Romulus Capital, a Cambridge-based venture capital firm founded in 2008 out of MIT, recently announced it raised its third fund of $75 million, bringing its total assets to $150 million. And even though Romulus, which invests in seed-stage companies, has become one of the fastest growing firms in Boston, the team of under-30-year-olds has had to work the grindstone over the past several years to do so.

In fact, you can just ask one of its portfolio companies, real estate tech company Placester, what it’s really been like working with Romulus as it’s built itself up. At least that’s what we did.

We spoke with Placester’s co-founder and CEO, Matt Barba, to hear an unvarnished account of what it was like being a 20-something, first-time entrepreneur working with a 20-something, first-time VC.

Matt Barba. File photo.

Barba was introduced to Krishna Gupta, founder of Romulus Capital, by Ginger.io, a startup that had been in the same 2011 Techstars cohort as Placester. In 2013, Romulus led Placester’s $2.5 million seed round. And right off the bat, Barba recognized the distinct dynamics he was going to experience with Gupta.

“I think there are tons of investors that throw money out and then never talk to you again,” Barba explained. “Then, there’s the opposite: The ones who are overbearing. Who you look for depends on the kind of company you want to build… From the start, Krishna wanted to build a relationship, wanted to be plugged in. At least I can say he wasn’t one of those complete nightmare investors.”

With that said, because Gupta was engaged and opinionated with regards to the company’s decision-making process, the then-novice entrepreneur was thrown into a crash course in investor relations.

“It’s a delicate dance when you’re dealing with that type of rapport. I learned you have to strike a balance of telling them enough, but not too much, about what’s going on in your company,” Barba said.

What’s more, he shared it hasn’t always been rainbows and butterflies. Any disputes he’s had with Romulus have been filled with mutual respect and have ultimately panned out to be constructive. But fighting has occurred over the past few years. A lot.

“We have fought, I would say, regularly,” Barba said. “He’s shown himself to not take things personally, so we’ve been able to express our own side of an argument and not have it permanently taint the relationship.”

We have fought, I would say, regularly

Gupta supported Barba’s account, chalking it up to them sharing similar personality traits. Although, Gupta claims his extroverted nature generally comes off as more forceful than Barba’s introverted manner. The VC explained:

If you ask a lot of entrepreneurs, they’ll tell you I’m very aggressive. I push back hard. I have conviction… I also like to see when people push back. I relish the argument, and Matt is someone who will take what you say, think about it for a while and then come back and say ‘I disagree.’ I love that… There are times when I won and times when he won, but we’ve managed to work well together even though we’ve had plenty of times when we’ve disagreed.

He and Barba also agree that the fact they were both building up their respected businesses when they were young offered its benefits. Gupta told us he has essentially grown up with Matt the past several years and has used him as a sounding board for his firm.

Meanwhile, Barba shared there have been pros and cons of pairing a young entrepreneur with a young investor:

I’d say a pro of us being the same age is that we’re both exploring through similar perspectives, which can be a big positive. But the contrast is that there’s something to be said about experience, and Krishna acknowledges that… When I met him, I had no idea what a VC should look like, so it didn’t occur to me that he was young.

Experience or not, it’s been working out for both Romulus and Placester. In addition to Romulus successful fundraising, Placester has cleaned up in its own right. It’s closed three rounds of funding since its seed, the most recent of which was its $27 million Series C in November 2015, of which Romulus was also a part. With those changes, the dynamics between the VC and startup have changed – kind of like a couple who has become comfortable with one another after the initial wave of passion has started to calm.

“Placester has matured a lot as a business, so things are different now,” Barba expressed. “There are still things we disagree about, but they’re smaller because the pillars of our company are already set. Krishna is on the board now, so that formality has crept in… Normally, once company ventures out of the strike zone, investors back off, but he’s stayed present.”

So do they still get into disputes? You betcha.

“Even today,” Barba said. “I think that’s healthy, though.”