Mark Wickersham, Host 0:05

Hi and welcome to the Wealth Tech Podcast. I'm your host, Mark Wickersham. Today's episode, I sit down with Frank Tumminello, CEO and Co-founder of FileForms. FileForms is a compliance and entity management software that helps family offices meet entity filing deadlines at the state and federal level. Frank and I dig into the operational chaos that many family offices face when managing dozens and even hundreds of entities around fragmented relationships, unclear roles, and heavy reliance on spreadsheet. Sound familiar? We unpack where File Forms sits in the broader Family Office Tech Stack, some of the common horror stories that happen without a centralized compliance solution, the current state of the CTA, how AI is being applied to entity management and compliance platforms like File Forms, and where the Family Office is heading over the next three to five years. As always, we end the podcast on a personal note with three questions that have nothing to do with WealthTech. Let's get started. All right, Frank, welcome to the Wealth Tech Podcast. I am happy to have you on the show. Would you mind kind of giving a brief introduction of yourself and Fileforms?

Frank Tumminello, FileForms 1:23

My pleasure, Mark. Thanks for having me today. And uh thank you for all the listeners out there tuning in. Uh, my name's Frank Tumanello. I'm CEO and co-founder of Fileforms. Uh File Forms is a software company focused on state and federal compliance in all 50 states, uh, largely partnering uh with family offices, uh, professional services providers, and business owners to help them keep their legal entities compliant in all states they operate in. Um our platform is providing services such as company formations, such as LLCs, uh, that are getting incorporated for the first time, but really all the entities that already exist, specifically in the family office realm, that need to be kept in good standing across all the different states that they operate in, with the registered agent filing an annual report each year. So that's a little bit on our company and very excited to share more.

Mark Wickersham, Host 2:21

Yeah, as we had a chance to talk earlier, Frank, you know, Frank, family offices love entities. Uh they create a lot of them, and and obviously there's a lot of filing that that goes on with that. So it's great to hear that there's some solutions for that. Tell me, why did you start file forms? What was the genesis for creating the company?

Frank Tumminello, FileForms 2:40

Yeah, um, I started file forms after running into the exact problem that we now solve. Um when I was actually working in my prior role at a financial services focused private equity firm, I was uh managing my my very first legal entity on my own to hold a real estate investment that I had made. And uh turns out I missed my annual report and had to pay the fine. And the frustrating part wasn't just the the miss of a of a an arbitrary date, uh, but actually it was realizing that there wasn't a modern solution uh for folks like myself, professionals that um were trying to really take their first entrepreneurial leap at that point in my career. And uh, you know, came to realize that you know it would be such a nice benefit uh to have a reliable way uh to keep track of state filing obligations across all entities and all states. Um at the same time, uh I realized that uh there was somewhat of a gap for entrepreneurs versus the investment operators, um, where the investment operators, you know, a lot of times are managing multiple legal entities across many states. So um once I kind of took some interest in this industry, I started talking to my CPA friends, my attorney friends, other professional services providers and investors. And uh it came to my attention that they were very much relying on spreadsheets, emails, fragmented vendor portals uh to manage annual reporting and registered agent services and even their company formations. So to me, that felt like a real opportunity, hence why we built file forms.

Mark Wickersham, Host 4:22

Uh yeah, it does it seems like a common story, regardless of what vertical you're in with the family office space, is is too too much reliance on on keeping stuff in people's heads, too much reliance on email and and spreadsheets versus systems. Um you've been at it just a little over two years. Uh what lessons have you learned as a as an entrepreneur? I would love to talk to the founders when I have a chance. So, you know, what what are some of the, you know, what's something that surprised you um that maybe was a little bit easier than you thought? What was a little bit harder than you thought it was going to be?

Frank Tumminello, FileForms 4:58

Yeah, I think the biggest lesson so far is just listening to your clients relentlessly, um, listening to their pain points and really setting expectations early on to drive the highest impact work. Um really, there's a ton of different things a customer can ask for any given day. And we obviously want to solve all pain points we can. Uh but in compliance, as much as there is a lot of predictability, uh, there is uh certainly things that fall outside of our control at times, such as state portals going down or the IRS EIN site uh being uh you know in maintenance mode. Uh so I think, you know, really listening to clients, understanding their pain points, communicating very clearly up front, expectations is something you learn early on as an entrepreneur, and I think it makes all the difference. Uh the other major thing uh is is about uh product discipline. Um there's always a lot of nice to have features out there, one-off requests. Um like I said, we we definitely are people pleasers here at Fileforms. We want to make everyone happy. Um but but really progressing those features and prioritizing um those outcomes to reduce workflow and make the most efficiencies for the most amount of people is certainly how we approach our work every day, um, especially when serving family offices that have a super high bar um for what technology can do or how things should be done and uh supporting their employees to make lives easier.

Mark Wickersham, Host 6:32

So yeah, I always say that the hardest thing with with uh product management is it's not figuring out what to do, it's figuring out what not to do when. Yeah, that that saying that that Steve Jobs saying that they you know he said you know says no 300 times before he gets to it, I guess, is is key and kind of really focusing on solving kind of particular pain points. How have you seen clients' expectations evolve? I I know it's been a short period of time since you've been in the marketplace, but how have you seen family offices, what they're coming to you with, and what their expectations are about your abilities?

Frank Tumminello, FileForms 7:10

Yeah, you know, I think expectations have have certainly uh conformed over time. I even remember uh working in the private equity firm that I was working at, which was a mid-sized firm, small back office, a lot of those same pain points that a family office would have from an administrative reporting standpoint. But, you know, I think you know, early on, many folks uh were really just looking for a solution to get the work done. So just need to need to file it, just want to get it off my plate. Today, especially with family offices and professional services providers becoming more modern, uh, managing larger portfolios, doing acquisitions, um, you know, modernizing their solutions as the next generation takes over, real-time status, visibility, uh, standardized workflows, audit trails that are updating real time, you know, portfolio-wide reporting, proactive communication, these are all things, um, particularly when you're when you're when you're talking about state deadlines that I think are becoming more and more table stakes, uh, that folks are you know wanting that real-time feed of are they in good standing or not? Um, and it's it's becoming less of a transactional business and more of an operating system for doing work efficiently in the compliance realm where we spend our time. Um, so that's certainly something that I've observed and I suspect it will continue.

Mark Wickersham, Host 8:38

Yeah, it is great to see the modernization of the of the family offices. I I think there are a number of trends that are are supporting that. Um obviously the next generation isn't looking to do business the the way that maybe their parents had done or previous generation in terms of you know manual paperwork, manual processes, lack of transparency. They expect things to they they have things in their personal lives which are automated and graceful and and intuitive in terms of technology that they use. And then when they come to their family office, they they're starting to expect the same. I think also you're starting to see a lot of uh vendors that are solving specific problems like yourself that that help with that kind of vertical integration and allow that these family offices to get deep solutions um where they previously might not have. Tell me how you you fit into a family office's tech stack and and what should family offices be thinking about as as they're kind of uh designing their tech stack.

Frank Tumminello, FileForms 9:42

Yeah, file form sits in the tech stack as the system of record and the execution layer for state entity compliance. Um so we really centralize the entity data, uh, the documents, we track jurisdiction specific requirements and deadlines, the specific dates, the fees that it cost to file, um, and then we manage the work across all the different entities to ensure that they stay in good standing. That is essentially filing an annual report each year, being the local registered agent address in each of the jurisdictions that a company uh does business in, helping form new entities for, say, acquisitions or purchasing real estate, for example, and then also forum qualifying businesses that perhaps as they establish nexus across new jurisdictions, ensuring that they are registered appropriately, have that local registered agent, and are in compliance with the Secretary of State. On top of that, uh we help family offices run compliance like an operating system by tracking roles, permissions, responsibilities across the entire portfolio. Uh, so the the right internal team or the right internal team member or even external advisor has the right access to the right information and has the right responsibility assigned to them, helping to effectively streamline filings, streamline payments, uh, which is another thing that is certainly a pain point, is just the whole payment function, invoicing, billing, collecting state fees, calculating state fees for that matter. That's really what our platform does, keeping everything clear, transparent, visible at all points of time throughout the year, uh, so that there's really no one-off surprises. Uh, and the result is a portfolio level view of what we own, what's due, who's responsible for what, what's been done, what's been paid for, without needing a bunch of spreadsheets or fragmented vendor portals or one-off invoices coming to your uh physical mailbox. Um, so that's really how we plug in uh to any pre-existing infrastructure or link uh as as kind of the foundational piece uh to that family.

Mark Wickersham, Host 12:07

Obviously, family offices have to deal with a lot of complexity, and we talked about how they have to deal with a lot of entities. Where where without a solution like yours, where where do family offices kind of break down? What are what are some like horror stories that you've run across without naming names?

Frank Tumminello, FileForms 12:25

Uh, you know, generally speaking, folks are coming to us um with uh a long list of of entities. Um, you know, they typically um don't have a single source of truth for that entity data. Um details such as the jurisdiction, the registered agent information, the officers, the address. Um they might live somewhere in the spreadsheet or in it in someone's inbox or uh disparate vendor portal, but typically there's not kind of that one central source of truth. We really help with that. We can help take any of the information you currently have, reference the Secretary of State's site, and really kind of create that nice clean audit of current state. Uh, we can wind down entities that are no longer needed, merge entities that that that should be uh aggregated. Um so that that's one way. A lot of times also deadline management is is more reactive than proactive. Um teams relying on individual reminders, calendar notes, things of that nature to manage a portfolio of at times multi-millions, if not billions, of assets. Um so when you're not taking a modern approach, um things do fall through the cracks, unfortunately. Um, and that can expose staff members, specifically when they're out of the office, perhaps on vacation, or you know, managing a migration between vendors, um, which really segues nicely into the next issue that we see quite prevalently is fragmented vendor relationships. Um, a lot of times people are um acquiring assets, different components of their portfolio in a very kind of uh ad hoc way. Before you know it, after a decade or after a generation, there's a bunch of fragmented vendors across all the different jurisdictions, different registered agents across the country, uh sending different notifications. And then there's also these exterior vendors that are trying to win the business as well. So, what does that create? It creates a lot of confusion for staff who might not necessarily uh be relying on a single source of truth to keep things in order. It could end up complicating things more. So that's really where we feel like there's a vendor consolidation opportunity uh to bring everything in one place. Um and then generally speaking, roles and permissaries not clearly refined when you ask a family office CFO or controller, hey, who does this? A lot of times they're pointing to their attorney, but then their attorney's pointing to the CPA, and then the CPA is pointing back uh to that individual. So um rather than play a game of telephone with extremely important compliance requirements, um, why not just have clearly defined roles and permissions uh for folks to get this work done efficiently? And then largely payment documentation can get quite messy. Um a lot of times folks are invoicing portfolio companies that end up not doing the work at the Secretary of State level or had already done it, and now there's redundancy. Um so once again, just having a streamlined uh process for payments, documentation, roles, responsibilities, filing deadlines is really gonna help the firm run more efficiently, remove the stress, keep things simple, stay at the forefront of compliance.

Mark Wickersham, Host 15:57

So um Corporate Transparency Act, the CTA is the is the CTA dead? And then also I I think as as a lot of family offices kind of rushed to comply with the CTA. Um what sort of positive aspects have have come out of that particular exercise? And what should family offices be thinking about going forward with the CTA?

Frank Tumminello, FileForms 16:21

Yeah, I wouldn't call the CTA dead. Uh for for the most part, it's it's dead for now. Um, you know next administration? Probably. Uh if I was a guessing man, um as folks know, um, you know, there there is a pause on the regulation since you know the current administration took office. But I will say that the CTA was an exercise that we saw several family offices get their entities in order, um, kind of get that uh single source of truth implemented within their portfolio, really kind of lean into entity hygiene. As odd as that may sound, it it's a real reality. So just standardizing the governance and kind of the change management for laws that can come in uh on short notice, as we did see uh with the Corporate Transparency Act. I think uh getting this work done to ensure that uh a system's in place and you have a proper uh piece of technology to support the portfolio is gonna make you more poised for inevitable legal change uh within the law. Um so whether the CTA comes back or not, um I won't I won't uh speculate there. However, I would say there's there's no harm in in having uh a clean back office uh with a strong operating system to manage entities and uh file forms can certainly help with that. And quite frankly, there's 50 states that also have their own compliance requirements. So uh I don't I don't see that same stroke of the pen risk uh as you would uh with the CTA across all 50 states. In fact, states like New York have implemented their own version of the CTA thus far just for foreign reporting companies. However, that could be subject to change once the federal CTA perhaps does come back around. So uh stay tuned for more on the CTA. Uh for now we're we're focused on state compliance at file forms.

Mark Wickersham, Host 18:32

Yeah, I mean it's not necessarily such a bad thing. And sometimes when regulation it comes, it forces you know family offices to modernize, put systems in place, take a look at how they're doing business, whether it makes sense, implement better best practices. And as you said, sometimes even when things kind of get held up at at maybe a national level, you definitely see some states moving forward. Some states are a lot more progressive with regulation, California and New York, um, and you still need to be prepared for that. Obviously, it wouldn't be a Wealth Tech podcast. We didn't talk about AI. How is AI impacting your business?

Frank Tumminello, FileForms 19:11

Yeah, AI has impact impacted our product in uh in a very practical way. Um it helps us uh be much more proactive and more helpful uh inside the filing workflow itself. Um, so clients could actually get uh from I need to file to it's done a little bit more quicker with less friction. Um we use AI internally quite a bit uh to better anticipate what what a user is trying to accomplish, um reviewing user journeys and things like that. Also, we're always trying to surface the right guidance and education at the right time to just allow our users to always feel well educated in in what they're uh uh you know looking to do for their entity. Um we feel like this helps kind of reduce back and forth, um, which unfortunately is kind of the industry standard. Folks you know, working with other vendors probably have to do a lot of back and forth via email and phone. Um, but you know, when you're managing a large portfolio, having those pro predictive analytics and proactive uh motions are are certainly going to help um provide more peace of mind and and better support. At the same time, we're very intentional about how we apply AI. Um, you know, we found that folks don't just want software, they they really are seeking peace of mind. So our philosophy is really AI plus white glove customer service. A lot of the the AI tools uh are certainly helpful resources for users to move quickly, uh confidentially. Uh, but but a lot of times, you know, there are folks that that do need uh that that personal touch from from our teammates, and uh a member of our team is is always available to help. Um so it's really kind of a balance of those hands-on experiences um that you know will not just sit in a silo, but also feedback into the AI uh initiatives that that we do internally. So there is uh this feedback loop that I think is becoming more and more powerful so that eventually every move we make is an AI first motion, uh, which hopefully, as odd as this might sound, delivers a superhuman outcome. Um because technology is accelerating super quickly and more and more people will expect it.

Mark Wickersham, Host 21:34

I I think that makes sense. I think you know there's still gonna be a need for a long time for it for the human in the loop. I think um in a lot of ways, AI can help enhance the the human interaction because it frees people up to be able to think a little bit higher level, be able to have some of the lower level tasks such as filling out forms or or even knowing intuitively and getting prompt about. What's what needs to be done when to do that? I I I think AI is from a product standpoint too also uh changing how people navigate systems. You don't necessarily sometimes need to know how to use the system. You can just in a in a large language model be able to just ask it questions and be able to interact with it that way in a very human manner. Um but I I think all that makes sense. Taking a look at at the industry, obviously you've seen it evolve and starting to modernize over the past two years. But if you're gonna take a look at, you know, the next three to five years, where where do you see the family office industry going?

Frank Tumminello, FileForms 22:41

Yeah, I certainly uh think there will be a lot of innovation over the next three years. I think the family office industry is um gonna look to modernize uh their operating businesses. Um they're they're certainly gonna look to you know standardize knowledge base, uh, standardize different processes, you know, such as administrative back office. Um, there's definitely gonna be, I think, a rising complexity uh in portfolios, which will likely lead to uh more need for um you know sustainable infrastructure to support that complexity. Um there will likely be more scrutiny from counterparties and and folks trying to compete with a lot of the technology. So there'll likely be a lot of you know exterior forces that are ensuring that data is is well kept, is is private, is secure, um, we're SOC2 compliant. We take data very seriously. Um but you know, with the with the wealth transfer that's unfolding, baby boomers selling their business, there certainly will be more family offices stood up in the modern era. Uh so with that, uh hopefully you'll see more infrastructure that is modern from the get-go, um, which which should streamline the ability for uh firms like ours to really serve um in the most streamlined way. So ideally you see less spreadsheet-oriented and email-oriented workflows, um, more kind of cloud-based technology, mobile optimized solutions so that things can be managed uh on the go. Um, you know, I think there'll be higher expectations for control at the family itself, um, and certainly more kind of predictive analytics, AI uh influenced uh technology within within workflows. I think at the end of the day, folks are trying to build uh scalable portfolios that can you know stand the test of time. And uh doing that as efficiently as possible uh should free up time and free up resources to further propel uh the the next generation. So those are a few trends that that we're certainly leaning into at our company. Um and uh yeah, we're we're thrilled uh for kind of the next generation of family offices coming. And it's just been so impressive how the industry's taken off, even just in the few years that we've been serving it.

Mark Wickersham, Host 25:19

Yeah, it certainly is the is the golden age for family offices. You're seeing a lot more family office creation due to um the wealth transfer. Uh you're certainly seeing that that generation be more technology positive. I think family offices are always gonna be wanting to do more with less. They are always gonna be running lean, but they're able to they're gonna be able to do more with AI, in particular AI-enabled uh platforms, which I think it's how the majority of family offices are gonna be exposed to AIs through the vendors that they're using and they're gonna be embedding it within their systems, whether it's through back office reconciliation and management of big data sets or even in a very front-end way through these natural language models. Um I think SOC 2, as you mentioned, is extremely important as as these family offices look to modernize their tech stack. They should really take a close look at at the legacy software that they have in place and make sure that the vendors that they are using are SOC 2 compliant, that that should be kind of a table stakes. Um I think APIs and systems integrations that have enabled firms to be able to create best of breed tech stacks, where in the past they've been a little bit more of a science experiment and that really allows firms like yourself to really focus on a particular area of expertise and and and provide excellence in that area where maybe a vendor that that's has a big portfolio can't necessarily focus on on really kind of uh deep vertical solutions like that. Um, I think family offices the the problem that they're gonna see is you know, the good news is you're gonna have more choice, the bad news is you gotta have more choice, and there's gonna be some buyer confusion out there about how you know what systems they should go to, how they build their tech stack, but that's really a high-geared grade problem compared to what it used to be, where they had to take maybe retail software that didn't have the permissioning and auto trails in place and really wasn't multi-entity or the ability to maybe take something that wasn't you know form fit for them and and then try to do develop a lot of workarounds. Um, so I I think it it's just the beginning and it's only gonna accelerate, which is great. Frank, I like to end the podcast on a more of a personal note with three questions that have nothing to do with wealth tech. You've had a chance to be in a number of movies as an extra. Can you tell me a little bit about that experience and and how that came about?

Frank Tumminello, FileForms 27:51

Sure thing. Uh well, I I can I can humbly say I've never started a movie, um, uh, but I have been very fortunate to be in a few feature films over the course of time. Uh the first one was I've when I was 14 years old, I was in a movie with Luke Wilson and Jimmy Buffett called Hoot by Carl Hyeson. Uh the really cool part about that experience, not only uh being on set with those two legends, but also uh that was my childhood uh favorite book growing up. Um it was amazing to participate in that project. And then most recently, uh I was in a a film, uh, had the honor of being uh in a friend of mine's film, Evan Kelman, uh a film called Baron's Cove, uh, which is actually uh now streaming on Paramount Plus. Um so if you have a chance, check that out. Um Evan and I had had the benefit of going to school together for a very long time at at Pinecrest here in Fort Lauderdale. And uh he's a phenomenal young artist who is actually currently fundraising for his next feature film. So uh if there's any families out there who are movies, movie buffs or or looking to be uh the next executive producer, that could be a good opportunity. Um but thus far that's the the movie career. Uh been spending a lot of time on file forms uh as well. So it's a telling you.

Mark Wickersham, Host 29:19

Sticking with your day job.

Frank Tumminello, FileForms 29:20

Yeah, certainly.

Mark Wickersham, Host 29:22

Um you're you're down in southern Florida. What what is uh something that that people might not know about uh the Fort Lauderdale area and and and what what would be some some hidden gems down there if somebody's down there visiting?

Frank Tumminello, FileForms 29:36

Oh man. Um well I I would have uh go ahead and uh suggest going to uh quarter deck, which is uh a local seafood spot down here in Fort Lauderdale. I actually used to work there when I was a kid uh as a food runner. Uh I was actually there last night uh watching the national championship game, which was fun. Um so uh there's a ton of great seafood spots. Southport raw bar is another great one on the water. And then uh a lot of folks don't know that uh Fort Lauderdale claims that it invented spring break. Uh so a lot of folks in my my parents' generation probably recall the elbow room uh down on A1A and Las Olas Boulevard. That's a must-see spot uh if folks are planning to come down south.

Mark Wickersham, Host 30:23

Well, I always wanted to go down there for spring training, so maybe I'll have to hit hit a couple of down there. And I always recommend the people if if yeah, can you have with kids or if you want to understand the value of hard work, food service? Yeah, whatever it is, hospitality, be a waiter, line cook, dishwasher. You want to learn the value of customer service, you want to learn the value of hard work.

Frank Tumminello, FileForms 30:52

That's where it starts. That's where it starts. Working for tips.

Mark Wickersham, Host 30:55

Um finally, uh, is there a book or podcast that you'd recommend to the listeners?

Frank Tumminello, FileForms 31:01

Well, outside of this podcast, I would say uh I did uh read over the holiday uh the book called Buy Back Your Time by Dan Martell. Um he uh he's uh a legend uh in kind of inspiring entrepreneurs uh that are building software companies specifically. I also read his book, uh Software as a Science as well. Um but if you're really looking to make uh 2026 even a better year than 2025 and do that in a way that uh keeps your head sane and uh keeps a smile on your face, I think it's a great read. And uh that's that's what I'd recommend.

Mark Wickersham, Host 31:40

Buy back your time. Okay.

Frank Tumminello, FileForms 31:41

Buy back your time. Yep, that's it. Go do it.

Mark Wickersham, Host 31:44

Well, Frank, this has been great. Thanks for so much for coming on the podcast.

Frank Tumminello, FileForms 31:48

My pleasure, Mark. Thanks for having me.

Mark Wickersham, Host 31:53

Thank you for listening to this episode of the Wealth Tech Podcast, brought to you by Seta AI. Seta is on a mission to modernize the family office. I really appreciate you listening, and don't forget to subscribe so you don't miss future episodes. Talk to you soon.