My guest today is Laura Behrens Wu, co-founder and CEO of Shippo. Shippo started in 2014 after Laura realized with her own e-commerce start-up that shipping was an incredibly difficult task for most merchants, so she set out to fix the problem for everyone. Shippo let's merchants small and large use its dashboard or APIs to simplify the shipping and tracking process. Our conversation focuses on Laura's background prior to Shippo, how Shippo's business and business strategy have evolved, the inherent challenges of building a shipping platform, and the intersection of the physical and digital worlds. I hope you enjoy our wide-ranging conversation.
This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out.
This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(2:57) – (First question) – The story of Popout and how it led to Shippo
(7:40) – Challenge of working in a huge and crowded market
(10:36) – How Shippo changed shipping for small businesses
(12:30) – First big break in their favor
(13:39) – Their master account with the major shipping companies
(14:39) – Why is the shipping industry so complex
(16:25) – Most painful part of building Shippo
(18:20) – Advice for people in early company building
(19:26) – Pricing software in early days
(20:32) – The early days of Shippo and getting it to where it is today
(23:17) – Going to market and targeting new customers when they’re mostly small businesses
(25:48) – Partnering with a larger company, in their case Shopify
(27:52) – How they think about their long-term planning
(30:48) – Competing in a world where companies can own their own infrastructure
(32:39) – How often they think about other competitive advantages
(34:20) – Worst question an investor asked her: what if Amazon tries to copy them
(35:17) – Her superpowers as a founder
(36:41) – API vs dashboard and the difference in their customer bases
(38:52) – What businesses that need shipping today need to know
(40:14) – Changes in how businesses are being built today
(41:28) – What excites her most about the future of this business
(43:28) – Kindest thing anyone has done for her
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
My guests today are Rich Barton and Brad Gerstner. Brad is the founder of Altimeter Capital and is one of my favorite active investors. Brad and Altimeter were one of the largest investors in Snowflake in its earlier days and continue to invest in iconic modern businesses with an extreme focus. Rich has one of the most impressive resumes in the business world. He founded Expedia, Glassdoor, and Zillow; He’s a longtime Netflix board member, since before they went public; he’s a venture partner at Benchmark Capital; and he give back through the Barton family foundation. Our conversation covers Rich’s “power to the people,” strategy, Brad and Rich’s perspectives on taking companies public through SPACs vs. IPOs, and their perspectives on how to build a great company. This one is so fun, we even discuss how to come up with company names, talk about the importance Wizard of Oz, and explore the importance of big hairy audacious goals. I really enjoyed this conversation with two of the smartest people I know, and I hope you will too.
This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin.
Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com
This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.
With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(2:59) – (First question) – How Brad and Rich met
(5:57) – The instant click between them
(7:21) – The power to the people perspective
(7:29) – Brad Gerstner Podcast Episode
(10:21) – Delivering information to consumers
(11:31) – The investing perception of data-delivery businesses
(13:54) – How they use SPACs
(17:38) – How entrepreneurs view SPACs
(20:17) – Lessons from their involvement in Altimeter Growth Corp
(23:57) – Defining value add investor in the public and private markets
(26:36) – The Wizard of OZ and Pygmalions
(30:41) – Leadership mold at businesses and big audacious goals
(30:44) – No Rules Rules: Netflix and the Culture of Reinvention
(36:05) – Frank Slootman’s leadership style
(36:12) – Amp It Up
(46:13) – TAPE SUCKS: Inside Data Domain, A Silicon Valley Growth Story
(38:11) – Courage in leadership
(41:33) – Physical businesses vs digital only businesses
(43:34) – Getting companies fit
(45:39) – Lessons around talent density
(48:28) – State of the world and markets today since the inception of the pandemic
(53:46) – Making up words for companies and fertile ground
(56:45) – Go to market model vs business model
(58:50) – Early days of product market sales
(1:03:03) – Advice to early investors and entrepreneurs for the future of their careers
(1:08:10) – The board challenge
(1:12:06) – What question are they working hard to answer right now
(1:16:09) – Kindest thing anyone has done for Rich
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
My guest today is Jason Citron, founder and CEO of Discord. Discord is one of the largest and fastest growing social networks in the world. It started as a place for gamers to congregate online, but thanks to how easy it makes it to create a community of any type and its offering of text, audio, and video as means of communication, it has expanded far beyond gaming. It has the potential to become the default digital “third place” that we go to find belonging in a variety of online communities. With over 100 million users, it’s also one of the most interesting communications service businesses since the original social networks rose to power.
Our conversation focuses on his background prior to Discord, Discord’s founding and growth, its business model and how it has evolved over the past 8 years, and what the future holds for Discord. As we talked, I had this sense that I’d be willing to go work for Jason, and I think you’ll see why. I hope you enjoy our wide ranging conversation.
This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out.
This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(3:17) – (First question) – Lessons from his time as a video game developer
(7:58) – Going from game developer to game development platform
(12:23) – From his first startup to Discord
(16:33) – Expressing the hypothesis of discord
(20:10) – How to know what signal to build upon
(22:11) – Early adoption of Discord
(26:17) – Getting the word out about Discord in the early days
(30:43) – Creating more than just a platform, but creating a third place for people to congregate
(32:55) – The evolution and expansion of the types of community using their platform
(37:27) – Discord’s business model and how it’s evolved
(41:32) – Enhancing communication through Nitro
(45:05) – Big principles for company building at Discord
(51:22) – His thoughts around competitive advantage for the platform
(52:55) – Creating a holistic experience for the users
(55:45) – What bothers him the most when hiring
(57:47) – Kindest thing anyone has done for him
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
My guests today are Ben Gilbert and David Rosenthal. Ben and David are investors but also the duo behind the Acquired podcast, which is one of my favorite podcasts that dives deep into business history and famous acquisitions. I recommend you check it out.
In this conversation, we review of some of the greatest corporate acquisitions of all time and also discuss investing lessons Ben and David have learned across their careers. I hope you enjoy my conversation with Ben and David.
This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin.
Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com
This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.
With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee.
Learn more and try Assure for yourself at https://www.assure.co/patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(2:29) – (First question) – What they look for in new founders based on more experienced managers they’ve worked with
(5:07) – Difference between emerging vs legacy market
(9:17) – Research steps to determine if a market can get big enough to invest in
(12:08) – Working with other firms for doing an initial investment round
(15:42) – Recent trends in the supply of capital and number of founders in the VC space
(18:56) – Lessons they have learned studying corporate transactions
(24:13) – How do startups transform once they are acquired to increase their multiples so much
(28:10) – What they learned from deliberations that take place within the acquiring company
(30:39) – Most interesting deal for them to unpack
(32:44) – What are features of a business that is difficult for others to replicate
(35:52) – Any company that are intimidated to go up against
(37:37) – Who would they follow
(38:52) – Blake Robbins Podcast Episode
(39:09) – Missing pieces in their skill set
(41:43) – Early green shoots
(44:40) – Lessons from Alaska Airlines acquisition and the value of scarcity
(47:07) – Kindest thing anyone has done for them
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
My guest today is Leore Avidar. Leore is the co-founder and CEO of Lob, a company which makes it easy to send direct mail programmatically. He’s also the founder of a new company focusing on sports card collectibles, Alt, which is how we originally connected. Our conversation ranges from building Lob, buying a Lebron James rookie card, starting a 2nd business while operating his first and how Leore tries to create and sell superpowers. Like my conversation with Rahul Vohra from Superhuman, I think this conversation will inspire entrepreneurs out there to start building aggressively. Please enjoy.
This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out.
This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(2:55) – (First question) – Origin of Lob
(6:14) – Creating and selling superpowers to other people and its value proposition
(7:23) – Defining an API in his words
(8:44) – Early breaks for Lob
(10:45) – Early lessons in responsible growth
(12:19) – Physical infrastructure behind Lob
(14:14) – Surprises in mail delivery
(15:00) – Progression through their pricing models
(18:10) – Leaders in the world of making the world programmable
(19:07) – Their interest in the physical world
(19:45) – Hardest part of scaling a physical business
(21:09) – Building a culture that keeps people around
(23:13) – Why he is fascinated by negotiations and what he’s learned from it
(25:20) – Scarcity, time, and leverage impact’s on negotiations
(26:35) – His interest in collectibles and the formation of Alt
(30:18) – Size of the alternative market he focuses on
(30:54) – The focus on cards
(32:18) – An overview of collectible cards industry
(33:19) – What is the API of card collection and trading
(35:51) – Competitors in the space
(37:19) – Buying a Lebron James card
(38:21) – Building a fund around the collectibles and the strategy
(39:45) – What it means to be a technology company
(40:23) – Collectibles beyond sports
(41:30) – Defining a good investor
(43:32) – Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts
(43:43) – Qualities he looks for in investors
(45:03) – What does the collectible universe look like over the next 5-7 years
(45:43) – Cultural value of assets
(48:50) – Managing his time while launching two businesses
(49:51) – What he’s most excited about over the next 6 months
(51:45) – Consolidation of API businesses
(52:19) – Kindest thing anyone has done for him
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
My guest today is Jacqueline Novogratz. Jacqueline is the founder and CEO of Acumen, a non-profit global venture fund that uses entrepreneurial approaches to solve the problems of poverty. Our conversation touches on how Jacqueline left Wall Street and ended up starting a micro finance bank in Rwanda, how she thinks about investing in character, how creating dignity plays such a major role in her investments, and how governments and businesses can work together to solve the world's toughest problems. It is a bit of a departure from my normal investing conversations but contains powerful lessons for many investors and builders. I really enjoyed our conversation and hope you will to.
This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis.
If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(2:29) – (First question) – Where the concept of the blue sweater came from for her book.
(2:44) - The Blue Sweater: Bridging the Gap Between Rich and Poor in an Interconnected World
(4:29) – Every child has a humiliated experience and the impact on their life
(6:55) – The origin of Acumen
(10:42) – Why character is such an important investing filter for her
(11:59) – How the markets have changed through the lens of Acumen
(16:59) – The challenges of getting started
(17:04) – Manifesto for a Moral Revolution: Practices to Build a Better World
(19:46) – Embracing the idea of being uncomfortable and an example for her
(21:50) – The space between government action and market action
(26:11) – The concept of conformity traps
(29:29) – The lens of moral imagination
(30:32) – The importance of brining dignity to others
(35:09) – Entrepreneurial skills she sees outside of the US that we lack here
(39:38) – Biggest problems across the globe she is interested in tackling
(42:48) – Impediments to investing in global problems
(49:11) – Kindest thing anyone has done for her
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
My guest today is Justin Singer, the founder and CEO of Caliper Foods and Stillwater Brands, two leading companies in the cannabis industry. We start our conversation with a fascinating discussion on how regulation creates or destroys business and investing opportunities, and then go on to discuss the ins and outs of the cannabis industry in detail. You’ll be able to tell quickly how high-quality Justin is as a thinker and operator, and you’ll learn a ton about this nascent business. Please enjoy our conversation.
This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out.
This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(2:51) – (First question) – How changes in regulation create market opportunities
(5:38) – Why VC’s need to pay attention to regulatory changes
(6:50) – Story of Section 230 of the communication decency act
(8:54) – Relationships between rules, laws, and free markets
(11:56) – How regulatory changes impacted recent business ventures
(13:30) – His initial interest in the cannabis space
(17:28) – How the industry participants have changed over time
(21:04) – An overview of the cannabis industry and different pieces of the chain
(25:51) – What has led to delays in the legalization of the marijuana industry
(28:52) – How the dosage of the product impacts the business
(31:34) – CBD vs THC industry differences
(32:53) – How much of this industry is left to be unlocked and potential timing
(35:55) – Business and investing opportunities in the space
(38:16) – Competitive frontier in cannabis
(40:37) – The timeline and pending changes coming
(43:03) – Margins and business factors of his business
(45:51) – First big break for the business
(49:47) – What he learned working under Tim Wu
(50:34) – Why we are in the golden error for fraud
(52:11) – Avoiding fraud
(55:12) – What he wants to learn more about in the cannabis space
(56:50) – Kindest thing anyone has done for him
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
My guest today is Jesse Livermore. I’ve worked with Jesse as part of our research partners program at O’Shaughnessy Asset Management for years now. Whenever there is a huge, important, and complex issue to be studied, I believe he’s among the best minds in the world to tackle it. He did that recently on the topic of what he calls “upside down markets,” which is the topic of this conversation. We seek to answer the simple question: against a horrible economic backdrop, how can the stock market be near all-time highs? Jesse explains in detail the impact that fiscal policy has had on the market and may have in the future. Please enjoy this master class in upside down markets.
This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis.
If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(2:29) – (First question) – What is Upside Down Markets
(5:44) – Overview on monetary easing and the fed’s role in the markets
(9:42) – Why fiscal policy is such an important lever and the impact it has on the economy
(15:07) – The impact of stimulus on public companies’ fundamentals
(19:25) – The mix of assets in the market due to stimulus
(22:13) – What made 1929 so different to how we are reacting today
(26:14) – Negative concerns: too much money in the system and the risk of inflation
(32:43) – Will the pendulum swing back to labor and higher wages
(37:23) – How these changes could impact specific companies or sectors differently
(41:34) – How he is applying all of this to his personal investment philosophy
(44:25) – Biggest risks still out there
(49:51) – Most interesting gap in his knowledge putting together this piece
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Today’s episode represents a new chapter for Invest Like the Best, so requires a longer introduction than normal. Starting today, I’ll be bringing you two episodes per week on the same feed. On Tuesday’s, I’ll focus on investors, and on Thursday’s, I’ll host builders—founders, CEOs, and operators from all different fields. We call this new Thursday series Founder’s Field Guide. There’s nothing more interesting to me than how great businesses get build, and how investors can identify those businesses at the right time. We’ve already recorded with founders build companies in food, technology, infrastructure, shipping, collectibles, and many more categories. The goal each weak will be to have a builder share what they’ve done, how they’ve done it, and what they’ve learned along the way. We view this as a critical next step in furthering our mission: to capture and openly share the world’s best knowledge on business and investing.
Onto the kickoff episode with Rahul Vohra. Rahul is the Founder & CEO of Superhuman, an extremely popular product for managing email. Rahul describes himself as a Computer Scientist, Gamer, Entrepreneur, and Designer. You’ll see quickly why it’s the intersection of these areas that sets Superhuman apart. We discuss why emotion matters when building products, and how other entrepreneurs can learn from his experience. Please enjoy the very first episode of Founder’s Field Guide, and stay tuned in future weeks as we host leaders from Nike, Cisco, Twitch, and so many more…listen in as we explore the world of cannabis, baking (not that kind), manufacturing, hardware, software, and more. Let’s dive in.
This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out.
This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
(3:56) – (First question) – His interest in game design and emotion in software creation
(5:15) – Key elements of game design
(6:23) – Toys in digital software creation
(8:48) – Finding success in boring software solutions
(11:19) – Getting confidence while building when there are no real customers
(14:08) – How they landed on their final product
(15:40) – The Superhuman Product/Market Fit Engine
(20:46) – Determining software price
(21:55) – Positioning Your Startup is Vital — Here’s How to Nail It
(23:09) – Positioning: The Battle for Your Mind
(24:13) – Monetizing Innovation: How Smart Companies Design the Product Around the Price
(26:36) – First big break for the business
(29:04) – How technology companies actually grow
(32:15) – Branding a software
(33:57) – How he evaluates a company brand as an investor
(36:07) – Questions to ask founders when considering an investment
(37:35) – How the distribution of Superhuman worked so well
(41:25) – Most common question asked by VC’s about Superhuman
(43:00) – Why they do manual onboarding of customers
(43:05) – Daniel Ek Podcast Episode
(45:10) – Cost structure of a busines looking to reach the billion-dollar valuation
(47:18) – Designing for flow in software business
(51:21) – His design philosophy and their joy formula
(58:03) – His superpower
(1:00:46) – The power of therapy
(1:02:50) – Why he invests in other companies
(1:05:05) – Trends in the technology space that have him excited
(1:07:28) – The future for Superhuman
(1:10:26) – Kindest thing anyone has done for him
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag