Invest Like the Best

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


Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, EP.181]

Jul 7, 2020
66 min
My guest this week is Charlie Songhurst, the former head of strategy at Microsoft and a prolific investor, having personally invested in nearly 500 companies throughout his career. I met Charlie at an event hosted in New York and you can tell...
Jul 7, 2020 • 66 MIN

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

Jun 30, 2020
56 min
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...
Jun 30, 2020 • 56 MIN

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

Jun 23, 2020
69 min
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,...
Jun 23, 2020 • 69 MIN

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

Jun 16, 2020
81 min
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...
Jun 16, 2020 • 81 MIN

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

Jun 9, 2020
68 min
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....
Jun 9, 2020 • 68 MIN

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

Jun 2, 2020
77 min
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...
Jun 2, 2020 • 77 MIN

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

May 26, 2020
71 min
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,...
May 26, 2020 • 71 MIN

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

May 19, 2020
58 min
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...
May 19, 2020 • 58 MIN

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

May 12, 2020
65 min
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. ...
May 12, 2020 • 65 MIN

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

May 5, 2020
44 min
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...
May 5, 2020 • 44 MIN

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

Apr 30, 2020
58 min
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...
Apr 30, 2020 • 58 MIN

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

Apr 28, 2020
55 min
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,...
Apr 28, 2020 • 55 MIN

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

Apr 21, 2020
60 min
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...
Apr 21, 2020 • 60 MIN

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

Apr 7, 2020
60 min
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...
Apr 7, 2020 • 60 MIN

[BONUS] Boyd Varty - 40 Days and 40 Nights

Apr 5, 2020
24 min
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...
Apr 5, 2020 • 24 MIN

Gavin Baker – Update of the Bull Case for Equities - [Invest Like the Best, EP.167]

Apr 2, 2020
53 min
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...
Apr 2, 2020 • 53 MIN

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

Mar 31, 2020
75 min
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...
Mar 31, 2020 • 75 MIN

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

Mar 25, 2020
43 min
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...
Mar 25, 2020 • 43 MIN

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

Mar 20, 2020
38 min
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...
Mar 20, 2020 • 38 MIN

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

Mar 16, 2020
43 min
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...
Mar 16, 2020 • 43 MIN

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

Mar 13, 2020
38 min
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...
Mar 13, 2020 • 38 MIN

Bryan Krug – An Update on Corporate Credit - [Invest Like the Best, EP.161]

Mar 13, 2020
27 min
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...
Mar 13, 2020 • 27 MIN

Deep Basin – Oil Price War and Its Implications - [Invest Like the Best, EP.160]

Mar 11, 2020
50 min
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...
Mar 11, 2020 • 50 MIN

Peter Zeihan - Dis-United Nations - [Invest Like the Best, EP.159]

Mar 10, 2020
63 min
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...
Mar 10, 2020 • 63 MIN

Jeff Lawson – How to Build a Platform - [Invest Like the Best, EP.158]

Mar 3, 2020
52 min
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...
Mar 3, 2020 • 52 MIN

Niko Canner – Become a Perfect Instrument - [Invest Like the Best, EP.157]

Feb 25, 2020
52 min
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...
Feb 25, 2020 • 52 MIN

[REPLAY] What You Learn About Business Deals After: 12,000 Deals Reviewed, 1,500 Deep Dives, 125 Site Visits, and 7 Portfolio Companies with Brent Beshore - [Invest Like the Best, EP.100]

Feb 4, 2020
51 min
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...
Feb 4, 2020 • 51 MIN

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

Jan 28, 2020
80 min
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,...
Jan 28, 2020 • 80 MIN

Rebecca Kaden – Thesis Driven Investing - [Invest Like the Best, EP.155]

Jan 21, 2020
54 min
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...
Jan 21, 2020 • 54 MIN

Matt Clifford – Investing Pre-Company - [Invest Like the Best, EP.154]

Jan 14, 2020
74 min
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...
Jan 14, 2020 • 74 MIN