After the hustle of buying a home and the bustle of moving, it's common to wonder, now what? At Greylock, we strive to make our part of the process as transparent and simple as possible.

We recently spoke with Greylock member, Kevin Pink, to get his reflections on the process of buying his first home in Pittsfield. Pink, who's nine months into homeownership, has a few insights for anyone considering this major step in their personal and financial journey.

Tell us about your home search.

I was born and raised in Pittsfield and have never imagined living anywhere else. Owning a home has always been the dream, and I was worried that COVID-influenced prices had put the dream out of reach. While I enjoyed living with my longtime roommate, I was conscious that I was paying someone else's mortgage and should think about paying my own instead. I began looking seriously in April of 2025, and purchased my home in early July.

How would you describe the experience?

Real talk - I really didn't love the process of searching for a home. Everything was very expensive and the whole process seemed extremely pushy. Houses were going on the market one day and under contract a day or two later. Every open house was packed with people, and while everyone was friendly, at the end of the day, they're competing with you for a limited commodity. If you win, your prize is being on the hook for hundreds of thousands of dollars for decades.

What I enjoyed was working with my Realtor. She helped me identify my interests and priorities, and she pointed out flaws and opportunities. She also (more than once) talked me off the ledge! Seeing some of the unique homes throughout Pittsfield, including in neighborhoods I'd never been to, was also really enjoyable.

Why did you choose Greylock for your mortgage?

I received the best interest rate at Greylock, but a very important piece of it for me was the stability and longevity of the organization. Most importantly, I was thrilled that Greylock wasn't going to sell the servicing rights to my loan. I have a lot of peace of mind knowing that if ever there is an issue, I can visit a branch and talk to a real person. While that may be atypical among millennials, I prefer in-person interaction to hashing out something important with an anonymous person over the phone or with an AI chatbot.

Was there anything notable about your Greylock experience?

Once the ball got rolling, it was mostly smooth sailing. My mortgage officer, Erin Carlotto, was extremely helpful. She answered all of my questions and encouraged me to apply for a first-time homebuyers grant, which I received!

Describe how you felt during the mortgage process.

The numbers seemed really intimidating at first, but going through Greylock's first-time homebuyers course really helped explain important terms and make sense of how interest would be calculated, what I would owe, etc. The worksheets/forms that I filled out as part of the mortgage process helped greatly to explain the nuances of what is a really complex process!

How did you feel after buying your home?

Like a dog that caught a bus. "NOW what?" Moving was the first hurdle and then figuring out what new furniture and appliances I needed. It's amazing how you can accumulate so many things renting but still feel woefully underprepared for owning a home. For the first several months, it felt a lot like I was just renting in a different place. Except every little noise concerned me that something was wrong!

How do you feel now that you've lived in your home for 9 months?

The first time I put up a curtain rod was my first project as a homeowner - it was also the first time I'd ever put up a curtain rod. Since then, every new project has been some combination of intimidating beforehand and satisfying afterwards. Painting, decorations, furniture, etc. have helped make this feel like my home, instead of just a home I am renting.

What do you wish you had known or understood before buying your first home?

The numbers involved are scary. However, the reward of buying a house isn't just being on the hook for hundreds of thousands of dollars over decades. It's having a place for your friends and family to gather. It's the satisfaction and cold drink after a freshly-mowed lawn. It's meeting your new neighbors and being pleasantly surprised that they're awesome! It's learning home maintenance and repair one project at a time. For me, it's the feeling that I really am part of the community I grew up in and have always wanted to own a home in. It's not easy, but the juice is worth the squeeze.

To learn more about Greylock's free educational resources on topics like homeownership, please visit here.