This Week in Startups – E2228

Episode Title: Jason’s ultimate dream mega-purchase + Founder Q’s
Date: December 29, 2025
Host: Jason Calacanis
Special Segment: Gamma Pitch with Zach Kidd, Ask Humans

Episode Overview

In this episode, Jason Calacanis dives into founder questions sourced from startup subreddits, exploring topics including extravagant purchases, founder mistakes in product validation, best practices for handling inbound VC interest, and the benefits and risks of taking European VC money for US-based startups. The episode also features a "Gamma Pitch" segment with Zach Kidd from Ask Humans, reviewing a new AI-driven feedback solution for organizations.

Key Discussion Points and Insights

1. Extravagant Purchases: Jason’s “Mega-Buy” Dilemmas

[00:00, 21:15, 24:13]

• Private Aviation: Jason openly shares his hesitance to spend large sums on private jet travel, even as his wealth increases.

  • “I've been trying to hold off on doing this for a long time. The great unjustifiable expense of spending, you know, $50,000 going somewhere or 100,000 on a round trip that seemed absurd to spend that.” (Jason, 00:12, 21:15)

• Collector Cars: Debates between a $250k Corvette ZR X1 or a collection of classic Corvettes — recognizes such purchases as ‘cognitive load’.

• Barndominium: Fascinated by the idea of owning a lavish ‘man-cave’ barn, Texas-style.

  • “A lot of these things become cognitive load...I like to not have cognitive load. And what I find is every time you own another home or you own another asset, it just becomes like a little bit of load on your processor.” (Jason, 21:15)

• Personal Values: Jason ultimately finds more fulfillment in investing early-stage checks to founders than owning luxury items.

  • “Putting buying a $50,000 1970 Corvette Stingray would give me some joy, but putting two 25k first checks in Founder University would give me more. I'll be totally honest.” (Jason, 21:15)

2. Mistakes in Product-Market Validation: The ‘Shark Bite’ Problem

[01:46–07:16]

• The Dilemma: A startup built a solution for a trucking company’s critical mistake (wrong fluid in wrong truck), landing a $20,000 pilot, only to learn other industry players don’t share this need.

• Jason’s Advice: Validate across several customers before scaling, as anecdotal crises are likely ‘shark bites’— rare, headline issues— versus ‘mosquito bites’, common, low-grade problems.

  • “This is why you want to get two or three customers and validate it across them.” (Jason, 02:41)

• Analogy Deep-Dive: Colorful discussion of the real rarity and media exaggeration of shark bites compared to the everyday ubiquity of mosquito bites, emphasizing market size.

• Founders’ Next Steps:

  • Offer the solution as bespoke software at a higher price, or train the customer’s team to maintain it;
  • Recognize “bespoke” (custom, niche) software is a viable business in the AI age, given how quickly such products can be built.
  • "Bespoke software is going to be the future. By the way, the fact you can build software so quickly now ... you can build bespoke businesses that make but a million dollars a year and you have a 50% margin." (Jason, 07:15)

3. Inbound VC Interest: How Founders Should Respond

[09:36–15:36]

• Situation: A founder with a popular open-source app receives inbound VC interest and is unsure how to respond.
  • “So VCs will hire associates, researchers, analysts, and they'll charge them with, go find me some interesting companies...” (Jason, 10:12)
• Jason’s Playbook:
  • Research the VCs—put them in a CRM, do back-channel references, and check their track records.
  • Maintain Focus—Only meet VCs if actively raising; otherwise, defer until the right timing.
  • Ball Control: Flip the power dynamic—founder as scarce commodity, VC as commodity.
    • "You have to understand you are the precious resource in this, not the investor. The investors are a commodity." (Jason, 13:26)
  • Beware Spam: Ignore cold outreach from unverifiable ‘investors’—could be scammers or brokers.
• Founder Tactic: Politely push meetings to the future or require in-person meetings on your turf to filter serious VCs.

4. Should US-Focused Startups Take European VC Money?

[15:36–19:31]

• Founder Dilemma: European founders in the US with American target market attract European VC interest—should they take it?
  • “Do not judge the VC's money, but judge their ability to help you succeed.” (Subreddit question summary, 15:36)
• Jason’s View:
  • “There are great venture capitalists all over the world...if they've got a great reputation and you vet their reputation by doing backdoor references from their CEOs, that's the best reference.” (16:18)
  • Backdoor References: Always seek founder references from the VC’s prior portfolio.
  • Money is Money: Competition for deals means you may be top priority for a European VC vs. just another deal for a top Silicon Valley firm.
    • “You might be the best deal that they're going to get into. Whereas...in the heart of Silicon Valley, you might not rise above with Sequoia's deal flow, but you might be the top of this firm's deal flow.” (Jason, 18:34)
  • Quality Counts: Geography less important than reputation, term sheet quality, and engagement.

5. Industry Beliefs Jason Disagrees With

[24:13–27:18]

• AI’s Role in SaaS:
  • Jason is bullish on continued value creation from vertical SaaS applications and non-generic product experiences, even as AI commoditizes core capabilities.
    • "There's always a way to create a more refined product that solves a singular problem for a small group of people. And you add features and community and design that speaks to that group." (24:23)
  • Uses Calm, Brilliant.org, and Tonebase as case studies where deep specialization beats free/general content.

Notable Quotes by Segment

Extravagant Purchases & Humility

• “It's obnoxious to even talk about this kind of level of stuff...I like to stay humble. I like to not have cognitive load.”
  — Jason (21:15)

Founder Psychology: Ball Control

• “You are the precious resource in this, not the investor. The investors are a commodity. In, I'd say 70% of investors do not add any value. And in some cases, they detract value.”
  — Jason (13:26)

Market Validation: Shark v. Mosquito

• “There's more money spent on mosquito bites than there are in shark bites. But shark bites, man, my feed on TikTok and Instagram is all shark bites... As far as I'm concerned, people are getting bit by sharks 10 times a day. And that's not what's happening.”
  — Jason (02:41)

[Gamma Pitch] “Ask Humans”: AI-Powered Feedback Platform

[28:24–44:53]

Pitch Summary

• Product: Ask Humans — platform for collecting and leveraging open-ended feedback (text, audio) from club members, staff, or clients at scale.
• Clients: High-end clubs (NEDs Club, owned by Soho House) and public agencies (e.g., Washington D.C. Economic Partnership)
• Expansion: Moving from external feedback tools to integrated internal tools (calendars, meetings, recurring loops, transcriptions, AI-powered analysis).
  • “We are bringing together a calendar... we are also doing meetings... loops which are reoccurring check in questions... studies... and presentations. All of this we're building with the ability for you to talk to the data and actually to listen to personal podcasts as a summary of all the feedback that's coming along.” (Zach Kidd, 30:57)
• Modality Insights:
  • Users greatly prefer audio (easy, multilingual, low friction); video is unpopular.
  • “No one wants to do video. And one thing that people love is the audio. One, it's multilingual. Two, it's super easy to multitask. And three, people don't want to think about, you know, how to exactly phrase what they're saying. They just want to talk.” (Zach Kidd, 35:50)
• AI-Driven Follow-up: Product can ask clarifying, personalized follow-up questions via AI.
  • “If somebody says, hey, the club is far too crowded and there's not enough staff... it could, yeah... come up with a good follow up question.” (Jason, 37:17)
• Quantitative Impact: Departments saw a 60% increase in feedback collection rates compared to traditional methods.
• Sentiment Analysis: Ongoing work to ensure accuracy of red-yellow-green feedback metrics; confidence increases as LLMs improve.
  • “You should assume that the LLM models are going to get 50 times better and make sure that doesn't make your product less relevant.” (Zach Kidd, 44:13)

Memorable Feedback & Transparency Segment

• Jason advocates for transparent, unfiltered sharing of feedback internally:
  • “There's no filtering of it when it gets to me. And we give it to our speakers, even if they get a low rating... So just these tools are great. You just got to make sure that nobody tries to massage the results to protect the guilty.” (Jason, 43:02)
• Reference to Ray Dalio’s radical transparency and Teddy Roosevelt’s practice of receiving first-hand feedback for effective leadership.

Notable Quotes from the Pitch

• On Feedback Loops:
  “If all of their verbal feedback can come onto one platform that you can then interact with, that's a very powerful and entrenched solution that really drives collaboration and knowledge forward for that organization.”
  — Zach Kidd (39:31)

• On AI Sentiment Analysis:
  “Every time from when we went from 4 to 5.0 in terms of how our data is better and better as a result.”
  — Zach Kidd (44:13)

Timestamps for Critical Segments

• Extravagant Purchases: 00:00–01:46, 21:15–24:13
• Shark Bite Problem/Product Validation: 01:46–07:16
• Handling Inbound VC Interest: 09:36–15:36
• European VC Dilemma: 15:36–19:31
• Jason’s Unpopular Industry Belief (AI/SaaS): 24:13–27:18
• Ask Humans Pitch: 28:24–44:53

Episode Tone & Takeaway

The tone is candid, practical, and sometimes irreverent—Jason’s hallmark. He’s forthright about wealth and founder psychology, always stressing humility, focus, and staying close to the fundamental needs of building and scaling startups. The episode is rich with analogies and actionable advice, especially for founders navigating the messy realities of early validation, investor relations, and the tension between opportunity and distraction.

For Founders & Listeners

If you’re a founder:

• Validate your market widely; don’t scale off one ‘shark bite’.
• Treat inbound VC interest strategically—curate, qualify, and always play ball on your terms.
• Don’t be distracted by shiny objects, whether luxury assets or high-profile VCs.
• Leverage new feedback tools but maintain a culture of radical transparency.

If you’re an aspiring founder, investor, or operator, this episode offers insight into both mindset and tactical execution at the earliest—and often messiest—stages.