I'm Rob Sarnney and you're listening to what the heck fintech where you'll experience and learn that fintech is finite. Let's get started. Welcome everybody. You have an unbelievable guest speaker for you today. I am speaking to a very near and dear fintech friend of mine and just friend Ian Sheridan and he has so much and and he's going to take this to a whole another angle. He grew up in fintech and he's going to explain all that. He's he's he's a co-founder of Go Ventures. They're focused on AI and fintech and so much more. I mean you're going to you're going to get some really great unbelievable life-changing stories. Now, one little thing I'd like to add to this too is and and Ian, I don't think Ian knows this, but I met Ian back six years ago and when I joined WPI and he recommended me to and WPI actually recommended WPI and I happen to be at WPI time recommended you got to have WPI because he's done work with WPI before just that great simple you know act of kindness and how he introduced me to mass fintech hub. that changed the trajectory of my retirement and I was at Fidelity and then became a the professor job was a retirement job for me and he just ch that one act of unbelievable kindness changed my whole trajectory of my retirement and what I'm doing and is really the really the foundation of why I even doing this podcast because all the unbelievable things Ian did for me throughout the years and the collaboration we've done. So that's why he's such a near and dear friend of mine and I'm so excited to have him here. So So Ian um I can't do it justice. You you you'll do unbelievable job. How did you get I mean you know we're similar agents. How did you get to this fintech space and how did you grow up here? I'd love to hear that story. Sure. Sure. First of all, thank you for that kind introduction and and uh overstated by the way. So I I you know you you uh have an unbelievable career and what you did at WPI for those students was inspiring to all of us in the ecosystem. So thank you for for that leadership there which has transpired into mass fintech hub which has cascaded throughout the state and throughout the entire VC ecosystem. Um and we'll come back to that um the Boston ecosystem. But you you asked me where I started. So I, you know, you said I'm as old as you are, which is, uh, yeah, I just reflected on that this morning in advance of this, and I track my career. My first job was at the age of 12. Let's not go that far. But my first real job in college was uh, a summer intern on the New York Stock Exchange, and I co-auled all of lower Manhattan uh, during my freshman summer to see if I could get a job on Wall Street. um didn't have a resume, didn't have a proper business attire, but knocked on a lot of doors. In those days, you could coal call into New York. You could read the names of managers on the directories in the in the lobby, um and you could start conversations. And I was fortunate enough to meet a gentleman by the name of George Sice, um who is the specialist for RJR Nabiscoco, um and was on the the the specialist on the New York Stock Exchange. After a lot of interaction with him, that is probably a story for another time. He brought me down to the New York Stock Exchange. He showed me, gave me a tour before the market opened and then said, "The problem, Mr. Sheridan or Ian, is you're too tall to work for me. The specialist, the juniors behind the screens were literally these were before flat screen TVs. So the TVs that the monitors that were being used were remember those big three foot you know extensions behind them. So to work in the the pit of the New York Stock Exchange to help the specialist run the book. It was like it would be like working in a submarine. Um so he looked at me and he said you know you got a lot of boss coming down here to do all this and you've seen the tour now go home. I said no sir I'm here. I need to work here. and he actually introduced me to a number of floor specials. Talk about an act of kindness, right, which is is always paying it forward. He introduced me to uh what was at the time called the $2 broker, which was somebody who leased a seat on the New York Stock Exchange. So, I became a gopher and then I became a wire clerk. I had six 60 institutional wires and I would take orders back in the day of buys and sells and then beat the broker on the floor to execute the trade. That's where the New York Stock Exchange was at that time. And I in advance of this, I just wanted to to look back what was the down. I remember it being under 2,000, which it was. And it's increased. It's over 41,000 today. That's a 2,000 plus percentage increase over time, which is just incredible. Wow. But but the relevance of the story for today's conversation was at that time I was still in college. I was seeing more income than I could imagine in that type of of atmosphere. I forget what I was paid, but for the kid at 17, it was it it turned my head to say the least. Um, and so I thought, well, I'm just I'm going to quit college and I'm just going to be this wire clerk because I got the cadence. It's it was like being a sophisticated waiter in a sense that you're taking information. You're retaining that information. You're you're absorbing the actions around you and the behaviors to kind of bring back that intelligence uh to the institutional uh broker which we'd say is upstairs on the phone. Um and the $2 broker I worked for, God bless him, Henry Lee, uh had had a seat on the exchange for multiple generations of his family. and he looked at me and he said,"Ian, if you make that decision, you will not work for me. You will be on your own, but if you if you stay through college, I'll help you when you graduate." And which ultimately got me to Goldman Sachs. So, relationships really matter. The the other piece that was cool, a little trivia, it was the first time it was either 87 or 88, maybe it was 87 before the market crashed then the first computerized trade went through and I'll never forget because we would watch the ticker tape around the New York Stock Exchange and it does does create a momentum and there's a there's a cadence on the floor of the New York Stocks as you pick up from the humanity getting excited or reacting to the different things that would occur. occur across the day. And I'll never forget Henry point grabbed me and said, "Look," and he pointed to that trade and it might have been 10,000 shares. Um, and he said, "That's why you need to graduate. Everybody here is a dinosaur. They just don't know it yet." Now, the New York Stock Exchange still exists and it's modernized and I don't mean to take away from its value. It's an important um part of our financial system. But then it was manual. It was beeper. It was phones. It was paper orders. So I'd start the day, the floor would be a gymnasium floor, you know, spotless wooden floor, and by the midday, end of day, I was ankle deep in trade tickets that we had written and, you know, either timestamped and collected or threw on the floor because it didn't get executed. So that's where I started, which puts me 40 years in the business or 39 years. One thing I wanted to jump in there with because I got to be late in my life. I want to talk about like three or four years ago on the New York Stock Exchange. We had a we brought you know we had we brought a bus of uh WPI students for the investment club which you guest spoke at before WPI investment club and I was amazed. I never saw at the old except in movies right the exact thing you're you're showing and talking about but I remember walking on the floor I'm like oh my this this is fintech in the like to it to the unbelievable level. I was looking around. It's an amazement and just the buzz and all the that press there and you know and and and you're right there right in front. We're right in front looking up at you and the bell and it was just like for opening bell too. It was just crazy. So and I I just think of that story. I'm like I wonder I bet you that impression that those students got maybe they'll be inspired like you did but you obviously had deeper inspiration because of the great connection you just story you just told. But that just got me thinking of a story that I haven't thought about in a little while. Wow. Well, you think about it. Our our careers, both our careers tracked in a at a time when American workers were just becoming saving savers and investors, right? It was the defined benefit was the primary way in which American workers retired. Um, Wall Street was certainly growing and the Dow at at 1,800 I think was the number in ' 86. um mutual funds were certainly available but for high netw worth individuals and then that turned right Orisa came out all of a sudden the the the Wall Street asset management insurance infrastructure geared up for retirement plans 401k primarily um there were other forms as well in those early days but that's when American workers started driving assets at a massive level into the markets and mutual funds I remember my biggest tech challenge in the in the8s 80s and 90s was could we get our new mutual fund that we're launched launching for our retirement plan business in the Wall Street Journal so that people would know where it is and and how it's tracking right there were there I forget what the number was it'd be interesting to ask AI today what was the cadence of weekly mutual fund formations in the 80s and 90s but it it exploded right and so our systems our technology and thank thank I always remember Henry Lee pointing to that first computerized trade automated trade and telling me I needed to, you know, always be advancing and learning and staying curious. But those systems we grew up with have changed. They were transaction battleship type systems, not designed for the highfidelity of data and interaction and analytics that we use today. Um, and they certainly have evolved and they're going to continue to evolve. Um, which is which always brought me into the excitement of Vestigo of getting part of becoming part of that team. Wow, that's that's an awesome story. I love that story. I now to keep that story going. I'd love to hear how did you know you you you co-founded with Mark Cassidy, Vestigical Ventures. How how did that come to be? Were you guys both having a couple beers like we should do this or like what what was it like like how did this all happen? Cuz you guys are doing unbelievable things. Yeah. I mean maybe I I could describe it as the act of kindness you described with you and I interacting. It was really Mark's vision. Um he was running LPL at the time and I think he was thinking about tomorrow today which he is so very good at and seeing around the the next corner. um and and really um had the vision to start Bestigo and he had this great relationship with Dave Blondon, our other founder and Dave we always call the cool one because MIT neural networks, predictive analytics, he was really working with the first the professors teaching AI at MIT. Um and he came out of MIT with a cohort of really brilliant people who understood data was the next oil um the next major asset to build on and it was the kind of the middle of the dot era. Um but it was Dave and so Dave and Mark had this amazing relationship over 30 years. I've known Mark since I was at ADP when I was a corporate executive. uh I I ran uh marketing and some business development activities and we were trying to convince Wall Street at that time that ADP was more than payroll. So we're building the retirement business. We were acquiring defined benefit businesses, executive comp businesses and that led me to Boston um from New Jersey to look at the scutter retirement businesses u at that time which Mark came out of scutter and then was running Deutsche Asset Management. So that's how we met our our teams interacted. I just was really impressed with the way Mark led teens. Um, and just through that interaction really over 30 years ago u as I think about the the birth of my first child right when we met we stayed connected primarily through the Tibrron CEO summit. So I'd see Mark once a year. I'd see and I'd watch LPL as an analyst was really important as we talked about the evolution of technology, the growth of our industry. At that time, LPL might have been, and don't quote me on it, but it might have been a thousand brokers or 500 advisors. Um, and we tracked and Schwab had just opened. I think it had 50 employees at that time. So we were tracking the birth of the RAIA and the growth of overall the growth of American distribution systems in asset management to understand you know one where we could bring our products and services for distribution but two to understand the changing dynamics that were absolutely occurring during that time and so I remember when LPL started to train raas and I'd watch that number as it would be publicly reported from time to time say okay this is really interesting Charles Schwab is forming. So that formation of the advisory network that we see today in RAAS and other wealth management firms we've seen that whole change right you were there at Fidelity was really really interesting. So anyway to come and I deviated but to come back to Vestigo Ventures it was Mark who had the vision and he wanted to give back to the Boston ecosystem. So that was a core ethos to Vestigo. Dave had this amazing set of companies. I call them the cool one because he created over 26 companies in data and predictive analytics that were just phenomenal. And he and he had the vision to build his first really lab KO labs pretty much across the street from MIT. Um and at one level it ran an ad tech cap business where it was able to support itself and run data and grow its its assets uh from a data perspective. and then he would incubate companies under link ventures which we're part of today. Um we'll come back to that but so so Dave really had that vision of data being the new oil and to build companies around it. Um, today KO has evolved to link studios which still has the the ethos of building startups around AI but it's all MIT and HBS founders coming in with these new ideas but but Vestigo was formed with with three of us with the idea that we did we would be part of the Boston ecosystem part of the national ecosystem in early stage investing in fintech and finding great at that time it was machine learning AI type companies And so we've come a long way. Um first fund is an 8-year vintage from 2017. Second fund uh is wellformed and fully um allocated to portfolio companies. And the third fund really has moved from Bestigo to a pure AI focus with link ventures and the MIT ecosystem. So we've we've come a long way. Um that gives you the the background story. Yeah, that's the Wow. cuz yeah cuz I cuz um you know we got to know each other in 2019 and um that is the growth I've seen from 2019 to now is like unbelievable and your portfolio and how you do things it's like amazing um yeah so with that amazing um part let's let's piggyback on that what's a day in the life to go ventures I know you meet so many geniuses and and unbelievable startup s and you coach them and help them and and and what's that like? That must just be fun every day. And I know how you um you you do something you you have very unique approach to to to to find and to meet those uh startups too which I don't know if you can share that might be uh you know secret squirrel stuff. VC every VC has its its methodology and there's similar playbooks that I found across the board. But I think what made us distinctive early on was the the team itself. So you start and just as we as investors start with team for vestiggo we spent a lot of time early on you know thinking about what is our ethos um what is our culture uh going to be and our value proposition and so we spent a lot of time establishing that and the idea was to build a multigenerational team that reflected the markets that we serve the people that we invest in. And so we started there with data as a center point of being the the real truth. Um the other piece was in you know bringing our experience um in a in a realistic way and of course we learn with data um you get humbled about your experience very quickly uh as you think what you think you experienced or what you might happen again it's necessarily not going to happen the exact same way and data shows you that path. So um yeah, we we really started out with team and building building that team and we're proud of the folks who have been part of Vestigo and now are in the link uh third fund um working uh the latest AI but you know the the the the journey has been um for me 10 years because there was about two years of early spade work of trying to figure out what are we going to be how are we going to leverage the data assets that Kog Labs have and that was our connections is WPI by the way, right? So, um Dave had built an amazing set of algorithmic tools that um fell into what I'd call the predictive analytics side of of working with data. And we saw that capability of uh that Kogo had to look in across the North American um data landscape across the internet and really see certain signals as it related to uh URL showing the potential to go viral. And so that was really interesting to us and it would create a massive haystack of companies that were showing signal from those companies that were publicly traded all the way down to the early early startup that just hung up a URL address or a.com address now you know lots of different extensions. Um so that hastack was really interesting. Um and so what we did um with our team and the help of of the university system that we participated in through interns, we built a set of algorithms, you know, eight years ago. We called it XPLR, but it was really five mathematical models that would look at that haststack of companies KOGO would find showing potential signal and it would start to be trained by us. We'd look at that data and line by line and we'd say it would source a URL and each team member would get a pile on a spreadsheet and we would score it on a scale of 1 to five according to our thesis and our lens of experience. So a couple things happened. One, we we trained the data. Um the training got interesting because you began to see the bias happening. So it was just three founders of similar diverse backgrounds but similar. um you'd see certain output, but as you brought in younger associates with different lenses, you started to feel that bias take place as well. And so the mashup there at the human level working with the data created really interesting output. Now, I can't say it was a magic it wasn't a magic tool by any means. It wasn't a trading algorithm. It was it was part of what every VC does, which is to um hunt to search uh for great founders. And so any tools that you can use to help with that um you know is advantageous. And so we still had to do what every VC does. You had to get out into the ecosystem. That's where you and I met, right? And you had to you had to connect with people at the at the local level, at the creation level, at the ideation level and know where those people are and how they're interacting. And so Vestigo played a I think an important early early role in the Boston Fintech week um you know build of the ecosystem as fintech hub now sandbox etc. because we got out there, right? Yeah. So, how about that day in the life too? Like like what what in the morning? So, so, so just to come back to the data just really fast. So, that evolved from machine learning applications to now using LLM. So, instead of a spreadsheet of 200 names that I would get, I get an email that would say, Ian, here's five companies that that are showing the propensity of signal within, you know, the sectors you're interested in. So we we lived the L the LM L l the machine learning AI and LLM journey and I use you know most most popular models I now chat GPT5 and Claude on a regular basis in the work that I do. Please come back to part two with Ian Sheridan as Ian goes deep into the day in the life of a venture capital founder and also how teamwork, collaboration and leadership with a great culture is what really makes the magic happen. Thank you for listening to What the Heck Fintech. Make sure you tune in to our next episode as we continue to interview fintech leaders and share real world stories from across the fintech ecosystem so you can fully understand that fintech is finite.