
    (01:04:50) - Opportunity is a strange beast. It commonly appears after a loss.

    Buy a book: All the books featured on Founders Podcast.

    • 1 hr 13 min
    Lee Ainslie - Hedge Fund Maverick

    Lee Ainslie - Hedge Fund Maverick

    My guest today is Lee Ainslie, the founder of Maverick Capital. Lee started his investing career at Tiger Management where he worked for Julian Robertson. In 1993, he left to start Maverick and has built the firm into one of the top-performing hedge funds of the last 30 years. Lee doesn’t speak in public often so this is a fascinating insight into what it takes to build an enduring investment business - both psychologically and operationally. Throughout the conversation, we flick between his lessons building Maverick, his perspective on the market, and what he’s learned about the craft of investing. I hope you enjoy this great conversation with Lee Ainslie.

    Listen to Founders Podcast
    Founders Episode 311: James Cameron

    Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19.

    For the full show notes, transcript, and links to mentioned content, check out the episode page here.

    -----

    This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick.

    -----

    Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

    Follow us on Twitter: @patrick_oshag | @JoinColossus

    Show Notes
    (00:03:00) - (First question) - Lee tells us about his relationship with Steve Mandel
    (00:04:29) - Why he thinks Steve gave him a hand into the role he excelled at
    (00:07:22) - The concept behind investment talent
    (00:13:08) - Steps he takes to hire the right individuals for his team
    (00:16:14) - Why he stepped out on his own to start Maverick Capital
    (00:20:48) - What he thinks makes for a great investment or stock purchase
    (00:25:16) - How Maverick maintains its edge over other comparable firms
    (00:28:31) - Features of a business that get his attention in a unique way
    (00:32:03) - What he learned from Sol Price
    (00:38:21) - The difficult aspects of portfolio construction
    (00:42:04) - How zero interest rates affected the long short style of investing
    (00:47:22) - Positioning his team for success against other competitors 
    (00:50:32) - How private market activity can affect public market activity 
    (00:54:27) - Software companies and their strengths and weaknesses in the investment market
    (00:59:33) - Things he tells his team to watch for
    (01:04:10) - What Lee's learned about money
    (01:07:02) - The most important conversation he’s had in Mavericks history 
    (01:12:38) - Advice for senior executives trying to pass on responsibilities to others
    (01:17:54) - What the next ten years for Maverick Capital look like 
    (01:20:42) - Things Lee and Warren Buffett disagree on
    (01:24:11) - The components of a great investment pitch
    (01:25:08) - The hardest question anyone could ask him
    (01:28:48) - What he thinks is important having started Maverick Ventures 
    (01:31:32) - The kindest thing anyone has ever done for Lee

    • 1 hr 36 min
    Nick Kokonas - Know What You Are Selling

    Nick Kokonas - Know What You Are Selling

    Today, we are running a special episode from our show Founder's Field Guide. In this conversation, Nick Kokonas shares his experience of bringing a business mindset to the restaurant industry. It is one of our favorites at Colossus and there is something for everyone in this timeless conversation. Nick is the co-founder of 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. He majored in philosophy before becoming a derivatives trader and is now one of the most well-known names in the hospitality industry.

    Listen to Founders Podcast
    Founders Episode 311: James Cameron

    For the full show notes, transcript, and links to mentioned content, check out the episode page here.

    -----

    This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick.

    -----

    Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

    Follow us on Twitter: @patrick_oshag | @JoinColossus

    Show Notes
    (3:02) – (First question) – Why he thinks it’s so important to own something
    (4:35) – Make decisions that have outcomes
    (7:00) – His interest in the restaurant business
    (8:54) – Why restaurants are so tough 
    (12:05) – How their business mindset changed their running of the restaurant
    (14:35) – Words they would avoid in the restaurant 
    (16:19) – Asking the right questions in the restaurant business
    (20:40) – Importance in taking the right risks
    (22:02) – Coming up with innovative strategies for ticketing, selling meals ahead of time, and dynamic pricing
    (30:08) – Can dynamic pricing be extended to other businesses
    (31:20) – Origin of Tock
    (36:17) – Early days of Tock and identifying the right customers/challenges
    (41:33) – Importance of the first customer 
    (44:22) – The typical restaurant business model
    (49:23) – Lessons from Tock and the importance of knowing what your selling
    (53:47) – Lessons from publishing
    (55:44) – Other aspects of business that people know but do nothing about 
    (1:00:19) – Their response to Covid and lessons learned
    (1:07:43) – The real impact to the food delivery companies
    (1:09:24) – How businesses communicate their end processes to their customers
    (1:14:07) – Kindest thing anyone has done for him

    • 1 hr 16 min

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