This article is a companion to Episode 1 of Speaking of Insurance, a conversation between Brian Bollinger and Aaron Bollinger released on 24 August 2026. It follows the conversation's own order, quotes the hosts where their wording is the point, and adds nothing they did not say. The episode page carries the full transcript.

The order matters. Get the insurance answer before you close — before contingencies come off, and before the kitchen has made the decision for you. The hosts have watched the premium on a house turn out to be more than the loan payment.

It starts with the address

Brian's first point is the one nobody can change after the fact: insurance begins with the location. You cannot move the home you love, and if it sits in brush you should expect to pay more for coverage. Everything else on this list is negotiable, documentable or fixable. The address is not.

“Updated” means completed, not patched

Older homes carry charm and they carry questions — structural ones, and the four systems every carrier asks about: electrical, plumbing, roof and heating and cooling. Aaron's warning is specific. When a listing or a quote form says the roof was “updated in 2000,” and what actually happened was a couple of patches on an original roof, that does not count as an update. Carriers are looking for full, completed replacements, and they ask when. Records, or an inspection report that establishes the dates, are what you want in hand.

What to ask your inspector to document

  • The heating and cooling system's install date. There is a date code on the label. You are paying a professional to read it so you do not climb onto the roof.
  • When the plumbing was replaced. Copper in the attic carries a manufacture date on the pipe; Brian describes pulling back the sleeve to read it. Photographs and dates, not impressions.
  • The electrical panel, photographed. Most inspectors will not call a panel safe or defective; they will photograph it. Ask whether they know an electrician who can say whether it needs to be upgraded to satisfy an insurer. Brian names Zinsco and Challenger among the panel makes that at least need to be addressed.

His summary of the gap between professions is worth keeping: a homeowner and a realtor look at a house and see how gorgeous it is; an insurance professional looks at the same house and asks what the cost drivers are that everyone wishes had been addressed.

The eight-figure house with a six-figure premium

Aaron tells the story of a buyer, years ago, closing on a home priced in the eight figures who did the right thing and asked what the insurance would cost before finalising. The answer was $80,000 to $100,000 a year — plausibly more than the loan payments. The point is not the number. The point is that he asked. Without that market gauge, a buyer can find that the preferred carriers will not write the home, the specialty carriers may not either, and the answer is a FAIR Plan policy on a very expensive property.

Brian extends it to cash buyers, whom Bollinsure sees at every price from a few hundred thousand to tens of millions. Paying cash removes the financing contingency — and with it the natural pause in which insurance gets checked. His advice is to build an insurance contingency of your own: a known budget for what you are willing to spend and what coverage you expect to have, settled before the money moves.

Do not inherit the seller's policy

The seller's current premium is not your premium. Brian describes grandfathered products the carrier will not offer again on the same terms, so the $2,000 or $5,000 or $50,000 the seller pays can be irrelevant to what you will. Aaron puts a number on how often to trust it: “Don't go off of the current insurance on the property 90 percent of the time. Like 90 to 95 percent of the time, don't.”

The other half of the quote is you. Carriers look at the property — address, year built, updates, surroundings, brush clearance, condition — and they look at the buyer: your claims record, in the way an auto carrier pulls a driving record. A small water claim on a prior property counts. Brian adds that some carriers, in some states, pull credit, and on the auto side motor vehicle reports; Aaron describes carriers estimating annual mileage from service-visit odometer readings. Both hosts land on the same caution about any carrier offering something that sounds too good: it is being done for the carrier's benefit, and if it did not make them more profitable they would not do it.

Five things to do before you sign

Aaron's checklist, in his order:

  • Give a broker the address and a few basic details early. Before you are emotionally committed.
  • Let them gauge the market — and choose one with experience placing property, not one who will hand you a FAIR Plan policy by default.
  • If the exposure is moderate, a captive carrier may fit. Aaron says this as an independent broker: where a direct carrier is the right answer for a moderate-risk home, an honest broker tells you so.
  • As value rises, or brush gets closer, look at other options. Standard carriers cap how much they will insure on a dwelling and grow less willing as value and exposure climb. That is where specialty markets begin.
  • If the FAIR Plan is the only door, know what it prices on. Distance to a fire station, distance to a hydrant, brush clearance and whether the home sits in a fire-protection district all matter. And the hosts note a rule as it stood when they recorded: replacement cost coverage on the dwelling required a roof replaced within the last twenty years. Confirm the current requirement rather than rely on it — underwriting rules move.

Budget the house, not just the premium

Brian widens the roof point beyond the FAIR Plan. Many carriers ask about a roof over twenty years old on a home of twenty to fifty years, and a buyer who has not budgeted to replace one — he uses $10,000 to $50,000 for a roof, and around $20,000 each for electrical and air conditioning as ballpark figures — can find themselves tens to hundreds of thousands of dollars out, on top of a premium they did not anticipate. The house is a liability you are buying as well as an asset.

Moving markets

The last trap is geographic. A carrier happy to insure a condo in San Francisco may not write a cabin in Frazier Park, Mammoth, Big Bear or Tahoe. If the move takes you into brush or mountains, assume you will be changing carriers, and find a broker who makes that change easy rather than tedious.

Where to start

Our new homeowners page is written for exactly this moment, and home insurance covers the coverage itself. If you want a rebuild figure before you ask for a quote, the replacement cost estimator is free and needs no login. For what the FAIR Plan is and is not, see California FAIR Plan and DIC. And the simplest version of the hosts' advice: send us the address and the listing before you remove contingencies, and we will tell you what the market says — including when the answer is that a direct carrier will serve you better.

Primary sources