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Artwork for Context Window: AI, Insurance & The Humans Behind It
Business & Finance

How to get on Context Window: AI, Insurance & The Humans Behind It

Hosted by Kyle Nakatsuji, Dearborn Labs.

Should you pitch it?

Guest activity
Sometimes has guests
29% of recent episode titles look like interviews
Episode length
64 min
Median of recent episodes. That is the commitment you would be asking for.
Publishing
Monthly
9 episodes · last 2026-09-30
Language
English
The feed says "en" without a region, so the country is unknown.
Where it's from
Not established
No .uk domain and no region in the feed language. Apple reports the storefront, not the show, so we do not guess.
Reach
51
Percentile among shows you could realistically get on. Not a download count.
Check whether they charge. Some shows sell guest slots rather than booking them, and rates in some fields run to thousands. Nothing in a podcast feed reliably says so, so we do not claim either way. Ask before you write the pitch.
Worth a pitch. This show publishes its own contact, sits outside the national chart, is independently published, and its recent episodes show it books guests.

How this show compares to other business & finance podcasts

Episodes run noticeably longer than the Business & Finance average, so prepare for a conversation rather than a short segment.

Measured against every business & finance podcast in the directory that has published in the last year.

This show Category average
Episodes featuring a guest 29% 22%
Episodes in the last 90 days 6 7
Typical episode length 64 min 34 min
Episodes published in total 9 100
Reach percentile 51 50

Reach is a percentile among shows you could realistically get booked on, built from chart history, longevity, activity and cadence. It is not a download figure. Nobody outside a show can see those.

What the show says about itself

Welcome to Context Window: AI, Insurance & The Humans Behind It, the podcast for leaders, operators, and founders navigating the intersection of artificial intelligence and enterprise operations. Hosted by Kyle Nakatsuji, we discuss how real companies are deploying AI inside legacy industries like insurance, not as a hypothetical tech play, but as a practical blueprint powered by humans. Each episode features raw conversations with the builders and executives who are actually on the front lines managing data, scaling teams, and defining the future of business infrastructure.

Recent episodes

Straight from the feed. The quickest way to judge whether your angle fits.

  1. Why Humility Decides Whether AI Actually Gets Adopted | David McFarland, Coterie Insurance
  2. Will AI Take Your Job? Only If You Don't Use It | Rick McCathron, President and CEO of Hippo
  3. Buy the Expertise Not the Code with Bryan Falchuk, President and CEO of PLRB
  4. Go First and Go Positive with Joe Schmidt, partner at Andreessen Horowitz
  5. Why AI Should Industrialize Expertise Instead of Replacing It | Travis Hedge, Co-Founder + CEO Vouch
  6. Why AI Rewards the Problem Owner | Steve Lekas, Co-founder & CEO of Branch Insurance
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Similar podcasts

Shows on the same subject that publish their own contact and are still active. If Context Window: AI, Insurance & The Humans Behind It is not the right fit, one of these may be.

Built To Grow: Window Companies business · 5 episodes Closest match Insurance Covered Business · 176 episodes Closest match Insurance Unplugged with Lisa Wardlaw Technology · 84 episodes Closest match What's Brewing - Coffee, Convo, Insurance business · 24 episodes Closest match The Leadership Window business · 159 episodes Closest match Insurance Sync business · 58 episodes Closest match

Every show A to Z

Common questions

Does Context Window: AI, Insurance & The Humans Behind It accept guests?

Sometimes has guests. Interviews appear alongside other formats. This is our reading of the show's recent episode titles, not a statement from the show itself.

How do I contact Context Window: AI, Insurance & The Humans Behind It?

Yes. Context Window: AI, Insurance & The Humans Behind It publishes a contact address in its own RSS feed, and it is the show's own inbox rather than a shared network desk. We hold it and release it to people on a plan. We never invent an address and never send a pitch on your behalf.

How often does Context Window: AI, Insurance & The Humans Behind It publish?

It publishes about once a month. There are 9 episodes in the feed. Episodes run about 64 minutes.

Is Context Window: AI, Insurance & The Humans Behind It still active?

Yes. It has published within the last 90 days.