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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: 2020
Apr 28, 2020

My guest today is Josh Kopelman, the founder of famed venture capital firm First Round Capital. Prior to starting First Round, which has invested at the earliest stages in companies like Square, Uber, and Roblox, Josh was a three-time entrepreneur, so our conversation spans early-stage investing, business building, and entrepreneurship. I’ll not sure forget his analogy distinguishing between navigators and cartographers, nor the rest of the interesting ideas he shared after seeing and investing in so many great businesses. We also discuss how First Round has bucked the trend to build what I’d call a platform adjacent to the core investing business which does a lot for their entrepreneurs and is a model for other professional investing firms, both in venture and elsewhere. Please enjoy my conversation with Josh Kopelman. 

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

(2:05) – (First question) – How pandemic has impacted their investing strategies

(3:54) – How this stressful environment impacts founders

(6:23) – His early career as a founder and how startup culture has changed

(10:15) – Most important lessons from his entrepreneurial career and building from just an idea

(11:50) – How to analyze a founder

(14:05) – Common disagreements when it comes to deciding on an investment

(15:33) – How many opportunities they evaluate in a meeting

(16:16) – The curvy road to their investment in Roadblox

(17:52) – Whether the concept for a platform is overused

(19:36) – Founders asking what google search they should build on

(20:46) – Solving existing or forecasted problems

(25:39) – How the startup scene is impacted by the huge legacy tech companies

(30:28) – What makes a great early stage investor

(32:19) – Do they focus on founders or themes

(33:19) – Where will valuations and returns come back to after the pandemic

(36:30) – How are business models evolving in technology entrepreneurship

            (36:31) – Matt Clifford Podcast Episode

(39:40) – The Dorm Room Fund

(43:02) – Whether investment funds should have their own platform

(47:31) – Product mistakes in software building

(51:52) – What he’s most excited about for the future

(54:05) – The 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

Apr 21, 2020

My guest today is Manny Stotz, the founder of Kingsway Capital. Manny is one of the leading investors in Frontier Markets, investing in equities in countries like Egypt, Bangladesh, and Pakistan. We discuss the opportunity in these markets from all angles: demographics, valuations, sectors and beyond. It is important to note that we recorded this conversation before COVID, and these markets have fallen 30% without a similar rebound in prices that we’ve seen in the U.S. As you listen you’ll hear why this may be relevant for the companies Manny focuses on and may accentuate the opportunity in Frontier Markets even relative to the numbers quoted in this conversation. Listeners will know my interest in Frontier Markets runs deep, so I was excited to have one of the categories leading investors join me.

Please enjoy my conversation with Manny Stotz.

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

2:07 – (First question) – How Kingsway was conceived, their focus on frontier emerging markets, and his career path

11:57 – What are the best company builders good at when it comes to fostering a brand

18:30 – How country-specific factors impact the tailwind

25:43 – How markets are faring in these special circumstances

32:09 – Building a book in many of the markets they trade-in

37:10 – Understanding your edge in frontier markets, showing up

39:59 – Importance of solid distribution for the companies he invests in

42:12 – Concentration in various markets

44:10 – Moving beyond consumer brands in these markets

47:14 – Some of the most interesting countries they are looking into and the country business model

            47:42 – Guns, Germs, and Steel: The Fates of Human Societies

            47:44 – Civilization: The West and the Rest

            47:46 – Why Nations Fail: The Origins of Power, Prosperity, and Poverty

53:21 – New topics he’s excited to learn about that will impact his business over the next 10-20 years

55:37 – Best way for people to get involved and invest in these markets

58:17 – 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

Apr 7, 2020

My guest this week is Sarah Tavel, a general partner at Benchmark, working alongside past guests Bill Gurley and Chetan Puttagunta. Sarah has a long history as both an investor and as an operator.  She was an early product leader at Pinterest before joining Benchmark. Sarah has become one of my go-to resources for topics like networks, consumer technology, and marketplaces among many other topics. I’ve used her framework for how to think about client engagement, company data, and marketplace liquidity and quality over and over again in my business life. I’m so excited to finally have her on the show.  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

1:24 – (First question) - Lessons learned from watching the food delivery space

5:44 – Hip camp and how they are thinking about the space rental sector

            5:45 - The a16z Marketplace 100

7:47 – Valuing private companies vs public companies

9:37 – Building marketplaces

14:24 – Tipping a market

            14:30 – Bill Gurley Podcast Episode

18:09 – How to incorporate reputation scores into a network

19:55 – Search ranking as a tool for marketplaces

21:00 – Size of marketplaces vs their competitors

22:15 – Niching of marketplaces

            22:21 - Chetan Puttagunta Podcast Episode

23:26 – State of the consumer social sector

27:50 – The LinkedIn problem and how she would build a social platform

30:42 – Things that are piquing her interest in the consumer space

32:20 – Lessons learned about scaling while working at Pinterest

38:42 – Pricing and the marketplace

41:25 – Identifying and optimizing a Core Action in a digital business

44:18 – Accruing benefits and mounting losses as part of the product design

47:48 – Her investment in Reci

52:18 – How should companies gather the best data from their business

56:03 – Lessons to SaaS investing

56:29 – Kindest thing anyone has done for Sarah

57:45 – Most interesting philosophy lesson

            58:09 – Creating a Kingdom of Ends

 

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

Apr 5, 2020

In the midst of the worldwide quarantine, my friend Boyd Varty decided to begin an adventure he has been considering for a long time: a 40 day and 40 night stay in the African wilderness. I’m releasing this short conversation with Boyd to pique your interest in his daily dispatches. He will be taking short audio journal-like recordings and sharing them with the world as he goes. As of today they are several that you can listen to by subscribing to the Track Your Life podcast on Spotify or wherever you get your podcasts. Please enjoy this short chat with my good friend Boyd Varty.

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

(0:31) – The start of his 40-day trip

(1:42) – Origin of the word quarantine and how it led to this journey

(3:07) – History of this idea

(6:14) – The logistics of this 40-day venture

(9:59) – His experience doing this before and how it changed his psyche

(12:07) – What is he most fearful of

(13:22) – How he feels about sharing this experience when he returns

(15:47) – The mental preparation to this journey

            (15:48) – Priya Parker Podcast Episode

            (15:49) – The Art of Gathering: How We Meet and Why It Matters

(17:33) – How can outsiders make a connection to Boyd while he’s in this isolation

(19:55) – How can people actually follow him on this journey

            (20:23) – Track Your Life with Boyd Varty Podcast Apple Podcasts | Spotify

            (20:33) – Instagram - @boyd_varty

            (20:36) – boydvarty.com

            (20:43) – 40daysand40nights.com

(21:05) – The story of the 17 lions

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

Apr 2, 2020

My guest today is with past guest Gavin Baker, the founder and CIO of Atreides Management, LP. We discuss investing during a bear market and the major ways in which the COVID19 outbreak has dramatically altered the investment landscape. Please enjoy my second conversation with Gavin Baker.

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

(1:40) – How he sees the markets right now

(3:06) – How he handles information uncertainty and the value spreads

(5:53) – Trading in today’s market and the volatility

(9:45) – How the economic activity squares with the amount of stimulus being pumped into the market

            (13:11) – Market Wizards: Interviews with Top Traders

(13:56) – Asset tests for individual companies in this environment

            (19:09) – This Time Is Different: Eight Centuries of Financial Folly

(20:45) – His take on software companies during the crisis

(28:57) – Fast pace of change during extreme times of duress

(35:14) – Space as a service

(39:52) – Attention and time inside digital universes and how investors can take advantage

(46:17) – Why chaos is a ladder

            (50:42) – It Was a Very Good Year: Extraordinary Moments in Stock Market History

 

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

Mar 31, 2020

My guest today is D.A. Wallach, one of the more interesting investors I’ve come across. He is the former lead singer of the group Chester French and the former artist-in-residence at Spotify, where he was also an early investor. While he’s also an early investor in companies like SpaceX, his focus the last 5 years has been on early stage health care investing, which is the topic of this conversation. We discuss the entire life sciences and heath care investing ecosystem. This was recorded in the very early days of the Coronavirus outbreak so while we touch on it briefly it isn’t the primary focus, and I intend on returning to more traditional episodes like this one in the coming weeks, meant to be evergreen conversations. Please enjoy my conversation with D.A. Wallach.

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

1:31 – (First question) – Where is interest in healthcare started

4:04 – How to categorize health services

5:13 – The product of medicine

6:56 – How medicine is changing in 2020

10:17 – What is enabling innovation in medicine

12:41 – Manufacturing of solutions, gene therapy example

17:16 – Using CRISPR

19:47 – Pros and cons, and the morality of gene intervention

23:44 – How progress is being made in medical breakthroughs

26:51 – What is the business and investment world seeing on the longevity side

30:15 – What is next in the wearable medical tracking trend

33:04 – The personalization of medical treatments

34:31 – How he thinks about all of this from an investing standpoint

36:37 – Exiting these companies

39:41 – How he thinks about founders in this space

42:35 – Drug prices

            42:46 – The Paradox of Pricing

46:45 – What will lead to a change in the pricing of drugs

49:05 – The delivery side of healthcare

51:09 – Investments that could improve the delivery side of healthcare

53:33 – Thoughts on the anti-interventionist line of thinking in the medical world

57:50 – Lessons from his health portfolio

1:02:33 – Other frontiers that pique his interest, including gut biome

1:06:46 – His career in music

1:08:20 – Lessons he learned during his time in the music industry

1:10:19 – Opportunities in the music industry as an investor

1:12:29 – Kindest thing anyone has done for DA

 

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

Mar 25, 2020

My guest today is Chad Cascarilla, here to discuss some of the tail risks in the economy and markets as of March 24th in the midst of the Coronavirus pandemic. Chad was one of the most successful investors during the global financial crisis with a specialty in the banking and finance systems. He now runs Paxos, a trust company which trades and custodies unique products like pax gold, bitcoin, and other tokenized assets including simple pax dollars. I feel it is important to avoid confirmation bias in times like this and not just talk to people are optimistic or long, and while I still believe this is ultimately a positive and optimistic conversation, Chad acknowledges and outlines scenarios that few are talking about yet in the markets.

 

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

(2:04) – (First question) – Today’s market and the porridge scenario

(7:38) – Risks to the market that people aren’t focused on

(10:54) – What lessons from 2008 do we need to heed this time

(13:07) – How does he think about inflation on the other side of this crisis

(16:02) – What does a too cold recovery look like

(20:35) – Benefits of nationalizing the banks vs pumping liquidity

(24:13) – What does the just right recovery look like

(25:24) – Assets that might be ideal to hold in a too hot or too cold scenario

(29:00) – His take on how Bitcoin has performed during this crisis

(31:53) – The US’s inherent strengths compared to the rest of the global economy

(34:50) – Advice for people

            (38:59) – Paxos.com

(39:48) – What is he monitoring to see which way things shake out

 

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

Mar 20, 2020

My conversation today is with my close friend Brent Beshore. Brent is a private equity investor who owns and interacts with many small businesses, which have been hit especially hard by COVID. We discuss the various impacts that COVID has had and may have on both small business and the private equity investing community. Brent also proposes some policy actions which he thinks may help those most in need. 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

1:13 – (First question) – What Brent sees as the current landscape for small businesses

3:25 – The real problem for small businesses right now

6:02 – How long can small businesses survive these freezes

9:14 – Ideas to help businesses stay afloat during a global shutdown

11:01 – The cost of restarting businesses on the other side of this  

13:41 – Policies that could help

            14:30 – government co-paying some business expenses

            16:05 – Suspending payroll taxes

            16:17 – The small business bond

            18:00 – Wider latitude for banks

20:03 – How effective would Brent’s ideas actually be at lessening the pain

22:41 – A look at how things look in the private equity complex

25:39 – What are the potential opportunities out there

29:24 – What is a balance sheet product

32:00 – How this is personally impacting Brent

34:20 – How this is personally impacting Patrick

35:45 – Importance of relationships for personal health

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

Mar 16, 2020

My guest this morning is Dan Rasmussen of Verdad Capital. Like me, Dan and his firm focus on quantitative research. Just a month before the COVID crisis hit markets, they completely and published a study on investing during periods of market crisis, which is the topic of this conversation. We discuss what works and what doesn’t during and after acute periods of panic in markets. I think you’ll find it extremely informative. Because Dan’s firm and my own share many beliefs about investing and conduct similar flavors of research, I try to offer devil’s advocate questions throughout. Please enjoy.

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

1:54 – (First question) – What he sees in the markets today given the atmosphere right now

4:26 – An overview of their study: Crisis Investing: How to Maximize Return During Market Panics

8:38 – How things get more predictable during crisis

11:15 – The length of these crises and assets they focused on

12:40 – What happens to bonds and credit during these times

15:50 – Geography of crises

18:14 – How does this impact the philosophy of just index investing

20:40 – Positioning of value in this market

27:50 – Lessons from other crises

32:21 – Importance of a blended factor approach

35:44 – Role of momentum

38:10 – What else he is paying attention to during this crisis

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

Mar 13, 2020

My guests today are Bill Gurley and Chetan Puttagunta, both partners at benchmark capital. We review the early stage investing world in the face of coronavirus in a very timely conversation, which is one that will remain valuable once this crisis is done. We discuss enterprise and consumer, funding and growth, and the entrepreneurial spirit in the face of a crisis. Please enjoy.

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

1:44 – (First question) – Landscape for venture capital ecosystem

6:47 – The experience in 2009 and the entrepreneurs that tend to rise to the top

8:24 – The relationship between early stage companies and public investors

10:45 – How this crisis impacts enterprise businesses vs the broader corporate sector

14:46 – Advice for early stage companies in a period like this

18:23 – What Chetan was doing during the last downturn and what he learned during it

20:27 – Early stage vs late stage companies in this environment

            22:57 – On the Road to Recap

23:00 – Benefits of being small in a period like this

25:22 – How portfolio companies are responding and pivoting during this period

29:33 – Best practices for remote companies

31:39 – Themes that stand out during this period

34:51 – Closing thoughts 

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

Mar 13, 2020

My guest in this flash podcast is Bryan Krug of Artisan partners. We discuss what has happened so far in the corporate high yield and investment-grade credit markets, and the loan market. We compare today’s environment to the financial crisis and other past crises with lots of nuances that I hope will be helpful to bond and equity investors. 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

1:08 – (First question) – An overview of what he covers in the corporate credit markets

1:52 – How things have changed in the last couple of weeks

3:56 – Composition of the high yield market

7:07 – Major sectors of the high yield market outside of energy

8:39 – How do they price the risk in securities right now

11:21 – How do they handicap a great unknown

13:00 – Risk for broader contagion in the overall credit markets

14:49 – What’s the downside potential here

16:31 – Potential for upside

18:33 – How does he view companies that are drawing down on their entire line of credit

19:44 – An overview of the loan market

20:42 – What warning signs equity investors should be watching for in the bond markets

21:57 – What do credit spreads look like today compared to before this crisis

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

Mar 11, 2020

This week, I’ll be recording and immediately releasing a series of conversations on business and market reactions to the spread of coronavirus. The conversations will be on oil and gas, corporate credit, and the reaction within the venture capital community. Today’s conversation is with Matt Smith, Ian Singer, and Kobi Platt of Deep Basin Capital. We are investors in Deep Basin, and they were past guests on the podcast. We discuss the new price war in the oil markets and the impact it might have on equities and especially on U.S. oil producers. Please enjoy.

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

1:59 – (First question) – An overview of the global oil market and demand

3:37 – Supply and demand shocks we’ve seen lately

6:22 – What happened this weekend with Russia and Saudi Arabia and why the outcome was so shocking

9:45 – The knock-on effects of this activity on equities

14:24 – Impact on US energy production

18:29 – What other industries will feel the effect of reduced production in the US

20:35 – Defining a price war and how victory is defined

27:53 – Saudi Arabia’s calculus in this energy fight.

31:11 – How does all of this change what factors they use to analyze companies

35:43 – What it actually looks like within the commodities markets to trade energy

40:01 – What uncertainty is most intriguing to each of them

43:00 – The long-term interest in investing in the energy sector

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

Mar 10, 2020

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

Mar 3, 2020

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

Feb 25, 2020

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

Feb 4, 2020

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

Jan 28, 2020

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

Jan 21, 2020

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

Jan 14, 2020

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

Jan 7, 2020

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

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