This Week in Startups – Avoiding Buzzwords and Marketing-speak

Episode 2236 | January 16, 2026
Host: Jason Calacanis
Guest: Thomas McInerney (Angel Investor)
Location: Live in Tokyo at Founder University

Episode Overview

This episode dives into what makes a great early-stage founder — with a particular focus on cutting through the noise of buzzwords and marketing fluff. Angel investor Thomas McInerney joins Jason Calacanis before a live audience of new founders to discuss red flags, heuristics, and lessons from over a decade of investing in companies like Segment, Notion, Uber, OpenAI, SpaceX, and many more. The pair also offer live feedback to startups pitching from the stage.

Key Discussion Points & Insights

1. What Makes a Backable Founder

• Technical competence and domain expertise are key. Thomas repeatedly emphasizes he looks for "technical founders with domain expertise, generally pretty young. They have a point of view about something that they know, that they understand. And normally it's a bit different." (00:00, 14:10)
• Focus on being different: “If you're one of a hundred entering some crowded space... it's going to be super, super hard. So you have to be weird, you have to be different." (16:28)
• The ‘Idea Maze’ Metaphor: Both discuss founders needing to have traversed a detailed “idea maze” — demonstrating deep understanding of the territory and awareness of possible pitfalls.

“Marc Andreessen talks about this, the idea maze... when you talk about an idea with them, you can see that they've tried this, they've tried that, they've thought about it this way, they've thought about it that way. They are so deep in it that when they're talking to you, it becomes immediately clear or should be clear that they don't have all the answers, but they know what they know."
— Thomas McInerney (18:51)

2. The Dangers of Buzzwords and Hype

• First red flag: marketing-speak and jargon.

“When people start using buzzwords, I get... very turned off. I want it in simple English, because... you're taking too much from the outside world and those trends are sort of like fashion, they change daily. And so I think being able to reduce your idea into like a real simple concept that's not using a lot of buzzwords is, is good.”
— Thomas McInerney (00:16, 26:17)

3. Red Flags and Investment Turn-offs

• Overvaluation: Founders seeking high valuations too early signals misaligned priorities. “Not to be greedy about equity but rather to be focused on getting the right people on board. And once if you do that, everything takes care of itself. If you make something big, whether you own 10, 20, or 30%, it won't matter.” (00:44, 26:51)
• Unkindness in Small Interactions: Thomas tests founders by seeing how they treat wait staff during meals — a “poker tell” for character and leadership (27:06).
• Hiring and team building: “The ability to also hire and inspire. That's a really important one for me.” — Jason Calacanis (27:29)

4. Evolution of Startup and Angel Investing

• The early days were authentic, “a smaller universe of people... there was a lot of authenticity just because it was a smaller universe of people, people that were really in it and doing it because that’s what... they didn’t know anything else.” (07:28)
• Angel investors once provided rare access; now, capital is a commodity, so reputation, support, and curation are more vital than money alone (09:31).
• On risk-taking and optimism:

“Be an optimist, I think... even AI was quite bullish on AI, but I should have bet bigger into the AI trend.”
— Thomas McInerney (38:34)

5. Execution in the First Year

• Don’t blow your first capital. The most common failure: running out of money due to overspending. “You would be shocked the number of companies that I've been an investor in that have gone wrong from overspending… It is crazy.” (32:18)
• Frugality is a core strength: Get a dollar of value from a nickel, not from a hundred-dollar bill (33:08).
• Runway discipline: “That is your oxygen… you run out of gas, the plane is going down.” (33:44)

6. Fundraising Tactics

• Beware of “almost closed” rounds: Only signed term sheets count (35:38).
• Force clarity: “Say, what do you need to get to a yes here? What do you need to like sign the term sheet? ...Your investors will generally -- and your customers too -- they'll tell you what they need.” (36:49)
• Push for timelines: Good investors respond well to a nudge for process and deadlines (37:48).

7. Choosing What to Fret About

• Founders focus on opportunity first, then risk.

“The mind of a non-founder goes first to the risk... Whereas a founder sees that opportunity and then they're like, okay, these challenges are risks and I can manage them or I can deal with them, but they first go to the opportunity versus going to the risk.”
— Thomas McInerney (41:06)

• Optimism as a steering mechanism:

“There's this great expression that they tell drivers, you know, in race cars, look at the track, not the wall. Because you look at the wall, you drive into the wall.”
— Jason Calacanis (39:47)

• Survivorship increases your luck: “If you hang around long enough in Silicon Valley, you get hit by the money truck.” — Adam Ross (42:32)

8. Returns and Understanding Exponential Outcomes

• Angel investing is an outlier field: the possibility of 1,000x returns is hard for human brains to compute (44:06).

Notable Quotes & Moments

• On enjoying the founder “volley”:

  “Is it enjoyable to volley, to play tennis, to play ping pong, pickleball, whatever it is with the founder... They need to have that humility to engage that discussion, but also that confidence of we're going to figure that out.”
  — Jason Calacanis (18:06)

• On opportunity in declining markets:

  “You want to find a beach where the tide's coming in, not going out."
  — Jason Calacanis, feedback during live pitches (49:24)

Timestamps for Key Segments

• 00:00–03:31 – Thomas’s background & move to Tokyo
• 05:27–10:14 – Early days of angel investing and what’s changed
• 14:10–18:51 – Evaluating early stage founders: technical backgrounds, idea maze, humility
• 26:12–27:29 – Major red flags: buzzwords, valuation greed, small “tells” for character
• 32:18–35:38 – Managing capital and avoiding common early-stage pitfalls
• 36:20–37:48 – Best fundraising processes: asking direct questions, pushing for clarity
• 38:17–41:34 – The importance of optimism, focusing on opportunity, and learning from misses
• 44:06–45:26 – The exponential nature of startup outcomes

Live Pitch Feedback (47:31–63:19)

Satedomist (cross-border AI commerce for Sake exporters)

• Feedback highlights:

  • Too narrow and declining market—must show larger, growing opportunity.
  • Explain the fundamental problem: compliance and paperwork for any regulated export.
  • Choose a more general, scalable name for the service.

  "This pitch had all these signals of no, no, no, no. And then at the end it had the... oh, he's going to do it for these other verticals. But the name also, then you're trapped in the name. So I want you—and I'm going to give you permission—to think big... Think about the problem broadly."
  — Jason Calacanis (49:24, 50:08)

Homie World (AI-powered trust-based real-world social network)

• Feedback highlights:

  • Emphasize founder’s background as a “connector.”
  • Focus initial go-to-market tightly; expat communities in Tokyo is a promising beachhead.
  • Viral growth and trust are core to any successful consumer social product.

  "Consumer apps are incredibly hard until they're not. And it's very much about finding a behavioral loop that people become addicted to and that actually solves that problem for them. And I'm not convinced that you found it yet, but... Airbnb hosts, eBay sellers: who are your builders?"
  — Jason Calacanis (55:36)

  "I think you could take advantage of that also. I like that you really hit upon trust, you know, in order to meet someone in real life, I mean, especially for women, there has to be a trust component there. So I think that's definitely going to be part of your secret sauce is getting that right."
  — Thomas McInerney (60:06)

Conclusion

This episode offers a masterclass in early-stage founder evaluation, the evolution of startup investing, and the mindset needed for breakthrough innovation — all delivered in a candid, practical, and occasionally humorous tone true to Jason and Thomas's style.
Aspiring founders and angels alike will benefit from the focus on authenticity, discipline with resources, and clarity in pitching — with actionable advice for sharpening their odds of long-term success.