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Invest Like the Best with Patrick O'Shaughnessy

Latest episodes

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Jan 30, 2018 • 45min

Anthony Pompliano - Full Tilt Investing- [Invest Like the Best, EP.74]

My guest this week is Anthony Pompliano. Pomp began his career in the military, and has since been a successful entrepreneur, worked as a head of growth at Facebook, and started Full Tilt Capital, an early stage investing firm in North Carolina. This conversation has three memorable sections. Early on, we discuss the four traits Pomp looks for in founders, which we cover in detail. These double as traits that are important when hiring anyone. Next, we discuss his unique take on cryptocurrencies, where he is excited about the prospects for tokenized securities. Finally, we explore a unique media company, Bar Stool Sports, and what makes it such a powerful brand. Please enjoy our somewhat abbreviated discussion and know we will continue the conversation soon. 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   Links Referenced Dave Portnoy and Barstool Sports’ Secret Billion Dollar Plan Books Referenced Win Bigly: Persuasion in a World Where Facts Don't Matter   Show Notes 2:06 - (First Question) – Recap of Anthony’s military career 4:07 – Most memorable experience while deployed 5:27 – Transition out of the military and how it shaped his investing philosophy 11:19 – investing philosophy of Full Tilt, starting with deal economics 10:00 – Attributes of an ideal founder 13:50 -  Where you actual learn the attributes that make you a good founder 14:40 – Time that Anthony has taken the biggest risk in life 16:45 – What is the viewpoint that Full Tilt has today that gives it Alpha in the market 18:47 – Why tokenized securities could be advantageous for investors in a company 19:51 – Anthony’s explanation of a tokenized security and what needs to happen for this idea to be fully realized in the market 22:22 – What could be the impact on the markets of making liquidity in venture so readily available 24:39 – What are tokenized securities actually invested in in the real world 27:42 – What does Anthony think about the commodity risk 29:04 – Describing Standard American Mining, a company they incubated 29:58 – Exploring the shift from a CPU world to a GPU world 31:49 – Getting involved in places where we haven’t caught up with the rest of the world 33:05 – Anthony’s interest in Barstool Sports             33:11 – Dave Portnoy and Barstool Sports’ Secret Billion Dollar Plan             37:09 – Win Bigly: Persuasion in a World Where Facts Don't Matter 39:02 – What lessons from Full Tilt world would Anthony share with others in the more traditional business world 40:35 – Kindest thing anyone has done for Anthony 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
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Jan 23, 2018 • 1h 9min

Dr. Ben Hunt - The Three-Body Portfolio - [Invest Like the Best, EP.73]

My guest this week is Dr. Ben Hunt, the chief investment strategist at Salient and the author of the extremely popular epsilon theory. I’ve always enjoyed Ben’s writing style, particularly his use of farm and animal based analogies to describe market phenomenon. In this conversation, we discuss his recent post the three body problem, why growth has been beating value, and why a strategy that he calls profound agnosticism—a take on risk parity—may be the most appropriate investing strategy in what he views as a very uncertain world. We also discuss some of his favorite lessons from the farm.  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   Links Referenced The Three-Body Problem   Show Notes 1:54 - (First Question) – Applying the three-body problem to investing  7:24 – Fundamental view of investing, Profound Agnosticism  8:24 – Why has value done so poorly relative to growth in this framework  11:01 -  Ben’s thoughts on why value has been underperforming for so long  13:52 – Investors should be able to adapt  17:49 – Thoughts on the risk parity approach  23:23 – Ben’s strategy for working with several teams  26:48 – What’s the best way to gain an edge, top down factors vs company/bond individual analysis  28:29 – How do you measure risk amid the large amount of uncertainty that exists in markets  32:40 – How does Ben personally think about investing  34:41 – Ben’s farm and the investing lessons learned by some of the animals  39:55 – How bees can plan out their entire work structure by the angle of the sun  42:58 – Defining basis risk  44:59 – Personal risk vs portfolio risk  49:30 – The concept of fingernail clean and our perception of what eggs are  53:57 – How ETFs are like mass produced eggs  54:56 – Exploring the idea of quality vs scaling  58:39 – What is the current challenge/puzzle that Ben is focused on right now  1:01:59 – What is Ben looking for when looking into game theory and applying it to the words that are published and spoken about investing  1:03:57 – Most memorable day on Ben’s farm  1:05:04 – 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
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Jan 16, 2018 • 1h 13min

Preston Byrne - Crypto-pocalypse - [Invest Like the Best, EP.72]

My guest this week is Preston Byrne. Preston is vocal critic of crazy prices and projects in the world cryptocurrencies. His background is in the legal world and also as a founder and former COO of Monax, which made the first open-source permissioned blockchain client. As Preston says, he is a “blockchain without bitcoin” guy, who believes that this crypto mania will end in some sort of apocalypse for token holders and ICO issuers . We tackle several issues, from his broad skepticism of crypto assets, to the potential regulatory reaction from major governments, to types of coins like stable coins, which Preston views as analogous to perpetual motion machines.  Please enjoy our conversation and for any crypto investors out there, let me know if this conversation affects your opinion of the investing prospects for cryptocurrencies.  Hash Power is presented by Fidelity Investments   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   Links Referenced Bitcoin white paper The Bear Case for Crypto Hash Power series Zero Hedge Preston tweet on Reverse network effect   Show Notes 2:12 - (First Question) –Ponzi scheme vs pyramid scheme vs Nakimoto scheme  5:29 – Why there are regulatory challenges to cryptocurrency             5:33 – The Bear Case for Crypto  9:59 – Who are the most influential people supporting this and how are they swaying the regulatory minefield on this issue             10:28 – Hash Power series  13:23 – Looking into the idea of a digital asset and the difference between blockchain and the token itself  16:09 – What about the idea that cryptocurrency’s only feature is that it’s censorship resistant  18:39 – Why cryptocurrencies become less usable the more successful they are             18:59 – Zero Hedge  21:04 – Why can’t we rely on offchain solutions to solve the scaling issue  22:29 – The idea of bubbles and what happens next in this one            25:41 – What are the incentives to build technology to support cryptocurrencies  29:23 – Explaining Ripple  31:21 – What would precipitate a massive reversal in the inflated valuations of cryptocurrencies  34:52 – Understanding reverse network effects             34:36 – Preston tweet on Reverse network effect 37:45 – The principles behind Stablecoin 42:20 – What has been the greatest lesson that Preston has learned about blockchain he wish he knew when he first got started 44:05 – How embedded will blockchain be by 2024/2025 45:12 – ICO’s, why Preston is not a fan and if there are any positives to them 50:20 – What are the conditions under which these things will be viewed legally. 54:00 – Preston’s history owning cryptocurrencies 55:35 – What has Preston most excited in the space 59:02 – Utility settlement coin 1:00:36 – Why the fascination with marmots 1:02:10 – What to reference before getting started with cryptocurrencies 1:04:03 – Understanding supply chains in block chain 1:07:14 – Some smart people on block chain to follow 1:08:24 – Kindest thing anyone has done for Preston 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  
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Jan 9, 2018 • 1h 18min

Ali Hamed – Creative Investing - [Invest Like the Best, EP.71]

I have a special request this week: share this episode with every curious person in your life.  The conversation, with a 26-year old investor named Ali Hamed, serves as an example of what’s possible when you think creatively.  Ali views the world with a fresh set of eyes, and has already become an expert at identifying new investment opportunities where others have not. As the second prodigy 26 year old in as many weeks on the podcast, these young guns are making me feel like an ancient 32 year old.  We talk a lot about “alpha” in our world, earning returns better than the market. But the key word in that last sentence isn’t alpha, it’s earning. Hopefully you, like me, will use this conversation as a reminder of what it takes to earn differentiated returns. It’s not just the hard work, but also the mindset. We explore many examples of how to create new investment opportunities, from rolling up Instagram accounts, to financing perishable fruit like watermelons, to heavy machinery software.  Please enjoy this special conversation with Ali Hamed. Follow him and his partners. And then go figure out how to earn success yourself in whatever it is you do by helping other people solve problems with empathy.  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   Books Referenced The Big Short: Inside the Doomsday Machine   Links Referenced Sheel Tyle Podcast Seed Investing is a B2C Business, While Growth Stage investing is a B2B Business Ira Judelson podcast Free Content and Digital Media Are Increasing Socio-Economic Disparity    Show Notes 2:24 - (First Question) Ali’s investment philosophy  3:33 – History of Coventure and its unique structure  6:30 – The story of how Coventure was seeded  12:29 – What makes cost of capital such an interesting topic for Ali  14:13 – Exploring fee structures and the expectations for return in the current environment  17:02 – The current state of the VC world  21:42 – Ali’s investment process on the VC side  25:32 – What other requirements are there for Ali to make a VC investment  28:00 – Understanding the difference between judgement and empathy in founders             28:20 – The Big Short: Inside the Doomsday Machine 29:47 – Dealing with LP’s             32:47 – Sheel Tyle Podcast 33:39 – At one point did Ali feel the most personally at risk in his career 37:55 – Why did they get involved in cryptocurrency  43:30 – What excites Ali most about crypto 46:09 – Lending as an alternative way to invest in businesses 48:09 – An overview of their lending business 50:21 – How does deal flow and sourcing work in these arrangements 52:54 – How much encroachment will Ali face from competitors 54:28 – Exploring the idea of valuing and buying digital accounts 59:36 – How Ali thinks about marketing for his own firm and the ones he invests in 1:00:06 – Seed Investing is a B2C Business, While Growth Stage investing is a B2B Business 1:03:59 – Longer term aspirations for Ali and industries that he would avoid             1:04:25 – Ira Judelson podcast 1:08:05 – Ali’s view on the potential negative impact of free content             1:08:19 - Free Content and Digital Media Are Increasing Socio-Economic Disparity 1:12:48 – Kindest thing anyone has done for Ali   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
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Jan 2, 2018 • 55min

Sheel Tyle - The Future of Venture Capital - [Invest Like the Best, EP.70]

My guest this week is Sheel Tyle, who at just 26 years old has already had a successful career in venture capital. His most recent stint was as the co-head of the seed investing business at NEA, the largest venture capital firm in the world, where Sheel was also a partner. Now, Sheel has set off on his own, setting up his own firm called Amplo and having recently raised a $100M venture fund where he is the sole general partner. He aims to invest with young, mission driven entrepreneurs with a global focus. As you can tell from this resume, which also includes a degree from Stanford and a law degree from Harvard, this is one ambitious guy.  There are several aspects of this conversation that will really stick with me, specifically his points on networking and the smartest decision that he’s seen entrepreneurs make. I also loved our discussion of some of the same trends we explored last week with Chris Dixon—topics like drones, automated cars, and blockchain, where Sheel often has a different take than the consensus.  Please enjoy my conversation on Africa, entrepreneurship, venture capital trends, technology, and more with Sheel Tyle.   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   Books Referenced Originals: How Non-Conformists Move the World   Links Referenced Andela OneConcern Andy Rachleff Podcast Episode Mark43 TechCrunch VentureBeat Bill Draper (author)   Show Notes 2:20 - (First Question) Sheel’s upbringing and how it shaped his interest in Africa 4:43 – The outlook for Africa 6:10 – Primary differences in valuations and momentum in Africa vs opportunities in other places which Sheel conveys through the story of Andela 10:45 – The perspective returns of venture capital investments 15:16 – Does the hyperfroth in ICO’s serve as a threat to traditional venture capital 17:53 – Where Sheel falls on the importance of networking in terms of his venture capital interests 20:38 – The stronger impact of a smaller, more tight-knit network 22:46 – Sheel’s feelings on driverless cars and the timeline for this sector 27:17 – What are the positive side effects of driverless cars taking over 29:01 – What is the best way to invest in driverless cars from a venture capital standpoint 31:30 – Sheel’s overrated/underrated take on different technology spaces             31:30 – VR/AR             32:21 – Blockchain             32:54 – Machine learning/AI 33:41 – Drones 34:53 – Other categories that we should be thinking about             36:54 – OneConcern 38:21 – Should entrepreneurs be raising more money over future liquidity concerns of the venture capital markets 39:40 – What are the places that Sheel can help a founder in the early stage formation of the company             40:02 – Andy Rachleff Podcast Episode 42:53 – What does the breakdown of domestic vs international investments potentially look like in fund 1 for Sheel 44:53 – Sheel’s most memorable travel experience 47:34 – what is the best decision Sheel saw a founder make             48:10 – Mark43 50:31 – Resources for people interested in venture capital             51:06 – TechCrunch             51:07 – VentureBeat             51:17 – Bill Draper (author)             51:25 – Originals: How Non-Conformists Move the World     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
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Dec 26, 2017 • 1h

Chris Dixon – The Future of Tech - [Invest Like the Best, EP.69]

My guest this week is Chris Dixon, who has written some of my favorite essays on technology and venture investing. Chris is a prolific investor and thinker, having been an entrepreneur, angel investor, and now partner at the well-known venture capital firm Andreessen Horowitz. Our conversation focuses on major trends in technology, including cryptocurrencies and the future of autonomous vehicles and drones. Chris has a rule of thumb for technology trends: find out what smart people are working on during the weekend, and you’ll know what other will be doing years in the future. After surveying his old essays, it’s clear you use Chris’s writings as a similar litmus test.Hash Power is presented by Fidelity Investments Please enjoy this great conversation with Chris Dixon on the future of tech.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 Books Referenced Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages Who Controls the Internet?: Illusions of a Borderless World Links ReferencedDouglas HofstadterDaniel Dennett How Aristotle Created the Computer New Yorker Cover on automationThe World of Numbers websiteJerry Neumann podcast episodeDavid Tisch podcast ERC-20 Token Standard Eleven Reasons To Be Excited About The Future of Technology Show Notes2:04 (First Question) – Why did Chris choose to study philosophy2:23 – Douglas Hofstadter2:24 – Daniel Dennett3:20 – How Aristotle Created the Computer 3:35 – Where has his thinking and viewpoints changed the most having been in the real world 4:42 – What is the real driving force behind all of the technology that we are creating and will automation kill all of the jobs6:16 – New Yorker Cover on automation6:57 – The World of Numbers website8:36 – A look at his history in networks and network design11:03 – Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages11:07 – Jerry Neumann podcast episode12:32 – Who Controls the Internet?: Illusions of a Borderless World13:06 – What are the market and technological forces that make it difficult to regulate software hardware companies14:39 – The best features of proprietary centralized networks and open networks16:40 – What things are better centralized vs decentralized22:30 – David Tisch podcast23:03 – When it comes to cryptocurrencies, what are the concerns that the protocols themselves hold value and could this lead to centralization of the system problems24:02 – Block size debate (topic)26:40 – ERC-20 Token Standard27:23 – Is the blockchain the answer to the stagnation of the big tech players 34:39 - How does Chris think about the dichotomy of investing in people vs technologies34:59 – Eleven Reasons To Be Excited About The Future of Technology 37:45 – What organizational structures of companies are most compelling 41:50 – Any major trends in technology a cause for concern for Chris 44:09 – What major trends is Chris passionately pursuing 51:15 – If everyone agrees on a future trend of technology, can you still make money investing in them 52:20 – How do you encourage younger people to approach the world and a career differently in this ever-changing world 57:39 – Kindest thing anyone has done for Chris Learn MoreFor 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/bookclubFollow Patrick on twitter at @patrick_oshag
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Dec 19, 2017 • 1h 28min

Sorin Capital – Retail Contrarians - [Invest Like the Best, EP.68]

Jim Higgins, founder of Sorin Capital, and Tom Digan, co-lead and former classmate of Patrick, delve into the intricacies of commercial real estate investment. They explore the $7 trillion commercial real estate market, highlighting the resilience of grocery-anchored shopping centers amidst e-commerce challenges. Their contrarian strategies uncover hidden opportunities, emphasizing the importance of liquidity and thorough asset evaluation, especially in retail. They also reflect on the evolution of the hedge fund industry and the advantages of specializing in commercial real estate.
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Dec 12, 2017 • 59min

Franklin Foer – World Without Mind - [Invest Like the Best, EP.67]

My guest this week is Franklin Foer, the author the recently published book “World Without Mind.” The topic of our conversation is one that I’ve been thinking through often this past year: the impact that large technology companies have on our minds and behavior. This conversation is only indirectly related to markets, but given that the companies we discuss are now several of the largest by market cap in the global stock market, what happens to them likely impacts all of our portfolios whether we own them or not. Given that these companies compete for our attention and dollars, they also affect our businesses. As an example, My friend Brent Beshore and his team at Adventures wrote a long and incredibly thoughtful piece on how they think about Amazon as a force in the market, and how they plan on navigating around such a fierce competitor. Franklin’s book, especially the early history, is very thought-provoking, so it was no surprise that our conversation was too. Please enjoy our talk on the tech giants. 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   Links Referenced Free PDF of The Whole Earth Catalog Amazon Must Be Stopped (New Republic) Hannah Arendt Philosophy Time Well Spent   Books Referenced World Without Mind: The Existential Threat of Big Tech The Whole Earth Catalog The Lessons of History   Show Notes 1:40 - (First Question) – As part of Jonathan’s new book, World Without Mind: The Existential Threat of Big Tech, exploring the idea of the whole earth catalogue.             4:09 – The Whole Earth Catalog             4:36 – Free PDF of The Whole Earth Catalog 4:49 – What happened next for Brand and how he laid the early groundwork for today’s modern Silicon Valley 7:43 – Franklin’s personal journey into writing this book             10:00 – Amazon Must Be Stopped (New Republic) 11:48 – Thoughts on the advancement of technology in our world 15:52 -  Filling the gap into Brand’s influence on Silicon Valley from the early 80’s to today 18:57 – How does the current state of the free internet without gatekeepers hold up for the next generation 20:53 – Is there a chance that technology’s unlimited mining of our attention is not the horrible thing we often make it out to be 24:47 – What are the ways we can have a free internet and other technologies, but not let them get perverted 28:09 – How will people respond to our tech monopolies 31:54 – The Lessons of History and the rise and fall of centrist powers 33:02 -  A look at Franklin’s work and how its impacted by the reliant on a few large tech companies 35:28 – The dangers that tech giants like Facebook, Amazon, etc, have created for us 40:45 – Is there a technology, company, or trend that Franklin is really excited for 42:19 – Will there be movements that emphasis detachment from technology 44:05 – Why most innovations have happened to people thinking in a very separated or contemplative mode 45:58 – What’s the most exciting thing that Franklin is thinking about now 49:30 – What was the most memorable content in researching this book that Franklin would suggest other check out             49:59 – Hannah Arendt Philosophy 52:37 – Are there specific things that Franklin does to be more contemplative             53:26 – Time Well Spent 54:47 – Kindest thing anyone has done for Franklin   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
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Dec 5, 2017 • 1h 9min

Adam Ludwin - A Sober View on Crypto - [Invest Like the Best, EP.66]

My guest this week is Adam Ludwin, the founder and CEO of Chain, a blockchain technology company targeted at large enterprises. Before shifting his career to focus solely on crypto, Adam was a venture capitalist focused on FinTech, which is how he came across the Bitcoin whitepaper earlier than most. I called this episode “a Sober View on Crypto” because Adam’s take is so balanced. He is certainly long crypto, both in his portfolio and career, but he is very skeptical of much of what is happening in the ecosystem today. For example, he offers the best reason I’ve heard for not launching an ICO or investing in them.  If you haven’t read Adam’s widely shared open letter to Jamie Dimon, it has become a must-read piece for crypto-enthusiasts. Read it as soon as you can. I edited out an earlier chunk of our conversation as it was largely introductory. If you need a broader introduction to cryptocurrencies, I suggest starting with episode one of Hash Power and working your way forward. One key insight from Adam in our offline discussion what how cryptocurrencies function very much like equities or bonds. Just as equity financing enables the activity of joint stock corporations, cryptocurrencies enable activity in decentralized applications. We pick up our discussion with Adam discussing whether anyone really uses these decentralized apps today. Hash Power is presented by Fidelity Investments   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 2:35 - (First Question) – Will anyone use cryptocurrency in the real world at a large scale 3:43 – The idea of censorship resistance 12:29 – Will society be accepting of this technology 14:39 – Why decentralized apps can’t be acquired 18:24 – The idea of exponential vs linear improvements on a trend and if there are limits to the growth of decentralized technologies 23:26 – The struggle with early adaption of blockchain 25:41 – Best application for bitcoin, storing value 29:52 – Adam’s introduction to cryptoassets and how his thinking has evolved in the space 36:44 – In this hyper frothy market, is there a situation that makes an ICO exciting to Adam 43:51 – Even though it appears to be easy money, Adam explains why you shouldn’t just create an ICO 50:59 – A look at what Chain is doing and what Adam is excited about 53:23 – How does what Adam is working on help to improve the ledger of his clients 1:02:00 – Why you can easily be an early investor in crypto currency 1:04:27 – Kindest thing anyone has done for Adam   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
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Nov 28, 2017 • 59min

Joanne Wilson - Angel Investing and Trend Spotting - [Invest Like the Best, EP.65]

My guest today is Joanne Wilson, a New York City based angel investor, writer, podcaster, trend spotter, and self-described “woman around town.” Joanne has had a multifaceted and winding career, and began angel investing a decade ago when she put money into NYC-based media company Curbed media which we discuss in detail. Since then, she’s invested in more than 90 companies and been pitched by countless more. She is an instantly likeable person, you can literally tell in 10 seconds you are going to have a great conversation, so it’s no surprise that part of what makes her unique among angels is a very close relationship with many of the founders she backs. We cover a lot of ground. We talk about the personality traits of entrepreneurs, Joanne’s evolving investment style, her focus on female founders, fashion, business models, restaurants and a lot more. Please my conversation with the Gotham Gal, Joanne Wilson.   For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. 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 2:12 - (First Question) – How does Joanne orient herself towards what’s new, in the context of food in New York city 4:10 – Can that mindset of forward thinking be cultivated 5:18 – Latest thing that got Joanne excited before everyone else 6:57 – Why the new frontier is going niche and local 10:23 – Joanne’s first investment 11:48 – Why do VC’s typically stay away from media 12:55 – How Joanne got into her first investment as a customer 14:11 – What is the skillset of making money that Joanne as 14:45 – Can you sense if a founder has that innate ability to just make money 17:04 – Are there common traits in founders 18:07 – Joanne’s progression into angel investing after her first investment 19:58 – Red flags when looking at investments 20:40 – Impression on growth without goals 23:30 – Trends among Joanne’s investments 25:56 – How much knowledge is transferrable between different industries that Joanne invests in 27:06 – The dichotomy and unique challenges between raising capital with female founders vs male founders 29:07 – How does Joanne balance her time and stay engaged with all of her investments 30:50 – Time when Joanne has helped a founder side step a pothole 31:35 – Most memorable first impression Joanne experienced 35:05 – How often does someone not have the right idea but is still worth investing in 37:19 – Why Joanne won’t start a fund 38:22 – Data on female founders returns and time 40:38 – Criteria for identifying emerging trends, especially in the more creative/artistic fields  43:29 – The changing costs of launching a brand, in the contest of fashion 47:11 – What has Joanne most excited right now       48:11 – Interesting facts about the fashion business  52:01 – Kindest thing anyone has done for Joanne   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

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