Syndicate Lead Profile #1: Ashley Flucas

Giri Cherukuri
The Syndicate Investor
5 min readSep 13, 2020

The following is the first in a series of profiles of venture capital syndicate leads. Hopefully this helps you become a better investor and discover syndicate leads that you may want to back.

Please contact me if there is a particular syndicate lead that you would like profiled.

Ashley Flucas
Ashley Flucas — Flucas Ventures

AngelList Syndicate:

Please briefly give us your background and how you got into the venture world?

I started my career as a capital markets lawyer, and I practiced in London to get exposure to cross-border work (and because I was still figuring out what I wanted to do in the investment world and thought working on these types of deals was a good start). I am now the General Counsel and a Partner at real estate finance fund with ~$3B AUM. A couple of years ago, I decided I wanted to explore venture, but was unsure how to start being located in south Florida, which does not have a robust VC ecosystem. I did my homework and found platforms like AngelList and just dove right in. I then joined various angel groups, started to network and look for deals directly and eventually felt I had enough of a handle on things to start a syndicate.

How did you decide to become a syndicate lead? How does being a syndicate lead fit into your “day” job?

It was in the back of my mind for a long time, but I knew I needed to figure out both dealflow and building a network. It all came together in 2020. When the world went virtual in March, I had my “aha moment” realizing I could cover a lot of ground quickly and was now on an even playing field because all business would have to be conducted virtually and I just had more bandwidth as a result of staying home more. I decided to form my syndicate and start building it out before I had my first deal and decided I would launch once I had a really good one — my mantra is always if you stay ready, you don’t have to get ready. And once the right deal came along, I successfully launched and the networking done over the past few years really paid off as I received some great mentorship along the way (and now try to pay that forward).

I think I bring some of those same skills in leading a syndicate — as a lawyer, I am used to due diligence, writing and understanding, interpreting and communicating complexities into plain English. I wake up earlier these days to do VC tasks before my workday starts and then work on weekends as needed. But I’m finding the more I do it, the more efficient I am becoming. Now that some of the heavy lifting has been done (building out LP base, etc), it’s possible to balance both without sacrifice to the other.

Please describe the types of deals that you syndicate? (sector, stage, etc.)

I am sector, stage and geography agnostic (though I’ve never done a blockchain or crypto deal). I am not a technologist by background and I think this makes me highly curious and gives me an open mind to explore a lot of companies. My portfolio spans the gamut, but in reality the companies tend to share a lot of things in common that I look for (despite the product or service variance). Of course, I am really interested in companies that address our new reality (and was lucky to bet on some that have now really taken off ahead of schedule).

What was the first deal that you syndicated? How did you source that deal? How has the investment turned out?

Foodology (LATAM Cloud Kitchens). This was a time it was better to be lucky than good. It was sent to me by a contact who’s well connected within LATAM. It went better than I could’ve hoped for. I co-syndicated it with a great lead (Peter Livingston of Unpopular Ventures) and we raised enough to be considered a major investor.

What is the approximate frequency of syndicated deals that you do?

I expect there will be ebbs and flows, but based on the current pace (between deals I lead and co-lead), it looks like I’ll do 3–5 per month.

How important is getting information rights and pro rata rights in the deals you syndicate? Do your portfolio companies share regular updates with syndicate members?

It would obviously be great, but you really have to punch above your weight class sometimes to do it because most of the time your allocation is not going to be enough to be considered a major investor. However, my other mantra is “a closed mouth does not get fed”, so I always ask and am usually able to secure pro rata rights; information rights are harder but so far I’m finding most companies have good sharing practices anyway. I just launched the syndicate in June, so it’s a bit early to forecast re: updates. I think my practice will be to share news that is material, but I don’t want to flood everyone’s inbox either.

What do you look for in syndicate members?

My favorite thing about the syndicate is how helpful the backers are. In fact, it’s one of my main selling points to founders. They have been willing to help with diligence, hires and even connecting potential customers and channel partners. One of my missions is to democratize access to great deals which is why my investment minimum is low and I am open to all different types of backers. And I want my backers to be as diverse of a group as possible — with respect to geography, race, gender, sexuality, education, profession, etc. In my view, that separates us and leads to some really interesting viewpoints and capabilities.

What websites, podcasts, blogs, etc. do you follow to keep current on the angel/venture capital world?

I try to not to have an information overload, but I do like newsletters: Fortune’s Term Sheet, Morning Brew, Strictly VC, the Synthesis, Box of Amazing and Not Boring are the ones I read.

What books would you recommend to someone interested in the angel/venture capital world?

The Monk and the Riddle (my favorite book of all time and what inspired me to try VC)

Play Bigger (really helped me frame my thesis and evaluate deals)

What’s your favorite book of any kind (fiction or nonfiction)?

See above. But also, I love the Kingkiller Chronicle by Patrick Rothfuss (I’m a bit of a fantasy genre nerd).

How can people reach you?



Giri Cherukuri
The Syndicate Investor

Individual Investor and Baseball Card Collector — Follow me here: