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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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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

 

-----

 

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

Jan 31, 2023

My guest this week is Carl Kawaja. It’s the second time I’ve had Carl on the show and my first conversation with him is one I go back to often. Carl is a portfolio manager at Capital Group, where he’s quietly overseen a huge portfolio for decades. He is one of the top investors operating today as well as one of my favorite people. The investing world has changed quite a bit since Carl and I first spoke in mid-2021 so this was a great chance to use Carl’s curious mind and wide range of experiences to discuss the regime change taking place across capital markets. In true Kawaja fashion, we go all over the map and discuss Apple, the Amazonian rainforest, baseball, the oil & gas industry, Muhammad Ali, and more. Please enjoy my great discussion with Carl Kawaja.

 

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.

 

-----

 

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

[00:02:44] - [First question] - What the market feels like to him today

[00:06:00] - The pros and cons of the cost of capital and experimentation

[00:09:09] - Things we can learn from Oil & Gas stocks and resource commodities in general

[00:14:38] - Pulling apart the key lessons from Berkshire’s purchases of IBM and Apple

[00:20:37] - The practical implications of wanting to land more soft-wins in investing that aren’t apparent out of the gate

[00:25:52] - How he approaches and considers products and product cycles writ large

[00:31:10] - The Systems Bible

[00:33:15] - Thoughts about making money from value based strategies 

[00:38:31] - His methodology to go about finding the next diamond in the rough 

[00:42:48] - A New Innings

[00:45:13] - The Arc of Boxing; Lessons from Muhammad Ali fighting Cleveland Williams

[00:48:54] - Someone he thinks is an exemplar in both business and the world

[00:54:37] - Don’t Sleep There Are Snakes

[00:59:41] - The role fossil fuels play in the energy transition and the current regime change 

[01:07:35] - What we can learn from uncontroversial transitions in the past

Jan 24, 2023

My guest this week is Daryl Morey, who is President of basketball operations for the Philadelphia 76ers. Daryl is a computer science graduate but has become one of the NBA’s most successful General Managers during his time with the Houston Rockets and the 76ers. Together with my friend and past guest of the show, Sam Hinkie, Daryl pioneered the analytics movement in basketball. He’s been so influential his style has its own name, “Moreyball”, a nod to Michael Lewis’s book about baseball, Moneyball. Daryl is also the co-founder of the MIT Sloan Sports Analytics Conference, which has become the gold standard forum for leaders in sports analytics. I had a blast talking to him about negotiation tactics, systems thinking, hiring, and a ton more. Please enjoy this great conversation with Daryl Morey.

 

Listen to Founders podcast

 

Founders Episode #136 A Success Story: Estee Lauder 


Invest Like the Best with David Senra: 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 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.

 

-----

 

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

[00:03:15] - [First question] - The basic principles of sports and what makes for a great sport

[00:09:54] - How resource concentration influences outcomes in various sports

[00:13:13] - The degree of certainty in predicting sports outcomes based on existing data

[00:16:32] - Using the concept of KPIs to optimize for certain characteristics to win games

[00:18:45] - Training teams on specific systems and plays versus leveraging individual talent

[00:21:07] - Why superstar athletes are key to success in basketball

[00:24:02] - Dealing with constant expected value calculations to appease stakeholders

[00:25:30] - Building the organization’s back office to find talented athletes

[00:28:32] - How he and other GMs make organization-level decisions

[00:34:12] - Why he’s involved with basketball as opposed to other sports

[00:36:17] - How he uses his frameworks to figure out systems outside of mainstream sports

[00:37:41] - Problems with the rules and economic factors of professional soccer

[00:41:53] - Suggestions to mitigate huge point spreads that make viewers disinterested

[00:42:54] - Trends he’s observed in the worlds of music, movies, and books

[00:45:33] - His perspective on developing one’s own career path

[00:48:22] - How challenges in his youth benefited him in the long run

[00:49:28] - The person he would call for advice if he was stuck in a foreign prison

[00:51:01] - His emphasis on first principles and why he supports free speech

[00:52:31] - Takeaways from a Harvard negotiation class he took

[00:57:07] - The power of refining the terms and definitions of a deal post-negotiation

[00:58:51] - The four people in the world that intrigue him most

[01:01:40] - The kindest thing anyone has ever done for him 

Jan 17, 2023

My guest today is Miles Grimshaw. Miles is in his early thirties and is a General Partner at Benchmark. His experience and success belie his age. He was an early investor in Segment, Benchling, and Airtable, all before they had 30 employees. I have learned a ton from Miles about software investing and that’s why I was excited to have him on the show. We discuss his biological approach to investing, whether pure API companies can be good businesses, and what most has his attention right now. Please enjoy this conversation with Miles Grimshaw.

 

Listen to Founders podcast

 

Founders Episode #136 A Success Story: Estee Lauder 

 

Invest Like the Best with David Senra: 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 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.

 

-----

 

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

[00:02:57] - [First question] - His notion of the investor as a biologist or a physicist

[00:05:24] - Why he seeks out new companies with unique business models

[00:07:53] - How his investments are based on present and future needs in the market

[00:11:55] - Evaluating the genetics of a nascent or small company

[00:13:38] - The half-life of information as it flows through a company or platform

[00:17:26] - Unpacking how software companies can survive re-evaluation periods

[00:21:03] - The power of environment creation and facilitation

[00:25:10] - The importance of user conferences

[00:25:45] - A company’s potential for a differentiated second act as a sign of good genes

[00:30:21] - Product quality, timing, and reinvention in tech startups

[00:33:10] - Why it’s crucial for companies to avoid copying their heroes

[00:37:41] - Breaking down market perspective on pure API companies

[00:41:29] - His views on software targeted to vertical versus horizontal markets

[00:44:29] - Carefully leveraging relationships with core customers

[00:48:06] - Operational lessons from his experience with the companies he’s invested in

[00:50:26] - His maxim that software development is as much an art as a science

[00:51:12] - His idea of a product magician in the software industry

[00:52:19] - Effects of new products and categories at the forefront of the space

[00:58:21] - How software founders should prepare for 2023

[01:01:41] - How both market structure and product shape the genetics of a business

[01:04:32] - The challenge of pricing and packaging for SaaS companies

[01:06:42] - Cardinal sins in software investing

[01:07:42] - The kindest thing anyone has ever done for him

Jan 10, 2023

My guest today is John Fiorentino. John is a product inventor and entrepreneur who, in the space of a few years, has bootstrapped four products; Gravity Blanket, Moon Pod, Moon Pals, and Birthdate Candles which have collectively sold hundreds of millions of dollars of revenue. Our conversation is quite different than normal. Alongside his successful brands, John has had a range of life experiences – from starting as a Jazz musician to working for Justin Bieber - that give him an original worldview. I was especially interested in his points around product positioning, creating magic for consumers, not letting yourself become the product, and how to build enduring brands. Please enjoy this great conversation with John Fiorentino.

 

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.

 

-----

 

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

[00:02:25] - [First question] - The amazing story behind Gravity Blanket

[00:08:51] - What he’s learned about positioning relative to product

[00:13:17] - How fundamental truths drive creativity in commerce

[00:16:17] - Real-world examples of magic as he defines it

[00:19:50] - The investability of consumer businesses from his perspective

[00:25:25] - His contrarian thoughts on venture-backed startups

[00:28:00] - How unique personalities create compelling IP and monetize it

[00:38:28] - The fine line between creative power and self-destruction for brand founders

[00:45:13] - The importance of consumer business goals being larger than oneself

[00:48:45] - The story of the Moon Pals weighted stuffed animals

[00:53:15] - How investors undervalue IP and mythology

[00:57:20] - Leveraging uniqueness as a founder to boost your brand power

[01:00:53] - His eye-opening experience working on Justin Bieber’s team

[01:05:20] - How he identifies potential magic-makers and enables them

[01:09:16] - An odd commonality between high-level successful people

[01:12:14] - Whether or not one could map out their own archetype framework

[01:15:23] - The dangers of focusing on one’s own persona and image as the product

[01:18:19] - The kindest thing anyone has ever done for him

Jan 3, 2023

My guest today is Amjad Masad. Amjad is the founder and CEO of Replit, whose mission is to bring the next billion software creators online. Replit has built a browser-based coding environment that makes coding more fun, collaborative, and approachable. We discuss how that is possible and why the way most of us interact with computers today is suboptimal. We then go into the effects of AI on software creation and its broader impacts on technology. Please enjoy my conversation with Amjad Masad.

 

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.

 

-----

 

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
[00:02:18] - [First question] - The Steve Jobs black-pill 

[00:06:02] - Speculation on the near future of programming

[00:09:38] - Potential convergence of simple software and coding tools

[00:11:23] - What an IDE is and how it works

[00:12:44] - The definition of REPL and the role of Replit in the space

[00:14:21] - Decreasing friction in a programming environment using primitives

[00:19:47] - Real-world effects of Replit’s low-friction design

[00:23:27] - His perspective on new coding and AI technologies

[00:30:29] - Promises and limitations of the user-friendly programming movement

[00:33:16] - The dynamic nature of IDE technology and its challenges

[00:39:53] - How he’s priming his team to react to new technologies like the upcoming GPT-4

[00:43:58] - Recommended skills and training for the AI world of the future

[00:47:21] - The impact of IDE and AI tech innovations on existing tech giants

[00:51:56] - His mixed but optimistic views on the trajectory of AI

[00:54:40] - Recommendations for the curious listener without a programming background

[00:56:50] - The role of smartphones in the IDE movement

[00:58:28] - The kindest thing anyone has ever done for him

Dec 27, 2022

My guest this week is Rebecca Lynn. Rebecca co-founded early-stage investor Canvas Ventures in 2013 and is regularly featured as one of the best VCs in the market. She has deep positioning and go-to-market experience, which she honed during her time at Procter & Gamble, and that's the focus of our discussion. We cover the details of great marketing, why you should say no to customers, and how she has built Canvas. Please enjoy my discussion with Rebecca Lynn.

 

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

[00:02:37] - [First question] - What she’d do a great job teaching if she could teach a singular 401 level course

[00:05:20] - Defining what the umbrella concept is 

[00:06:10] - What about her career at P&G applies most to the kinds of companies she spends her time with now 

[00:12:06] - What types of questions she asks to help someone building a product understand their marketing angle 

[00:15:34] - The top three things people do wrong when running a survey in tactics or strategy

[00:19:33] - Categories of questions where surveys are always helpful and effective   

[00:21:06] - What the Go-To-Market Council is and what it does 

[00:28:21] - The ways that most funnels are commonly broken  

[00:31:17] - Defining great positioning and what it accomplishes

[00:33:36] - How her knowledge and ideas most impacted the way she built Canvas

[00:35:04] - Lessons learned about the world of digital health and the quantified self  

[00:39:15] - The base level attributes that most indicate investment potential when she’s investing in a company

[00:42:32] - The shifts in the world that most have her attention today

[00:46:10] - What has her worried systemically about venture investing 

[00:49:37] - The kindest thing anyone has ever done for her 

Dec 20, 2022

My guest this week is Michael Mauboussin. Many of you will know Michael and his work well. He’s Head of Consilient Research at Counterpoint Global, one of the sharpest investment minds I know, and a frequent guest on this show. In this discussion, we go deep into his recent work on market share, returns on capital, and capital allocation - all of which are coming under increasing scrutiny for different reasons. Please enjoy this great conversation with my friend Michael Mauboussin.

 

Listen to Founders podcast

 

Founders Episode #136 A Success Story: Estee Lauder 

 

Invest Like the Best with David Senra: 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 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

[00:03:46] - [First question] - Overview of Michael’s recent research on market share

[00:05:48] - Market share dynamics in modern history

[00:08:43] - How market share data is useful for investors

[00:12:30] - Investing in early breakout companies from low-concentration markets

[00:14:34] - Surprises from his recent research project

[00:15:29] - Using the value stick for stakeholder satisfaction

[00:19:12] - Examples of value creation using the value stick

[00:23:33] - Market power in relation to markups and willingness to pay

[00:32:00] - Identifying a company’s real ROIC numbers

[00:44:00] - How important absolute ROIC is when picking investments

[00:47:07] - Research on capital generation and allocation trends

[00:54:25] - Characteristics of great capital allocation strategies

[00:59:26] - Surprises in the market since his deep-dive research

[01:02:54] - Artificial intelligence and other sources of disruptive innovation

Dec 13, 2022

My guest this week is Jeremiah Lowin. Jeremiah has been on the podcast a number of times over the years. He’s one of my oldest friends who has been a sounding board for me throughout my career. Today he is the founder and CEO of Prefect, which helps companies automate and orchestrate their dataflows. In full disclosure, Positive Sum is an investor in Prefect. We didn’t plan this conversation, but when OpenAI released ChatGPT, I called Jeremiah for a primer on what’s happening under the hood and how best to contextualize this product amidst the growing AI movement. We have these conversations often, but this time I decided to record it so we can all learn from someone I consider to be a leading mind in the fields of data science and machine learning. We start off in the weeds and zoom out as the discussion unfolds. Please enjoy this conversation with my friend, Jeremiah Lowin.

 

Listen to Founders podcast

 

Founders Episode #136 A Success Story: Estee Lauder 

 

Invest Like the Best with David Senra: Passion & Pain

 

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.

 

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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

[00:03:38] - [First question] - What a pre-trained transformer is 

[00:06:12] - What latent representation means in the context of AI models 

[00:09:57] - Models using math to interpret input data and generate images accurately 

[00:11:43] - Whether or not understanding AI complexity in light of the results they arrive at will become a black box scenario 

[00:14:13] - A high level history of the companies involved in generative AI

[00:17:51] - The precursory technology that makes generative AI art possible

[00:21:01] - What people are doing to improve AI models in between versions 

[00:26:39] - Things that are literally happening during AI training

[00:29:44] - The power dynamics and barriers to entry for building AI models

[00:33:38] - Whether or not AI models might one day function as a utility like electricity

[00:36:01] - Coding using GitHub Copilot and what it’s felt like to use it 

[00:40:30] - How he’d approach starting an AI company from scratch 

[00:44:40] - Developing this technology beyond general and into specific use cases

[00:49:44] - The secret sauce for defensibility in the AI model space 

[00:53:02] - What he’s watching more closely as the story unfolds 

[00:56:32] - Whether or not he thinks that these toolkits will eventually learn how to use other systems like Unreal Engine on our behalf 

Dec 6, 2022

My guest today is Bill Lenehan. Bill is the CEO of Four Corners Property Trust, a listed REIT and one of the leading owners of restaurant real estate in the US. Their portfolio is made up of 982 properties across 47 states. Real estate is something most of us own, whether as an investment or a home, and Bill’s insight into the asset class at this particular moment in time is fascinating to hear. Please enjoy my conversation with Bill Lenehan.

 

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.

 

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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

[00:03:19] - [First question] - Recent increases in mortgage rates and a frozen housing market

[00:08:55] - Projected real estate trends over the next decade

[00:13:38] - How a company’s ROI can be more consistent with backing from a real estate firm

[00:16:41] - Risk-return rate and risk exposure in real estate compared to other asset classes

[00:20:09] - The skills, traits, and circumstances that make a top-level real estate investor

[00:22:38] - Stand-out learnings from his time at Farallon Capital Management

[00:33:20] - The value of shopping malls and offices in a post-COVID, e-commerce US

[00:39:27] - Pros and cons of different types of real estate investments, including REITs

[00:43:22] - The impact of climate change on the real estate market

[00:45:39] - The role of modern technology in investing and in real estate infrastructure

[00:51:10] - Hard costs of building and renovating for the future

[00:54:20] - How hard costs and supply levels impact rates of return and housing costs

[00:57:17] - How the retail industry is adapting to consumer trends

[01:01:23] - Why retailers need to adapt to a changing economy and how they’ll do it

[01:04:03] - The relative magnitude of change in today’s real estate market

[01:06:51] - The role health and wellness plays in real estate and finance

[01:09:28] - What it feels like to be investing in 2022

[01:12:23] - The kindest thing anyone has ever done for him

Nov 29, 2022

Today I’m joined by two Hollywood greats, Ron Howard and Brian Grazer. They have produced, directed, written, and acted in a number of the most popular films and tv shows ever made, including Apollo 13, A Beautiful Mind, 24, and Frost/Nixon. Their partnership is one of the longest running in Hollywood, and the business they founded in 1985, Imagine Entertainment, has won 49 EMMY awards, 11 Golden Globes, and 10 Academy Awards. There are few better storytellers in the world and it was a thrill to talk about curiosity, trust, and business building with them both. Please enjoy this great conversation with Ron Howard and Brian Grazer.

 

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 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

 

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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

[00:02:44] - [First question] - The value of trust and how Ron built it up over time with Brian

[00:08:34] - The spark that allowed Brian to trust and work with Ron 

[00:14:45] - Ray Stark calling Brian and threatening him over their mermaid movie

[00:16:37] - Keeping their creative spark alive as their business scaled and matured 

[00:20:20] - Principals like the universality concept that they return to most commonly 

[00:23:24] - Seemingly bottomless wells of inspiration that they both pull from

[00:26:18] - Curiosity precedes innovation and the curiosity conversations Brian has

[00:30:15] - The pitch format Brian uses to try and secure a guest for a curiosity talk

[00:32:16] - The role of engaging with conversations or ideas Brian disagrees with 

[00:33:56] - How curiosity shapes the nitty gritty of Ron’s directing and producing 

[00:37:41] - The biggest mistakes they’ve come across that people make telling stories

[00:40:27] - Pinpointing the defining moments of their careers outside of the obvious wins

[00:44:27] - Thoughts about how the industry has changed across their careers

[00:47:19] - How they’ve gotten better at taking a project from nothing to the finish line 

[00:49:53] - The kindest things anyone has ever done for them  

Nov 22, 2022

Today’s episode is a special one, in a format that may turn into a series. It is a conversation between Ravi Gupta and Shane Battier. Ravi is a partner at Sequoia, one of our most popular past guests, and a good friend. Shane is Ravi’s friend, and one of the most successful basketball players ever, having won championships and awards at the high school, college, and NBA levels.

 

I spent 10 years as a purely quantitative investor, so naturally I was obsessed with data in sports. When I was meeting with prospective investors, Michael Lewis’s book Moneyball—which chronicled the data analytics revolution in baseball—was my go-to analogy to explain what I did… “Moneyball, but for investing.” I used that line for years.

 

I’ve learned firsthand that it’s wise to follow your curiosity, no matter how strange or different it may be. The podcast is my curiosity tour, and years ago it led me to Sam Hinkie—who is himself on the Mt. Rushmore of analytics in sports. Sam introduced me to Ravi. Then Ravi sent me Michael Lewis’ article written about Shane called “The No Stats All-Star.” I highly recommend you read it.

 

All this serendipity around friends, data, investing, and sports gave me an idea: why not ask Ravi to interview Shane? There were so many valuable ideas in the Michael Lewis article, I thought we’d get even more in a real taped interview with someone that knew Shane well, and that’s exactly what happened. Ravi likes the idea of playing for the front of the jersey, not the back. It is hard to imagine someone that lived that more than Shane. Shane shares his story, lessons learned from various coaches, and using data as an advantage. He also explains the four kinds of teams he’s encountered, which I found simple, and memorable.  I hope you enjoy this great conversation, and if you have ideas for other iconic duos we could bring on in a similar format, DM me on Twitter. Thanks to Ravi and Shane for kicking off Thanksgiving week for us all.

 

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 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

 

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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

[00:03:53] - [First question] - What people measure in basketball, what matters when it comes to winning, and why he was called a replaceable cog in the No-Stats All-Star

[00:08:38] - Some of the plays that impact the overall points during a basketball game

[00:11:44] - The role that preparation and understanding game analytics plays in the ability to do something different and succeed at it

[00:14:33] - The power of curiosity and obsessing over details

[00:16:16] - Embracing his role and how being a role player applies to life outside of the court

[00:20:47] - Where his obsession for winning and being a good team mate comes from 

[00:23:23] - Some of the things great leaders and coaches did to inspire him 

[00:28:51] - An overview of the four types of teams and fundamental aspects of them

[00:34:50] - What a person can do to elevate their team and make it a winning one 

[00:37:43] - Antifragility and the letter Shane wrote for Ravi when Amazon bought Whole Foods

[00:41:08] - Riding the thin line between winning a championship and being irrelevant 

[00:44:56] - How to get everyone rallied around a long-term shared mission effectively  

[00:46:48] - Finding a No-Stats All-Star in a company and what to look for in one

[00:52:34] - The kindest thing anyone has ever done for him

Nov 15, 2022

My guest today is Parker Conrad, co-founder and CEO of Rippling. I wanted to speak to Parker because he is building Rippling in a way that we don’t come across often. Rather than focus narrowly on one product, he is building a suite of interrelated products simultaneously to carry out the functions of HR, Finance, and IT for companies. He calls it a compound company and we discuss the idea, as well as some of his other non-traditional theories, in detail. Please enjoy this conversation with Parker Conrad.

 

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 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

 

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This 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

[00:02:36] - [First question] - Overview of what a compound startup is 

[00:06:32] - What he’s learned about picking customers effectively 

[00:08:48] - Key chapters when it comes to building a compound startup 

[00:13:48] - What great looks like at the base level infrastructure of employee data

[00:20:15] - His overall philosophy on product development writ large 

[00:25:09] - His role as a capital allocator and distributing resources to his teams

[00:27:19] - The amount of products they offer and whether or not there’s a tradeoff between time, cost, and quality when building software

[00:31:36] - Possibly incorporating an app-like store on top of their existing infrastructure 

[00:34:43] - Speed and the kinds of people that can sustain it for long periods of time

[00:36:30] - What motivates him on a personal level and harnessing motivation in general

[00:42:31] - Whether or not there’s an end to feeling hurt by false public perceptions when building in public

[00:44:12] - The intersection of leadership and communication inside of a business and what he’s learned about great communication 

[00:48:00] - The paradox of how focusing on non-scalable actions perpetuates growth and productivity and his views on productivity-per-person

[00:50:36] - The best example of a moment that required the most grit and perseverance while building his company 

[00:52:28] - How to successfully get former founders to come work for him 

[00:54:47] - What good private equity investors do 

[00:58:31] - The kindest thing anyone has ever done for him

Nov 8, 2022

My guest today is Bob Elliott, the CEO and CIO of Unlimited, which creates low-cost index ETFs for alternative investment strategies. Prior to co-founding Unlimited, Bob was a senior investment executive at Bridgewater Associates where he served on their investment committee and led Ray Dalio’s personal research team for a decade. His breadth and depth of experience makes him a great person to assess the current macro landscape. We discuss the relationship between rates, inflation, and asset classes, Bob's approach to identifying data with the most signal, and finish with his view on quantitative strategies in private markets. Please enjoy this great discussion with Bob Elliott.

 

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 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

 

-----

 

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

[00:02:45] - [First question] - The Economic Organization of a POW Camp and key lessons one can learn from the paper

[00:07:22] - The way that supply and demand clears a price and how that plays into his thinking about investing across asset classes 

[00:09:58] - Whether or not he has a generalized investing worldview or framework

[00:11:46] - Deciding on what data is signal and matters most when analyzing markets 

[00:15:46] - A crash course on easy money and tight money regimes and the implications of both in a macro environment 

[00:20:28] - The rise and role of inflation and what should be done about it

[00:24:00] - What the next couple of years will look like if we draw lessons from history

[00:30:12] - Why gold could ever belong in someone's portfolio when it doesn’t produce or yield anything back to the investor 

[00:35:08] - Supply and demand constraints and the state of the housing market today 

[00:40:42] - What might happen in future labor markets given our current macro environment

[00:46:27] - Currencies, energy, geopolitics, and what he’s most focused on globally

[00:52:19] - What movements in the charts are worrying him the most 

[00:56:04] - The original “All Weather” portfolio and what one would look like if he built it today

[01:02:05] - How his career has taught him to find talented individuals who might deliver alpha

[01:07:19] - Lessons learned from early-stage and venture investing and thoughts on that world now

[01:12:41] - Why there hasn’t been an iconic early-stage technology investing firm driven by systematic strategies

[01:16:10] - The kindest thing anyone has ever done for him 

Nov 1, 2022

My guest today is Kirsten Green, founder and managing partner at Forerunner Ventures. Kirsten launched Forerunner in 2012 and has built it into a leading consumer-focused venture firm with early investments in consumer brands like Dollar Shave Club, Bonobos, Faire, and Warby Parker. Our conversation is an exploration of consumer behavior and how to invest behind change in our society. We also discuss frameworks for identifying brands early, how to build deal flow, and the shift in power between buyers and sellers. Please enjoy my conversation with Kirsten Green.

 

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 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

 

-----

 

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

[00:02:35] - [First question] - The insights gleaned from studying consumers in the modern era

[00:07:02] - Whether or not the shift in consumer behavior is similar to a platform shift like mobile

[00:09:58] - Which of her hypothesis going into the research was proven most wrong

[00:11:31] - The leading persona archetype that drives consumer spending 

[00:13:58] - Thoughts about her investing focus after doing all of this research 

[00:16:23] - How much the digital world is good and bad for community

[00:18:50] - Positive and negative impacts digital access has on children

[00:21:17] - The investing criteria that she and her firm have developed for founders and business models they find desirable 

[00:29:20] - An example of the middle of the spectrum between tailwinds and headwinds that may result in them passing on a business

[00:32:00] - The beachhead problem for entry points, encouraging good focus and entry point selection, and who’s done it well 

[00:35:33] - The history of the consumer of how they buy and sell and where the shifts in power have been 

[00:39:47] - Other interesting trends she’s seeing in the seller empowerment era

[00:43:35] - How different her investing models are for linear product businesses

[00:46:45] - Frameworks she’s developed for evaluating a brand early on 

[00:49:57] - The most defining moment in Forerunner’s history and the hardest lesson she’s had to learn 

[00:53:13] - Ways she’s fostered and mentored young investors at Forerunner 

[00:54:04] - What the most underappreciated thing is today about the consumer

[00:54:50] - User and customer development strategies that work well for early stage products

[00:56:26] - Three businesses young investors should study to educate themselves on great consumer businesses; Shoe Dog

[00:59:49] - Where they find the companies Forerunner tends to invest in, and how to build and effective deal flow pipeline 

[01:05:07] - The kindest thing anyone has ever done for her

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.

 

-----

 

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.

 

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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

 

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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

[00:02:58] - [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.

 

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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. 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

Sep 27, 2022

My guests today are Julio Vasconcellos and Mate Pencz, who are partners at Canary and Atlantico, leading early-stage investment firms in Latin America. They’re also both successful entrepreneurs. Mate is the co-founder and CEO of Brazilian real estate unicorn, Loft. Julio was Facebook’s first country lead for Brazil, an entrepreneur in residence at Benchmark, and the former founder of Peixe Urbano which sold to Baidu. This conversation was a great opportunity to dive into the state of investing and business in Latin America today, what it looks like on the ground, and cover the most interesting findings from Atlantico's annual report on Digital Transformation in the region. Please enjoy my conversation with Julio and Mate.

 

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 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

 

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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

[00:02:39] - [First question] - A broad perspective on what is interesting in Latin American investing today - Latin America Digital Report 2022

[00:05:15] - What makes up the existing 1.5% tech penetration index in Lat Am

[00:06:11] - Florian Hagenbuch, Mate Pencz - Everything Will be Bought Online (Loft); David Velez - Building the Branchless Network (Nubank); How important it is to parse by country when it comes to building businesses in LatAm 

[00:08:31] - Overview of LatAm as a microcosm of fintech innovation happening really fast and what is most exciting in that sphere 

[00:12:28] - Why the adoption of PIX was so successful and how it maps onto the banking system

[00:14:27] - What PIX’s widespread adoption will enable for the coming wave of entrepreneurs 

[00:18:30] - Demographics, GDP, growth rates, and inequality in LatAm

[00:22:30] - Shifting to remote work and how it’ll affect LatAm workers and talent

[00:25:25] - Macro tailwinds that matter when it comes to returns in these markes

[00:30:06] - What it feels like for an entrepreneur today compared to when Loft launched 

[00:32:36] - Deeper themes and what needs to be unlocked for LatAm’s tech sector to look more like the US or China with big tech giants 

[00:37:04] - The opportunity set in developing a software that serves small and medium businesses in LatAm

[00:40:12] - Sources of available funding for venture and private equity  

[00:42:54] - What valuations look like and whether or not there’s an entry multiple discount

[00:45:12] - Seeking evidence that crypto is used in more valuable ways in emerging markets 

[00:48:00] - Areas where LatAm is operating in a future state more so than elsewhere

[00:50:28] - What the right amount of global firm participation in capital partnerships looks like

[00:52:38] - Big standout lessons from their operating days 

[00:55:53] - What is most exciting and concerning about their investing style and investing writ large in LatAm 

[00:58:51] - The kindest thing anyone has ever done for Julio

Sep 20, 2022

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.

 

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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

 

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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

Sep 15, 2022

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.

 

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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.

 

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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 acquire crypto

Sep 13, 2022

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.

 

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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

 

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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

Sep 6, 2022

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.

 

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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

 

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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

[00:02:31] - [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

[01:02:41] - The most genius game pattern he’s ever played

[01:04:44] - What attributes will define the great game investors in the coming decades

[01:06:59] - How much his experience lends itself to investing in other sectors

[01:11:07] - The kindest thing anyone has ever done for him

Aug 30, 2022

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.

 

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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. 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.

 

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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

[00:03:01] - [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 process is often art 

[01:08:10] - Who his idols are in podcasting specifically 

[01:14:55] - Major aspects of people he’s studied that haven’t been discussed yet

[01:19:55] - The kindest thing anyone has ever done for him

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