ACQ Sessions Jason Calacanis

In this engaging episode of "Acquired," hosts David Rosenthal and Ben Gilbert sit down with serial entrepreneur and angel investor Jason Calacanis for a candid discussion that spans his career, the venture capital landscape, and the future of media. Calacanis shares personal stories, including the emotional moment he "secured the bag" with the sale of Weblogs, Inc., and his unconventional path from considering a career in law enforcement to becoming a leading tech investor. The conversation also delves into the success of his podcast "All In," his views on the venture capital "Hall of Fame," and his aspirations to leave a lasting impact on the industry. The episode concludes with a lively debate about the value of companies like Andreessen Horowitz and the potential for a venture capital museum, underscoring Calacanis's passion for the craft of investing and the power of storytelling in tech.

• The podcast starts in a casual manner, with the hosts bantering and joking about not revealing sensitive information.
• They toast to the beginning of the session and mention the unique nature of their gathering.

"Magazine. Yeah, that's how I started. Yeah. You see, magazines was like the original platform for. Wait, are we." "I guess we started." "This is the trick. We've just been. Welcome to a quiet session." "No, definitely not. Definitely not. We don't want to tell people where the bodies are buried. Well, cheers, boys." "Cheers." "Here we go. Is this the first one or this." "Is the first in real life, but I think this is our 9th, 10th together. Something like that."

The quotes show the hosts reminiscing about the origins of their careers and setting a relaxed tone for the podcast.

• Acquired sessions is a concept where the hosts ditch the script and have an informal conversation with people they know well.
• It's a deviation from their usual, more structured episodes.

"Acquired sessions is normally on the show. We are like so scripted." "And we have a great time. We do four hour episodes. It's awesome. But we're like, for folks like you who we know really well, what happens if we throw out the script and." "Just chop it up?" "David Rosenthal unplugged." "Literally. MTV unplugged."

These quotes highlight the intention behind Acquired sessions, which is to have unscripted, free-flowing conversations.

• Pilot is an accounting firm that takes care of financial, accounting, tax, and CFO services for startups and growth companies.
• The firm has grown significantly and is backed by major investors.

"Our next sponsor for this episode is one of our favorite companies and longtime acquired partner pilot for startups and growth companies of all kinds." "Which is wild because when we started working with them way back when, they were just a startup themselves, and now they're a billion dollar plus company backed by Sequoia, index, stripe, and even Jeff Bezos himself."

The quotes describe Pilot's growth and prominence in the startup ecosystem, emphasizing its value as a service provider.

• Vanta is a company that simplifies the compliance process for other companies.
• The hosts discuss Vanta's new feature called Vanta Trust reports and its potential benefits.

"We are huge fans of Vanta and their approach to the whole compliance process. Sock two HIPAA, GDPR and more." "Vanta was already the best place to check the box and get security compliance certified. But now you've just launched Vanta Trust reports, which take things even further."

These quotes explain Vanta's services and introduce the new Trust reports feature designed to help companies with compliance and security.

• Jason Calacanis shares his personal background, including his father's tax issues and his own early career.
• He discusses his work fixing laser printers, his underperformance in academics, and his early exposure to computers and video games.

"Grew up in Brooklyn, my dad had his bar seized by the feds because he didn't pay his taxes during the 1987 crash." "And I was like, well, I guess I'm going to school at night and I'm going to work during the day." "I was a bad student. I was always that student who underperformed." "And then I happened to hack some software."

These quotes provide insight into Jason's challenging upbringing and his initial forays into technology and entrepreneurship.

• Jason pivoted from technology to publishing, starting with a zine called Cybersurfer and eventually creating Silicon Alley Reporter.
• He met Jerry Colonna and Fred Wilson, which led to opportunities in venture capital and further involvement in the tech industry.

"I created a zine. I was like, I'm going to be a magazine publisher." "I met Jerry Colona at Internet World, the first one." "I met Fred Wilson, and I would go up to them, and they were doing, JPMorgan was going to back them for their venture firm."

Jason's quotes trace his path from tech enthusiast to influential figure in the tech media and venture capital spaces.

• Jason and Chamath Palihapitiya started the All-In Podcast after realizing their good rapport on Jason's other podcast.
• The podcast was initially expected to be short-term but gained popularity during the pandemic.

"Chamath calls me coming out of the studio... he said, I want to do this pod with you." "We should call it all in. Like we should come with a poker name. He's like, yeah, great. Like a raise or something. It's like, all in."

These quotes recount the casual yet decisive moment that led to the creation of the All-In Podcast.

• The All-In Podcast has grown significantly, reaching audiences beyond the tech industry.
• Jason discusses the podcast's ability to foster debate and friendship despite differing opinions.

"The pod's gotten very big." "It has nothing to do with finance or tech anymore. It is tipped over into colleges." "I think what messes people up is the fact that I actually just think Donald Trump is a horrible human who you should do no business with."

Jason's quotes reflect on the podcast's unexpected success and its role in encouraging open dialogue among people with diverse viewpoints.

• Jason Calacanis emphasizes the importance of inspiring people to create companies and learn.
• He points out that educational resources from prestigious universities are available online for free.
• Jason believes in the democratization of knowledge and the potential for anyone to learn and build businesses.

"And the time I create the most controversy is when I'm like, I believe anybody can do it. And people are like, you're so wrong. And I'm like, am I? Because I go on YouTube and you could type in any topic that you want to learn and you can learn it."

The quote suggests that Jason challenges the notion that entrepreneurship is exclusive to a select few and underscores the wide availability of learning resources online.

• Jason argues that the world has become more equitable with increased access to information and opportunities.
• He criticizes the narrative that the world is unfair, while acknowledging that inequalities still exist.
• The conversation touches on how free online courses and resources have leveled the playing field for learning and job opportunities.

"Equitable, yeah, but people want to spread a narrative that the world is. And like, I watched the world become so fair and so just and so much information and opportunity become available that I'm like, wait a second."

Jason is refuting the idea that the world is overwhelmingly unfair, pointing out the significant progress made in terms of fairness and opportunity.

• Jason teaches at Founder University, a course designed to teach people how to start companies.
• The course is structured to incentivize completion and engagement, with a refundable fee for those who complete it.
• Jason emphasizes the diversity and openness in Silicon Valley, challenging the belief that only Ivy League graduates can succeed as founders.

"I teach founder university now. I have a course where I teach people for twelve weeks, or I should say I have a team that teaches it, and I'm going to actually teach it myself."

Jason highlights his commitment to educating aspiring entrepreneurs through Founder University.

• Jason describes Silicon Valley as a meritocracy, especially post-pandemic, where metrics, product, and skills matter more than background.
• He acknowledges the controversy surrounding the term "meritocracy" but stands by his observation based on his experience with founders.

"It is post pandemic. All people care about is like, show me your metrics. Show me the product. Show me your team. What are your skills? Great. Let's go. What's your growth rate? It's basically become, like, as beautiful of a meritocracy as I've ever seen."

Jason is asserting that Silicon Valley's focus has shifted to tangible achievements and performance rather than pedigree or background.

• Ben Gilbert and David Rosenthal discuss the appeal of the All-In Podcast, attributing its success to a combination of insider knowledge, entertainment, and relationships.
• Jason acknowledges the podcast's unique position in providing insights and information not readily available through other sources.

"All four of us are information junkies with a lot of research and teams that."

Jason is explaining that the hosts of the All-In Podcast are deeply invested in gathering and sharing information, contributing to the show's depth.

• Jason expresses dissatisfaction with California's political climate and its lack of appreciation for the tech industry.
• He contrasts San Francisco's approach to taxing wealthy founders with Miami's welcoming attitude toward entrepreneurs and venture capital.

"You could go change the tax code. It's fine. Raise the minimum wage. Like Bernie Sanders and Elizabeth Warren attacking Bezos endlessly. And then Amazon starts paying 22 an hour, gives you benefits, and pays for your college."

Jason is criticizing the negative attitude towards successful entrepreneurs in San Francisco and highlighting the positive changes companies like Amazon have made in response to political pressure.

• Jason is raising a new venture fund and discusses the process of democratizing venture capital by allowing more accredited and qualified purchasers to invest.
• He reflects on the changing landscape of venture capital fundraising, with a focus on transparency and public engagement.

"So like this guy, Mac, the VC... he just told me, I just did like hundreds of meetings. I did like five meetings a day for a year and I raised my, whatever, $10 million."

Jason is sharing an example of how hard work and dedication can lead to successful fundraising, even for those who may not have traditional access to venture capital.

• Jason reflects on the passing of his friend Tony Hsieh and his own realignment of priorities, focusing on activities that bring him joy.
• He discusses his love for podcasting and his strategic approach to managing his workload and his team.

"Well, I find great purpose in what I do. And when my friend Tony Shea died, I really thought deeply about what I wanted to get out of the rest of my life."

Jason is sharing how the loss of a friend prompted him to reassess his life goals and focus on what he finds most fulfilling.

These notes capture the essence of the conversation, highlighting the key themes discussed by Jason Calacanis, Ben Gilbert, and David Rosenthal in the transcript. Each quote is accompanied by an explanation to provide context and clarity on the topic.

• There are various ways to create content and build a track record, including starting a blog, creating a founder university, or being an advisor to startups.
• Building a track record is essential for establishing credibility and authority in the startup ecosystem.
• Engaging in content creation and advisory roles can lead to opportunities and recognition within the industry.

"And it doesn't mean you have to start a podcast, you could be a blog, you could do whatever, create founder, university, whatever it is. You can do any of those things. You can have a track record, you can be an advisor to startups, whatever it is."

This quote emphasizes the flexibility in building a track record and the importance of contributing to the startup community in various forms.

• Institutional investment, such as large checks from fund-to-funds and endowments, can be significant for fund managers.
• Having institutions invest in a fund can add a layer of seriousness and responsibility due to the nature of the capital being managed.
• The impact of institutional money is not just financial; it can provide additional meaning to the work of fund managers, especially if the institutions have a social impact focus.

"I've had $5 million checks, $10 million checks in the fund from fund to funds and institutions. You'd know, but I would very much. At some point, I don't need it, but it would be meaningful for me."

Jason Calacanis expresses the significance of receiving large institutional investments and the personal meaning it can bring, especially when the institutions have a social impact or personal connection.

• There is a perceived value in having external validation, such as managing outside money, which can feel like playing a sport in a major arena as opposed to practicing alone.
• Sharing one's investment track record and future plans with the public can be a way to gain credibility and attract more investors.
• The idea of public accountability can be both a motivator and a source of pressure for fund managers.

"I think it's like playing in the bubble with nobody in the stands versus getting on the court at Madison Square Garden and there's people in the stand."

Jason Calacanis compares managing one's own money to managing external funds, suggesting that external validation can feel more rewarding and significant, similar to the difference between playing a sport alone and in a major sports arena.

• Raising funds publicly can be a productive strategy, but it also comes with the risk of failing in public.
• There is a natural tension between managing a traditional fund with LPs and investing one's own money through syndicates, each with its own set of trade-offs.
• The decision to raise funds publicly or privately can hinge on personal goals, such as seeking happiness and fulfillment versus maximizing wealth.

"The freeing thing is I looked at the model and I said, you know what I could do? I could just invest my own money in each company and then syndicate them and never have another LP."

Jason Calacanis discusses the possibility of investing without a traditional fund structure, highlighting the freedom it offers but also the trade-offs compared to raising funds publicly.

• World-class design and product velocity are among the key factors to consider when evaluating potential investments.
• World-class design refers to a product that stands out in its category for its aesthetics and user experience.
• Product velocity is the rate at which a product evolves and improves, which can be a crucial indicator of a company's potential for success.

"And world class design, to me is if you were to look at all the companies in the space, this one would have the best design, or this would be one of the top 10%."

Jason Calacanis defines world-class design as a distinguishing feature of top-performing companies in their respective spaces, indicating the importance of design in his investment decisions.

• Podcasts can serve as a platform for venture capitalists to share their experiences, investment strategies, and insights into the startup world.
• The success of a podcast can be measured not just by listener numbers but by its impact on the target audience, such as founders and capital allocators.
• Podcasts can be a tool for personal branding and can lead to economic opportunities, such as attracting larger funds or investment deals.

"This week in startups is a juggernaut as well. Yeah, that was out for ten years and all in is what is that. Like a quarter million listeners or something?"

Jason Calacanis reflects on the success of his podcast, "This Week in Startups," and its impact on the startup community over the years.

• The "All In" podcast has significant enterprise value due to its reach and influence in the tech and venture capital community.
• The economic value of the podcast extends beyond direct monetization and includes the potential for the hosts to secure deals and investments as a result of the show's exposure.
• The podcast's approach to discussing investments and the startup ecosystem resonates with the audience and adds to its value.

"It's worth 50 million, to answer your question, 50 to 100 million as a top 40 podcast. It's worth at least 50 million on its own, though."

Jason Calacanis estimates the value of the "All In" podcast, highlighting its significant worth in the podcasting and venture capital space.

• Jason Calacanis was approached by major reality TV folks due to his successful endeavors.
• A pilot for an NBC show featuring Jason incubating companies was produced but never aired.
• The show's cancellation was linked to the Harvey Weinstein scandal, affecting all associated IP.
• Jason finds joy in media work and prioritizes it over maximizing money at this stage in his life.

"But a very major reality tv folks reached out, I think, in part because you doing so well."

This quote indicates that Jason's success has attracted attention from reality TV producers, suggesting his ventures are both entertaining and educational.

"The NBC show I had done the pilot for, which never made it on air. What was really good was really about me incubating companies, and they spent like, four or $500,000 doing the pilot."

The quote explains that Jason was involved in a high-budget pilot for a show about incubating companies, highlighting his expertise in the startup industry.

"Was in his company, all the IP is dead because he's a monster. And so anything associated with it."

Jason is acknowledging the impact of the Weinstein scandal on his NBC show, as any intellectual property associated with Weinstein's company was tainted.

• Jason is not driven by the pursuit of maximum wealth but rather by making his life count.
• Having achieved financial security, Jason's focus has shifted to impact and enjoyment.
• He aims to be remembered as one of the greatest investors, valuing legacy over financial gain.

"I'm not going for Max dollars. So when the guys break my chops about that, I'm like, guys, it's not my priority. Literally, maximizing money is like, well, also."

Jason is expressing that maximizing wealth is not his top priority, suggesting that he values other aspects of his career and life more.

"I literally do not care about a third home. I have a ski house. I have my regular house. It's good. I'm good."

This quote emphasizes Jason's contentment with his current wealth and lifestyle, showing no desire for excessive material accumulation.

"I do want to be the greatest investor of all. Like, to me, that's meaningful or be one of the. I know I'm Mount Rushmore for angels. I want to be mount rushmore for all investors."

Jason's ambition is to be recognized as one of the greatest investors, indicating that he seeks a lasting legacy in his field.

• The conversation shifts to the venture capital industry and its key players.
• Tiny, a company that acquires Internet businesses, is likened to Berkshire Hathaway.
• Discussions about the venture capital "Mount Rushmore" include influential figures and firms.
• The concept of a venture capital hall of fame is proposed, focusing on impact and legacy.

"You want to be on that with them."

Jason is expressing his aspiration to be considered alongside other legendary investors in the venture capital industry.

"So really what tiny can kind of do is come in, buy the company from the VCs, or a lot of the company from the VCs."

This quote describes Tiny's business model, where they purchase companies from venture capitalists, providing an exit strategy for the investors.

"I like the hall of Fame idea. It's kind of interesting."

Jason shows interest in the idea of establishing a venture capital hall of fame, which would honor individuals who have made significant contributions to the industry.

• Jason reflects on his career journey and the memorable moments that have shaped his life.
• He shares personal anecdotes, including the emotional experience of securing financial stability.
• The conversation touches on the evolution of podcasting and media influence.
• Jason's story highlights the importance of impact and the human element in venture capital.

"My family will never have to worry about money again because I spent my whole life worrying about money."

Jason shares a poignant moment when he realized that he had achieved financial security, reflecting on the emotional significance of this milestone.

"I think if you look at what we do as capital allocators, I think it's a very special part of the. It's a very special function in the world."

This quote captures Jason's view of the venture capital industry as a critical driver of progress and innovation, underlining the importance of supporting entrepreneurs.

"And I think Joe Rogan stole it from Howard, and I think it's now Lex stole it from Joe. Or I want to see me say, you know, inspired by."

Jason discusses the influence of Howard Stern on Joe Rogan and Lex Fridman's podcasting styles, illustrating the interconnected nature of media and influence.