
73 segments available
Jason Calacanis is an angel investor, entrepreneur, and co-host of All-In Podcast and This Week in Startups. Please support this podcast by checking out our sponsors: - Brave: https://brave.com/lex - Linode: https://linode.com/lex to get $100 free credit - Four Sigmatic: https://foursigmatic.com/lex and use code LexPod to get up to 60% off - Rev: https://rev.ai/lex to get 7-day free trial EPISODE LINKS: Jason's Twitter: https://twitter.com/Jason Jason's Website: https://calacanis.com/ Jason's YouTube: https://www.youtube.com/user/ThisWeekIn Jason's Link Tree: https://linktr.ee/calacanis All-In Podcast: https://linktr.ee/allinpodcast This Week in Startups Podcast: https://thisweekinstartups.com/about/ PODCAST INFO: Podcast website: https://lexfridman.com/podcast Apple Podcasts: https://apple.co/2lwqZIr Spotify: https://spoti.fi/2nEwCF8 RSS: https://lexfridman.com/feed/podcast/ Full episodes playlist: https://www.youtube.com/playlist?list=PLrAXtmErZgOdP_8GztsuKi9nrraNbKKp4 Clips playlist: https://www.youtube.com/playlist?list=PLrAXtmErZgOeciFP3CBCIEElOJeitOr41 OUTLINE: 0:00 - Introduction 1:51 - WallStreetBets and Robinhood 12:58 - How does the WallStreetBets saga end? 16:09 - Capitalism 21:30 - Ideas vs Execution 22:37 - Learning to learn 28:05 - Risk-aversion 34:06 - Robinhood 42:33 - Parler and AWS 44:58 - Social networks 51:32 - Leadership 56:21 - Work-life balance 1:04:43 - Great leaders lead by example 1:12:29 - Advice for startup founders 1:16:56 - Clubhouse 1:17:42 - When will we fully re-open the economy 1:28:19 - Augmented reality 1:31:47 - When should a startup raise money? 1:38:43 - David Goggins 1:40:40 - Disagreement with Chamath Palihapitiya 1:53:52 - Story about Elon Musk's darkest moments 2:02:07 - Friendship SOCIAL: - Twitter: https://twitter.com/lexfridman - LinkedIn: https://www.linkedin.com/in/lexfridman - Facebook: https://www.facebook.com/LexFridmanPage - Instagram: https://www.instagram.com/lexfridman - Medium: https://medium.com/@lexfridman - Reddit: https://reddit.com/r/lexfridman - Support on Patreon: https://www.patreon.com/lexfridman
Jason Calacanis discusses the historic impact of the WallStreetBets saga and its implications for capitalism. He reflects on how this movement represents a philosophical shift in how individuals can challenge traditional power structures in finance, emphasizing the human elements of greed, power, and freedom that underpin these events.
"the following is a conversation with jason calacanis who's an entrepreneur investor author of angel how to invest in technology startups and as many people may know he's a fun brilliant long time podc..."
Calacanis shares his experience as an angel investor in Robinhood, detailing the initial pitch he received from founder Vlad Tenev. He highlights the boldness of the idea to attract millennials to stock trading, despite the skepticism surrounding retail investors after the dot-com crash and the 2008 financial crisis.
"conversation with jason kilikanis i have a million things to talk to you about but we do happen to be living through what i would think of as a historic event in in terms of its impact in terms of lik..."
In this segment, Calacanis explains the importance of believing in outlandish ideas as an angel investor. He reflects on how unconventional concepts, like Robinhood's free trading model, can lead to significant returns, drawing parallels with other successful startups like Uber.
"go to antonio's nut house and um we'll meet elon for a drink uh and so elon met us for a drink there and it's it's the divest of dive bars like you'll take a beer love the image of all of this you han..."
Calacanis discusses the transformative effect of Robinhood on a new generation of investors. He emphasizes how the platform has democratized trading, enabling individuals to engage in sophisticated financial strategies and challenge established financial institutions.
"he said well we're going to get these millennials to trade i said the same ones who live in their mom's basements and take uber and lyft and are on their parents have no money got screwed and you know..."
Calacanis reflects on the stress tests that the financial system underwent during the WallStreetBets phenomenon. He discusses the lack of transparency in short selling and how the events revealed vulnerabilities in the financial markets, prompting a reevaluation of existing systems.
"financially sophisticated that they know how to do puts and calls and shorts and research at a level that dominated the hedge fund industry so let's pause for a second these traders sitting there on a..."
In this segment, Calacanis addresses the conspiratorial mindset that can arise in the absence of transparency in financial markets. He discusses how Robinhood's mission to democratize trading can sometimes lead to misunderstandings and conspiracy theories among investors.
"markets and it turns out there were more people shorting the stock than stocks where the shares were available i don't know how that's possible and then i'm trying to uncover where can i see a list of..."
Calacanis explores the chaotic nature of the WallStreetBets movement and its implications for the financial landscape. He discusses the duality of the movement, where some participants seek to challenge the elite while others may simply want to create chaos.
"and robin hood in that same way probably enabled or was one of the major enablers of wall street best of giving power uh like empowering young kids to learn about how this whole messy financial system..."
Calacanis speculates on the future trajectory of the WallStreetBets community. He considers whether they will continue to challenge power structures or if their actions will lead to unintended consequences that could disrupt the economy.
"to do this options trading and puts and calls and all this sophistication stuff unless you actually do it it's just too hard to learn except in practice just like poker if you want to learn how to pla..."
In this concluding segment, Calacanis reflects on the educational aspect of the WallStreetBets phenomenon. He highlights how the movement has empowered individuals to become financially literate and engaged in the complexities of the financial system, fostering a new generation of informed investors.
"for who yeah who's crying is everybody crying who's crying when so i think there were some of the hedge funds that were crying initially that maybe some of the wall street bets people who bought last ..."
In this segment, Calacanis argues that capitalism is fundamentally a force for good, enabling innovation and competition that benefits society. He contrasts this with the dangers of socialism and communism, advocating for a vibrant capitalist environment that fosters entrepreneurship and technological advancement.
"most about we're at society is the sort of socialism communism you know entrepreneurship is bad technology is bad and polarization of wealth and you know people getting rich is a bad thing when i grew..."
Calacanis discusses China's blend of communism and capitalism, describing it as a unique and potentially dangerous system. He warns that if China succeeds in its approach, it could pose an existential threat to global capitalism and innovation, highlighting the need for vigilance in maintaining a competitive capitalist landscape.
"less competition for accreditation degrees like things tend to get a little weird don't they yeah and people tend to be protected and that's not good you need you need competition um does it mean that..."
Calacanis emphasizes the importance of the entrepreneurial spirit in driving societal progress. He argues that society should celebrate and support young entrepreneurs, encouraging them to take risks and innovate. He believes that fostering this mindset is crucial for overcoming societal challenges.
"existential threat for humanity yeah the chinese are no joke i mean they are seriously focused and they are picking the winners it's a very weird system because it is in fact i don't know what you cal..."
In this segment, Calacanis highlights the unprecedented access to knowledge available today through online platforms. He challenges the notion that poor individuals lack opportunities, arguing that the resources for learning are widely accessible and that belief in one's potential is key to success.
"i do get bothered by people you know treating the word billionaires if it's a bad word yeah but in general like all the hard things all the difficult things we're going through in this country it seem..."
Calacanis stresses the necessity of skill development for aspiring entrepreneurs. He encourages individuals to invest time in learning new skills instead of consuming entertainment, arguing that this investment can lead to significant personal and professional growth.
"group of people that i think are highly vocal but a small group of people which are generally people of incredible privilege rich parents white city dwellers liberals they kind of look and say poor pe..."
Calacanis discusses the concept of deliberate practice, emphasizing that quality of practice is more important than quantity. He shares personal anecdotes about learning new skills and the importance of analyzing mistakes to improve performance.
"have internet and i'm like really find me any downtrodden person without a smartphone with a high-speed connection that capitalism provided for 12 a month or 15 a month like it's very hard to find tha..."
In this segment, Calacanis talks about the essential skill of learning how to learn. He shares insights on how to effectively acquire new skills and the importance of being proactive in one's education, drawing parallels to competitive environments and the benefits of capitalism.
"yourself can build the thing and every no matter what your circumstances are and you could talk about like structural racism and all those kinds of things that very fast but from the individual perspe..."
Calacanis highlights the role of competition in driving innovation and improvement. He uses examples from sports and business to illustrate how competition can lead to better products and services, ultimately benefiting society as a whole.
"was a basketball court and uh i said let's go let's go shoot some hoops i never shoot shot before and i was like okay come on i'll teach you and tim is fabulously uncoordinated people don't know this ..."
Calacanis reflects on the lessons learned from the pandemic, emphasizing the resilience of the human spirit and the potential for innovation in crisis. He discusses the rapid development of mRNA vaccines as a testament to what can be achieved when people are motivated and regulations are streamlined.
"a ux person a developer whatever it is and learn how to add skills that's what i did my whole life i was a kid from brooklyn went to school at night but i was very quick to get to maybe 50 of the know..."
Jason Calacanis discusses the unexpected positive outcomes of the COVID-19 pandemic, particularly in the realm of vaccine development. He highlights how the urgency of the crisis led to rapid advancements in mRNA technology and the potential for future pandemic preparedness. Calacanis argues that the pandemic has forced society to rethink regulations and embrace innovative solutions to combat global health crises.
"10 years electric cars ha ha that company will go out of business and now every single company is like we're going fully electric by 2035 and he kicked their asses so brutally that they had no choice ..."
In this segment, Calacanis explores the concept of challenge trials, where healthy individuals are intentionally exposed to viruses to test vaccine efficacy. He questions societal risk aversion and compares it to other high-risk professions. Calacanis advocates for a rational discussion about the ethics and potential benefits of such trials in the context of a global pandemic, emphasizing the need for innovative thinking in crisis management.
"we could have said these thousand people young people who we know are in all likelihood not going to have a bad outcome but there's a possibility this is a possibility but it's very low and it's certa..."
Calacanis reflects on the failures and successes of capitalism during the COVID-19 pandemic, particularly regarding testing and vaccine distribution. He critiques regulatory barriers that hindered rapid testing solutions and discusses how a more agile capitalist approach could have mitigated the crisis. This segment emphasizes the importance of adapting business practices to meet urgent public health needs.
"people are going to lose their lives right so you know that's an example of capitalism and competition working really well there there's one of the to me sad thing to see about coronavirus is that for..."
In this segment, Calacanis analyzes Robinhood's communication failures during a liquidity crisis amid the WallStreetBets phenomenon. He discusses the importance of transparency and proactive communication for startups facing crises. Calacanis highlights how poor communication can lead to panic and loss of trust, using Robinhood's experience as a case study for other startups.
"we were all i give them that until june i wonder how history will remember this whole period i'd love to ask you because you were an early investor in robin hood and you're sort of you're in a very ni..."
Calacanis delves into the challenges faced by CEOs during crises, particularly focusing on Vlad Tenev of Robinhood. He compares Tenev's communication style to that of other tech leaders like Elon Musk and Mark Zuckerberg, discussing how public perception can be influenced by a leader's ability to convey trust and transparency. This segment underscores the critical role of effective leadership in navigating turbulent times.
"on the nature of communication uh vlad the ceo yeah the guy you met at the bar yeah i think at the center of the communication right yep so elon is an example of a guy who also is at the center of the..."
In this segment, Calacanis reflects on the accelerated pace of startup growth and market relevance in the digital age. He discusses how technological advancements and social media have transformed the landscape for entrepreneurs, allowing for rapid scaling and user acquisition. Calacanis emphasizes the importance of understanding market dynamics and adapting to the fast-changing environment of modern business.
"operating it yeah and if you are going to operate uh we basically vilify and demonize i think that that is part of it like when the person at i remember airbnb we always thought what if somebody trash..."
Calacanis discusses the implications of social media censorship, particularly in the context of the Capitol riots and the banning of Parler from AWS. He raises concerns about the power dynamics between social networks and their users, emphasizing the need for a balanced approach to content moderation. This segment highlights the challenges faced by entrepreneurs in a landscape where technology and public opinion intersect.
"speaking of clubhouse i mean yeah i just wanna we're saying so many interesting things but there there was a magical moment with vlad and elon on clubhouse yes is there do you have thoughts about that..."
Calacanis expresses his concerns about the removal of Parler from AWS and the broader implications for free speech and entrepreneurship. He argues that the power of large tech companies to censor voices poses a significant risk to the entrepreneurial landscape, advocating for decentralized and censorship-resistant platforms as a potential solution.
"that little maybe i'm being overdramatic but no you're not i think you're paranoid for a reason you're paranoid for a very good reason which is as big as these companies can become they are beholden t..."
In this segment, Calacanis explores the potential for new social media platforms to emerge that could rival giants like Facebook and Twitter. He reflects on the history of social networks and the possibility of decentralized alternatives, emphasizing the need for innovation in the social media space to foster competition and diversity.
"and that could be tweets it could be videos and so this idea that you know youtube will be able to tell people to kick people off because they're skeptics of i don't know the pandemic or the vaccine o..."
Calacanis shares insights on what makes a great leader in the tech industry, contrasting figures like Mark Zuckerberg and Elon Musk. He discusses the importance of vision, the challenges of leadership, and the sacrifices required to drive innovation and change within organizations.
"now it'd be worth 500 million do you think 500 billion yeah do you think uh facebook might buy clubhouse has been uh oh they'll probably copy it i mean zuckerberg has no moral compass or ethics or any..."
This segment delves into the intense environment of startups and the sacrifices that come with pursuing ambitious goals. Calacanis argues against the notion of work-life balance in high-stakes environments, emphasizing that true commitment to changing the world requires a level of dedication and resilience that many may not be prepared for.
"processes is the playbook of silicon valley for the last decade or two so whatever the friction poetry what you're saying right outside you're speaking so fast that i almost forget that you're you're ..."
Calacanis critiques the perceived softness of modern generations in the face of challenges, contrasting it with historical struggles. He argues that the lack of significant sacrifice in recent times has led to a generation that may not fully understand the demands of high-stakes environments, particularly in the tech industry.
"and there was this famous case when they first came out with it um somebody created a nambla fake group national man love boy association or whatever like pedophilia association and they added zuckerb..."
Jason Calacanis discusses the intense commitment required in startup culture, emphasizing that if you're not serious about changing the world, you shouldn't work for major innovators like Bezos or Musk. He critiques the notion of work-life balance in startups, arguing that those seeking it should avoid ambitious companies. Instead, he highlights the necessity of passion and sacrifice in the pursuit of revolutionary ideas.
"blackhawk like this is serious shit like don't do it if you're not serious yeah and if you're not serious about changing the world why would you go work for bezos why would you go work for elon musk d..."
Calacanis reflects on the perceived softness of recent generations in America, attributing it to a lack of significant struggles compared to past generations. He contrasts this with the rapid improvement of living conditions in China, where many are thrilled to join the middle class despite harsh realities. This segment explores the cultural differences in resilience and ambition between Americans and those in developing nations.
"do not go to a startup or any kind of ambitious company there is a series of places you can work in the world yes where you do not need to do anything more than what's put in front of you and you just..."
In this segment, Calacanis warns about the critical importance of winning in capitalism, asserting that failure to do so could threaten the future of humanity. He discusses the current state of democracy globally and the need for America to maintain its economic edge against authoritarian regimes like China. The conversation highlights the role of entrepreneurs and innovators in this battle for the future.
"so we're soft as americans we're soft and then you look at people in china and we're like oh my god these poor chinese people are living in these tiny cramped apartments like they were living in like ..."
Calacanis elaborates on the qualities of effective leaders, emphasizing the importance of setting high standards and leading by example. He draws comparisons between leaders like Elon Musk and Jeff Bezos, discussing their relentless work ethic and the impact it has on their teams. This segment underscores the necessity of resilience and commitment in leadership roles within ambitious companies.
"i'm the richest guy on the planet uh depending on the week and uh i would like to do some other challenges but i don't want to grind it out at amazon for another 25 years i want to do other things and..."
This segment delves into the harsh realities of entrepreneurship, with Calacanis describing the sacrifices required to succeed. He discusses the mental and emotional toll it can take on founders, highlighting the importance of passion over profit. The conversation touches on the challenges faced by entrepreneurs and the need for a strong sense of purpose to navigate the difficulties of building a startup.
"that's the battlefield china wins authoritarians win and at any time xi jinping can pull jack ma into a room and say it's time for you to be re-educated or they can put three or four million people uy..."
Calacanis emphasizes the significance of having a clear purpose in entrepreneurship, arguing that founders must be driven by a mission rather than just the pursuit of money. He shares insights on how successful entrepreneurs are often motivated by a desire to create change and solve big problems. This segment encourages aspiring founders to reflect on their motivations and the importance of passion in their ventures.
"through science and technology i mean as you're describing you've hosted uh this week in startups for uh how many episodes 11 years almost 1200 now 1200. yeah so you've talked to some of the great lea..."
In this segment, Calacanis reflects on the struggles faced by successful entrepreneurs like Elon Musk and Jeff Bezos. He discusses the immense pressure and suffering that often accompany their journeys, suggesting that true innovation comes with significant personal sacrifice. This conversation highlights the darker aspects of entrepreneurship and the relentless drive required to achieve greatness.
"that journey yeah and that's why people really start to think about what is the purpose of what i'm doing and it sounds corny and i when i first heard that i was like it's kind of corny but then i rea..."
Calacanis provides an in-depth analysis of Elon Musk's work ethic and intelligence, describing him as a brilliant engineer and problem solver. He shares anecdotes from their long friendship, illustrating Musk's relentless pursuit of change and innovation. This segment offers insights into Musk's mindset and the qualities that contribute to his success as a leading entrepreneur.
"having been a witness to it um you know just as friends for for that long i have never seen an entrepreneur suffer more than him and uh you know he's been public about that like you do not want to be ..."
Calacanis discusses the concept of 'day one thinking,' a principle emphasized by Jeff Bezos. He explains the importance of approaching problems with fresh eyes and continuously questioning the status quo. This segment encourages entrepreneurs to maintain a mindset of innovation and adaptability, essential for navigating the challenges of building successful companies.
"i mean and that's another thing like that i think the great entrepreneurs can look at a problem with very fresh eyes like almost consistently and bezos described that as day one thinking right like ju..."
Calacanis discusses the concept of 'Day One Thinking' as described by Jeff Bezos, encouraging entrepreneurs to approach problems with fresh eyes. He contrasts this with the pitfalls of routine thinking and emphasizes the importance of questioning existing methods to find better solutions, illustrating this with examples from successful companies like Amazon.
"get from everybody like how do we solve this problem what people do sometimes they get in a rut they just come to work and they just go through their email they do whatever they did the day before the..."
In this segment, Calacanis explains the critical elements of successful startups: a well-built product and delighted customers. He shares insights from his experiences with investments in companies like Calm and Robinhood, stressing that exceptional execution and customer satisfaction are key to achieving success in the startup ecosystem.
"and you're like wow and it's like yeah you're paying 13 a month for the privilege of shopping at amazon yeah but you wouldn't you say it's the greatest thing in the world because anything i need you k..."
Calacanis recounts his investment journey into Calm, the meditation app, driven by insights from Sam Harris and the credibility of UCLA's mindfulness programs. He reflects on how this investment has become one of the most significant in his career, highlighting the intersection of wellness and technology in today's market.
"members of that it's the largest syndicate in the world in fact the first deal we ever did was com.com the meditation app we put 378 thousand dollars into it when it was a 5 million dollar product a 5..."
Calacanis emphasizes that while a strong team is crucial, the ultimate measure of success lies in creating a product that delights customers. He discusses how great teams can iterate on good products to achieve customer satisfaction, using examples from various successful startups to illustrate his points.
"after uber and it will in all likelihood become the biggest i mean it's between uber robin hood and calm and long story short when i'm teaching people to angel invest there's really two things that yo..."
In this segment, Calacanis explores the concept of product market fit and user engagement, citing examples like Snapchat and Clubhouse. He explains how high engagement metrics can indicate a product's success and the importance of understanding user behavior in developing addictive and effective products.
"most people say the team is the most important but there's a lot of smart people out there and let's assume that you can have you can raise money for your idea or you have money or you can just convin..."
Calacanis discusses the psychological effects of social media, particularly during the pandemic. He reflects on how constant exposure to negative news and unrealistic portrayals of life can lead to anxiety and mental health issues, emphasizing the need for a more thoughtful approach to social media consumption.
"there's an intimacy to voice oh for sure you have people's yeah tent well but like the video gets in the way actually in a weird way there's a privacy when you just use voice people are not taking sho..."
Calacanis shares his thoughts on the future of social interactions and business in a post-pandemic world. He discusses the importance of rigorous conversations and the role of technology in shaping collective intelligence, suggesting that a thoughtful approach can help mitigate the negative impacts of social media.
"been frustrated for so long that you checked out i almost checked out because it uh psychologically allows me to carry on because i thought for many months now that testing needs to be done at scale a..."
In this segment, Calacanis reflects on how technology can both enhance and hinder human connection. He critiques the current state of social media, arguing that it often promotes division and outrage, and suggests that a shift in how we engage with technology could lead to more meaningful interactions.
"have had enough of this they're just going to go yolo i but see the the crucial piece for me that i've been focusing on is the the social media aspect of how the it's not just about the reality of dea..."
Calacanis discusses the phenomenon of outrage culture on social media, explaining how algorithms prioritize controversial content for engagement. He highlights the psychological effects of this culture on users and calls for a reevaluation of how social media platforms operate to foster healthier online environments.
"with the facebook groups example where you know you take out all that friction what happened was we used to have something called arcron reverse chronological order that's how you consumed a feed so a..."
In the final segment, Calacanis advocates for creating a more positive and constructive online environment. He emphasizes the potential for technology to facilitate thoughtful discussions and connections, urging a shift away from sensationalism and negativity towards a more uplifting and supportive digital culture.
"and then of course with trump he realized it he's like okay yeah i'm just gonna make fun of a celebrity and i get more retweets okay i'm gonna make fun of rosie o'donnell for being overweight or somet..."
In this segment, Calacanis shares his vision for a new generation of social networks that prioritize personal growth and meaningful connections. He discusses the potential for AI to enhance user experience by allowing individuals to curate their own social media algorithms, fostering a more positive and enriching online environment.
"think we haven't we got the first generation of social networks i think a new generation needs to absolutely is that your plan for a business to do so well i have a longer-term plan in terms of ambiti..."
Calacanis reflects on his experiences with Clubhouse, emphasizing the value of engaging with diverse perspectives. He describes how listening to conversations outside his usual interests has enriched his understanding and learning, showcasing the potential of social audio platforms to foster community and connection.
"commenting on things that i don't already know about because i want to open my world view that could be a beautiful thing for society and actually jack was talking about potentially on twitter letting..."
Calacanis envisions a future where augmented reality enhances social interactions by displaying connections and shared experiences between individuals. He discusses the implications of such technology for deepening human relationships and the potential for creating a more interconnected society.
"that is about relationships and or you know some fashion or hip-hop or whatever it is that i'm not part of i just sit there and i listen and you learn it's like such a delightful thing i always think ..."
In this segment, Calacanis addresses the trade-offs individuals make regarding privacy in exchange for convenience and value. He discusses how people are often willing to share personal information if it enhances their experience, highlighting the evolving relationship between privacy and technology.
"which will just shoot the shit and it'll act as like a fabric uh and a little filler between the tent pole podcasts right like you and eric you've done three i think with eric yeah was your four yeah ..."
Calacanis shares his thoughts on the future of augmented reality, emphasizing its potential to create meaningful connections and enhance social interactions. He discusses the importance of balancing innovation with ethical considerations, particularly regarding privacy and user consent.
"oh you both know sam harris or you had elon on the podcast on this date or you and i were both at burning man in 2006 the most meaningful element of our connection network yeah and then because we wou..."
Calacanis provides insights into the venture capital landscape, discussing when startups should seek funding and the mindset of investors. He explains the importance of timing and the risks associated with venture capital, emphasizing the need for founders to understand the dynamics of investment.
"well you make uh just like you were saying you make it frictionless a very low friction to make a deep human connection because you you have all the basic elements there already now think about the un..."
In this segment, Calacanis elaborates on the J-curve phenomenon in startup investing, where initial failures can lead to long-term success. He discusses the challenges founders face in the early years and the importance of resilience and adaptability in navigating the startup landscape.
"have to ask you you're just like you were saying you're one of the world experts in investing in in uh instruments in startups uh yeah uh the vc and so on from the perspective of the startup i was alw..."
Calacanis emphasizes the importance of building a sustainable business model based on customer revenue rather than relying solely on venture capital. He shares examples of successful companies that have achieved growth through capital efficiency, highlighting the benefits of a customer-centric approach.
"go to zero now if you were to start the business and only build it off customer revenue and use your own money and go nice and slow and grow ten percent a year the chances of you blowing up the rocket..."
Calacanis discusses the complexities of the relationship between investors and founders, highlighting the differing motivations and expectations. He explains how understanding these dynamics can help founders navigate the challenges of raising capital and building successful startups.
"annualized returns in order to triple the money and maybe i have an outlying chance of four or five times the money which does happen sometimes when you have an outlier in your portfolio like uber or ..."
Jason Calacanis explains the J-Curve concept in startup investing, where initial performance may decline before showing growth. He discusses the importance of product-market fit and how investors assess a startup's viability over time, emphasizing that it often takes years to determine if an investment is successful.
"back and they don't have product market fit and they're out of money yeah and they say can we have more money you say no we have to go get it from somebody else because you have to prove that there's ..."
Calacanis draws parallels between the rigorous training of Navy Seals and the challenges faced by startup founders. He highlights the necessity of enduring pain and discomfort to achieve success, referencing his upcoming ultra-marathon with David Goggins as an example of pushing personal limits.
"he dies i don't know if you know what david goggins is by any chance i do i mean i don't know him personally but oh my lord so i'm i'm running 48 miles together with him in person in a month you're do..."
In a candid discussion, Calacanis reflects on his close friendships with fellow investors and entrepreneurs, including Chamath Palihapitiya. He emphasizes the importance of loyalty and support among friends in the business world, sharing insights on how disagreements can arise yet still maintain strong bonds.
"but and speaking of uh beautiful push and pull uh how about that transition yeah here we go uh you're in chemat uh on uh he's a friend of yours bessie besties yeah yeah good friend i mean he's there's..."
Calacanis discusses a recent disagreement with Chamath regarding Robinhood and the nature of their public discourse. He stresses the significance of understanding intent behind words and actions, advocating for nuanced discussions rather than jumping to conclusions based on emotions.
"turned off trading because the hedge funds told them to and that they were bowing down to the pressure of the hedge funds that's not true but in a vacuum of information you know what happens to people..."
Calacanis shares his philosophy on loyalty as an investor, explaining how he stands by his investments and founders even during tough times. He contrasts his approach with others who may abandon their teams, reinforcing the value of commitment and support in the entrepreneurial ecosystem.
"conspiracy here what it was was robin hood needed to raise billions of dollars to say solvent in all likelihood uh and they weren't allowed to talk about it so they were forced into not talking about ..."
Reflecting on a heated podcast discussion, Calacanis talks about the challenges of maintaining friendships amidst public disagreements. He recounts how he and Chamath resolved their differences and the lessons learned about communication and mutual respect in the face of conflict.
"i always ask the founder do you want me to is it okay if i go out and defend you publicly if they say yes i do it and then beautiful by the way because what else do we have in this world if not friend..."
Calacanis discusses the media landscape's shift following Trump's presidency, noting how it has allowed for a broader range of voices and stories to emerge. He reflects on the impact of this change on public discourse and the opportunities it presents for new narratives.
"everybody else who's on the pod the two davids who you know both on the spectrum a bit like a little aspergers or whatever no effects left none taken i'm not saying you know yeah there is a yeah if yo..."
In a personal anecdote, Calacanis shares an experience of being doxxed over a disagreement on social media. He highlights the risks associated with online interactions and the importance of considering the potential consequences of one's words and actions in the digital age.
"yeah he was exhausting i mean the amount of cycles he took on our processors and now this is a little bit more of a distributed like this yeah everybody gets a chance to be the number one news story e..."
In this segment, Jason reflects on the importance of empathy when dealing with conflicts, particularly in the digital age. He highlights how understanding someone's intent can de-escalate situations and prevent personal destruction, advocating for kindness over retaliation.
"right like just getting through the days hard yeah and and that little bit of empathy uh thinking about the intent of the person allows you to then sort of de-escalate this kind of conversation that s..."
Jason discusses the role of friendship and support in the challenging journey of entrepreneurship. He shares a poignant story about his friendship with Elon Musk during Tesla's darkest days, illustrating how love and loyalty can make a significant difference in high-pressure situations.
"there's music to my ears your whole rant on the the olympic nature of a startup is there a role like what role does love family friendship play in that brutal pursuit of excellence that is building a ..."
In this concluding segment, Jason emphasizes the ripple effect of kindness and support in the entrepreneurial community. He reflects on how positive interactions can inspire future generations and create a legacy of love and support, encouraging listeners to invest in relationships rather than negativity.
"rocks at there's somebody who's making the jewel vaporizer throw rocks at that scumbag no offense but like whoever's making the jewel things and you know selling pina colada flavor to 12 year olds lik..."
Calacanis reflects on his personal journey in the startup world, discussing the evolution of his thoughts and insecurities. He shares a pivotal moment with Sam Harris that reshaped his perspective on ideas and self-worth, emphasizing the importance of connection and mentorship in achieving success.
"and i was like wow sam that was like of my entire friendship with sam harris that was like the one moment where i was just like oh my god all my life i've wondered about all these thoughts in my head ..."
This segment captures Calacanis's passion for supporting early-stage startups. He describes the joy of witnessing founders achieve product-market fit and the emotional connection that comes from being part of their journey, likening it to the survival of baby turtles against the odds.
"and also either be with me into the rough times be with them with that first i mean the first early successes i mean that's a beautiful so great when they when when when a founder and that team get pr..."
Calacanis emphasizes the transformative power of gratitude in our lives. He shares a personal story about receiving a heartfelt gratitude letter, encouraging listeners to express appreciation to those who have helped them. This act of kindness can amplify joy and strengthen relationships.
"i think there's no better way to end it there it is the talk of the cruelty of life that's suffering that is life and the love amidst the suffering jason absolutely i've been a fan of yours for a long..."
In the closing moments, Calacanis delivers a powerful insight on startup failures, stating that the primary reason for failure is not running out of money, but rather the founder giving up. This poignant reminder underscores the importance of perseverance in the entrepreneurial journey.
"so just then you can look it up gratitude gratitude is like one of these incredible forces amen i'm grateful for being on the pod i'm grateful you've wasted all this time with me i love it thanks for ..."