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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: October, 2022
Oct 25, 2022

My guest today is Jason Droege, a venture partner at Benchmark. Jason’s had a long entrepreneurial career, which most recently culminated in building and leading Uber Eats. He joined Uber in 2014 with a blank piece of paper to grow the business beyond ride sharing. Within six years, he found product market fit with food delivery, refined the service, and scaled Uber Eats to a global $20 billion GMV run rate. Our conversation pulls out the most important lessons learned during that period and how Jason now employs them in his role at Benchmark. Please enjoy this great conversation with Jason Droege.

 

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. 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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. 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.

 

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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

[00:02:52] - [First question] - What it was like at a high level building Uber Eats

[00:07:38] - How he would structure entrepreneurial incentives on a platform like Uber for a new leader or team attempting to build on top of it

[00:10:17] - What he learned about selecting competitive frontiers and mistakes made while building Uber Eats

[00:15:17] - Things that Uber Eats got most right that he’s proud of 

[00:18:16] - Constructive mistakes that taught him a lot from his time with Uber Eats

[00:20:36] - What made India such a competitive environment 

[00:22:50] - Building a business with an uncertain end state of unit economics 

[00:26:13] - What improved the most in his playbook for launching in a new city

[00:27:14] - Defining what best means in this competitive sector  

[00:29:01] - Dealing with suppliers in different categories and finding an ideal balance

[00:32:09] - When monogamy between the buyer and supplier matters and when it doesn’t in a marketplace 

[00:33:29] - Other attributes of a marketplace he’d pay special attention to as an investor given what he’s learned building one

[00:36:12] - Defining what founder market fit is and being “fingertippy”

[00:37:29] - His views on the relationships between leaders of businesses and their cultures

[00:40:26] - Why Uber believed in him more than he did 

[00:41:40] - What he learned about marketing to suppliers specifically 

[00:43:44] - Find new businesses by looking for areas that technology hasn’t yet affected

[00:45:18] - Differing views he has on the concept of failure  

[00:47:31] - Thoughts about ideas versus execution and the relative importance of the two

[00:49:10] - Effectively measuring opportunity cost and using it in decision making  

[00:51:14] - What it’s like being inside of a consumer business that people have so many opinions about

[00:56:30] - How he would describe the landscape and state of the market he was in from a higher viewpoint today

[00:58:56] - The most interesting things he’s learned from his time as a partner at Benchmark

[01:00:15] - The kindest thing anyone has ever done for him

Oct 18, 2022

My guest today is Paul Orfalea. Paul founded Kinkos, the popular copy chain, in 1970. He started with a single photocopy shop in California and grew the business into a $2 billion multinational operation over the course of his 30 years in charge. Paul is a non-traditional leader in the best sense and we discuss his philosophy of business building, from why your subordinates should frustrate you, why you shouldn’t love your business and tips he learned on hiring well. Please enjoy this conversation with Paul Orfalea. 

 

Founders podcast on Paul Orfalea.

 

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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/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

[00:02:58] - [First question] - What it was like to be a very bad student in highschool

[00:04:22] - When he first realized he was unemployable

[00:05:02] - The origin story of the very first Kinko’s

[00:06:13] - What the ideal progression of an entrepreneur is in his mind 

[00:06:57] - Recognizing real customer problems and what he enjoys most about sales

[00:07:53] - Finding what has worked well in each Kinko’s and coaching managers

[00:08:54] - Something he found that a manager was doing that blew him away

[00:10:22] - Getting messages from his brain to everyone else in the Kinko’s network 

[00:11:45] - The difference of working on and not in the business

[00:13:22] - What he got better at when it came to managing people 

[00:13:57] - Why a good salesperson will sell you broke  

[00:14:41] - Disagreeableness as a positive characteristic for people in business

[00:15:08] - Whether or not candor is different from disagreeableness

[00:15:36] - Why he teaches, what he teaches, and his teaching style

[00:18:31] - Explaining the Federal Reserve in two minutes  

[00:19:47] - What students most commonly want from him  

[00:20:06] - Whether or not making yourself inaccessible as a leader is good for promoting a self-starter attitude amongst team members 

[00:21:39] - The story about tearing down a sign that was antagonistic to a customer

[00:21:58] - The role of anger in his career and something he’s worked on over time

[00:22:31] - Where Kinko’s falls on the spectrum of bad to great businesses

[00:24:09] - Characteristics he’d look for in founders to back a business early

[00:25:08] - Qualities of a business he’d cultivate more or less if he could start over

[00:26:18] - Lessons learned about using the word employee

[00:26:42] - His strategy for where to go next once he had his original concept

[00:27:21] - The most clever marketing strategy he ever deployed or designed

[00:27:45] - Learning to spread the glory instead of the money  

[00:28:30] - The state of entrepreneurship today compared to when he started 

[00:29:50] - How he instilled frugality and the saving mentality in the business 

[00:30:42] - What motivated him across his career

[00:31:35] - Why being in it for the money seems odd in today’s lens

[00:32:34] - Who he most admired or most admires today 

[00:32:51] - Let My People Go Surfing: The Education of a Reluctant Businessman

[00:33:08] - Preserving the alignment of integrity and action 

[00:33:42] - What it felt like to sell a business he’d worked so hard on 

[00:34:57] - How good he is naturally with numbers and math being dyslexic 

[00:37:17] - Defining success as having your adult children want to hang out with you and what stood out about his parents to him 

[00:38:05] - His parents’ impression of him while he was building Kinko’s 

[00:38:34] - What has his interest and keeps his interest most 

[00:39:56] - The most interesting person he’s ever worked with at Kinko’s

[00:40:48] - What he would have done differently if he started from scratch

[00:41:24] - Something that is most underappreciated about the United States 

[00:43:00] - The kindest thing anyone has ever done for him 

[00:43:57] - A big lesson he’s earned in a deeper way that he wishes he could share with others

Oct 11, 2022

My guest today is Madhavan Ramanujam. Madhavan quite literally wrote the book on how to price products, it’s called “Monetizing Innovations” and his concepts have been used by companies across the world like Porsche, Uber, LinkedIn, and SuperHuman. Our conversation is a masterclass on pricing. We discuss common mistakes when pricing products, why you need to focus on benefits rather than features, and how to pick the right monetization model. Please enjoy my conversation with Madhavan Ramanujam.

 

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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. 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

[00:02:48] - [First question] - How he arrived at a radically different way of building products

[00:05:07] - An example of coming up with a price before the product

[00:08:35] - Distinctions between a willingness to pay and positive feedback 

[00:10:29] - How to make sure you’re talking to the right potential customer in the first place

[00:13:32] - Productizing for different customer segments 

[00:16:16] - Questions companies should be asking to get accurate feedback

[00:21:18] - What he’s learned about the motivations of potential buyers

[00:22:43] - What leaders, killers, and fillers are

[00:24:37] - Some of the biggest mistakes companies make while following his formula

[00:25:35] - A rule of thumb for what is a benefit versus a feature

[00:27:35] - Five distinct pricing models for charging a customer

[00:30:46] - Whether or not the value piece of all of this revolves around time and money

[00:33:27] - What he tells entrepreneurs about pricing their products that most surprises them 

[00:35:16] - Defining the first four categories of failure 

[00:40:13] - Reasons why so many innovations fail to monetize and pricing being a CEO topic

[00:41:51] - Good rules that leaders can use to have a general sense for effective pricing 

[00:47:38] - Behavioral changes and observations as the absolute price move up and down 

[00:50:36] - Is there a pricing genius we should take note of?

[00:53:18] - The single question every leader should ask themselves

[00:53:46] - The kindest thing anyone has ever done for him

Oct 4, 2022

My guest today is Scott Wilson. Scott is the CIO of Washington University’s endowment, which manages over $13 billion. In this conversation we discuss WashU’s non-traditional endowment model and cover a variety of asset classes and geographies. We talk about the qualities Scott looks for in managers, lessons from investing in Asia and emerging markets, and red flags in the venture space. Please enjoy this conversation with Scott Wilson.

 

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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. 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

[00:02:38] - [First question] - What he learned about markets from quant fixed income trading 

[00:04:42] - How his experience shaped his degree of skepticism of the world

[00:05:15] - The story that brought him to Grinnell College 

[00:06:45] - What his education was like back in 2010 and what seemed sensible and insane when he arrived

[00:08:05] - The style of investment he learned at Grinnell compared to his style now

[00:09:37] - His philosophy around trying to have more direct ownership

[00:11:00] - Why their co-investment approach is outperforming the rest 

[00:12:03] - Lessons learned about choosing good partners and doing it effectively over time

[00:13:51] - Things that are most enjoyable about getting to know new managers 

[00:14:25] - The role that global travel and having boots on the ground plays in his success

[00:16:17] - Why they spend so much time in frontier and emerging markets

[00:18:21] - Lessons learned from investing in China and thoughts on it today 

[00:20:10] - What else he’s learned in continental Asia outside of China

[00:21:02] - Interests and red flags when it comes to investing in the venture space

[00:23:16] - The worst things he sees from venture investors 

[00:24:39] - Whether or not venture investors should care more 

[00:26:16] - The virtues and vices in private equity and his thoughts on that space

[00:27:55] - What percentage of investors in private equity are investors versus just involved to try and engineer returns

[00:28:59] - His impressions on hedge funds and the evolution of the hedge fund model

[00:31:18] - The role that credit can play in a portfolio like the one he manages now 

[00:33:10] - Common characteristics of managers that perform well in credit 

[00:34:20] - How he thinks about the sources of returns in the “other” portfolio category 

[00:36:34] - Everything he’s learned about asset managers acting as asset gatherers

[00:39:35] - Ways he fights convergence and tracking error overseeing so much capital 

[00:41:49] - What it’s like to go through the bad side of tracking error

[00:44:27] - Thoughts on how the macro environment influences allocating time and resources

[00:45:43] - What he sees as a normal level of tracking error for endowments and foundations

[00:46:59] - Why such big pools of institutional capital tend to look so similar 

[00:48:10] - Whether or not real estate sits somewhere between stocks and bonds

[00:49:07] - The cultivation of a talented investment team and effectively teaching investing 

[00:51:10] - Colliding managers in a fun and spirited way at meetings 

[00:52:16] - An investing trip from his career that he finds most memorable

[00:53:34] - Whether or not the factors that sort winners from losers will be different today compared to a decade ago

[00:52:50] - The kindest thing anyone has ever done for him

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