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

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

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

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

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

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

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

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

My guest this week is Gavin Baker, the founder, and manager of Atreides Management. I met Gavin in the same way I meet many of the most interesting people, on twitter. His focus is on consumer and technology growth investing, which is the topic of our conversation. We discuss many of the largest trends in these sectors, several fascinating investment cases, and also explore the videogame industry in detail—which I found especially interesting. Please enjoy my conversation with Gavin Baker. 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 1:16 – (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 view on 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 allows 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 today and, 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 – the 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   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   All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'shaughnessy asset management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of O'shaughnessy asset management may maintain positions in the securities discussed in this podcast. Clients of the podcast guest’s firm may also maintain positions in the securities discussed in this podcast.

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 into 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   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