Ashley Flucas of Flucas Ventures // turning 100 angel investments into an AngelList syndicate [CC062]

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Jay Clouse 0:02
I’m here with Casey Allen, the founder of the Enterprise Rising conference. Casey who is Enterprise Rising for

Casey Allen 0:09
Enterprise Rising’s tagline is 100%, enterprise SAS, 100% Midwest and 100% startups. So if any of those click with you listener and sounds intriguing, or better yet, two or three of them click with you, then this is going to be for you. And if you’re an investor, over 50% of the room are startups that are live with revenue, if you’re a founder, all of the speakers are successful founders or active investors. Nobody hand wavy nobody wasting your time. And all the talks are hyper actionable.

Jay Clouse 0:38
How is Enterprise Rising different this year?

Casey Allen 0:40
If you’ve ever attended an online event, you know, networking sucks, slack and discord really just don’t cut it. So we have custom built for Enterprise Rising 2020 an online platform that’s like startup masterclass, meets the Sims, where every attendee has an avatar, you’re in a building, you’re sitting in chairs, you’re sitting in couches, you’re having real video chats with the people next to you. So what we’ve done is we’ve recreated an actual virtual environment where networking happens just like it does in real life.

Jay Clouse 1:06
Casey, when is Enterprise Rising? And how can people get involved?

Casey Allen 1:09
Enterprise Rising is the end of October, the 20th-21st is two full days is all online. So you can dip in and out for as much or as little as you want. Go to That’s, and you can use discount code Upside to score 20% off as many tickets as you want. So discount code Upside at All the details are there, the entire conference is online, it’s going to be a great time.

Ashley Flucas 1:37
My own thing is I don’t usually write more than a couple of pages and look at the deck is always available. But I’m also like my one superpower I’m sure any LP would tell you is responsiveness.

Jay Clouse 1:51
The startup investment landscape is changing. and world class companies are being built outside of Silicon Valley. We find them talk with them and just That’s the upside of investing in them. Welcome to Upside.

Hello, hello, hello and welcome to the Upside podcast, the first podcast finding upside outside of Silicon Valley. I’m Jay Clouse, and I’m accompanied by my co host, Mr. accredited investor himself. Eric Hornung.

Eric Hornung 2:31
We did it Jay. It was all me. We did it. legitimately nothing has changed in my life. The SEC just changed their rules. Well, technically, as I’m recording this, I am not an accredited investor since it is 58 days on the countdown from this recording, until the SEC rule actually goes public. But yeah, man, I have the potential and 58 days to be accredited and actually be allowed to invest in private companies.

Jay Clouse 3:02
They’re like a certificate of authenticity you have to get that you put on your wall like you have to apply for this. What does this mean?

Eric Hornung 3:08
Maybe I will just get maybe I’ll get some commissioned art that just says Eric is an accredited investor. I’ll hang it on my wall, or I’ll hang it on my digital wall. Ooh, that’s a little foreshadow for an episode to come.

Jay Clouse 3:20
You need to put on the wall directly behind you. So I see it every time I record like this.

Eric Hornung 3:25
Yeah. But no, there’s no there’s nothing that you need to have, depending on what regulation D raise you raise under. Your lawyers and accountants may have to sign like a letter to say yes, you are accredited, but usually it’s just a personal attestation that you’re accredited.

Jay Clouse 3:44
Give the people some insight here. They’re probably wondering what’s going on? Is Eric now worth $2 million. Like what’s happening?

Eric Hornung 3:51
No, Eric is not worth close to $2 million. But the SEC for the longest time has said that an accredited investor is an investor who makes $200,000 a year and projects to do so into the future, or is worth $1 million without the value of their home, I am neither of those things. And in order to invest in private companies, you pretty much need to be an accredited investor. There’s some loopholes and ways around it. But for the most part, you need to be an accredited investor. In order to run a syndicate, you need to be an accredited investor. In order to run a rolling fund, you need to be an accredited investor. So the SEC finally came to its senses. Is that a good way to say that?

Jay Clouse 4:33
It’s a very, you’re putting a lot of judgment on that phrase, but yes.

Eric Hornung 4:37
Which is pretty exciting. Well, it sounds like the SEC is helping you live the one life that you have to live the best way that you can, Eric.

Jay Clouse 5:01
Well, it sounds like the SEC is helping you live the one life that you have to live the best way that you can, Eric.

Eric Hornung 5:07
Yeah, just like our friends at Ethos Wealth Management, who are now accredited investors if they weren’t before. And if you want to learn more about Ethos Wealth Management and living the best life you can, you can go to

Jay Clouse 5:22
You mentioned running a syndicate as something that an accredited investor can do. And Eric, we’re gonna learn a little bit more about that here today. Today, we’re talking with Ashley Flucas, an angel investor and the lead of Flucas Ventures. She is the general counsel and a partner at a real estate finance fund, but has also been investing through her own syndicate fund Flucas Ventures for the last two years, Eric.

Eric Hornung 5:49
One thing that I’m really excited about with Ashley is she has so many deals on her site, but it seems like she’s relatively new to the syndicate space from a lead investor perspective. So, I think we’ve had Peter Livingston on and he has spoken to what a mature ish syndicate looks like. This is going to be more of like a startup syndicate almost.

Jay Clouse 6:11
She says she shares primarily pre seed to series a stage deals, but anticipates occasionally sharing some late stage deals. She’s based in West Palm Beach, Florida. She’s been investing since 2018. And like you said, there are a ton of companies listed on her website, that she is invested in herself through syndicates, and now is leading some deals on as a syndicate lead herself.

Eric Hornung 6:38
This is a path that we’ve been trending down here, Jay, where we’ve been talking with syndicate leads, I’m hoping to bring on a rolling fund into the future to talk about that different model. We’ve really been looking at a lot of investment models and dear listener, if you know anyone who is employing a non traditional investment model, or you just are interested on this topic in general, you can tweet at us @UpsideFM or send us something a little longer at and we will get to that interview right after this. Let’s bring in Rob McDonald, a partner at Taft Stettinius and Hollister to teach us about private placements and fundraising. Taft is a law firm known for assisting entrepreneurs across the Heartland. As a reminder, the following remarks by Taft attorneys are for informational purposes only and are not legal advice. This information is not intended to create and receive it does not constitute an attorney client relationship. No person or organization should act upon this information without first seeking professional counsel.

Jay Clouse 7:45
You know, we talked to a lot of founders and we often hear this idea of smart money. How do I identify investors that would be a good fit for my startup.

Rob McDonald 7:54
I always encourage startups to do as much homework as possible identifying potential investors now More than ever, there are plenty of resources available to help founders with this, namely crunchbase angel list and pitch book using these sources. And Google triangulate investors invest in the dollar amounts the startup is targeting, invest in the vertical of the startup and invest in the geography of the startup. Shockingly, the founders can triangulate these three things. Usually, we’re not going to be talking about a huge list of investors from there, develop and use their network to get introductions so that you can avoid fruitless cold emails to investors.

Eric Hornung 8:29
Awesome. And if people want to learn more about Taft or yourself, where should they go?

Rob McDonald 8:33
The best place to go is or my Twitter @RWM

Ashley Flucas 8:38
I’m a lawyer by background and that kind of was not really intentional. It was just kind of I was in college and I thought and as a political science major, so I kind of had some exposure to it and a thought, I’ll have a reasonable aptitude for it and I’ll be in the room. with people who are doing a lot of different interesting things in terms of corporates, VCs funds, banks, and maybe I’ll kind of through osmosis figure out what my passion is. So I started practicing just in 2011. And I ended up going into capital markets law, which has been kind of perfect for transitioning into what I’m doing now. And I started off my career working in London. And that’s what was nice about practicing capital markets is because you can be anywhere in the world because all corporates need advice on you know, US debt and equity markets. So did that for a couple of years. Then in 2013, came to Florida, where in short order I ended up going in house at Real Estate finance fund. I’m actually still there today and balance my, you know, angel investing and syndicate activity with that fund. I’m the General Counsel at a partner as well and In a nutshell that fund, what’s niche about it is we pull all our all our capital from high net worth immigrant investors who are investing pursuant to something called the EB-5 program in the US and kind of similar to my syndicate model, we spin up SPVs relative to specific projects, folks invest in the SPV relative to that specific project. And then from there were more of a traditional were traditional shop in terms of making senior mezzanine loans or preferred equity investment. And the scale of that is, you know, probably like 10 million on the low end. And the biggest singular loan we’ve done was almost half a billion for a project called 702 Times Square and got about 3 billion in terms of total assets under management. So that’s kind of the day the day job a couple of years ago. Literally, I just started thinking about this venture capital again, you know after some exposure to real estate and private equity, and I thought, you know, let me play around with it, and just started angel investing at that point, I kind of started off as you know, Angel list other platforms, you know, a few folks that I knew who were doing it, but you know, I’m in Florida, I’m not in, you know, Silicon Valley. And, you know, and I’m sure we’ll talk about that not the most robust startup ecosystem, but start utilizing some of these, you know, online platforms realize that I was doing it fairly aggressively and kind of had a passion for it. And I think with my background, have a ability to digest a lot of information quickly because there’s a lawyer, you diligence, you write memos, all of that good stuff. Then I just started saying, okay, instead of just saying what comes to be, why don’t I start hunting a bit more, and start getting more aggressive finding deals and switching to more of direct investing as opposed to syndicate investing, and then when this year rolled around with kind of a confluence of a bunch of different things happening on the global environment. I thought one, I don’t often see women or African Americans in this space as investors, as leads, and particularly not on this side of the country, I am of all going off Marie’s relations standpoint and VCs doing, wanting to do more. In terms of equity there, I thought I should do something here and try to be more visible, one just be visible in the space as a woman of color. Number two, I like to think that I don’t have those as well, Nicole, I don’t have those filtering biases. So when I meet a great company, and as an underrepresented founder, I’m looking at it the same way as I’m looking at any other company. And it’s not that my investments are solely in in those types of companies, but it’s just so worked out that in terms of the investments that I have led, there’s usually some team that’s fairly diverse or diverse founder or or that kind of thing. And that’s been really positive. And then I started doing the syndicate model really within just like the last six weeks, but I’m like five deals in. And it’s, it’s been going really well so far. So that’s my spiel.

If I can clarify one thing, it sounds like when you were starting to do some of this angel investing, were you investing into other people’s syndicates on angel list?

Yes, so I was and you know, even though I’ve not been doing it that long, you know, I’ve had quite a few folks reach out to me like, I’ve always been thinking about doing the syndicate like how’d you get started? What were you thinking? And I think the way I started not that you have to wait as long as I did to be a lead, but it was a good way to go about things because I started off purely like Angel invest, I think maybe did like one thing on like seed invest. But it was kind of just like learning like, how does a lead diligence a deal? What information do they synthesize, how do they synthesize You know, just kind of, you know, going through pitch decks and you go through so many of them like even if it’s not a company you invest in, usually take away something in terms of how something was presented, or just learning more about different business models and getting, you know, smarter and that way, particularly, you know, me, I’m a lawyer, but I, you know, I don’t have a tech background, but that doesn’t mean that you shouldn’t be investing in spaces just because you’re not you know, a marketplace expert expert, or, you know, a technologist, you can still get through as long as you can, you know, challenge yourself to kind of build that accumen. So for me, following other folks syndicates, investing via syndicates was like a huge education. And it was also beneficial from a networking standpoint, because when I was ready, you know, to kind of launch my own thing or go more direct and I had, I could speak from a position of knowledge because I had, you know, been involved, you know, I’ll be at indirectly with some pretty cool companies, and then I you know, have felt comfortable approaching those leads and saying, Hey, would you mind backing me? Can I ask you questions if I roll out a deal would you mind you know, taking a look, you know everything else. So that gave me a really great base to kind of accelerate things to the way that I have recently.

Jay Clouse 15:18
You have a ton of active deals on your portfolio page that gets like 115 so when you’re beginning to invest into syndicates, before you said I want to start hunting and start leading, were there any moments or events or companies that made you look and say like oh, this is working and this is like a good return on my time and a good return on my capital?

Ashley Flucas 15:37
That’s a fair question for me I mean obviously it’s it’s fairly early so I mean, I’m not in the it’s not at the point like there’s been you know, some markup or exit wherever I’m gonna where I’m gonna retire but I think it likes it cut off did come together tada as the world was shut was shutting down because, obviously while some portable All companies are not going to do well potentially post COVID there are a lot or a lot of them that this is all an accelerant. So as I kind of saw a few different companies that I had a thesis about, but that, you know, might have been a couple of years early and then seeing the velocity at which that kind of picked up around you know, even as early as March, April, I’m like, okay, like I can kind of see like, what happens like when you get out of that first gear, and you just keep you keep growing and then something some other in some other companies, like, for example, investing in both and just seeing like, you know, year on year, how much the growth in terms of the volume of transaction processing and being being able to see that and you’re like, Okay, this is like you see, kind of the snowball effect of things. And then as I mentioned, like the things that are subject to COVID accelerant, like one portfolio company, for example, like touring Which is focusing on remote work. I mean, I always thought that made sense, but now they’re kind of looking like geniuses with the world the way it is. So yeah, that’s that’s kind of been the experience.

Eric Hornung 17:11
How many of those 115 deals have you run through the syndicate versus were direct angel investments or indirect angel investments?

Ashley Flucas 17:21
So as I said, the lion’s share when I initially just started was me going through other folks syndicates, whether that’s Angel list or, you know, folks that I know off flat platform and we’re pulling things together or Angel groups or whatever else. But I would say from a ratio standpoint, probably something like a quarter are in the director, syndicate model and from a distribution standpoint, now it’s much more loaded towards direct and syndication. I will of course invest in a syndicate if it’s a great deal. Why Why will die but I am more focused on a direct model and, and things I can say syndicate but like I said, I, the syndicate itself, just really launched like within the last six weeks, and I’m five deals and with with three close one closing out and one on one about the launch.

Eric Hornung 18:13
How do you think about investing in a company looking at an investment opportunity, when you’re making an angel investment on your behalf versus on a syndicates behalf? Is there any difference in the investment due diligence or memo or anything that you do differently between the two?

Ashley Flucas 18:30
There are a few different dimensions along where it’s different and one thing which I try to carry over and be really mindful of, particularly, you know, since I’m, you know, experience with whatever again, afon granted, a real estate fund is not get addicted to the lure of other people’s money, you still have to and I and based on some deals I see. I don’t think everyone that necessarily follows that standard, but I really try to earnestly ask myself When I evaluate a deal, if I were the one writing a check for maybe the size of the total allocation, would I still write this check personally, and I have to answer myself that every time or there is arguably not not not a great deal, if I wouldn’t take that if you’ll provide it, I had the ability to write that size, check, whatever, whatever it is. So that’s kind of number one. And I and I, and I try to always go through that mental exercise. The second second aspect of it and I always say this, when I’m talking to founders, particularly you know, in recent weeks is I always still first look at the deal as a personal investment, and I co invest, you know, in the vehicle, granted, maybe the cheque size isn’t as big as when it’s a purely personal investment. But I always try to first filter it through that personal investment standpoint. And I say, you know, sometimes things make sense for me personally, that I just don’t think resonate from a syndicate level. And that could be because you’re kind of really early on. So maybe you don’t have the kind of strong signalers that might resonate with LPs in terms of institutional VC capital, or it’s really great product, a lot of things are aligning, but it’s just a little early, maybe from an HR standpoint, those kind of things. But you know, it might be within my risk profile. And so maybe I’m willing to write a decent sized personal check. And if that’s the case, you know, I’ve had some good conversations where I could say, look, it’s a little early for the syndicate, because this is kind of like they like fast balls down the middle, solid traction, great VCs, all of that stuff. I my risk profile is a little a little higher, and I’ve got the ability to play around a bit here. So why don’t you let me come in personally, whether it’s this round or the next and some of those other signalers, let your signals fill in, then I’ll bring it to the syndicate. And that’s It’s been a pretty good compromise so far.

Eric Hornung 21:02
How do you know what your LPs or backers like? Like what’s the onboarding process to become an LP of Flucas Ventures?

Ashley Flucas 21:12
I’ll be honest, like, I’m still evolving in my learning on that, because it’s a bit of it’s kind of like you’re a mad scientist tinkering. Like, you know, you might get something and you think this is can’t miss, this is the thing, it has all the signals, and you’ll get the deal done. You’ll get it close. You’re like, man, I was thinking I was gonna get, you know, quadruple that same. And then by the same token, you put out something you’re like, you know, I’m putting it out. I believe it’s a good deal. I’m expecting, you know, maybe I’ll get 100 grand or 150 grand, and then it’s blown past 500,000 and you got to scale people back because you only have so much allocation. So I’m still tinkering kind of learning that in terms of the LPS, I mean, at this point in a rather short order, and probably some of that is the nature of angel list. I’m at home 400 LPs so it’s just not possible to individually manage every relationship. But what I do try to do is whether it’s reaching out or being responsive when LPs reach out, if I’ve got a free moment, I’m just always chatting with them and doing my best, particularly for folks who are who are active, you know, in this world to let’s just chat for 15, 30 minutes or someone invest in a deal or even maybe someone rejects a deal, I’ll just send them a note saying, Okay, this wasn’t in your wheelhouse, like kind of what’s what’s what works for you, just so I can keep an eye out in terms of flagging for you the next time I see something that’s within that space, or even if you know, I get a deal, and I don’t think it’s right for the syndicate, but like, this is really your lane. I was like, I’ll send it to you, maybe you can direct invest. So it’s a lot of that. Just the tinkering. And then you know, you know, these are smart people asking great questions. So some even just the questions they asked you, you can kind of reverse engineer Year and figure out, Okay, this is what matters. The next time I come out with a deal or a memo for this sector, I should really make sure from a diligence standpoint, I’m covering this or at least from a memos standpoint, flag this because these are the details that resonate with them.

Jay Clouse 23:18
Something that you you mentioned a second ago that got me thinking when you’re considering sending to the syndicate or investing yourself because maybe the risk profiles a little bit higher, and you know, that’s a better match for yourself. How do you think about, like your hit rate of I sent this deal to the syndication and it got filled or didn’t get filled? Are there any best practices or even guidance from angels to say, you know, you want to have this this high of a conversion rate of going to the syndicate with a deal and actually closing it.

Ashley Flucas 23:48
So knock on wood, I think it’s an end eventuality with the syndicate model, but so far, I’ve not had a deal that hasn’t filled that I’ve just been very fortunate from, you know, kind of The ogis on the platform who I’ve talked to like you, you’re not going to have 100% success rate. So that’s just going to be an eventuality. So I kind of learned more from talking to other people, like, how do you deal with that? And that’s like you said, that’s the nature of the model when I put a deal out, and no control over the velocity of it and the ultimate amount, so you need to really, really be sure there and one thing that I’ve tried to do to backstop against that, and I actually did it this morning, but before the call, is if I see a deal, and I’m like, this is a great I think this is a great deal potentially, but I’m just not sure if I’m gonna get there from an allocation or from a from a subscription standpoint, or if I should be even though I think it’s a good deal or if I should be the voice for this particular deal. There might be another lead on the platform who is you know, the prop tech or fin tech CEO or product lead and if that person puts this deal out. I think it’s almost a no brainer that it’s going to subscribe. But you know, for me, you know, I’m learning what people think that I’m an expert. And despite what I might say, I’m an expert in so I think people are starting to perceive me as being strong and lat AM, even though I didn’t set out to do that. It’s just, I put out a couple of deals just because I like them. And they’ve just gotten a great response. So like I said, I had an example. This morning, I saw our prop tech deal. I was like, wow, I really like that. I obviously have a real estate background, but I just don’t know on a couple of items, how I’m going to position this and so I have an LP, who’s also a syndicate lead, and he’s the CEO at a prop tech startup. So I was like, You know what, I’m just gonna I’m gonna shoot it to him get a second set of eyes. See what he thinks he’s like, No, no, this is actually a really good deal and I’m and obviously shooting it to him knowing he’s going to be a strategic Potential fit for the company, and kind of my attitude. And I hope I always keep this is that, yes, I’m not doing this for the good of my heart. But you know, so early on starting out, like relationships matter a little more than, you know, getting every possible point that I can. I’m very open minded about kopko syndication as well. And if I see a deal, and I just know it’s really suited for someone else, who’s also very strategic and I know that because I back a lot of syndicates and I backed a lot of deals, so I kind of have a feel for some of the stronger leads where their thesis is, like, fine, like I’ll do the deal together, share the carry all of that because it’s going to get it done. And you know, more importantly, it’s going to help me in my education, my process, and I’m going to help that founder as well because if they can get folks who are that caliber to evangelho sighs about what they’re doing. Obviously, that only helps me because then you know, at least somewhere it slightly increases the likelihood that they’ll have some long term success.

Eric Hornung 27:05
I love that concept of I’ve never thought about this in a syndicate where in like the startup world, there’s the classic founder market fit or founder, product, product market fit. And in syndicates, there’s almost like lead deal fit. That’s super interesting. You mentioned share carry with co syndication. Can you talk a little bit more about how tactically co syndication works? Like, is it a informal agreement? Is it something structural? Is it like, Is it just naturally? Is there an industry standard where it’s a split 50-50? Or you get two points, or how’s that work?

Ashley Flucas 27:41
I can’t say that. I know what the standard is. I mean, I think it’s just a conversation like you have to be comfortable having, you know, up, you know, up front and there could be a variety of factors, right. So, if you’re going to be if you brought the deal if you’re carrying the laboring or all of that, if you’re doing The memo and all of that and someone you know, they’re a great fit, but you know, maybe they’re not pulling as much on it, then maybe you work out some custom, you know, some custom thing, maybe you’re taking two thirds or taking a third, generally speaking for myself, and it’s, I think it’s more of a standard, if I’m reaching out to someone for close indication, it’s because I expect that they’re going to be able to provide a lot not just in terms of bringing their LPs but because this is someone who I want the company to be, you know, connected with, and, you know, through the, whatever the lifestyle of the lifecycle of the company is, can work with me and be a sounding board or we have issues that crop up with the company or fundraising, that can really be a you know, kind of a special partner with respect to whatever that company is. So for me, generally speaking, my default is, you know, we’ll just go even on it unless there’s some other circumstance that dictates that we should shift one way or the other

Jay Clouse 28:59
Can you explain to me how you think about deal memos? We talked about deal memos on the show, but we haven’t really like dug into one. So when you’re writing a deal memo for your syndicate, I’d love to know, one, how much time that actually takes into what you include in those deal memos.

Ashley Flucas 29:18
Yeah. So again, this is another one of those things where I felt like I had some great advantages going into it because by the time I started my own syndicate, I’m sure that I probably read 1000 deal memos at some point or in between memos and deck. So I had my own strong personal view about what are the strongest memos that I read or in certain deals particularly like some of the stuff that’s not in my wheelhouse, like, you know, I like it did a deal for like a time series database. I’d never heard of that in my life before that deal, and still did it but like the memo was just so much Strong in terms of like, okay, explain it to me like, I’m five. And I’m like, okay, like, I don’t know really much of the technical stuff. But Wow, I really get why this is a problem for companies and why you need this and and the scale you need to do it at. And then I also really understand the solution you’re putting forth and the team based on what they’ve done in similar companies, why they’re the guys to do it. And it got me past it. And I could probably point to, you know, several examples like that. And I just kind of always mentally kind of collect those examples. So candidly, when I went to do my first like, I went back because you could still look at deals that you actually invested in, which is even great as a filter, and some of my favorite deals and I just kind of I read the memos for a while and I kind of pulled out what are the things that got me there and then I kind of put together before I ever even had a deal, kind of put together a template of I always want to hit you know, these various things. I mean, obviously In today’s world, for example, I’m always going to talk about COVID impact good, bad or how they’re mitigating mo is going to talk about the advisors and the CO investors, I’m always going to talk about what shingling product market fit. And a couple of other things like that. I’m always going to make sure I kind of do the too long don’t read at the beginning to give people highlights because everybody’s busy professionals. And sometimes you just see the highlights and you’re like, we’re flipping few pages of the deck and you’re like I and see what the core investors are. I’m know I’ve been guilty of this a couple of times and say, I got everything I need here at least to take a flyer on it. So I always have my highlights. And I’ll geek a bit with you know, go down and explain a bit more for the folks who really want to dive in. But my own thing is I don’t usually write more than a couple of pages and the the deck is always available, but I’m also like my one superpower I’m sure any LP would tell you is responsiveness and I’m an intuitive Zero kind of person. And that’s probably from days, being a firm lawyer like carrying a blackberry back in the day. So if people have questions, I get back and rapid water. So and that creates a nice dialogue and generally leads to if someone usually engages me in a question I’m finding, there’s like a 95% conversion rate, they then go on to invest. So I don’t mind the memo not being worn piece because I like having that engagement with investors. But back to your first question, how long does it actually take because now I’ve, I’ve done a few of these, I kind of have my template. I mean, to be honest, once I’ve had the conversation with a founder, and I always take notes during those calls. So I look at my notes, I look at the deck, maybe some press or collateral and I kind of just go through source by source and fill in, fill in the memo or maybe even redline and all kind of memo and then add things that are unique for me probably like 90 minutes, to be honest. And I don’t know if that’s slow or fast, that’s just kind of that’s kind of that’s just kind of me. And I’ve even heard of some leads who have like, even like interns or MBAs, or who are writing that. And I mean, that’s interesting, maybe in the future, but for now, I enjoy just kind of getting my hands dirty. And you know, I’m a lawyer, so I’m kind of used to, you know, cranking out stuff. So it’s okay so far.

Jay Clouse 33:25
I would love to hear somebody listen to the show. We’ve done two shows now about syndicate investing you and Peter Livingston. And there are some listeners of the show who are certainly in a position to join a syndicate, maybe even start a syndicate. But let’s start from the join side. If I’m going to enter basically your shoes A few years ago, beginning to invest into syndicates, how would you advise them on getting started? what to look out for? How much to allocate all those types of questions?

Ashley Flucas 33:53
No, those are excellent questions, because obviously I learned a lot by doing man if there’s so Things probably if I had If I had known it might have accelerated things, but you know everything in due course, one I am, I am a big fan of angel lists. Some folks are some folks are but I think if you’re outside of Silicon Valley, I just don’t know or New York, I just don’t know how you could break into this world without it just because of, you know, the density of folks that they have on there. And just the way it’s it’s set up like, it just makes sense, particularly if you’re outside of Silicon Valley, and you can’t really pound pavement because I’m in you know, South Florida and I frankly, I frankly can’t know the only thing about Angeles is is if you get on it’s not necessarily like you there’s like a way to kind of do you join and apply to syndicates and you can you know, click on syndicates and read a little bit more about their investment, but you don’t really necessarily know like, is this a great this is a good syndicate that I should follow. Or there’s hundreds of them and who’s active and who’s in my wheelhouse. So that tends to be a little more manual. I think one way, in my own experience some people have shortcut is, so many people are on, in fact, on Angel lists. So maybe you have a friend that’s on it or someone you feel comfortable reaching out to that you could see clearly from their profile that they’re active on Angel list, and just kind of make the ask which people ask me all the time, and I’m happy to do it, which is, I can’t opine on every syndicate. But from my own personal standpoint, here are here’s a list of 10 that I think a great deal high volume, good people responsive, will go back and forth with you get started on these folks until you get comfortable and then just kind of let it build organically. And then the other pieces of advice I would give for you know folks getting started is just be judicious about how often and how frequent you’re investing because it’s almost like go Way to the casino in some ways that first like, you do it and you hit the button the first time and you’re like, I just invested in a startup. I am equity, what if it goes on to be Uber itself? And it’s probably not to be honest, that’s just the, you know, the law of averages there. But it’s hard not to if you’re passionate about this stuff, like not get addicted, not want to invest in everything you see, or come out the gate with really strong checks. And I’ll tell that because I’ve had some folks that I brought from offline Angeles and they’re like, should I put x in the deal? And even though it’s counter to my interest, I’m like, absolutely, no, you should not because I’m going to be offering a lot of these and I think you shouldn’t pay in spray but at the same time, you should personally kind of index be exposed to different sectors, things with different timelines, maybe some different stages and kind of treat yourself in your investing as you would you know, your stock portfolio. So yeah, I was like don’t be so over eager that your first deal that you see that you like you write a check for, you know, depends on what your means are, but you know, 100 grand, and then you’ve got, you know, 10 grand left for the rest of the year in terms of what you want to allocate to start up. So you know, take it easy, and for me, my own philosophy is, so far, I always keep my deal minimum really low, which is the minimum they require, which is 1000. Because I want to democratize access. I want folks who say maybe this deal is early, so maybe I don’t want to write 10, 20 30,000 but I’ll take a flyer and you know, from what I can see so far, all the LPS are quality and value added I want them and I want them in my deal and part of the network. So and and those things as you build you scale your network, those smaller checks add up and make as much of a difference as the bigger ones. And then I think the other thing I’d say to people is social proof, isn’t it, it matters I mean, you know, most of the returns go in the VC funds. So if you’re, you know, like, cousins friend sends you a deal, you shouldn’t, you should look at it very carefully and probably those aren’t the deals that are appropriate for this world. But at the same time, there are a lot of brilliant funds that have invested in however many unicorns, but you don’t always get to hear about all of the spectacular failures as well. So when you see a deal, and maybe you have a certain expertise, whether it’s you know, real estate or whatever, and you know, like, these, like margins or unit economics or whatever else just don’t make sense. Or you’re kind of out of the Silicon Valley echo chamber. And, you know, this doesn’t make sense for people in the real world. And there’s a lot of deals that are hot deals in the valley that are putting forth things that just don’t resonate with how people live on the real world or mainstream or, or mainstream or what’s even in the realm of affordability If you feel that do not override your gut and don’t just invest in it because a really great VC love to check in it.

Eric Hornung 39:08
Are there any third party syndicate evaluation groups or fund due diligence groups?

Ashley Flucas 39:14
So I’m a member of a couple of angel groups like angels and life science angels. So those, I guess, in the sense of those Angel groups and like I’ve had scenarios like particularly like things in like biotech and life sciences, I’m like, Look, I have exposure to those deals. I happen to like those deals, because there’s a lot of IPO and m&a activity. And if it’s not developing a therapeutic end to end and has some kind of FDA Fast Track angle, for example, you might actually be able to see an exit much sooner than you would in tech. So I like them. But you know, I, they could tell me anything in terms of like the technology and the science and I’m not going to know so for deals like that I will go to like, you know, but those Angel groups like life size Angels that say, great deal, I’m not gonna syndicate it or invest in it yet, because they could be saying anything. But you guys are all physicians, doctors, professors, work for pharmaceutical companies, you’ll be able to do that part, I can ask them the questions that I like to ask. And then we could figure out if this makes sense. And I know a lot of, you know, some of the angel groups, they all operate different ways, some kind of like, the heads that those Angel groups just kind of push out deals and maybe there’s some q&a is taken or leave it. And then there are some where there’s actually like a real collective collaborative due diligence. So that’s a great way and I should have mentioned that as well besides Angel list is, you know, do your research, find local or remote Angel groups, then look at their portfolios and say, hey, that’s something that I would have invested in and just reach out and see about joining. They all work differently. Some charge a carry, but there’s no membership fee, some charge a membership fee. There’s no end, but there’s no carry. So you know, you’re saving compared to if you were investing in syndicates, but then you got a network of people who, you know, are looking at the same deals for, you know, like the angel invest. And those are people you can learn from or get mentorship from, or bounce things off of.

Eric Hornung 41:19
How about third party groups like I’m thinking about, like Cambridge, they look at all of the top venture capital funds and go do an evaluation of them or fund Evaluation Group. They look at all the hedge funds, so that LPs have some third party to turn to Is there something like that in the syndicate world where someone goes around and evaluates each syndicate lead and issues a report or something to potential backers?

Ashley Flucas 41:45
That’s a really interesting question. Not to my knowledge, but then now, you just gave someone their next business. That is probably inevitable, because you know, as you know, for folks trying to figure out who to back is a syndicate All you really have is like kind of this like hodgepodge of different sources. So you can look at their LinkedIn, if they have a website, you could check it out, but not everybody’s gonna have a website. And that’s all you know, that’s coming directly from them. You can Google but not everybody is going to have a rich internet history. Within the context of angel list itself. You can see their Angel list investments and, you know, once they close, you can see the deals that they’ve LED and kind of get a feel, but that’s kind of as best as I think you can do. Or at least I’m not privy to somewhere the source where you can go and, you know, there’s like a league table of the top syndicate leads but sure, this sector would would would welcome that. You know, just kind of like they do it. Guess it’s not really the same. It’s not the same because I don’t really know what criteria they use. I think it’s like Forbes or fortune that does like the Midas list, which is like here, the top, whatever 182 Investors but it’s kind of opaque about how they’re deciding that other than presumably they had a good exit. So unfortunately, that doesn’t exist. But you can kind of use some of these other things as a as a proxy, if you look at their deals, deals they’ve been in, like I said, and their background and go from there. And that’s why I think the social proof becomes important as a syndicate lead because hey, maybe they don’t know if you’re an expert in FinTech, but maybe you know, maybe Pay Pal ventures is investing. So then the LPS are like, I’m pretty sure they really kick the tires on this. I feel really good about the diligence because of who else is on the deal. And because you know, syndicates tend to go fast. A lot of times, you know, you’re syndicating and your last money and you’re wrapping things up, maybe you’ve only got a week, maybe even less to wrap up commitments. So there can’t be this, you know, long drawn out process. So That’s when the investors are going to look to those other signals like particularly said the social proof and say, okay, it’s marketplace. I don’t know Ashley, if you know anything about marketplace, I haven’t done any deals where yet we’re there in it as a lead, but you know, if they saw fJ labs, they’re something they’re like, okay, yeah, yeah, they know what they’re doing on marketplaces. So this is this is probably pretty solid in terms of the diligence that’s been done.

Jay Clouse 44:26
You you said about six weeks ago, you started your angellist syndicate. How are you thinking about your own goals and you know what you hope for that through the end of the year or to the next two years? What type of goal structure do you have for your own syndicate?

Ashley Flucas 44:42
Kind of my approach, I think of continuing the same approach which is made me happy and be personally a fit fulfilled in that. I’m just kind of letting it be very organic like it started out as syndicates. Then it started then it went to direct then it went to leading syndicates and I just kind of keep an open mind, always look for opportunity. But I’m not putting any real specific goalposts in terms of, I would like to have raise X amount of capital per year, I need to do fund X amount of deals per month or per year or by 2022. I need to raise a fund. It just wanted to be more organic, because, again, want to keep my ears and eyes open. Because if I do that, then whatever that next step is, it’s going to come You know, it’s, it’s all going to kind of clear up and come into place what the next step should be. I will say, because obviously, we’re working in a real estate fund in a shop that’s more institutional. I’m not sure if that’s what we’re I want to go but I mean, I’m open to it if that’s where it all leads, but right now, I’m having a ton of a ton of fun and learning a lot about it a lot. I was one of those people who thought I’ll just be chasing kind of checks. Because I’ll never really be passionate about anything like it’s all kind of widgets to me. But I found that yeah, that’s because I like this. I don’t I’m not. I’m not an operator. I don’t want to be an operator. But I do love investing in startups. And it aligns very much with my personality. So I think I’m just going to keep doing this for a while then and just kind of see see where it leads me.

Eric Hornung 46:27
He’s talked a little bit about, especially outside of the valley, and you mentioned Angeles is a great place where you can’t, you can’t pound the pavement. We heard from Peter on a previous episode, that his LPs weren’t exactly thrilled with him being from Florida, so much so that he said that he moved to the Bay Area to launch his syndicate. Do you feel any of that same or similar pushback from your backers, and LPs?

Ashley Flucas 46:52
Oh, that’s really interesting so far. No, it hasn’t. It hasn’t come up but I also can be, you know, the timing of when I got started, I had a couple of things working for me one, a, at least for the moment renewed interest in hearing from voices outside of Silicon Valley on terms of geography, race, gender, all of that. So that’s, I think, been a permanent part and accelerant for me and people who want to get behind it. The other aspect is we are now in a zoom world and we can’t go grab, we can’t go meet you know, what a members only club or, or grab lunch or a coffee. We’ve got to fire up our laptops and make it work globally. I can’t go talk to startups in Silicon Valley, even if I wanted to, and business still has to get done and I’m able to manage those conversations remotely. So I think there’s probably I it’s been a bit fortuitous that I’m starting when I start because it’s now accepted that you don’t need to be you don’t need to be on the ground so much Great and and I guess so that was one part of the impetus for me getting started as well. I’m like, okay, like I’m not dissing geographically disadvantaged anymore because I can talk to, you know, someone in India or Silicon Valley or Austin and it’s it’s, it’s fine and we accept this is how we communicate. So I have not had those issues. I will not be moving to Silicon Valley Even if my LPs say they’d like me to be there and move on to something else or stick to real estate, I guess because I love being in Florida.

Eric Hornung 48:35
What do you think has been more successful in creating jobs in the state of Florida? The EB-5 program or startups?

Ashley Flucas 48:44
Obviously, you’re pulling it to different heartstrings there but my honest answer is EB-5 one because I have internal data just about the number of jobs that we have created in terms of construction jobs on to some of the companies Some of the projects that our real estate portfolio and it’s it’s tangible real estate is enormous business in Florida and a lot of folks take advantage of EB-5 financing. And you can see, like I said, particularly on the construction side and then some of that support stuff engineers, lawyers, architects sales folks as well. There’s a lot of well documented evidence of that and you know, there’s a condo or, or a medical facility that goes up every two seconds in Florida, this startup ecosystem I’m having having some interesting conversations because there’s a lot of money in Florida. There’s a lot of family offices, there are a lot of real estate magnets, but there’s not you know, there’s still evolving in terms of who are the go to funds here and you’re seeing like some snowbirds come down. And there’s no reason particularly being a gateway to Latin America. Why, you know, this corridor shouldn’t absolutely be booming, at least maybe comparable to how you know, Texas is Rising it just takes someone doing that and and and making that effort. And so while I was still, obviously I’m open to startups everywhere, but that’s something that’s been in the back of my mind as time permits in terms of one of those next kind of like doors to try to open up his, his being more conscious about what is in my own backyard, whether that’s, you know, startups based out of South Florida or just deepening in terms of ties to lat am because it’s definitely under harvested here.

Jay Clouse 50:36
Awesome. Ashley, it’s been great chatting with you here. If people want to learn more about you or your syndicate, where should they go after the show?

Ashley Flucas 50:43
Obviously, if they’re on angel list, they just have to search my name, which is Ashley Flucas or the name of my syndicate, which is Flucas Ventures. I do have a website, which is where you saw the portfolio, which is just Or they can look me up on LinkedIn, LinkedIn, and there’s information there about the syndicate and getting involved. And generally, I’m kind of not one of those people. I don’t treat LinkedIn like it’s like, you know, a social network and I’m only connecting with my friends. People reach out to me on LinkedIn all the time out of the blue. And, you know, some of it can be a little spammy. But sometimes it’s really awesome people. So you’ll ping me there. And there’s a very good chance that I’ll want to strike up a conversation about any and everything venture capital.

Eric Hornung 51:33
Alright, Jay, we just spoke with Ashley from Flucas ventures. Here’s my question for you. Do you think six weeks into launching a syndicate? You could have over 400 accredited LPs?

Jay Clouse 51:44
No, me personally.

Eric Hornung 51:44
Yeah, you personally, me either.

Jay Clouse 51:46
I’m either really, really good at it. I mean, that’s even if I’m thinking like, Okay, how would I make that happen? We’ve built a pretty good network here, but that’s still like a lot of hand to hand combat just like personal high level outreach. So super, super impressive, which isn’t surprising given you know what we said from the outset, Ashley has a ton of deals that she’s been involved in, in some form or another, and not your typical investing background. It seems like she just, you know, built an independent interest around this and saw how she could start investing into syndicate deals herself and has been really running at it for the past couple years.

Eric Hornung 52:26
Her answer to it usually takes her about 90 minutes to write an investment memo blows my mind. I mean, that’s so impressive. To be able to look at a company see the documents think through everything. I mean, we do it on a 60 minute call here, but we’re not diving in and actually allocating anybody’s capital our own or others. So to be able to be confident in 90 minutes and then have the understanding from actually being an investor to see what investors want to see to the point that she said she hasn’t had a deal. That hasn’t been filled.

Jay Clouse 53:02
Crazy. I have to think her legal background helps, too. Because I mean, if I was investing into a syndicate somebody with a legal background who could look at the deal from both a finance and legal perspective, that’s really compelling to me. It’s a different viewpoint that we hear a lot of times.

Eric Hornung 53:18
See, that’s interesting, because one time you told me that my emails sounded too much like a lawyer and that you thought they turned you off.

Jay Clouse 53:24
Well, yeah, but you’re not you’re not advising me on the legal aspects of something you were like

Eric Hornung 53:31
Inviting you to a fancy Fantasy Football League.

Jay Clouse 53:34

Eric Hornung 53:36
Speaking of email, one of the things that I love that she said and that I am incredibly jealous of is she said her superpower is responsiveness. I just pulled up my inbox and it is a mess. I would love if my superpower was responsiveness.

Jay Clouse 53:52
Are you still using Hey,

Eric Hornung 53:54
I am still using hay and it’s phenomenal because it helps me get through all of the all of the things. I don’t need to respond to Get put off to the side. And I can kind of browse at my own leisure. But I do have a very large Hey, get to this pile right now. And that needs to happen.

Jay Clouse 54:10
So Eric, this is we started this interview talking about you being Mr. Credit investor himself. How difficult does it feel to you sitting in a position where it’s like, oh, I could probably start a syndicate right now, to get to the point that Ashley is right now, like going from zero to where she is now that you technically have the ability to?

Eric Hornung 54:28
Does that seem doable? It seems doable. I don’t know that without doing 100 deals on your own, it would be as quick. But I think that if you have this interest and you’re willing to dive in and you’re willing to spend time on it. Yeah, I think it’s doable. I think that the syndicate lead style and the benefits she mentioned that if you want to start investing in syndicates, or if you want to be a syndicate lead, the best place to start is with Angeles because it’s a platform so it’s going to help you with discovery is going to help you With a lot of things that are harder, so it’s doable. I think it would be very hard. I wouldn’t be able to do it part time while I’m also a general counsel at a real estate investment fund, that’s for sure.

Jay Clouse 55:07
Yeah, super, super impressive what she’s doing. Like Eric said, We’d love to hear from more alternative finance ears. So if you know somebody in the space leading a syndicate or doing something different, like a rolling fund, we’d love to hear from you. You can tweet us at upside FM, or email us And we’ll talk to you next week. That’s all for this week. Thanks for listening. We’d love to hear your thoughts on today’s guest. So shoot us an email at or find us on Twitter at upside FM. We’ll be back here next week at the same time talking to another founder and our quest to find upside outside of Silicon Valley. If you or someone you know would make a good guess for our show, please email us or find us on Twitter and let us know. And if you love our show, please leave us a review on iTunes. That goes a long way in helping us spread the word and continue to help bring high quality guests to the show. Eric and I decided there were a couple things We wanted to share with you at the end of the podcast. And so here we go. Eric Hornung and Jay Clouse are the founding parties of the upside podcast. At the time of this recording, we do not own equity or other financial interest in the companies which appear on this show. All opinions expressed by podcast participants are solely their own opinion and do not reflect the opinions of Duffin Phelps LLC and its affiliates on your collective LLC and its affiliates or any entity which employ us. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. We have not considered your specific financial situation nor provided any investment advice on this show. Thanks for listening and we’ll talk to you next week.

Interview begins: 8:44
Debrief: 51:53

Ashley Flucas is an angel investor and syndicate lead with Flucas Ventures.

By day, Ashley is a general counsel/partner at a real estate finance fund (infrastructure, sports arenas and large-scale condo, apartment and commercial buildings) with approx $3B AUM (LPs are overseas HNWIs).

By night, she is an active angel investor who has participated in more than 100 deals through AngelList and direct investment.

Flucas Ventures is sector and geography agnostic primarily focused on pre-seed to series A-stage deals, but occasionally sharing compelling late-stage deals.

Learn more about Flucas Ventures:

Follow Ashley Flucas:

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Key points:

  • Moments when there are good returns 15:18
  • Difference in the investment due diligence memo 18:13
  • Onboarding process to become an LP of Flucas Ventures? 21:02
  • Co Syndication 27:05
  • Deal Memos 28:59
  • Advice on starting out 33:25

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