The Hidden Cost of Remote Work: Why Early-Career Professionals Need to Be in the Room

Over the past decade, I’ve worked with many young adults transitioning from college to the workforce. More and more, I hear the same thing: they’re struggling with career direction. They’re unsure of what path to take, what roles fit their skills, and how to build a meaningful career.

This has always been a challenge, but the rise of remote work has made it even harder. While Zoom and Slack provide flexibility, they also remove something critical for early-career professionals: exposure.

When starting out, you don’t know what you don’t know. You might think you understand what a marketing analyst or product manager does, but until you see it firsthand, you won’t know if it’s the right fit.

In an office, exposure happens organically:
- You overhear a senior colleague negotiating a deal and realize sales excites you.
- You see how a project manager runs a complex launch and discover a hidden talent for operations.
- You sit in a meeting, hear finance asking the sharpest questions, and suddenly find the field interesting.

These moments shape career paths—but they rarely happen when you’re just a box on a Zoom screen.

Beyond exposure, being in an office helps in four key ways:

1. Serendipitous Learning
Some of the best lessons come from hallway conversations, coffee chats, and observing experienced colleagues. These unplanned learning moments disappear in a remote setting.

2. Building Real Relationships - Networking isn’t just about LinkedIn. It’s about the bonds formed over time—grabbing lunch with a colleague, jumping in on a project, or chatting with your boss beyond the weekly meeting. These connections lead to mentorship and job opportunities.

3. Unscripted Opportunities - Being present means getting pulled into meetings, volunteering for projects, and catching the attention of senior leaders. Remote workers often miss these organic chances to prove themselves.

4. Understanding Workplace Dynamics - Every company has unspoken rules and power structures. Knowing how decisions are made and who influences them is crucial for career growth—and far easier to grasp in person.

Remote work has its advantages, but for those just starting out, nothing beats being in the room. Show up. Observe. Ask questions. Get involved. You’ll learn more than you ever could through a screen.

Written by Jeffrey Silverman

Early-Stage Investing: Like Your First High School Relationship

At a VC dinner a few weeks ago, one of my closest and oldest VC friends (even though she’s MUCH younger & smarter than me) told the room about the first time we met. She laughed as she recalled how I compared the relationship between an early-stage investor and a first-time founder to your first high school relationship.

At first, the room chuckled. But the more we unpacked it, the more it resonated. Because let’s be honest—first-time founders and early-stage investors go through the same emotional rollercoaster as two teenagers navigating their first serious relationship.

We start with the courtship, aka, the pitch process. Remember the nerves before asking someone out in high school? The overanalyzing, the rehearsed lines, the silent hope that they’d say yes? That’s a first-time founder walking into their first VC pitch.

The founder is trying to say all the right things, put their best foot forward, and prove they’re worth the commitment. Meanwhile, the investor is sizing them up—do they have potential? Do they have staying power? Do they seem like someone they’d want to be in a long-term relationship with?

And just like in high school, sometimes the biggest mistake is trying too hard to be what you think the other person wants instead of just being yourself.

We enter the honeymoon phase – once the investor commits, it’s all excitement. The founder feels validated, the investor feels like they got in early on something special, and both sides are optimistic about the future.

During this phase, everything is going right. Revenue is up! Growth is happening! The founder is sending updates full of good news!

Just like that high school relationship where you’re convinced, this is it.

Life is not all roses –reality sets in. Things start to get hard. Customers push back, product issues arise, hiring is tough, and revenue projections miss the mark. Suddenly, the investor—who was all praise a few months ago—has questions.

What’s the plan? Why isn’t growth faster? Do you need to make some tough calls?

It’s like the first big fight in a high school relationship. Do you communicate and work through it? Or do you start to resent each other?

Every successful relationship is built on trust and communication. If the only updates an investor gets are when things are going great—or worse, if the founder ghosts them when things go wrong—trust erodes.

It’s like in high school for the digital native generation (note passing for others) when someone just stops texting back. You’re left wondering, Did I say something wrong? Are they okay? Should I reach out, or do I wait for them?

The best founders, like the best partners, keep the lines of communication open—especially when things aren’t perfect.

But even when things go well, relationships drift.

Just like in high school, where you and your first love swear you’ll always stay close—but then college happens, new experiences happen, and life pulls you in different directions—the same thing happens with founders and early-stage investors.

A few years in, the founder raises their Series A, and the new investors take center stage. The founder’s priorities shift, they have a bigger team, bigger challenges, and bigger expectations. The seed investor, who once got every update and every late-night call, now gets a quarterly email and the occasional “Hope you’re doing well!” text.

It’s not personal. It’s just life.

And eventually, as the company scales, that once all-consuming founder-investor relationship fades into a distant memory—one you both look back on fondly but know was just a chapter in a much longer story.

At the same time, not every relationship works out nor is every company successful. Sometimes, an investor who seemed great at the start turns out not to be the right fit. Sometimes, a founder pivots in a direction that makes sense for the business but not for the investor. And sometimes, external forces—competition, market downturns, bad timing—force a breakup.

And like a high school breakup, some end amicably, and others… not so much. The best ones end with mutual respect, keeping the door open for future opportunities. The worst ones leave baggage that follows you for years.

Every investor has the one that got away—the company they could have backed but didn’t. And every founder has the investor they should have chosen but didn’t.

At the end of the day, the best founder-investor relationships—like the best high school relationships—are built on honesty, mutual respect, and the ability to grow together.

Some will last, some won’t, but all of them teach you something for the next one.

Next time, we’ll dive into the first date—aka the pitch meeting. Because just like in high school, getting the first meeting is one thing. Nailing it? That’s a whole different challenge.

Written by Jeffrey Silverman

Why Raising Fund 2 Was Harder Than Fund 1

This is part 4 of 10 of our 10 Years of Laconia Series.

When we raised Fund 1, it was fueled by the trust and camaraderie of friends and former colleagues. These were people who had seen David and me in action, knew our work ethic, and were willing to take a chance on us as we transitioned from angel investors to venture capitalists. For that, we will forever be grateful. But fast forward two years, and we were back in front of these same LPs, this time asking them to take another swing—not just because they trusted us personally, but because they believed in the vision we had for Laconia.

Fund 2 was the inflection point that meant we were all-in. By the time we began raising it, we had brought on Geri as our third partner and were ready to scale and grow a truly special venture firm. But there was a big hurdle: Fund 1 was still in its early days, and venture funds take time to show results. While we had a few markups in Fund 1, it wasn’t enough to point to a proven track record. Asking Fund 1 LPs to reinvest without fully realized results was daunting.

It’s worth noting that we returned Fund 1’s initial capital within those first four years (and have since returned more). This performance underscores the strength of the companies we backed and the value we’ve created for investors, even in the early stages of building Laconia.

To their credit, 85% of our Fund 1 LPs came back in for Fund 2. That kind of loyalty and trust is rare and speaks volumes about the caliber of people who believed in us from the beginning. But even with that vote of confidence, we needed to expand our LP base to build momentum. And that’s where the real challenge began.

David and I are not natural self-promoters. The fundraising process for Fund 2 required us to stretch beyond our comfort zones. Networking became our daily reality. We leaned heavily on referrals and spent countless hours explaining our vision and strategy to potential LPs who had no prior history with us. This wasn’t just about pitching a fund; it was about selling the long-term vision for Laconia and the value we could bring as a concentrated, boutique venture firm focused on pre-seed and seed-stage B2B companies.

Through grit, determination, and a lot of late nights, we secured $13 million for Fund 2. By some measures, that’s not a large fund. But for us, it was significant. We’re a concentrated firm by design, intentionally working closely with fewer companies. Fund 2 allowed us to double down on our thesis and continue building something unique in the venture ecosystem.

Raising Fund 2 taught us that being a good investor is only part of the job. Building a venture firm requires a strong LP pipeline, constant relationship-building, and the ability to communicate your vision in a way that resonates with others. It’s not easy, and it’s not natural for everyone. But for David, Geri, and me, it became an essential part of growing Laconia into the firm it is today and will be as we enter the next decade. 

Looking back, Fund 2 was harder than Fund 1 in every way. But the challenges we faced during that time laid the foundation for everything that followed. And for that, we’re deeply grateful.

Jeffrey Silverman

How We Met Geri – Another Serendipitous Moment

This is part 3 of 10 of our 10 Years of Laconia series.

There’s something funny about serendipity – you never know when it’s going to raise its head. In building Laconia, we’ve experienced more than our fair share of these moments. One of the best examples? Meeting Geri Kirilova.

It was a cold and wet Monday night in the fall of 2015. One of our LPs was celebrating her 50th birthday at an Irish pub in the Financial District. I’ll be honest: I wasn’t exactly thrilled about going. It was miserable outside, I lived uptown, and the thought of schlepping downtown was far from enticing. But this person meant a lot to me, and I couldn’t miss the chance to give her a big birthday hug. (Yes, I’m a hugger.) So, I pulled on my coat, hopped on the 6 train, and off I went.

The party was on the second floor of the pub. I climbed the stairs, and as I reached the top, I bumped into an industry peer. Standing next to him was a young woman with wild hair – the kind of hair you don’t forget. We exchanged quick small talk, and I learned she was a senior at NYU Stern. It was one of those blink-and-you-miss-it moments – maybe a minute with the peer and 30 seconds with the young woman before I moved on. I made my way through the room, doing my rounds: hug, kiss, hug, kiss. Thirty minutes later, I was back on the 6 train, headed uptown, thinking little of it.

A few weeks later, David and I were having a working lunch. We were tossing around the idea of bringing on an intern – yes, a paid intern – to help us with some projects. And out of nowhere, I thought of the young woman I’d met that rainy night. I told David, “I met this young lady at a birthday party. She made a strong first impression.” That was it. We decided to reach out.

Fast forward: That young woman was Geri Kirilova. Today, Geri is our third pillar and Laconia, our LPs, and the founders we support are all better off because of her. What started as a brief, forgettable moment at an Irish pub turned into one of the most serendipitous decisions we ever made.

Geri’s growth from intern to Partner has been nothing short of extraordinary. Her tenacity, judgment, and keen understanding of early-stage investing have played a critical role in shaping Laconia into what it is today. 

As for serendipity? Sometimes you just have to take the 6 train on a rainy night, climb the stairs, and say hello.

Jeffrey Silverman