jason calacanis a case study in creating resources

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Jason Calacanis: A Case Study in Creating Resources

Jason Calacanis described himself as a serial entrepreneur, angel investor, and podcaster – and someone who had come a long way from the time he had to talk his way into Fordham University. Later, when finances were tight, he talked the dean into getting the bursar to cut him a break. These early experiences with “being bold,” he believed, encouraged him to keep being bold – and creative.

This case study explores Calacanis’ path to entrepreneurship, a route that took him first into publishing, and later into angel investing, then hosting influential incubator and networking events for investors and entrepreneurs. Throughout all of these activities there was a strong creative thread – Calacanis events were not just about connecting investors and entrepreneurs, but also provided entertainment.

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Jason Calacanis: A Case Study in Creating Resources

Jason Calacanis: A Case Study in Creating Resources ^ OB104

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Product Description

Publication Date: November 11, 2019

Source: Stanford Graduate School of Business

Jason Calacanis described himself as a serial entrepreneur, angel investor, and podcaster - and someone who had come a long way from the time he had to talk his way into Fordham University. Later, when finances were tight, he talked the dean into getting the bursar to cut him a break. These early experiences with "being bold," he believed, encouraged him to keep being bold - and creative. This case study explores Calacanis' path to entrepreneurship, a route that took him first into publishing, and later into angel investing, then hosting influential incubator and networking events for investors and entrepreneurs. Throughout all of these activities there was a strong creative thread - Calacanis events were not just about connecting investors and entrepreneurs, but also provided entertainment.

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Ahir Gopaldas and Anton Siebert (2022 July August) "What You’re Getting Wrong About Customer Journeys", Harvard Business Review , 92 Linda A. Hill, Emily Tedards, and Taran Swan (2021) "Drive Innovation with Better Decision-Making", Harvard Business Review 86 Dyer, J. H., & Hatch, N. (2004). Using Supplier Networks to Learn Faster. Sloan Management Review, 45(3), 57–63 Barney, J. B. (1991). Firm resources and sustained competitive advantage. Journal of Management, 17, 99–120 Dyer, J. H., Kale, P., & Singh, H. (2004, July–August). When to ally and when to acquire. Harvard Business Review , 109–115

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The Blog of Author Tim Ferriss

Tim Ferriss's 4-Hour Workweek and Lifestyle Design Blog. Tim is an author of 5 #1 NYT/WSJ bestsellers, investor (FB, Uber, Twitter, 50+ more), and host of The Tim Ferriss Show podcast (400M+ downloads)

Jason Calacanis on Brooklyn Grit, Big Asks, Angel Investing (Uber, Calm, Robinhood, and More), The Magic of Thinking Big, and St*bbing People in the Face but Never in the Back (#635)

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“Jason would never stab you in the back. He might stab you in the face, though.” — Douglas Rushkoff

Jason Calacanis  ( @jason ) has invested in more than 300 startups in the past decade (Uber, Calm, Robinhood, and more), was Sequoia Capital’s first Scout, and is the author of the book  ANGEL . He also hosts two podcasts,   This Week in Startups   and   All-In .

Please enjoy!

Listen to the episode on Apple Podcasts , Spotify , Overcast , Podcast Addict , Pocket Casts , Castbox , Google Podcasts , Stitcher , Amazon Music ,  or on your favorite podcast platform.

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The transcript of this episode  can be found here . Transcripts of all episodes  can be found here .

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Want to hear an episode featuring another incredible entrepreneur ? Have a listen to my conversation with Automattic’s Matt Mullenweg in Antarctica , where we discussed the surreality of perpetual daylight, the “patient” Antarctican landscape, rollicking penguin imitations, the grieving process, using smartphones to regularly record loved ones, existential revelations, cloned pets, how Matt expresses anger without cursing, gratitude, and much more.

What was your favorite quote or lesson from this episode? Please let me know in the comments .

SCROLL BELOW FOR LINKS AND SHOW NOTES…

SELECTED LINKS FROM THE EPISODE

• Connect with Jason Calacanis :

Website | Twitter

• Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 by Jason Calacanis | Amazon
• This Week In Startups with Jason Calacanis and Molly Wood
• The All-In Podcast with Chamath, Jason, Sacks, and Friedberg
• Patient Capital for Building Enduring Companies | The Sequoia Capital Fund
• The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss | Amazon
• QuickTime | Apple
• The Checklist Manifesto: How to Get Things Right by Atul Gawande | Amazon
• Bay Ridge (1982) | The New York Times
• Star Wars: The Empire Strikes Back | Prime Video
• Goodfellas | Prime Video
• Silicon Alley Reporter | Wikipedia
• Local Area Network (LAN) | Wikipedia
• Grandmaster Maurice Ashley Plays NYC Trash-Talker | The Tim Ferriss Experiment
• Paper Magazine
• Barneys New York | Wikipedia
• Blender CD-ROM Magazine | Internet Archive
• Pseudo.com | Wikipedia
• ​Before the Web: Online Services of Yesteryear | ZDNET
• Sony Online | Internet Archive
• Balthazar Restaurant New York
• The Roxy (New York City) | Wikipedia
• The Chemical Brothers
• The Terminator | Prime Video
• The 10 Greatest Punk Zines of the ’80s by Michael Hardy | Medium
• 2600: The Hacker Quarterly
• Roseland Ballroom | Wikipedia
• 1,000 True Fans by Kevin Kelly | The Technium
• Sliding Doors | Prime Video
• Forrest Gump | Prime Video
• Del.icio.us | Wikipedia
• Kozmo.com | Wikipedia
• An Italian Style Icon Since 1946 | Vespa
• Bedford-Stuyvesant NYC Neighborhood Guide | Compass
• Starrett-Lehigh Building
• Ellis Island | US National Park Service
• Latham & Watkins
• A Directory of Mostly Wonderful Things | Boing Boing
• paidContent | Wikipedia
• Travel News, Airline News, and Hotel News | Skift
• Inception | Prime Video
• Weblogs, Inc. | Wikipedia
• Amazon, Meta, Twitter Layoffs: The End of Silicon Valley’s 20-Year Boom | Slate
• New FTX CEO Calls the Crypto Exchange’s Corporate Control a ‘Complete Failure’ | The New York Times
• Farewell to TUAW – And to a Whole Era of Tech Blogging | Fast Company
• Opening the Kimono Event | Tim Ferriss
• Myers–Briggs Type Indicator | Wikipedia
• Enneagram of Personality | Wikipedia
• Blade Runner | Prime Video
• “Tears in Rain” Monologue | Blade Runner
• Calacanis Calls Time on the Internet ‘Me-Toos’ | The Guardian
• The Three Musketeers by Alexandre Dumas | Amazon
• A Rare In-Person Random Show with Kevin Rose — VR Workouts, I Bonds, Excellent Movies, Recent Books, Lessons from Amy Tan, How to Shape Your Mind, and More | The Tim Ferriss Show #622
• You Might Go Through Hell for Your Post-Ozempic Body | The Cut
• Fast with Zero | Zero
• The McLaughlin Group | Wikipedia
• The McLaughlin Group (Parody) | SNL
• Mark Zuckerberg on Long-Term Strategy, Business and Parenting Principles, Personal Energy Management, Building the Metaverse, Seeking Awe, the Role of Religion, Solving Deep Technical Challenges (e.g., AR), and More | The Tim Ferriss Show #582
• The Production Board
• AMC Stock Gains as House Report Reveals New Details on Robinhood | InvestorPlace
• Athletic Greens | Tim Ferriss
• My Next Act: Democratizing Venture Capital | Launch
• The ProPublica-Vanity Fair Report on Covid’s Origins Is Explosive. Is It Reliable? | The Guardian
• Idiocracy | Prime Video
• Ow! My Balls! | Idiocracy
• Jackass: The Movie | Prime Video
• Red Scare Podcast
• Speak Freely | Signal
• Alley-Oop | Wikipedia
• Making Sense Podcast with Sam Harris
• The Reason Why Pink Floyd’s David Gilmour and Roger Waters Are Feuding | Far Out
• The Overton Window: How Politics Change | Conceptually
• Less Than Zero by Bret Easton Ellis | Amazon
• American Psycho by Bret Easton Ellis | Amazon
• The Bret Easton Ellis Podcast
• Psychedelics 101: Books, Documentaries, Podcasts, Science, and More | Tim Ferriss
• Colorado Proposition 122: Decriminalization and Regulated Access Program for Certain Psychedelic Plants and Fungi Initiative (2022) | Ballotpedia
• My Healing Journey After Childhood Abuse (Includes Extensive Resource List) | The Tim Ferriss Show #464
• Funding Cutting-Edge Scientific Research | Saisei Foundation
• [05:39] Why is this only the first time Jason’s been on the show?
• [06:37] Never underestimate the power of checklists.
• [08:56] How Jason’s young life was steeped in blood and taxes.
• [11:57] How Jason entered the world of entrepreneurship.
• [29:32] What happened when Jason got fired from his own company.
• [34:05] Orchestrating a comeback the very next day.
• [37:49] The Mercury Club that never was.
• [41:37] The origin of “Calacanis.”
• [43:01] Building a blogging empire.
• [48:36] Finding blog writers.
• [52:51] Planning events and making memories.
• [58:39] Friendship, loyalty, and collaboration with close friends.
• [1:06:00] All-In : When a solo act gets tricked into joining a band.
• [1:13:39] Memorable times All-In has gone off the rails.
• [1:21:49] With greatly followed podcasts comes great responsibility.
• [1:27:38] Keeping All-In running smoothly with four very different personalities.
• [1:34:53] Talent-wrangling techniques.
• [1:39:30] Bill Maher’s moderation style.
• [1:40:47] Friendly rapport can be contagious.
• [1:42:26] Can you see your comfort zone from the Overton window?
• [1:45:44] Transfering skills, building popularity, and co-existing with jet blockers.
• [1:52:16] What happens when you catch the car?
• [1:55:15] Psychedelic therapy and a big win in Colorado.
• [2:01:28] Jason’s billboard and parting thoughts.

MORE JASON CALACANIS QUOTES FROM THE INTERVIEW

“When I had no money and then became a millionaire, people treated me differently. All of a sudden, I got 30 more IQ points and I was two feet taller.” — Jason Calacanis

“[On All-In ], I have three partners, and all three of my partners on it have never had a boss. So you’ve literally got four of the most opinionated friends who’ve never had a boss who have four different directions they want to take it.” — Jason Calacanis

“Have great friends. Build cool shit.” — Jason Calacanis

“The system is so easy to win, and the system is set up for entrepreneurs to win in this country. Why on Earth would you cheat if it’s so easy to just have a win by just working hard?” — Jason Calacanis

“It’s important to be, I think, a really good, loyal friend. I have been burned in this regard where I’ve been more loyal to certain people and they have not been loyal to me. And it’s very frustrating for some of the people around me when they see that happen to me. And for me, I say that is that person’s chance to learn how to be a friend. They just haven’t gotten there yet.” — Jason Calacanis

“47 fucks given.” — Jason Calacanis

PEOPLE MENTIONED

• Chris Sacca
• Atul Gawande
• Jack Dorsey
• Jason’s Dad
• Leia Skywalker Organa Solo
• Josh Harris
• David Hershkovits
• Christine Muhlke
• Esther Dyson
• Kevin Kelly
• Heather Jackson
• Alan Meckler
• Douglas Rushkoff
• Charlie Rose
• Allan Houston
• Caterina Fake
• Howard Stern
• Xeni Jardin
• Marvin Minsky
• Robert Brockman
• Brian Alvey
• Peter Rojas
• Sean Bonner
• Matt Mullenweg
• George Harrison
• Paul McCartney
• John Lennon
• Nick Denton
• Evan Williams
• Dave Goldberg
• Travis Kalanick
• Chamath Palihapitiya
• John McLaughlin
• Mark Zuckerberg
• David O. Sacks
• Donald Trump
• David Friedberg
• Gwyneth Paltrow
• Brad Gerstner
• Chris Ashenden
• Vladimir Putin
• Volodymyr Zelenskyy
• Dasha Nekrasova
• Rachel Maddow
• Roger Waters
• David Gilmour
• Bret Easton Ellis
• Jade Calacanis
• Debbie Millman

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Two word impression of this episode: High energy. Loved catching the nuggets of insight scattered like tracer rounds throughout the machine gun barrage that is Jason Calacanis.

The Life and Times of Jason Calacanis: A Biography

Key Points : Timeline : Facts : Featured Video : Life Lessons Questions and Answers Resources

The Life Story of Jason Calacanis

When discussing angel investors and businesspeople, Jason Calacanis is commonly mentioned.

Calacanis got involved in several ventures, creating his own businesses or investing in just the right ones.

Calacanis is a man that saw potential in various businesses and made his fortune out of it. Even though he has a net worth in the millions, he is not as well-known as other investors.

However, his fortune has grown steadily and quickly over the past few years, showing his potential. In this article, we will talk more about Jason Calacanis and how he came to be so successful.

“When I was coming up as an entrepreneur, I had to fight for everything I got, and there was no clear roadmap of how to be successful.” ~  Jason Calacanis

Early Life and Background

Calacanis had a very good start in life, which later added to his success. Born on November 28, 1970, in Bay Ridge, New York, Calacanis was surrounded by entrepreneurs for most of his life. His parents were of Irish and Greek origin, and thanks to their encouragement and support, Calacanis obtained a good education.

He graduated in 1988 from Xaverian High School, continuing his education at Fordham University with a bachelor’s in psychology. That degree helped him understand people, and he used his ideas to set up his own business.

Growing up, he valued hard work and knowledge. As a result, he laid down the foundation for his entrepreneurial success from the moment he finished college.

However, before that, he dabbled in various ventures that would bring him some experience. During school, he began working selling books to New Yorkers door-to-door. He would also pick up the occasional job, such as selling cookies.

“Imagine being 30 years old, thinking you were a media titan, and now you are labeled a ‘scam artist.'” ~  Jason Calacanis

Early Career

After graduating from college, Calacanis entered the workforce and began his professional journey. He obtained jobs that gave him the foundation and insights necessary for his eventual triumph in the tech industry.

His initial employment was at Starwave Corporation, a technology startup. Although his tenure there was relatively short, this experience laid the groundwork for his future accomplishments.

Calacanis’s career kicked off in the 1990s when he worked as a reporter in New York, focusing primarily on the Internet sector. While at the New York Post, he identified the lack of a single website aggregating news. This observation sparked the idea for Weblogs.

Subsequently, Calacanis established Rising Tide Studio, a media company he founded to publish online and printed materials. The platform achieved considerable success, leading to Calacanis being endearingly referred to as the “yearbook editor” by the Silicon Valley community.

The Rise of Weblogs Inc. and Calacanis’s Ascend to Fame

Calacanis laid the foundation for Weblogs Inc., the company that would eventually skyrocket him to fame, on September 24, 2003. He co-founded this company alongside Brian Alvey, with financial backing from angel investor Mike Cuban.

Weblogs generated more than $2,000 per day from AdSense. The company was sold to America Online, led by Time Warner, in 2005, with Calacanis receiving over 25 million dollars. He was still the CEO for one more year, and in 2006, he resigned.

“I don’t want someone taking half a sentence or paraphrasing me… Just too much risk.” ~  Jason Calacanis

Angel Investing and Venture Capital

Aside from his journaling interest, Calacanis also began gaining more interest in venture capitalism. In 2006, after quitting Weblogs, he joined Sequoia Capital, a famous venture capital company. He was their EIA (entrepreneur in action), a position he would maintain until 2007.

During his time at Sequoia, Calacanis invested approximately $25,000 in Uber, the company founded by Travis Kalanick . Initially, the value of the company was not substantial. However, as time passed, the deal escalated to over $100 million, ultimately yielding a significant return on Calacanis’s investment.

In 2007, Jason Calacanis launched Mahalo, which means “thank you” in Hawaiian. This web directory would raise about $20 million in venture capital from numerous investors, including Elon Musk , Mark Cuban , CBS, News Corp, Sequoia Capital, and more.

The company peaked at around 15 million visitors, obtaining maximum profitability in 2011. However, the company steadily declined after the Google Panda search algorithm update that year. Eventually, Mahalo shut down its business in 2014.

Aside from Mahalo, Calacanis also laid the foundations for ThisWeekIn.com. The company temporarily shut down in 2012 but returned a few years later. It is now available to be heard as a weekly podcast.

“There’s nobody who has as big of a real-time logistics network than Uber.” ~  Jason Calacanis

Personal Life

While the exact date is unknown, Calacanis is married to Jade Li. The couple prefers to keep a low profile on their personal life, and we only know that they tied the knot somewhere around 2006-2009.

Aside from a few pictures on Instagram, we do not know much about his wife. The couple does have a daughter, as people were able to see from his Instagram posts.

Calacanis also has a brother with whom he spent most of his childhood, although little is known about him. He sparked controversy due to an association with Jeffrey Epstein after his name appeared in Epstein’s Black Book.

Calacanis denied any close connection aside from a Ted Talk conversation. He also admitted to a casual ping pong game with Epstein’s alleged accomplice, Ghislaine Maxwell.

Current and Future Endeavors

Calacanis has quite a few regular endeavors nowadays. He founded This Week in Startups, a TV show that Calacanis began co-hosting with Molly Woods. In 2023, Woods left the show, giving no specific reason. Calacanis became in charge of This Week in Startups.

Calacanis is also the founder of Inside.com, which offers thematic newsletters. The company eventually raised more than $2.6 million through its publishing. Calacanis also partnered with the NSW government, creating the Sydney Launch Festival, where startups can find investors. Impact and Legacy

Calacanis has passed some fairly impressive milestones throughout his life. Many were yearly awards, but he also received an award that would last him a lifetime. This was the Henry Bloch Award for Lifetime Achievement in 2017, where he was recognized for his accomplishments. The award would also acknowledge his ability to create opportunities for others.

Calacanis impacted various businesses that would not have been such a success without his involvement. He was among the first investors in companies such as Uber, Evernote, and Thumbtack. He saw potential in many companies, however small, and his involvement allowed them to succeed.

Moreover, Calacanis wanted to help young investors, not just the business owners. As a result, he wrote a book called “Angel: How to Invest in a Technology Startup.” This would gain him even more respect and recognition in the world of business.

“For three or four decades, we’ve been sitting here in front of this TV consuming a one-way medium that we had no control over.” ~  Jason Calacanis

With a keen eye for potential, Jason Calacanis created a fortune through hard work and smart decisions. Not only did he succeed in his own business, but he also helped numerous other businesses achieve success. Without his involvement, there is no saying what would have happened with multinational companies such as Uber. His hard work made him an example for business owners and investors alike.

• Jason Calacanis is a successful angel investor and entrepreneur who has built a fortune in millions.
• Born on November 28, 1970, in Bay Ridge, New York, Calacanis had an entrepreneurial upbringing and a strong education.
• After graduating from Fordham University with a bachelor’s in psychology, he began his career at Starwave Corporation, a technology startup.
• He made significant strides in the 1990s, working as a reporter focusing on the Internet sector, and later founded Rising Tide Studio, a media company.
• Calacanis’s fame rose when he co-founded Weblogs Inc. with Brian Alvey in 2003. The company was sold to America Online in 2005 for over 25 million dollars.
• Post-Weblogs, he joined Sequoia Capital as their EIA (entrepreneur in action) and invested approximately $25,000 in Uber, which later escalated to over $100 million.
• In 2007, Calacanis launched Mahalo, a web directory that raised about $20 million in venture capital. However, the company shut down in 2014 after the Google Panda search algorithm update.
• He founded ThisWeekIn.com, now available as a weekly podcast, and Inside.com, a thematic newsletter company.
• Calacanis is married to Jade Li, and the couple has a daughter.
• He is currently in charge of This Week in Startups, a TV show, and has partnered with the NSW government to create the Sydney Launch Festival.
• Calacanis was awarded the Henry Bloch Award for Lifetime Achievement in 2017 and has written a book titled “Angel: How to Invest in a Technology Startup.”
• Not only has he built his own successful businesses, but Calacanis has also invested in and supported various others, including Uber, Evernote, and Thumbtack.

Jason Calacanis

November 28, 1970:

Jason Calacanis is born in Bay Ridge, New York.

Calacanis graduates from Xaverian High School.

Early 1990s:

Calacanis begins his career as a reporter in New York, primarily focusing on the Internet sector. Around this time, he also starts working for Starwave Corporation, a technology startup.

Late 1990s:

Calacanis establishes Rising Tide Studio, a media company that publishes online and printed materials.

September 24, 2003:

Calacanis co-founds Weblogs Inc. with Brian Alvey.

Weblogs Inc. is sold to America Online (Time Warner), resulting in Calacanis receiving over 25 million dollars.

Calacanis resigns as CEO of Weblogs Inc. and joins Sequoia Capital as an entrepreneur in action (EIA). During this year, he also invests approximately $25,000 in Uber. He also gets married to Jade Li, the exact date is between 2006 and 2009.

Calacanis launches Mahalo, a web directory. He also leaves Sequoia Capital this year.

Mahalo, Calacanis’s company, reaches its peak profitability.

Calacanis’s ThisWeekIn.com temporarily shuts down.

Mahalo shuts down its business.

Calacanis receives the Henry Bloch Award for Lifetime Achievement.

Unknown year post-2012:

ThisWeekIn.com returns as a weekly podcast.

Calacanis becomes the sole host of This Week in Startups after co-host Molly Woods leaves the show.

Throughout his career, Calacanis also invests in various businesses, notably being among the first investors in companies such as Uber, Evernote, and Thumbtack. Additionally, he pens a book titled “Angel:

How to Invest in a Technology Startup,” aimed at assisting young investors.

Life Lessons

• Recognizing potential in various businesses: Calacanis had a knack for identifying potential in different ventures and making successful investments. This teaches us the importance of spotting opportunities and having the confidence to pursue them.
• The value of hard work and knowledge: Calacanis valued hard work and knowledge from a young age, which laid the foundation for his success. This highlights the significance of continuous learning, dedication, and putting in the necessary effort to achieve goals.
• Gaining experience through diverse ventures: Before finding his niche, Calacanis gained valuable experience through various ventures, such as selling books and cookies. This teaches us that diverse experiences can contribute to our skill set and provide insights that may be beneficial in future endeavors.
• Seizing opportunities in emerging industries: Calacanis recognized the potential of the internet and emerging technologies, which led him to establish successful companies like Weblogs Inc. and invest in startups like Uber. This emphasizes the importance of being adaptable and proactive in identifying and capitalizing on trends and emerging markets.
• The power of networking and partnerships: Calacanis formed strategic partnerships and gained financial backing from notable investors, which played a significant role in the success of his ventures. This teaches us the value of building relationships, seeking mentorship, and leveraging networks to foster growth and opportunities.
• Embracing entrepreneurship and resilience: Calacanis demonstrated the entrepreneurial spirit by founding and leading multiple businesses. Despite facing challenges and setbacks, such as the decline of Mahalo after a major algorithm update, he continued to adapt and explore new opportunities. This teaches us the importance of resilience, adaptability, and a willingness to learn from failures.
• Sharing knowledge and giving back: Calacanis wrote a book and hosted a TV show to share his experiences and insights with aspiring entrepreneurs and investors. This highlights the significance of giving back to the community, mentoring others, and sharing knowledge for the collective growth and success of the industry.
• Recognizing achievements and leaving a legacy: Calacanis received awards and recognition for his accomplishments, including the Henry Bloch Award for Lifetime Achievement. This teaches us the importance of acknowledging and celebrating milestones while striving to create a positive and lasting impact in our chosen fields.

Overall, the life story of Jason Calacanis offers valuable lessons on entrepreneurial mindset, seizing opportunities, networking, resilience, and giving back to the community. These lessons can inspire and guide individuals pursuing their own business ventures or seeking success in the world of investments.

• Jason Calacanis is commonly mentioned when discussing angel investors and businesspeople.
• Calacanis got involved in several ventures, creating his own businesses or investing in others.
• He saw potential in various businesses and made his fortune out of it.
• Calacanis has a net worth in the millions.
• His parents were of Irish and Greek origin and supported his education.
• Calacanis obtained a bachelor’s degree in psychology from Fordham University.
• Before starting his own business, he worked selling books and cookies.
• Early in his career, Calacanis worked at Starwave Corporation, a technology startup.
• He worked as a reporter in New York in the 1990s, focusing on the Internet sector.
• Calacanis identified the lack of a single website aggregating news, leading to the idea for Weblogs Inc.
• He co-founded Weblogs Inc. on September 24, 2003, with Brian Alvey.
• Weblogs Inc. was sold to America Online in 2005 for over $25 million.
• Calacanis joined Sequoia Capital as an entrepreneur in action (EIA) in 2006.
• He invested approximately $25,000 in Uber and achieved a significant return on his investment.
• Calacanis launched Mahalo, a web directory, in 2007, raising about $20 million in venture capital.
• He also founded ThisWeekIn.com and later turned it into a weekly podcast.
• Calacanis is married to Jade Li and they have a daughter.
• Calacanis received the Henry Bloch Award for Lifetime Achievement in 2017.
• He was among the first investors in companies like Uber, Evernote, and Thumbtack.
• Calacanis wrote a book called “Angel: How to Invest in a Technology Startup.”
• He founded This Week in Startups and is the founder of Inside.com.
• Calacanis partnered with the NSW government to create the Sydney Launch Festival.

Questions and Answers

The information in this post answers many of the questions about Jason Calacanis. In addition, this section provides a summary and any further information.

Sure, here are some questions based on the text provided:

• Jason Calacanis is a prominent angel investor and businessman known for his significant success in the tech industry.
• Jason Calacanis was born on November 28, 1970, in Bay Ridge, New York.
• Calacanis graduated from Fordham University with a bachelor’s degree in psychology.
• His first job after college was at Starwave Corporation, a technology startup.
• His major career breakthrough came when he co-founded Weblogs Inc., which was later sold to America Online for over 25 million dollars.
• After leaving Weblogs Inc., he joined Sequoia Capital as an Entrepreneur in Action and began to invest in startups like Uber.
• His investment in Uber, initially $25,000, escalated to over $100 million, marking his most significant success.
• Mahalo was a web directory launched by Calacanis in 2007, but it eventually shut down its business in 2014 after the Google Panda search algorithm update.
• Jason Calacanis is married to Jade Li, though the exact date is unknown; they tied the knot somewhere around 2006-2009.
• What is Jason Calacanis’s current venture?
• He is currently involved with This Week in Startups and Inside.com, and he also partnered with the NSW government to create the Sydney Launch Festival.
• What are some of Jason Calacanis’s notable accomplishments?
• Apart from his successful investments and companies, Calacanis has been awarded the Henry Bloch Award for Lifetime Achievement in 2017 and has written a book titled “Angel: How to Invest in a Technology Startup.”
• What impact has Jason Calacanis had on the tech industry?
• Calacanis’s keen eye for potential has not only brought him success but has also facilitated the success of many businesses, including companies like Uber, Evernote, and Thumbtack. His investment strategies and insight have made him a valuable figure in the business world.

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Jason Calacanis: A Case Study in Creating Resources

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Jason Calacanis described himself as a serial entrepreneur, angel investor, and podcaster - and someone who had come a long way from the time he had to talk his way into Fordham University. Later,…

• Length: 16 page(s)
• Publication Date: Nov 11, 2019
• Discipline: Organizational Behavior
• Product #: OB104-PDF-ENG

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Jason Calacanis described himself as a serial entrepreneur, angel investor, and podcaster - and someone who had come a long way from the time he had to talk his way into Fordham University. Later, when finances were tight, he talked the dean into getting the bursar to cut him a break. These early experiences with "being bold," he believed, encouraged him to keep being bold - and creative. This case study explores Calacanis' path to entrepreneurship, a route that took him first into publishing, and later into angel investing, then hosting influential incubator and networking events for investors and entrepreneurs. Throughout all of these activities there was a strong creative thread - Calacanis events were not just about connecting investors and entrepreneurs, but also provided entertainment.

Learning Objectives

Students will explore what drives entrepreneurs like Jason Calacanis, and how to chart a path to success that taps into non-traditional sources of power. With power, anything was possible.

Nov 11, 2019

Discipline:

Organizational Behavior

Geographies:

Australia, United States

Industries:

Investment management services, Publishing industry

Stanford Graduate School of Business

OB104-PDF-ENG

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Renowned “Angel” Jason Calacanis shares advice on entrepreneurship, investing

Posted in: Events

When he nailed his first major exit, Jason Calacanis sat at his computer, refreshing the screen on his Bank of America account. When the balance changed from $3,000 to $30 million, he began to cry. His wife asked what was going on, and Calacanis turned the monitor to her and said, “We don’t have to worry about money anymore.”

Calacanis told the tale of AOL’s $30 million buy of Weblogs, a blog network he created with childhood pal Brian Alvey , along with other stories of entrepreneurship and investing while visiting Montclair State on July 25. Nearly 150 people attended the event where Calacanis, a renowned serial entrepreneur and angel investor, was interviewed by David Sorin , a partner at McCarter & English . The event was presented by the Feliciano Center for Entrepreneurship , and it was Calacanis’ only appearance in New Jersey for the launch of his first book, “Angel.”

“We had an engaging, lively conversation that reveals the pivotal role of technology and entrepreneurship, politically, socially and, of course, economically,” said Sorin, whose firm sponsored the event. “Jason was generous with his time and insights, with honest and provocative responses to my questions and those of the roughly 150 attendees at Montclair State University.”

Although Calacanis has been extremely successful, resulting in financial windfalls, he wanted the audience to know he was just “a kid from Brooklyn” who if he wasn’t a rags-to-riches story, was perhaps a Toughskins-to-riches tale. Calacanis talked about his family making tough financial decisions while he grew up, and said he wrote “Angel” so others could use it as a playbook to see what’s possible. “Doing hard work and trying to be successful is a good thing,” he said.

Calacanis went to Fordham University at night, while working as a waiter and fixing laser printers. He pondered how people get rich and powerful, and gravitated to journalism, figuring the editor who puts people on the front cover of a publication is the one with the power. After launching and selling VentureReporter.net (born as Silicon Alley Reporter) and Weblogs, Calacanis moved into investing, scoring unicorns—or investments of more than $100 billion—in two of his early funding ventures, which included Uber. Calacanis’ unicorn track record is six among his first 100-150 investments, a score he compared to hitting three half-court shots during a basketball game.

For tips on how he invests, Calacanis said people assume if he invests in something it will automatically succeed, but that’s incorrect. “It’s not causation, it’s correlation,” said Calacanis.

Calacanis said he prefers to invest in someone who has a prototype, because anybody can have an idea. He wants to fund people who are dogged, hard-working, indefatigable and willing to add new skills. “If I find a founder who won’t give up, that’s the magic.”

When a 26-year-old attendee asked about the most important skill to have, Calacanis said it’s the ability to acquire new skills, and always be thinking: where can I find the hack to add this skill to my toolbox. “Have a habit of learning, just like a habit of working out,” he said.

When he hires for one of his companies, such as Inside.com, Calacanis looks for “missionaries, not mercenaries,” because the latter are just a skill-for-hire who will jump to a higher salary at any time, whereas missionaries support the mission of the company.

Calacanis spoke of advocating for more women in the startup world, especially in tech. When an attendee asked how to find diversity in a co-founder, Calacanis advised first to find someone who is passionate about the problem you are trying to solve, even if the person looks like you, but make sure they value diversity. A founder might have to wait until your third hire to find the right, diverse fit but can also be creating a culture of diversity in the startup, he said. Regarding the sexual harassment allegations that have been roiling Silicon Valley lately, Calacanis said there must be zero tolerance. “It is so front and center in our industry,” he said. “It’s career-ending at this point. … It’s one-and-done now.” He also credited that there are so many powerful women in tech who won’t tolerate such behavior any longer.

“I’m happy he touched on the diversity and gender issues,” said attendee Kavell Taylor , co-founder of Homeowners Hub . “It’s being discussed in an open forum, and was met with such warmth from the audience.”

Learn about Women Entrepreneurship Week.

Calacanis, who was generous with his time as he chatted with each attendee during the book signing, was genuinely curious to learn from the people in the audience. When a man in a wheelchair asked how there could be more startups serving people with disabilities, Calacanis answered: “I would look to you to tell me. You tell me how I can help, how entrepreneurs can help people with disabilities live full lives” and then offered to talk further with the man.

Calacanis delved into politics, leaving some to wonder if he might run for office someday – a scenario he jokes about on his “This Week in Startups ” podcast, and he owns the domain MayorJason.com (which redirects to his @Jason Twitter account). With a liberal streak, Calacanis also said that if attendees thought he was a “marauding free-market monster,” they’d be half correct.

“We have the most open meritocracy in the world. … This meritocracy draws the best people in the world,” said Calacanis, objecting to limits on which immigrants can enter the U.S. He said he decided, “I need to get more involved because if we don’t get more involved, things can go way off course.”

Calacanis talked about a coming “jobpocalypse” in which everything from baristas to lawyers will be replaced by artificial intelligence and robots. He predicted no one will be working at a McDonald’s register in three years, because customers will place orders at kiosks.

“This future is inevitable. We have to be the first ones there, as American companies,” he said.

Calacanis even opened the possibility of darker consequences, noting there could be a revival of Occupy Wall Street protests, and that wealthy people he knows are building houses off the grid in New Zealand or Montana as prep for the 1 or 2 percent chance of a class revolution. “As all these jobs will go away, there will be riots in the street,” Calacanis said, adding he believes there is an “80 percent chance we’re teetering on unrest.”

Despite the dismal prediction, Calacanis overall is an optimistic guy. He said our phones, with their constant stream of news and info, allow us to know about the worst thing happening on the planet at any given moment, yet in so many areas, life has improved.

“Actually, net-net, it’s getting better,” he said.

Whether Calacanis’ comments were sunny or serious, attendees were eager to soak up his advice and tips.

“I thought he was very insightful and entertaining. I think he captured the imagination of the crowd on how entrepreneurship is going to solve this country’s problems and move us forward,” said Peter Chmie l, a serial entrepreneur who traveled from Sayreville for the event.

Abhisek Vyas , president of Rutgers Entrepreneurial Society , said, “It was incredible because it’s not every day you get to meet a tech leader on the East Coast.”

Interview with Jason Calacanis

Jen from Jensense has a good Interview with Jason Calacanis about Weblogs Inc’s experience with Adsense. There’s lots covered but here’s Jason’s main piece of advice:

‘ Jen : What is the best piece of advice you have for a publisher brand new to AdSense? What would you have done differently when you started with AdSense, knowing what you do now. Jason : I would have run four ads per page, taken off the borders, and made the links the same color as the links on the blog. I would have also made channels for each position and blog so I could track things better.’

Most people do that allready. Is this special just because Jason would do it? I don’t think so. Darren, you posting behavior of the last few weeks seems to focus on quantity, not qualtiy.

With all due respect, Tinus, I disagree.

Keep those posts comin’ Darren. You’ve helped this blogger immensely.

I thought AdSense had a 3 ad block limit? Is he talking total ads across the different positions or within the blocks. I’m familiar with the channels, but I guess it wasn’t clear to me how to set up channels for the different positioning of ads. Is it just a matter of creating the channel name for a given position and then including it in the ads at that given position?

Tinus – I think the last few weeks I’ve written more original, long posts than I have for a long time and in the midst of it put my normal links to other sites.

I posted the tip because I saw it as Jason telling Jen what his ‘key tips’ were – not because they were unique. To be honest I didn’t see anything unique in the article but think its notable because the guy is at the head of a million dollar operation and could probably teach the rest of us a thing or two.

Having said that his tip is not really unique – I’m amazed how many bloggers do the exact opposite to what he suggests.

Jason – I think he’s talking about three ad blocks plus the ad link units across the top.

You’re spot on with what you say about channels Jason – a different channel for each position helps you track your results better.

AdSense allows three ad units PLUS one link unit per page. Google says you can have a max of three ad units per page and that link units don’t count towards that total, but you are only allowed 1 link unit per page making the largest amount possible three ad units plus one link unit = 4.

No idea what Tinus is on about or where he’d been the past week. You’ve posted a lot of content yes, but it’s been some of the best blogging I’ve ever seen Darren, or anyone else for that matter, do. His strategy blogging and apathy series of posts have both been top notch as was his recent case study which is perhaps the best post I’ve seen going around the web on blogging for a long time.

Another thumbs up here for Darrens blogging on Problogger as of late. It has been amazing, and inspiring. Keep up the great work.

Tinus, Bull.

Way to go Darren! Keep it coming!

Tinus, your reading behavior of late seems to focus on skimming, not reading.

Lately I’ve found greater success in narrowing down my ads to one well-placed adblock. I actually tripled my CTR on one blog simply by removing one of the ads (weird, huh?) – it was two small skyscrapers on either side. I think it had something to do with no focal point for clicking, but who knows.

Hopefully I can look into some better designs that cater to three adblocks better.

Jason’s idea of making an ad look less like an ad is a great one but I wonder at what point Google will begin to discourage that idea.

Google is faced with a dilemma – on the one hand it wants to increase it’s revenue by giving its affiliates more ways of using adsense and the link unit is perhaps one of the best if you know how to blend it into your page.

But at the same time, for the average surfer, those link units are almost like blind links. Sure the surfer will click them and Google will make money but once the surfer gets to the advertiser’s site he may well find that he is not where he wants to be and leaves without purchasing anything.

That means the advertiser has spent his money and not made a sale and ultimately he may feel that advertising with Google is a waste of money. So Google loses an advertiser.

This could be a balancing act that is well worth watching.

Not sure Google will discourage it Stuart – in fact the last official advice I’ve seen from Adsense actually encourages blending of ads.

That’s what I’ve heard too (blending = good).

And just a minor correction Stuart, they are not really blind links at all — they take you to a google search page that has a list of related links. It’s only when the user clicks on *those* links that anybody makes a dime, including Google. In other words, the first click on the link units is free. At least that’s how I’ve understood it.

As for the quantity versus quality debate, I’ve noticed the “quantity” theme myself lately — but after digesting it a bit (of course I was instantly hostile to it because that means more work!), I am growing to wonder if quantity is not *as important* as quality. I think the way Darren has addressed this issue has been really helpful if you open your mind to the possibilties. :)

Amended to say — I have no idea how Google makes money on link units, don’t listen to me. lol But I do know that *I* don’t make money until the user decides to click from the search results.

Thanks for that correction Taughnee – I have no problem with blending the ads at all – I may sometimes describe myself as a sensitive new-age marketer but that doesn’t mean I don’t want to make money – so I like the idea.

And I wasn’t aware that those links did not go straight through to an advertiser – I never click on links on my own site and I’ve never been inspired to click on those text links on any other site – although I almost did with one of Darren’s :)

You’re welcome. And, I guess I look at it like this — if the links are relevant, people looking for information will not be displeased and probably find them helpful. In that regard, I feel ok about the blending (and the making of the money!)

[…] tegories Posted by Jason under Journal 

After reading through the comments of a post over at ProBlogger this morning I decided to try and […]

A Practical Podcast… to Help You Build a Better Blog

A Practical Podcast…

Key Tips for Scaling Your Startup from Jason Calacanis

Anthony Stames, High Tech Industry Marketing Lead

March 25, 2019

LAUNCH founder Jason Calacanis recently sat down with NetSuite to share what he’s learned over a career in which he’s invested in more than 200 startups, including unicorns like Uber, Thumbtack, Calm.com and Robinhood. Some of his insights are surprisingly counterintuitive, others refreshingly down-to-earth. They’re all expressed in the kind of frank, practical terms that the industry has come to expect from one of its boldest voices.

In the webinar, Calacanis explained what works in the earliest stages of a startup’s existence doesn’t necessarily attract angel investors; what an angel investor sees as a sign of promise might strike a venture capitalist considering a round of Series B financing as a threat to ROI or a negligent investment altogether. Businesses in the startup phase that anticipate these challenges make the best possible case for the kind of financing that drives increased market penetration and valuation.

Here are a few takeaways:

Generate Revenue Right Off the Bat

Calacanis’ first point is the most important: startups should have one business model, and it should include revenue generation from day one. A long-term vision of success is what gets startups off the ground, but Calacanis warns against applying that same long-term thinking to a startup’s business model.

The days are gone when most startups could count on slowly developing a user base before introducing advertising revenue: companies like Uber and Airbnb incorporated revenue generation into their earliest business models and adjusted their revenue streams only as they made commensurate changes to their services and overall business models. In time, a startup may produce strong, reliable revenue streams through subscriptions, advertising and affiliate programs, but it’s unlikely to get anywhere near that point if its founders don’t concentrate on what works best right from the start.

Avoid the Feature Death March

If a startup’s business model should stay simple, so should its approach to product development. Founders are naturally filled with ideas for their flagship products, some of which can be incorporated in beta, others of which need to be held for future releases. And the ideas keep coming as a startup matures. That’s a good thing…right?

Not always. Calacanis notes that most successful startups focus on steady, incremental improvements to core services, not the introduction of flashy new features. A startup’s goal should be to produce deep products and services of narrow scope; this approach tends to set a startup apart from its competition and to cultivate customer loyalty. Developers, who know this phenomenon as Feature Creep, will be happier, too.

Adjust Your Team

It’s an awkward and often painful reality, but the right team for a startup’s bootstrapping phase isn’t the right one for an angel investor. Founding partners who feel right at home in the whack-a-mole flurry of a startup’s early days may not be content with just one role, or even effective in that capacity. And the distinction grows even more stark when rounds of VC move those founders up to managerial roles.

Successful startups are honest about the need for fewer generalists and more specialists as their companies grow. And they become adept, however uncomfortable the process may be, at helping people move on when the time is right. Even when those people helped launch the company from a dorm room.

Hear the rest of Calacanis’s points (opens in new tab) in his own distinctive voice.

Learn How NetSuite Can Streamline Your Business

NetSuite has packaged the experience gained from tens of thousands of worldwide deployments over two decades into a set of leading practices that pave a clear path to success and are proven to deliver rapid business value. With NetSuite, you go live in a predictable timeframe — smart, stepped implementations begin with sales and span the entire customer lifecycle, so there's continuity from sales to services to support.

Jason Calacanis on Startups

LIQUIDITY: A (sort of) new podcast for LPs, GPs, and angel investors.

We're rebranding our angel podcast and angel summit to "liquidity".

We are excited to announce that we're rebranding our  Angel Podcast  and our yearly  Angel Summit  event as  LIQUIDITY . 

While I started as an angel investor and Scout, I've invested out of venture funds for the past decade. Our fund sizes have increased over time, and we're a 20+ person team at  LAUNCH  (my venture firm). Our investor base started with individual investors but has grown to include more institutions. 

So, the event and podcast have expanded their mandate as well. 

The LIQUIDITY podcast will feature a rotating cast of guests, including general partners, limited partners, public market investors, and angel investors. 

You can subscribe to LIQUIDITY on  Spotify ,  Apple Podcasts , and  YouTube . 

The LIQUIDITY event will be in Napa from June 2nd to 4th. We will open registration shortly. 

PS - I'm also considering starting " the Jason Calacanis podcast " in the second half of 2024, where I talk to folks who aren't in tech. And, yes, I’m still hosting This Week in Startups and the All In podcast. :-)

OpenAI's Napster/Google Moment

The new york times got rolled by google in the 2000s, but they're not getting rolled this time around..

Today, the New York Times  sued  OpenAI and Microsoft for stealing millions of pages of their content to power the most promising technology platform since the iPhone: ChatGPT. 

The charges aren't debatable and will be quickly proven if this landmark case ever makes it to trial -- and I think this one will. 

Most language models train on an open-source project called " Common Crawl ." 

Common Crawl is like the Google search index, but it's available to everyone for free -- with some important caveats. 

The Common Crawl  terms of use  are clear: if you want to use the data they've indexed, you must go to every content owner and follow their terms of service. 

From that ToU:

" You also acknowledge and agree that all information, data, text, scripts, web pages, web sites, software, html page links, open data APIs, metadata or other materials (collectively, the  "Crawled Content " ) may be subject to separate terms of use or terms of service from the owners of such Crawled Content. "

Of course, technologists, generally speaking, have little to no respect for IP. 

I hear many peers say it's yours if you can index it, which is absurd and lacks empathy for content creators. 

This attitude started with Napster and extended to Google's approach to using other people's content 20 years ago. 

NAPSTER got smashed because the music industry is savvy and hardcore.

News sites got rolled by Google because publishers are dopey and meek. 

Google's position back then was, "If you don't want to be in the index, just tell us not to crawl you in your robot.txt file!" 

Of course, Google got so big, so fast, that it started sending massive traffic to sites like the NYTimes. 

The publishing industry was so fractured and dumb at the time that they never considered how utterly worthless Google would be if the top 500 publications refused to let them index it.

So, Google brilliantly threaded the needle on "fair use" laws by making publishers feel like "a ton of traffic for a snippet of content is a fair deal."  

Then Google gutted the publishing industry with its massive advertising platform, creating all kinds of downstream issues for society (a whole other blog post). 

The publishing industry is smaller now, battle-scarred by decades of war with technology companies. 

The NYTimes isn't the dopey publisher it was in the early 2000s. Today, they run one of the most successful subscription businesses in the world and compete in many areas outside of news.

This time, they won't get rolled; they'll fight to the death. 

And this time, they're going to win. 

OpenAI can't make the "fair use" argument that Google made because ChatGPT doesn't send traffic to publishers; it simply gives users an answer based on all the content they've liberated.

The NYTimes points this out in their suit, and it's devastating.

OpenAI will settle this suit for hundreds of millions of dollars, perhaps billions, I predict (something the two parties tried to do before the NYTimes filed). 

The suit gives many examples of OpenAI using the NYT's content, and they've caught them dead to rights. 

For example, the NYT quickly proves that OpenAI stole the Wirecutter's IP and brazenly gives results built off that IP -- but that doesn't link back, and that removes the affiliate links that pay for creating that content.

Game over for OpenAI and Microsoft with that example. 

Here’s a screenshot from the lawsuit:

Additionally, the NYTimes points out their content is behind a paywall. 

Today, I pay a couple of hundred dollars for the NYTimes. 

I am also among the millions who pay OpenAI a couple hundred dollars a year for a subscription. 

Using these services for 20+ years, my lifetime value is $6,000 each. 

I'm also a massive fan of the wirecutter and use it for my decision-making process before smashing the Amazon buy button. 

Recently, I found myself doing product searches with ChatGPT.

These two services are directly competing, and one does all the work: the New York Times.

The other steals their answers from the New York Times (OpenAI). 

Now, it’s great that OpenAI is trying to do the right thing here and settle, but let’s be honest: they’re only trying to settle this because they got caught with their hand in the cookie jar.

These are amongst the smartest individuals on the planet, and they stole this content because it would make them rich.

The discovery will show technologists trying to find the best content in the world to train their $100B franchise while they personally sell billions of dollars in shares for personal gain.

Let that sink in: the OpenAI team is reportedly selling billions of shares based on a product trained on other people’s IP.

If OpenAI can do this, well, then the rest of us can train a model on Star Wars, Marvel, Pixar, and Disney IP and make the next generation of superhero and Jedi stories!

The judges and jury in this one will make short work of OpenAI and Microsoft. OpenAI and Microsoft need to pay for the lost revenue that the NYTimes is currently experiencing--that's obvious. 

The more significant issue here is the Google v. Publisher rematch. 

The New York Times will take an open-source language model, train it on their data, and create a ChapGPT competitor--that much is clear. 

What if the NYTimes is successful with that model and they start buying more sites like Wirecutter and The Athletic? 

OpenAI and the New York Times are direct competitors; you can’t steal a direct competitors IP.

It’s that simple.

Man, maybe I need to  jaytrade  ’some NYTimes stock.

These cats at the NYTimes aren't as dumb as they used to be. 

The only question is, are they now tigers?

Would they have the audacity to compete with OpenAI?

If I were running the New York Times, I would announce a ChatGPT competitor today and raise ten billion dollars… from Google or Apple.  

best, JCal 

PS - forgive any typos. I decided to let these blog posts fly without an editor.

The greatest moment to start a company? Right Now!

Why four reasons... and you can guess at least two of them..

I lived through all four of those tech supercycles.

I learned in the first one (the PC revolution), got famous in the second (dot com), and made my fortune during the last two (web 2.0 and ZIRP).

Thanks for reading Jason Calacanis on Startups! Subscribe for free to receive new posts and support my work.

The last four tech-driven “supercycles” are worth studying:

The 1980s: The PC revolution created Microsoft ($2.7T market cap), Apple ($3T), and Dell ($48.8B).

The 1990s: The dot-com bubble created Google ($1.7T) and Yahoo.

The 2000s: The web 2.0 created YouTube, Facebook ($855B), Dropbox, Thumbtack, and Tesla.

The 2010s: The ZIRP era, which created Uber ($126B), Airbnb, DoorDash, and Coinbase.

We’re heading into what I will name “The AI Roaring 20s.”

Why The AI Roaring 20s will be the greatest time to start your company

The next supercycle is starting right now, in 2023 and 2024.

There are four reasons this will be the greatest super cycle of our lifetime:

An unlimited, cheap, and global talent pool — powered by AI tools.

Unlimited venture capital for any winning startup (defined as a startup that can get to $500,000 in revenue), with reasonable gross margins and burn.

Absurdly low operating costs, including not just talent but marketing, technology, professional services, and tools.

Jason’s Law: Every supercycle drops the cost of starting a company by 50%.

1980s In the PC era, you needed 20 people and $6M in 2023 dollars to start a company. You needed to build core technology, rack servers, get an office manager and an office, and then spend two years building your product.

1990s This dropped to 10 people and $3m in the dotcom era. You racked servers, spent a year building product, and had an office.

2000s In Web 2.0 we started companies with $1.5m and five people. Co-location providers and office sharing started, as did remote work and offshore developers. APIs and open-source software cut costs and developer cycles dramatically.

2010s In ZIRP, we saw companies start with three builders and $750,000. Github, AWS, WeWork, Fivver, Upwork, and the global workforce meant a startup could launch a product in a 12-week incubator and scale it to millions in revenue in a few years.

2020s In the roaring 20s, you can easily start your company with three founders and $375,000 — heck, even $25,000. IDEs, cloud, open source AI models, no code, low code, and a decade of remote work and workers means your product can be in customers’ hands in under 30 days.

In Summary…

Now is the greatest time to launch a startup. Uber, Spotify, Google, and Facebook aren’t hiring; most are quietly or publicly “getting fit” (aka, culling the weakest members of the herd).

You can find two founders and teach yourself to code, do growth hacking, or be a UX designer in months, so what are you waiting for?

What’s your excuse?

Who's holding you back now?

You could drive Uber or DoorDash three days a week and work on your startup with two friends on the other four days.

There are unlimited problems waiting to be solved and talent that wants to work.

I’m investing in 100 startups a year, and I’m hoping that I can be your first investor.

If this is interesting to you, please watch this video .

Let’s…. do the work

Startup productivity in the age of AI: automate, deprecate, delegate (A.D.D.)

Over the past decade, I invested in over 350 startups and watched up close as founders figured out how to do more with less.

Startups, by their nature, are resource-constrained organizations when compared to the legacy businesses they are trying to displace.

There is, of course, the rare exception of a market frenzy when startups are overfunded. I've experienced two in my lifetime: the dot-com bubble (~1998-2000) and the ZIRP bubble (~2019-2021).

Those approximate five years were fantastic times to sell overpriced equities and raise money, but they are so rare that founders should put them in the back of their minds (except as a time to consider selling some shares).

Since startups are most often resource-constrained, it's critical to look at what's taking up your time and ask the following three questions:

Can we automate this (with software)?

Can we deprecate this (because it's having little to no impact)?

Can we delegate this (to someone at a lower salary)?

While this A.D.D. framework might seem obvious as you read it, it's easy to forget (like many simple things).

How to avoid panicking your team

Now, it’s hard to implement this inside your startup because as you deploy it, folks will naturally be nervous. 

They’ll immediately ask valid questions like: 

“You’re going to automate my job?!”

“You’re going to outsource my job to a remote worker getting paid half as much as me!??!” 

“You’re going to have me stop doing the busy work that takes up half my day!??!”

“Am I getting laid off?!?!” 

The answer is “yes!” to the first three, and “your choice” for number four.

The brutal truth is that most jobs will be automated, delegated, and deprecated in the coming years thanks to AI and remote work (more on this below). 

We must embrace this moment and “move up the stack” to higher-impact work as the easy work fades away. 

The highest-level contributors in the 21st century are those who can implement this A.D.D. framework, confidently, and understanding there will ALWAYS be higher-level work. 

If you run a hotel and magically, tomorrow, a robot could deliver room service and your bags perfectly at 10% of the price, you would immediately take that win. In fact, these robots exist and are currently being deployed, by many , many , many companies. 

So, you take the win and redeploy the bellhop and room service staff (if willing to level up) to higher-level work that improves the guest experience. 

If the guest experience gets perfected and you need fewer people to run the hotel, you should…. wait for it…. open another hotel. Or lower the prices at your current hotel. Or increase your profitability and raise the remaining employees' salaries. 

That’s where society is headed, fewer people accomplishing more and doing more meaningful work.

This evolution has been happening for some time now, but with AI it’s going into hyperdrive. 

Here's how you implement the A.D.D. framework:

a. Every week, ask your team to do an S.O.W. and E.O.W .: a start-of-the-week report and an end-of-the-week report.

b. After three months, review the significant items folks accomplished each week and ask them which items they think have the highest and lowest impact on the business. People will be candid with you.

c. Automate: sit with whoever the most tech-savvy folks in your company are and figure out how to automate the most critical tasks where possible. At my investment firm, LAUNCH, we have a half dozen folks who know how to use Notion, CODA, Zapier, Airtable, and Slack to build “mini-apps” that automate everything we do. Hands down, these are our most valuable team members. 

d. Deprecate: When faced with a list of tasks that can’t quickly and easily be automated, ask yourself, as the founder, if this task is essential or optional. As a founder, you probably asked folks to do things last year that are no longer essential this yearl, but your loyal team members are doing them as if they are. 

Your bad. Be ruthless in deprecating these items. If you're wrong, you can always add the items back.

e. Delegate: After you automate and deprecate, you'll be left with a bunch of important tasks that can't be automated and that you need to do. At this point, look at the hourly salary of the person doing them. Times that salary by 1.2x (for benefits and equipment) and then divide that number by 2,000 (the number of hours the average person works a year). 

If a $100,000 employee updates a database with contact information and processes invoices for 10 hours a week, that is costing you $60 an hour ($120,000 / 2,000). A work-from-home executive in the USA would cost ~$25. In Canada, it would cost ~$15 USD. In Manila, it would be $5 an hour (and you would have a line out the door of folks who want that job).  

The average $100,000 employee in America who implements the A.D.D. system will automate 20% of their job, deprecate 20%, and delegate 20%, in my experience. 

This means every year, a high-functioning team should be able to free up ~50% of their cost/work on average (depending on how much you save when you delegate that 20%).

Why is this important now?  

While these steps seem apparent, three things have made this framework critical: 

Startup funding has collapsed by 75%. 

Remote work has made all of us exceptional at managing and delegating work. Managing an American, Canadian, Argentinian, or Phillipino team member is the exact same on SLACK and Zoom.

Most importantly, ChatGPT, Bard, Claud, and countless emerging AI tools are making the automation of work accelerate at an absurd pace. 

The great irony, I’ve learned, is that the remote workers from emerging markets are the ones embracing ChatGPT the most. It’s obvious why when you think about it. 

These remote workers are typically working freelance for a dozen customers who only care about output. They’re very hungry, and they are absurdly customer-focused. They know that the faster and happier they make a customer, the more money they can make. 

In conclusion

I’ve been working with our portfolio companies and our teams on this process for over a year, and it’s having dramatic results. This is a 1.0 framework, so please take it, remix it, and report your results to me. 

We all want to do more meaningful work and we will always find new ways to be helpful to society. 

Embrace the pace! 

Speed wins.

My email is [email protected] for life.

Best, JCal 

PS - I’m going to start doing weekly posts here on Substack, to my x.com/jason account, and Linkedin. I am also planning on doing a paid subscription of some type to hire a full-time editor to work with me on these posts. 

Will include some sort of subscriber Q&A and benefits as well (hit reply and tell me what you want). If you want to pre-pledge, you can do so at calacanis.substack.com. Which will give me some signal as to people’s interest.

All In Ep 148 & AI Demos on TWIST

The latest All In episode is up:

Also, many of you have asked me about the talks from the All In Summit. Instead of flooding the podcast feeds, we posted them to YouTube and X/Twitter .

On my other podcast, This Week in Startups , we’re covering all the progress in AI on Monday’s show with my pal Sunny.

All the best, JCal

twitter.com/jason

email: [email protected] for life

If you know of any early-stage startups looking for investment, please introduce me or send them to launch.co/apply (which will get them a meeting with my team).

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Jason Calacanis: A Case Study in Creating Resources

Pfeffer, Jeffrey

Reference : SGSB-OB104-E

Year : 2019

Number of pages : 16

Geographic Setting : USA

Publication Date : Nov 11, 2019

Source : Stanford Graduate School of Business (USA)

Type of Document : Case

Industry Setting : publishing; investing

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Jason Calacanis: A Case Study in Creating Resources

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Jeffrey Pfeffer Stanford Graduate School of Business ( OB104-PDF-ENG ) November 11, 2019

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1 hr 16 min

How To Pick Startup Winners With Jason Calacanis Where It Happens

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Are you ready to start angel investing? In today's episode, we share the secret to creating long-term wealth, explain how to become a “sophisticated” investor, and discuss the downsides of crypto. Hosts Sahil Bloom and Greg Isenberg are joined by guest Jason Calacanis, the creator behind the All-In Podcast, a serial angel investor, and a leading entrepreneurial author. Jason explains the entrance costs to investing, shares why people need to validate their research, and then everyone places their bets on this week's “hot” stocks. ►► Want more community? Learn more here: http://trwih.com SPECIAL THANKS TO OUR SPONSORS ►► This episode is brought to you by Wealthfront, a saving and investing app that can help you earn more on your money and build wealth for your future. The Wealthfront Cash Account grows your savings at 1.40% APY, and offers unlimited, fee-free transfers to your external accounts — plus, a ton of other features that help you optimize your cash. So, if your money is earning less anywhere else, now might be a good time to make a move. Wealthfront is offering Where it Happens listeners a free $50 bonus with a $500 initial deposit to a new Cash Account. Go to wealthfront.com/Happens to claim your $50 and start growing your savings. Cash account is offered by Wealthfront Brokerage LLC, Member of FINRA/SIPC. Wealthfront Brokerage is not a bank. We convey funds to partner banks who accept and maintain deposits, provide the interest rate, and provide FDIC insurance. Rate is subject to change. Investment management and advisory services--which are not FDIC insured--are provided by Wealthfront Advisers LLC (“Wealthfront Advisers”), an SEC-registered investment adviser. ►► Did you know that one of the top reasons startups fail is bad hiring decisions? People can be unpredictable. And developers can be unpredicted, as well. Let Lemon.io take care of hiring your software engineers. They have a hand-picked roster of engineers from Europe, and we recommend them to companies we work with. Sign up at lemon.io/room for 15% off for the first 4 weeks. FROM THIS EPISODE Jason Calacanis https://twitter.com/Jason Sahil Bloom: https://twitter.com/SahilBloom Greg Isenberg: https://twitter.com/gregisenberg Production & Marketing Team: https://penname.co/ CONNECT WITH US Newsletter: https://trwih.com Twitter: https://twitter.com/_trwih Instagram: https://www.instagram.com/_trwih TikTok: https://www.tiktok.com/@_trwih Spotify: https://open.spotify.com/show/6aB0v6amo3a8hgTCjlTlvh Apple: https://podcasts.apple.com/us/podcast/where-it-happens/id1593424985 SHOW NOTES 02:11 The Original Crypto Investor & “Sophisticated Investors” 06:28 Crypto Tokens: Public Market or Scheme 12:02 Where is Web 3.0 in Five Years? 15:35 Breaking Ownership with Web 3.0 17:55 The Downside of crypto 21:19 Default Centralized in a Crisis 23:39 Free to Mint NFTs 26:12 The Entrance Costs to Investing 30:05 Being Honest on Upsides AND Downsides 35:52 Validate Your Crypto “Research” 38:16 #JTrading & Betting on Disney 40:36 Super Forecasting and Creating Processes 46:06 SNAP: Buy or Sell? 49:19 BuzzFeed: Buy or Sell? 51:34 The Secret to a $10M Net Worth: Index Funds 55:26 Behind the Scenes with the All-In Podcast 1:02:44 What Motivates Jason? 1:05:08 Manufacturing Peak Experiences

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