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!

Lisa-Marie Burnside has a passion for life, something that is apparent the moment you meet her. An avid fitness enthusiast and former marathon runner, she found herself on the hunt for something that would allow more self-expression and creativity, while still getting a great workout. Aerial dance was the answer. With over 10 years of […]

Kym Priess is an emcee, comedian, actor, songwriter, and acting coach, Kym embodies the essence of entertainment. With her innate talent, she brings joy, creativity, and humor to every event she hosts. Are you in search of an event emcee who can captivate audiences, infuse humor, and ensure an unforgettable experience? Kym Priess | Event […]

Troy Hazard stands as a seasoned navigator, having weathered storms of both failure and triumph. With a track record spanning over two decades, he epitomizes resilience and entrepreneurial acumen, having founded and cultivated twelve ventures. From the brink of financial ruin to the pinnacles of success, Hazard’s journey embodies the essence of strategic risk-taking and […]

Rohit Talwar is a global futurist, award-winning and thought-provoking speaker, strategic advisor, author, entrepreneur, and the CEO of Fast Future. He delivers keynote speeches, executive education, consultancy, research, and future-focused leadership mentoring to clients internationally. He works with major corporations, governments, professional services, investors, associations, business schools, and NGOs to help them anticipate, prepare for […]

Kerri Strug vaulted into Olympic history with her courageous performance during the 1996 Olympic Games in Atlanta. With the world watching, she executed a near-flawless vault on an injured ankle, securing the first-ever team gold medal for the U.S. women’s gymnastics team. Her determination and resilience in that defining moment made her an American hero, […]

Caroline Rose is a remarkable individual, a beacon of resilience who has faced life’s most daunting challenges with unwavering strength and determination. At the young age of 27, Caroline, a pre-med student at USC, received the devastating diagnosis of Stage IV, highly aggressive, incurable non-Hodgkin’s lymphoma. This news came at a time when she was […]

Britt Frank, LSCSW, SEP received her undergraduate degree from Duke University and her master’s degree from the University of Kansas, where she later became an award-winning adjunct professor. Britt is a licensed psychotherapist and human behavior expert who literally wrote the book on getting unstuck. The Science of Stuck, (Penguin Random House) is now available […]

Immaculée Ilibagiza is a remarkable and inspirational speaker whose powerful story of survival and forgiveness has resonated with audiences worldwide. A Rwandan genocide survivor, Ilibagiza’s journey from the depths of despair to becoming a leading advocate for peace and reconciliation is both moving and transformative. Her story is one of extraordinary courage and unwavering faith, […]
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.
Connecting you with the perfect speaker.
We connect you with world-class speakers to create impactful, memorable events.
Tell us about your event and we’ll match you with the right speaker.
© All rights reserved 2026. Designed using Voxel