Patrick O'Shaughnessy's Blog, page 7
March 3, 2020
Jeff Lawson – How to Build a Platform – [Invest Like the Best, EP.158]

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

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

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.
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 – Business model of open source software
1:15:54 – Being default open
1:17:53 – Kindest thing anyone has done for Chetan
January 13, 2020
Matt Clifford – Investing Pre-Company – [Invest Like the Best, EP.154]

My guest today is Matt Clifford. He’s the cofounder 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 cofounder, 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.
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 – 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
January 7, 2020
Peter Buffet – Finding Your Note – [Invest Like the Best, EP.153]

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 ones 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 Peters 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
1:02:24 – 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
December 17, 2019
Ben Savage – All Things Fintech Investing – [Invest Like the Best, EP.152]

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

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. You can find links to his book and podcast in the show notes.
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!
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
19:21 – Understanding one’s own biases
24:04 – How he became VP of analytics at Twitter
28:37 – Primary lessons from the work evaluating human
capital and talent with analytics
28:59 – Niel Roberson Podcast Episode
31:40 – How to model people for success when hiring
33:29 – How to hire the right data scientists’ team
37:54 – Most interesting problems they tackled at twitter
42:31 – Responsibility of social platforms to police itself
45:34 – Areas that would interest him in the future as an
investor
49:24 – Kindest thing anyone has done for Jeff
51:50 – Values instilled in him by his parents.
December 3, 2019
Vaughn Tan – Quality and Innovation – [Invest Like the Best, EP.150]

My guest today is Vaughn Tan, who studies quality, innovation, and organizational behavior. His resume is bonkers. He’s a PhD from Harvard, Was an infantry signals logistician in the Republic of Singapore Army, then worked at Google on advertising, Earth, Maps, spaceflight, and Fusion Tables. He’s also been a wood sculptor.
But the topic of our conversation is how to foster quality and innovation in ourselves and inside of companies—lessons he learned in part by studying inside some of the world’s best restaurants.
If you enjoy this conversation, I recommend you also check out his new book, The Uncertainty Mindset Innovation Insights from the Frontiers of Food. Please enjoy my conversation with Vaughn Tan.
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
1:33 – (First Question) – Interesting ways to identify high quality
5:06 – The current problem with the way we think about the world
8:56 – How people think about their careers and college
11:21 – Uncertainty vs risk, and productive discomfort
19:08 – Cultivation of discomfort for an individual
24:05 – Successful innovation cultures
32:25 – Analyzing quality and restaurant bread
37:43 – The Slug idea
40:43 – His research project where he observed restaurants
45:44 – How do people mandate their own structure in the face of uncertainty
53:46 – How employees should approach this rent-to-buy hiring structure
57:17 – Example of someone who took advantage of uncertainty time
1:00:05 – Playful adults
1:00:07 – Jerry Neumann Podcast Episode
1:03:10 – Other changes companies can make to their culture to be more innovative
1:08:19 – The difference between simplicity and complexity
1:11:12 – How he applies his thinking into several different ideas, like Cannabis
1:16:17 – Asking the right question
1:19:05 – Andy Rachleff Podcast Episode
1:20:19 – Kindest thing anyone has done for Vaughn
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
November 26, 2019
Gavin Baker – Tech and Consumer Growth Investing – [Invest Like the Best, EP. 149]

My guest this week is Gavin Baker, the founder and manager of AtreidesManagement. I metGavin in the same way I meet many of the most interesting people, on twitter. His focus is onconsumer and technology growth investing, which is the topic of our conversation. We discussmany of the largest trends in these sectors, several fascinating investment cases, and also explorethe videogame industry in detail—which I found especially interesting. Please enjoy myconversation with Gavin Baker.
Notes1:16–(first question)–His unique view on the markets
4:00–Distilling Apple as a growth investment
6:44–What is the most important lever for Apple looking forward
9:01–His viewon Intel
11:03–Most important technological changes that may dictate his investing strategy
16:20–How do you look at a big idea, like AR, and then apply to an individual business
18:21–Fortnite isn’t a game, it’s a place
18:26–Fortnite Is the Future, but Probably Not for the Reasons You Think
18:56–His insight into video games and their ability to control attention
28:36–How do you invest in the gaming sector
40:06–Favorite video games
32:07–Why gaming and customer sector allow him to find Alpha richness
34:17–Being in the top 1% of knowledge before investing in a company
36:24–His view on value investing todayand, in the future,
41:15–Increase of regulatory capture
42:01–Headwinds to the tech companies today
43:50–Thoughts on the Chinese internet market and how it impacts US markets
45:36–How often companies look at China for ideas
46:21–Role of alternative data in his process
49:36–Big trends today we should be paying attention to
54:20–most interesting company he does not own
58:48–Advice for new investors
1:00:17–Non-obvious tech resources-TechMeme
1:00:50–Favorite sci-fi character
1:01:19–Kindest thing anyone has done for him
November 19, 2019
Kevin Systrom and Mike Krieger – How to Build a Great Product – [Invest Like the Best, EP. 148

My guests this week are Kevin Systrom and Mike Krieger, the co-founders of Instagram.
I met Kevin and Mike a few months ago over a shared interest in business and investing. I have found them both to be extremely good people who have a rare talent for finding and solving interesting problems. Indeed, problem solving and jobs-to-be done is a big part of our conversation.
I realized walking into the podcast that Kevin and Mike have a rare set of experiences: having both built and sold an extremely successful product from scratch, but then also operated and scaled inside one of the largest businesses in the world. This means they have unique knowledge to offer just about anyone interested in business and products. We dig in to all those lessons here.
I am working on hosting more founders and CEOs on the podcast, and can’t think of a better pair to show you why I want to do so. Please enjoy my conversation with Kevin and Mike.
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
1:38 – (first question) – Projects they’ve been working on since leaving Instagram
5:22 – How they can apply what they are learning in machine learning
7:18 – Most interesting experience diving back into data and machine learning
8:42 – How startups compare today to when they founded Instagram
13:23 – Judging founders and whether they know how to use their data effectively
14:26 – The jobs-to-be-done framework
19:14 – Laying out a vision vs solving problems that pop up
25:20 – Developing and sharing the principles of the company with the team
30:48 – Creating a community when it includes almost the entire world
39:03 – The most popular ways people used the platform
41:24 – What was the jobs-to-be-done rational behind the stories feature
44:15 – Interesting things that they saw as Instagram entered the developing world
46:40 – Their thoughts on how Instagram shaped culture and if they focused on those
52:58 – The new waves that they are observing right now
55:11 – How their thinking on leadership and teams changed during their time at Instagram and Facebook
1:03:23 – The pillars of a good business, including humility and confidence
1:06:06 – Focus on growth and distribution in a startup
1:10:01 – How early were they thinking about monetization on this free platform
1:13:43 – How do they think about how they invest their money and allocate resources
1:17:36 – Mentors for Kevin and Mike
1:20:30 – Their passion for learning to fly and the someday/maybe list
1:23:01 – Their interest in coffee
1:26:24 – Advice for everyone else
1:30:00 – Kindest thing anyone has done for them