A Name to Know with Rob Natale

MEET BostonMan Magazine Legacy Club Member Rob Natale! Rob joined our Legacy Club Professional Networking Community in January 2024, has made a huge impact on our group both with his company, North Square Capital, and his friendly and selfless demeanor as a community leader.

Recently we sat down with Rob and got to know him a little bit better. He is certainly a NAME TO KNOW both with BostonMan and throughout the city!

BMM: Thanks for joining us for this edition of A Name to Know, Rob. Could you quickly give the readers a quick introduction to yourself?

RN: I was born and raised in Sharon, Massachusetts, about 30 minutes south of Boston, with my parents and two sisters, one of whom is my twin (I’m a minute older).

I attended the University of Rhode Island, where I majored in Finance. I made many great friends there and still keep in touch with many of them today. I love the beach, and URI’s off-campus housing is right on the water, which was a huge plus. Soon after college, I moved to the North End of Boston, where I’ve lived for 14+ years.

Family is very important to me, and I have three awesome little nieces I try to see as much as possible.

Here are some fun facts about myself: I make homemade wine with my family every September and have been making it for 30 years. It’s a Super Tuscan Blend: 2/3 Sangiovese and 1/3 Cabernet. My high school superlative was ‘Most Huggable.’ I’m a 54 handicap in golf. I love food.

BMM: Your company, North Square Capital, has a unique approach to investing. What led you to start this venture?

RN: For several years, I was deeply entrenched in the world of Wall Street. My days were filled with working alongside financial advisors, promoting investment products like mutual funds, ETFs, College 529 plans, and more. Some of these advisors and their teams managed substantial assets, surpassing the $3 billion mark.

However, I couldn’t help but notice that these highly successful teams operated in isolation, utilizing strategies that 90% of the population didn’t even know existed. It felt like a good ol’ boys club.

Let’s contrast this with the medical industry. If a new discovery is made, this information is disseminated to the masses for the betterment of all. Collaboration and sharing information has been at the core of its existence.

This stark contrast made me reevaluate my career path, eventually leading me to where I am today.

I come from a family where several relatives dedicated their lives to medicine. I witnessed their unwavering dedication, tireless efforts to care for their patients, and selfless nature, always putting others’ needs before their own.

However, I also saw the toll it took on them – exhaustion, burnout, and overwhelming stress. Work-life balance was a luxury they couldn’t afford. On top of it all, I saw how the financial services industry poorly served them.

A lightbulb went off for me – I knew what I needed to do.

I started North Square Capital to provide stable, tax-advantaged real estate investments to medical professionals and those with demanding careers. Through passive real estate investing with no time commitment, they can build wealth, buy back their time, and retire on their terms.

BMM: As a member of BostonMan Magazine’s Legacy Club, you are clearly a big believer in community. In fact, you are also the Boston URI Alumni Network Leader. Tell us a little bit about what this entails and what it’s like holding events with other professionals from your university.

RN: More than 15,000 URI alumni live in the greater Boston area, but we currently have a dormant network. I’m looking to change that. This past April, I collaborated with URI’s Alumni Engagement Department to help organize a network relaunch at Night Shift Brewing at the Garden. Close to 40 people showed up, all expressing excitement about having a local URI chapter.

We plan to host another event in July, aiming to start with quarterly in-person events.

I also recently created a LinkedIn Group where you can network with fellow URI alumni, share experiences and insights, offer and receive mentorship and support, discover professional opportunities, and more.

A great book by Keith Ferrazzi, “Never Eat Alone,” reminds us that the genuine desire to help others succeed is at the heart of every successful relationship. I highly recommend it to those who have not read it.

BMM: You are a proud resident of Boston’s Little Italy in the North End. What are the things you like most about living in ‘America’s most beloved neighborhood’?

RN: I love living in the North End. This has been my home for the past 14 years, and I could talk endlessly about why I think it’s the best neighborhood in the city.

Living in the North End puts you right in the heart of Boston. You can walk to the Garden area, downtown, Faneuil Hall, Christopher Columbus Park, and the Seaport. You’re right on the Greenway, with close access to North and South Station and all four subway lines. Despite being in the center of the action, the North End still has that rare, cherished neighborhood feel.

Being 100% Italian, I have a special connection to this neighborhood. The abundance of great restaurants, bakeries, and Italian grocery stores makes it feel like a slice of Europe in Boston.

Let me share a quick story: Back in 2021, when Italy was playing England in the Europe Cup Final, the neighborhood was buzzing with excitement. All the bars and restaurants were filled with people having a fantastic time. When Italy won in penalty kicks, the celebration spilled into the streets. Hanover Street became a block party, shutting down to car traffic as everyone joined the celebration. It was a timeless moment that truly captured the spirit of the North End, and a great memory.

BMM: 2024 has been off to a big start for you. What do you have planned for the 2nd half of the year, both professionally and personally?

RN: Many exciting things are on the horizon right now.

Professionally, I’m offering two unique investment opportunities to help my clients get closer to their financial goals.

One is a real estate income fund, perfect for the cash portion of their overall investment portfolio. This investment pays between 8% and 9%, with the option to take monthly distributions or let it sit in the fund and compound—where the real magic happens. It comes with 90-day liquidity, typically averaging 30-45 days, offering a great way to earn a good yield on money while retaining access if needed.

The other opportunity is in a Short-Term Rental Portfolio made up of over 65 properties. This investment is geared toward the 30% of one’s portfolio that should be invested in assets not correlated to the stock market, like real estate.  This strategy provides excellent cash flow, appreciation, and tax benefits. Although it has a longer hold period of 3-5 years, making it a buy-and-hold approach, it still offers quarterly cash flow distributions between 7% and 9% during the investment period.

Additionally, I plan to continue growing and expanding the URI alumni network, attend real estate events and conferences, and host monthly webinars.

On the personal side, I’m aiming to get more involved with Community Servings by working towards joining their young advisor’s board. This Boston-based non-profit provides scratch-made, medically tailored meals to individuals and families facing critical or chronic illness and nutrition insecurity in Massachusetts and Rhode Island. Their mission, “Food is medicine. Food heals,” resonates with me deeply as someone who believes in the power of food and health.

I’m also looking forward to a week in July on the Cape with my family, a tradition I look forward to every summer, and always a lot of fun.

Additionally, I have a couple of friends’ weddings this summer all across the country, from Massachusetts to California to Hawaii, so I’ll be logging a lot of miles in the air.

Overall, the second half of 2024 promises to be very exciting, both professionally and personally!