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Invest Like the Best with Patrick O'Shaughnessy

Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com
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Now displaying: December, 2018
Dec 18, 2018

My guest this week is Keith Rabois. Keith is currently an investment partner at Khosla Ventures, but has a storied and diverse background as an investor, entrepreneur, and executive. He has worked in senior positions at Paypal, LinkedIn, and Square; has led investments in companies like Stripe, YouTube, Palantir, and AirBnB; and started the company OpenDoor, which aims to transform the process of selling a home through technology.

One fun fact about Keith is that he may have the most impressive list of bosses I’ve ever seen, which we discuss during the episode.

We cover a lot, but one thing we kept returning to was business strategy. Keith’s frameworks for gaining and building strategic power helped me clarify my thinking on the topic, and his examples of contrarian thinking will hopefully make you question some commonly held beliefs.

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

1:35  (First Question) – A look at his investing philosophy

3:16  – Favorite examples of his own investment history

            4:40 – 7 Powers: The Foundations of Business Strategy

5:07 – Understanding what is anomalous in a given investment

7:07 – How much a secret needs to be protected within a business

11:51 – Why accumulating advantage with data is of interest to Keith

15:12 – Digital health companies and ideas that he finds compelling

16:17 – Nuance around financial services that investors should be mindful of

17:56 – How do they evaluate managers ability to recruit talent

19:36 – How similar are the roles of entrepreneur, board member, investor, etc that Keith has had in his career

24:02 – Ways that Keith is a contrarian, including his feelings on “lean startup.”

27:04 – Is problem identification a specific skill set

28:29 – Objection with experimentation/iteration

30:02 – Bad ideas in venture

31:36 – What he likes about Apple

            31:51 – Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs

32:26 - Interview questions for identifying great talent

35:41 – Elements of good design

37:14 – Impact of platforms on opening new opportunities

38:42 – His take on valuation in the early stage environment

40:33 – Advice he would give people early in their careers

43:58 – Do high growth companies get beat by established larger businesses

45:25 – Popular narratives that he thinks are just wrong

48:22 – His thoughts on how people should learn, balancing experience vs information gathering

50:00 – Other investors that are taking a unique approach to investing

51:57 – Reflecting on the entrepreneur as a client model of private equity

55:04 – Books that he recommends that is least known

            55:18 – The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It

56:30 – Kindest thing anyone has done for Keith

 

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

Dec 11, 2018

My guest today is Bryan Krug, who manages the Artisan Partners Credit Team and overseas more than $3B in high yield credit investments for the firm. This was my first conversation on high yield, so I took it as an opportunity to get an overview on the investment universe and home in on the tools used for analysis and security selection.

As an equity investor, I think one of the most fruitful areas of research is into ways that companies fail or go wrong, and credit investors focus almost entirely on this potential for impairment. My guess is that all equity investors will learn something useful from this conversation. 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

2:11 – Overview of the high yield debt markets

5:05 – Why should investors consider this investment class

7:11 – How analyzing a company’s debt is different from what equity analysts look for

8:42 – Primary factors when exploring a company’s ability to de-lever

9:43 – What is their alpha vs others in the space

12:02 – Deep dive into the quantitative factors for them to look into a deal

14:25 – Benchmarks he uses

16:08 – Portfolio construction

17:15 – Their preference for broadband providers over cable tv networks

20:01 – What piques his interest about spreads

21:50 – The ratings of debt

25:40 – A recent example of an opportunity and how the mispricing was identified

29:17 – Most valuable data sets in this world

31:51 – Favorite part of this process

32:26 – Most surprising new learning

33:01 Maintaining your advantage

34:49 – The biggest pools of error in this industry

48:00 – What industries interest Bryan

40:50 – Dedication to this market

41:45 – Evolution of his healthy skepticism

42:38 – Can things in the debt market help to project what will happen in the equity markets

44:56 – Current view of the world based on what is happening in the credit markets

45:51 – Categories of convenience that he cares about

49:15 – Anything that has him worried in high yield markets

50:38 – Kindest thing anyone has done for Bryan

 

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

Dec 4, 2018

My guest this week is Maureen Chiquet, the former longtime CEO of Chanel. Maureen also spent much of her career at the Gap, growing Old Navy from scratch, and serving as the president of Banana Republic.

The topic of discussion is her experience running large businesses and of finding one’s way in a career and as a leader of others.

I hope you enjoy this unique conversation and that it encourages you to, among other things, travel somewhere new and interesting in the coming year.

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 importance of being able to put yourself in other people’s shoes

            3:05 – Scott Norton Podcast Episode

4:36 – Most memorable sale from her early career

5:03 – The intersection of facts and emotions in sales

6:40 – Most important emotions in business

7:30 – The importance of identity as part of the selling/marketing of sales and products

9:10 – Difference in strategy for luxury brands vs others

            9:21 – The Luxury Strategy: Break the Rules of Marketing to Build Luxury Brands

10:55 – Striking a balance between tradition and innovation

13:46 – Advice for new brand company related to rarity

14:59 – Importance of being organic with your brand purpose

            15:01 – Wild Company: The Untold Story of Banana Republic

16:26 – Maureen’s purpose over the years

18:44 – How to harness your purpose for your job

20:53 – Her process for writing and desire to do TV

24:01 – Her time with Micky Drexler

27:40 – As a leader, guiding people to succeed.

32:33 – Strategy for shifting culture at a company

37:54 – The importance of courageous conversations we should all be having

43:45 – Markers of courageous conversations

46:43 – How she thinks about introspection

50:12 – What draws here to certain locations

55:15 – Advice for younger people starting out their career

57:11 – Kindest thing anyone has done for Maureen

 

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

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