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Invest Like the Best with Patrick O'Shaughnessy

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at https://joincolossus.com/
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Now displaying: September, 2021
Sep 30, 2021

My guest today is Dave Girouard, co-founder and CEO of Upstart, a lending platform that leverages AI to make loans more accessible and affordable. Dave started in Silicon Valley as a Product Manager at Apple and later spent eight years at Google, where he built their suite of cloud apps. In our discussion, we cover the lessons Dave has learned about building speed into a habit, the intricacies of training an AI model to predict the future, and what it was like to start a fintech business as an outsider. We also discuss the past, present, and future of lending, why Dave and his team have no plans to build a super app and the differences between public and private market investors from a founder’s perspective. One of the tropes you hear these days is that lending has become a customer acquisition tool for FinTechs, but as Dave explains, the market and opportunity set in lending itself should not be underestimated. Please enjoy this great conversation with Dave Girouard.

 

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 Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.

 

See why brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.

 

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This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambitious problem, then Versett is the firm to call. To check them out, visit versett.com/patrick

 

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Founder's Field Guide is a property of Colossus, Inc. 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

[00:02:54] - [First question] - Lessons learned about adopting speed as a habit

[00:05:39] - Knowing which decisions require your attention and are worth it as a CEO

[00:07:00] - What slows down decision-making execution and overcoming it

[00:09:34] - Ways to persuade partners to move as fast as you do

[00:10:44] - One of his most valuable lessons learned from his time at Google

[00:12:20] - The key insight that first lead him to the idea of creating Upstart

[00:15:10] - The early days of learning about the financial lending space

[00:16:49] - Figuring out how to improve on an age-old rigid and regulated system 

[00:18:42] - Credits scores, what drives them, and why they’re suboptimal

[00:20:57] - Overview of building an AI learning model and applying it to loans

[00:23:24] - Surprising findings on predictions and evaluating loan applicants

[00:25:16] - Machine learning algorithms and interwoven programmer bias

[00:26:49] - The role interest rates play in their business model

[00:28:34] - Revenue model and transactions that fund Upstart 

[00:31:43] - Who the typical customer is and their user experience

[00:33:09] - Ways in which they can compound their AI models for other services

[00:35:10] - The biggest hurdle encountered when building Upstart

[00:36:55] - How he’s seen the FinTech space in his area change over time

[00:38:39] - A pie chart on revenue for financial services today

[00:40:24] - Why there are more profits in lending than payments 

[00:41:25] - Major loans types and how they might change in the future

[00:44:12] - Disruptive aspects of the buy now pay later consumer movement

[00:46:09] - How much Upstart could change the future of lending over a decade

[00:48:17] - Inefficiencies of the lending space that still exist today

[00:49:43] - The most important decisions he’s made while building Upstart

[00:51:59] - Things to know when building a business that sells to banks

[00:52:49] - How it feels to interact with hired CEOs versus founder CEOs

[00:55:05] - Thoughts on cryptocurrency and AI writ large

[00:57:00] - Areas that have his attention and get him excited lately in FinTech

[00:58:58] - State of the art AI growth and what lingers over the horizon

[01:00:36] - What he’s learned about being a public market CEO versus a private one

[01:02:38] - Differences between public market and private market investor philosophies

[01:03:53] - Major battle scars from raising capital for Upstart

[01:05:12] - The kindest thing anyone has ever done for him

Sep 28, 2021
My guest today is Jay Hoag, co-founder of TCV. If you look at Jay’s investment track record, it’s a “who’s who” of tech giants with Airbnb, Netflix, Peloton, Zillow, and a list that does not stop there. Needless to say, Jay has a Hall of Fame career. During our conversation, we talk about his own journey founding TCV, what advice he has for visionaries, and why he sees advantages for private to public crossover investors. Jay has such a wealth of experience that is on display throughout this episode. Please enjoy my conversation with Jay Hoag.

 

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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This episode is brought to you by Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com

 

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Invest Like the Best is a property of Colossus, Inc. 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

[00:03:13] - [First question] - Some of his early key formative experiences that shaped his worldview as an investor

[00:06:29] - How much software businesses have changed since he started investing in them

[00:08:28] - The key insight that led him to create TCV

[00:11:36] - Generating returns by swinging less and raising your average

[00:15:06] - Understanding and evaluating a value proposition in its early stages

[00:22:08] - What slightly crazy founders look like and why it’s important for a company

[00:25:47] - Whether or not we’re in the golden age of content already 

[00:28:27] - Why Peloton was rejected so many times before TCV invested in them

[00:32:32] - Things founders often need from him and how he helps them succeed

[00:36:15] - Lessons learned from investing in public markets versus private ones

[00:41:35] - Advice for founders when it comes to conveying their ideas to investors

[00:44:55] - The social dimension of interactive and network building content

[00:46:18] - How important maintaining a focus in the early days is for a new company

[00:48:07] - The most challenging aspect of executing his strategy today

[00:50:48] - One of the most emotionally stressful episodes while launching TCV

[00:53:44] - Supporting your founders during the good and tough times

[00:55:16] - New potential headwinds and tailwinds in the tech space writ large

[00:59:14] - Things people might be overlooking today that could be great opportunities later

[01:02:58] - Whether or not internet companies are threatened by the crypto boom

[01:04:32] - What most has him most excited about the world today

[01:06:20] - Advice for company building in the investing world in general 

[01:09:48] - The kindest thing anyone has ever done for him



Sep 23, 2021

My guest today is Gina Bianchini, founder and CEO of Mighty Networks, which gives creators a platform to start, grow and own their social communities.

 

In our conversation, we cover the differences between leadership and management, the lessons Gina learned building a similar business in the 2000s with Marc Andreessen, and the elements that make up a thriving community. We talk about community design, finding ways to connect like-minded people, why it’s so important to create movement, and what the future may hold for creators.

 

Please enjoy this great conversation with Gina Bianchini.

 

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

 

-----

 

This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.

 

See why brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.

 

-----

 

This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambitious problem, then Versett is the firm to call. To check them out, visit versett.com/patrick

 

-----

 

Founder's Field Guide is a property of Colossus, Inc. 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

[00:02:35] - [First question] - A period in Gina’s career of deep intensity that she learned from

[00:04:28] - Solving ways to preserve her energy as a high performing entrepreneur

[00:08:19] - How much of her day is spent doing things she wants to do 

[00:11:24] - What is unique to leadership that differs from management

[00:14:49] - The insight that led to what eventually became Mighty Networks

[00:27:19] - Enabling features of a community that Mighty Networks offers creators 

[00:31:51] - Key symptoms of a healthy online community

[00:37:35] - Differences between their emerging communities and the power of belonging

[00:41:38] - Turning movement and accomplishment into a software platform

[00:47:32] - Tying passion into purpose and the structure of a movement

[00:50:20] - The biggest potential risks and challenges that Mighty Networks faces

[00:52:56] - The kindest thing anyone has ever done for Gina 

Sep 21, 2021

My guest today is David Fialkow, co-founder of General Catalyst. If you are looking for a dose of fun, charismatic energy from a very unique investor then this is the conversation for you. David has a diverse background not only as an investor but also as a philanthropist and filmmaker. He won an Academy Award for his role as the producer of the 2018 documentary Icarus. During our conversation, David and I dive into what makes a great founder, the importance of storytelling, and the value of effectively convening people within your network. After listening to all of his great stories, I think you’ll see why David has so much fun and success helping founders. Please enjoy my great conversation with David Fialkow.

 

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.

 

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This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick".

 

------

 

Invest Like the Best is a property of Colossus, Inc. 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] - How the process started that led to filming Icarus and becoming a VC 

[00:16:01] - Lessons learned about identifying creativity in potential founders

[00:19:26] - What it looks like when a founder doesn’t clearly love their product 

[00:24:35] - Different aspects of building a successful investment firm

[00:28:22] - Features of Ken Chenault that differentiates him from other CEOs

[00:30:12] - Applicable lessons for the effective convening of people

[00:35:20] - Whether or not he cares about the business model of new companies they back 

[00:40:57] - The story of Icarus

[00:47:24] - What is David drawn to at the moment

[00:51:13] - Key ingredients required to tell a powerful and convincing story

[00:53:16] - The kindest thing anyone has ever done for him

Sep 16, 2021

My guest today is Justin Waldron, co-founder and President of Playco. Justin is a pioneer of the social gaming industry after he co-founded Zynga at age 19, and he has continued to build games ever since. In our conversation, we cover how Justin sees the future of gaming as social platforms evolve, how gaming may be the next tool for content creation, and how Playco has approached aligning incentives for game creators and players. As talk of the metaverse becomes more mainstream, it’s fascinating to hear directly from those around it. I hope you enjoy my conversation with Justin Waldron.

 

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

 

-----

 

This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.

 

See why brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.



-----

 

This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

Founder's Field Guide is a property of Colossus, Inc. 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

[00:02:47] - [First question] - His thoughts on the metaverse and why it’s so interesting

[00:06:07] - The ways hardware and software will shape the future of digital worlds

[00:08:23] - Examples of how these digital experiences might look in the years to come

[00:10:45] - His background, history, and his life before founding Playco

[00:16:31] - Ways content creates human interactions and its role in user retention

[00:18:43] - How successful social media platforms encourage user interaction 

[00:20:51] - Games becoming a way to create content and being a creation tool

[00:23:06] - This history of user-generated content for pre-existing games

[00:27:32] - Defining what instant gaming is and how it’s different from traditional gaming

[00:30:24] - The technological problems and hurdles in creating games that load instantly

[00:34:00] - Parallels between instant gaming and cloud-powered processing

[00:36:43] - What types of games are most desirable for games shared via links

[00:38:58] - The feel of this model working in real-time and the project that’s furthest along

[00:41:37] - Lessons learned about working with and structuring partnerships with social media and content creation giants

[00:45:06] - Ways in which social network platforms are evolving

[00:48:04] - Playco’s business model and smart approaches to generating revenue

[00:50:28] - The role NFTs might play in instant gaming and making crypto mainstream

[00:53:03] - Crypto wallets and building one in house versus using a 3rd party wallet

[00:54:17] - What the best case scenario will look like for Playco in a decade from now

[01:00:44] - Other companies to go check out that leverage and empower individuals 

Sep 14, 2021

Today is a special episode because it marks five years since I released the first episode of Invest Like the Best. Over those years, I’ve learned so much from so many investors and builders, but today’s guest may have taught me the most.

 

Daniel Ek is the CEO and founder of Spotify, and I find him to be one of the most thoughtful business leaders in the world. Daniel is the perfect guest for this special occasion because he exemplifies the curiosity, humility, leadership, and dogged determination that I think characterizes the best investors and operators.

 

In our conversation, we discuss the differences between the world of bits and atoms, how Daniel gets up to speed in challenging new fields, and why Europe might be a sleeping giant about to wake. We then bring the discussion back to Spotify, the evolving creator ecosystem, and Daniel’s frameworks for leading the business into its next chapter of growth.

 

Over the past 5 years, we’ve produced more than 300 of these shows and reached nearly 30 million people. I am deeply thankful to the guests who’ve been willing to share their knowledge with us all and even more thankful to everyone who has taken the time to listen and learn alongside me. This has truly been the greatest pleasure of my career, and I don’t plan on ever stopping this journey.

 

Now, Please enjoy my conversation with a great friend, Daniel Ek.

 

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.

 

------

 

This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick".

 

------

 

Invest Like the Best is a property of Colossus, Inc. 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, and Ben Thompson.

 

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

[00:03:37] - [First question] - Building atoms versus bits and if we’re destined to return to atoms

[00:08:04] - What makes early-stage atoms companies more challenging to build

[00:10:20] - Whether or not we’re starting to see cross-pollinating of infrastructure companies into other sectors

[00:13:00] - His process for learning about new fields when he knows nothing

[00:16:12] - Big and interesting problems that we will need to solve 

[00:19:35] - The nature of healthcare’s technological adoption compared to other sectors

[00:24:13] - Downstream unlocks of collecting and observing big pools of data

[00:30:00] - What he has found effective about taking an idea from 0 to 1 

[00:33:40] - Lessons learned about compounding change and staying patient

[00:37:17] - History of European technology and its unique regional characteristics

[00:42:40] - Cultural and continental traits that may make Europe a technological leader 

[00:45:42] - Characterizing the major lessons learned from his time at Spotify 

[00:50:31] - How artists are changing the ways they connect with their fans via Spotify

[00:55:44] - What he would change about the legacy music industry given today’s tools

[01:00:15] - The influence global exposure has on internet companies and creatives 

[01:03:02] - Interesting observations about the recent explosion of podcast popularity

[01:07:36] - Working with, carrying, spreading, and maintaining Spotify’s sacred source

[01:12:37] - Ways we can improve and sharpen our decision-making skills

Sep 2, 2021

My guest today is Gabby Dizon, co-founder of Yield Guild Games or YGG. In 2020, Gabby and his co-founders built YGG around the growing “play-to-earn” economy within blockchain-based games. Based in the Philippines, YGG effectively backs players - who might not otherwise be able to afford to play - in exchange for a share of their profits. Today, YGG is paying out over a $1mn US dollars a week to players within its community - largely concentrated in their home country of the Philippines.

 

The play-to-earn model has seen its most rapid growth in the popular NFT-based game “Axie Infinity”. Players earn tokens within the game which can be exchanged into local currencies or be used to purchase more digital assets. For a sense of how this market has expanded, Axie Infinity has already reported over $1.5bn in sales over its history- and nearly $900mn over the last 30 days.

 

The speed at which these games and the ecosystems around them are growing is remarkable. In our conversation, Gabby explains YGG’s decentralized structure, the unit economics of their business model, and how he deals with the volatility of crypto assets when trying to build a durable, long-term business. We also discuss the broader metaverse landscape, how it might evolve, what might derail it, and the technicalities of building a token-based, as opposed to equity-based, business.

 

I hope you enjoy this wild conversation with Gabby Dizon.

 

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

 

-----

 

This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.

 

See why brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.

 

-----

 

This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

Founder's Field Guide is a property of Colossus, Inc. 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

[00:03:34] - [First question] - What Yield Guild Games is and what they do

[00:04:30] - The growing popularity of play-to-earn games in the metaverse 

[00:06:07] - Major categories of digital assets that exist today 

[00:08:11] - How players can earn money playing Axie Infinity

[00:10:47] - The business model of YGG and what they offer to players

[00:12:42] - Potential earnings of playing Axie Infinity

[00:15:03] - Possible risks to demand and what the Axie economy could be in a few years

[00:17:54] - Evaluating games that are worth investing in

[00:19:55] - The kinds of things that will be most valuable across games in the future

[00:21:37] - Differences in value between cosmetic and utilitarian in-game purchases

[00:23:04] - Key focuses of YGG over the near future

[00:24:47] - What’s different about labor and capital in the metaverse

[00:27:11] - How tokenomics works and value grows for a DAO

[00:29:02] - Ways DAOs are better or worse than traditional equity tables

[00:30:11] - The state of YGGs economics today

[00:31:16] - The Guild’s player retention and growing their scholars

[00:32:54] - Barriers to entry for building a competitive DAO like YGG

[00:34:14] - What made Gabby so interested in crypto originally

[00:36:38] - His personal journey to crypto games

[00:37:53] - Jobs that may carry over from the real world into the metaverse

[00:39:36] - Companies that will arise focusing solely on in-game item creation

[00:41:18] - Base layers of infrastructure needed to create the best future for crypto gaming

[00:44:32] - Shared qualities between games that have a high replayability rate

[00:46:40] - Good and bad tokenomic ecosystem designs

[00:48:17] - What the biggest risks are for the future success of crypto gaming  

[00:49:26] - What factors will ensure the future growth and adoption of crypto gaming  

[00:50:25] - How much fiat flows through Axie and the growing value of in-game assets

[00:52:05] - Whether or not we’ll see purchasable utility items in the future

[00:53:21] - What he’s most excited about for the future of the metaverse

[00:54:52] - The kindest thing that anyone has ever done for him

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