VC Spotlight: Oliver Libby, Cofounding Managing Partner, H/L Ventures
Oliver Libby, Cofounding Managing Partner at H/L Ventures, didn’t start with a traditional VC background. As you’ll read in our interview below, he grew up surrounded by family members who were physicians, Nobel Prize-winning scientists, and military veterans. Oliver, himself, was drawn to military history and national security in college, and was even selected to join a CIA program while in school.
So how did he ultimately find himself in the venture capital industry? Call it a combination of working with startups (originally as a consultant) with a passion for helping people grow companies that protect or promote people or the planet — the four Ps, as he calls it.
Oliver’s upcoming book, Strong Floor, No Ceiling (out this November 11), lays out a vision for the United States, and the tech sector is deeply intertwined in that vision: “Our tech sector has a huge role to play in creating a positive, inspiring vision for our country,” he says.
We caught up with Oliver to discuss his career, who he hopes picks up his book, the most common mistake he sees from founders when pitching to investors, and much more.
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Where did your career start?
Oliver: I have enjoyed a very non-traditional pathway into venture capital. I grew up surrounded by scientists, with my great-great uncle (Jacques Monod) and grandfather (Baruj Benacerraf) winning Nobel Prizes in medicine respectively, and a mom and dad (Beryl Benacerraf and Peter Libby) who are renowned physician scientists in their own right.
However, there was always a deep fascination with history in the family and a strong streak of military service, from my great-grandfather in the French military through both World Wars, to Jacques’ renowned heroism in the French resistance, to both of my grandfathers serving America in World War II. I was deeply drawn to military history and national security, studied that in college, and was selected to join a program at the U.S. Central Intelligence Agency while still in school that brought young analysts into the agency with full clearances.
From there, I went to join a consulting firm to learn more about the private sector and America’s economic engine, and it was there that I first started working with startups in which we took some equity since they couldn’t afford our standard fees. During the 2008 Global Financial Crisis, I took the opportunity to cofound two organizations. First was a nonprofit called The Resolution Project, which I started with some of my best friends from college, and which is now the world’s premier college youth social enterprise organization. Resolution and our newly merged partners at Enactus have launched nearly 1,000 young entrepreneurs across close to 100 countries and the United States into socially-responsible innovation, creating over $6 billion worth of social start-ups and now also training about 50,000 young people each year globally.
Second, I cofounded H/L Ventures (which includes H/L Studio and CityRock Venture Partners) with my great mentor and dear friend Eric Hatzimemos. We have grown H/L Ventures into a company-building platform over the past nearly two decades, and I am incredibly proud of our work and our team.
You cofounded H/L Ventures in 2009 — what was the catalyst?
Truthfully, Eric and I set out to do something we enjoyed, which is to work hand in hand with people to help grow companies. The investing work is a part of that — almost a result of the opportunity that comes from partnering. Much of what we believe is rooted in the realization that venture capital often has a difficult relationship with founders and is more focused on investing than building. So perhaps, we thought, taking an active engagement approach — leveraging our knowledge, experience, networks, and capabilities for a focused set of companies every day — could yield compelling investment performance and also be rewarding.
We from the outset wanted to build companies doing worthy work, but that could also generate market returns for investors, so we invest in companies that help protect or promote people or the planet. We also believe a diverse founder community — diverse in race and gender, but also in life experiences like military and government service, geographic and socio-economic variation, and even age — should be more resilient, diversified, and also rewarding to work with. Those were the insights and mission from the beginning.
What stage do you invest at and what’s your average check size?
We have two primary entry points at our firm. First, our venture studio, H/L Studio, works with companies ranging from cofounding all the way to after Seed rounds. In exchange for open-ended active support for the company from inception to exit, the Studio takes a bespoke common stock option averaging about 8% of the company (commensurate with some accelerators, inexpensive for a venture studio) and commits $100,000 to market seed rounds as part of the process.
Our CityRock Venture Partners fund enters normally in Series A or smaller Series B financings and invests $500,000-$1 million, with a smaller common stock option for our unusually active support.
How does H/L Ventures’ Daily Active Engagement model differ in practice from traditional venture capital approaches, and what impact have you seen it have on portfolio company outcomes?
Active engagement is why we started the H/L family of companies, and it is the beating heart of our business. I want to emphasize that most VCs I know do try to help with varying degrees of success, but we are purpose-built for a different level of engagement. Founders need a place to turn when real work shows up between board meetings — things like hiring, pricing, customer pilots, fundraising mechanics, brand strategy, board strategy, comms, fundraising, talent, and the inevitable crises and disappointments too.
Our platform team, which has been a priority from the earliest days, now counts around 80 people (full and part time), and our culture is built around the active support of our companies. We have spent a decade and a half building out all sorts of toolkits, teams, approaches, and partnerships to support our ongoing work with start-ups, stay connected constantly, and be of service whenever and however possible. We have an overall weekly operating rhythm, centered around a fixed call with every active portfolio company, but generating all sorts of other activities from emails and calls, to research and projects, to networking and outreach. We’ve helped our teams with everything from executive talent placement and introductions to partners and co-investors, to pricing strategy insights and competitive analyses, deep discounts and access to critical start-up tools, and so much more.
We also involve our platform in the earliest stages of due diligence, including by hosting a wishlist call with every company to see what they feel their needs are, and by ensuring that our platform leader is a full General Partner at the firm and has an investment committee seat.
The impact is, we believe, fewer avoidable challenges, better use of founder energy, and crafting a trusting relationship we carry through many years with each founding team. In essence, it means we try to have agency in the outcome, alongside the amazing founders we back, and I wouldn’t have it any other way.
Social impact is a big part of H/L Ventures’ investment thesis. How do you measure social impact alongside financial returns when evaluating companies at H/L Ventures?
As part of our traditional underwriting process, we also evaluate companies through our 4P lens — protecting or promoting people or the planet. We have never tried to label that style of investing, but we simply believe that we can have non-concessionary market returns and also invest in companies that are aligning good values and strong integrity with generating economic value. Throughout our years working closely with each company we try to help founders and their teams stay true to their intentions and values as they grow.
Your upcoming book, Strong Floor, No Ceiling, comes out in November. How do you hope the book will reshape the conversation among entrepreneurs, investors, and social impact leaders around their role in civic and policy engagement?
Thanks for asking! I’ve always believed that the tech and startup world is perhaps one of the most intertwined in government, policy, opportunity for our people, and making the engine that is America work. Innovation and entrepreneurship are so intimately tied to the idea of the American Dream. Our successive generations of technology leadership, visionary company building, and the powerful public-private partnerships that have supercharged those things here in America are vital.
As a VC who has served in government (and many of our team have incredible public service records), who has built a nonprofit, and who invests in the private sector, I feel the relationship and dependence between the sectors keenly. I have always stayed close to the world of politics and policy, and I started writing Strong Floor, No Ceiling in 2018. It is a practical vision for a plan for our country that comes from what I call the “radical moderates” — the center that so many of us inhabit, but that can actually be an inspiring, powerful source of policy. We need to reignite the American Dream, and recognize that this is most possible when we have a Strong Floor below which our fellow Americans don’t fall — planks like healthcare, education, jobs, homes, and opportunity that they can stand on to reach for success — but that those very aspirations should have No Ceiling, and that a society like the one I envision needs a vibrant economy, capitalism, wealth creation, and innovation to work.
Our tech sector has long been — or felt — distant from policy, with notable exceptions, but I think if contributing the Strong Floor, No Ceiling vision to our fraught political discourse can help, that’s great. There are also in the book very specific clarion calls for innovation in key sectors, huge investments in entrepreneurship, support for key jobs of national priority, incentives to invest in these things, and also hard truths about the impact of technologies like social media and AI on a democratic nation if there are not sensible guardrails. Our tech sector has a huge role to play in creating a positive, inspiring vision for our country.
Who do you most hope will pick up this book — policymakers, entrepreneurs, or everyday citizens? And how do you want each group to act differently after reading it?
This is written for everyday Americans. Sure, policymakers, captains of industry, academics, and others should find it useful — and I hope it can power messaging and action for our political leaders across the spectrum — but this book is written for the huge numbers of Americans who feel politically adrift, betrayed in many ways by our institutions and leaders, and losing faith in that central idea of our nation — the American Dream.
I want people to believe that this can all work again, and I think that this is the plan to make that happen. I also don’t think everyone will agree with everything in the book; it’s not designed for that. But it is a framework for looking at our country in a way we can all get behind.
People ask me if this means I’m running for office, and I’ve always said I’d love to do that eventually, but I’m focused on the firm and our investors and founders. Anyhow, one shouldn’t have to be running for office to contribute something meaningful to our political discourse. As I like to say, you can choose to ignore politics, but politics never ignores you…!
What’s the most common mistake you see founders make when pitching to investors?
I would share a few things below, although goodness knows we’ve seen a lot.
First, at least for us, the fake FOMO “I’m talking to a lot of investors, the round is moving fast, you have until Friday” approach doesn’t work. We see about 2,000-3,000 decks a year and invest across our whole platform in about 5-8 new companies, so we’ll pass on being rushed. We take the time to underwrite and establish trust and a fit — even then, this is a hard challenge — but FOMO is a bad strategy today.
Second, founders often spend WAY too long on establishing the problem, and not enough time on the solution, its unit economics, and why it works as a business. Usually, we either agree something is a valuable problem or not within five minutes; we want to know what you’re doing about it, where you are in that process, and how it’s working economically — that should be 90% of a pitch.
Third, we see founders brush off differentiation and not know their own competitive landscape. Either you know about your competitors and you won’t tell us, which is a mistake, or you don’t know about them at all, which is also a mistake. Most startups have competition — tell us all about them in detail and why you are still better.
Last thing I’ll note is that we’ve seen a troubling rise during these more difficult times in some founders not telling the truth during underwriting. Every VC knows about reality distortion fields and how founders have to live in a hopeful place, but there’s a big difference between that and hiding things, not telling the truth, or misleading investors. That never ends well.
What’s an investment from the last 12 months you’re especially excited about?
We really try not to answer this question, as we are excited about all our investments (when you’re down-selecting from thousands of decks to a handful of deals, you’d better be!).
Perhaps one of our prouder achievements of the year is that no fewer than three of our portfolio companies in which we led the prior round have had up-rounds in the past quarter. Since mid-2022, it’s been a challenging time for venture-backed startups and the funds that invest in them, so we are very excited about these new rounds.
What are some of the top resources you recommend for founders starting out?
That’s a trick question for us, because our whole business is premised on a vast array of curated resources that we have for our companies. So I have to say the H/L Studio, our platform team, our Trusted Partner Network, and our incredible store of expertise would be the top resource for founders that I can think of — we built it painstakingly over the years to be just that.
A huge nod to my partner Galina Ozgur, who has taken that organization to unimagined heights, as one of the most accomplished professionals in the venture space.
You have a founder or LP in from out of town… where are you taking them?
The Rainbow Room above our beloved Rockefeller Center has become an unofficial HQ for our team. We have in many ways built our business up there, surrounded by a panoramic NYC view that honestly never gets old. Somehow, from the newest young founder to the most jaded family office, everyone seems to agree that it’s an amazing, iconic place.
Choose one: power breakfast, power lunch, or work dinner. Where?
Well, context is everything, so let me give you one of each from each sector of my life. I love a power breakfast at the Regency when doing anything in the public service realm — it’s the venerable capital of politics in New York City. I love lunch at the Rainbow Room (already explained why). And I cannot tell you the number of late night dinners I’ve had with our non-profit team at various dinners across New York, notably the Red Flame on 44th and Madison Restaurant on 53rd.
And finally… what’s the best slice of pizza in NYC?
At what hour of the night? Ok, just kidding — I mean, Joe’s is a huge favorite at home (my son loves the little pepperoni), but there’s also a slice shop down the block from our house that does the trick for me.
