Ashley Flucas has invested in 250+ startups. As the head of Flucas Ventures, a syndicate of about 4,000 venture capital investors (and growing), she serves as a partner at a South Florida-based real estate finance fund. She is also in the ownership group of the Nassau Coliseum sports and entertainment venue in New York. She started her career as an attorney in Davis Polk & Wardwell's London office, focusing on capital markets. Her experience spans real estate, venture capital and the gamut of capital markets - debt and equity, IPOs, SPACS, bond offerings, right offerings and public company reporting."The biggest challenge was deciding to want to be a VC investor and navigating that as a total outsider – no direct investing experience and not running in the circles of an access-driven asset class. So I had to overcome the “zero-to-one” problem and be completely self-taught re: investing and network", she says.
Now Ashely straddles two worlds between real estate and VC. On the real estate side, she joined her company in 2014 and was promoted to partner in 2017 – "the move was driven by my desire to learn more about investment and finance (in this case real estate finance)." On the VC side, she started investing in 2018 (personal capital) and then formed the syndicate in Q3 2020 which has since deployed ~$85M into startups (all stages, sectors and geographies), with fintech as the largest (though not exclusive) category. "On the VC side, it’s just me, but I collaborate with tons of great people across the venture landscape – from other angels and syndicate leads to funds. On the RE side, I’d say it’s entrepreneurial and flexible which is great considering I straddle two worlds."
Ashely is proud to impact FinTech by deploying capital into a significant number of fintechs globally and via her advisory work at Fin Capital.
What's the best job decision you ever made? What's the worst job decision you ever made? Best = being decisive early (I was less than 3 years into my career) and betting on myself that I could exit the law firm environment ahead of the typical timeframe, so I could move closer to what I always wanted to do – investment and being close to day-to-day business operations.
As to the worst, I like to think I haven’t made it. I am not someone who really has regrets. I think everything is a learning experience and I wouldn’t be where I am today but for every past decision and I’m good with that.
Can you tell us about a time someone encouraged you to try a task or take on a project you didn’t think that you would know how to do/or be good at?
One thing I don’t lack is confidence (at times, maybe I’m overconfident) but I always feel (even if others don’t) that I belong and given the opportunity, I can figure it out. As they say, there’s only one way to eat an elephant – one bite at a time. And I believe that if I take that approach, I can master most new tasks even if outside of my expertise.
What is the most important lesson you have learned from a mistake you’ve made in the past?
I think the #1 thing (which is also the usual parting advice I leave with folks) is analysis paralysis. I honestly wish I’d tried to get active in VC years before I did. I first had the inclination a decade ago and it took me 6 years to start.
More on Ashley
Where you currently live: Palm Beach, FL
Living arrangement: With my partner
Family at home: no kids
Hometown: Ocala, FL
Favorite hobby: watching basketball (Go, Duke!)
Favorite part of your day: mornings on the way into the office – on the 45 min or so commute I always talk to family – my mom, brother, aunt etc.
Favorite show to binge: A tie between House of the Dragon and Rick and Morty.
Daily Diary
Monday
7:00 am: Wake up! Clear any emails from overnight (I am an inbox zero diehard) and then catch up on news online (newsletters like WSJ 10 of the day, Term Sheet, etc) for ~ 1 hour.
8:00 am: Quickly get ready and commute to my office (45 mins away).
9:00 am: Organize. I am worthless if I don’t feel like I am organized. So I go over goals for the week, larger projects and then create a must-get-it-done task list for the day.
9:30 am: It varies. A mix of calls and assorted tasks – could be assisting with investor relations, reviewing transaction documents, sketching out strategy for a new project, reviewing deals, etc.
1:00 pm: Business update meeting – meeting with other partners + department heads to talk through objectives and get updates on key projects
2:00 – 4:00 pm: VC founder calls and deal review.
4:00 pm: Head home to beat the traffic
5:00 pm: Pick back up on any remaining tasks.
7:00 pm: Dinner
8:00 – 9:00 pm: Read. Could be a book or just articles, but I like to feel like I learned something each day.
9:00 pm: Turn my brain off. Watch a game, Netflix etc.
11:00 pm: Bedtime!
Friday
7:00 am: Wake up! Clear any emails from overnight (I am an inbox zero diehard) and then catch up on news online (newsletters like WSJ 10 of the day, Term Sheet, etc) for ~ 1 hour.
8:00 am: Typically no commute today. Reflect on the week and see how effective I was on the “must-get-it-done tasks” and how I can be more efficient the next week.
9:30 am - 3:00 pm: It varies. A mix of calls and assorted tasks – could be assisting with investor relations, reviewing transaction documents, sketching out strategy for a new project, reviewing deals, etc.
3:00 pm: Organize/plan for the upcoming week and set priorities as to not feel any guilt about any weekend hiatus on any matters if I have plans.
4:00 pm: I’m either headed home or headed to the airport. I am a travel addict (80+ countries visited; though a less compelling state count of 32) – if there’s somewhere I can squeeze in a weekend trip, I’m outta here.
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