Tips To Getting It Right Before Embarking On A Fundraiser For Your Startup

W2: What was your path to becoming an investor and what inspired you to get involved with Red Bear Angels?

When I graduated from Cornell in 2008, I dove right into technology as a part of Skype’s public relations team. Bringing this Jetsons-like technology into the mainstream was a fascinating experience, but it wasn’t until working on the PR for Foursquare – in the beginning days of the Bloomberg-driven NYC startup boom – that I became completely enamored with early-stage venture.


So much so that I joined a then even earlier stage company StyleCaster to help build the company’s marketing team. Through several inflection points many media startups faced during that time, our investors always approached conversations with that keen eye, pattern recognition, and unique perspective one could only obtain from investing as a profession.


So once StyleCaster got to a point that it was ripe for acquisition, I decided to transition over to the investing side. While working as a NY-based representative for a large fund out west, I received word that a few Cornell alums were starting an angel group dedicated to harnessing the entrepreneurship of Cornell’s network. I knew I had to jump on the train. With investing and entrepreneurial day jobs of their own, they brought me on as the firm’s manager to kick Red Bear Angels into full gear.


Fast forward 18 months, and thanks to the RBA Advisory Board – Deb Kemper, Sam Sezak, Thatcher Bell, Gus Warren, John Alexander, Harvey Kinzelberg, Drew Bagin, & Eric Young – we have invested $5.1M across a wide variety of 20 early-stage ventures founded or led by Cornelians with a group of 500+ members to support this growing network!

W2: How do you find the best startup deals?

It’s too early to determine which of our investments will be the best, as we’ve only been investing for sub-2 years, but our investment activity shows that it is much more common for Red Bear members to take to a company if it came recommended by other founders in our portfolio, our more active investors with deep ties to the Cornell entrepreneurship network, or investors with whom I have worked closely in the past.

W2: What are you looking for in a startup?

Proof of product market fit. There are plenty of great companies built on spec, but I prefer to work with the founders who have deep domain know-how and as a result understand the nuances of the fields they plan to shake up.

W2: What tips do you have for women who are looking to get more involved in the angel or venture investing space?

Build a diligence network and leverage it wisely. There is no better way to analyze a company than by listening to close contacts with relevant domain expertise reveal their candid thoughts, and then synthesize those thoughts into an investment thesis. For instance, any time I look at an investment opportunity in healthcare IT and infrastructure, I discuss it with my friends who are doctors to determine whether it’s a needed problem-solver, a nice to have, or a logistical nightmare to onboard and implement.

And any time I’m looking at a new AdTech play, I’ll loop in publishers and Ad Ops specialists to determine how much they would realistically spend on a feature like this. Collecting these data points is key, but the practice of synthesizing these points in an actionable way is what will make you a great investor. I would give the same tip to both female or male investors.

For female investors, in particular, I would simply forget any gender difference, sit in the same posture as other men in the room, speak in the same pitch, and straight up do your job. You too can wear AllBirds and jeans to meetings. Act as if, and the playing field will level itself out. Pick a female mentee while you’re at it, as that’s how we can make sure we’re not evening the ratio purely for the sake of numbers!


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