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Virgil Carroll @vcmonkey

Building digital strategies and stuff people can use since 1998

Joined March 2007
  • Tweets 9,367
  • Following 515
  • Followers 1,246
336 Photos and videos
TechCon 365 Chicago is next week. Here's where to find me: Wed 6/17 @ 2:50 PM - Ask the Experts, Expo Hall Thu 6/18 @ 12:50 PM - Room S103A Fri 6/19 @ 10:20 AM - Room S102A Code VIRGIL200 saves $200 if you're still registering. techcon365.com/Chicago/ticke…
Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.

ALT Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.
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One week until TechCon 365 Chicago. Two sessions. One Ask the Experts slot. All focused on Search and Copilot. Code VIRGIL200 saves $200 on registration. techcon365.com/Chicago/ticke… #TechCon365 #MicrosoftSearch
Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.

ALT Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.

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My favorite conference moments are rarely the sessions, they are the real conversations. Pick my brain on Wednesday, June 17 at the McCormick Place South Expo Hall! techcon365.com/Chicago/ #TechCon365 #MicrosoftSearch #AskTheExperts

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techcon365.com
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Out of the box is a starting line, not a finish line. "Making Microsoft Search your own" - TechCon 365 Chicago Fri, June 19 | 10:20 AM | Room S102A Code VIRGIL200 saves $200. techcon365.com/Chicago/ticke… #TechCon365 #MicrosoftSearch
Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.

ALT Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.
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Is Microsoft Search actually dead? That is the question I will answer at TechCon 365 Chicago. Thu, June 18 | 12:50 PM | Room S103A "Replaced by AI: Is Microsoft Search dead?" Code VIRGIL200 saves $200. techcon365.com/Chicago/ticke… #TechCon365 #MicrosoftSearch #Copilot
Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.

ALT Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.
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Speaking at TechCon 365 Seattle, August 24-28. I'm doing two sessions on Microsoft Search, Copilot, and the content strategy that connects them. techcon365.com/Seattle/ #TechCon365 #MicrosoftSearch #Copilot

TechCon 365, DATACON & PWRCON - Microsoft 365, DATA & Power Platform Conference

techcon365.com
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"We turned on Copilot. Why can't people still find anything?" Almost never a tool problem. Almost always a content foundation problem. Digging into this at TechCon 365 Chicago in June. Code VIRGIL200 saves $200. techcon365.com/Chicago/ticke… #TechCon365 #MicrosoftSearch
Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a nighttime Chicago skyline background.

ALT Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a nighttime Chicago skyline background.
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Excited to be speaking at TechCon 365 Chicago, June 15-19. Two sessions all focused on Microsoft Search and why it still matters in a Copilot world. Use code VIRGIL200 to save $200 on registration. techcon365.com/Chicago/ticke… #TechCon365 #MicrosoftSearch #Copilot
Here is alt text for this image: Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.

ALT Here is alt text for this image: Promotional graphic for TechCon 365 Chicago, June 15-19, 2026. Text reads "I'm speaking at TechCon 365 Chicago. Save $200 with code VIRGIL200. Register now." Headshot of Virgil Carroll, CEO of High Monkey, appears on the right against a Chicago skyline background.
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Discussing Stupid just crossed 1,000 listeners this season. Seven episodes still to go, and the conversations are only getting better. We're just getting started. highmonkey.com/blog/discussi…
Celebrating graphic for Discussing Stupid Season 3 reaching 1,000 listeners, featuring bold text and the Discussing Stupid logo.

ALT Celebrating graphic for Discussing Stupid Season 3 reaching 1,000 listeners, featuring bold text and the Discussing Stupid logo.
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Virgil Carroll retweeted
Space
@intodotspace
29 Dec 2025
Coming soon to Seeker. Space x @solanamobile
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Everyone is asking AI how to fix their SEO. Very few people are fixing the content problems underneath it. New Discussing Stupid episode: discussingstupid.com/episode…
Promotional graphic for Discussing Stupid Season 3, Episode 6, titled "Intentional AI: You’re asking AI to solve the wrong problems for SEO/GEO/AEO". Features bold text, an "Out Now" indicator, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 6, titled "Intentional AI: You’re asking AI to solve the wrong problems for SEO/GEO/AEO". Features bold text, an "Out Now" indicator, and the Discussing Stupid logo.
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Virgil Carroll retweeted
Space
@intodotspace
9 Dec 2025
Oracle speaks. Money moves. Space x @PythNetwork
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Virgil Carroll retweeted
Space
@intodotspace
5 Dec 2025
Impossible is a skill issue.
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New episode is live! We tested how AI handles accessibility checks and plain language rewriting. Some helpful results, some not so helpful. discussingstupid.com/episode…
Promotional graphic for Discussing Stupid Season 3, Episode 5, titled "Intentional AI: How much can you trust AI for accessibility?". Features bold text, an "Out Now" graphic, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 5, titled "Intentional AI: How much can you trust AI for accessibility?". Features bold text, an "Out Now" graphic, and the Discussing Stupid logo.

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Virgil Carroll retweeted
Kaspiy
@Kaspiy
26 Nov 2025
It’s fascinating to watch the shift happening in real time among crypto’s big name OG angel investors. Throughout the past 4 years - it was all about $. Sign the SAFT, help hype the token, exit on retail. Repeat. Now? These guys are looking for "meaning". You can almost feel the irritation in their tweets and private chats. - Another L1 with “ultra-low fees”? - Another “capital-efficient” L2? - Another stablecoin that’s just USDC with a different logo? - Another DEX promising “native yield” that’s really just a Ponzi in a nicer UI? Sure, with the right KOLs, the right launch partner, and a juicy FDV, the round gets 10x oversubscribed and "the early cabal" makes a quick bag. A bit later the project just becomes another "wtf is this" line on Coinmarketcap. The angels who already printed life-changing money from those plays aren’t chasing another 5-10x anymore. Now they are in a search of meaning. A signal in a world drowning in noise. - Projects that ship real utility instead of narratives. - Projects that have a boring money-making business, not the "ok, how do we get 1000000 yaps about us and 1000 likes on this tweet?" projects. - Founders who are obsessed with product and users, not just token price and vesting schedules. They want to back the things that ten years from now, people will point to and say, “That’s why crypto mattered.” If we've had kept this filter on since 2020, we’d be so much further ahead as an industry. But better late than never. The tide is turning right now, today. More and more people are finally asking the question it should have asked all along: “Does this move crypto forward or is it just another way to extract from it?” And for the first time in years, the answer is not a marketing stunt, and actually matters to them.
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This week in our Intentional AI series, we’re looking at how AI fits into content management. Automation helps with the busy work, but it can't replace good process. Full episode here: discussingstupid.com/episode…
Promotional graphic for Discussing Stupid Season 3, Episode 4, titled "Intentional AI: Content Management with AI". Features bold text, an "Out Now" graphic, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 4, titled "Intentional AI: Content Management with AI". Features bold text, an "Out Now" graphic, and the Discussing Stupid logo.

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That's a wrap on @TechCon365  Dallas. A big thank you to everyone who came to my sessions, stopped to chat, or shared ideas in the hallway. Already looking forward to the next one!
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Starting in one hour, “Making Microsoft Search your own.” If you’ve ever been frustrated by default Search results, this one’s for you. 12:30 PM | Room G3 | #TechCon365 techcon365.com/Dallas/ticket…
Virgil Carroll TechCon 365 Dallas promotional graphic: Making Microsoft Search your own

ALT Virgil Carroll TechCon 365 Dallas promotional graphic: Making Microsoft Search your own
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Speaking tomorrow at TechCon 365 Dallas: “Making Microsoft Search your own.” This one’s all about customizing Search so it actually works for your org. Friday 12:30 PM | Room G3 techcon365.com/Dallas/ticket… #TechCon365 #MicrosoftSearch #Microsoft365 #Copilot
Virgil Carroll TechCon 365 Dallas promotional graphic: Making Microsoft Search your own

ALT Virgil Carroll TechCon 365 Dallas promotional graphic: Making Microsoft Search your own
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Speaking tomorrow at TechCon 365 Dallas: “Making Microsoft Search your own.” This one’s all about customizing Search so it actually works for your org. Friday 12:30 PM | Room G3 techcon365.com/Dallas/ticket… #TechCon365 #MicrosoftSearch #Microsoft365 #Copilot
Virgil Carroll TechCon 365 Dallas promotional graphic: Making Microsoft Search your own

ALT Virgil Carroll TechCon 365 Dallas promotional graphic: Making Microsoft Search your own
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