Simanjeet Ahluwalia

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Quick Info

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Group call with Simi, Gavyn, Jimmy, and Fil to plan Jyot’s bachelor trip
Long conversation with Gavyn and Fil being not particularly helpful, but the group decided on getting the Emsdale cottage in Muskoka - one of Simi’s suggestions
Simi called me personally after the group call
Expressed frustration with the call, the maturity level of the group, and concern about incidents since his Airbnb is being used for the trip
Confirmed he works at Sompo International (Japanese insurer Sompo Holdings acquired Bermuda-based Endurance Specialty Holdings for $6.3B in 2017 to form Sompo International), on the Elevate team (North America strategic arm), office near Times Square in NYC
We also spoke about his job situation:
- Said he’s luckily still employed but feels like they’re setting him up to fail
- Not in a position to succeed at his current role
- Described it as his worst career decision so far
- Having issues with the COO - the CEO hand-picked the COO, and Simi works on the regional side (Elevate team) whereas most others work on the product side (Endurance/reinsurance), which creates political friction
- Actively looking for a new job and meeting with recruiters
- Mentioned a Program Director role at Manulife as one opportunity
Listened and chatted through his frustrations

Messaged this morning confirming a group call tomorrow (2026-03-29) at 7pm to plan Jyot’s bachelor party for June 6th-8th

Spoke at 7pm
His wife’s dad has passed away, so he won’t be going to Thailand anymore
Suggested we should still go
Said he’d organize Ikjyot’s bachelor party for the weekend here in June at a cottage

Call from 7pm-9pm with Ikjyot Gill regarding the bachelor party trip
Simi had gone to his late friend Paulo’s birthday party on the 07th - Paulo was Guyanese and passed away last year, so friends gathered on his birthday this year
Said Paulo was a “legend” and everyone knew him
Danced until 3am, had to leave his car and drive back in the morning to pick it up - hadn’t anticipated drinking/partying that much
They had booked out the entire restaurant and opened it up to dance near the end
His daughter Sristi (Seeshu) came on screen, me and Ikjyot said hi, but she went off screen and muted to have a conversation with Simi
Sristi told him the bachelor party was insensitive given their mom’s current troubles and him “not being his age”
I mentioned this may be a difference of culture (individualistic vs. collectivist) and coping mechanisms on grieving
Simi will discuss with his wife (also named Simi) and Sristi on Tuesday, then get back to us on whether he can go - after which we’ll buy tickets and confirm

Messaged him and Ikjyot Gill in the morning with flight research for incoming/outgoing and left some open questions; no response since the afternoon

Group call with Ikjyot Gill for Ikjyot’s bachelor party planning, 8pm-10pm
Simi raised concerns about trip length, his wife’s father potentially about to pass, and his step-dad about to pass as well
Convinced Simi to fly out May 15-16th to June 2nd to catch the Thailand full moon party
Simi wanted to book airline tickets immediately; I wanted to do more research first, which caused some tension
Simi kept cutting me off, I felt excluded and got agitated, made some slightly tense remarks
Ended fine overall but still slightly tense atmosphere
Reconvening Sunday 7-8pm (2026-03-08)

WhatsApp call with Ikjyot Gill to plan Ikjyot’s bachelor party
Wedding coming up second week of July
Discussed locations: Brazil, Thailand, Colombia, Spain
Conclusion: Thailand
Reconvening 2026-03-04 to discuss individual research and findings for Thailand along with preferences