Concept Mockup
Tuesday · 5 May · Cleveland

Good morning,
Robert.

Three matters need a moment of your attention this week. The household is in steady stewardship; Aspen is on watch. Charles is on duty until 9 PM ET.

Insured Value
$48.2M
across 7 categories
Annual Premium
$284,510
↓ 3.2% vs. prior year
Coverage Health
94/100
2 gaps identified
Open Matters
3
2 in progress · 1 awaiting you
Confidence
You know what's covered, and what's not — and why.
98 · your last rating
Guidance
A real human, who knows your household, when you need one.
100 · your last rating
Ease
The boring parts handled in the background. Your time, back.
97 · your last rating
Quantifiable Value
What you get back, measured — not just promised.
$184k · recovered '24–'26
At a glance

The Ellsworth family

Open map
RE
Robert
You
CE
Catherine
Spouse
EE
Elise · 21
Yale, junior
JE
Jonathan · 18
Hotchkiss, senior
WE
William · 15
Hotchkiss, sophomore
Shaker Heights, Ohio
The Fairmount Residence
Primary · 9,200 sq ft$6.4M
Pre-winter inspection · Nov 4
Aspen, Colorado
Red Mountain House
Seasonal · 6,800 sq ft$14.2M
Wildfire perimeter advanced — board-up team on standby
Naples, Florida
Gordon Drive Villa
Seasonal · 7,400 sq ft$11.8M
New York, NY
740 Park Pied‑à‑Terre
Co-op · 2,100 sq ft$5.6M
Live · Updated 4 min ago

Risk Weather

All signals
Aspen. Wildfire perimeter advanced 4.1 miles toward Red Mountain. IoT sensors active; vetted contractor queued for board-up.› Awaiting your authorization to dispatch
12 min
Digital perimeter. Impersonation account flagged on LinkedIn under your name. Takedown initiated.› We will confirm when removed (24–48h)
2h
Yale, New Haven. Phishing campaign targeting students surfaced. Elise's identity monitoring is active; we have notified her.
6h
Naples. Tropical system tracking south of cone. No action; we continue to monitor.
9h
Carrier health. All carriers AM Best A or better. No watch items.
1d
Anticipated

Life events

All
14
May

Twombly drawing departs for Milan loan

Endorsement drafted with Galleria Borghese. Just needs your signature.

Have a look →
22
May

Naples renovation — coverage alignment

Builder's risk active through 12 Aug; contents schedule will adjust on completion.

04
Jun

Family travel · Tuscany & Lake Como

Medical evac confirmed. K&R cover active. Pre-trip security brief prepared by Argosy.

Open itinerary →
CRO Dashboard

Coverage position

Detail
Property & contentsFour residences
Strong
Personal umbrella$50M tower
Strong
Fine art & collectibles42 scheduled items
Watch
Cyber & reputationHousehold + dependents
Strong
Watercraft & marineNewport sloop
Gap
Household employees5 staff · EPLI
Strong
Gap flagged · Brancusi maquette acquired in October has not yet been added to the schedule. Sotheby's appraisal received yesterday — we'll prepare the endorsement on your approval.
Concierge

"What can we help with today, Robert?"

CW
Charles Whittaker
Your Oswald team · on call until 9 PM ET
Vault · Recent activity

Documents in motion

Open vault
Trust amendment — Article VII (charitable remainder provisions)Uploaded by Michelman & Robinson · viewed by Catherine
2h ago
Sotheby's appraisal — Brancusi (maquette, ed. 4/8)$1.42M · Received with provenance file
1d
Naples renovation — architectural plans v3Shared with Skanska · permission expires 30 Jun
3d
Newport sloop — pre-season survey & layup checklistHinckley yard · scheduled 12 Nov
1w
On the calendar

Upcoming

12
Nov

Newport · sloop lay-up survey

Hinckley yard, 9 AM

15
Nov

Your 2026 recap

Mailed to Fairmount

18
Nov

Aspen · pre-season inspection

Snowmelt systems, security audit

An annual edition

Your 2026 recap.

Bound, numbered, and delivered. A documented record of what was protected this year, what changed, and what is anticipated — the kind of artifact your family will keep on the shelf. Yours arrives at Fairmount on 15 November.

Open the digital edition →
An annual recap
prepared for
The Ellsworth Household
Oswald 360
2026
Household  ›  Properties  ›  Aspen  ›  Red Mountain House

Red Mountain
House.

2741 Red Mountain Road, Aspen, Colorado. Seasonal residence. The household is monitoring an active wildfire to the southwest. Caretaker is sheltering off-site; sensors are clean as of the last reading.

Active situation · Awaiting your authorization.
Henderson Building Co. crew is staged. Authorize board-up to dispatch.
Dwelling Limit
$14.2M
replacement cost basis
Contents Limit
$3.8M
incl. 6 scheduled items
ALE
$580k
12 mo · pre-approved
Carrier
AIG Private Client
A.M. Best A · 12-yr relationship
Asset profile
TypeSingle-family seasonal
Year built1991, renovated 2017
Square footage6,800
Lot3.2 acres
Owner of recordRMH Holdings LLC
CaretakerM. Henderson
Security firmArgosy Group
Last appraisalMar 2025
Pre-season inspection18 Nov scheduled
Notable contents
Twombly drawing$2.1M
Patek Philippe collection$840k
Wine cellar (1,400 bottles)$385k
'67 Porsche 911S$220k
Today · Tuesday 5 May

Response timeline

Full log
06:14 ET · 04:14 MT

Smoke detected · west perimeter sensor

Particulate exceeded threshold for 90 seconds. Neighborhood corroboration via Aspen Fire alert at 06:11. Automated alert routed to the Concierge desk.

06:18 ET

Reviewed and corroborated by Charles

Charles Whittaker confirmed sensor reading against InciWeb feed. Initial perimeter 11.4 miles southwest. Wind from west-southwest at 14 mph; trajectory consistent with advance toward Red Mountain.

06:24 ET

Family principal notified · text and Cockpit alert

Sent to Robert Ellsworth at preferred channel (mobile). Catherine notified via her preferred channel (Cockpit only). No call placed; matter deemed below escalation threshold at this stage.

07:00 ET

Caretaker contacted · perimeter walkthrough

M. Henderson confirmed sheltering at family residence in Snowmass. Conducted remote IoT walkthrough — no smoke ingress, HVAC dampers closed, water shut-off ready. Argosy Group security on-site within 22 min, perimeter clear.

09:30 ET

IoT inspection complete · all readings nominal

Smoke, temperature, humidity, occupancy, and security all within normal range. Wine cellar climate stable. Logged for the file.

Sensor report · 09:30 ET
12:45 ET

Perimeter advanced 4.1 miles · now 7.3 mi from residence

InciWeb update at 12:43 confirmed advance. Wind sustained west-southwest. Aspen Fire Protection District public notice issued for adjacent neighborhoods (not yet for Red Mountain).

13:02 ET

Adjuster prep call scheduled · AIG Private Client

Scheduled with AIG senior adjuster D. Markham for 14:30 ET. Standard precautionary prep — no FNOL filed yet. AIG has been the carrier since 2014.

13:32 ET

Henderson Building Co. crew staged for board-up

Vetted contractor on Oswald's vetted contractor list. Estimate $14,200, fully covered under emergency mitigation. Four-person crew, 35-min ETA when you give us the green light.

Contractor estimate · $14,200
NOW · 14:12 ET

Awaiting your authorization to dispatch

Decision required by 15:00 ET to maintain crew positioning. Below this threshold no action is taken; escalation can be revisited as conditions evolve.

Perimeter · live
Red Mtn House 7.3 mi 14 mph WSW N ↑
Fire perimeter Residence
Sensors · Red Mountain
Interior temp
68°F
Steady
Humidity
42%
Nominal
Smoke / particulate
0ppm
Clear since 06:18
Air intake
Sealed
Auto-engaged 06:18
Wine cellar
55°F
Stable
Perimeter security
Armed
Argosy on-site
Pre-approved actions · awaiting you
Dispatch board-up crew$14,200

Henderson Building Co. crew of four. Boards 9 windows and 3 doors on west and south elevations. Reimbursable under emergency mitigation. Decision required by 15:00 ET.

Move scheduled items off-site$2,850 transit

Twombly, Patek collection, and provenance archive to Oswald-vetted vault in Denver via secured transport. 6-hour notice; below threshold today.

Open precautionary FNOL with AIGNo cost

Files a precautionary notice without a claim. Preserves rights and accelerates handling if conditions deteriorate. Recommended.

Wildfire defensible space
Class A
Last graded by Oswald risk engineer · Sep 2025
Deductible
$50,000
Per occurrence · standard private client
Wildfire defense svc
Wildfire Defense Systems
Pre-positioned in evacuation tier; AIG endorsement
Last claim
2018
Hail · roof replacement · $42k
Your scorecard · 2026

How are we doing?

Once a year we ask. The four things we measure — Confidence, Guidance, Ease, Quantifiable Value — because they're the four things that actually matter to you. Your last scorecard came in at 98 out of 100. We're not done yet.

98.6/100
Average Oswald Score
87% of our clients rate us 98.6 out of 100. We're not going to round up.
40%
Response Rate
Two-fifths of our clients fill this out every year. That's roughly 4× the industry average.
$184k
Recovered for you · '24–'26
Claims, mitigation credits, and renegotiated premium that landed back with your family.

Your turn — rate us, briefly.

Four questions. Two minutes. We read every single one.

Confidence

Do you know what's covered, and what's not — and why?
98

Guidance

Is your Oswald team there when you need them?
100

Ease

Is the friction out of the way? Is your time respected?
97

Quantifiable Value

Can you see what you're getting back — in dollars and otherwise?
96
Your scorecard history

Four years with Oswald.

2023
94
First year
2024
96
↑ 2 pts
2025
97
↑ 1 pt
2026
98
↑ 1 pt · in progress
What other families and businesses are telling us

You're in good company.

"They actually picked up the phone at 11 PM on a Sunday when the basement flooded. I didn't even know that was a thing anymore."
— A family principal, Cleveland · 2025 scorecard
"In ten years with our previous broker, we never once had someone explain a policy line we didn't understand. In one year with Oswald, every line."
— CFO, manufacturing client · 2025 scorecard
"The annual recap they sent felt like it was made for our family — not pulled from a template. That's not a small thing."
— A family principal, Shaker Heights · 2026 scorecard
"Renewal used to take a week of back-and-forth. Now it takes a phone call and a signature. That's the whole story."
— Family-office director · 2026 scorecard
Your annual recap · 2026

A year, in your hands.

Every November we put together a recap of the year — what changed, what we caught, what we recovered, what's coming. It's printed, bound, and mailed to Fairmount. The digital version lives here.

An annual recap for

The Ellsworth family.

2026 edition · 48 pages · Printed in Cleveland
An annual recap, prepared for
The Ellsworth
family.
Oswald · 2026
No. 0001 of one
A letter from your team

Robert, Catherine

Another year handled. Here's what we caught, what we recovered, and what we're watching for 2027.

Your scorecard this year came in at 98 out of 100, up a point. We won't take credit for the one you didn't give us — that's on us, and we'll work on it.

A few things worth marking before you read on. Aspen held; no losses despite three active fire incidents in the valley. The Twombly traveled safely. Identity monitoring caught the LinkedIn impersonation within 24 hours.

We'll see you in January for the annual review at the residence. Until then.

— Charles Whittaker

On behalf of your Oswald team

3
Your 2026, in numbers

The year, on a page.

Insured value$48.2M↑ $1.4M
Annual premium$284,510↓ 3.2%
Claims closed3
Value recovered$184,000
Coverage health94 / 100
Properties watched4
Specialists on call11
Days quiet312 of 365
12
Things we caught this year

Quiet wins.

May · Aspen, Colorado
Red Mountain wildfire
Perimeter advanced to 7.3 miles from the residence. Sensors and a pre-staged board-up crew kept losses at zero. We won't pretend it wasn't close.
September · Rome
The Twombly loan
Galleria Borghese requested the drawing. Endorsement signed, conservation reviewed, insured-for-loan in 72 hours.
November · Online
LinkedIn impersonation
An account using Robert's photo and name was active for 36 hours before our monitoring caught it. Takedown completed within 24.
October · The schedule
The Brancusi maquette
We caught the gap before you did. It's now scheduled and appraised.
13
Where your premium goes

The shape of coverage.

Property · four residences 50% $142k
Art, collections & valuables 22% $63k
Excess liability · umbrella 10% $28k
Auto · seven vehicles 7% $20k
Cyber & identity 6% $17k
K&R, employment, other 5% $14k
22
Five years with Oswald

The trend, steady.

$360k $330k $300k $270k 2022 2023 2024 2025 2026 $284k
Your premium
HNW market peer

The market for high-net-worth coverage has risen 18% over five years. Yours has come down 8%. The gap is what working with us is meant to look like.

23
Watching for 2027

What's on the horizon.

May–August 2027
Aspen wildfire season
Defensible space re-grading in May. Sensor network biennial calibration.
November 2026
Twombly returns from Borghese
Conservation specialist already lined up for the receipt review.
December 2026
Robert turns sixty-five
Medicare coordination with the executive medical plan. We'll walk through it with your CPA well before the date.
Q1 2027
Trust amendment review
Your counsel at Michelman & Robinson has flagged a forthcoming review of generation-skipping provisions.
42

Your full edition runs forty-eight pages, including the appendices, the carrier panel, and the claims register. It arrives at Fairmount on 15 November.

A digital copy lives in your Vault, watermarked and access-logged.

— Your Oswald team
Oswald · 2026
48
Spread 1 of 3
In Good Company

The right person. The right introduction. From a network you can trust.

Insurance is what we do. The rest of it — the introductions, the trusted vendors, the people who can actually help — is the part nobody talks about. We do. When you need someone, we know someone.

What can we help you find?

A trusted advisor
Estate counsel, family CPA, wealth advisor, a second opinion on something complicated.
A vendor or specialist
Art handler, security firm, conservator, household ops, contractors we've worked with for years.
A board candidate
Independent directors, advisory board members, governance specialists from our network.
A peer connection
Another Oswald family or business owner navigating something similar. With both sides' permission, always.
A charitable partner
Foundations, family-office giving advisors, organizations doing meaningful work in your areas of focus.
Something else entirely
Tell us. Odds are we know someone — and if we don't, we'll find someone worth your time.
Recent introductions

Who we've connected you with this year.

EH
Eleanor Hammond, Conservator
For: Paper-works review when the Twombly returns from Borghese · Introduced: March 2026
Connected
DC
Daniel Chen, Family-office CPA
For: Medicare integration ahead of Robert's 65th · Introduced: April 2026
Connected
MR
Maya Rosenberg, Independent Director
For: Advisory board candidate for your operating company · Introduced: September 2026
Intro made
JV
James Volker, Security Specialist
For: Aspen residence perimeter assessment · Introduced: October 2026
Awaiting your reply
SH
Sarah Hwang, Charitable-Giving Advisor
For: Restructuring the family foundation around your three focus areas · Introduced: November 2026
Intro made
From the podcast · Latest episode

In Good Company · Episode 14

Three Cleveland family principals on what they wish they'd known about generational continuity at thirty-five. Hosted by Jessica Jung. 38 minutes.
Vault

Documents,
under stewardship.

Trust documents, appraisals, plans, schedules, deeds, directives — held with the same discretion you would expect from your private banker. Every share is logged. Every access expires. Nothing leaves without your knowledge.

Documents
2,847
across 8 categories
Active shares
14
3 expire this week
Confidential
186
principal access only
Last access · others
Michelman
2h ago · trust amendment
Trust amendment — Article VII (charitable remainder provisions)
Ellsworth Family Revocable Trust · current · 18 pages
Confidential
2h ago
Sotheby's appraisal — Brancusi maquette, ed. 4/8
$1,420,000 · provenance file attached · M. Cherwood, certified appraiser
Pending schedule
1d
Naples renovation — architectural plans v3
Coastal Architecture Group · shared with Skanska · expires 30 Jun
Shared · expiring
3d
Newport sloop — pre-season survey & layup checklist
Hinckley yard · marine survey by Capt. R. Halsey, AMS
Insurance
1w
Deed — 2741 Red Mountain Road, Aspen
Held by RMH Holdings LLC · Pitkin County recording 2017-3441
Property
2w
Healthcare directives — Robert & Catherine
Cleveland Clinic on file · executed Mar 2024 · annual review Mar 2026
Confidential
6w
Yale tuition · Elise · 2025–26 academic year
Bursar's office · paid in full Aug 2025 · 529 distributions logged
Family
2mo
Concierge · Your Oswald team

Charles is here.

Charles Whittaker has led your Oswald team for four years. He knows the household, the collection, the family travel rhythm, and the carriers. We get it — nobody loves dealing with insurance. The tech does the busywork. The people do the work that matters.

On duty until 9 PM ET
Avg. response · 2 min 14 sec
Across 312 conversations this year. After hours: Eleanor Saito, then on-call.
CW

Charles Whittaker

Online · Your Oswald team · 2 min response avg
Today · Tuesday 5 May
System · automated

Smoke detected at Red Mountain perimeter sensor. Concierge desk paged. No interior smoke; no occupants on premises.

06:14 ET
CW
Charles Whittaker

Robert — Charles here. Sensor flagged smoke at Red Mountain at 06:14 ET. I have corroborated it against InciWeb and the Aspen Fire alert; perimeter is currently 11.4 miles southwest, advancing west-southwest at 14 mph. Mrs. Henderson is sheltering at her sister's in Snowmass and is safe.

No action needed from you yet. I will text again at 11:00 ET with an update or sooner if conditions change. Standing by.

06:24 ET

Thank you. Loop Catherine. Keep me posted.

06:28 ET
RE
CW
Charles Whittaker

Catherine has been notified via her Cockpit. Argosy walked the perimeter at 07:00 — clean. IoT sweep at 09:30 — all readings nominal. I will check in at 11:00 as agreed.

09:32 ET
CW
Charles Whittaker

Robert — perimeter advanced 4.1 miles in the last 90 minutes. Now 7.3 miles from the residence. Sensors still clean and Argosy on-site, so the situation remains manageable, but I want to walk you through three precautionary actions and recommend authorizing the first.

Henderson Building Co. is staged for board-up. $14,200, fully reimbursable under emergency mitigation. Their crew can be on the property in 35 minutes from your authorization. Recommending we proceed.

I have also pre-positioned secured transport for the Twombly, the Patek collection, and the provenance archive — if you would like to move them to the Denver vault we can have a vehicle there in 6 hours. Below threshold today, but worth flagging.

Finally, I would recommend filing a precautionary FNOL with AIG. No cost, preserves your rights, accelerates any handling if conditions deteriorate. D. Markham at AIG is briefed and ready.

Henderson · estimate & insurance documents 3 files
13:56 ET
Awaiting your decision · 14:08 ET

Charles has flagged a decision point. To maintain crew positioning, authorize by 15:00 ET.

An Annual Edition · 2026

The Ellsworth
Stewardship Review.

A complete record of what was protected this year, what changed, and what is anticipated. Bound, numbered, and delivered to Fairmount on 15 November. Below, a preview of this year's edition.

A Stewardship Review
Prepared with discretion for

The Ellsworth
Household.

2026 EDITION
Oswald 360Cleveland · MMXXVI
A note from your team

A note before turning the page.

The work of stewardship is, more than anything, the work of attention. This year asked for a great deal of it.

You will find within these pages a record of the year as we kept it: the things added to the household, the threats we watched for and, in most cases, did not have to meet. Aspen will be remembered for the May fire that came within seven miles of Red Mountain and turned away on a wind shift; we kept the boards in the truck for a week afterward, as a courtesy to the next storm.

Catherine's work with the Cleveland Clinic Foundation continued to reshape the trust architecture, and Article VII was revised twice — once in March, once in November. Elise's junior year passed without incident; we expect more of the same as she begins her senior year. Jonathan begins college this fall.

It has been our privilege, again, to be of service. Thank you for trusting us with what is most yours.

Charles Whittaker Maître d', On Behalf of the Concierge Desk
— II —
The Year in Brief

The year, quantified.

A summary of stewardship — the figures behind a year of attention.

Insured value, year-end$48.2M
Insured value, year prior$44.9M
Annual premium$284,510
Premium vs. prior year−3.2%
Items added to schedule5
Items released or sold2
Coverage gaps identified · closed7 · 6
Risk Weather signals raised142
— of which required action11
Concierge conversations312
Average concierge response2 min 14s
Claims filed0
· · ·
— IV —
Notable Items Added

Notable additions to the household.

A small but significant year for the collection. Five items added; provenance and appraisal are filed in the Vault.

Brancusi · maquette, ed. 4/8
Acquired Galerie Maeght, October. Bronze with brown patina. Sotheby's appraisal Dec 14.
$1,420,000
Patek Philippe 2499 · perpetual chronograph
Phillips November auction. Yellow gold case, original certificate.
$385,000
A. Lange & Söhne · Datograph, 2005
Acquired through Christie's Geneva, September. Platinum.
$210,000
Alfa Romeo Giulia Sprint GTA · 1965
Concours-condition. Touring custodianship file transferred. Garaged Aspen.
$295,000
Cy Twombly · untitled drawing, 1962
Loan to Galleria Borghese, Milan, May 14 — Nov 2. Conservation file in Vault.
$2,100,000
— V —
Threats Anticipated

What was watched for, and met.

Of one hundred and forty-two signals raised this year, eleven required action. Each is held in the file for reference.

The Aspen wildfire on the 5th of May reached within seven miles of Red Mountain before a wind shift turned it south. Henderson Building Co.'s board-up crew was dispatched and stood down without action; we kept them on retainer for the week. AIG was briefed and the precautionary FNOL was withdrawn on the 12th. The defensible-space grading we revised in 2025 carried the day.

An impersonation account on LinkedIn was flagged on the 5th and removed within twenty-six hours. We will note that this is the third such instance this year, the second on LinkedIn specifically; we recommend continued monitoring on this surface and have engaged a takedown service on retainer.

Yale University's identity protection service flagged a phishing campaign targeting students. Elise was alerted; no further activity. We extended monitoring through her senior year as a precaution.

Hurricane Idalia's path was watched for nine days in September. Naples remained outside the cone; the home was not affected. Pre-storm protocol was rehearsed; the household staff received refresher training.

· · ·
— XII —
Forward

What we are watching for.

A look ahead, with care. The year to come and the matters that will ask for attention.

Jonathan begins university

Off-premises personal articles coverage will activate in August. Identity monitoring will extend to him on his eighteenth birthday. We will prepare a brief on dorm-life risk and digital hygiene.

AUG 2026

Naples renovation completes

Builder's risk releases on certificate of occupancy. Contents schedule will be reviewed and revised; replacement-cost basis will be re-anchored to current valuation.

AUG 2026

Trust amendment Article IX (anticipated)

Your counsel at Michelman & Robinson has flagged an upcoming review of the generation-skipping provisions. We will coordinate the document flow and ensure access logs are clean before counsel begins.

Q1 2027

Aspen wildfire season

National Interagency Fire Center early outlook indicates above-normal risk for Western Slope through August. Defensible space will be re-graded in May; sensor network will receive its biennial calibration.

MAY–AUG 2026

Twombly returns from loan

Galleria Borghese will return the drawing in early November. We'll line up an independent paper-works specialist for a conservation review when it lands.

NOV 2026

Robert turns sixty-five

We'll walk through how Medicare fits with your executive medical plan, together with your CPA, well before the date.

DEC 2026
— XIII —
Printed in Cleveland · delivered to Fairmount

Your full recap runs 48 pages, including appendices. It arrives at Fairmount on 15 November. The digital edition is here whenever you want it — watermarked and just for you.