This page is mostly for people thinking of having me on as an investor for their company.
For whatever reason, I’ve been interested in investing since I was a kid, and it’s continued to ‘snowball’ ever since.
I invest across many different types of assets, am very comfortable being the first money into a new manager or operator, and simply look for interesting risk/reward tradeoffs that have a clearly definable reason for beating the mostly efficient markets that we live in.
Search funds
I interned at a search fund nearly two decades ago, and love that this niche scratches my entrepreneurial itch while also providing some interesting economic opportunities as an investor. Here are some investments I’ve made:
- B2B financial services marketplace
- Professional services in the government contracting space
- Telecom services business
- Landscaping roll up
- Roofing maintenance and repair
- Specialty manufacturing selling to government
- Cohort based traditional search incubator
- Traditional search focused fund focused on new MBA grads
- Traditional search permanent capital vehicle focused on mid career searchers
I continue to be very interested in investing in search funds, and generally participating in this part of the entrepreneurial ecosystem.
Technology Investing
I’m very passionate about how technology will continue to change the way we live and work. Please note, I very rarely will invest in companies with <$10 million ARR at this point, and almost none with <$1 million ARR. This is especially true given the market valuations for these types of companies, and the amount of time/money needed to build a diversified portfolio in this segment.
Here is some flavor for my tech investing:
- Secondaries in companies such as Snowflake, Toast, Better Mortgage, MalwareBytes, Hashi, and others
- Seed stage investments in direct to consumer and financial services
- Fund focused on marketplace businesses with profitable unit economics
- Structured credit into media assets with predictable recievables
- Once in a lifetime investments at the Series A/B stage in companies like PINS, TWLO, SHOP, WIX, FVRR via a very good company perk
- Fund that helps non-VC backable companies get to profitability
Real Estate
- My first ever “private” investment where a friend identified an opportunity to buy a minority stake in a NYC apartment building at a steep discount to market given the owner was under investigation by the IRS and needed liquidity fast.
- A first time manager dedicated to revitalizing a specific part of New Haven, CT
- Distressed hotels on the campus of a large university in the US (and in the wrestling heartland as some icing on the cake)
- Manager focused on buying under appreciated strip malls
- Working capital loans to developer
- Institutional scale opportunistic fund
Private Credit
- Litigation finance fund, in latin america
- Bridge loans for government backed borrowers
I’m always on the lookout for the chance to partner with managers who’ve found new/weird/niche/special opportunities. If there’s something I should look at, please shoot me a note!