From Rivals to “We’re Doing It”

Molly Hooper and Paige Teel ran the two biggest competing property management companies in Rockland. Now they run Tides to Pines together — nearly five hundred Maine homes, one shared brain cell, and a single measure of success: guests who can’t wait to come back.

Before there was a Tides to Pines, there were two property management companies in Rockland — the two largest in the Midcoast, and direct competitors. One was run by Paige Teel. The other was run by Molly Hooper.

Then COVID hit Vacationland. Paige, who was serving as president of The Vacation Rental Professionals of Maine, found herself on the phone with her fiercest rival, comparing notes on regulations, border uncertainty, and how to save a tourist season. “It started as competitors, moved into survival mode,” Paige says on the episode, “and then from there, we’ve just been great friends ever since.”

Competitors, Then Colleagues, Then Co-Founders

The vacation rental boom that followed COVID gave Molly and her partners the chance to sell her company, SummerMaine, to national operator Vacasa — and for a stretch, both women worked inside the corporate machine they’d once competed against. What they saw there changed everything. They watched how the corporate model treated homeowners and guests, and they didn’t like it. So they built an exit strategy, called Molly’s old homeowners, and brought back the personal service those owners remembered.

Tides to Pines launched in December of 2023. The name was all Paige: Maine is the coast, the lakes, the mountains, the pines — and they had no interest in putting a ceiling on where they could grow. Was there a moment when they knew it would work? “Every day,” Paige says. Molly puts it even more simply. The two of them share one phrase: “We’re doing it.”

Two Clients in Every Transaction

For anyone who thinks Airbnb answers the phone when your rental’s furnace quits at midnight, Molly has news: those platforms are marketing channels, not managers. Tides to Pines is full service. They photograph and list each home, market it on Airbnb, VRBO, tidestopines.com and beyond, set the rates, coordinate housekeeping and maintenance, handle trash pickup and landscaping and snow removal, and staff a guest services team that answers real phone calls — from “does this home have a first-floor bedroom?” to fully curated stays with a private chef and an in-home masseuse.

“We do have two clients in every transaction,” Paige explains. “We have our homeowner and we have our guest.” Many of those homeowners are multi-generational — caring for a grandparent’s home they hope to leave to their grandchildren — and Tides to Pines sees its job as stewardship: helping owners preserve a piece of Maine while sharing it with guests who’ll treasure it. Today that adds up to roughly 485 homes stretching from Brunswick up through Boothbay, Acadia, and over to the Moosehead region, with Sunday River and the Maine beaches on the map for 2027 and 2028.

One Brain Cell, No Ego

Ask each what she admires about the other and you get a portrait of a genuinely complementary partnership. Paige points to Molly’s financial mind — a partner who has already examined ten options before you finish asking the question. Molly points to Paige’s tenacity, creativity, and energy: “She can put my thoughts on paper before I think about them.” The office staff jokes that the two of them hold entire conversations without words. The partners joke back that they share one brain cell.

Underneath the jokes is discipline. Disagreements get worked through on paper — best case, worst case, pros and cons — and both women are quick to say “I see it your way” or admit a call was made emotionally instead of logically. “Humility,” Paige calls it. “Coming into it not thinking you’re right every time.”

Their advice for two friends considering a business together follows the same thread: know your personal goals first. Molly and Paige are at different stages of life with different destinations, but the business moves them both down the same road. “People are first, and not the business,” Molly says.

Rip the Band-Aid Off

The hardest lesson of their first years together wasn’t a failure — it was learning to act on their instincts immediately, even mid-season, even when a change felt impossible in the moment. Whether it was switching reservation systems or moving people into different roles, waiting always cost more than acting. “When your gut says this isn’t right, you need to change it,” Molly says. “It is actually correct.”

Maine Is One Big Small Town

Molly has been in this industry since 2002, and she’s watched large corporations sweep into Maine and wash back out, over and over, for the same reason: Maine doesn’t work that way. Every successful vacation here rests on a web of local hands — the cleaners, the landscaper, the plumber, the kayak outfitter, the private chef, the neighbor who picks up the phone. “Maine is just one big small town,” Paige says, “and the degrees of separation are basically nonexistent.”

That’s also why they’ve turned down invitations to take the model to other states. “Our neighbors are the ones that make us successful,” Molly says. The people they contract with are Mainers who know how to treat people well — and Tides to Pines intends to keep doing business right here.

Growth With Guardrails

Growth, when it comes, is intentional. They don’t take on just any home — properties need the right amenities, real safety standards, and homeowners who share the vision, in areas where guests are already asking to stay. Five years from now, Molly wants Tides to Pines known as the leading vacation rental company in Maine — measured not by home count, but by reputation.

And the number that matters most? When Sandy asks what they hope a guest says in the car driving home, both answers come instantly: “That was the best vacation ever — we can’t wait to come back.” As Molly puts it, their repeat guest rate is their number one key driver. In a business built on trust — homeowners trusting them with their family’s home, guests trusting them with their family’s memories — that’s the only scoreboard they need.

Maine Thrive Insights is produced by Smith Digital Solutions, LLC in Bangor, Maine. This Insight is a companion to Maine Thrive Voices, Episode 14 — the first episode of the Community Voices chapter.