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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: November, 2021
Nov 30, 2021

My guest today is Francis Davidson, founder and CEO of the hospitality brand Sonder. Francis launched Sonder in 2013 as an alternative to traditional hotels and rentals with a specific focus on technology and design. During our conversation, we discuss where Sonder fits into the hospitality ecosystem and why design is so key to their offering. We also touch on Francis’s unique views around customer-centric focus, the nuances of hiring a team, and how they approach decision-making. Please enjoy my conversation with Francis Davidson.

 

For the full show notes, transcript, and links to the best content to learn more, 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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

 

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At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/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

[00:02:38] - [First question] - Thoughts on the obligation of a business to deliver the best possible customer experience

[00:03:43] - Making a decision that actively went against improving the customer experience

[00:06:00] - What Sonder is and the key insight that led to building the business

[00:08:43] - Ways they cut down costs by leveraging technology available today

[00:10:44] - The economic model of the business and where it differs most from other hotels

[00:12:15] - The journey of $100 coming in to Sonder and working through the company

[00:13:20] - How the building or asset owner is integrated into the business model

[00:14:18] - Network density and how he thinks about it when it comes to scaling Sonder

[00:16:18] - His philosophy on design and why he thinks it matters in hospitality

[00:18:05] - What you can overspend on and underspend on to keep a guest happy

[00:21:05] - Making decisions on building in house or partnering to provide a new solution

[00:22:29] - Do property owners dress up their own hotels or are there guidelines and retailers

[00:23:51] - Lessons learned from working with overseas manufacturers

[00:24:44] - The key levers that will drive the growth of Sonder

[00:26:59] - What a typical occupancy rate is for them versus other hospitality options

[00:28:23] - Category creation and design that influence and change how people behave

[00:29:45] - Qualities of a new market and what drives success in attacking it

[00:31:15] - His contrarian viewpoint on building a business and talent density

[00:33:40] - The features of his job’s product and the interview process

[00:36:21] - Does everyone at a company need to be an A player?

[00:38:00] - His philosophy on team culture and developing synchronicity

[00:41:01] - Ways to build strategic competitive advantage inside of Sonder

[00:43:22] - What the most successful version of Sonder will look like ten years from now

[00:45:16] - New features and tech improvements that are coming soon he’s excited about

[00:46:48] - Trends in hospitality that have been accelerated and changed by COVID

[00:48:36] - Growing changes in the glamping and nature-forward guest experiences

[00:51:04] - The kindest thing that anyone has ever done for him 

Nov 23, 2021

My guest today is Niraj Shah, the CEO and co-founder of Wayfair. Wayfair started life in 2002 as a collection of independent websites selling category-specific home furniture but became a one-stop-shop for the home category in 2011 when, at $500 million in sales, the team consolidated their 240 websites into Wayfair.com. Today, the business offers 22 million products from 16 thousand suppliers to more than 30 million customers.

 

During our conversation, we discuss how the competitive frontiers in e-commerce have changed, what it was like to build out a proprietary logistics operation, and what makes the home goods market more attractive than other physical goods markets. Please enjoy this great conversation with Niraj Shah.

 

For the full show notes, transcript, and links to the best content to learn more, 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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

 

-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/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

[00:02:50] - [First question] - The global supply chain and its issues today in 2021

[00:05:13] - Why he finds the ocean leg such a problematic area and how to resolve it

[00:07:04] - Overview of the physical goods market around the world

[00:10:50] - The role of magazines and devout subscribers in certain sectors 

[00:11:50] - Are physical goods trends in flux or fairly steady and less geared to change

[00:13:06] - From 240 separate websites into what became Wayfair as we know it today

[00:16:36] - The competitive frontier of eCommerce in its early days and why they won 

[00:18:29] - Expanded logistics control, developing their brand, and becoming Wayfair

[00:21:40] - Aggressively building for the future as a public company with investors involved

[00:27:23] - Key differences between Wayfair, IKEA, Restoration Hardware and others

[00:34:22] - Other areas of interest and drivers of future investment opportunities for Wayfair

[00:38:39] - What excellent marketing means to him and why Netflix does it so well

[00:42:02] - The margin profile of Wayfair and all of its major components 

[00:47:13] - Lessons learned from major mistakes while building the business

[00:49:54] - Company culture and deliberately investing time and money into it

[00:51:50] - Evaluating the importance and success of their adapt and grow philosophy

[00:53:18] - How he would measure his own improvement as a CEO over time

[00:55:17] - Thoughts on the dimension of competition as they scaled

[00:56:57] - The most stressful episode of growing the business and what he learned 

[01:00:16] - What the best outcome for Wayfair would look like in the future

[01:01:38] - The kindest thing anyone has ever done for him

Nov 18, 2021

Today, I am excited to share our newest show, Web3 Breakdowns. Similar to our Business Breakdowns series, Web3 will have it's own dedicated feed so make sure to hit this subscribe link or find it on your preferred podcast player. The first episode of Web3 Breakdowns covers Bored Ape Yacht Club. You will hear from guest, Eric Golden, who will also be coming back to host his own Web3 Breakdowns moving forward. We are sharing this first episode to make sure no one misses this launch. 

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Welcome to our new show, Web3 Breakdowns. We want to be your on ramp into this new decentralized world, and through conversations with builders, creators, and investors, we will do our best to help you understand and navigate this emerging ecosystem.

First up, we are breaking down the NFT project and cultural phenomenon, Bored Ape Yacht Club. To help break down Bored Apes, I am joined by Eric Golden, former Portfolio Manager at Fidelity and current Bored Ape owner. Eric and I start with an overview of the Bored Ape Yacht Club and his path to owning an NFT in the collection. We then use Bored Apes as a lens to understand how NFT projects are not just creating rare art but strong membership communities too. Beyond the cultural differences between NFT communities, it was fascinating to hear how projects are differentiating themselves with IP ownership, roadmaps, and DAOs. Please enjoy this breakdown of the Bored Ape Yacht Club.

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

 

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Coinbase is the only publicly-traded company with experience trading and custodying crypto assets at scale - build a unified investment portfolio with the most trusted name in crypto. Learn more by visiting coinbase.com/prime to get started.

 

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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 | @patrick_oshag | @JoinColossus

 

Show Notes

 

[00:02:30] - [First question] - What the Bored Ape Yacht Club is

[00:03:39] - Motivations for owning a Bored Ape compared to traditional art 

[00:07:46] - The scope of prices, hierarchy, turnover, and trading overview of these NFTs

[00:09:51] - Distribution of rarity and why it matters 

[00:11:29] - How the project roadmap is managed by the member community

[00:16:23] - Who are the members and the key stewards of steering the ship

[00:18:08] - An example of a project where the owners don’t own the IP of their NFT

[00:20:56] - Underlying fundamentals and utility behind owning a Bored Ape 

[00:26:36] - Thoughts on fungible tokens inside of non-fungible projects

[00:29:06] - Ways to think about the value proposition of owning an Ape and an Ape token 

[00:30:36] - Different options for minting NFTs and their pros and cons

[00:34:36] - Literal mechanics of the minting process

[00:36:59] - Smart contract mediating of combining NFTs to generate rare ones

[00:39:20] - Building a bottom up brand and other examples of this trend

[00:41:50] - Are NFTs just gambling, or will they become investable assets like physical art

[00:46:09] - Blockchain infrastructure of the NFT space and whether it’ll stay on Ethereum

[00:48:48] - What makes the Bored Ape Yacht Club so innovative compared to other projects

Nov 16, 2021

My guest today is Will Marshall, the co-founder and CEO of Planet. Will founded Planet in 2010 with a small team of NASA scientists to build a constellation of satellites that would image the entire Earth every day. Since then, Planet has successfully built and deployed 450 satellites into space, which the company is using to create a time series of images for every place on Earth.

 

Our conversation covers the untold space story. How space is going through an internet moment where cost reductions and performance enhancements have led to a seismic shift in what’s possible above our atmosphere, and how that can drastically improve life on Earth through unique datasets like the one Planet is piecing together.

 

Once you listen to Will speak about Planet’s progress and mission, it’s hard to think of a more underappreciated company in business today.

 

Please enjoy this great conversation with Will Marshall.

 

For the full show notes, transcript, and links to the best content to learn more, 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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

 

------

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/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 thoughts on the renaissance of the space industry

[00:05:09] - The earliest days of Planet and why he started the business

[00:09:22] - Unique data units captured by their satellites

[00:11:21] - What might we know in fifteen years using satellite data that we don’t today

[00:13:35] - The real estate of space and interesting angles to consider 

[00:15:59] - How customers interface with Planet and their early use cases

[00:20:57] - Thoughts on the sovereignty of space and the laws that exist currently  

[00:23:43] - Figuring out the dynamics and pricing of Planet’s business model

[00:27:34] - Examples of stress and tensions when working in space

[00:29:08] - The future of privacy and concerns we should have there collectively

[00:30:29] - Five different types of satellites and their functions

[00:31:39] - The most sci-fi potential futures that Planet may unlock someday

[00:32:54] - Indexing the Earth and using data to train machine learning algorithms

[00:34:02] - What he’s learned about Earth that is most surprising

[00:37:12] - Contributing factors to a 70% decline in life on the planet in 40 years

[00:38:35] - Ways that going public might impact Planet’s long term goals

[00:40:23] - The hardware story of building various prototypes of satellites

[00:42:18] - How much is built in house versus outsourced to fabricate their satellites

[00:43:48] - Complimentary space trends that are compounding beyond imagery

[00:45:32] - Whether or not they plan on making their data open-source

[00:47:15] - Democratizing their data and allowing other companies to build on top of it

[00:48:30] - The kindest thing anyone has ever done for him

Nov 5, 2021

My guest today is Roelof Botha, a partner at one of the world’s oldest and most successful venture firms, Sequoia Capital. A few days ago before I sat down with Roelof, he announced Sequoia’s boldest innovation since the firm was founded by Don Valentine in the early 1970s. Going forward, the firm will break from the traditional VC mould of fund cycles and instead restructure around a single, open-ended, permanent structure named The Sequoia Fund.

 

In our conversation, we first discuss the details of this change from all different angles and then dive into Roelof’s career. We talk about what’s changed over the past twenty years, his days at PayPal, what legendary investors he’s worked with have had in common, and what he’s learned from being involved in businesses like Square, YouTube, and Unity.

 

Please enjoy this great conversation with Roelof Botha.

 

For the full show notes, transcript, and links to the best content to learn more, 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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

 

------

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/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

[00:02:53] - [First question] - What led Sequoia to change their structure

[00:05:53] - Parallels between their approach and the problem Square set out to solve

[00:07:36] - The mechanics of the new fund and how it’ll affect their clients

[00:10:42] - How much discretion LPs will have when choosing to participate in sub-funds

[00:13:11] - What the future looks like and how public securities could be a dominant force

[00:15:02] - Benefits and value-unlocks that the new fund offers that weren’t available before

[00:16:55] - Comparing their structure to the current crossover funds we see emerging

[00:18:21] - What alignment looks like in this new structure for LPs

[00:22:02] - Cost of capital, interest rates, and their impacts on rates of return

[00:25:39] - Changes in the industry and founders that he’s noticed

[00:28:56] - What matters to him when meeting with young companies for the first time

[00:31:47] - The importance placed on value creation over value capture in the early days

[00:33:09] - Things that would dissuade him from partnering with a company

[00:34:18] - What the growth and leadership at Square has taught him over the years

[00:35:44] - Things he’s most excited about for payments looking forward

[00:37:34] - How often a company lowering friction with technology appeals to him 

[00:38:38] - Thoughts on Unity and its role in the growing trend of the metaverse

[00:40:28] - Why the open and decentralized nature of the future is so beneficial

[00:42:05] - Lessons learned about content and internet from working with YouTube

[00:44:08] - The landscape of developers today and MongoDB's role in it 

[00:45:24] - Commonalities between companies who have a successful second act

[00:48:16] - Good board members support founders during their pivotal moments

[00:49:26] - Learning to identify and hunt for crucible moments

[00:50:50] - Curiosity is the key ingredient of a great investor

[00:52:05] - What makes for a fantastic investment memo

[00:53:20] - The most memorable investment memo he’s ever read

[00:54:07] - Honing his leadership as his role has changed at Sequoia these past years

[00:55:51] - Thoughts on Sequoia’s brand and the scope of his ambition

[00:58:05] - What he’s most curious about in the world today

[00:58:46] - What technology wants most from people today

[01:01:13] - The difference between an accountant and an actuary's mindset and when each one is appropriate to inhabit

[01:02:38] - Differences between talent and genius 

[01:04:12] - Closing principals about business building he finds important to consider

[01:06:17] - The kindest thing anyone has ever done for him

Nov 2, 2021

My guest today is Sarah Friar, the CEO of Nextdoor, which connects people in local neighborhoods together. Sarah’s CV sparkles with impressive achievements at interesting businesses, and we spend a lot of time in this conversation thinking through what excellence looks like as a CEO, CFO, equity analyst, and board member. The rest of our discussion is focused on Nextdoor and how the soon-to-be public business is fostering connections between people and businesses in their local areas.

 

I do this podcast so I get to meet and learn from people like Sarah. I could have talked to her for hours. I hope you enjoy this great conversation with Sarah Friar as much as I did.

 

For the full show notes, transcript, and links to the best content to learn more, 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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.



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At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/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

[00:03:03] - [First question] - What makes an excellent equity analyst

[00:05:51] - Things Sarah does differently as an operator because she was an investor

[00:08:29] - Key factors that make a great CFO

[00:09:31] - The role of the CFO in regards to capital allocation as a company grows

[00:11:50] - What convinced her to join Salesforce and Square

[00:14:45] - The initial spark and appeal that led her to join Nextdoor

[00:17:35] - Existing problems with ‘community’ and how they approach fixing them

[00:21:36] - Interesting and compelling data points about in-person interactions

[00:23:54] - Network density as a driving factor of product quality

[00:26:43] - What gives Nextdoor a unique angle against some of its existing competitors 

[00:28:51] - Thoughts on platform leakage and user retention

[00:30:57] - Successful strategies for deploying Nextdoor in a new country

[00:35:32] - Having a feed and trying to avoid creating echo chambers

[00:37:04] - Some of the biggest mistakes they’ve made while trying to grow

[00:38:49] - Options for a business model and thoughts on advertising 

[00:43:25] - The importance of scale, advertising, and their relationship dynamic

[00:45:55] - Ways she’s learned to effectively steer the businesses strategy

[00:49:48] - Why she doesn’t like titles 

[00:51:07] - Key levers that will allow Nextdoor to succeed in the future

[00:53:35] - How advertisers evaluate platforms like Nextdoor compared to Google or Facebook

[00:57:19] - What a successful board member looks like and how she’s learned to be one

[00:59:34] - Leading with transparency and empathy

[01:02:00] - An overview of what Ladies Who Launch is and what they do

[01:03:57] - Way to educate our children about finance and encourage financial literacy

[01:07:51] - Making your platforms welcoming and guiding users away from conflict

[01:10:30] - The kindest thing anyone has ever done for her 

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