Inside the All-In Podcast: How to Win in Media, Lessons from Elon, Travis Kalanick, Trump, Investing in 100+ Startups per Year with Jason Calacanis
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode, Jason Calacanis, host of the All-In Podcast and founder of Launch Accelerator, shares insights from his three decades building media companies and investing in startups. From studying master interviewers like Oprah and Charlie Rose to being an early investor in Uber and Robinhood, Jason discusses the art of podcasting, venture investing strategies, and the evolution of media. (39:00) He reveals the behind-the-scenes origins of the All-In podcast during COVID and its unexpected influence on the 2024 election.
- Core themes: The episode explores mastering communication through authentic storytelling, building successful media businesses by playing in emerging platforms, and developing contrarian investing strategies that focus on "what if it works?"
Speakers
Jason Calacanis
Jason Calacanis is the host of the All-In Podcast and This Week in Startups, co-founder of Launch Accelerator, and famously the "3rd or 4th investor in Uber." He started seven media companies over three decades, including Silicon Alley Reporter and Weblogs Inc (which included Engadget). Jason was Sequoia Capital's first scout and has invested in companies like Uber, Robinhood, DataStax, and Thumbtack through his early-stage investing programs.
Key Takeaways
Listen Deeply, Ask Follow-Up Questions
The best interviewers don't rely on predetermined question lists - they listen intently to answers and build follow-up questions from what was just said. (06:44) Jason learned from studying masters like Charlie Rose and Howard Stern that "the next best question is embedded in the previous answer." This creates synchronicity with the audience who just heard the same response. Most interviewers fail because they're nervously thinking about their next scripted question instead of being present in the moment and doubling down on interesting details from the current answer.
Embrace the "What If It Works?" Mindset
When evaluating new opportunities, especially in emerging categories, ask yourself "what if it works?" rather than focusing on why it might fail. (76:47) This mindset led Jason to invest in Uber when most VCs wanted it to become enterprise software for cab companies, and Robinhood when people said millennials don't have money to invest. Both companies manifested entirely new markets that didn't previously exist. The key is looking past current limitations to imagine the potential if the vision succeeds.
Master Communication Through Authentic Expression
The most compelling podcasters and content creators aren't trying to be part of the podcasting industry - they're pursuing artistic expression first. (17:07) Jason highlights how authentic voices like Brett Easton Ellis and Red Scare succeed by being genuine rather than following podcasting formulas. They focus on expressing themselves authentically rather than trying to build a media business, which paradoxically makes them more compelling and successful.
High-Volume Early-Stage Investing Strategy
In today's competitive venture landscape, the biggest opportunities exist at the very early stage and very late stage, with the middle being overcrowded and overvalued. (57:57) Jason's Launch strategy involves making 100-150 investments annually with small checks, expecting 80-90% won't make it to Series B. This high-volume approach with accelerator-style programs allows for maximum surface area while minimizing individual bet size, recognizing that hitting even one or two major winners can make an entire fund.
Fundraising Is Simply a Numbers Game
Most founders give up too early in the fundraising process, typically after 20 meetings when they should be prepared for 100-200 conversations. (68:00) Jason emphasizes that with only 1% acceptance rates, even exceptional companies need massive outreach. The key insight is that you only need 2-3 investors to say yes out of 100, not unanimous approval. Founders should apply this same volume approach to accelerators, applying to multiple programs since they all have sub-1% acceptance rates.
Statistics & Facts
- Jason's Launch Accelerator receives approximately 20,000 applications per year for funding, with the team conducting about 500 applications per week. (60:21) They invest in roughly 1 in 150 to 1 in 200 applicants who apply.
- About 60% of companies that go through Launch's Founder University program successfully raise another round of funding at a higher valuation within the first year. (63:54)
- Jason lost 43 pounds using GLP-1 medications, going from 213 pounds down to 170 pounds at 5'8" tall. (97:22) He describes this as like removing a 35-pound weight vest he was carrying 24/7.
