The Pricing Menu: How My Dog-Sitting Business Taught Me About Setting Prices

Let’s backtrack to 2018, when I started my dog-sitting business in Boston and had absolutely no idea how to price my dog boarding and dog daycare services. I’ll be honest: I just picked a number that felt fair, $20 a night. That was it.
No strategy, no research on the market around me. I just wanted people to try my service and trust me with their most precious belonging: their loving dogs. As an entrepreneur undergrad, this was unexpected of me,
but because of my desire to form part of the industry I just jumped in with what I thought was best at the time, winging it but playing it fair. However, as the years went by, little by little, things changed.
My demand increased, I got busier. My weekends, vacations (even birthdays!) were fully booked with dogs. Even though I couldn't have been any happier to have all those dogs with me,
I realized something: TIME IS MONEY.
I wasn’t just “watching” dogs anymore. I was becoming their home-away-from-home,
loving them like my own, keeping them safe and sound, sending photo and video updates, following feeding and potty routines, giving meds when needed. It was real work, dedication and
I learned a very important lesson: my time, my experience, and the trust I was building had SO MUCH value.
Fast forward 4 years, after years of experience and adaptation to the market and setting,
boarding a dog at my place was $60 a night. Same house, same me but now my clientele significantly grew over 400+ clients, the demand for my service was higher and my space was still limited.
And you know what? My best clients stayed because they believed in my value. They got me!
Why People Pay More Than Just the Price

 That’s when it hit me: people don’t pay for the “thing” you sell. They pay for how it makes them feel. Starbucks doesn’t sell a $6 coffee because the beans have a high cost. It sells the moment, the comfort, the status boost of walking around with that starbucks cup. Or take Tiffany, they charge hundreds if not thousands for silver jewelry because it’s the classic, luxury, high-status Tiffany & Co.

The price isn’t just about materials, it’s about what the brand represents. Of course for me, dog owners weren’t just paying for my service of dog boarding. They were paying for the peace of mind that I was able to provide for them (and their dogs). They knew their dog was safe, loved, and treated just like family. That’s worth more than the cheapest option in town, and they all knew it.
How I Raised Prices Without Losing Customers

When I started my business, I kept prices low to get my name out to Boston dog parents.
That’s called penetration pricing: start low price, attract clients, then grow from there.
As my service demand grew, I slowly raised prices for new clients
while keeping loyal ones close to their original rates. This way, I was able to reward the clients
who stayed loyal and believed in me early on in my career while moving my business toward
what it was really worth. Concerts, Broadway, Airlines and others do this all the time.
Early bird prices, loyalty perks, higher rates for last-minute or over-the-holiday bookings.
Does it work? Oh, yes.

Because when people see the value, they stay. Pricing Isn’t Math. It’s Psychology.

Here’s what I learned from four years of trial and error:

1.
 Start low if you need to, but don’t stay there. Time is money.
2. People pay for how you make them feel. Safety, trust, status, those are the pillars.
3. Don’t fear growth and reward loyalty. Old customers stay when they (also) feel valued.
4. Context and setting matters. Pricing isn’t one-size-fits-all.
5. Your price tells a story about your brand. Make sure it matches the level of experience.

Topic: Understanding Pricing / Setting + Adapting Price

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