Invest Like the Best with Patrick O'Shaughnessy

Latest Episodes:

Zach Perret – The Future of Financial Services – [Founder’s Field Guide, EP.13] Dec 24, 2020

Show notes

Zach Perret is the founder and CEO of Plaid. Plaid helps companies build fintech solutions by creating APIs that allow people to connect their financial data to apps and services. In this conversation, we dive into Zach's philosophy on building products, how the financial system works today, how the financial system needs to be updated, and the trends Zach is seeing from the next wave of fintech companies launching on Plaid. I hope you enjoy this conversation with Zach Perret.

For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/39328476/perret-the-future-of-financial-services

DocSend is a document sharing platform that enables companies to share business-critical documents with ease and get real-time actionable analytics. With DocSend’s security and control, startup founders, investors, business development executives, and financial professionals can drive business outcomes that have a lasting impact. Start for free at www.docsend.com.

Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide go to https://www.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 - https://www.joincolossus.com/newsletter.

Follow Patrick on Twitter at @patrick_oshag

Follow Colossus on Twitter at @JoinColossus

Show Notes

[2:00] – [First question] – The notion of Great Challenges he got from his parents

[3:34] – How it was instilled into him

[4:26] – Default Consumptive State and constantly asking questions

[5:33] – Origins of Plaid

[8:57] – An overview of the Plaid product

[11:10] – The early challenges of building Plaid and creating trust with all of the stakeholders

[15:57] – First big break for Plaid

[18:06] – Convincing Venmo to work with them

[20:12] – What helped build relationships with customers

[21:30] – How money is moved and their place in the chain

[24:34] – How convenience helps to create larger markets and opportunities

[26:39] – Usage base vs recurring revenue models

[28:03] – Maintaining their systems as the landscapes and customers shift

[29:56] – What is he seeing on the financial services frontier

[32:34] – Building relationships with developers

[35:07] – Lessons from building a business he’s learned along the way

[37:44] – Successful techniques in recruiting

[39:52] – What’s working well in this current landscape

[41:41] – Business models that interest him

[43:14] – Advice for other startup founders

[44:49] – Things he doesn’t understand today that he wishes he did

[45:46] – What he attributes Plaid’s success too

[47:55] – Kindest thing anyone has done for him

[50:09] – How you know when you’ve found a great challenge

Mario Cibelli - Cornerstone Investing Insights - [Invest Like the Best, EP.205] Dec 22, 2020

Show notes

My guest today is Mario Cibelli. Mario is the managing partner of Marathon Partners Equity Management, a long-biased, concentrated investment firm that he's run for over 20 years. In our conversation, we discuss how his firm figured out Blockbuster's DVD volume and told Reed Hastings and Netflix about their numbers, why visiting a company's distribution center can be an edge for investors, Mario's interesting foray into the world of tequila, and how a few "cornerstone" investing insights have led to many of Marathon's long positions. I hope you enjoy my conversation with Mario.

This episode of Invest like the Best is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Square, Snowflake, or almost any company of interest. All you have to do is log in. Visit https://www.tegus.co/patrick to learn more.

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(2:34) – (First question) – Doing a deep dive into the early days of Netflix

(2:43) – Netflixed: The Epic Battle for America's Eyeballs

(6:50) – What was impressive about Reed

(7:34) – Visiting Netflix’s distribution centers early on and the lessons of those visits

(10:44) – Lessons learned from other distribution centers

(17:52) – What helps create good luck for a company

(19:17) – Why tequila was fun to investigate

(25:09) – Why tequila is different from other hard liquors

(27:40) – Finding the cornerstone insight in a company

(29:20) – What he’s learned about media-driven personalities and WWE

(34:30) – Lessons in starting a media company and developing IP

(39:00) – Having to battle activist shareholders in business

(42:43) – How the rate of return in deep investigations has changed over his time

(45:08) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Bob Pittman - Lessons from Building Media Empires – [Founder’s Field Guide, EP.12] Dec 17, 2020

Show notes

My guest today, Bob Pittman, has had one of the most interesting careers I’ve ever come across. Today, he’s the CEO of iHeartMedia, the country’s largest operator of radio stations and podcasts. Bob also created MTV, was the CEO of Six Flags and 21 Century Real Estate, and the COO of AOL and AOL Time Warner. He’s the Dos Equis man of business. In our conversation we discuss why convenience is king for consumers, his lessons from building MTV into one of the most iconic brands and media properties in the world, the rise of user-generated content platforms, and the future of media. We also discuss what qualities make for a great host, a topic that given my current position, is always fascinating. Please enjoy my great conversation with Bob Pittman.

This episode of Founder’s Field Guide is also brought to you by NetSuite. Netsuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly. Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at https://www.netsuite.com/invest.

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(2:56) – (First question) – His personal interest that unites all of his business ventures

(4:09) – His philosophy on the consumer

(7:43) – Biggest quality mistakes business leaders make

(9:31) – Respecting convenience in consumer preferences

(11:08) – Founding insight to build MTV

(16:23) – Fred Seibert on Math in Magic Podcast

(17:14) – How the music video concept evolved with MTV

(22:37) – Role of hosts vs guests in the media world

(25:13) – Quality that increases the odds a host works

(30:15) – Why everyone needs to know how to tell a good story

(31:53) – Peak of his time at MTV

(37:51) – Lessons for new media from his experience

(43:46 – The largest uncertainty in the media landscape amid the rise of user generated content platforms

(49:27) – Where he finds inspiration outside of business

(55:40) – What Other People Say May Change What You See

(56:16) – Different ownership structures and how they changed his behavior

(59:09) – Finding and respecting your audience

(1:02:11) – Lessons from time at Six Flags

(1:02:24) – Most interesting thing about podcasting

(102:52) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Sam Hinkie – Find Your People - [Invest Like the Best, EP.204] Dec 15, 2020

Show notes

My guest today is Sam Hinkie. Sam worked for more than a decade in the NBA with the Houston Rockets and then as the President and GM of the Philadelphia 76ers. And now, after years of personal investing, he has launched his own venture capital firm, Eighty-Seven Capital. Every conversation I have with Sam is alive with insight, and this one is no different. We explore the idea of studying the "breadcrumbs" that someone leaves behind as a way to track their progress and trajectory, finding and attracting the right people into one’s orbit, and the lessons from the NBA that most shape his investing career. Sam has taught me the most about the topic of building trust, which we cover here as well. I am excited to share my conversation with Sam with all of you. Please enjoy!

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(3:48) – (First question) – Conducting a good interview

(5:58) – Drilling into topics to learn more about people

(7:49 – What percentage of people are actually worth spending time with for Sam

(9:29) – People who think in a strange way that intrigues him

(10:36) – Interest in digital breadcrumbs and how to follow them

(14:02) – Building context around founders vs analyzing their pitch decks

(17:20) – A real world example of the bread crumb strategy, Houston Rockets GM

(21:25) – How successful people evolve with the erosion of their pre-established edge

(23:07) – Shifting to a people-first focus

(24:50) – Creating an atmosphere that attracts the best talent

(26:50) – Tailoring things to someone else’s incentive structure

(28:24) – Most amazing thing someone did in early days of working with Sam

(30:18) – Lessons from sports that he carries with him

(32:31) – Exceptions to relationships being a key to success

(33:03) – Have people gone soft?

(34:58) – Knowing whether founders are on the right path

(36:07) – Avoiding transactional type people

(37:04) – Most effective lessons he brought to sports from the investing world

(40:01) – Ideas from the sports world he is bringing to the investing world

(44:11) – How the size of the team can impact the success of the team

(45:48) – Designing the game for himself

(50:33) – Lessons learned from watching them build trust

(52:26) – Market areas that have his attention

(54:13) – Fascination into API’s

(58:05) – Keeping your focus on your expertise

(59:45) – Strangest things he’s seen in early stage investing

(1:01:26) – Playing the long game

(1:04:29) – Calling it Eighty-Seven Capital.

(1:04:42) – Means of Ascent (The Years of Lyndon Johnson)

(1:05:49) – Increasing his chance at a GM job

(1:06:52) – What can Caro teach us about the long game

(1:08:26) – Lessons of power

(1:10:39) – Quality in leaders he respects most

(1:11:17) – The Passage of Power: The Years of Lyndon Johnson

(1:12:58) – The power of breadcrumbs and how people can start to lay them out

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Michelle Zatlyn – Protecting the Internet – [Founder’s Field Guide, EP.11] Dec 10, 2020

Show notes

My guest today is Michelle Zatlyn. Michelle is the co-founder and COO of Cloudflare, a now $25 billion dollar business which she helped take public last year. Cloudflare helps businesses make their websites faster and more secure, and over 25 million websites are running Cloudflare today. In our conversation, we discuss the catalyst for starting CloudFlare, explore the layers of the internet and the future of distributed storage and computing power, and discuss how and why Cloudflare operates its network across 200 cities globally. We close with the importance of finding and working with great co-founders and partners as you build a business. I hope you enjoy our conversation.

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(2:52) – (First question) – Project Honeypot and how it started

(3:39) – What question was Honeypot solving

(4:59) – Working through the idea maze of Cloudflare

(7:30) – The first iteration of Cloudflare

(8:15) – An overview of the cybersecurity market and why more leaders need to pay attention

(10:33) – First big break for the company

(12:50) – Risks they help mitigate

(16:42) – Cyber weapons that Cloudflare protects against

(20:14) – Hardest part of the building process

(24:06) – Effective marketing lessons

(25:41) – The sharks vs mosquitoes concept

(27:53) – How do decide where to focus next

(31:34) – The Cloudflare workers program

(36:33) – Their scale vs other cloud providers

(42:21) – The finance side of Cloudflare and their relationship vs Wall Street

(42:40) – John Collison Podcast Episode

(44:47) – Relationship with their founding partners

(50:46) – What about the future is most excites them

(52:32) – Kindest thing anyone has done for her

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Danny Meyer – The Power of Hospitality - [Invest Like the Best, EP.203] Dec 08, 2020

Show notes

My guest today is Danny Meyer, the founder and CEO of Union Square Hospitality Group, which compromises some of the most acclaimed restaurants in New York like Gramercy Tavern and Union Square Café. He’s also the founder and chairman of Shake Shack, which began in New York City but is now a publicly traded company with hundreds of locations worldwide. Our conversation focuses on how great hospitality leads to a great business, regardless of what sector its in. We discuss why hospitality is the starting point for Danny’s business philosophy, why first impressions matter, Danny’s concept of ABCD - always be connecting dots, how to scale hospitality, and how to build a business with essentialism and soul. The other day, when my young son went ice skating and fell a lot he said to me “well you learn from your mistake so you try to make as many of them as you can.” You’ll hear Danny say something powerfully similar late in the conversation. It’s a lovely thought, then, that I found out my son, my firstborn, was a boy in one of Danny’s restaurants, in a reveal orchestrated by his incredible team. I really hope you enjoy our conversation.

This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.

With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick.

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(3:41) – (First question) – His experience as a tour guide in Italy

(8:17) – Why hospitality is the center of business focus

(8:19) – Setting the Table: The Transforming Power of Hospitality in Business

(11:50) – Early lessons at creating an environment of hospitality

(15:17) - His strategy ABCD and learning from a trout fisherman relate and relate to hospitality

(20:45) – Scaling hospitality

(24:56) – What kind of people make a hospitality business work

(29:34) – How to be an effective leader

(33:00) – Handling mistakes well in the role of hospitality

(36:28) – Creating the spark in the early part of entrepreneurial ventures

(40:32) – When its time to start something new vs expand something you are already doing

(45:52) – The excellence reflex and an example of this in his career

(50:25) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Zac Bookman – How Government Works – [Founder’s Field Guide, EP.10] Dec 03, 2020

Show notes

My guest today is Zac Bookman. Zac is the Founder and CEO of OpenGov a budgeting and financial management software for local governments. Before he founded OpenGov Zac was an Advisor to U.S. Army General H.R. McMaster in Afganistan, a law clerk on the Ninth Circuit Federal Court of Appeals, and earned a Fullbright Fellowship studying corruption in the Mexican government. This conversation is one of the most unique and wide-ranging of any I've had on the show. We cover how Zac built a world-class sales organization, the power of selling momentum, and the role capital efficiency still plays in building great companies. We also dive into the details on how local government works from mayors down to school board meetings. Please enjoy my conversation with Zac Bookman.

This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out.

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(2:56) – (First question) – His career leading up to OpenGov

(5:45) – Experience in Afghanistan and lessons from his time there

(8:54) – Aligning a large group on a strategy

(9:56) – Aligning the team at OpenGov when getting started

(11:54) – Levels of government that matter and what their systems looked like when he was getting started

(15:24) – Role of budget and how money flows in in government operations

(18:55) – How technology can fix the bureaucracy of government

(21:40) – Can technology help the public’s relationship to government

(24:20) – Defining vertical SaaS products

(27:02) – Picking the right products/customers to build your product well

(28:33) – Their purpose when building their first product

(30:23) – Building a company in a highly regulated space

(32:14) – Selling in this space and lessons learned

(34:04) – Building a machine to distribute enterprise software

(37:03) – Getting the technical, political, and commercial processes aligned

(39:40) – Staying up to date on the market and fending off your competition

(42:18) – Competency within public governments

(44:03) – Metrics that he uses to understand the health of OpenGov

(46:07) – The importance of charging the right price for professional services

(48:36) – Hardest episode in developing OpenGov

(50:17) – Valid early criticisms of the company

(52:34) – Advice to new entrepreneurs entering the vertical SaaS space

(54:06) – The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

(57:04) – Engineering momentum among teams

(59:00) – Personal improvement as a leader

(1:01:55) – The study of death and why it’s important for him

(1:04:19) – What people can get spending time in the mountains

(1:06:53) – Role of capital efficiency in his work

(1:09:11) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Daniel Gross – Finding Undiscovered Talent - [Invest Like the Best, EP.202] Dec 01, 2020

Show notes

My guest today is Daniel Gross. Daniel is the founder of Pioneer, an extremely unique company which he describes as a “fully remote startup generator” that helps talented people around the world figure out if their idea has legs. You can learn more about it at pioneer.app. Our wide-ranging conversation covers the art of asking great questions, the use of predictive modeling and psychometrics to identify talent, and why psychometrics are probably overrated and not that scientific. We then dive into exciting new frontiers for tech investing ranging from GPT-3 to satellites. I really enjoyed this conversation and I hope you will too.

This episode of Invest like the Best is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you'd want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Square, Snowflake, or almost any company of interest. All you have to do is log in. Visit https://www.tegus.co/patrick to learn more.

This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(3:15) – (First question) – His passion for Crank and Whiplash and why movies are great screeners for interviews

(6:15) – Overview of Pioneer

(7:56) – Defining talent

(10:02) – The equivalent page rank when it comes to people

(14:10) – Psychometrics and matter to him

(18:13) – The importance of persistence

(20:23) – The concept of insecure overachievers

(22:48) – Fast twitch vs slow twitch capitalism

(24:31) – Importance of memes as it relates to human behavior today

(26:14) – The landscape of the type of businesses being formed

(29:25) – Overview of GPT3

(33:33) - The Power of Ten Playbook

(38:08) – Technologies going from a frontier to a utility

(42:45) – Why something like a Starlink can’t be regulated

(44:58) – Seed vs leech ratio in capital funding

(49:10) – Give and Take: Why Helping Others Drives Our Success

(49:15) – Dissecting Patrick’s usual closing question and good questions for screening people

(52:56) – What questions help him get to the bottom of

(55:58) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Emmett Shear - The New Language of the Internet – [Founder’s Field Guide, EP.9] Nov 26, 2020

Show notes

My guest today is Emmett Shear, founder and CEO of Twitch. Twitch is the world's leading live streaming platform for gamers, which was acquired by Amazon in 2014. We talk about how Twitch empowers streamers to monetize their audience, the necessity of picking a customer early in a business, and the lessons Emmett learned scaling Twitch from an online reality TV show to a global brand inside Amazon. We also discuss how Twitch has helped create a new language in the internet age with emotes, a topic I am fascinated by. I hope you enjoy this conversation with Emmett Shear.

This episode is also brought to you by Solo Stove. There's simply no better way to create good moments this holiday season than around a fire with a Solo Stove Bonfire. Complete with 30-day return policy and a lifetime warranty, the unit is made entirely of stainless steel, and at just 20 pounds, the Solo Stove Bonfire is easy to transport for a perfect evening in the backyard, at the campground, or on the beach. Get $5 off with code Patrick5 before December 31st 2020.

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(2:52) – (First question) – History of interactive entertainment

(4:10) – Interactivity from the clubs in Vienna and what he learned from that

(5:16) – Origins of Justin.TV and when gaming became the focus for Twitch

(8:59) – What he enjoyed about video streaming games early on

(10:21) – Interactive experience between creators and community

(12:28) – Emotes on twitch and how they came to be

(14:45) – Business of emotes and the affiliates

(16:27) – How these features are proliferating out on the internet and changing it

(17:21) – How far we are in the streamer-influencer phenomenon

(20:00) – Building an effective platform for fans

(23:07) – Evolution of the just chatting piece of Twitch

(24:58) – Favorite parts of Twitch from followers: Chess

(26:45) – Running a business within a larger business

(28:09) – Most interesting trend in the market today

(30:40) – Effective ways for recruiting the team

(31:35) – Most curious about what is happening on the internet today

(33:06) – Advice from the early days of Twitch

(35:55) – Ira Glass video taste and making things

(36:34) – Focus on strategic mission

(38:06) – Identifying the customer

(40:40) – Starting small

(41:45) – Investors focus on potential market size

(43:00) – Most common reasons talented people fail

(43:47) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

RRE Ventures - RRE Ventures - Raju Rishi, Nikita Singareddy, Jason Black - [Invest Like the Best, EP.201] Nov 24, 2020

Show notes

My guests today are Raju Rishi, Nikita Singareddy, and Jason Black of RRE Ventures. RRE is a New York-based VC firm investing in early-stage start-ups with more than 400 investments over its 25 year history. Raju, Nikita, and Jason focus their time in the world of healthcare investing, a topic I haven't explored much personally or on this show. We discuss the current landscape for healthcare investing, the variety of stakeholders in the healthcare value chain, the opportunities for founders and investors in the space, what excites them most about the future of the space, and the impact COVID has had in shaking up the industry. I hope you enjoy my conversation with the RRE team.

This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin.

Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com

Ladder Teams is a modern personal training experience with expertly designed workout plans, 1x1 access to some of the best coaches in the world, and the power of community, all delivered to your phone.

If you’re looking to switch up your fitness routine at home or if you are back at the gym and looking to refresh your training plan Ladder Teams has a program for you. Check out https://ladder.fit/Patrick to download the app and get started.

For more episodes go to InvestorFieldGuide.com/podcast.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(2:34) – (First question) – How the team think about attractive investment concepts

(7:13) – The current landscape for healthcare investments

(8:53) – Complications in pricing healthcare and where it needs to change

(17:45) – Catastrophic Care: Why Everything We Think We Know about Health Care Is Wrong

(17:55) – The major stakeholders and where the innovation is coming from

(18:22) – The Patient Will See You Now: The Future of Medicine Is in Your Hands

(24:43) – How Covid is changing the healthcare sector

(28:43) – Cutting edge of remote patient monitoring

(37:03) – Passive monitoring and future tech of healthcare