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    #150 - Jason Calacanis Joins The Brainstorm To Talk Robinhood, Gambling and the Opportunities He's Investing In

    enFebruary 03, 2021

    Podcast Summary

    • Streamlining business operations with a single source of truthUsing HubSpot's customer platform to manage all customer interactions in one place simplifies communication and offers AI-supported features for personalized messaging. Adaptability to changing circumstances is crucial for business success.

      Having a single source of truth for your business operations can save you from the hassle of managing multiple software systems. HubSpot's customer platform offers a solution by organizing and tracking all customer interactions in one place. This not only makes it easier to manage your team's communication but also provides AI-supported features to help determine the best messaging for each customer. Jason, a guest on the podcast, shared his personal experience of moving his business operations online during the pandemic and considering a move to Austin due to the lower cost of living. He mentioned a baller move he heard about during his research, where someone stated they had no budget for a house in Austin, emphasizing the significant price difference between cities. Overall, the importance of having a streamlined business system and being adaptable to changing circumstances were key themes in the discussion.

    • Observing similarities between journalism and VCJournalism and VC share skills like asking probing questions, assessing business models, and looking to the future. Perseverance is crucial in both fields.

      The speaker, who started his career in journalism and publishing, has observed a parallel between the skills required in journalism and those required in venture capital investing. He noted that both involve asking probing questions, assessing business models, and looking to the future. The speaker also shared his experience with gambling, mentioning that he started with low stakes and gradually increased them over time. Despite some significant losses early on, he ultimately came out net even and saw it as a way to build relationships with high-profile individuals. The speaker's career journey demonstrates the transferability of skills and the importance of perseverance in the face of challenges.

    • Jason Calacanis' Preference for Startups Over GamblingAngel investor Jason Calacanis prefers investing in startups due to the social aspect and his expertise, contrasting his past experiences with gambling. He also shares his encounter with Robinhood's founders in an unusual setting and the importance of not counting your money for wealth.

      Jason Calacanis, a top 5 angel investor, shared his experiences with gambling and how he prefers investing in startups over poker due to the social aspect and his expertise in the field. He also mentioned his encounter with Robinhood's founders before their launch and the unusual meeting place - a dive bar in Palo Alto. Jason also shared his appreciation for the book "How to Get Rich" by Felix Dennis, emphasizing the importance of not counting your money if you want to be rich. Despite some technical difficulties during the podcast recording, the conversation remained engaging and insightful.

    • Democratizing Trading for MillennialsIdentifying untapped markets and taking calculated risks can lead to significant returns in entrepreneurship and investing.

      The investment world is full of opportunities, even in seemingly unlikely areas. In this case, the idea of targeting millennials to trade stocks through a free platform called Robinhood was seen as a risky but potentially lucrative opportunity. The founders' mission was to make trading accessible and democratize the financial industry. However, the success of the platform led to unexpected challenges and consequences, such as a surge in trading activity and potential regulatory issues. Despite these challenges, the investment proved to be highly profitable for early backers, with potential returns of up to 5,000x or more. This story highlights the importance of identifying untapped markets and taking calculated risks in the world of entrepreneurship and investing.

    • The media landscape has changed drastically, with consumers spending more time on mobile devices and easier access to paymentsEntrepreneurs like Elon Musk and Chamath Palihapitiya embody focus and fearlessness in their business ventures. Identifying winners and advocating for them is a valuable superpower.

      The business landscape has drastically changed, particularly in the media industry. The market size has grown exponentially, and consumers' usage patterns have shifted dramatically, with people spending more time on their mobile devices and having easy access to credit cards and app store payments. This has led to the rapid growth of companies like Comcast and Clubhouse. Additionally, the infrastructure for advertising and marketing has advanced significantly, making it easier for businesses to reach their audiences and scale quickly. When it comes to success, the speaker believes that having a singular focus and fearlessness are key attributes, as exemplified by entrepreneurs like Elon Musk and Chamath Palihapitiya. As for himself, the speaker believes his superpower is his ability to identify winners and be an advocate and friend for them.

    • Creating and curating lists can help individuals gain influenceCreating and curating lists can make individuals central players in their industries or communities by opening up access and becoming a notable figure

      Creating and curating lists can help individuals gain influence and become central players in their respective industries or communities. This was discussed in the context of the All In podcast, where the hosts have deep personal relationships and have made the number one tech podcast. The idea of lists as a way to gain influence was also applied to the early days of Silicon Alley Reporter, where Sean made a list of the top 100 Internet people and became a notable figure in the scene by doing so. By becoming the kingmaker and ranking who's who, individuals open up access to them and they become a central player. This can be applied to various industries and scenes, regardless of how arbitrary the list may seem.

    • Creating Controversy and Mentioning Names for AttentionEffectively mentioning names and creating controversy can generate buzz and increase engagement, but ethical concerns and potential consequences must be considered.

      Creating controversy and mentioning names can effectively draw attention and generate buzz. The speaker discussed his experience with ranking people in a list and how it sparked intense reactions and debates. He also emphasized the power of mentioning names in content to increase shares and engagement. The speaker referenced the book "Made to Stick" and its concept of "names, names, names." However, it's important to note that overusing this technique can lead to a breakdown in journalistic standards and ethical concerns, as seen with websites like Gawker and Buzzfeed in the past. The speaker also shared an example of how he used this strategy to distract competitors and gain an edge. Overall, the key takeaway is that creating controversy and mentioning names strategically can be an effective way to capture people's attention and generate buzz, but it's important to do so ethically and with consideration for the potential consequences.

    • Direct communication replacing traditional journalismPeople and organizations are bypassing the press for direct communication with their audiences, leading to a shift in the role of traditional journalism and a need for fact-checking and transparency.

      The role of traditional journalism is changing as more people and organizations turn to direct communication with their audiences. The speaker shared examples of inaccurate reporting and lack of fact-checking, leading figures in tech and business to bypass the press and communicate directly with their followers. The speaker also mentioned the case of Robinhood, whose communication strategy during a crisis was criticized, and suggested that the company could have been more transparent about their financial requirements and the need for a waiting list for new traders. The speaker believes that this trend towards direct communication is here to stay, as people and organizations seek to control their narrative and reach their audiences directly. The press, on the other hand, is struggling to keep up and maintain relevance in this new landscape.

    • Managing risks and challenges in growing companiesCompanies must anticipate and address potential risks before they escalate, adapt quickly to mitigate impact, and maintain trust with stakeholders.

      As companies grow and become influential in their industries, they face increased risks and challenges that can cause significant damage if not managed properly. The example given was the situation with GameStop and AMC, where massive online activity artificially inflated their stock prices, causing potential financial instability. The companies responded by converting debt to equity, effectively saving themselves from potential bankruptcy. However, this episode also highlighted the importance of anticipating and addressing potential risks before they escalate, as seen with the Airbnb example of unauthorized parties causing damage. Ultimately, companies must be prepared to adapt quickly and effectively to mitigate the impact of these challenges and maintain trust with their stakeholders.

    • Paid Communities: Choosing the Right Platform for Engagement and GrowthPaid communities offer value and foster engagement, with Facebook and Slack being popular options for different reasons. The choice depends on specific needs, with Facebook offering ease of use and liquidity, and Slack providing a more focused and organized approach.

      Paid communities, whether on Slack or other platforms, have great potential for engagement and growth. However, the choice of platform depends on the specific needs of the community. Facebook, despite its criticisms, offers the best liquidity and ease of use for community management. Slack, on the other hand, can be a better fit for those who prefer a more focused and organized approach with multiple communities. A simple solution could be the creation of a platform that provides a paywall for communities, allowing them to choose their preferred hosting site while making payment easy and straightforward. The success of paid communities is also seen in the rise of income sharing agreements and consumer subscriptions in various industries like education and entertainment. Overall, the future of communities lies in their ability to provide value and foster engagement, regardless of the platform they choose.

    • Substack's success and challengesSubstack's high fees and potential for big earners to leave for alternative platforms may limit its long-term success. Owning audience through email lists and other platforms is crucial for building long-term relationships and avoiding the risk of losing followers.

      While Substack has had a strong start, its high fees and the potential for big earners to eventually leave for alternative platforms may limit its long-term success. The burnout issue for content creators is also a concern, as maintaining a consistent newsletter can be a grind. Owning one's audience through email lists and other platforms is crucial for building long-term relationships and avoiding the risk of losing followers to other platforms. Industries that may be interested in income share agreements include those where creators or entrepreneurs may not have the upfront capital to start a business but have the potential for significant future earnings. However, the potential downside is that if the creator becomes successful, they may end up giving a significant portion of their earnings to the investor. The debate around the pros and cons of different business models for content creators and entrepreneurs is ongoing.

    • Shift in risk and benefit with ISAs in educationISAs in education offer aligned incentives, high completion and placement rates, and potential for scalability through franchising

      Interest sharing agreements (ISAs) in education offer a shift in risk and benefit, with educators responsible for securing employment opportunities for students. Traditional educational institutions often lack the resources and incentive to effectively prepare students for careers. Companies like Lambda and On Delta, which utilize ISAs, invest as much time in teaching and job placement as they do in education. John Doe, an investor, was drawn to this model due to its aligned incentives, high completion and placement rates, and potential for scalability through franchising. The speaker, having had a disappointing experience with traditional education, aims to create a university based on this ISA model to provide a more effective and modern approach to education.

    • The Future of Education and Work: ISAs and Paid CommunitiesISAs and paid communities could make education more accessible, but it's important to consider fees and interest rates. The pandemic may lead to more travel, nomadic lifestyles, and a shift towards personalized, flexible learning.

      The future of education and work may bring about significant changes, with the rise of Income Shared Agreements (ISAs) and paid communities becoming more prevalent. ISAs could make it easier for individuals to access education and infrastructure, while ISA providers handle the administrative tasks. However, it's crucial to carefully consider the fees and interest rates associated with these services. Furthermore, the pandemic has led many to reevaluate their lives, potentially leading to a surge in travel and nomadic lifestyles, as well as a shift in the perception of education, with more focus on socialization and self-directed learning. Ultimately, these changes may lead to a more personalized and flexible approach to education and work.

    • Exploring Alternatives to Traditional Education: A Father's Experience with MicroschoolingThe pandemic has highlighted the need for affordable, effective education options. Microschools and homeschooling are viable alternatives, allowing parents to hire their own teachers using vouchers and providing quality education for their children.

      The pandemic has led many to question traditional education methods and consider alternative options such as microschools and homeschooling. The speaker shared his experience of setting up a microschool for his daughter, which turned out to be a successful and cost-effective solution. He noted that the high cost of teachers' salaries in the education system and the high teacher-student ratios in public schools could be addressed by allowing parents to use vouchers to hire their own teachers. Despite common misconceptions, the speaker believes that poor families are capable of organizing and providing quality education for their children. He emphasized that the pandemic has created a unique opportunity for entrepreneurs and innovators to create new platforms and solutions in the education sector.

    • Potential of Parent-Run Schools and Caution on BitcoinParents could run schools for increased competition and innovation, but Bitcoin investments may not be worth the risk due to potential emergence of superior technology, diversification advised.

      There's potential in giving parents the opportunity to run their own schools, which could lead to increased competition and innovation in the education system. However, when it comes to investments, the speaker is bearish on Bitcoin and believes that a better technology may emerge that surpasses its current functions as a storage and transfer medium for money. He also advises caution for those heavily invested in Bitcoin and encourages diversification. The speaker also mentioned a past bet he made with Scott Galloway regarding the future success of certain companies, but the specifics were not discussed.

    • Manipulation in the Crypto Market: XRP Insider Trading and Hostile Takeover AttemptsTwo individuals illegally sold $650M in XRP, creating a false demand, and a friend attempted a hostile takeover, but investors defended against the attack. Despite the hype, crypto's primary use remains as a store of value and speculation.

      The crypto market, specifically XRP, has seen its fair share of manipulation and insider trading. Two individuals allegedly sold $650 million in XRP to speculators, creating a false perception of demand and manipulating the market. This is similar to selling stock certificates on the street and goes against SEC regulations. A friend attempted a hostile takeover of XRP by raising funds to short the cryptocurrency and launching a public campaign to encourage XRP holders to trade it for another coin. However, the plan was leaked, and investors were able to defend against the potential attack. Despite the massive investment in cryptocurrencies, its primary use case remains as a store of value and a vehicle for speculation. The idea that crypto would revolutionize various industries and change the way we live has not materialized, as many of its proposed benefits, such as immutability, do not outweigh the costs of decentralization.

    • Democratizing Investment OpportunitiesThe future holds potential for non-accredited investors to participate in private markets through sophistication tests and proven platforms, like equity crowdfunding and crypto investments.

      There's a strong belief in the potential of expanding investment opportunities beyond accredited investors. The speaker expresses skepticism towards the lack of tangible use cases for some current investment platforms, but is optimistic about the future of non-accredited investors participating in private markets. He believes that a sophistication test could be a solution to include these individuals, who may not meet the financial requirements but possess valuable financial knowledge. The speaker also shares his experience with equity crowdfunding platforms like SeedInvest and acknowledges the potential of crypto investments. Despite the challenges, he remains hopeful for the future of democratizing investment opportunities. Additionally, the speaker shares his appreciation for podcasts like "All In" and the impact they can have on reaching a large audience.

    • Finding Opportunities for Growth During the PandemicThe pandemic has brought about new projects and opportunities for personal and professional growth. Adapting to new circumstances and finding innovative solutions can lead to increased deal flow, a larger syndicate, and optimism for the future.

      The pandemic has presented opportunities for personal and professional growth. The speaker shared how he started new projects, such as the "All In" podcast and remote demo day, which led to significant success. These initiatives resulted in increased deal flow and a larger syndicate. Furthermore, the speaker expressed optimism about the end of the pandemic and the availability of vaccines. He also shared his personal experience with the virus, having lost one friend but knowing several people who have received the vaccine. The speaker concluded by encouraging listeners to look for travel investment opportunities as the world begins to recover from the pandemic. Overall, the speaker's message emphasizes the importance of adapting to new circumstances and finding opportunities for growth, even in challenging times.

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    The GameStop Guy Has Returned… (And Has A New $210M Bet)

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    Episode 593:  Sam Parr ( https://twitter.com/theSamParr ) and Jason Fried ( https://x.com/jasonfried ) open up about personal finances, raising kids around wealth and dealing with risk.  — Show Notes: (0:00) Sam and Jason play Would You Rather... (5:15) Loosening the grip on the stick (12:35) The pale blue dot (14:03) Why does the businessworld deserve our best lessons? (18:30) Early days vs. vs. middle days vs later days (24:47) "A founder's job is to inject risk" (29:36) “Cool wears off but useful never does” (31:07) Striking balance with a business partner (34:14) The value of talking about money (37:28) Navigating luxury with kids (40:08) Midwestern values on blast (43:39) The truth about luck (46:55) Staying up vs. staying off (49:45) New insights from old biographies — Links: • [Steal This] Get our proven writing frameworks that have made us millions https://clickhubspot.com/copy • The Most Important Thing - https://tinyurl.com/9ym3xw5b • Peter Lynch books - https://tinyurl.com/2nf87pzb • The Pale Blue Dot - https://www.planetary.org/worlds/pale-blue-dot • The Messy Middle = https://tinyurl.com/2paw5jmk • Sam’s List - http://samslist.co/ • Newspapers.com - http://newpapers.com/ • Pessimists Archive - https://pessimistsarchive.org/ • Grab HubSpot's free AI-Powered Customer Platform and watch your business grow https://clickhubspot.com/fmf — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth — Check Out Shaan's Stuff: Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano
    My First Million
    enJune 05, 2024

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