168 episodes
Invest Like the Best Patrick O'Shaughnessy
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- Investing
Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at InvestorFieldGuide.com
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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.
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]
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]
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]
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]
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]
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
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.
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
Customer Reviews
A surprise discovery, not really for investing
This is the best show I’ve discovered recently, thanks to Spotify recommendation. I was suspicious at first since I’m not in the finance world, nor close to investing, VC, banking or any of that, though being in the Bay Area. I’m so glad I gave it a try. The title doesn’t do justice for this show. It’s not the investing 101, how to get a job in finance kind of stuff I was expecting, only much better. The host is such a great listener and questioner - asking all the appropriate questions at the right time, and only that. I could feel that his guest is enjoying the conversation as he is, and as I am. It’s authentic, informative, and just at the right level of detail and intimacy. I envy that he knows so many smart and interesting people and gets to have such nurturing conversations. It’s been a feast, thank you all for sharing. I feel inspired and learned after every episode. I so wish to join a live conversation like this someday myself!
Cultivating Conversations | High-Caliber Content
Personal story: After listening to countless episodes, I felt this podcast had earned the right as an “Interest” on my resume. One of the first things my now manger mentioned was this inclusion. He’d just had a friend recommend the podcast to him. I got the job, my first in finance. Appreciate it Patrick.
Official Review: Patrick is a phenomenal communicator and host. After each episode I feel/am a better man for having listened. Regardless of subject (and the variety is brilliant), Patrick and guests never fail to impart high quality wisdom. Have highly recommended and will continue to do just that. Let’s just say, I’m “Interested.”
Broad Discussions About Finance And Tech
By far the most diverse range of interview topics/guests of any investing podcast. Patrick is great at sitting back and letting his guests do the talking. Random tangential interviews along with deep dives into private businesses, blockchain technology, and Fintech’s future; it’s a joy to start each new podcast. The enjoyable meandering path of the podcast seems to mimics Patrick’s own journey of learning and networking in the investing world.
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