From the dot.com boom to his top podcast This Week in Startups, Jason has been an observer of what it takes to succeed in Silicon Valley.
He has invested in over 300 companies, with several of them being valued at over 1 billion dollars.
In this talk based on his career as an angel investor, Jason will share the cold hard lessons of Silicon Valley: what works, what doesn’t, when to dive in, and when to cut your losses.
In this fireside chat with Jason Calacanis, audiences will dive deep into the world of Silicon Valley, tech companies, and angel investing.
Jason shares stories about his journey from tech company creator to tech company angel investor. Learn the secrets of Silicon Valley and the process Jason uses to evaluate tech companies and their founders when investing.
Jason Calacanis is a prominent figure in the technology and startup ecosystem, renowned for his success as an angel investor, entrepreneur, and thought leader in the tech industry. His influence as a top business speaker and tech visionary has made a substantial impact on the world of startups and venture capital.
Jason Calacanis is a top business speaker and tech thought leader known as the “greatest angel investor.” His book Angel: How to Invest in Technology Startups: Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 was an Audible bestseller. And his podcast This Week in Startups was featured in the Fortune article “The Ultimate Guide to the Best Business Podcasts.”
Proclaimed “arguably the world’s greatest angel investor” by The Twenty Minute VC, Calacanis has invested in over 300 early-stage startups. Several have achieved billion-dollar evaluations, such as Uber, Robinhood, Trello, and Calm (the meditation app).
Jason got his start in angel investing with the top-tier, venture-capital firm Sequoia Capital. While working as a scout, Jason’s invested $25,000 in Travis Kalanick’s company, Uber, which is now worth around $100 million.
Jason Calacanis is perhaps best known for co-founding Weblogs, Inc. in 2003, a company that would later become a major player in the blogging and online media landscape. Weblogs, Inc. was one of the first companies to create a network of professionally edited blogs covering a wide range of topics. The company’s success and eventual acquisition by AOL in 2005 marked a significant milestone in the evolution of digital media.
Calacanis is often referred to as the “greatest angel investor” due to his early investments in a number of now-iconic startups. Some of his notable investments include:
Jason Calacanis knack for identifying and supporting successful startups has earned him a reputation as an astute angel investor. His investments have not only been financially rewarding but have also contributed to the growth of innovative companies that have reshaped industries.
In addition to his accomplishments as an entrepreneur and investor, Jason Calacanis has established himself as a sought-after business speaker and tech thought leader. He frequently shares his insights and expertise at conferences, webinars, and podcasts. His thought leadership covers a wide range of topics, including entrepreneurship, angel investing, the tech industry, and startup strategies.
Jason Calacanis is known for his candid and sometimes controversial style. He doesn’t shy away from expressing strong opinions and engaging in debates, making him a polarizing figure in the tech and business communities. His willingness to challenge conventional wisdom and provoke discussion has contributed to his influence as a thought leader.
Jason Calacanis’s journey from a young entrepreneur to a top business speaker and angel investor underscores the dynamic nature of the tech industry. His contributions to the world of startups, digital media, and angel investing have left an indelible mark. Calacanis continues to be a prominent voice in the tech and business world, offering insights, investing in promising startups, and sharing his experiences with audiences eager to learn from one of the industry’s most influential figures.
Contact us at Speakers Inc and follow us on Twitter
No reviews available for this post.
Speaker fees can vary depending on factors such as expertise, demand, and event specifics. While some speakers may charge a flat fee for their services, others may have hourly rates. It’s best to discuss fee structures directly with the speaker or their representative to understand the pricing model.
Keynote speeches typically range from 30 to 90 minutes, with the duration determined by the speaker’s expertise, the event’s agenda, and audience preferences. Keynote speeches often include a combination of inspirational stories, practical insights, and actionable advice tailored to the event’s theme or objectives.
The scale of the event and audience size can indeed impact a speaker’s fee. Larger events with a broader reach or higher attendance may command higher fees due to increased exposure and demand. Conversely, smaller events or niche audiences may offer opportunities for more flexible pricing arrangements.
Travel expenses such as transportation, accommodation, and meals are typically negotiated separately from the speaker’s fee. These costs vary depending on the speaker’s location, travel distance, and event duration. It’s important to clarify travel arrangements and expenses during the booking process to avoid misunderstandings.
Many speakers require a deposit to secure a booking, with the remaining balance due closer to the event date. Deposits are often non-refundable and serve as a commitment from both parties. It’s advisable to discuss deposit requirements and payment terms with the speaker or their representative when finalizing the booking.
Ready to find the perfect speaker for your event? Use our advanced search feature or contact us to get started today!
Greg Schwem is more than a comedian; Greg Schwem is a motivational corporate comedian. And the corporate world has taken note. Greg’s take on the 21st century workplace and work/life balance has landed him on SIRIUS Radio, Comedy Central and the pages of Exceptional People Magazine. More than just a business humorist, Greg is also an author, nationally syndicated […]
Long before artificial intelligence became the powerhouse of modern technology, Yejin Choi was already diving into its most complex and overlooked challenges. As the Dieter Schwarz Foundation HAI Professor, a Professor of Computer Science, and a Senior Fellow at Stanford HAI, she continues to shape the future of AI research with a sharp focus on […]
Kevin Daley stands as a testament to the power of resilience, leadership, and unwavering positivity. As an accomplished speaker and the award-winning author of I Never Stopped Smiling, Daley’s journey from the hardwood courts of the Harlem Globetrotters to the international stage is nothing short of remarkable. Kevin Daley | Sporting Legend Daley’s ascent to […]
Dr. Paula Stone Williams is an advocate and renowned globally for her tireless work in championing gender equity, LGBTQ rights, and religious tolerance. As a transgender woman, Paula brings a unique and invaluable perspective to her endeavors, shedding light on the profound disparities inherent in societal structures. A dynamic keynote speaker, Paula’s story of transition […]
After years of conversations and consultations, research and interviews regarding diversity & inclusion, Risha Grant has learnt that companies don’t have diversity problems; they have people problems. For too long, diversity has been blamed for loss of productivity, discrimination and a litany of other workplace faux pas, but diversity has never been the issue. It can’t […]
Erin Stafford is the Head of Marketing for the largest healthcare staffing company in the United States, Erin’s leadership was instrumental in the company’s phenomenal growth, overseeing the largest deployment of healthcare personnel in history. With a remarkable track record that includes growing the company by nine fold within just two years, Erin has established […]
W Kamau Bell is a sociopolitical comedian who is the host and executive producer of the Emmy Award winning CNN docu-series United Shades of America with W. Kamau Bell. On June 26th he makes his Netflix debut with a new stand-up comedy special, Private School Negro. Kamau has a book with the easy-to-remember title The Awkward […]
Gregory Robinson is a distinguished leader in aerospace and science, celebrated for his pivotal role as the former director of the $10 billion James Webb Space Telescope (Webb). With an illustrious 33-year career at NASA, he has been instrumental in shaping some of the most groundbreaking space exploration projects of our time. His expertise in […]
No results available
These remain the property of its owner and are not affiliated with or endorsed by Speakers Inc.
All talent fees exclude VAT, travel and accommodation where required.
Our Mission:
© All rights reserved 2026. Designed using Voxel