My typical check size is $25k.
Thus far my best claim to investing fame is that I invested in NS8 in 2017 at $2.5m and $3.5m valuations; in February 2019 they raised $26m on a $100m note and in June 2020 they completed a $123m raise (I anticipate them hitting a $1b valuation in 2020). Thus far all of my angel and seed stage investments have raised subsequent rounds.
I am investing both as an individual and as an "Open Angel," a program created by Bloomberg Beta, the early-stage venture fund.
Bloomberg Beta created the Open Angels program to deepen relationships with a handful of angels they trust. They will back every deal I syndicate at a fixed ratio with my personal investment. (In my case, Bloomberg Beta invests $1 for every $1 from me.) While a portion of each allocation I bring will therefore be reserved for Bloomberg Beta, they do not intend to be direct investors in my portfolio companies and I will manage the syndicate's relationship with companies. Bloomberg Beta's intent is to support people they trust as investors, and extend their fund to support many more companies, not to create direct deal flow for them.
I will syndicate all deals through AngelList, so backers will have access to any deal I do. Allocations will vary, with preference given to pre-committed capital.
My normal check size is $20k to $25k and I typically make 1 to 4 investments per year. The syndicate will typically target making $100k+ investments.
I am a founder of and the CEO of Virgil Security. Virgil Security provides cryptographic building blocks for software developers so that they can quickly and easily add privacy and security to their products without having to become security experts themselves. Many of Virgil's customers are startups. I also mentor startups in the greater Washington DC area and, when time allows, in the Rice Business Plan Competition, Princeton Entrepreneurship Club's TigerLaunch, and NYU Stern's Entrepreneurs Challenge. In these roles, I meet scores to hundreds of exciting new companies every year; however, I only invest in a very small number of those companies.
Some of my more recent angel / seed investments include CyberAcademy (now HyperQube), NS8, RunSafe Security, Shevirah, Syncurity (exited to Swimlane in April 2020), ThreatSwitch, and vThreat (now ThreatCare, exited to ReliaQuest in October 2019).
I participated in NS8's $2m and $3.5m convertible rounds and facilitated both their late 2017 $7.5m raise ($25.5m post) as well as their March 2019 $26m raise ($100m convertible cap). I introduced them to 3 of the 4 institutional investors in their 2017 round as well as most of the investors in their March 2019 round.
I invested in RunSafe Security prior to their 2017 participation in the Mach37 cybersecurity accelerator, facilitated CIT GAP fund's subsequent investment, and introduced RunSafe to Alsop-Louie who led their 2018 and 2019 priced rounds.
I was ThreatCare's first angel investor in 2014 and spearheaded their $600k angel raise in 2015 -- before their 2017 acceptance into TechStars Austin. ThreatCare raised at least two subsequent rounds after my investment before exiting to ReliaQuest in October 2019.
Syncurity (2015 investment), Shevirah (2017 investment), and HyperQube (2018 investment) have also all raised additional funds since my initial investments.