Invest Like the Best with Patrick O'Shaughnessy

Latest Episodes:

Peter Zeihan - Dis-United Nations - [Invest Like the Best, EP.159] Mar 10, 2020

Show notes

My guest this week is Peter Zeihan, the author of a new book, the Disunited Nations. Peter was an extremely popular guest on the show last year and after reading his new book, I knew we had a lot to discuss in round 2. In this conversation, we discuss two ways of ruling the world, the coming American disinterest in global affairs, and which country are poised to do well int eh future. We explore military and non-military technologies, political changes, and up and coming alliances like that between the United States and Mexico. As with last time, peter packs more information into an hour than just about anybody. Please enjoy our conversation.

This episode is brought to by Koyfin.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:57 – (First question) – What makes for a successful country

6:02 – Five first-tier countries that are well positioned

7:14 – Ruling the world, US carrot model vs British stick model

9:39 – How other countries will use these models in the future

12:59 – The surprising reliance of Iran and Russia on the US

15:24– Key points of his research on the Middle East

18:36 – Advice for how those operating in the US should think about future business investments

23:05 – The future of manufacturing partnerships with the US and the focus on Mexico

27:30 – What Coronavirus has taught us about the world economy

30:01 – What the primaries and election are teaching us

35:09 – What role does Africa play in the future

38:36 – Strong and weak players in Europe and how Brexit has impacted things

44:41 – The future for nuclear power

46:27 – The outlook for South America

50:42 – The trends and future in military technology

55:03 – Non-military technology that will have a major impact

58:26 – Skills young people should focus on for the future

1:00:07 – Coronavirus as a dress rehearsal for large scale disruptions to the world

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on Twitter at @patrick_oshag

Jeff Lawson – How to Build a Platform - [Invest Like the Best, EP.158] Mar 03, 2020

Show notes

My guest this week is Jeff Lawson, the Founder, and CEO of Twilio. Twilio is a 15-billion-dollar company offering a cloud communications platform to its customers. Twilio is used by customers like Lyft, Twitch, and Yelp to make communications in their products easy. Jeff and I talk about why it pays to be a platform, how to be a platform, and how to sculpt a company culture. This is a must-listen for anyone building a business whether it’s a tech business or not.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:18 – (First Question) – Company vowels and draw the owl

5:26 – Significance of API’s

12:14 – How non-software businesses can transition into the space

17:50 - Agile way of working at ING Belgium (video)

18:38 – How they strategize their product build

23:27 – The idea of asking your developer and why it’s so important to them

33:02 – How they codified their business culture

45:12 – Parting advice for people building platforms

48:13 – Kindest thing anyone has done for Jeff

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on Twitter at @patrick_oshag

Niko Canner – Become a Perfect Instrument - [Invest Like the Best, EP.157] Feb 25, 2020

Show notes

Niko Canner is the founder of Incandescent where he and his team help the leaders of large companies in the areas of strategy and innovation. He was also the founder of Katzenbach Partners and a member of Bridgewater’s management committee. Niko is a fantastic writer, and I highly recommend you check out his blog “On Human Enterprise,” which has posts on many of the most interesting aspects of business and personal purpose. This conversation was inspired by many of those posts. Please enjoy.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:17 – (First Question) – The story of Doctor V

3:24 – Aravind and the Choice of Great Achievement

4:00 – Becoming the perfect instrument

6:05 – What is Niko planning to be the perfect instrument of

8:18 – How should individuals think about finding what they can be the perfect instrument of

8:59 – Brett Victor – Inventing on Principle

10:59 – How do businesses apply this principle

13:20 – Making choices easier

16:43 – Era’s to a company and when it’s time to start a new one

19:52 – How can business culture be cultivated and useful

22:53 – Cultures at the tail end of a distribution

24:33 – Can hierarchy be fluid, or does it need to be a dedicated corporate structure

27:47 – My Unlikeliest Favorite Business Book

28:03 – The Millionaire Real Estate Agent: It's Not About the Money...It's About Being the Best You Can Be!

30:46 – The Red Test and how it can be used by businesses

36:54 - Ten Principles for How to Run a Company

42:25 – Dealing with the sponsor owner brief in the software world

45:24 – How does one choose customers

46:32 – Bill Hubbard passage – A Theory for Practice: Architecture in Three Discourses

49:09 – Kindest thing anyone has done for Niko

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on Twitter at @patrick_oshag

[REPLAY] What You Learn About Business Deals After: 12,000 Deals Reviewed, 1,500 Deep Dives, 125 Site Visits, and 7 Portfolio Companies with Brent Beshore - [Invest Like the Best, EP.100] Feb 04, 2020

Show notes

For the 100th episode, I’ve brought back my good friend Brent Beshore. Brent was the 10th guest on the podcast, after we met because of a mutual interest in capital allocation. I quickly learned that Brent was one of the most unique and thoughtful investors around. He was an entrepreneur from the moment he left school, trying many different things before finding a fit buying smaller business with the intention of owning them forever. What amazes me about Brent is his encyclopedic understanding of business and the nuances of different business models and deal structures. This comes from reps. He and his team have looked at about 12,000 deals over the years, at every kind of business that you could imagine. I’ve been with him when he goes through this process and it’s fun to hear what makes certain businesses stand out from others, which is largely the topic of this conversation. You all know transparency is key for me, so it’s important to know that my family and I are investors in a fund called permanent equity, run by Brent and his firm Adventure.es. To commemorate this milestone episode, I can think of no one better than Brent, because he exemplifies what has made this podcast so fun for me: learning from other people who are willing to share what they themselves have learned through fun, blood, sweat, and tears. Please enjoy our conversation, and thank you so much for coming along on this journey. I can’t tell you how much it means to me.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

2:02 - (First Question) – How does he think about optimizing risk in terms of the capital stack when looking at deals

5:27 – What conditions would they add debt down the road after investing in a company

6:52 – What business sectors are most intriguing for Morgan to invest in right now

6:57 – Trent Griffin Podcast

9:34 – Why no HVAC businesses if it’s such an attractive sector

13:56 – thoughts on rolling up similar businesses and horizontal scale

16:04 – Another industry Brent would focus on

18:02 – Difference between property management in larger cities vs smaller metro areas

18:51 – What role does profit margin play when Brent is evaluating a business

22:46 – The appeal of a hyper cyclical business

22:52 – Brent Beshore Podcast Episode

27:27 – Favorite counter cyclical business

28:14 – How they judge assets, tangible vs intangible assets

33:58 – How does he think about wage inflation when considering the cost of a business

37:21 – His fascination with pet crematoriums

38:57 – History of the permanent equity fund and the changes by having a larger pool of capital

43:48 – Pitching investors on a new structure for the business

46:14 – How will this business model scale

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on twitter at @patrick_oshag

Chetan Puttagunta – Go Slow to Go Fast: Software Building and Investing - [Invest Like the Best, EP.156] Jan 28, 2020

Show notes

My guest this week is a good friend and a business mentor of mine. Chetan Puttagunta is a general partner at Benchmark Capital and has a remarkable track record of investing in early-stage software businesses, including several like Mulesoft, MongoDB, and Elastic that went on to be public companies.

Chetan has been my key guide for understanding the world of enterprise software as we at O’Shaughnessy Asset Management have built an investing platform called Canvas. His advice has been critical to our early success. In this episode, we explore the history of software and software investing, and go into the details on how to build and grow new software businesses. We discuss product, sales and marketing, recruiting, scaling, and everything in between.

Please enjoy this great conversation with one of my favorite business and investing thinkers.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:34 – (First Question) – How Chetan found MongoDB and decided to invest in it

8:01 – The evolution of databases in the growth of technology

16:19 – Market penetration of this space and what investors should be thinking about

21:46 – Advice how companies can build software effectively

25:12 – Tactics to effectively implement empathy led product building

30:33 – Companies asking users what to build vs telling users what they want

34:26 – The need for the right capital, and patient capital in particular

37:55 – Creating the perfect customer experience

44:37 – Common reasons they don’t invest in a company

48:48 – Lessons on scaling, especially in sales and marketing

52:47 – Best recruiting pipeline strategies

59:56 – Pitfalls of unit economic traps

1:00:23 – The Dangerous Seduction of the Lifetime Value (LTV) Formula

1:01:34– The Hierarchy of Engagement

1:02:18 – What has changed for Chetan in his time working with the team at Benchmark

1:06:009 – Later stage life cycle business considerations and Amazon’s AWS

1:13:29 – The business model of open-source software

1:15:54 – Being default open

1:17:53 – Kindest thing anyone has done for Chetan

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on Twitter at @patrick_oshag

Rebecca Kaden – Thesis Driven Investing - [Invest Like the Best, EP.155] Jan 21, 2020

Show notes

My guest today is Rebecca Kaden, a partner at famed venture firm union square ventures. USV is known for thesis-driven investing, which is the topic of our conversation. Rebecca walks us through the evolution of USV’s thesis into its third generation, and from there we explore many of the most interesting and exciting areas of business, technology, and learning. Please enjoy our conversation

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:11 – (First Question) – An overview of Union Square Ventures Thesis 3.0

7:49 – Core changes that can help any community

9:59 – Ways to fix the broken education system

13:41 – Gap between job preparedness and the education system

14:44 – Companies creating education systems to prepare people for careers in their field

18:49 – Most unique technological solution for people to educate themselves

22:00 – Ways to improve access to capital

26:49 – The distribution problem in capital markets

28:19 – How does she assess an early-stage company and its team’s ability to assess their ability to maximize distribution

30:56 – Digital marketing and why it could be broken

34:22 – Examples of masterful marketing

36:07 – How they are focused on improving wellbeing, their first focus on healthcare

39:35 – Wellbeing on their focus on community

41:29– The Art of Community: Seven Principles for Belonging

45:30 – Her thoughts on mentorship

48:23 – What she has learned in her time at USV

51:50 – Kindest thing anyone has done for Rebecca

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on Twitter at @patrick_oshag

Matt Clifford – Investing Pre-Company - [Invest Like the Best, EP.154] Jan 14, 2020

Show notes

My guest today is Matt Clifford. He’s the co-founder of Entrepreneur First, the world’s leading talent investor. They invest “pre-company” by helping the best people in cities around the world find a co-founder, develop an idea, and start a company. So far, they’ve helped 1000 people start 200 companies worth a combined $1.5B. This conversation covers their entire ecosystem and holds lessons for anyone building a business. I especially loved Matt’s ideas on the history of ambition.

Please enjoy our conversation.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:20 – (First Question) – An overview on talent investing

4:37 – The history of ambition

10:08 – How do they search for ambitious people

12:21 – What happens early on for these formed teams

17:43 – Assigning an idea to a talented team

20:52 – Opportunities in deep technology

27:16 – A closer look at the hardware and machinery of the deep technology changes

30:54 – The geographical focus of venture capital investments

37:16 – Problems with the way early-stage investment world works

41:22 – People who are creating value in a management company and how they manage their investments

55:12 – Advice to people creating investment companies and pricing power

1:00:31 – The power of cities

1:02:46 – Topics they cover in their newsletter; technological sovereignty as one example

1:04:11 – Experience and thoughts on China

1:06:51 – A.I. Nationalism

1:12:03 – Kindest thing anyone has done for Matt

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on twitter at @patrick_oshag

Peter Buffett – Finding Your Note - [Invest Like the Best, EP.153] Jan 07, 2020

Show notes

My guest today is Peter Buffett. Peter is a musician, composer, author, and philanthropist. Peter is an Emmy Award winner, New York Times best-selling author and co-chair of the NoVo Foundation. We discuss music, community, philanthropy, and finding one's note in life. This is a very different episode much more about life in general, with no business or investing discussed. Like his father Warren, Peter has the gene for phrasing ideas in memorable ways, and I think you’ll find many great phrases in this chat that will stick with you. I’ve been thinking about Peter's idea making sure those in your life are safe, seen, and celebrated ever since our chat.

Please enjoy.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:27 - (First Question) – Welcome and small talk

1:35 – Why Peter is in Kingston and how it plays into his foundation work

4:01 – How moving from the city to the country changed Peter

6:27 – Seeing connections vs living abstractions

7:30 – What is the Nova Foundation

11:03 – Historical points that inform his views

13:51 – Identifying qualitative negative side effects and which ones they are attacking

17:51 – What makes for effective community

20:22 – Linkage between consumption and individualism

23:55 – The cultivation of work ethic, curiosity, and education

23:57 – Life Is What You Make It: Find Your Own Path to Fulfillment

27:22 – Early exploration of his curiosity

32:26 – What has music taught Peter about music that is unique to that experience

34:26 – Most memorable question a person has asked Peter at his concert and conversation series

36:46 – What makes for good relationships, in particular marriage

42:03 – What keeps people from putting in the work into a relationship

45:11 – What he has learned about being a good friend

46:29 – How does one person have a relationship with a large community

49:21 – Dark sides of the philanthropic world

49:54 – The Charitable-Industrial Complex

53:21 – Dignity: Seeking Respect in Back Row America

55:55 – What one spot would he send everyone to learn

57:48 – Traumas and helping people find their note

57:49 – The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma

1:00:38 – How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence

1:02:24 – What is he most interested in right now: how to best use Nova’s funds

1:04:45 – Lessons from family

1:07:22 – Kindest thing anyone has done for Peter

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on twitter at @patrick_oshag

Ben Savage – All Things Fintech Investing - [Invest Like the Best, EP.152] Dec 17, 2019

Show notes

My guest today is Ben Savage, a partner at Clocktower ventures. Ben is focused on financial technology, fintech, investing which is the topic of our conversation. I’ve been making the fintech is rounds of late, and plan on making a few of these conversations public. Ben is the first in what may be a mini-series because of the sheer amount I learned in our discussion. We cover all aspects of the fintech ecosystem. I hope you enjoy.

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:15 (First Question) – The market portfolio and how technology will move us away from liquid markets

7:24 – Businesses that are making assets that weren’t investable, investable

9:11 – Ryan Caldbeck Podcast Episode

12:03 – Most interesting places where technology is creating investment opportunities

18:33 – Assets that are likely to tap into new sources of beta

23:46 – How well are investors prepared for the changes that are coming

28:35 – Trends in asset management with technology

33:05 – View on cryptocurrency and blockchain

36:45 – Places where startups can reduce costs/fees and create efficiencies

40:17 – Views on private equity markets and their future

45:40 – Privilege of access problem

48:50 – Verticals in fintech that are interesting to him

59:53 – The importance of focus and niche

1:02:26 – Kindest thing anyone has done for Ben

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on twitter at @patrick_oshag

Jeff Ma – Making Decisions with Data - [Invest Like the Best, EP.151] Dec 10, 2019

Show notes

My guest this week is Jeff Ma. Jeff was on the famous MIT Blackjack team from the book Bringing Down the House but has spent his career in an around fields of analytics and data science. He’s studied sports betting and analytics, built companies for analyzing human capital, and ran the data science and analytics group at Twitter. Here are links to his book, blog, and podcast. Our discussion is about a number of fascinating ways data is being used to make decisions in the worlds of sports and business. Please enjoy!

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:20 - (First Question) – How quantitative analytics have evolved in sports and how they’re being used

4:26 – Best role of humans in the analysis process

8:38 – Sports that are most interesting to observe through analytics

10:26 – How does luck play into sports analysis

11:54 – Team analytics vs better analytics

12:38 – Concentration of success among sports betters and their moats

14:58 – Favorite lessons learned from professional gamblers

16:45 – How analytics got introduced into gambling