Invest Like the Best-logo

Invest Like the Best

Business & Economics Podcasts

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

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


United States


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




Blake Robbins – Investing in Gaming - [Invest Like the Best, EP.180]

My guest today is Blake Robbins, a partner at Ludlow Ventures. We talk about all things video games, including the major companies in the industry, how games monetize, how in-game economies work, how e-sports has evolved, and much more. This is a fast-growing segment of consumer attention and interest, I believe we are in the very early days of gaming going mainstream. I also have a favor to ask. My team and I have built a small survey for Invest Like the Best listeners and if you’ve...


Brad Gerstner – Public and Private Investing - [Invest Like the Best, EP.179]

My guest today is Brad Gerstner, the founder and CIO of Altimeter Capital, a multi-billion dollar technology-focused investment firm. Brad and his team are known for a deep expertise in internet-enabled businesses, including Expedia, Facebook, Uber, and many more. We discuss the evolution of opportunity in this style of investing, including the important shift to private investing, where so much of the value creation now happens. I won’t soon forget our discussion of consumer intent on the...


John Collison – Growing the Internet Economy - [Invest Like the Best, EP.178]

My guest today is John Collison, the Co-Founder of the digital payments company Stripe. Stripe’s mission is to increase the GDP of the internet, a lofty and deeply interesting pursuit. John is clearly a voracious learner across business and investing, which you’ll hear instantly. He started Stripe with his brother Patrick when he was just 19 years old, and has grown it to, at last valuation, a $36B business. In our conversation, we discuss conglomerates, the internet economy, the power of...


Jeremy Grantham – An Uncertain Crisis - [Invest Like the Best, EP.177]

My guest today is Jeremy Grantham. Jeremy is the co-founder and chief investment strategist of Grantham, Mayo, & van Otterloo (aka GMO). GMO, which manages more than $60B for clients, was a firm that helped educate me early in my investing career. They’ve long published thought-provoking research, most of which came from Grantham himself. He is regarded as a highly knowledgeable investor in various stock, bond, and commodity markets, but is particularly noted for his prediction of various...


Ben Thompson – Platforms, Ecosystems, and Aggregators - [Invest Like the Best, EP.176]

My guest today is Ben Thompson. Ben is the author of my favorite business strategy newsletter called Stratechery. He’s also the host of the exponent podcast, and now the Dithering, a podcast he recently launched with John Gruber. I think Ben is among the most interesting business analysts in the world, and I’ve learned from and directly applied many of his ideas. We cover many of the major concepts he’s introduced over the years, including his well know aggregation theory. I think that to...


Shishir Mehrotra – The Art and Science of the Bundle - [Invest Like the Best, EP.175]

My guest today is Shishir Mehrotra and the topic of our conversation is the bundle: offering access to multiple products, services, or providers for a single bundled price. This topic is full of incorrect pre-conceived notions, and as it turns out, the bundle is one of the most powerful ideas in business. Properly harnessed it is good for everyone involved. Shishir explains the ins and outs of bundles in this conversation. Shishir ran product at YouTube for years and sits on the Spotify...


Hamilton Helmer – Power + Business - [Invest Like the Best, EP.174]

My guest today is Hamilton Helmer, the Co-Founder and Chief Investment Officer of Strategy Capital and the author of one of the best business books in history called 7 Powers, which is the topic of much of our conversation. He has spent his career as a practicing business strategist: advising companies, investing based on strategic insights and teaching strategy. In the last three decades, he has also utilized his strategy concepts as a public equity investor. In this conversation we cover...


Tobi Lutke – Building a Modern Business - [Invest Like the Best, EP.173]

My guest today is Tobi Lutke, the co-founder, and CEO of Shopify. This is both a timely and evergreen conversation. Timely, as the world as moved aggressively digital in the past two months, and Shopify powers so much of digital commerce. Evergreen, because while we touch on Covid and the Shopify business, this is much more a conversation on business and personal principles, learning, design, and growth. Tobi is one of the CEO’s I look up to most for the type of company he is building and...


Ali Hamed – An Update on Private Credit - [Invest Like the Best, EP.172]

My guest today is popular past guest Ali Hamed, who joins us for an update on private credit. We discuss what has happened so far, what parts of the market are frozen, and where opportunities may lie. We also talk about how the world has shifted digitally since the beginning of the COVID pandemic. Please enjoy my conversation with my friend Ali Hamed. This episode is brought to by Koyfin. For more episodes go to Sign up for the book club, where you’ll get a...


Chris Bloomstran - An Update on Public Markets - [Invest Like the Best, EP.171]

My guest today for a flash update is Chris Bloomstran, the founder and CIO of Semper Augustus and a popular past guest on the show. We talk about his view on the state of the public equity market, why it will be hard for the market to deliver great returns for the next decade relative to the last, and where opportunities may lie. Please enjoy. This episode is brought to by Koyfin. For more episodes go to Sign up for the book club, where you’ll get a full...


Josh Kopelman - The Past, Present, And Future Of Seed Investing - [Invest Like the Best, EP.170]

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...


Manny Stotz - Frontier Markets Investing - [Invest Like the Best, EP.169]

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...


Sarah Tavel - Consumer & Marketplace Investing - [Invest Like the Best, EP.168]

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...


[BONUS] Boyd Varty - 40 Days and 40 Nights

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...


Gavin Baker – Investing Through a Bear Market - [Invest Like the Best, EP.167]

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 Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month...


D.A. Wallach – Investing in Healthcare - [Invest Like the Best, EP.166]

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...


Chad Cascarilla – Update on Tail Risk - [Invest Like the Best, EP.165]

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...


Brent Beshore – Update on Small Business and Private Equity - [Invest Like the Best, EP.164]

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 Sign up for the...


Dan Rasmussen – Investing Through a Crisis - [Invest Like the Best, EP.163]

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...


Bill Gurley and Chetan Puttagunta – An Update on Consumer & Enterprise Venture Capital - [Invest Like the Best, EP.162]

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 Sign up for the...