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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: October, 2018
Oct 30, 2018

My guest this week is Ryan Caldbeck, a private equity investor who wants to bring quantitative rigor to the private markets. Ryan is the CEO of Circle Up, which uses a system it calls Helio to identify attractive investments in early stage consumer brands. 

While I am of course a fan of quantitative investing, I also know from experience how much harder private markets are than public markets when it comes to the transactions themselves. We discuss this and many other potential roadblocks to bringing models to private markets.

Using many individual companies as examples, Ryan explains some of the major predictive factors they’ve uncovered in their research. We also discuss which parts of the private markets might be infiltrated by quant processes first, and which may never be. 

I expect many more to go on a journey similar to Ryan’s in the years to come. They serve as an interesting example for ambitious investors out there.

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

1:39 - (First Question) – Formation of Helio

6:57 – How they handle the relationship building needed to make investments in private markets

10:26 – Why consumer and retail are interesting spaces to apply their quantitative approach in private markets

12:54 – Searching for new relevant data

16:14 – How do they stay ahead of the commoditization of uniqueness

            16:21 – Pattern Recognition and Machine Learning

            17:24 – Sam Hinkie Podcast Episode

18:00 – Dominant predictive factors in this world

21:05 – Which is more important, relative value or rate of change

21:48 – What does the data say about online sales vs offline (being in a store)

23:30 – Variable that consumer investors think matters but it doesn’t

24:53 – Valuing companies and accounting for mispricing’s

            25:36 – Michael Recce Podcast Episode

26:41 – Goes through the process using Liquid Ivy as an example

28:46 – Most interesting sub-categories

29:33 – Future for this model

            32:10 – Albert Wenger Podcast Episode

35:19 – Other categories outside consumer and retail interest Ryan

36:28 – Biggest challenges for CircleUp as a business

38:46 – Handicapping their earnings expectations

41:36 – Take on the VC/PE landscape

43:03 – The types of models that are most interesting to the team

45:05 – Quantitative elements of brand that are most interesting

47:30 – Most unique brand and distribution strategy he’s come across

53:27 – Who has influenced Ryan the most

54:37 – His personal values

55:51 – More people who had an influence on Ryan

            56:05 – The Innovator's Dilemma: The Revolutionary Book That Will Change the Way You Do Business

57:07 – Thoughts on goal setting at the company

59:29 – Unchangeable factors that shape their long-term vision

1:02:01 – Most interesting individual conversation as part of this journey

1:04:02 – If he could only keep one dataset, what would he keep

1:05:09 – kindest thing anyone has done for Ryan

 

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

Oct 23, 2018

My guest this week aspires to be the Larry David of investing, and we discuss why. Howard Lindzon is hard to categorize. He’s primarily an early stage investor right now, but he’s participated in all types of investing. He describes himself as a trend follower and always has a unique take on popular topics. 

In this conversation, we cover his investing history and his take on the fintech investing landscape. What I’ll remember most is the idea that we should focus on what is happening versus what we think will happen or might happen. There is a Peter Lynch like quality to some of Howard’s thinking, and a willingness to embrace the weird that I find very appealing. The few times I’ve met Howard, I’ve smiled or laughed most of the time, which is about as nice a thing as I could say about someone.

He’s a good example of why I like this podcast format. His investing style bears literally no resemblance to my own, but it got me thinking about a lot of new things. I hope you enjoy our chat.

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

1:42 - (First Question) – Why he wants to be the Larry David of investing

2:00 – Why his investing style is best described as trend following

4:05 – The biggest inspirations/influencers on Howard’s investing

6:39 – What made his second mentor, Fred Wilson such a great investor

9:52 – Formation of Wall Strip

12:33 – Why weird is so important in his investment philosophy

14:56 – Understanding his investment philosophy through his investment in Rally Road.

21:02 – His assessment of the fintech space

28:54 – Why fintech pushes away from human nature

30:50 – Major trends in fintech that have his attention

35:02 – What stands out about the teams at these companies he invests in

36:37 – Thoughts on fractionalization plays

            36:44 – Capital Allocators podcast episode

            36:54 – Venture Stories Podcast

40:03 – Any major trends that are changing and worth attention

            42:06 – The Tipping Point: How Little Things Can Make a Big Difference

43:26 – His take on the media landscape

45:10 – Kindest thing anyone has done for him

 

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

Oct 16, 2018

My guests this week are Ali Hamed, Brian Harwitt and Marc Porzecanski who work together at CoVenture Credit. When I first had Ali on as a podcast guest, we discussed the many aspects of what his firm does, ranging from venture, to crypto, to credit. We glossed over the lending side of the business, but having since learned a lot from them on the topic, I was excited to get the chance to talk with members of their credit team for today’s longer exploration of esoteric high yield lending.

I am always proselytizing the value of investor education, s this week we have a podcast first. The CoVenture team has prepared a long series of posts that correspond to our conversation and go even deeper into the topic of credit investing. You can find them in the shownotes at investorfieldguide.com/credit

This is entirely differently from any conversation I’ve shared before, so I hope you learn as much as I did. Please enjoy my discussion with team CoVenture Credit.

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

1:42 - (First Question) – The formation of their unique credit business

7:09 – Their advantage in seeing both the equity and credit side of their investments

10:23 – Looking at the Returnly deal as an example

14:07 – How they view these deals and are able to sustain them as long-term investments

18:09 – Their interest in payroll deduction lending

20:08 – Finding unique types of default risk

21:31 – What stands out in a platform that makes CoVenture want to take a deeper look

26:43 – Most interesting types of problem they have come across that they have yet to do a deal in

31:35 – What is going to change to make for more thoughtful underwriting of subprime lending

35:51 – Major structures of asset backed lending

39:49 – Whether the home serves as an interesting playground for credit opportunities and whether people will own anything again

42:44 – Mark’s experience working at a huge firm vs his experience at CoVenture

44:31 – How does the current credit cycle impact their view

47:04 – Lending against bitcoin

50:06 – Who is interested in these loans against bitcoin

50:57 – How to set interest rates against a weird asset like this

53:00 – What are the key determents of success in this business

1:02:27 – Kindest thing anyone has team for the team

1:03:52 – How to treat people that you pass on

 

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

Oct 9, 2018

My guest this week is Saifedean Ammous, author of the book the Bitcoin Standard. This was one of the more interesting conversations I’ve had in the world of cryptocurrency, primarily because we don’t talk about Bitcoin or Crypto until 25 minutes into the talk. Instead, we focus on history, economics, sound money, low time preference, and gold—all interesting topics.

Saif’s thinking on cryptocurrencies other than bitcoin—which is that they are worthless—is unique and thought provoking. His reasoning around why gold shouldn’t be compared to the returns generated by assets like equities was also compelling. If you’ve followed my Hash Power episodes, this is a new a differentiated interpretation of Bitcoin as a technology for the store of value use case. Please enjoy our conversation.

Hash Power is presented by Fidelity Investments

 

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

2:10 - (First Question) – Explain Sound Money

4:25 – Examples of hard vs easy money

7:36 – the even money trap

9:36 – The benefits of hard money vs today’s standards

14:05 – Why this interests him

            14:16 – Gold Wars: The Battle Against Sound Money As Seen From A Swiss Perspective

            14:56 – Democracy – The God That Failed: The Economics and Politics of Monarchy, Democracy and Natural Order

16:17 – Correlation between time preference and people’s ability to succeed in life

19:59 – How money markets worked in the late 18th century vs today

27:57 – How he came across Bitcoin and how he thinks of it as a digital gold

35:42 – How will the world transition to a sound money standard

42:15 – The impacts of hyperinflation on crypto currencies

45:04 – The idea of a orderly upgrade of the world currency

48:20 – His thinking on alternative coins

54:05 – What it takes to compete with bitcoin

1:01:43 – How he diversifies

1:04:35 – Stalling bitcoins demand

1:06:11 – Does he apply his thinking of lower time preference elsewhere in his life

1:07:09 – Kindest thing anyone has done for him

 

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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