Straight Answers
An LLM assessed 279 question → answer exchanges, the host's own answers included. Speaker names were hidden during assessment. Each exchange was marked answered, partly, redirected or not addressed, with a quote as its source. Every exchange below is timestamped and plays. How it works →
These readings are observational: the transcript shows whether the question was answered directly, whatever the reason. It is an AI reading of a public exchange, never a claim about intent, and the tape is one tap away on every row. full disclaimer →
Nobody here carries a rate, and that is deliberate: rates are not published without enough raw tape, which means 8 or more assessed questions on raw, unedited recordings, and every In Depth episode we hold is the produced feed. So this page counts instead of rating. Every one of the 84 people on the record is accounted for: 47 have their questions counted (5 of them with at least one not answered directly), and the remaining 37 never took a direct question in any tape we hold: compilations, panels and cameo appearances leave nothing to assess.
No needle for In Depth Ledger: every tape we hold is the produced feed, and rates are not published without enough raw tape. So the board below counts exchanges instead of rating them.
All speakers
All 47 people with assessed questions on the record, ranked by how many were not answered directly. Every count comes from the produced feed. Click a name to see their exchanges.
| Person | Redirected + not addressed | Questions | Tape | Argument clarity /5 |
|---|---|---|---|---|
| Bob Moore Co-Founder & CEO, Crossbeam | 1 | 6 | raw | ≈4.5 |
| Matt MacInnis Chief Product Officer, Rippling | 1 | 6 | raw | ≈4.0 |
| Dennis Pilarinos Founder & CEO, Unblocked | 1 | 6 | raw | ≈4.5 |
| Kyle Parrish Partner, Craft Ventures | 1 | 6 | raw | ≈4.5 |
| Brett Berson Partner, First Round Capital | 1 | 1 | raw | — |
| Jay Parikh EVP of CoreAI, Microsoft | 0 | 6 | raw | ≈4.0 |
| Cameron Adams Co-founder & CPO, Canva | 0 | 6 | raw | ≈4.5 |
| Jake Stauch Co-founder & CEO, Serval | 0 | 6 | raw | ≈4.5 |
| Qasar Younis Co-founder & CEO, Applied Intuition | 0 | 6 | raw | ≈4.5 |
| Ankur Goyal Founder & CEO, Braintrust | 0 | 6 | raw | ≈4.5 |
| Wes Kao Co-founder, Maven | 0 | 6 | raw | ≈4.5 |
| Adam Guild Co-founder & CEO, Owner.com | 0 | 6 | raw | ≈4.5 |
| Eeke de Milliano Head of Global Product, Stripe | 0 | 6 | raw | ≈4.5 |
| Kevin Busque Co-founder & CEO, Guideline | 0 | 6 | raw | ≈4.5 |
| Varun Anand Co-founder & Head of Operations, Clay | 0 | 6 | raw | ≈4.5 |
| Bill Magnuson Co-Founder & CEO, Braze | 0 | 6 | raw | ≈4.5 |
| Matt Lerner Co-Founder & CEO, SYSTM | 0 | 6 | raw | ≈4.5 |
| Yuhki Yamashita Chief Product Officer, Figma | 0 | 6 | raw | ≈4.5 |
| Tristan Handy Founder & CEO, dbt Labs | 0 | 6 | raw | ≈4.5 |
| Krithika Muthukumar Entrepreneur in Residence, Thrive Capital | 0 | 6 | raw | ≈4.5 |
| Eoghan McCabe Co-Founder & CEO, Intercom | 0 | 6 | raw | ≈4.5 |
| Anneka Gupta Chief Product Officer, Rubrik | 0 | 6 | raw | ≈4.5 |
| Casey Winters Co-Founder and CEO, SuperMe | 0 | 6 | raw | ≈4.5 |
| Sam Schillace Deputy CTO & CVP, Microsoft | 0 | 6 | raw | ≈4.5 |
| Milin Desai CEO, Sentry | 0 | 6 | raw | ≈4.5 |
| Adam Nash Co-Founder and CEO, Daffy | 0 | 6 | raw | ≈4.0 |
| Michael Cieri Chief Product Officer, BILL Holdings | 0 | 6 | raw | ≈4.0 |
| Stephanie Berner Chief Customer Officer, Smartsheet | 0 | 6 | raw | ≈4.5 |
| Neha Narkhede Co-founder & CEO, Oscilar | 0 | 6 | raw | ≈4.5 |
| Oliver Jay Former Chief Revenue Officer, Asana | 0 | 6 | raw | ≈4.5 |
| Michael Lopp Senior Director of Engineering, Apple | 0 | 6 | raw | ≈4.5 |
| Steve Blank Adjunct Professor, Stanford University | 0 | 6 | raw | ≈4.5 |
| Jack Krawczyk Senior Product Director, Meta | 0 | 6 | raw | ≈4.5 |
| Will Larson CTO, Imprint | 0 | 6 | raw | ≈4.5 |
| Ashley Kramer Chief Revenue Officer, ElevenLabs | 0 | 6 | raw | ≈4.5 |
| Colin Zima Co-Founder & CEO, Omni | 0 | 6 | raw | ≈4.5 |
| Wade Foster Co-founder & CEO, Zapier | 0 | 6 | raw | ≈4.5 |
| Alex Kracov CEO & Co-Founder, Dock | 0 | 6 | raw | ≈4.5 |
| Noah Desai Weiss Chief Product Officer, Slack | 0 | 6 | raw | ≈4.5 |
| Saumil Mehta Global President, Ticketmaster | 0 | 6 | raw | ≈4.5 |
| Ryan Glasgow Founder and CEO, Sprig | 0 | 6 | raw | ≈4.5 |
| Kevin Mandich Head of Machine Learning, Sprig | 0 | 6 | raw | ≈4.5 |
| Kellan Elliott-McCrea Head of Engineering, Adobe | 0 | 6 | raw | ≈4.5 |
| Tara Seshan Product Lead, OpenAI | 0 | 6 | raw | ≈4.5 |
| Jack Altman General Partner, Benchmark | 0 | 6 | raw | ≈4.5 |
| Anique Drumright Chief Product Officer, Harvey | 0 | 6 | raw | ≈4.5 |
| Kevin Wang Chief Product Officer, Braze | 0 | 1 | raw | — |
The moments, on tape
The question Brett asked, then the AI assessment note from the answer. Tap to play the moment. Not addressed = the question was not engaged; redirected = acknowledged, then steered elsewhere.
“How do you, how do you solve fine tuning and custom inference? Um, that would be a very different transformation or pull away from the sort of core product that we're building than I think what we're experiencing.”
answered: “Is there anything else that has gone on that has allowed you to so closely associate”
“Are there any stories that come to mind of those first couple of years that were critical moments for you as you were building out the go to market function that other people might find inspiration from or learn something that might be useful to their own journey?”
answered: “You've got to find the boundaries to protect yourself from burnout.”
“To wrap up, I'm curious, when you think about all the spectacular people that you've had the chance to work with, is there anything that just pops to mind that's had some sort of disproportionate effect on the way that you think about Building companies now. Could you kind of crystallize the thing that they imparted on your worldview?”
answered: “It's like one big growth thing for me from when I was younger”
“You touched on this a little bit, but what was the first version of the product? How did you figure out how minimum it could actually be?”
answered: “One of the things I learned really quickly was that people actually already do this”
“Do they come from all sorts of small companies, big companies, startups? There's just no rhyme or reason.”
answered: “You had these great interview questions, which I thought were the most”
Every count on this page comes from the produced feed: no raw unedited tape of In Depth exists in our library. Rates are not published without enough raw tape, so this page counts and shows no percentage. This is a reading of a transcript. It is not an accusation of dishonesty, and there are many good reasons not to answer a question directly (confidential numbers, unreleased products, someone else's news to break).