- Home
- Life Insurance
- Health Insurance
-
Personal Lines
Car Insurance Classic Car Insurance Homeowner's Insurance High-Value Home Insurance Condo Insurance Renters Insurance Landlord Insurance Dwelling Fire Insurance Vacant Dwelling Insurance Home Warranty Pet Insurance Flood Insurance Travel Insurance Jewelry Insurance Umbrella Insurance Motorcycle Insurance Watercraft Insurance Event Insurance Personal Articles Floater
-
Commercial Lines
Business Owner's Policy Commercial Event Insurance Small Business Insurance Short Term Rental Hotels, Destination & Resorts Commercial Auto Trucking Insurance Inland Marine Insurance Builder's Risk Insurance Worker's Compensation Ghost Worker's Compensation Policy Liability Insurance Employment Practices Liability (EPLI) General Liability Insurance Cyber Liability Insurance Error and Omission Barbershop & Salon Insurance Coffee Shop Insurance Industry Specific Cannabis Business Insurance Tattoo Insurance Real Estate Investors
- About Us
- Resources
Candor Investor Meetups Hartford / Glastonbury · 4th Thursday Every Month
Connecticut's monthly meetup for real estate investors, landlords, flippers and BRRRR-ers across Hartford County and surrounding markets. Bring your deals, your questions, and your appetite — Square Peg has you covered.
Connecticut's Hartford / Glastonbury investor hub — built for serious operators.
Candor Investor Meetups is a New England-wide real estate investor meetup network — and this is our Hartford / Glastonbury room. We serve investors across Hartford County and the surrounding Connecticut markets — Glastonbury, East Hartford, Manchester, West Hartford, Wethersfield, Newington, South Windsor, Vernon, Rocky Hill and beyond.
Every 4th Thursday, the hub gathers at Square Peg in Glastonbury for an evening of real conversation, real deals and real connection — no fluff, no pitch parade, just Connecticut investors helping Connecticut investors do better business.
InsureCT is proud to sponsor the hub because protecting Connecticut real estate investors is exactly what we do. Bring your portfolio questions — we'll be there.
One night a month. The right people in the room. The deals, the playbooks and the partners that move your portfolio forward — right here in Hartford County.
When
4th Thursday of every month
Where
Square Peg · 1001 Hebron Ave, Glastonbury, CT 06033
Who
Real estate investors, landlords, flippers, wholesalers & BRRRR operators
Region
Hartford County & surrounding Connecticut markets
A working room for Hartford-area investors — not a pitch fest.
Whether you own one rental, run a portfolio, or you're still hunting for your first deal, the hub is built around the conversations that actually move investors forward.
Hartford-area Networking
Trade deals, contractors, lenders and lessons with active Connecticut investors who know your market.
Real Deal Talk
Numbers on the table — buy boxes, BRRRR refis, multifamily underwriting, flips, rentals and creative finance.
Trusted Local Pros
Meet contractors, attorneys, lenders, agents, property managers and insurance brokers who actually serve CT investors.
Q&A With Operators
Bring your sticking points — financing, tenants, permits, evictions, taxes — and crowdsource answers from people who've been there.
Casual Square Peg Vibe
Grab a bite, grab a drink, talk shop. Square Peg's relaxed Glastonbury setting makes it easy to actually connect.
InsureCT On Site
Our team will be there to answer landlord, BRRRR, flip, builders-risk, vacant-dwelling and umbrella questions — no appointment needed.
Candor Investor Meetups
Courtney Miller
Host · Candor Investor Meetups · Hartford / Glastonbury
Courtney leads the Candor Investor Meetups each month at Square Peg in Glastonbury — connecting Hartford County investors with the people, partners and playbooks that turn local deals into long-term wealth.
Her room is the kind where seasoned operators and brand-new investors actually sit at the same table. New faces are genuinely welcome — bring your questions, your wins, and the deal you're stuck on.
Want to attend, partner, or speak at an upcoming meetup? Reach out through Facebook or Meetup.com (links in the venue card below) — Courtney handles all hub announcements there.
Connecticut investors deserve an insurance partner who actually gets it.
We sponsor the Candor Investor Meetups because protecting Connecticut real estate investors is our core specialty. From the first single-family rental to a 50-door portfolio, we build coverage that fits the way you actually invest in this state.
Landlord & Rental Property
Tailored DP-3 and rental dwelling coverage for single-family, multi-family and small portfolios across Connecticut.
Flips & BRRRR Projects
Builders-risk and vacant-dwelling coverage that won't lapse mid-rehab — built for the way CT investors actually operate.
Multifamily & Commercial
Commercial property, general liability and umbrella stacking for investors scaling beyond residential.
Personal Umbrella
High-limit umbrella coverage to shield personal assets from rental property liability exposure.
Free Portfolio Reviews
Bring your declarations pages — we'll spot the gaps, the overlaps and the carriers leaving money on the table.
Local. Independent. Yours.
Independent CT brokerage shopping multiple A-rated carriers — not a captive agent locked into one playbook.
Candor Investor Meetups · Glastonbury — Quick Answers
Everything you need to know before your first meetup at Square Peg.
When does the Candor Investor Meetups meet?
The hub meets on the 4th Thursday of every month at Square Peg in Glastonbury, CT. For exact start time and any schedule changes, follow Courtney Miller's announcements on Facebook and Meetup.com.
Where is the meetup held?
All meetups are held at Square Peg, 1001 Hebron Ave, Glastonbury, CT 06033 — a casual, central Hartford County location with easy parking, food and drinks.
Who is the hub for?
The Candor Investor Meetups serves real estate investors across Hartford County and surrounding Connecticut markets — including landlords, house flippers, BRRRR operators, wholesalers, multifamily investors and people working on their very first deal. New investors are genuinely welcome.
How much does it cost to attend?
The meetup itself is free to attend — you're only responsible for whatever you order at Square Peg. For exact details and any RSVP requirements, check the latest Facebook or Meetup.com event link from Courtney Miller.
Do I need to RSVP?
RSVP isn't always required, but it's strongly recommended so the host has an accurate headcount for Square Peg. Use the Facebook event link or Meetup.com page in the venue section to RSVP.
Is this part of a larger network?
Yes — Candor Investor Meetups is a New England real estate investor meetup network with a local chapter right here in Hartford / Glastonbury. Our room is hosted locally by Courtney Miller and meets at Square Peg the 4th Thursday of every month. For sister chapters across New England, check the Candor Investment Meetups Facebook page.
What's InsureCT's role at the hub?
InsureCT is the proud insurance sponsor of the Candor Investor Meetups. Our team is on hand to answer questions about landlord, rental property, builders-risk, vacant-dwelling, BRRRR, multifamily, commercial and umbrella coverage — and we offer free policy reviews for every Connecticut investor in the room.
Can I get a quote or policy review without attending?
Absolutely. Use the form on this page to request a quote, a free policy review, or a callback. You'll be talking to a real, licensed Connecticut broker — usually within one business day, or one business hour for urgent requests.
Met us at the hub? Let's keep the conversation going.
This form is for connecting directly with Insure Connecticut LLC — separate from RSVP'ing for the meetup itself. Pick the option that fits, and we'll route your request to the right member of our team.
To RSVP for the next Candor Investor Meetups at Square Peg, please follow Courtney Miller's Facebook or Meetup.com event links.
Pick the policy review option — we'll compare your current rental, BRRRR or multifamily coverage against Connecticut's top carriers, free of charge.
Choose the urgent quote option — we'll reach out within one business hour so binder timing isn't a problem.
InsureCT Investor Contact Form
Sign up for our newsletter, request a free policy review, or get a quote built for Connecticut real estate investors. This is not an event RSVP form.
Scan to connect with InsureCT
Snap this code with your camera to jump straight back to this contact form from the meetup.