Andrew Litchfield | 6 Boston Developers to Watch in 2025

NAME: Andrew Litchfield
COMPANY: Penny Investments

You’ve said that 19 was a real inflection point for you. You weren’t a typical college kid like your friends?‍

When I decided to go to college, I only applied to one school—Mass Maritime Academy. I was good at math, wanted to make good money, and thought being an engineer would set me well financially. 

Both my parents had typical 9-to-5’s so an entrepreneurial path wasn’t really on my radar, but then my friend invited me to a real estate seminar. That was the first time I heard about Rich Dad Poor Dad and it changed my whole mindset. The speaker was talking about making money while you sleep and I realized I could make more through rental properties than I would as an engineer.

So I was 19 and all my friends were playing Halo, partying at the weekend, all that stuff, whereas I had a weekend job and was going to networking events. It was funny, I'd come back to the dorm in a suit and tie and my friends would laugh at me.

The first real piece of advice they gave at those events was to meet people who do what you want to do. I told myself, "I don't know much yet, but I'm going to become a master of this." Of course, you don't learn it overnight. You just need to know where you are and where you want to go. That was the inflection point for me.

Was it real estate itself that sparked your interest, or the financial freedom compared to a 9-to-5?‍

It definitely started with financial freedom. I always had this drive to become a millionaire, and that was the hook at first. But as I got into real estate—buying properties, working on them, seeing the before and after—that’s what made me stay. 

You have to enjoy the work, not just chase the money. My passion for real estate has far exceeded what I got into it for initially, the financial side. I love seeing properties and imagining what I could do with them. 

So you’re working, making money, and then diving into real estate through seminars and networking. Did that feel more like work or  fun?‍

Rich Dad Poor Dad really opened my eyes to the difference between working for wages and working for profit. 

The weekend job was fine, I could make anywhere from $18 to $30 an hour—which was great in 2008–2009—but it meant 20-plus hours most weekends. When I went to networking events I realized the earning potential was unlimited. It was about who I could surround myself with.

After the three-day seminar I told my parents, "This is what I'm doing. I'm going to become a millionaire in real estate. I don't want to do engineering anymore." My dad said, "No way." That pushed me to accelerate my degree. I finished in three and a half years because I knew what I wanted.

Those seminars and networking events changed your whole trajectory then?  ‍

Exactly. About six months in I met my first mentor, Daniel Stroe, at a Boston RIA event. He was on a panel and stood out to me because his answers were different. Afterwards I asked him if I could do an internship and he was open to it. 

I interned for him for about a year and a half while finishing school and learned so much. I was checking on job sites, doing Home Depot runs to get whatever the contractors needed, and helping Daniel analyze deals. He’d hand me a list of properties and tell me to budget them out and figure out what we should pay. That was invaluable. I saw firsthand what worked and what didn’t without losing my own money.

We’d talk about the construction side, then I’d help with funding and financing—how you secure the money—and then marketing. I put together email campaigns and direct mail for him. He’d never had interns or anyone working for him, but learning all that stuff meant I could buy my first property in 2011, right after graduating.

That’s an incredible education to get at that age. So you bought your first property at 21 on the back of that?‍

Correct. January 12, 2011. I found a two-family listed at $42,000. For the first ten days, only owner-occupiers could bid, which worked for me since I planned to live there.

I put all my $10,000 savings down and borrowed the rest on hard money. Bought it for $44,000, then spent $25,000 renovating both units—a three-bedroom and a one-bedroom.

The plan was buy, renovate, rent, and refinance. Before I even knew there was a name for it—the BRRRR method—I was doing it. Six months later, I refinanced, paid off the lender, kept a little cash, and moved into the one-bed unit. My new mortgage payment was $530 a month and the three-bedroom made $1,100. So I was living for free and making an extra $570 every month.

That really solidified what was possible. Even if flips weren’t steady income, I knew I had $500-plus net each month after the mortgage.

That first one helps what you realize is possible—tell me about the second and third ones, how did it grow from there?‍

The second was another win. About a year later I found another two-family in Webster. I did the same thing—renovated, refinanced, rented. I lived in one and rented the other.

Then I got too ambitious with deal three. I told Daniel I could do a flip on my own. He asked, “You sure?” I said yes and then lost money. I had to sell one of my two-families to cover the loss. The rentals went great, but the flip—without Daniel behind me—lost money.

I realized I needed steady income for a while so from about age 23 to 26 I got a full-time job in the energy sector working 40–50 hours a week. I met the owner at a party, I was the second employee. He needed an operations guy and was flexible with my schedule, so I could keep doing real estate on the side.

I stayed longer than I wanted because there was a shiny object at the end because the company planned to sell. In the end, the equity I was supposed to get never came through. It took me a while to move on. I took a trip to Peru and came back and decided to quit and go full-time real estate.

Were you still doing deals at that time or just resetting before charging ahead?‍

Right before Peru I bought a single-family in Dorchester. Friends lived in South Boston and Dorchester, and I knew there was more money in the city. We made about $60k on that one, I split it, so about $30k to me. I went to Peru, came back, and thought, “What am I doing at this job? It’s holding me back.” 

I gave notice and then started the next chapter, which was a partnership with two good friends—Anthony and Ryan—and we started Rock Development. 

And did that feel like a natural progression?‍

It did, but we definitely learned a few things along the way. We focused on image instead of income and in hindsight, our overhead was too high for a start-up. We got an office on East Broadway and hired an office manager, a purchasing manager, a project manager—it was a lot. 

Another lesson was that we didn’t need to do every project. We had about ten triple-deckers in South Boston and Dorchester at once, each with $300k–$500k renovations. And we’d never done this before.

We divided roles: Anthony took construction because he’d worked with his uncle as a laborer, I handled financing and investors, Ryan did acquisitions. We felt good until we were stretched. Ryan kept buying and I said, “We can’t buy more.” If we’d wholesaled a few and focused on executing the rest, we might still be together. You live and learn.

Partnerships can be a really hard thing to navigate. What advice would you give to others on a similar path?‍

Start partnerships on a deal-by-deal basis. See how it works. People want to start a company with a friend before they’ve done a single project together. Set expectations. See you’ll handle it if things go wrong. Do they blame, or do they problem-solve? 

Also look at lifestyle, not just business. A year in, I met my now-wife and became a stepdad to two kids—one and five. My priorities shifted. I cut the BS: no long lunch meetings, grab something and get back to work. 

I feel like the best partnerships often share similar lifestyles and understand each other’s obligations. If one person is up at six working and the other is out every night, there’ll be friction.

Love the advice—do the first project together, maybe the second, before formalizing a business.‍

Exactly. It’s hard to keep everyone equal. And roles must be complementary. If you’re on site managing construction, the other person should run the back office. Lastly, there can usually be only one visionary. With me, Ryan, and Anthony, we all had our own egos and ideas. Better to focus, execute, then expand once the engine runs without you.

How long did Rock run?‍

About three years and then we decided to part ways. We still had eight projects together, so we had to wind down and stay on good terms—all while trying to make our own money. It could’ve been ugly, but it stayed professional.

Ryan’s running his brokerage and crushing it. Funny enough, Anthony and I still co-own about half my rentals and have projects together. We’ve been through a lot, and we’ve learned. When we partner now, if I bring him a deal and want him to run construction it’s 50/50 and he handles everything. He gets a management fee, but he’s not just looking at it as a GC—he’s a partner and a developer on the deal too.

A graceful exit, then. And you now run Penny Investments—did you start that right after Rock?‍

Well I hadn’t fully learned my partnership lesson yet. I often felt I needed someone else to help spread risk. In 2019, as Rock wound down, I started Penny Investments with Steve Suda. 

He’d been working on acquisitions with us. We aligned a lot. We didn’t do many projects until COVID and that obviously changed things—a lot of people paused. I still had to feed my family and managed to make around $300k off this one great deal I found, which made me realize I could do it on my own. 

Boston’s a small city though. I don’t burn bridges. Steve and I kept a good relationship. He agreed I should keep Penny and he moved on to Avenue Capital with his partner, Luke, and they’re doing great. So by the end of 2020 I became the sole owner of Penny Investments and that’s what I’ve been focused on, alongside coaching.

So you fly solo, how did you get comfortable with construction and development? Is it about working with good people, having processes?‍

For me a lot of it was down to experience and the repetition of analyzing deals.

My coaching students will ask, “How do you know what a roof will cost?” I build spreadsheets—e.g., for a 1,500 sq ft single-family, here’s a typical roof cost—but you never truly know until you’re in it. You learn by writing the checks, finding something behind the walls, and understanding what it costs to fix.

People might find a deal and say, “We’ll make 40 grand—I’d be happy with that.” But that forty can disappear fast: $20k more in construction, $20k less on the sale. It’s that simple. So it comes down to repetition—walking properties, seeing the issues—and having someone you can bounce deals off.

And now you’ve scaled the number of projects, you’re obviously comfortable on the construction side? How is that happening?‍

I run about 15–20 jobs at a time with Penny. I have a full-time project manager, an assistant PM who also does acquisitions, and an operations person.

When I hired my PM in 2020, he didn’t have tons of PM or construction experience, but I taught him the way I’d been doing things myself. Sometimes people hire from big firms and they’re set in their ways, but what I looked for first was attitude and mindset. One morning I asked him to check a property—by 7:30am he’d been, called with an update, and asked what’s next. That told me he had the drive.

It also helps that I’ve got my GC license. I can’t swing a hammer—ask my wife—but I know how it’s done. On my second rental I discovered knob-and-tube wiring and my electrician said, “I’ll charge hourly, you can be my helper.” I literally rewired the whole house with him. Now I know where the wires go, what holes to make, and roughly how long it takes. 

That understanding helps you negotiate with contractors. If someone quotes $15k and materials are $3k, that’s $12k labor—if it’s a three-day job, that sounds off. I’m not doing the work, but I understand what it takes.

You can’t replace that experience. What about back-office, have you had to evolve and professionalize that side of things?‍

Yeah that’s important too. A big thing for me was finding decent project-management software. We use Buildertrend. Like any tool, it’s only as good as your implementation. I’m not great at that so my operations manager handles it. But now I get daily logs for each project—what happened, issues, fixes, photos, videos—and can visit the city once a week because I want to see the properties, not because I have to.

Shifting gears, you’re big into mentoring. Beyond your own mentor experience, what sparked that drive to help others?‍

Early on I realized the willingness of people in real estate to help others and that’s a really big thing for me. 

I started coaching later than I should have because I didn’t feel “ready”. But throughout my journey I loved helping people, and people kept asking how I was doing things. Over the years I’ve informally mentored multiple developers—Centreline Development, Adam Jaspen, Ian Martin at Baseline—who are crushing it now. 

Eventually I thought, “What am I waiting for?” I put a story on Instagram, “Hey I’m looking for motivated people who want to learn real-estate development”. About 40 people replied. I filled 10 spots the first time. The next round wasn’t as easy, but that first intake worked really well. 

And is your approach unique to what others offer?‍

I believe that being a great mentor isn’t only teaching real estate—it’s mindset, resilience and personal development. Like we said earlier, things will go wrong, but it’s how you respond that matters. I’ve been through a lot, learned a lot and have a lot of helpful advice to share. 

What’s that experience been like, putting your ideas and experience down on paper?‍

It's shown I have more to share than expected. Going back to when I was 19–20, Rich Dad Poor Dad kicked off my personal development—motivational speakers, lots of books. Building the coaching course showed me how much it helped me, and teaching it showed how much it helps others. The law of attraction is a big thing for me. We attract what we're intentional about.

So paint a picture for prospective students: numbers, results, what to expect?‍

We started in early '23. I run three groups a year, roughly 10 people each, so about 65 students so far. I keep cohorts small so I can be accessible.

Roughly 40–45 of my students have done deals, some multiple. My star student, Julian, wholesaled three deals—made about £80k—then we flipped a single-family together in Jamaica Plain and netted ~£220k. We've got a six-unit together now and he bought a three-family with another student. He still has a full-time job as a mortgage broker, it’s so impressive what he’s doing.

I teach everything from scratch: finding deals, analyzing them, financing—hard money, bank financing—then raising capital. Then condo conversions and the BRRRR strategy for rentals.

One of my favorite topics is zoning in Boston. I've handled about 50 zoning projects—most myself, without a zoning attorney. I’m not saying never use one, in some areas you should, but doing it yourself can save $10–20k. 

The general info exists out there—BiggerPockets, books—but Massachusetts specifics are harder to find. I've got my GC license, my PM's license, and we know the city processes. I'm not going to claim I can help in Arizona—that's not my market. I stick to what I know and I think my students appreciate that. 

Are students finding deals so you can apply lessons live, or do they complete the course and then apply it?‍

I run eight weeks of course content plus six months of individual follow-up calls. The eight weeks are group Zooms plus property site visits. There are outliers—one of my first students found his first deal in three weeks and made $160k. But ideally, we use those eight weeks to learn.

The first follow-up call is like, "Think forward a year—what do you want to have accomplished?" Most say flip one property or buy one rental, so we work backwards. A flip takes six months, so you've got four to five months to find the deal. If I find a deal in their area, they're the first I call.

For partnerships: say I find a deal at $380k. I might bring it to a student at $400k. We need to raise £100k, partner 50/50. If they can't run it, I manage it for 10%, they learn the process, then we split profits. Students do their first deal, make money, want to do it again.

Do you ever worry Boston becomes zero-sum—lots of aspiring developers you’re connected with, plus your own deals? Or is the market big enough that it’s not a concern?‍

I have an abundance mindset—that's week one of the course. You meet people who say, "I've got a deal but can't share the address." That's scarcity. I've got 15 deals going; I don't need to steal yours.

A lot of my deals come through probate. Why do I get them and others don't? Timing and mindset. Go after it with expertise. I'm a big believer in abundance. There are enough deals for everyone if your mindset's right.

Can you touch on the philanthropy side?‍

Absolutely. Giving is an integral part of my life. Andrew Carnegie said something that’s stuck with me: "I'll spend the first half of my life making my fortune and the second half giving it away." That drives me—family first, but I want to flip from 80% work/20% giving to the reverse.

At 21–22, I joined a youth non-profit in Providence—Young Voices—and found real fulfillment seeing young people learn public speaking and advocacy. I served on the board for seven or eight years.

Then when my work shifted to Boston, I joined Silver Lining Mentoring. I became a mentor to Armani, now 21 at Suffolk University—amazing kid. About a year in, they asked me to join the board.

I work with my wife too. She has a huge heart and said, "Can you find a building for single mothers?" So I'm working on a domestic-violence women and children's shelter in Medford. I also partner with organizations across my rentals, like Children's Services of Roxbury and Justice for Housing. The latter help formerly incarcerated people secure housing—you don't realize how hard housing is with a record so I’m passionate about helping there.

I once bought from a slumlord in 2017–18. Constant repairs, poor conditions. I decided that for every rental I buy, I'll BRRRR and deliver quality living conditions for people at fair rates. 

Now it's almost a game: how much can I give this year to good causes that multiply impact? I set my giving goal before my earnings goal.

Very cool. What do your parents think—coming from nine-to-fives, success in engineering—about your path?‍

I think they’re amazed and proud now. At 19–25 they were cautious—“We’ll let him try.” When I said, “I’m going to be a millionaire,” it was, “Okay, Andrew.” They're now retiring and are my biggest supporters. They see my videos and share them with family. 

Early on they were just worried I might fall on my face. Now they ask for real estate advice. They probably still think I’m a bit crazy with the scale. I’ll say, “I’ll be into this for three million, worth five, collecting 30,000 a month,” and my dad's like, “What the…?” But they trust me.

And you’re a parent yourself, how do you balance all this with being a dad

‍Family is number one. I’m about to have my fourth baby. Our youngest is almost seven, and we tried for four years. Early on I was wishing for a girl, but now it doesn’t matter—we’re having a boy and I’m just grateful. I know it’s hard for a lot of people to have kids so it’s important I share our story as well.. I want to keep traveling with them and making memories. We took our first trip to Europe this year—London, Paris, Amsterdam—and it was awesome, I want more of that.

Finally, you mentioned flipping the 80/20 earn/give. What haven’t you done yet that you want to—personally or professionally?‍

First of all, I want to make money, give back, and create memories with my family. That’s the main thing.

Business-wise, I’ve got a solid rental base and want to trade three- and six-families up into larger buildings—more under one roof. I want to reach the point where the cash flow truly supports itself and I don’t need to chase deals to keep the lights on.

I also love teaching. I don’t know exactly where it evolves, but building the student network and platform will be huge. I want more collaboration with students. Long term, I’d like to buy in Puerto Rico—my wife’s from there and we go often.

Overall I like to leave some of the future open. Focus on the right day-to-day mindset and stay open to what comes.

Andrew, thank you for your time and good luck with everything, that was incredibly inspiring!

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