Treat Your First Investor Meeting Like a First Date – 2024 Update

In 2015, as I was starting Laconia after five years of being an angel investor, I wrote this blog comparing a first pitch meeting with a VC to a first date. The parallels are uncanny—from the nervous anticipation to the delicate balance of making a great first impression without overdoing it. Now, as Laconia celebrates its 10th year, I pulled the blog back up, and it still holds true today. I decided to slightly update it and republish it—let me know if you disagree.

A warm introduction has been made. You’ve been wanting to meet this investor for a while, and now it’s finally happening. Thanks to the internet, you dive deep into your research. You check out their LinkedIn, scroll through their tweets, read their blog posts, listen to their podcast appearances, and see what deals they’ve done recently. The sheer amount of information can feel overwhelming, but being prepared is non-negotiable.

Everyone feels a little nervous before a first date—or in this case, a first investor meeting. It all starts with how you present yourself. You want to strike the right balance between professional and approachable. The last thing you want is to walk into the meeting feeling either over or underdressed. Read the room before you enter it.

On the way to the meeting, your mind is racing. How do you kick things off? Do you break the ice with small talk? What if they’re not a sports fan, or they don’t care about the latest tech trends? You remind yourself that both of you know why you’re here—the key is making that connection in an authentic way.

Then comes the chemistry test. Will they get you? Will they see the vision? Will they find you compelling or tune out after five minutes? You need to strike the right balance—confident but not cocky, passionate but not overwhelming, engaging but not dominating the conversation. This isn’t about a one-sided pitch; it’s a two-way street. You’re evaluating them just as much as they are evaluating you. Would they be a good long-term partner? Do they align with your values? Can they help you fill gaps where you need support?

Now, the conversation. You sit across from them with so much to say. You focus on making your points clearly and succinctly, avoiding rambling. You make eye contact, sit up straight, and try not to fidget. You know this isn’t their first pitch meeting, and it’s not yours either, but they hold the power of whether there will be a second meeting. You want to leave them with just enough intrigue that they want to continue the conversation, but not so much that you overwhelm them with every single detail about your business.

Then, just like a date, the meeting comes to an end. Did you make a strong enough impression? How do you follow up without coming off as too eager? Is a thank-you email enough? Should you send over a thoughtful note summarizing the conversation? Should you play it cool and wait for them to reach out? You remind yourself that if this doesn’t go anywhere, there are plenty of other investors in the sea.

Every meeting is an opportunity to refine your approach. Just like dating, you learn from each experience, adjust your strategy, and improve over time.

The analogy may make you laugh, but it holds true. A first meeting with a VC is just like a first date. Treat it that way—from how you dress to how you communicate and listen. Don’t push for a close; that’s not how venture investing works. Just like in dating, both sides need time to get to know each other, understand if there’s a real fit, and determine if this is the beginning of a long-term relationship or just a one-and-done meeting.

Jeffrey Silverman

Early-Stage Investing and First-Time Founders: 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.

Jeffrey Silverman

Portfolio Spotlight: Brooklyn Health

Laconia recently invested in Brooklyn Health’s $6.5 million seed round, alongside HealthX, Metrodora Ventures, Story Ventures, and RiverPark Ventures.

Brooklyn Health is transforming neuroscience clinical trials through Willis, its electronic clinical outcome assessment (eCOA) platform. Traditional CNS trials rely on subjective clinical interviews to measure treatment efficacy—an approach prone to bias and variability. Willis replaces that with a scalable digital phenotyping solution that brings accuracy and standardization to behavioral measurement.

The Willis platform is composed of:

  • OpenWillis – a library of validated digital phenotyping methods

  • WillisPipeline – infrastructure for processing behavioral data

  • WillisAPI – tools for digital health platforms to adopt proven clinical measures

Brooklyn Health was founded by ‌Anzar Abbas, Founder and CEO. Anzar is a neuroscientist with a career in healthtech. Before starting Brooklyn Health, he served as Director of Digital Health at Cambridge Cognition and held multiple roles at AiCure, including Global Head of Digital Biomarkers and Director of Research and Development. Earlier in his career, Anzar worked as a science communicator for PBS and was an AAAS Mass Media Fellow at HHMI. He holds a PhD in Neuroscience from Emory University and studied History and Philosophy of Science at Michigan State University.

Laconia backs seed-stage B2B software companies bringing structure to complex workflows—and Brooklyn Health’s mission aligns perfectly with that thesis. We’re proud to support ‌Anzar Abbas and the team as they build the future of neuroscience research.

For more information on the investment, read here: https://www.mobihealthnews.com/news/brooklyn-health-scores-65m-improve-mental-health-assessment-clinical-trials

Portfolio Spotlight: SportsRecruits Acquisition By IMG Academy

Laconia is thrilled to announce the successful acquisition of our portfolio company, SportsRecruits, by IMG Academy.

By 2014, after four years of full-time angel investing together, Jeffrey and I (David) had refined an investment thesis around B2B seed-stage workflow automation that remains central to Laconia today. When launching Laconia, we wanted to provide our prospective LPs with a tangible, thesis-driven portfolio company they could be owners of from day one. That company was SportsRecruits.

We were introduced to SportsRecruits founders Chris Meade and Matt Wheeler through one of our pre-Laconia portfolio companies. Chris and Matt were solving a highly manual workflow problem—helping high school student-athletes create visibility into their club sports success for college programs, and vice versa.

SportsRecruits was a company we never lost sleep over. It was a capital-efficient platform that quickly generated cash flow while sustaining strong year-over-year revenue growth. Chris and Matt understood their customers’ needs and built a sales and marketing engine that continued to execute—even through the challenges of the youth sports market during the pandemic.

This moment is bittersweet—it marks a successful exit, but also brings a wave of nostalgia. It made us take a walk down memory lane. When we first backed Matt and Chris, they were recent Wesleyan grads—hungry, single, and ready to build. We, on the other hand, were proudly sporting full heads of dark hair. Today, as they exit the company they built from the ground up, they’re both married with families. And we… well, we have a little less hair, and what remains has gone gray.

Being Laconia’s first investment that showcased our thesis to our founding LPs gives this exit special meaning. A big congratulations to Chris and Matt—and a heartfelt thank you to our Fund I LPs for believing in Laconia from the very beginning.

When we invest, we strive for two outcomes: great returns and lifelong relationships. In this case, we’re proud to say—mission accomplished.

You can read more about the announcement here.

The Next 10 Years

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

As we look back on our first decade at Laconia, we find ourselves reflecting not just on where we've been, but where we're headed. The venture capital landscape has evolved dramatically since that first conversation over drinks, and the pace of change shows no signs of slowing. So what does the future hold for Laconia and for others in the ecosystem?

Embracing Our Core Identity

If there's one thing our journey has taught us, it's the importance of staying true to who you are. When we started Laconia, we didn't try to replicate other venture firms—we built something that reflected our own experiences as operators and our values as people. As we look to the next decade, we're doubling down on what makes us unique.

Our focus will remain on seed-stage B2B software companies bringing systematic order to traditional industries. This approach has led to successes like TripleLift, AutoFi, and Ocrolus, and we’re excited to back the next wave of innovative companies. By maintaining clarity in our investment thesis while remaining open to opportunities across sectors—from healthcare with Yuvo Health to LLM marketing optimization like Bluefish AI, we've built a portfolio that reflects both conviction and adaptability.

The venture industry has seen growing concentration of capital, with dollars flowing to fewer decision-makers and deals. This consolidation creates both challenges and opportunities. For founders with the right connections or working on trendy problems, capital is more abundant than ever. But for those building in overlooked areas or without established networks, the funding gap has widened.

This is where our independence becomes a strategic advantage. We're not beholden to larger funds or a small group of institutional LPs with rigid mandates. We're free to back founders we genuinely believe in, regardless of whether they fit a typical pattern. Building a sustainable capital base takes grit and determination, but it creates the freedom to make decisions based on conviction rather than conformity.

Systematic Order + Human Partnership

Our anti-chaos framework will continue to guide us in the next decade. Bringing systematic order to the inherently chaotic process of early-stage investing creates a powerful advantage. We'll continue to:

  1. Identify Underrated Opportunities: Target industries where lack of systematic processes creates inefficiency

  2. Apply Consistent Evaluation: Utilize structured assessment frameworks and data-driven decision-making

  3. Drive Exceptional Execution: Implement structured operational support and measure specific value-creation metrics

But what makes Laconia special isn't just our systematic approach—it's how we balance this with genuine human partnership. As we've grown, we've never lost sight of the fact that venture capital is fundamentally about people. The serendipitous meetings that brought our team together remind us that human connection remains at the heart of what we do.

This balance of systematic process and human connection will become even more important in the coming decade. As AI and other technologies transform how we work, the firms that can harness the efficiency of systematic processes while preserving the irreplaceable value of human judgment and relationship will have a distinct advantage.

Building an Ecosystem, Not Just a Portfolio

Perhaps our proudest achievement has been building something bigger than just a portfolio of companies. Through our engaged LP network and initiatives like the Venture Cooperative, we've created an ecosystem that extends our impact far beyond our direct investments. This approach creates multiple advantages:

  • It expands our market footprint and deal flow

  • It builds a pipeline of potential investors who deeply understand our approach

  • It strengthens our network and brings diverse perspectives to our work

  • Most importantly, it extends access to venture capital education and opportunity

In the next decade, we'll continue to scale this ecosystem-first approach. We believe that by opening doors for others, we don't diminish our own opportunities—we multiply them. The 1,300+ fellows in our cooperative have identified hundreds of startups, many of which have entered our diligence pipeline and portfolio. Without the constraint of prohibitive minimums, Venture Cooperative participants have made their first LP investments in our funds. They've connected us with talented team members who now strengthen our firm.

This approach stands in contrast to the increasingly closed networks that characterize much of venture capital today. While we recognize the efficiency of relying on trusted connections, we've seen firsthand how expanding beyond the usual suspects can uncover extraordinary opportunities that others miss.

Lessons for the Path Ahead

As we look to the future, we carry forward key lessons from our first decade that will serve us—and perhaps others in the ecosystem—well in the years ahead:

1. Focused Flexibility: A clear investment thesis doesn't mean rigid constraints. By focusing on B2B software companies solving critical operational challenges while remaining open to diverse sectors—from finance to healthcare to climate tech—we maintain both expertise and optionality.

2. Value Independence: Building a sustainable capital base from diverse sources preserves decision-making freedom. Our LP base allows us to make investment decisions driven by conviction rather than external pressure.

3. Balance Rigor with Empathy: Systematic processes create competitive advantages, but only when balanced with genuine human connection. Our due diligence process combines rigorous analysis with relationship-building, turning what is typically transactional into an opportunity for partnership.

4. Create Virtuous Cycles: The Venture Cooperative demonstrates how giving back creates powerful flywheels that expand impact while strengthening core business. By training over 1,300 fellows (80% from underrepresented backgrounds), we've created a community that enhances our sourcing, diligence, and portfolio support.

5. Stay Curious: Our serendipitous beginnings and team formations highlight the importance of maintaining curiosity and openness to unexpected opportunities. This curiosity has led us to back diverse founding teams—not because of quotas, but because our networks and perspectives are broader.

The venture landscape will undoubtedly continue to evolve. Market cycles will turn, technologies will transform industries, and new models of funding innovation will emerge. But these fundamental principles—focused flexibility, independence, balanced rigor with empathy, virtuous cycles, and curiosity—will remain relevant regardless of how the external environment changes.

Our Commitment

As we look toward the next ten years, we're committed to building on these foundations. We'll continue to lead seed rounds in B2B software companies bringing systematic order to traditional industries. We'll maintain our high-conviction strategy while expanding our geographic reach. We'll deepen our repeatable investment processes while strengthening our human partnerships with founders.

Most importantly, we'll stay true to our values of transparency, collaboration, and community. We'll continue opening doors for founders and investors, demystifying venture capital through education and accessibility, and building a firm that creates value for all stakeholders.

Ten years from now, we hope to look back and see that we've built more than just a successful venture firm. We aspire to have contributed to a healthier, more diverse, and more innovative ecosystem—one that better serves founders, investors, and ultimately society as a whole.

Here's to the next decade of systematic order and human partnership.

Geri Kirilova