Jason Calacanis: Greatest Angel Investor

  • Highlights:
    • Advisor to Elon Musk, Executive at Twitter. Greatest Angel Investor & Bestselling Author. Host of This Week In Startups
    • Jason Calacanis is a member of the trusted inner circle for Elon Musk and possibly the next CEO of Twitter.
    • Jason authored the best-selling book Angel: How to Invest in Technology Startups: Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000.
Reading time: 3 min
Reviews: (0 reviews)
  • Travels from: San Francisco, CA
  • **Fee range: $75,001 - $100,000

Keynote Topics

  • What does it take to create a successful tech company?
  • And how do you know if a tech company is worth investing in?

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:

  • Uber: Calacanis was an early investor in Uber, the ride-sharing giant that has revolutionized the transportation industry.
  • Thumbtack: He invested in Thumbtack, an online marketplace that connects consumers with local service professionals.
  • Robinhood: Calacanis also backed Robinhood, the fintech company that popularized commission-free stock trading.
  • Trello: He was an early investor in Trello, a project management tool that was later acquired by Atlassian.
  • Calm: Calacanis invested in Calm, a meditation and sleep app that has gained immense popularity.
  • Inside.com: He founded Inside.com, a news aggregation service that aims to provide concise and informative news briefs.

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

Jason Calacanis | Greatest Angel Investor

Videos

Interest to Book? Send us your enquiry

Speaker Contact Form

Enquiry Form

No reviews available for this post.

Was this profile helpful?

Talent FAQ's

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.

  • Virtual speaking appearances are a cost-effective alternative to high speaking fees, often 10-50% cheaper than in-person rates.
  • There is typically no difference in fee for a 15-minute speech versus a 60-minute speech.
  • Some motivational speakers are open to discounting their fee if hired for more than one event by the same organization.
  • When browsing speakers, consider their location to keep travel costs down.
  • Personal connections to your organization or event location can increase your chances of securing a renowned speaker.
  • Be upfront about your needs and expectations to ensure a successful partnership.
  • Speaker bureaus like Speakers Inc help guide you through the booking process to negotiate the best deal with favorable terms.

Ready to find the perfect speaker for your event? Use our advanced search feature or contact us to get started today!

View further speakers

  • (33)
Tanya Menon

Tanya Menon is a renowned leadership strategist and keynote speaker who helps organizations and teams bridge the gap between where they are and where they need to be. With a focus on leadership development, team dynamics, and organizational culture, Tanya has spent decades studying human behavior in organizations. She empowers leaders to make strategic decisions […]

  • Travels from: Columbus, OH
  • Organizational Culture
  • (24)
Dr. Brian Glibkowski

Dr. Brian Glibkowski is a pioneering force in the realm of business communication, best known as the creator of Answer Intelligence (AQ)™. His groundbreaking work on the role of questions and answers in business and society has revolutionized how leaders, teams, and organizations approach problem-solving, decision-making, and strategy formulation. With a passion for enhancing communication […]

  • Travels from: Chicago, IL
  • Emotional Intelligence
  • (37)
Liz Bohannon

Liz Bohannon is a dynamic and influential leader whose impact resonates deeply across the realms of customer service and leadership. As the co-founder and CEO of Sseko Designs, Liz has championed a unique approach to ethical business practices and leadership that intertwines social impact with entrepreneurial success. Her compelling journey from a Peace Corps volunteer […]

  • Travels from: Portland, OR
  • Culture Speakers
  • (35)

Pat McGann is rapidly establishing himself as one of the sharpest voices in stand-up comedy today. Known for his quick wit, clever storytelling, and relatability, Pat has become a favorite among audiences seeking smart, laugh-out-loud entertainment. With his unique perspective and seamless delivery, he connects effortlessly with fans, creating an unforgettable experience that resonates well […]

  • Travels from: Chicago, IL
  • Comedian Hosts
  • (24)
Piers Kowalski

Piers Kowalski stands as a beacon of advocacy, leadership, and inspiration in the realm of LGBTQ rights and inclusive corporate environments. With a fervent dedication to fostering positive change and championing diversity, Piers has carved a remarkable path as a professional speaker, consultant, and advocate. His journey is one characterized by a relentless pursuit of […]

  • Travels from: Colorado Springs, CO
  • LGBTQ Speakers
  • (33)
Robyn Benincasa

Robyn Benincasa has made an art form of extreme performance by competing and winning at the highest levels of sport and business. Robyn is an award-winning keynote speaker, a 20+ year veteran San Diego firefighter, a World Champion Adventure Racer, a 2014 CNN Hero, a Guinness World Record Endurance Kayaker, a best-selling author, and founder […]

  • Travels from: Cardiff-by-the-Sea, CA
  • Motivational Speakers
  • (56)
Alli Webb

Alli Webb is the co-Founder and Chief Creative Officer of Drybar, the nation’s leading blow dry bar offering customers no hair cuts and no hair color, just professional blow outs at an affordable price. After leaving the hair care workforce in 2005 to start a family, Alli looked for an opportunity to continue pursuing the […]

  • Travels from: Los Angeles, CA
  • Business Speakers
  • (29)
Nadya Zhexembayeva

Called ‘The Reinvention Guru’ (In Ventures magazine) and ‘The Queen of Reinvention’ (TEDx Navasink), Dr. Nadya Zhexembayeva is a business owner, educator, speaker and author — specializing in reinvention. As a business owner, Nadya oversees a group of companies active in real estate, investment, and consulting. As a consultant, Nadya has helped such organizations as […]

  • Travels from: Columbus, OH
  • Strategy Speakers
Disclaimer
The profiles and images embedded on these pages are from various conference entertainers and other talent.

These remain the property of its owner and are not affiliated with or endorsed by Speakers Inc.

Fee ranges where listed on this website are intended to serve as a guideline only.

All talent fees exclude VAT, travel and accommodation where required.

Subscribe to our Newsletter and get connected:

Your subscription could not be saved. Please try again.
Your subscription has been successful.

Newsletter

Subscribe to our newsletter and stay updated.

We use Brevo as our marketing platform. By submitting this form you agree that the personal data you provided will be transferred to Brevo for processing in accordance with Brevo's Privacy Policy.

Our Mission:

We are your partner creating memorable and engaging experiences that go beyond the event itself.

© All rights reserved 2026.  Designed using Voxel

AI Assistant
Speakers Inc Logo 2024
Privacy Overview

This website uses cookies so that we can provide you with the best user experience possible. Cookie information is stored in your browser and performs functions such as recognising you when you return to our website and helping our team to understand which sections of the website you find most interesting and useful.