Invest Like the Best with Patrick O'Shaughnessy cover image

Invest Like the Best with Patrick O'Shaughnessy

Latest episodes

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Dec 23, 2021 • 1h 9min

Nick Saltarelli - One Foot in Front of the Other - [Founder’s Field Guide, EP. 54]

My guest today is Nick Saltarelli, co-founder of the functional chocolate bar business, Mid-Day Squares. Nick started the company with his wife and brother-in-law a few years ago to build on a simple idea: if the big chocolate bar brands were to start today, what would they look like?   In our conversation, we discuss the importance of Mid-Day Squares’ $100 million revenue target, what’s wrong with the CPG industry today, and how to keep a long-term mindset while making the most of every day. Please enjoy this unique conversation with Nick Saltarelli.   For the full show notes, transcript, and links to mentioned content, check out the episode page here.   -----   This episode is brought to you by Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs, so you can focus on what matters most—building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders.    -----   Founder's Field Guide is a property of Colossus, LLC. For more episodes of Founder's Field Guide, 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: @patrick_oshag | @JoinColossus   Show Notes [00:02:01] - [First question] - What Mid-Day Squares is and how he started the business [00:04:48] - Why they’re so publicly open about their company’s goals [00:09:05] - Major lessons he learned from his father’s early passing and being around very successful entrepreneurs at a young age  [00:16:51] - What long term thinking unlocks for him in short term progress [00:21:05] - Becoming unexpectedly close and learning from Rory Olson  [00:25:44] - What Rory taught him about deal-making [00:28:35] - Lessons from Rory about raising capital [00:33:25] - Opportunities in a seemingly oversaturated market like chocolate [00:42:46] - An example of doing something contrarian that worked out [00:47:11] - Their unique approach to marketing Mid-Day Squares [00:57:33] - Lessons learned about building a manufacturing operation after years in China [01:02:35] - What we can expect from Mid-Day Squares in the near future [01:06:59] - The kindest thing anyone has ever done for him [01:08:05] - Mid-Day Squares Uncensored Podcast
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Dec 21, 2021 • 1h 3min

Jenny Johnson - Seven Decades of Investing Expertise - [Invest Like the Best, EP. 256]

My guest today is Jenny Johnson, President and CEO of one of the world’s largest asset managers, Franklin Templeton. Jenny joined the business in 1988 and has worked in the organization ever since. In early 2020 she became CEO of Franklin, which now manages some $1.5 trillion. I should, of course, note that I met Jenny as our two firms explored a partnership, which we cemented 3 months ago when we announced that Franklin Templeton would be acquiring O'Shaughnessy Asset Management. During our conversation, we discuss Jenny’s thoughts on leadership, how she manages the needle-moving problem that afflicts many large companies, and the ways in which she sees private markets becoming more accessible to retail investors in the future. Please enjoy this great conversation with Jenny Johnson. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.-----Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes[00:03:19] - [First question] - The four P’s of leadership and what she thinks are the most important roles of a CEO [00:06:00] - The difficulty of finding and recruiting great people and keeping them invested [00:07:18] - Things she looks for in her senior leadership team[00:07:59] - Knowing when to be more or less involved as a leader[00:09:30] - Her takeaways from working in a family-owned business[00:11:20] - Advice she’d give to families who are building businesses together[00:12:06] - Thoughts on the role technology will play in the asset management industry[00:16:13] - Costs and frictions that blockchains could alleviate[00:18:17] - General views on disruption and considering ones position when thinking about the future[00:20:09] - Knowing when to start a project internally or acquire an existing project[00:23:10] - The hardest things about effective M&A decisions[00:23:42] - Overseeing a hybrid model of singular focus between multiple investment groups[00:28:26] - The pros and cons of active management against passive adoption[00:31:15] - Costs and fees in the industry and how they might change in the future [00:33:04] - Talking to clients when they don’t have one specific view on strategy[00:36:10] - Formative experiences in her career that has shaped her worldview[00:38:34] - Managing emotions through seemingly chaotic situations[00:39:13] - The impacts on psychology when being a top performer and an average one[00:41:15] - Managing and adapting strategy when faced with highs and lows [00:42:55] - Acquiring alternative managers and defining what alternative assets are[00:46:26] - Relevant trends on how capital is pooled and their client base over time[00:47:52] - What is under-discussed in the world of asset management today writ large[00:49:01] - Other leaders she’s met or knows that have had her in awe[00:50:30] - What about Cathie Wood has made her story and approach so successful[00:51:38] - How she runs a great board meeting and ways to improve meetings themselves [00:53:34] - Lessons learned about time management as the leader of a public company[00:54:52] - What purpose means to her [00:56:18] - Ways we can incentivize young and new people to start investing[00:59:10] - Her favorite things that her dad has taught her and how she’d describe him [01:00:57] - What has her most excited about the future  [01:01:34] - The kindest thing that anyone has ever done for her
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Dec 14, 2021 • 1h 17min

Doug Colkitt - The Evolution of Markets - [Invest Like the Best, EP. 255]

My guest today is Doug Colkitt. Doug has spent his career searching for and trading inefficient markets, first at Citadel’s high-frequency trading group, then for himself, and then as an operator building CrocSwap - a decentralized exchange or DEX designed to bring modern functionality to crypto markets, which is closer to what large traders have come to expect from a modern electronic market like the NASDAQ.  My interest in market infrastructure has continued to grow since my great conversation with FTX founder Sam Bankman-Fried. So my conversation with Doug covers the evolution of market and trading infrastructure. We unpack the trading stack as it exists today, dive into DeFi’s innovations, and explore the new category of single contract DEXs that Doug is creating. After learning so much from Doug about how markets function and how crypto markets should function, I became an investor in his new business via my venture capital firm Positive Sum. Please enjoy this great conversation with Doug Colkitt. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. -----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[00:03:31] - [First question] - Doug’s career and history working with markets[00:08:55] - Defining what a trading stack is [00:13:41] - How HFT firms are such reliable money-making models[00:16:27] - What’s at the cutting edge of traditional markets that provides an edge[00:18:45] - The mechanical parts of infrastructure involved in building an exchange[00:21:00] - Classes of data that matter for operating an exchange[00:22:11] - Capacity and what good returns are as an HFT firm[00:28:45] - Overview of the mechanics of an AMM[00:31:53] - Earning a yield as a liquidity provider[00:33:59] - Other ways to think about AMMs and liquidity providers[00:36:42] - Key players in the AMM space and the evolution of them[00:41:20] - How asset holders can approach DEX tools and be liquidity providers[00:42:55] - The function of an exchange’s native token[00:45:25] - Token distribution and how to earn them without buying them[00:48:31] - How you receive payment for providing liquidity[00:51:31] - What CrocSwap will do and what a single contract DEX unlocks[00:57:36] - How CrocSwap is able to do this when other exchanges can’t[00:59:27] - What single contracts will improve for users [01:00:43] - The impact CrocSwap will have for all participants writ large[01:02:28] - Whether or not CrocSwap will cultivate an ecosystem[01:03:30] - What’s next for CrocSwap in the near future[01:04:58] - The promise of DeFi and the future of blockchain technology[01:07:04] - Whether or not DeFi is a threat to centralized exchanges[01:09:52] - Defining what MEV is and why it’s important for DeFi[01:13:04] - Missing pieces in the DeFi world and how we can address them[01:15:24] - The kindest thing anyone has ever done for him
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Dec 7, 2021 • 1h 16min

Bill Gurley and Philip Rosedale - Back to the Future - [Invest Like the Best, EP. 254]

My guests today are Philip Rosedale and Bill Gurley. Philip created Second Life in the early 2000s and helped build it into the largest virtual 3D world ever created at the time. Frequent listeners will recognize Bill, who was an investor in Second Life via Benchmark Capital. During the conversation, we cover the fascinating story of Second Life and the billion-dollar economy that persists through to this day. Bill and Phillip share their key learnings from the experience, including the importance of usability, their views of the current metaverse opportunity, and what excites them most about the current focus on virtual realities. If you’re curious about what the metaverse might become, these two experts have seen much of this already and are kind to share their lessons with us. Please enjoy my conversation with Phillip and Bill. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. -----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[00:03:22] - [First question] - The origin story of Second Life and why they created it[00:05:38] - How many people were playing Second Life at its peak, the in-game economy and its growth trajectory[00:06:49] - The interface between the in-game currency and its function for players[00:10:53] - An example of early entrepreneurship and user-created IP in Second Life[00:12:13] - Was technology a rate limiter to success in such an early version of the metaverse?[00:14:35] - What was most exciting about creating it and it’s early-stage potential[00:18:23] - Why Unity isn’t more adopted by creators and players like Minecraft[00:24:42] - Defining what the metaverse means to each of them today [00:28:50] - What Discord has taught them about aggregating people digitally[00:33:02] - Simultaneously crossing the digital chasm and the uncanny valley [00:38:16] - Key differences between games and platforms and the role of purpose[00:42:04] - Why cryptocurrencies and blockchains haven’t produced experiences akin to the virtual Travis Scott concert[00:47:13] - Why removing friction and centralizing financial structures can help growth and thoughts on play to earn gaming and user spending[00:53:27] - Digital asset ownership and digital trustless exchanges in the metaverse[00:57:30] - Pros and cons of today’s speculative digital asset valuations[01:01:05] - Interesting pockets of opportunity that could benefit the metaverse ecosystem[01:04:28] - How they’d build and construct an ETF with metaverse exposure[01:07:18] - Thoughts on AR and VR and which holds more promise for public adoption [01:08:02] - Surprising findings about the role audio plays in digital worlds  [01:10:23] - What they’re watching most closely in this emergent sector[01:11:29] - Limitations of visual and sonic barriers when recreating real-world interactions [01:12:42] - The kindest things anyone has ever done for them 
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Nov 30, 2021 • 53min

Francis Davidson - Design-led Hospitality - [Invest Like the Best, EP.253]

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.-----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 
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Nov 23, 2021 • 1h 4min

Niraj Shah - Developing Every Skill - [Invest Like the Best, EP. 252]

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.   -----   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 [00:02:50] - [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
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Nov 18, 2021 • 52min

Bored Ape Yacht Club -  [Web3 Breakdowns, EP. 1]

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. ----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.----- 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
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Nov 16, 2021 • 50min

Will Marshall - Indexing the Earth - [Invest Like the Best, EP. 251]

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. ------ 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[00:13:35] - 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
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Nov 5, 2021 • 1h 8min

Roelof Botha - Sequoia’s Crucible Moment - [Invest Like the Best, EP. 250]

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. ------ 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[00:13:11] - 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 [00:49:26] - 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
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Nov 2, 2021 • 1h 13min

Sarah Friar - Building the Local Graph - [Invest Like the Best, EP. 249]

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.------ 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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