Great Oaks

Henry McNamara


Henry is a General Partner at Great Oaks, and was previously a Principal at Great Oaks. Henry holds a Bachelor of Arts from Bowdoin College, with a double major in Economics & Environmental Science and a minor in Government & Legal Studies.

Want to view this full profile? Sign up!

Notable Investments

Acorns, Allbirds, Atom Finance, Away, Sundays, Oula Health, Maven Clinic, Moov

Questions & Answers

Origin Story: In a couple sentences, how would you describe your path to becoming an investor?

I was fortunate to intern at Great Oaks while an undergraduate in 2011/2012 and ended up getting offered a full-time analyst position right out of school. Venture wasn't as sexy then as it is today and I don't think I'd get the same job if I was graduating a few years later, but like many things in life and business the timing was right and I rode with some wind at my back for a few years as I learned how the landscape worked and where I could find my niche. As with most things, it involved a lot of luck and timing beyond my control but also seizing the opportunity

Investment Approach: What are the key factors you consider when evaluating a founding team?

As cliche as it sounds, the founders. Getting a feel for the people we are investing in is the most important criteria. Companies pivot, change, iterate. At pre-seed/seed, what we know is who we are investing in. We will be more interested if a company has a compelling service, solution or product but it all comes down to people who have a unique insight, skillset and determination. This is what we look for above all else

What's your style and approach when it comes to working with founders post-investment? What are the characteristics of founders you've worked well with?

We see our goal as getting founders and their companies to product/market/fit and their Series A. Series A is often the first real "marriage" founders will have with investors owning 20% of their company, having board seats, etc... We see our job as making sure they find the right partner and helping them scale up their team in order to accomplish that. I personally have felt most useful and helpful to technical founders who need help with soft-skills, network and recruiting talent. Because I am more of a soft skills people person, I've found that my abilities are most valued by founders who are not as comfortable building those parts of their company in the early days and where I can demonstrate meaningful help to founders.

If I'm coming to pitch to you or your firm, what's the one piece of advice you'd give me?

Don't think that prestigious schools or employers early in your career are worth harping on. While its great to see people achieve early on and go to great schools and prestigious firms, if you rest your hat on those accolades early on in your career I think it gives us pause rather than demonstrating the way you think and how you solve problems

How would you describe your own personal mission and values, and how do they impact the way you invest?

One of my favorite Latin phrases is Ad Meliora, meaning "towards better." There is so much in the world that is frustrating, unjust, hurtful and sad. The world is far from perfect and always has been, I love investing in businesses that are moving the world in a better direction, in big and small ways. Progress is sometimes slow, but seeing some of the meaningful impact our portfolio companies have had on industries over the past 7 years makes me believe in a better future. That is what makes my job fulfilling

What do you like best about investing in NYC, and what’s your outlook on the future of NYC tech?

I love the diversity of everything in NYC. While some other cities are siloed into one industry where seemingly everyone is working in the same sandbox the diversity of people, backgrounds, thought, industry and interests makes NYC and NYC founders compelling. As one of the fashion, media, finance, etc.. capitals of the world, there is so much of a global mindset and fascinating backgrounds vs. a singular identity.