Hundreds of cold emails to firms led to a few opportunities to work for free (or very little money). I then scrapped together sufficient experience through my part-time venture roles and various operating roles to sufficiently excite a major fund (Bessemer), which ultimately hired me. Now that I've left Bessemer, I'm wearing the operating hat again as a Chief of Staff at a Series B company, but I also deploy a micro fund + support entrepreneurs with every spare minute I have.
Founder-market fit, complementary skill sets + perspectives, a demonstrated track record of persistence through adversity, and an unrelenting belief that their product/service needs to exist.
I like to roll up my sleeves and get my hands dirty. I'm happy to stay out of their way if that's what the founder wants, but I enjoy being the strategic advisor that they call with their most pressing questions. I am happy to be a sounding board, a trusted confidant, and an intellectually honest resource. I work well with founders that seek out truth about their customer and market, consistently asking "why" and inspiring those around them to work hard through action. These CEOs are generally strongly opinionated but open to data-driven debate, and they accept feedback but have a clear vision for where the company will succeed and how they will get there
Be honest. I don't like when entrepreneurs overstate traction or projections -- it causes them to lose credibility in my eyes. Also, come prepared to defend your claims. There is nothing worse than hyperboles or theses that are unsupported by real data and fall down with any degree of prodding.
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I want to invest in entrepreneurs that are building businesses because they truly believe that their product will bring good to the world. My personal mission is to invest in and empower entrepreneurs that have the will power to bring their product to life, and the resilience that can only come from true mission-driven building. I also often invest in categories and people that can drive meaningful socioeconomic change. I like working with people that are equally inspired to change education, healthcare, financial services, food waste, etc. -- not only because these are meaningful and large markets, but also because driving change in these categories will enhance the way that people work, live, and grow.
I love investing in NYC entrepreneurs because I find them less hand-wavey than entrepreneurs from other geographies (not always the case, but sometimes). I think that the future of NYC tech is bright -- brimming with talent that is slowly starting to leak out of bigger NYC based "startups" that have gotten to scale / exited.