Share this post

🔑 Key Takeaways

  1. Vanta Trust Reports provide a faster and more transparent compliance process for companies seeking certification. It helps strengthen relationships with customers and partners by proving their security.
  2. Pursuing your passion from an early age can lead to great opportunities and success, even if you don't excel in traditional education. Mentors and networking can also bring new opportunities to pursue your passion and turn it into a career.
  3. With perseverance and a hunger to learn, anyone can become successful in an industry they're passionate about. Don't be afraid to challenge yourself and try new things.
  4. A successful podcast show requires chemistry and connection between the host and guests, even if they are successful in their own fields. 'All-In' podcast's success lies in bringing together diverse perspectives and the natural rapport of its hosts.
  5. All-In's success is due to its ability to create intimate connections with its audience through character-driven banter, while also providing insights on world events. Real fights and arguments lend to the authenticity of the show.
  6. All-In has made moderation acceptable in politics, while emphasizing privacy and competence in leadership. They believe in coalition building and dislike the two-party system's limits on independent thinking.
  7. Seek out those who share your beliefs and values, engage in healthy debate to foster growth, and embrace technology to access education and career opportunities in a more equitable world. Connect and build a supportive community to navigate the world.
  8. Founder University offers a largely free 12-week course to teach people how to start businesses, with an optional fee of $700 and a money-back guarantee. Diversity thrives in Silicon Valley, focusing on what you build and traction. The All-In Podcast provides unique insights from guests to help entrepreneurs stay ahead.
  9. Creating engaging podcast content requires a balance of process journalism, charisma, and relatability. An effective moderator acts on behalf of the audience to help them understand complex topics while striking a balance between debate and conversation.
  10. Successful podcasts strike a balance between entertaining their audience while also educating them. Engaging content should challenge listeners while avoiding complex topics. Appreciating the benefits of the tech industry is crucial for positive discourse.
  11. Free market systems can lead to innovative solutions for progressive ideals, such as higher salaries and offering benefits. Focusing on passion projects can lead to greater energy and productivity. Brex offers a seamless, compliant global solution for card and expense management, perfect for startups and enterprise-grade companies.
  12. Surround yourself with a passionate team, have energizing conversations, and innovate work processes to achieve success. Stay committed to your passion, work hard, and continually improve to reach your goals.
  13. Jason Calacanis is using 506(c) to raise LP funds publicly and democratize venture capital. He believes more people should consider investing in the asset class and predicts a future test for accreditation. With 265 syndicate deals, he is a pioneer in making VC more accessible.
  14. Building a strong network is crucial for a successful venture fund. Fund managers can leverage their connections and online presence to gain interest from potential investors. It's important to establish partnerships and focus on building a strong track record and reputation. Venture capital involves risks, but it also offers high rewards.
  15. Investing is not only about making money, but also finding fulfillment in helping start-ups succeed. Valuing accountability over personal happiness and creating personal relationships are equally important.
  16. Identifying world-class design, product velocity, and roadmap evaluation can increase chances of success in early-stage investing. Teaching these principles can mitigate risks and help investors make smarter decisions.
  17. Understanding public market cycles and trading public stocks can inform investment decisions for early stage investors. Careful analysis and study of public companies' buying decisions can provide valuable insights, but caution should be exercised when joining a public board during an unstable market.
  18. Adobe's acquisition of Figma helps them tap into Figma's strong network effects and opens up opportunities for business development, sales, and operations. It also removes the risk of Figma becoming a competitive software stack while providing meaningful revenue multiple.
  19. Explaining bets is cooler than talking book. All-In summit, top tech event, worth up to $100m. Possible new event under different name considered. After All-In call-in show launched. ADHD app making great progress valued at $50m as a top 40 podcast.
  20. Create deep, unique content to target specific audiences rather than try to appeal to everyone. Take inspiration from media personalities like Howard Stern and consider experimenting with different types of media like reality TV to engage your audience.
  21. Jason Calacanis prioritizes his legacy over immediate financial gain, while Tiny's approach allows for mutually beneficial partnerships between founders and investors.
  22. Successful generational transitions and legacy building are vital in venture capital. A Venture Capital Hall of Fame can honor top capital allocators and their contributions to the industry's growth and success.
  23. The inductees into the venture capital hall of fame are chosen based on their impact on the industry, game-changing ability, and potential for great returns. A small group of experts who know the industry well are responsible for making the final call.
  24. Capital allocators have the power to move humanity forward by supporting visionary founders, and recognizing the impact of investors like Ron Conway and stories of successful turnarounds can provide inspiration. Casual conversations can provide fresh perspectives.
  25. The SmartLess podcast shows that having a surprise celebrity guest adds charisma to a show. Spotify's strategy for driving new subscribers by limiting certain podcasts and entering the audiobook market. Craigslist remains a popular choice for buying used furniture.
  26. Securing financial stability can bring immense relief and buying companies can be a path to success. Consider selling your company to Tiny, a rising star in the industry, to attain financial independence.
  27. Sometimes, owning a high-performance machine that brings you joy is more important than owning a flashy one. The advancements of electric cars suggest a bright future, while feedback is crucial for growth and improvement.

📝 Podcast Summary

Vanta Launches Real-time Security Updates with Vanta Trust Reports

Vanta has launched Vanta Trust Reports which gives real-time updates of a company's security practices and is a much more transparent compliance process than a SOC 2 certification which is done once a year. Vanta Trust Reports are loved by companies that are looking to achieve compliance certification within weeks instead of months. The launch of Vanta Trust Reports is exciting for companies as it will help them prove their security and strengthen their business relationships with customers and partners. Acquired Sessions is a podcast where the hosts discuss various topics in an unscripted manner. The hosts thanked Vanta, the leader in automated security and compliance software, for sponsoring their podcast.

From Computer Nerd to Tech Entrepreneur: The Story of Jason Calacanis

Having a computer at home during the early ages of personal computing and gaming shaped entrepreneur Jason Calacanis' interest and passion for technology. Even though he was a bad student, his love for computers and gaming led him to hack software and create his own zine. Eventually, his writing caught the attention of Jerry Colonna, a prominent figure in the tech industry and became Calacanis' mentor. Through Colonna, Calacanis met Fred Wilson and went on to work in Flatiron, which became a big success in venture capital. This goes to show that a passion for something can start from an early age and can lead to successful and fulfilling careers later on.

Jason Calacanis: From Publishing to Podcasting

New York had a lot of good companies brewing, and Jason Calacanis capitalized on it by becoming the king of technology with two magazines, two conferences, and two email newsletters. He grew his publishing business to $10M in revenue with 75-100 people working for him when he was just 27 years old. He taught himself everything without knowing anything about how to run a magazine or ad sales. His journey was featured by The New York Times, Charlie Rose, and The New Yorker. Today, Jason Calacanis considers podcasting his greatest medium. He started All-In with Chamath in 2018, which he thought they would do ten times, surpassing his wildest expectations.

Chemistry and Connection: Key to a Successful Podcast Show.

The success of being a great founder or person in tech does not necessarily make you a compelling podcaster. A good guest and a great rapport with one another is important in creating a successful podcast show. The idea of 'All-In' was born out of a poker game that Jason Calacanis and his friends had hosted, which became a frequent topic on his podcast show. During the pandemic, people wanted information and perspective, and the 'All-In' podcast show provided that in a unique way by bringing together people from different political backgrounds and perspectives. The success of the show is attributed to the natural chemistry between Jason, Jim, David, and Friedberg.

The Immense Popularity and Impact of the All-In Podcast Beyond Finance and Tech Sectors

The podcast All-In has gained immense popularity, transcending beyond just finance and tech sectors, now impacting different walks of life, such as being recognized by a dentist in Reno. The show's success is attributed to its ability to create characters, resulting in an intimate connection with its audience; however, the fights and arguments on the show are real and not scripted. Jason, David, and Ben banter about financial status, with Jason being the poorest guy on the show, and the team has created a character of JCal, the guy who wants to be like his colleagues. The All-In team's success is not solely based on their fame but their ability to provide insights on significant world events and their ability to create engaging conversations.

All-In Podcast Hosts and Their Beliefs

All-In has brought notoriety to its hosts, especially Friedberg who was previously an under the radar guy, but now loves the attention. Sacks has taken the brunt of the criticism on the show but is passionate about unpopular tech topics, which might have caused him deal flow on the margins, according to Jason. Furthermore, the podcast has moved many people towards the center and made it okay to admit to being a moderate. The hosts believe in the importance of staying out of people's lives and competence in leadership. The two-party system requires coalition building and people are not allowed to think independently about anything else. Lastly, the hosts dislike Donald Trump and believe that he has no business being in any political office.

Building a Supportive Community Through Shared Beliefs and Technology.

The conversation focuses on the idea of being part of a community, whether it is political, technological, or social. People tend to seek people who share the same beliefs, goals, and values to find a sense of belonging. The hosts showcase how disagreements can still lead to learning and growth, an essential aspect of a healthy debate. Additionally, the discussion highlights that education and career opportunities are more accessible today than ever before, thanks to technology. The hosts urge people to recognize that while the world is still unfair, it has never been this equitable. It is essential to play the game on the field, learn, connect and build a supportive community as one tries to navigate the world.

Founder University and All-In Podcast: Resources for Starting Your Own Business and Staying Ahead of the Game

Founder University teaches people how to start companies in a 12-week course that is largely free. The program charges $700 for those who want to build a company, and if they complete the course, they get their money back. Over 90% of people complete the course, and some are even invested in by the program to help start their own businesses. Silicon Valley is now more diverse and open, and people care about what you have built and your traction, rather than where you went to school or where you live. All-In is a podcast that has a slight information edge due to the guests they interact with, and they provide new insights that aren't widely available yet.

Tips for Engaging Podcast Content and Effective Moderation

The key to successful podcasting is delivering compelling content that makes history fun. Relationship and charisma also play a major role in engaging the audience and keeping them involved. While process journalism may take time to reveal the complete story, it keeps audiences invested in the topic. Moderating a podcast is an art that requires an intimate sense of the audience's edges, to ensure they remain engaged. The role of a moderator is to act on behalf of the audience, helping them understand complicated topics. Chamath's engagement with complex topics showed that it's important to strike a balance between debate and conversation and making content relatable to the audience is the key to a successful podcast.

Balancing Entertainment and Education for Podcast Success

Creating a successful podcast requires finding the right balance between entertainment and education. The hosts must ensure that their listeners are taking the stairs and not just jumping into unfamiliar and complex topics. While some podcasts may be enjoyable but not mentally challenging, others require full attention and engagement from the listener. Additionally, the conversation shifted towards the challenges of living in San Francisco and how politics and regulations are affecting the tech industry. Some politicians are quick to criticize successful founders and entrepreneurs, despite the jobs and wealth they create. This highlights the importance of understanding and appreciating the contributions of the tech industry to society.

Free Market and Innovative Solutions for Progressive Ideals

Bezos has shown how free markets can drive salaries and benefits up, as evidenced by his implementation of policies that are often championed by progressives, such as providing free college, increasing minimum wage to $22, and offering universal healthcare, to Amazon employees through a competition-driven approach. Similarly, Brex offers a complete solution for corporate card and expense management that's global, compliant, and seamless, with 24/7 enterprise-grade support, ideal for startups and enterprise-grade companies expanding internationally or dealing with independent contractors all over the world. Choosing to focus on things that bring joy and purpose can lead to higher levels of energy and productivity, as exemplified by Jason's own experience and dedication to his passion projects like his podcast.

Building a Thriving Work Environment

Having conversations that energize you and finding joy in your daily work can lead to significant success. Creating a team of people who share your passion and work ethic can help you achieve even greater results. You can also innovate your work processes to make the most efficient use of your time, such as scheduling investment team meetings and finding ways to handle large numbers of founder meetings efficiently. It is important to find what drives you and commit to it, even if it takes a lot of hard work. Success can come from doing what you love and striving to constantly improve.

Jason Calacanis on Making Venture Capital More Accessible

Jason Calacanis is raising LP funds publicly through 506(c), which allows him to tell people he is raising a fund. He has raised $10 million by doing hundreds of meetings and raising in three months to six months with his past funds. He believes now is the time to democratize venture capital and wants more people to consider investing in the asset class. Qualified purchasers and accredited investors can invest up to $10 million and $200,000 respectively. He also believes that there will be a test for accreditation in the coming years, where investors could be considered sophisticated if they take a course. He has done 265 syndicate deals, the largest amount of anybody.

Building a Strong Network: Key to Successful Venture Fund

Taking action and building a strong network can make a significant difference in the success of a venture fund. Rather than waiting for institutional investors, fund managers can leverage their own connections and online presence to gain support and interest from potential investors. It's important to focus on building a strong track record and reputation, as well as considering unique ways to attract capital such as establishing partnerships with endowments or state pension funds. While there may be risks involved in investing in start-ups, the potential for high rewards makes it an attractive opportunity for those willing to take the chance.

Investing for Fulfillment and Personal Meaning

Investing is not just about making money, but also finding happiness and fulfillment in what you do. Jason aspires to help start-ups at the earliest stages, which he finds to be the rush. He values being accountable to his LPs, rather than taking very little work and doing only what brings him pure happiness. His track record shows that he has invested in early-stage companies that eventually became successful, such as Uber, Calm, and Vanta. He takes pride in supporting start-ups that others may not believe in, and he even helped save Calm from shutting down. For him, investing is not just about the money, but also about creating relationships that have personal meaning.

Factors to Consider Before Investing in Early-Stage Startups

Investing in early-stage startups requires identifying potential factors for success and risk. Identifying factors, such as world-class design and product velocity, can increase the chance of success. Calm and Robinhood are examples of companies that succeeded due to their top-tier user experience. Additionally, evaluating a company's roadmap can indicate their potential for future growth. Teaching these principles to new investors can increase their chances of success and mitigate potential risks. Investing in companies early-on before they achieve product-market fit and generate revenue is considered true angel investing. Knowing the right factors to track helps investors make smarter decisions and identify red flags that could kill companies.

The Importance of Public Market Cycles in Early Stage Investing

Understanding public market cycles is helpful in driving how much variability there is and in making investment decisions for early stage investors. Comparison to public comps may not be suitable as it can change over time. Trading public stocks is beneficial in understanding the experience of private and public companies' founders, as well as the board's decision-making process. It is good to be careful in joining a public board during the market's unstable state, but it is helpful to analyze and study public companies' buying decisions as Adobe bought Figma and its effect on the market.

Adobe's Acquisition of Figma: A Strategic Move to Strengthen Customer Channel and Network Effects.

Adobe's acquisition of Figma was a smart move as they recognized their customer channel and the potential of Figma's strong network effects. Even though Adobe paid a premium for the acquisition, it removes the risk of Figma potentially building a competitive software stack to Adobe. Adobe is not planning to ruin Figma, but to let it be and just provide access through their channel. Figma's network effects will help open up the aperture of users beyond just designers to include business development, sales, and operations. Any company with such strong network effects within an organization deserves a meaningful revenue multiple. The best M&A strategy is when you look like you robbed the bank, but five years later, it looks like you robbed the founder.

All-In Summit a Success and Plans for Future Events

Explaining your bets is cooler than talking your book. The All-In summit was a great success, and Jason plans on doing it again. The event was number one in tech and could be worth up to $100 million. The boys are deciding if they want to do it again under the All-In brand or create a new one. Friedberg is a bit of a blocker, but he said he would support a new event with a different name. Jason also started doing a call-in show called After All-In. David's ADHD app is making great progress, and it's worth at least $50 million as a top 40 podcast.

The Importance of Niche Podcasts and Unique Content Creation

Niche podcasts are not supposed to appeal to everyone and in order to make it bigger, it has to be worse for founders. The internet has given rise to various kinds of media personalities like true crime readers or Ben Shapiro dunking on libs, but it's important to create unique and deep content to target a specific audience. Howard Stern is the king of all media and his technique of creating characters and branding them is an inspiration for many. A reality TV show in the vein of Gordon Ramsay could be entertaining and educational for the audience, especially if it's about incubating companies and would be completely different from the fundraising aspect of Shark Tank.

Jason Calacanis' goal of becoming the greatest investor of all time and Tiny's unique approach to acquiring businesses.

Jason Calacanis is more focused on being the greatest investor of all time than earning max dollars. He has already achieved financial stability, has paid for his kids' college education, and can have whatever he wants. He wants to be remembered as one of the greatest investors in history and be in the conversation with Doug Leone, Moritz, John Doerr, and Gurley in the Mount Rushmore for investors. Tiny is acquiring businesses that are not suitable for venture capital investment and partnering with their founders to own these companies in perpetuity. This way, VCs get their money back, and the founders get to keep running their business and serving their customers while Tiny can help them grow the business.

Recognizing the Top Venture Capital Allocators

The discussion revolves around the Mount Rushmore of venture capital firms and the requirement for three successful generational transitions. It is suggested to create a Venture Capital Hall of Fame to honor and induct the top 25 capital allocators every year. While there are museums like the computer history museum, there is no such recognition for top capital allocators. The conversation highlights the impact of firms like Kleiner, Sequoia, Benchmark, Techstars, and Y Combinator on the industry. The talk emphasizes the significance of successful generational transitions to legacy building in the venture capital industry. The discussion reveals the importance of recognizing the contributions of top capital allocators for their impact on the industry.

Impact is the Ultimate Criterion for the Venture Capital Hall of Fame

When considering who belongs in the venture capital hall of fame, the key factor is impact - on the game, on the industry, on the people involved. Founding fathers of the industry, like Arthur Rock, are just as important as modern-day angels like Paul Graham and Jeff Bezos. While some firms may feel more soulful and relationship-driven, the common thread for all inductees is their impact on the industry. While there may be some debate over who belongs and who doesn't, ultimately the decision should be made by a small group of experts who know the industry well. And while venture capital is volatile, the potential for great returns and the ability to change the game make it a truly exciting field.

Importance of Impact in Hall of Fame Inductee Selection & the Significance of Capital Allocators

The process of choosing inductees into a hall of fame based on impact, rather than just returns, is important. Capital allocators have a special function in the world and can help move the human species forward by providing fuel and belief to founders who may have otherwise given up. It's important to understand the significance of investors like Ron Conway who have had a big impact in the industry, and the stories of Don Valentine and others who have taken companies that were on the brink of failure and turned them around. The casual format of discussing tech business over a glass of wine with friends of the pod can provide a fresh perspective and an opportunity to go deeper on different topics.

SmartLess Podcast, Celebrity Guests, and the Future of Audio Entertainment

The podcast SmartLess featuring surprise guests has become a big hit and is ranked among top 10 or top 25 podcasts. However, the guest is just a prop and the show is actually about the hosts. While it doesn't have to be a surprise, having a celebrity guest adds charisma that the tech industry doesn't have. The hosts express interest in doing a similar show for the tech industry. Also, Spotify doesn't allow Joe Rogan and Call Her Daddy on iTunes because they want to drive new subscribers for Spotify. The next piece for Spotify is audiobooks. Craigslist is a preferred choice for buying used furniture for Jason and David recently furnished a room with it.

Securing the Bag with Tiny: How Buying Companies Can Create Wealth

Securing the bag i.e., making a lot of money is a life-changing experience for those who have lived with the fear of being broke and in debt all the time. It brings a sense of relief that their family will never have to worry about money again. It's like opening up a tiny bag, filled with diamonds and cash. In terms of business, buying companies is a path to create wealth and become like the Berkshire of the internet. It is a good time to sell your company to get the monkey off your back of venture capital as Tiny, a company that buys companies, is doing a good job and creating success stories like the AOL, Weblogs exit.

The Power of Simple Joy and Feedback in Growth

The key takeaway from Jason Calacanis' story is that sometimes, the simple joy and excitement of owning a high-performance machine like a Corvette can be more important than owning a flashy Ferrari, especially when you get a good deal on it. Additionally, electric cars have come a long way since the first prototype, as evidenced by Jason's experience racing the Tesla Roadster against the Corvette, and as technology continues to advance, we can expect even more impressive developments in the industry. Lastly, opportunities for growth and improvement often come from feedback, as seen in's launch of their 2022 survey to better understand their growing audience.