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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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Now displaying: 2023
Apr 11, 2023

My guests today are Scott Davis and Rob Wertheimer. Scott and Rob head up Melius Research and are the authors of a great book called Lessons from the Titans. The book explains what the industrial giants of old can teach the new generation of high-growth businesses about how to survive and deliver shareholder value over multiple decades. Drawing on their experience as industrials analysts, they present case studies on businesses like Danaher, Roper, Honeywell, Boeing and GE to reveal both what does and doesn’t work when it comes to capital allocation and business strategy as a company enters a more mature phase in its lifecycle. Please enjoy my conversation with Scott and Rob.

 

Read Lessons from the Titans

Listen to Founders Podcast

Founders Episode 136 - Estee Lauder

Founders Episode 288 - Ralph Lauren

 

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

 

-----

 

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

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

(00:03:20) - (First question) - The intersection between the current tech sector drawdown and the historical track record of industrial titans 

(00:07:10) - The most common ways they see companies start to fail and the types of errors they commit 

(00:11:01) - The best historical examples of companies that have gone from non-operational excellence to operational excellence 

(00:15:04) - Teaching the value of a business system and installing one for longevity 

(00:24:06) - Questions they’d ask and points of evaluation to uncover the health of a business

(00:31:19) - Thinking about sustainable value creation in a lower growth environment 

(00:37:04) - Lessons from operating leverage and the rental industry 

(00:39:11) - Ways industrial companies have handled growth CapEx well and badly 

(00:43:52) - The line between discovering the future in a lab versus major pivots in reality while trying to solve today’s problems 

(00:49:37) - How the best managers nurture a great shareholder base 

(00:55:35) - Lessons to learn about business model transitions   

(01:00:13) - Further important messages from their book that businesses would benefit from

(01:04:30) - The kindest things anyone has ever done for them

Apr 4, 2023

Today’s episode is a little different. Rather than share a new conversation, I have put together a few of my favourites from the past six and a half years of doing this show. I often listen back to these for inspiration, energy, and their timeless ideas on life and investing. Internally, we call these forever episodes because they’ll likely still be as relevant and popular a decade from now as they were when they first aired.

The first conversation you’ll hear is with Sam Hinkie. Sam worked for more than a decade in the NBA, helping pioneer the use of data and analytics, originally with the Houston Rockets and finishing off as the GM of the Philadelphia 76ers. In life after basketball, Sam launched his own venture capital fund, 87 Capital. Sam's approach to everything is about finding great people, and he has taught me more about that topic than just about anybody else.

The second discussion is with Boyd Varty. My original conversation with Boyd, way back in 2017, had a huge impact on me and I’m sure you’ll hear why. He grew up in the South African wilderness, living amongst and tracking wild leopards. He talks about the art of tracking and how the same strategy for pursuing animals in the wild can be applied to all aspects of our lives. Rather than following well-trodden paths, we should all explore and look for original experiences. He might still have the best answer I’ve ever heard on the podcast.

The last conversation you’ll hear is with Charlie Songhurst. Charlie is the former head of strategy at Microsoft, and a prolific investor having personally invested in nearly 500 companies through his career. Within one minute of meeting Charlie, you can tell that his mind is sparkling with ideas and curiosity. It's no wonder he was among the most commonly requested guests. Charlie would always come up when I asked top investors and CEOs who I should have on the show and he often still comes up as people’s favourite guest.

Sam, Boyd, and Charlie are all exceptional in their own way and I hope you enjoy these condensed versions of our conversations. You’ll find links to the full, original episodes in the shownotes. Enjoy and share them with friends and loved ones who you think will benefit from these original thinkers. 

 

Sam Hinkie - Find Your People

Boyd Varty - The Art of Tracking

Charlie Songhurst - Lessons from Investing in 483 Companies 

 

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



-----

 

This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. 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

(00:04:40) - (Sam Hinkie) - His focus on quality people and talent as a key driver for success

(00:05:55) - The most amazing thing he’s seen from someone he has worked with, early on in the partnership

(00:07:59) - The different leadership styles he has absorbed through his career

(00:09:51) - His interest in finding “digital breadcrumbs” on his pursuit of knowing a person

(00:13:18) - The impactful story of meeting the assistant GM of the Houston Rockets

(00:17:22) - Strategies he has developed to avoid transactional people

(00:18:19) - The move he made that most factored in to him getting the GM position

(00:19:22) - How he shapes his career and optimizes from an investment perspective

(00:24:06) - The strangest things he has come across in early-stage investing

(00:25:47) - How listeners can use the proverbial bread crumbs to enable serendipity and prosperity

(00:29:47) - (Boyd Varty) - His childhood and his dad’s black mamba story

(00:33:04) - His early experiences with tracking wildlife and how it applies to investing

(00:38:32) - What a full day of tracking looks like, and his Track Your Life retreat program

(00:44:46) - What can be learned about life goals and paths from the experience of tracking

(00:47:59) - The influence of culture on decision-making and goal-setting

(00:50:39) - His concept of “the ordering of chaos on behalf of others” and its impact on life purpose as it relates to the so-called wild self

(00:52:13) - How his theories stand up to common objections from skeptics

(00:54:41) - The importance of moving towards the unknown to start approaching goals

(00:57:15) - His most memorable tracking experience

(01:08:43) - The kindest thing anyone has ever done for him

(01:12:40) - (Charlie Songhurst) - His interest in studying people’s virtues and vices

(01:15:10) - His diverse career highlights

(01:16:29) - His analysis of why startups succeed or fail

(01:21:21) - What founders can learn to enable and maintain productivity in their company

(01:25:21) - Nature versus nurture as it applies to adept founders, and the controversial “alien founder” concept

(01:30:10) - The importance of good recruiting from an early stage

(01:33:32) - How founders can make their companies attractive to prospective talent

(01:35:53) - Why he is interested in investing in highly boring and highly complex ideas





Mar 31, 2023

Hello everyone. A few days ago, we discussed what we call forever episodes, which are the few episodes of our show that we think will be as popular a decade from now as they are today. When I re-listened to this episode with David Senra, I left wildly energized and wanting to share that feeling. So we are re-releasing it today for anyone who missed it the first time or hadn't yet discovered Invest Like the Best. Please share it with your friends and loved ones as I think anyone will benefit from David's perspective and enthusiasm. Have a great weekend and we'll be back with more next week.

David Senra 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. Please enjoy this great conversation with David Senra.

 

Follow Founders in your podcast player here.

 

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, 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

[00:03:01] - [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

 

Mar 28, 2023

My guest today is David Einhorn. David is the President of Greenlight Capital, a long-short hedge fund that he co-founded in 1996. He is a prominent value investor with a reputation for rigorous security analysis. In 2002, he revealed a short position in Allied Capital, which was ultimately proven correct and similarly in early 2008, he told the Sohn Conference he was short Lehman Brothers. Over his near three decades managing money at Greenlight, he has delivered impressive returns but it has not been without challenge. Our conversation covers both the highs and the lows, his views on the current banking issues, and how he has evolved as an investor. I’m on the planning committee for this year's Sohn conference where David will be featured with others like Stan Druckenmiller, OpenAI CEO Sam Altman, Stripe CEO Patrick Collison, and Bridgewater CIO Karen Karniol-Tambour. If you’ve enjoyed Invest Like the Best and are willing to contribute to a great cause—Memorial Sloan Kettering Cancer Center—I’d deeply appreciate you buying a ticket at the link available in the show notes and join us in May for what will be an incredible day of investing and business presentations and interviews. Now, please enjoy my great conversation with David Einhorn.

 

Buy a ticket to The Sohn Conference 2023

Listen to Founders Podcast

Founders Episode 136 - Estee Lauder

Founders Episode 288 - Ralph Lauren

 

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, 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

(00:03:50) - (First question) - Why he is glad he started his fund in 1996 rather than today

(00:05:58) - His view of how companies’ personnel and goals have changed since the 90’s

(00:07:01) - His counter-momentum approach to markets and how he views current trends

(00:11:17) - The jelly-donut theory of monetary policy

(00:14:46) - His outlook on inflation and the Fed from a fiscal perspective

(00:15:45) - Commodities and other assets that become relevant

(00:16:48) - The evolution of Greenlight’s portfolio and philosophy through history

(00:20:11) - Periods in his career that stand out as the most challenging

(00:25:58) - How tech advances have influenced his core concept of figuring out worth

(00:28:17) - His three-step process to picking investment targets

(00:29:10) - The companies he has learned the most from studying

(00:30:52) - His experience with investing in Apple

(00:33:33) - How he considers the notion of quality in a business

(00:35:05) - His views on shorting, concentration, and holding periods

(00:38:37) - What he learned from a deep dive on airline businesses

(00:40:31) - His perspective on sports franchises as an asset

(00:42:12) - His new interest in poker and how he got so good at it

(00:45:22) - Applying traditional valuation styles to the modern market

(00:47:13) - Cultivating relationships with his limited partner investors and his team

(00:51:06) - The joy and drive that keep him buying and selling

(00:54:26) - His perspectives on the insurance space

(00:57:33) - The health of the economy and financial infrastructure as he understands it

(01:01:51) - How he thinks about housing and the construction industry

(01:03:54) - How AI and other high-tech are affecting his investment decisions

(01:05:28) - Other topics on his mind, from national politics to social psychology

(01:08:22) - The kindest thing anyone has ever done for him

Mar 21, 2023

My guest today is Avi Goldfarb. Avi is a Professor at the University of Toronto’s Rotman School of Management, the Rotman Chair in Artificial Intelligence and Healthcare, as well as the co-author of two bestselling books on AI and its economic impact. His most recent book, Power and Prediction, is probably the best piece of content I have read in explaining how AI may reshape business models, systems, and products. We recorded this before GPT-4’s release last week which, if anything, makes Avi’s ideas on AI’s impact all the more poignant. Please enjoy my conversation with Avi Goldfarb.

 

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

 

-----

 

This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. 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

(00:03:15) - [First question] - His initial reaction to chat GPT when it first launched 

(00:07:08) - Prediction Machines; The impact price has on how much something is used by humans

(00:11:07) - The shift from steam powered factories to electric ones and the transition between the two in regards to systems and application solutions; Power and Prediction

(00:17:06) - Midpoints between a point solution and a systems solution and applications that are being built in the middle of them

(00:19:10) - What application, system, and point solutions feel like today in the world of AI

(00:27:03) - The transition from a world governed by rules to one by decisions  

(00:30:58) - How the power of prediction moves us from a binary to a decimal framework

(00:34:48) - Ways power disruption will occur as we navigate the emerging AI frontier

(00:44:33) - Other functions like personalization that entrepreneurs should think about putting into their products and features

(00:47:18) - How we should be thinking about the generation of information and data 

(00:51:32) - A future where technology either desimates or empowers specific industries

(00:54:16) - What he’s most excited and worried about given the emerging frontier of AI 

(00:55:41) - The kindest thing anyone has ever done for him 

Mar 14, 2023

My guest this week is Auren Hoffman. Auren is the CEO of Safegraph, which curates data on physical locations. He also founded LiveRamp, a public data connectivity business. Auren knows more about data businesses than almost anyone I know and that is the topic of today’s discussion. We look at the business of data from every angle and finish with a fun masterclass on how to host a dinner party. Please enjoy my conversation with Auren Hoffman.

 

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 long-time 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

[00:03:16] - [First question] - His 2x2 matrix for categorizing different types of data businesses

[00:04:59] - An example of what he calls a religion company in his matrix

[00:07:03] - His notion of data currency

[00:08:23] - His definition of a great business

[00:09:46] - An example of a so-called application religion company in his proverbial matrix

[00:11:24] - Co-op and non-profit business models within and outside of the data sphere

[00:13:35] - The truth application quadrant of his matrix

[00:15:00] - The more pure-data-oriented truth category of the matrix

[00:16:18] - How data has exploded in prevalence for the business world as a whole

[00:18:57] - How to think about the end market for data and its demand

[00:21:09] - Characteristics of a good data set and how to identify it

[00:23:14] - Other factors that impact the usability of a data set

[00:24:30] - Optimizing data collection itself

[00:26:30] - The slow growth that’s typical of early-stage data companies

[00:27:27] - Market share considerations for data businesses

[00:28:47] - Brand-building for data companies and how it can supercharge market share

[00:30:03] - Common struggles for data entrepreneurs

[00:31:55] - How he found a big problem that he could feasibly solve with data

[00:34:01] - The genesis of his business; SafeGraph

[00:35:15] - Progress in privacy protocols for gathering and mobilizing people’s data

[00:37:08] - The power of self-maintained and user-maintained databases

[00:38:34] - The kinds of data that SafeGraph gathers and how he foresees it expanding

[00:40:16] - Typical customers and use cases for SafeGraph’s data

[00:41:08] - How SafeGraph and other companies protect against data theft

[00:42:12] - Frequency of change as a proxy for the value of a given data set

[00:43:27] - How to optimize the systems of a business to continually gather and maintain accurate databases

[00:45:32] - Categorizing inbound data based on the most important criteria

[00:47:07] - The founder personalities he finds in the data industry

[00:48:36] - The most noteworthy or quintessential data businesses in his opinion

[00:49:53] - Why he feels the data truth quadrant of his matrix is underdeveloped

[00:50:30] - Bloomberg as an important data company to study

[00:51:42] - The importance of transparency in business and in data distribution

[00:53:07] - Failure modes that he sees most commonly in data-based startups

[00:53:53] - Data businesses becoming application businesses and vice-versa

[00:55:29] - Innovations in the join keys and mechanisms that enable data to travel

[00:57:35] - The great dinner parties he’s known for

[00:59:50] - How he makes the dinner parties appeal to introverts

[01:03:11] - Dead people he would most like to have as dinner guests

[01:04:09] - Questions he would ask the most influential religious figures

[01:04:58] - Why he thinks people are generally good and want to be inspired and passionate

[01:06:20] - The kindest thing anyone has ever done for him

Mar 7, 2023

My guest this week is Trae Stephens. Trae is a partner at Founders Fund and co-founder and Executive Chairman of Anduril. Trae’s philosophy can be boiled down to finding good quests, which has led him to investing in businesses that work closely with the government on societally important issues. Clearly, that extends to co-founding Anduril and I would highly recommend listening to my Business Breakdowns episode on Anduril if you haven’t already. In this conversation, we discuss the importance of lobbyists, why the high-tech defense firms of the past became stale, and how he hunts for disagreeableness in founders. Please enjoy my conversation with Trae Stephens.

 

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

 

Listen to Founders Podcast

Founders Episode 136 - Estee Lauder

Founders Episode 288 - Ralph Lauren

 

-----

 

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

[00:03:17] - [First question] - Why Trae thinks most high-margin businesses are bad for society

[00:04:28] - What would he change to impact energy technology most if he were in charge

[00:06:18] - His investing focus on dynamism and mission-driven tech companies

[00:09:42] - Analyzing why relatively few people strive to make society-level advancements

[00:11:35] - What he’s done as a parent to enable his kids to develop passions

[00:12:41] - The most noteworthy adventures in his career

[00:14:41] - Founding Anduril and what it taught him about the tech industry

[00:18:40] - The cutting-edge of defense technologies today

[00:21:29] - What Shyam Sankar of Palantir taught him about defense tech

[00:23:34] - Why some of the biggest defense tech companies have stopped innovating

[00:28:29] - What he and Anduril have learned about sales and scaling in the public sector

[00:32:12] - Where lobbyists and decision makers play in to defense tech business models

[00:35:22] - His take on Peter Thiel’s notion that competition should be avoided

[00:38:24] - The importance of being psychologically disagreeable when building a start-up

[00:39:54] - The origin story that stands out the most from companies he has interviewed

[00:41:12] - How he developed an investor mindset on his unorthodox path to the venture world

[00:43:57] - What he has learned from playing supporting roles and aligning with great leaders

[00:46:11] - Important but uncommon lessons about entrepreneurship

[00:48:21] - Venture investing lessons he’s learned from Lauren Gross

[00:50:00] - His first VR project and aspirations for the future of VR

[00:54:50] - The role of religion and spirituality in his business philosophies

[00:59:13] - Why he tries to capitalize on morality as opposed to sin

[01:03:57] - The kindest thing anyone has ever done for him

Feb 28, 2023

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

 

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

 

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

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Feb 21, 2023

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

 

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

 

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

 

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

 

Listen to Founders podcast.

 

-----

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Feb 14, 2023

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

 

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

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Feb 7, 2023

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

 

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

 

Listen to Founders podcast

 

Founders Episode #136 A Success Story: Estee Lauder 

 

Founders Episode #288 Ralph Lauren


Invest Like the Best with David Senra: Passion & Pain

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:02:44] - [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.

 

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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.

 

-----

 

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.

 

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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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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

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