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Invest Like the Best with Patrick O'Shaughnessy

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
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Invest Like the Best with Patrick O'Shaughnessy
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Now displaying: February, 2023
Feb 28, 2023

My guest this week is Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear. Please enjoy my great conversation with Doug Leone.

 

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

 

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This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick.

 

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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

[00:03:21] - [First question] - What Don Valentine’s heart was like
[00:06:30] - The most productive and unproductive parts of Don’s toughness 

[00:09:01] - Being the opposite of insufferable and how it was different when he was younger

[00:10:55] - Why it’s so important to understand someone’s core motivations

[00:14:18] - Questions or topics he returns to when getting to know people 

[00:15:31] - How much time he believes it can take to really get to know someone  

[00:16:44] - The most formative experiences he had prior to becoming an investor that impacted his investing the most 

[00:20:37] - What venture looks like to him today relative to his prior career

[00:23:51] - His style of approaching emerging technology markets like AI as an investor  

[00:26:37] - Whether or not he’d go into venture today if he was in his late 20s 

[00:28:30] - Commonalities between the very best at going to market effectively 

[00:31:11] - The key components of great product positioning  

[00:32:10] - Helping companies circumnavigate mediocre positioning 

[00:33:25] - Generating demand and leads and doing it well 

[00:37:15] - How interacting with companies early on has changed over the ears

[00:41:12] - Whether or not new entrants into venture should build firms with enterprise value 

[00:46:14] - Sussing out the killer gene in somebody 

[00:47:25] - What high school was like for him when he first came to the US 

[00:49:04] - How successful people can instill the lessons learned from hardship into their children 

[00:50:45] - The most common failure modes he’s seen for investors 

[00:52:30] - Whether or not competitive advantage can be architected ahead of time when building a company  

[00:53:52] - Whether or not his view on competitive advantage has changed  

[00:55:21] - The early 2000s clawback at Sequoia and what navigating that period was like 

[00:59:06] - What he’s learned about picking the right LPs and partnering with them

[01:00:40] - The most interesting question an LP has ever asked him 

[01:02:18] - Making sure that performance is on everyone’s minds all the time 

[01:04:04] - What the components of a fantastic investment memo are

[01:05:00] - Which dinner companions he’d pick to educate a newly successful founder

[01:05:29] - What first popped out at him as black magic when he started investing

[01:07:59] - The kindest thing anyone has ever done for him 

Feb 21, 2023

I’m excited to share this conversation with Tim Urban. Tim is, in my opinion, one of the best and most engaging writers of our era. He’s tackled many of the most interesting topics in the world from AI to procrastination. I interviewed him in 2017 in an episode we called “Grand Theft Life”, and it remains one of my favorite episodes ever.

 

In the 6 years since that episode, he hasn’t published almost anything. That’s because he’s been writing the book we discuss in this episode. The book is called “What’s Our Problem”, in which Tim investigates the big issues facing society.

 

The reason I love Tim’s writing so much is its density of ideas and ridiculously clear explanations: a rare combo that makes reading a joy. I hope you enjoy this great round two with Tim Urban, and go buy and enjoy his great new book.

 

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

 

Listen to Founders podcast.

 

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This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive 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

[00:02:50] - [First question] - What it’s been like spending seven years thinking about a single topic: Tim's book, What’s Our Problem?

[00:05:05] - How he’s come to articulate the big question he’s trying to answer in his book

[00:07:58] - A dinner experience where a single question showed just how much of a problem there was to solve

[00:09:47] - Group ideology and the different ladder rungs of human thinking 

[00:17:28] - The concept of a social golems and genies and their implications for society 

[00:23:02] - His favorite genies and golems throughout history and their impact  

[00:29:07] - Examples of canonical high functioning genies across history   

[00:34:20] - The key ingredients within liberal democracies that allow for and correct golems

[00:40:44] - Media’s role in shaping ideas and society and what’s changed about it in today’s media landscape 

[00:46:46] - What else is going on that has him worried about modern institutions that are failing as social immune systems

[01:01:15] - The gap between what we say publicly versus what we feel privately and the growing pile of unsaid things 

[01:07:18] - What’s to be done in order to help society repair itself 

[01:14:09] - Whether or not the direction we’re most afraid to run is where we should 

[01:17:37] - Thoughts on AI having written extensively on it and the new wave of emerging tools

[01:22:13] - The role and impact of leadership in regards to golems and genies 

Feb 14, 2023

My guest today is Dan Rose. Dan is the chairman of Coatue Ventures and has one of the most interesting collections of experiences of anyone I’ve talked to. He spent 20 years at Amazon and Facebook in their early days, working closely with Jeff Bezos, Andy Jassy, Mark Zuckerberg, and Sheryl Sandberg. He’s had a front-row seat to the defining products and founders of our era and his lessons from those experiences do not disappoint. Please enjoy this great discussion with Dan Rose.

 

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. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick.

 

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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

[00:03:27] - [First question] - The story behind Amazon’s Kindle and the lessons it taught him

[00:09:19] - Amazon’s philosophy of working backwards and the most creative solutions he and his team had to come up inside of that framework 

[00:13:04] - What he did to convince publishers to get on board with his vision 

[00:16:02] - His overall experience of the relationship between innovation and constraints

[00:18:43] - Thoughts about the fine line between genius and nutcase 

[00:22:02] - What the key points of his theory on partnerships would be 

[00:24:28] - When advising portfolio companies becomes relevant 

[00:26:09] - The dark arts of building companies that could be adopted by partnerships 

[00:28:40] - Why he thinks the best technology companies drive strategy through product 

[00:29:24] - What unites the communication layer between great leaders communicating a vision well

[00:32:23] - Resolving micro management while also giving skilled talent their own space

[00:36:07] - Where Javier Olivan fits into his ideal executive team 

[00:36:57] - What about growth requires its own expertise 

[00:37:35] - What makes Dave Schneider an ideal sales leader

[00:39:08] - The most stressful period of time while working at Facebook

[00:42:51] - General thoughts on great versus good business models in tech 

[00:45:36] - Topics where Jeff Bezos and Mark Zuckerberg would disagree the most 

[00:47:13] - Defining the platonic ideal of a great investor approaching corporate enterprises 

[00:50:25] - Overview of the investing environment we’re in today from coast to coast

[00:53:45] - Other questions he loves and thoughts on Bezos asking people if they felt they were lucky or not 

[00:55:07] - What made Sheryl Sandberg so successful; Lean In

[01:00:35] - Why he started his career at Life Mastery selling personal growth seminars 

[01:05:47] - What will define the next generation of leaders 

[01:07:59] - A product he would build if he could that doesn’t exist yet

[01:08:59] - The kindest thing anyone has ever done for him 

Feb 7, 2023

My guest today is Jeff Green, the CEO and co-founder of advertising platform, The Trade Desk. The Trade Desk is the second advertising exchange Jeff has built, having sold his first venue to Microsoft in 2007. He started The Trade Desk in 2009 and has built it into a $30 billion public business. In our discussion, we talk about the parallels between The Trade Desk and an equity exchange, why Jeff chose to align with ad buyers not sellers, and how he shapes the culture of his firm. Please enjoy my conversation with Jeff Green.

 

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

 

Listen to Founders podcast

 

Founders Episode #136 A Success Story: Estee Lauder 

 

Founders Episode #288 Ralph Lauren


Invest Like the Best with David Senra: Passion & Pain

 

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This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive 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

[00:03:09] - [First question] - What he’s learned about human behavior and how it’s impacted his business

[00:05:45] - Big differences in generational and perennial behavior 

[00:06:56] - The strong link between vulnerability and creativity  

[00:07:42] - The necessary preconditions that allowed him to build Trade Desk the way he did

[00:10:53] - What it would have felt like as an early stage employee at Trade Desk 

[00:12:43] - The hardest parts about maintaining his type of company culture

[00:14:05] - How much of his company culture is interwoven systemically or whether it arises naturally based on talent choices

[00:15:59] - Defining what talent means to him and the dimensions of it that matter

[00:18:32] - Laying out what a compelling vision is to him and in the general sense 

[00:22:03] - What he’s learned about delivering messages effectively  

[00:23:49] - The founding story and history of Trade Desk 

[00:28:33] - How he thinks about the key stakeholder groups around Trade Desk’s platform

[00:30:50] - Figuring out who Trade Desk’s key customers were and identifying them writ large

[00:34:55] - The composition of the universe and market of those who buy advertising 

[00:36:11] - Practical product implications based on their choice of service 

[00:40:16] - Building inventory legibility and its dimensions and importance 

[00:44:26] - What it’s like building a business that serves the biggest corporations in the world and what the revenue curve is like for that

[00:47:55] - The time between the first line of code to a multi million dollar revenue stream

[00:50:29] - Markers for technology companies he’d look for that could achieve a similar scale 

[00:53:35] - How not being able to simulate poverty or hunger translates into his parenting 

[00:57:10] - Describing the margin differences between Trade Desk and Google

[00:59:00] - What stands out as the defining moment in his firm’s history 

[01:01:50] - The kindest thing anyone has ever done for him

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