Jason’s ultimate dream mega-purchase + Founder Q’s | E2228
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 holiday special episode of This Week in Startups, Jason Calacanis takes a unique approach by answering pressing questions from viewers and the startup community. The episode covers a range of topics from handling cold VC outreach to the psychology behind extravagant purchases, while also exploring the coexistence of AI agents and SaaS companies in the evolving tech landscape. (00:00) The episode concludes with the final Gamma Pitch Deck Competition entry, featuring AskHumans, an innovative approach to collecting and analyzing organizational feedback using AI.
• Main themes include founder decision-making when investors reach out, strategic considerations for European founders targeting American markets, and the future of AI-enhanced feedback systems in organizations
Speakers
Jason Calacanis
Jason Calacanis is a serial entrepreneur, angel investor, and host of This Week in Startups. He's a founding partner of Launch, a venture capital firm and accelerator that has invested in companies like Uber, Robinhood, and Calm. Calacanis previously founded successful companies including Weblogs, Inc. and has established himself as one of Silicon Valley's most prominent angel investors with early investments in companies that became worth billions.
Alex Wilhelm
Alex Wilhelm is a technology journalist and co-host of This Week in Startups. He has extensive experience covering the startup ecosystem and venture capital industry, bringing analytical insights to founder questions and market trends.
Zach Kidd
Zach Kidd is the founder and CEO of AskHumans, a platform that helps organizations collect open-ended feedback and act on it at scale using AI technology. His company has processed over a million minutes of recordings and works with clients ranging from private clubs to government agencies.
Key Takeaways
Maintain "Ball Control" When VCs Reach Out
When venture capitalists reach out cold, founders should control the timing and terms of engagement rather than jumping immediately into meetings. (09:22) Calacanis emphasizes that founders are the precious resource, not investors, and suggests responding with something like "we're not currently raising, but we plan to in Q4 of next year - Q3 would be a good time to talk." This approach creates scarcity and makes the VC more interested while allowing founders to focus on building rather than fundraising meetings. The key is to research the VC thoroughly, track them in a CRM, and only engage with legitimate firms that can add real value.
Quality Investors Transcend Geographic Boundaries
For founders targeting American markets but receiving interest from European VCs, the location of the investor matters less than their quality and ability to add value. (15:35) Great deals and great investors aren't constrained by geography, and European VCs may actually provide more attention and resources to a European founder than competing for attention at top-tier Silicon Valley firms. The critical factor is conducting thorough backdoor references with portfolio companies to understand how the investor actually performs when supporting startups.
Cognitive Load Management for High-Achieving Professionals
Success brings the temptation to accumulate assets and experiences, but each addition creates cognitive load that can distract from core objectives. (22:25) Calacanis reveals his own struggle with expensive purchases like private aviation and sports cars, noting that every additional property or asset becomes "a little bit of load on your processor." The key insight is evaluating whether purchases actually add value to life or just create more things to manage, emphasizing the importance of staying focused on primary objectives rather than getting distracted by material possessions.
AI Applications and SaaS Can Coexist and Thrive
Contrary to industry pessimism about SaaS being wiped out by large language models, specialized vertical applications will continue to provide massive value by offering refined solutions for specific user groups. (24:26) Using examples like ToneBase for musicians and Brilliant.org for learning, Calacanis argues that while people can get basic information from YouTube or ChatGPT, they'll pay for specialized, polished experiences that go deeper. The analogy is that people can get calories from any food source, but they'll still pay premium prices for high-quality specialized products like Wagyu beef.
Feedback Systems Must Avoid Political Filtering
Organizations often fail when feedback gets massaged or filtered before reaching decision-makers, turning critical input into politicized summaries. (41:26) Calacanis insists that in his organizations, feedback from speakers and founders goes directly to everyone without filtering, even including negative ratings. He sends founder surveys from his personal email and has created systems where low scores (7 or below) go to one chat room and high scores to another. The key is ensuring nobody "shuts off access to feedback" and that honest, direct input reaches leadership to enable real improvements.
Statistics & Facts
- There are approximately 6 fatal unprovoked shark attacks per year globally, with 60-70 total shark bites annually. (05:02) Calacanis uses this statistic to illustrate the "shark bite vs mosquito bite" problem in startups - some founders build solutions for rare, severe problems rather than common irritating ones.
- AskHumans has processed over 1 million minutes of recordings in the past 10 months across their client base. (33:39) This demonstrates significant traction for their AI-powered feedback platform across various organizations.
- The Department of Buildings in Washington D.C. achieved a 60% increase in feedback response rates using AskHumans compared to previous systems, gathering 7,000 responses from 40,000+ permit applicants. (36:18) This shows the effectiveness of audio-based feedback collection over traditional survey methods.
