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. 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. NPR releases an episode of Planet Money twice a week, although new episodes are sometimes interspersed with classic episodes from the vault. The CBOE Volatility Index gets a lot of attention in times of uncertainty. This episode of Invest Like The Best is also sponsored by Assure. All of it, with a straightforward one-time fee. From bootstrapping a business to scale with MailChimp CEO Ben Chestnutt to the formula for great hiring with Aneel Bhusri, co-founder and CEO of Workday (NASDAQ:WDAY), each episode provides a unique insight into the growth of a company. This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I recommend you check it out. Motley Fool Money is a rundown of all the stock market news to close out the week, served with a side of commentary from the Fool’s expert analysis team. Canalyst is the leading destination for public company data and analysis. 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 Podcasts are an amazing resource for crafting your own investing strategy. All of it, with a straightforward one-time fee. The economy explained. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. 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. His diatribe of Adam Neumann and the shambles at WeWork sheds an unblinking light on the corporate governance which led to the company’s downfall. BFFs featuring Josh Richards and Dave Portnoy, Rob Bence and Rob Dix from The Property Hub, The Meaningful Money Personal Finance Podcast, We Study Billionaires - The Investor’s Podcast Network. Their personal journeys, the roadblocks involved in starting your own business and what they had to overcome to turn both themselves and their businesses into what they are today. If you love finance, investing, life - sit back and enjoy. He also boasts a seat on the boards of Airbnb, Convoy, Edmodo, and Microsoft (NASDAQ:MSFT). Very diverse and rich in content. It all comes together smoothly and seamlessly, quite like the right bourbon! Follow Patrick on Twitter at @patrick_oshag, Ben Gilbert and David Rosenthal of Acquired - Lessons on Early Stage Investing and Getting Acquired, My guests today are Ben Gilbert and David Rosenthal. "Invest Like the Best" This podcast is for the serious investor, as host Sean O'Shaughnessy talks money and investing with some of the sharpest minds on Wall Street. 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             (32:38) – The Great Good Place: Cafes, Coffee Shops, Bookstores, Bars, Hair Salons, and Other Hangouts at the Heart of a Community (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 With Assure, investors can eliminate nearly all the admin cost of private investment. 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 With Assure, investors can eliminate nearly all the admin cost of private investment. They break down any and all mitigating factors that may influence Wall Street and the impact it will have on investors. How Will A Stimulus Deal Affect the Stock Market? Stocks, stocks and more stocks. It has the potential to become the default digital “third place” that we go to find belonging in a variety of online communities. This episode of Invest Like The Best is sponsored by Canalyst. In the podcast’s own words “Reid Hoffman sets out to describe and prove theories that explain how great entrepreneurs take their companies from zero to a gazillion in ingenious fashion.” Because of this, each episode has a unique outlook based on the theory at hand. Sign up for the book club and new email newsletter called “Inside the Episode” at If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. First-time listeners don’t be deterred when you tune in to hear about hiring strategies and are welcomed with how to distill bourbon. Plugging into Business Daily on your morning commute is a surefire way to start thinking like an investor. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. With each passing year, more good podcasts emerge, from well-known brands such as Schwab’s “Choiceology” with Katy Milkman to smaller shops like George Grombacher’s “Money Savage… In our wholly unbiased opinion, it is the best investing podcast out there. A simple mission, an elaborate execution. This episode is also sponsored by Vanta. Its range of topics and level of detail is extraordinary. He is one of our favorite commentators here at MyWallSt and will soon be yours too. MyWallSt staff currently holds long positions in companies mentioned above. Learn more and try Assure for yourself at Like my conversation with Rahul Vohra from Superhuman, I think this conversation will inspire entrepreneurs out there to start building aggressively. He’s also the founder of a new company focusing on sports card collectibles, Alt, which is how we originally connected. For … With over 100 million users, it’s also one of the most interesting communications service businesses since the original social networks rose to power. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. Do Recent Results Make Pinterest A Buy Right Now? Patrick listens intently and asks his guests meaningful questions with genuine interest in feeding his voracious appetite for learning. Jacqueline is the founder and CEO of Acumen, a non-profit global venture fund that uses entrepreneurial approaches to solve the problems of poverty. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. 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 episod, Jason Citron - Building the Third Place - [Founder’s Field Guide, EP.4], My guest today is Jason Citron, founder and CEO of Discord. 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

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