371 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
    • 4.5 • 30 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

    Trina Spear - Billion Dollar Scrubs

    Trina Spear - Billion Dollar Scrubs

    My guest today is Trina Spear, a former investor at Blackstone and the co-founder and CEO of FIGS. FIGS is a multi-billion-dollar public company that built a category-leading brand selling scrubs to healthcare professionals. It was a problem hiding in plain sight and FIGS solved it through vertical integration and customer obsession. Trina shares so many interesting, simple lessons that are often ignored in business. Please enjoy my great conversation with Trina Spear.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
     
    -----
     
    This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 
     
    -----
     
    Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.
     
    -----
     
    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
    [00:02:28] - [First question] - The original insight that lead to founding FIGS
    [00:04:28] - Why obvious opportunities can go so long before being seized 
    [00:06:23] - Key dimensions needed to improve the product and the early days 
    [00:09:02] - Basic overview of a clothing retailer’s financial profile
    [00:10:49] - Financing the business and the early stage cash flow cycle 
    [00:13:04] - Strategies to manage workflow and making sacrifices
    [00:14:43] - Advice for people trying to build their brands in a hands-on way 
    [00:17:14] - The biggest calculated risk she took in the first five years
    [00:19:00] - Building a foundation that allowed for such explosive growth
    [00:21:44] - The story that allowed FIGS to connect with their customers
    [00:24:43] - Painting a picture of the size and scope of healthcare apparel
    [00:26:22] - Things lazy companies do and thoughts on product variety
    [00:28:54] - Defining SKU productivity and what to do with low productivity products 
    [00:30:21] - Chip Wilson Book; Lessons learned from reading Chip’s story
    [00:31:58] - Balancing a healthy relationship with your CFO
    [00:33:59] - Where she sees the most runway to tackle and continue to execute
    [00:35:46] - A women-lead industry and her time spent with Meg Whitman
    [00:38:13] - The most essential jobs she feels she has and shouldn’t do as the CEO
    [00:40:03] - Thoughts about relationships with investors and messaging 
    [00:42:14] - What she’d be most focus on in founders if she was just an investor 
    [00:43:57] - The most stressful thing that has ever come across her desk 
    [00:44:41] - What types of things bring her the most joy in building FIGS
    [00:45:27] - Philosophy of hiring given their small team and when it’s okay to hire
    [00:46:56] - Whether or not there’s a role for non A players in businesses
    [00:47:48] - The kindest thing anyone has ever done for her

    • 49 min
    Gabriel Leydon - How Web3 Onboards a Billion Users - [Web3 Breakdowns, EP.37]

    Gabriel Leydon - How Web3 Onboards a Billion Users - [Web3 Breakdowns, EP.37]

    Today, we are sharing an episode of Web3 Breakdowns with you. My Invest Like the Best conversation with Gabe Leydon last year was one of my favorites and became one of our most popular. Since that conversation, Gabe has become one of the most interesting builders in web3 that I know so I was excited to have him back to share his views of the space and how it might grow. If you enjoy this episode, subscribe to Web3 Breakdowns on your preferred podcast player.
     
    My guest today is Gabe Leydon, who’s episode last year was one of our most popular ever. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I know. He was the co-founder of Machine Zone, which pioneered free-to-play hits like Mobile Strike and Game of War. Over the past year, he has been in stealth mode building a web2 meets web3 video game company called Limit Break, which is founded on a brand new business model that he calls free-to-own. We dive into his vision for the future of gaming, how it could onboard a billion users onto the Ethereum network, and why the LTVs of crypto gamers are so far higher than their web2 counterparts. Please enjoy this conversation with Gabe Leydon.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
     
    -----
     
    This episode is brought to you by Coinbase Prime. Coinbase Prime combines advanced trading, battle-tested custody, financing, and prime services in a single solution. Clients have used our comprehensive investing platform to execute some of the largest trades in the industry because they are the only publicly-traded company with experience trading and custodying crypto assets at scale. Get started with Coinbase Prime today at coinbase.com/prime.
     
    -----
     
    Web3 Breakdowns is a property of Colossus, LLC. For more episodes of Web3 Breakdowns, 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: @Web3Breakdowns | @ericgoldenx | @patrick_oshag 
     
    Show Notes
    [00:02:19] - [First question] - What free-to-own gaming means and why it’s exciting 
    [00:11:40] - Pre-existing behavior that sets up free-to-own for success
    [00:12:32] - The progression from PFP NFTs to clubs and the road ahead
    [00:14:16] - Overview of the business and monetization model for free-to-own games
    [00:17:51] - The story of DigiDaigaku, their mechanics, the drops, and what lead to their creation
    [00:22:14] - Balancing supply and demand in a free-to-own market
    [00:24:35] - Creativity and extensions of the DigiDaigaku NFTs
    [00:26:13] - Tiering, breeding and the role the Genesis series will play in the Digi universe
    [00:27:32] - The level of brand marketing NFTs will unlock for businesses
    [00:29:57] - How free-to-own will be the primary monetization method for brands
    [00:31:21] - A future with a global marketing shift towards digital property and economies
    [00:33:06] - Why most of the winning PFP projects are of unique characters
    [00:35:50] - His Twitter strategy and how he’s created such a fervor around him
    [00:42:40] - What will define the legendary marketers over the coming decade 
    [00:43:06] - Interoperability needed to make real-world NFT uses appealing to consumers 
    [00:44:44] - Whether or not we’ll see more token-gated business in the future 
    [00:45:40] - Stable Diffusion and his impression of the new AI art generating bots
    [00:48:56] - What great distribution looks like in a digitally native world
    [00:50:03] - The emphasis of innovation taking place in the metaverse being a bad thing
    [00:53:24] - Things he most admires in adjacent games and creators in his world
    [00:54:25] - Unique game mechanics that Web3 technology unlocks 
    [00:56:16] - NFTs will be the gateway for people to acquir

    • 59 min
    Harley Finkelstein - Building the Entrepreneurship Company

    Harley Finkelstein - Building the Entrepreneurship Company

    My guest today is Harley Finkelstein. Harley is the President of Shopify and has been with the company since its early years. He is a lawyer by training but an entrepreneur by calling and that is the focus of our discussion. We discuss the different dimensions of entrepreneurship and Shopify’s role in promoting it, as well as exploring the company’s transition to public markets, and what the last few years have been like. Please enjoy my discussion with Harley Finkelstein. 
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
     
    -----
     
    This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 
     
    -----
     
    Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.
     
    -----
     
    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
    [00:02:26] - [First question] - His interpretation and definition of a person’s life's work 
    [00:05:50] - The story of the riverstone and the average polished executive 
    [00:08:36] - The thing he can’t help but do; and focusing on our compulsions
    [00:13:12] - How he would boil things down to the most simple entrepreneurial formula; Distilled
    [00:16:38] - What is harder and easier about new business formation today 
    [00:21:03] - The countervailing forces for small-to-medium business entrepreneurship 
    [00:24:31] - What he’s learned about operationalizing ideas and mentor lessons
    [00:29:08] - A piece of fortune cookie advice that he finds terrible
    [00:30:49] - How Brands Grow; his philosophy on marketing & distribution  
    [00:35:27] - The most effective distribution strategies he’s seen work in Shopify that might be portable to other businesses
    [00:38:43] - What it was like getting their first app developer for the Shopify app store
    [00:41:17] - The state of ecommerce today writ large and what trends are interesting 
    [00:45:46] - Lessons learned about the digital places that people are buying 
    [00:49:06] - What it’s been like as an executive working at a company that had their stock price explode over the pandemic 
    [00:52:25] - Tips for communicating effectively with Wall Street
    [00:54:14] - An investor that stands out in memory that really impressed him
    [00:55:10] - Important aspects of his world that are worth mentioning 
    [00:57:04] - Lessons learned about motivating people through DJing 
    [00:59:12] - Whether or not reading the crowd can apply to business
    [01:03:49] - The kindest thing anyone has ever done for him

    • 1 hr 5 min
    Mitch Lasky - The Business of Gaming

    Mitch Lasky - The Business of Gaming

    My guest today is Mitch Lasky. Mitch is a partner at Benchmark and one of the leading figures in the video game industry. Over the last 30 years, he has built, led, and invested in a number of the best gaming companies in the world, including Activision, EA, Riot, Snapchat, and Discord. I couldn’t think of a better person to break down the anatomy of great gaming businesses and Mitch does not disappoint. His insights are remarkable. Please enjoy this excellent conversation with Mitch Lasky.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
     
    -----
     
    This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 
     
    -----
     
    Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.
     
    -----
     
    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
    [00:02:31] - [First question] - Why there aren’t more famous gaming investors
    [00:05:08] - The most important features of the modern gaming business model
    [00:07:11] - Developing his aesthetic taste and investing decision skill
    [00:08:03] - What makes a game fun 
    [00:09:26] - How delivering a pleasurable active user experience differs from passive content and media
    [00:11:09] - The developers of Doom being the first real modern video game company
    [00:13:09] - Half-Life’s important role in the development of the gaming industry
    [00:14:50] - The powerful notion of the platform-based publisher model
    [00:17:54] - How some of the big game aggregators get started in the first place
    [00:19:58] - What Riot can teach non-gaming businesses about business writ large
    [00:21:10] - Ways that the change from physical games to downloads changed monetization
    [00:25:19] - How to quantify an economic model in the new paradigm of superfan monetization
    [00:28:27] - What the shift in gaming platforms has done to the business model
    [00:31:47] - The impact of Apple’s privacy changes on gaming revenue
    [00:34:11] - How the access to professional game engines and a lower friction environment will change the industry
    [00:37:04] - Whether or not there is a step beyond mobile
    [00:39:42] - Ways platforms like Twitch and Discord have influenced gaming
    [00:42:26] - What he’s learned about games that allow them to seemingly exist forever
    [00:45:17] - Signs of a healthy gaming community
    [00:46:21] - The role of celebrities and influencers and generating retained audiences
    [00:47:45] - Whether or not crypto will unlock new opportunities for in-game monetization 
    [00:52:50] - Key categories of motivators that could replace a ponzi-style in-game inflation 
    [00:54:36] - Contrasting League of Legends versus a Ready Player One style world
    [00:58:22] - Emerging technologies and trends that may revolutionize the industry 
    [01:00:29] - A future with further consolidation on distribution and power
    [01:

    • 1 hr 13 min
    David Senra - Passion & Pain

    David Senra - Passion & Pain

    My guest today is David Senra. David has studied history’s great founders and entrepreneurs in more depth than anyone I’ve ever met, and I’d wager more than anyone else alive. In this conversation, we cover many of the most common themes he’s discovered studying hundreds of entrepreneurs like Estée Lauder, John Rockefeller, Enzo Ferrari, and Edwin Land. I found this to be one of the most energizing conversations I’ve had in a long time, and one I’ll return to often.
     
    David’s work and extraordinary energy aligns so well with our mission at Colossus that we’re excited to partner with him. You’ll soon be able to find his podcasts and transcripts at joincolossus.com where we hope you’ll learn as much from him as we have. If you like this conversation, be sure to subscribe to David’s podcast called Founders. Now onto our discussion. Please enjoy this great conversation with David Senra.
     
    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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.
     
    -----
     
    Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.
     
    -----
     
    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
    [00:03:01] - [First question] - When he first fell in love with reading
    [00:07:01] - What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders - Founders Podcast
    [00:10:34] - The first time he connected with someone as a positive role model that he was reading about 
    [00:13:45] - How often obsession is apparent in the founders he’s studied across hundreds of biographies 
    [00:18:08] - What is often behind obsession and how people listening can apply the lessons to their own lives
    [00:22:45] - The dynamic and relationship between inspiration and perspiration 
    [00:27:11] - Commonalities between the layers of leadership and support underneath founders
    [00:31:52] - Where else he’s seen ego rear its head in good and bad ways 
    [00:38:34] - How often do great founders break the law or enter gray areas of it 
    [00:41:22] - The role constant learning and listening plays in success
    [00:45:12] - Talking about how anything worth doing is worth doing to excess 
    [00:52:18] - Describing the soul of founders and businesses
    [00:58:39] - What he’s learned about all of these founders as it relates to marketing 
    [01:04:38] - A common story that

    • 1 hr 22 min
    Robert Smith - Investing in Enterprise Software

    Robert Smith - Investing in Enterprise Software

    My guest today is Robert Smith, the founder, Chairman, and CEO of Vista Equity Partners. An engineer by training, Robert started Vista at the turn of the millennium and built it into one of the world's most successful software-focused investment firms. We discuss the white space left in enterprise software investing, the importance of capital cycles, and what he’s learned building an iconic investing franchise. Please enjoy my discussion with Robert Smith.
     
    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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.
     
    -----
     
    Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.
     
    -----
     
    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
    [00:02:34] - [First question] - What the enterprise software market looks and feels like to him
    [00:05:52] - Whether or not software is becoming a saturated market and what will drive demand over the coming decades
    [00:09:42] - Bringing an engineering mindset to enterprise software investing and culture
    [00:12:36] - A single change he made to a business that stands out most in memory
    [00:14:33] - Qualities that are most critical in defining a good enterprise software company
    [00:18:07] - How the profile of companies he’s bought has changed over the years
    [00:20:33] - Categories of software he tends to gravitate towards 
    [00:23:56] - Evolving his model for considering what multiple to pay for a business and thinking about p/e growth multiples 
    [00:27:17] - Lessons learned about customer churn over his twenty two year career
    [00:29:44] - Capital cycles and how much they truly impact the software world 
    [00:31:53] - What elements of building Vista have most appealed to him over the years  
    [00:34:31] - Changing their investment strategy as the world continues to change
    [00:38:06] - The war for talent and what his senior team would debate most 
    [00:40:01] - Biggest mistakes Vista has made and what they taught him
    [00:41:09] - What has him most insecure or paranoid about the platform he’s built
    [00:43:10] - The advice he’d give on having good relationships with LPs
    [00:44:57] - The largest risk he or Vista has ever intentionally taken 
    [00:46:15] - What he’s learned about having a winning negotiations and sales approach
    [00:49:27] - Who he’d give all of his capital to outside of Vista
    [00:50:06] - How he arrived at the themes he ten

    • 56 min

Customer Reviews

4.5 out of 5
30 Ratings

30 Ratings

radhku ,

One of the best

I am only through a few podcasts and my experience with these is mind-blowing. Excellent guests and they are thought leaders in their areas. During Q

TheMoneyHans ,

The best investing podcast!

I stumbled on to this podcast soon after it started. I was impressed with the level of questioning as well as the quality of guests answering. It’s gone from strength to strength. I am amazed by the willingness of guests to share...which makes it a great resource for learning. I recommend it to everyone in the investment industry, sometimes even to non-finance people.

Top Podcasts In Business

Finshots
Farnam Street
Stanford GSB
The Ken
Ankur Warikoo
The Ken

You Might Also Like

Colossus | Investing & Business Podcasts
Ted Seides – Allocator and Asset Management Expert
Jim O'Shaughnessy and Jamie Catherwood
Bloomberg
Meb Faber
Colossus

More by Colossus