Jason Calacanis The World's Greatest Angel Investor

In episode 41 of the 20 minutes VC, host Harry Stebbings interviews renowned angel investor Jason Calacanis, discussing the future of podcasting, the intricacies of angel investing, and Jason's personal investment ethos. Calacanis, with notable investments like Uber and Thumbtack, shares insights from his extensive experience, including the importance of passion in entrepreneurs, the significance of third-time founders, and his ambition to become the greatest angel investor. He emphasizes the value of personal relationships in business and candidly critiques the startup ecosystem, from inflated valuations to the shortcomings of bitcoin startups. Calacanis also touches on the transformative potential of emerging technologies like drones, 3D printing, and virtual reality, while advocating for practical education over expensive college degrees.

• Harry Stebbings introduces Jason Calacanis as one of the greatest angel investors with over 60 investments.
• Jason has invested in companies like Uber and Thumbtack.
• He is also the host of "This Week in Startups" and founder of Launch and the Launch Festival.
• Harry credits the growth of the 20 minutes VC to the support from Product Hunt and guests like Jason.
• Hiring Screen assisted Harry in finding his own assistant, similar to how Jason has Jackie for his show.

You are listening to episode 41 of the 20 minutes VC with your host Harry Stebings. Now today is an incredibly special day at the 20 minutes VC as we welcome the incredible, the legendary Jason Calicanis.

This quote introduces the episode and the guest, Jason Calacanis, highlighting his status in the venture capital world.

• Jason discusses the difficulty of building a successful podcast network.
• He notes that it takes a passionate individual willing to work for free for years before a podcast becomes successful.
• Revenue generation in podcasting can take several years, with established individuals gaining attention faster.
• "This Week in Startups" makes significant revenue from advertisements, indicating the potential profitability of podcasting.

Well, here's the thing. I started this podcasting company this weekend with my friend Kevin Pollock like six years ago, and then we gave up after about three or four years on trying to get other people to do it because it seemed like the only way it worked is if some crazy maniac with a really good reputation and network was willing to work for free for a couple of years, and then the podcast would magically work in year four or five...

Jason reflects on his past experience with podcasting and the realization that success in the medium often requires long-term commitment and passion.

• Jason's podcast, "This Week in Startups," has 150,000 downloads per episode.
• He discusses the importance of super distribution across platforms like YouTube and podcasting apps.
• Stitcher, TuneIn, Overcast, and the Apple iTunes podcasting app are mentioned as popular podcasting platforms.
• The concept of "archive power" is mentioned, indicating the long-term value of podcast content.

150,000 downloads per episode.

This quote provides a metric for the success of Jason's podcast, showcasing its reach and audience size.

• Jason shares his long-term relationship with Uber's founder, Travis Kalanick.
• He discusses the importance of investing in people and their passion.
• Jason emphasizes the value of investing in founders who are on their third or fourth venture.
• He regrets passing on early investments in Twitter and Zynga but learned to trust his instinct in people.

Well, I'm obviously delighted with how the company's turned out, but it's not unexpected that this would become an important company because the founder, Travis, who I've known for 15 years...

Jason expresses his satisfaction with Uber's success and reflects on his longstanding relationship with its founder, emphasizing the importance of investing in people you believe in.

• Jason describes his ability to read people and identify those who genuinely care about their ideas.
• He mentions that he can dismiss seven out of ten founders who lack passion.
• The remaining three are more likely to succeed and are worth investing in.
• Jason talks about his "eye of the tiger" concept, which is about spotting genuine passion in entrepreneurs.

You know what, it's very weird. I could try to explain it to you, but I would seem, like, really pretentious. But the truth is, when I'm talking to somebody, I almost feel like I see past their eyeballs and I see into their brain and their soul and I see if they actually give a shit.

Jason explains his intuitive process for evaluating the passion and dedication of entrepreneurs, which guides his investment decisions.

• Jason aspires to be the best angel investor in history.
• He discusses his competitive nature and desire to outperform his peers.
• He has a $10 million angel fund and plans to invest in 100 companies.
• Jason values investing in people and their passion, which he believes is the key to successful angel investing.

I want to be the best angel investor in the history of angel investing. And I think if you asked any entrepreneur, which angel investor would they want to have on their team? I think most people, I don't know where you would put me, but in terms of desirability, I'm definitely in the top ten.

Jason expresses his ambition to be recognized as one of the top angel investors, emphasizing the importance of being a desirable partner for entrepreneurs.

• Jason ranks himself among the top angel investors, alongside Chris Sacca and Tim Ferriss.
• He acknowledges the achievements of other investors like Gil Penchina.
• Jason reflects on Chris Sacca's status, considering him a legend in the field.
• He discusses the importance of winning as a team and enjoying success with his peers.

I would absolutely agree with Chris.

This quote shows Jason's agreement with the host's suggestion of Chris Sacca's high ranking among angel investors, indicating mutual respect in the industry.

• Jason talks about the importance of maturity in balancing different aspects of life.
• He mentions the drive of young people and the evolution of motivation with age.
• Jason discusses the two scorecards of life: external achievements and personal relationships.
• He stresses the importance of being a good family member, friend, and professional.

You have maturity. I mean, there's a lot of maturity that occurs, I think, when you're young...

Jason reflects on the growth and maturity required to maintain a balance between personal and professional success.

• Jason admits to being competitive and desiring to be the best in his field.
• He discusses the different motivations for success and the power of competitive motivation.
• Jason emphasizes the joy of winning with his team and peers.
• He shares his approach to competition and collaboration in angel investing.

Winning at all costs and winning alone sucks. Winning on a team, well, that's magical.

This quote encapsulates Jason's perspective on the value of teamwork and shared success in the competitive world of angel investing.## Self-Restraint and Communication

• Jason Calacanis speaks about how he has learned to communicate his thoughts more diplomatically over time.
• He may discuss matters privately rather than publicly to maintain professionalism.
• Jason emphasizes the importance of standing up for oneself while navigating professional relationships.

"Not really. I just say it a little differently now."

Jason indicates that he still speaks his mind, but has adjusted the manner in which he conveys his messages for better outcomes.

"You know what I feel like if you don't stand up for yourself, you know, and you don't make a point of telling people like, hey, this is how this needs to work. Well, then people are going to treat you a certain way."

Jason underscores the necessity of self-advocacy in business to ensure that others respect one's boundaries and expectations.

• Jason describes his role in the venture capital ecosystem as akin to a point guard in basketball, identifying promising startups and passing them on to other investors who can help them scale.
• He mentions specific interactions with venture capitalists like Chamath Palihapitiya and Bill Gurley, highlighting successful collaborations.
• Jason also expresses frustration with a high-profile VC who did not meet with founders he referred, which he sees as unprofessional and disrespectful.

"I have a company that I think is going to be the fifth unicorn in my portfolio."

Jason is optimistic about a potential investment becoming highly successful and contributes this to his strategic collaborations in the venture capital space.

"That is not fucking cool. These are entrepreneurs who are busting their ass."

Jason is passionate about the effort entrepreneurs put into their businesses and expects venture capitalists to respect and acknowledge that effort by taking meetings seriously.

• Jason details an email he wrote to a VC who failed to meet with founders he referred, expressing his disappointment and the negative implications of their actions.
• He believes in holding professional contacts accountable and making it clear how he expects business to be conducted.
• Jason's approach to communication is direct and unapologetic, prioritizing the interests of the founders he supports.

"Subject line, deal flow, person, famous person number one. Famous person number two. Famous person number three."

This is the beginning of the email Jason sent, illustrating his direct approach to addressing his concerns with the VC.

"So anyway, I felt you should know why I stopped sending you startups."

Jason explains the reason for his email, which is to inform the VC about the consequences of their actions and the impact on their professional relationship.

• Jason emphasizes the importance of choosing individual partners over firms when raising money.
• He lists several investors he respects and would choose to work with, based on their track record and personal relationships.
• Jason plans to host an event where he will interview top investors, reflecting his continued engagement with the venture capital community.

"I like partners, not firms."

Jason prefers to work with individuals whose abilities and work ethic he trusts, rather than being influenced by the reputation of the firms they represent.

"I'm going to make my list of the top 20 investors and you'll see actually who I think are the top 20."

Jason reveals his intention to publicly acknowledge the investors he considers the best in the industry, which will be featured in his upcoming event.

• Jason discusses the variety of content he produces for his podcast, catering to different audience interests.
• He aims to provide tactical advice for founders, deep-dive interviews, and news roundtables, showing a commitment to a diverse content strategy.
• Jason also expresses a desire to improve his interviewing skills and eventually expand his podcasting topics beyond technology.

"I'm trying to help them, and I send you somebody."

Jason's podcasting efforts are an extension of his desire to support entrepreneurs and contribute to the startup ecosystem.

"I want to be the best interviewer in the technology business."

Jason sets a personal goal to excel in his interviewing skills, demonstrating his ambition and dedication to his craft.

• Jason outlines his future goals for his conference and media presence, aiming to expand the audience and influence of his events.
• He hints at potential new ventures, including a non-technical show and possibly a television or radio program.
• Jason's long-term vision includes scaling his conference and diversifying his professional activities.

"I always got a plan, man. That's what I do."

Jason conveys his forward-thinking mindset and proactive approach to business and media.

"So when I retire I think that will be the time I'll do it."

Jason acknowledges that some of his ambitions may have to wait until later in his career, indicating a strategic approach to timing and resource allocation.## Podcast and Media Strategy

• Jason Calacanis discusses his approach to podcasting and media, emphasizing authenticity and avoiding overproduction.
• He aims to grow his media brands, Launch and Inside, to be significantly larger.

"And so I think if we can get launched to that level, if we can get inside to maybe being three or four times bigger, that would be great."

The quote highlights Jason's ambition to expand his media businesses and his focus on growth.

• Jason distinguishes between the interviews he enjoys and those that the audience prefers.
• Gary Vaynerchuk is mentioned as a popular guest among the audience.
• He reflects on memorable interviews with various entrepreneurs and gets "lost in the moment" during these conversations.

"Well, there's what I enjoy and there's what the audience enjoys. So the audience has been pretty clear that they really love the conversations with Gary Vaynerchuk..."

This quote shows Jason's awareness of his audience's preferences and how they might differ from his own.

• Jason expresses gratitude and surprise at the recognition he receives from prominent figures.
• He shares his feelings about his unexpected level of success and contemplates his future.

"I mean, I'm so thrilled. Right? Mean, if it's not coming across in my social media and the show and just my general demeanor at the events and stuff like that, I never expected to be here."

Jason is sharing his genuine astonishment at his achievements and his humble perspective on his success.

• Jason has a rule against displaying achievements, fearing complacency and living in the past.
• He prefers to focus on the present and the work that needs to be done.

"Once I start putting that shit on the wall, I'm going to start living in the past, and I'm actually going to think, like, I'm successful. I don't want to think I'm successful. I want to think that I have to get up today and I got to do work."

Jason explains his philosophy on success and his proactive approach to avoid resting on his laurels.

• Jason expresses pride in his team's hard work and positive attitude despite competitive challenges.
• He values staying positive and learning from what works.

"And they're just crushing it, and they're working really hard. And not everything's going right, but some things are going right. And I'm like, you guys are really staying positive and studying what's working. So proud of you guys."

This quote underscores Jason's leadership style, focusing on motivation and appreciation for his team's efforts.

• Jason recounts his early work experiences, including menial jobs that helped him pay his way through school.
• He emphasizes the hard work and determination it took to get through those times.

"So I worked three jobs. I was fixing laser printers during the day, I was a waiter on the weekends, and sometimes I would be what's called a barback."

Jason reflects on his past to illustrate his work ethic and the challenges he overcame in his youth.

• Jason shares a personal story about his father's business failure, which had a profound impact on him.
• This experience instilled in him a determination to avoid similar failures and contributed to his drive for success.

"I think when my dad's business failed, when his bar got taken by the feds because he didn't pay his taxes, and I watched him fail when I was 17, and I just thought to myself, my God, I'm never going to want to fail like that."

The quote reveals a pivotal moment in Jason's life that shaped his future ambitions and fear of failure.

• Jason discusses the challenges he faced during the Internet bubble burst and 9/11.
• He talks about developing resilience and maintaining perspective through difficult times.

"If you survive enough shit in your life, you start to become a little bit fearless about it."

This quote highlights Jason's philosophy on adversity and the strength that comes from overcoming significant challenges.

• Jason's investment strategy focuses on people and relationships rather than just business prospects.
• He values friendship and trust in his business dealings and invests in people he believes in, even if they are not yet successful.

"My job is to be the guy who believes in you before when nobody else does. And that's what I center my career around, is how do I believe when nobody else does?"

Jason articulates his core investment principle of supporting entrepreneurs with potential, regardless of their current success.

• Jason discusses his ownership of the first Tesla Model S and his refusal to sell it, indicating a personal attachment to the vehicle.
• He also mentions recent investments in various startups, highlighting his interest in diverse fields.

"I got offered twice what I paid for it with 20,000 miles on it. Yes. Somebody offered me $250,000 for it."

The quote illustrates Jason's personal value placed on the Tesla Model S and his lack of interest in selling it for a profit.

• Jason is bullish on the future of drones, 3D printing, virtual reality, and machine learning.
• He believes these technologies are converging and building off each other, propelled by advancements in smartphones.

"Drones, 3d printing and virtual reality and machine learning and the on demand economy, these sort of trends are all starting to merge and sort of build off of each other and really build off the back of smartphones."

Jason shares his insights on the interconnectivity of emerging technologies and their potential to disrupt various sectors.## Virtual Reality's Potential in Various Industries

• Virtual reality (VR) has significant potential in video games, adult entertainment, and education.
• VR could revolutionize how practical skills are learned and applied, such as in medical training for surgeries.
• Access to VR training could identify talented individuals worldwide, regardless of formal education.

"It might turn out that some kid from Pakistan who has incredible dexterity and concentration can do the best heart surgery in the world and has no training other than she or he hung out in the simulator all day long because the course was free on the web."

This quote emphasizes the democratizing potential of VR in education, allowing individuals to gain advanced skills without traditional education paths.

• College degrees are not seen as necessary by Jason Calacanis.
• The cost of college education is considered to be a rip-off, particularly when it leads to significant debt.
• Alternatives to college, such as investing in starting a business, may provide more value and practical experience.

"College is the biggest rip off on the planet."

This quote reflects Jason's strong stance against the value proposition of college education, highlighting the excessive costs and potential debt burden.

• Jason Calacanis wrote about bitcoin early on but regrets not investing when it was less expensive.
• The future of bitcoin is uncertain; it could either fail or succeed like early internet technologies.
• The blockchain technology underlying bitcoin is interesting, but the applications are currently limited.
• There is criticism of the execution by founders in the bitcoin space, suggesting a lack of mainstream applications.

"I think bitcoin has an equal chance of going to zero as it does to $1,000 again."

This quote captures the unpredictable nature of bitcoin's future value and the comparison to early internet technologies that didn't last.

• Jason believes that valuations in the bitcoin market and generally in the startup ecosystem are inflated.
• He advocates for value-added investing with a focus on due diligence and a close relationship with entrepreneurs.
• Jason criticizes the high valuation expectations of startups, especially at Y Combinator's demo days.
• He suggests that the quality of investment would improve if investors took on fewer deals but with more focus.

"Everything's inflated."

This succinct quote summarizes Jason's view on the current state of market valuations, implying a bubble-like situation.

• Jason runs his own accelerator, preferring a hands-on approach with a small number of companies.
• He contrasts his model with larger accelerators like Y Combinator and 500 Startups, emphasizing personalized attention.
• Jason advises startups to research and understand their investors before pitching.
• He also shares his admiration for Elon Musk's fearlessness and risk-taking approach.

"I would rather just accept people to mine and work with them. And so in my accelerator, we only have seven companies."

This quote explains Jason's preference for a more intimate and involved accelerator model, offering more personalized guidance.

• Jason prefers email as the most efficient way for founders to connect with him.
• Founders should engage with the investor's content, such as blogs and podcasts, to understand how to effectively pitch.
• Doing thorough research on potential investors is crucial for founders seeking investment.

"I've written, they should read my blog and they should watch the podcast and they should come to the events."

This advice highlights the importance of founders familiarizing themselves with an investor's work and perspective before making contact.

• Jason regards Elon Musk as a gold standard for entrepreneurs.
• He has learned a lot from Musk, especially about underestimating downside risks.
• Musk's fearlessness is seen as almost superhuman, and while Jason tries to adopt a similar attitude, he acknowledges it's a rare trait.

"Most people overestimate the downside risk, and that always stuck with me."

This quote from Elon Musk, as relayed by Jason, encapsulates the mindset of embracing risk for substantial success.