0:00:00 - (Linda Jellison): As a member led group also needs support.

0:00:04 - (Peter Offringa): And Linda and I thought, well, really what we need is staff and help to make this a more serious organization.

0:00:12 - (Linda Jellison): We had to find someone who had the time. They need people who know what they're doing in terms of due diligence and investing and even legal.

0:00:21 - (Andrew Kazlow): Welcome to the Diligent observer, where we help angel investors see what most miss. I'm your host, Andrew, and every week we explore what works, what doesn't, what and why through conversations with experienced startup investors and operators. My guests today are Linda Jellison and Peter Ofringa, longtime leaders of Bridge Angel Investors out of Sarasota, Florida. Linda scaled an intelligence and cybersecurity engineering firm from startup all the way to acquisition by a Fortune 500 defense contractor.

0:00:49 - (Andrew Kazlow): And Peter is a technology executive turned

0:00:52 - (D): equity analyst and angel investor who previously

0:00:54 - (Andrew Kazlow): held engineering leadership roles at companies like Zooski, CBS Interactive, and CNET Networks. Now in this episode, we cover the process of professionalizing a volunteer run investment group, building out a stronger local founder pipeline and the gap between ecosystem building and actual robust local deal flow. I hope you enjoy learning from Linda

0:01:17 - (D): and Peter as much as I did. Linda, Peter, thank you for being with me today.

0:01:29 - (Linda Jellison): Thank you for having us.

0:01:31 - (Peter Offringa): Yeah, thanks for having us.

0:01:32 - (D): Well, I'm very excited to hear more about the story of your community. But before we get into that, Linda, I would love to hear, what are you excited about?

0:01:41 - (Linda Jellison): Personally, right now, I believe that our group is at a point where we've come a long way, but I think we're getting ready for almost a next phase. In fact, I believe we're meeting next week. The board is meeting next week to talk about what that next phase needs to be for our members and put some strategic initiatives in place so that we can continue to grow like we have.

0:02:03 - (D): Well, we will come back to that. Very excited to hear more about what does the next phase look like, because I think the ones you have been through as a community are already pretty interesting. Peter, what about you? What are you excited about right now?

0:02:14 - (Peter Offringa): Well, just adding to what Linda said, I'm excited about the growth of the group, but also the growth in Sarasota. Our community has really experienced an upsurge since COVID and Florida in general has benefited from that. But we've just seen this huge influx of talent and individuals and capital moving into this market and we're really trying to capitalize on that. And we have a lot of community members and investors and entrepreneurs who are really leading into the ecosystem. So, you know, it's. It's it's. It's almost an experience of, of really trying to build an ecosystem, you know, within a mid market and, and we feel like, you know, the ingredients are finally here and, and now the flywheel is starting to spin.

0:03:01 - (D): Well, I'm excited to learn a whole lot more about that flywheel. What's exciting to me about this conversation specifically is that Sarasota is, I'm learning, much more than a wonderful tourist destination. There's a really flourishing investment ecosystem here. And Bridge has been a key part of that, as I understand it, over the last decade plus. And so I wonder if, as a starting point, Linda, you could walk through maybe the origin. How did you first find out about and get involved in Bridge? And maybe as you're addressing that, you know, walk through how the ecosystem has evolved over the years. I mean, I know a lot has changed in Sarasota specifically. Many of our listeners, myself included, aren't super familiar with this part of the country. So with that, I will open it to you.

0:03:50 - (Linda Jellison): So when I moved to Sarasota, it was a sleepy little tourist town and I came with an engineering background and I was lucky enough to land a job down here. And going forward, I was able to continue to do that technical job, but very little other tech in Sarasota. Sarasota was a service community. It was focused on medical lawyers, service people who literally service the tourists. So as the years went by, I was really happy to be able to work here, but I thought it would be really important for not only me to work here, but more people, more of a technical focus.

0:04:29 - (Linda Jellison): So when I, after I sold my company, I joined Bridge Angels and I was introduced to Bridge by a friend of mine who thought that it would be interesting for me as a retired engineer to actually continue to link up with new people coming into the community. And that's what Bridge has been for me.

0:04:50 - (D): So this was 2014, 15 timeframe. When did this happen?

0:04:54 - (Linda Jellison): No, this was like 2017.

0:04:56 - (D): Okay, okay.

0:04:57 - (Linda Jellison): 2017. Yeah, 2017. 2018. Very small group, not a lot of momentum at that point. Good leaders, but just not a lot of momentum. And then as we went forward, we headed into Covid 2020. We made it through, but it was really after Covid, I think we found our rhythm and a group of people that really wanted to push. We wanted to establish a more organized group, hire staff, and begin a much more formal due diligence process so that we could attract more members and also make more of a difference in our.

0:05:37 - (D): So during that period, what changed in the local Community. I mean, it sounds like you saw some influx of more tech activity. You know, this evolution beyond just a tourist town. Where did you see that or how did you see that happening over those years? Maybe pre Covid.

0:05:52 - (Linda Jellison): So while pre Covid, I think, was less of an impact, I think Covid brought a lot of people here, getting out of the big cities, looking at Sarasota as a place they can work and work remotely. I also think remote work just. Just in general helped drive some of that. People could come and live in Sarasota, but yet they could still do the work that they had always done before. So I think that was the start.

0:06:16 - (Linda Jellison): But then I also think that the more technical people you get, the more you bring. And so businesses started looking at starting up, down areas down here. So I think that was really a slow but constant change. And, and then coming out of COVID I think people realized what a great place it was to live. And so that's just exploded. Couple that with having a group of people like not only Bridge Angels, but of a lot of other technical people and other tech groups starting up. I think it's just turned a huge focus on entrepreneurship and smaller businesses growing and larger businesses growing in Sarasota.

0:07:02 - (D): So Peter, as I understand it, you joined maybe shortly before COVID or right around Covid. I'd love to hear how did you find out about Bridge Angels and what drove you to join and then maybe your thoughts on that season?

0:07:14 - (Peter Offringa): Yeah, so I moved here in 2015 from San Francisco. I'd spent my career out there as leading software development teams for consumer Internet companies. But after moving here, I kind of transitioned into venture capital. And I got introduced to bridge Angels in 2021 through a mutual friend. And I'd done some angel investing in the past in San Francisco, but found that angel investing was a good way to get involved in the community, to work with founders and support startups.

0:07:53 - (Peter Offringa): And for me, that participation really allowed me to, you know, get more involved in ecosystem here. And I think that, you know, what, what we saw after Covid is, is what Linda mentioned, this realization that remote work, you know, was acceptable as a way to, you know, be productive. So we saw this large influx of individuals from other cities, you know, often who are entrepreneurs themselves, you know, that maybe built a business and then sold it for seven, eight, nine figures.

0:08:29 - (Peter Offringa): You know, had heard about Sarasota, has some connection here and decided to move here and, you know, enjoying the benefits of weather and low taxes and safety and family friendliness and those types of things, always with the you know, potentially with the intention that they wanted to take a little time off and spend time with the family, but after a year or so, got bored and. And, you know, we're looking for thing other things to do. And so they, you know, found the angel group as well.

0:08:56 - (Peter Offringa): And we've had a lot of members join us over the last two or three years. As a consequence of that, in fact, our group is probably. I think we doubled in size in the last 18 months. We're at 50 members now, and that's really allowing us to really increase our impact. And I think that a market like Sarasota has the potential to support an even larger angel group.

0:09:21 - (D): As you're talking, it feels like the two of you sort of represent that typical profile. I mean, you both successful entrepreneurs working in tech in some kind, moved here, exited what you were doing at the time, and are now looking to kind of give back and support the next generation. Would you say that that's pretty typical for the profile of the active members in your community today?

0:09:41 - (Peter Offringa): Yeah, there's. I think that, you know, similar to. To both of us, certainly in my experience, I made a deliberate choice to move to Sarasota, and a lot of the other individuals in the angel group and just in the tech community here also made that decision. They chose Sarasota. In fact, in a lot of cases, this was the first move they made, maybe without a job or without some requirement to be in Sarasota. It was a choice they made. So they oftentimes are looking for ways to contribute to their community, you know, outside of work.

0:10:18 - (Peter Offringa): And so I think that, you know, that was my experience, and I think is really part of what makes Sarasota special. You see a lot of activity both in the nonprofits and in, you know, groups like Bridge Angels, where individuals are looking to really get involved in the community.

0:10:35 - (D): So why Sarasota specifically? I mean, I can understand the general pitch of Florida and the weather's pretty good and, you know, like, enjoy the beach. But help me understand, like, what is it about Sarasota that maybe for the two of you specifically, was so appealing? I mean, Peter, you left San Francisco. I mean, the coast to come here. Why?

0:10:55 - (Linda Jellison): Well, for me, I. I, like Peter, came specifically to Sarasota. I spent a year trying to find where I wanted to live outside of being. I was. I came from Maryland. A lot of traffic. You know, you spend your weeks working and then your weekends fighting traffic to go and do something, and then you come to Sarasota. It's pretty laid back. It's grown. It's like formed beautifully over the years where they have, you know, great housing, great restaurants, now we have culture.

0:11:33 - (Linda Jellison): But it's just all in a smaller, like a smaller version. So I fell in love with it. And I think that's what happens is people, they come down, it seems to be that someone always has some kind of tie, an aunt, a grandmother. My parents used to come down here. And then when they think about where they want to live other than where they are, or when they exit a company, they think about moving to Sarasota.

0:11:58 - (Linda Jellison): And so they come down and take a look at it and they've seen how much it's grown over the years and they love it. And then I think we all kind of dig our heels in and say, we're not leaving. I mean, even for me, during COVID it was like, we're not leaving. It even made it better to stay here. So I think there's a lot of that. And I also think that there's some camaraderie to that. When we meet new people, they come down for the same reasons. And then we all kind of band together.

0:12:24 - (Linda Jellison): And the idea is in. I know that there is some concern that when kids grow up here, they go away to school and then they never come back here because there aren't enough jobs, there aren't opportunities for them here. So there's a little bit of that too, just underneath preparing this city to allow the next generation to come back and live here. So it's not just what a lot of people think of as. It's a retirement community.

0:12:49 - (Linda Jellison): Does that make sense?

0:12:50 - (D): It does, it does. Peter, I'd love to hear your thoughts. Anything you would add to that?

0:12:55 - (Peter Offringa): Oh, well, I mean, you know, admittedly the weather's pretty good, the attraction to Florida, and I credit my wife for doing all the research, you know, where she looked at all the different cities in Florida and she kind of ruled out East Coast. It's a little too, I don't know, built up. And then looked at west coast, which is more relaxed. But Tampa's just too big of a city, especially coming from San Francisco. And Naples is a little sleepy. But Sarasota just kept popping up as like this nice mid sized city.

0:13:24 - (Peter Offringa): You know, the arts and the culture, I think are unique. As Linda highlighted, I mean, we are a city of a couple hundred thousand people. We have our own opera, we have our own symphony. You know, we have several museums, we have a botanical garden. I mean, there is serious support for the arts here, you know, and I Think that attracts a lot of creative minded people as well. I also like the fact that it's a mid sized city. You know, I often joke that in San Francisco I would go to an event and meet someone and never see them again.

0:13:56 - (Peter Offringa): Whereas in Sarasota I go to an event, I have some anonymity, but I often run into people who I know. And I feel like you almost know anyone in Sarasota through one or two degrees of separation, which is nice. It's not too small, but it's not so big. It's overwhelming. It's a community.

0:14:18 - (D): I love it. It's interesting running this show. We've had a number of conversations with folks running investor communities in tier 2, tier 3 places. And this theme of. And the local community has these really smart people that have capital to deploy and want to give back to support the next generation of entrepreneurs. And so they just naturally, over time kind of coalesce into a community focused on doing just that. And so it's fun to hear about your community.

0:14:46 - (D): Specifically. I would love to hear more about this Covid era transition. It sounds like this was sort of a breaking point, a reorientation point. So we'll say for the organization, I'd love to hear more before we get to what actually changed. Like what were the problems that you all were facing as an organization around Covid that got forced into the limelight and kind of prompted you to make some hard decisions.

0:15:12 - (Peter Offringa): I think one of the challenges I observed when I joined was we were a member led and still are a member led organization. However, we depended very heavily on volunteers in order to run it. And as you can appreciate, running an angel group actually requires a lot of work. There's a lot of logistics to it. There's communication with know companies that want to pitch. There's, you know, as the, you know, the deals get formed, you know, the work around organizing those, collecting funds, you know, recruiting new members, et cetera, et cetera. And all of that was being handled by the members themselves.

0:15:53 - (Peter Offringa): And so we were very challenged in just being able to scale, you know, based on the limitation of, you know, members time. So that was certainly a constraint.

0:16:05 - (Linda Jellison): Definitely we did have a part time executive director. She was great. But again, running an organization and growing an organization, it takes a lot of time. And I think we all realize that. I think that was the biggest revelation that we had. If we really wanted to do this, we had to find someone who had the time and also pay them. We couldn't expect them to just come in and do this for free. And so I think that's where we began to come up with a better idea of what it would take. And in fact, our executive director helped us with that, help lay out a plan if we went out and hired someone.

0:16:46 - (Linda Jellison): But in order to hire them, we had to figure out a way to pay them. And in order to pay them, we have to have more members. So it's kind of, it's a little bit of the chicken before the egg and. But I think with the group we had, we're kind of like a dog with a bone. And we were not willing to give up what we had. We just pushed forward. And coming out of COVID we had these other great initiatives going on. Lots of people flocking here, lots of capital coming in, very interesting people.

0:17:13 - (Linda Jellison): And I think it was just kind of a launching ground for the new version. And so I think that played a lot. The timing played a lot into it as well.

0:17:23 - (D): So you, I believe, Peter, you're sitting as a current chairman of the board. Linda, your prior chairman of the. Were you on. Involved at that point when this decision was being made?

0:17:34 - (Peter Offringa): Yes. You were in fact. Yeah, we kind of. Because of COVID as you can imagine, you know, the membership also dropped off a bit because as a, as a member led group, there, there certainly is value in, in meeting in person. And that was a challenge. So, you know, the group was down to just a handful of members. And I think Linda and I looked at each other and said, this thing could either die or we're going to double down on it. And crazy as it was, we decided to double down on the growth. And another interesting learning was the group had always charged dues in order to kind of run the group. And I think when I joined it was maybe 2,000 or 2,500 a year just to kind of COVID overhead and incidentals and such. And as Linda mentioned, we had staff, but they weren't paid.

0:18:25 - (Peter Offringa): And so at first our inclination was, well, maybe if we eliminate Deuce, then we'll get more members. And Linda and I thought, well, really what we need is staff and help to make this a more serious organization. So we actually did the opposite. We raised the Deuce. So, so now the dues are $5,000 a year. And what that allows us to do is actually hire or hire staff. We not only have an executive director who works for us part time, I guess it's about half time at this point, but we have three other staff members who help with scheduling, due diligence, administrative functions, et cetera.

0:19:07 - (Peter Offringa): And that really takes a lot of pressure off of the members. For the, you know, what you would expect is just the basic logistics so that members can really focus on due diligence and investment decisions. And, you know, and of course, they introduce the executive director to. To other prospective members, but, you know, they aren't having to spend their time, like, organizing meetings and bringing food and picking up wine and things like that. So all the

0:19:34 - (D): member meetings, that.

0:19:36 - (Peter Offringa): That decision to help him, you know, the growth, even though it was a little bit counterintuitive.

0:19:40 - (D): So take me back to that boardroom conversation. Like, what. What was hard about that? What was the. Obviously, it seems to be working out okay, and I want to hear more about the journey since then. But, like, as you think back to that room, what was the main counter argument to doing this?

0:19:57 - (Linda Jellison): Well, I think other members were afraid if we raised the dues that we would lose people, and we didn't want to lose anybody. I mean, that wasn't our goal in the group. I think that. But I also think that we were. I don't know. I don't think we were that split, but there were a few people that were kind of worried. So we. We actually agreed to raise them for a while and see how it went. But once we raised them, it became really clear that the expectations of the people that are investing and coming into the group is it. They don't. They're not really that worried about paying less dues.

0:20:30 - (Linda Jellison): They like what we're doing, what we're giving back as an organization for them. So it. After a while, the question became not, you know, do we. Do we lower them? But we knew that we were just.

0:20:45 - (Peter Offringa): We.

0:20:45 - (Linda Jellison): We had them at the right level. And. And now, you know, now going forward, we have to decide if we. If we have to raise them or whether that makes sense or doesn't make sense.

0:20:55 - (D): So I think it's an important topic, and I appreciate you sharing the perspective because investor communities fund themselves in an array of different ways. We have seen dues from zero up to thousands of dollars. And I think the decision about how do we finance our operations is a really important one. It sounds like, if I'm hearing you right, Linda, that when you made that decision, membership didn't really drop much at all. Most folks participate, maybe a few here and there that might have turned normally anyways.

0:21:27 - (D): But was the result what you expected?

0:21:29 - (Linda Jellison): Probably better than we expected. I think it was really better. I really didn't get much pushback at all. And the new people. So our executive director, she's Very good at talking to people and listening to what they actually say when she's interviewing them. We also have a great networking. I think our members are our greatest asset as well because they bring friends and acquaintances and a lot of them are really, really integrated into the community and so they run into other people and they bring them in.

0:22:04 - (Linda Jellison): And then our executive director, Kim Meely, she's just the best at taking the temperature of the person that wants to come into the group and understanding if there are concerns or not. But she kept reporting back to us that no one appeared to be concerned about the deuce. You know, they had other questions, had other concerns, they had other suggestions, which we love because we are a member led group and so the intent is for people to give us feedback and we listen and we modify what we do.

0:22:36 - (Linda Jellison): But I don't think the do's ever were really a challenge.

0:22:40 - (Peter Offringa): Yeah, it was interesting. I mean, to be fair, we had tailwinds coming out of COVID There was certainly an influx of people, but I do feel like, yeah, the dues, certainly not at that level, were a hindrance in some ways. I think some of our members, maybe high net worth ones, almost looked at the dues as a barrier or a bar that maintain quality and also maintain a level of seriousness. Because I think that having a higher dues threshold also ensures that the people who are joining actually are serious angel investors and want to participate and, you know, maybe aren't individuals who are looking just to participate in the group to network.

0:23:27 - (Peter Offringa): And if the dues threshold were low, you know, you might attract maybe individuals in service industries who are just looking for clients, for example.

0:23:38 - (Andrew Kazlow): A quick note before we continue the conversation alongside the Diligent observer podcast and newsletter, I also run an outsourced operations service specifically built to serve angel networks. My team handles things like initial screening, social media, newsletter prep, platform management, and a whole lot more. The kinds of things that either aren't getting done or shouldn't be done by busy community leaders.

0:24:00 - (Andrew Kazlow): If that sounds interesting to you, send me a note.

0:24:02 - (D): Now back to it. So it's 2020, 2021 ish. You all have just made this decision. You're looking excitedly towards the future with paid staff that can do a lot of the things that members aren't rushing to raise their hands to do. Walk me through maybe the journey over that couple of years. What changed, what felt different and why? I mean, a lot of it sounds like it's attributable to Kim being amazing. So we'll include a link to Kim's LinkedIn on this recording. But besides Kim being awesome, like what else changed during that season that you guys felt having been around before and after that change?

0:24:43 - (Linda Jellison): So I think what we've said before is there was a, I think there was a bigger influx of people into the community that would have been members younger, younger. I think a lot of people exit. I think we're in an era where people are exiting sooner out of a business. They start a business and they exit. They don't start a business run until they're retired and then, and then, then they're retired and ready to go play golf every day. So I have a lot of really, really highly charged people who are looking to give back, looking to stay lifelong learners, looking to maybe even start again with, with a business.

0:25:27 - (Linda Jellison): So I think it, it was like a perfect ground for something like an angel and angel networks, not full time. It's, they're not, they're not committed to going and doing a job every day. It gives them an opportunity to meet lots of new people and like minded people. I think that's the other thing that makes Bridge so unique. I have a lot of people asking me, they're like, well, I didn't think you were working anymore.

0:25:52 - (Linda Jellison): I'm like, well, I do not consider participating in Bridge Angels or even mentoring or I don't consider that working. I consider that just part of my life. I don't know that I'll ever give up doing that. And I think finding people who don't ask you that question, it always makes it a little easier because they understand the challenge of the alternate investments, but they also understand what you get back from that, you know, meeting. I've met so many people, so many people through Bridge and you know, growing my business here in Sarasota. I also, my customers were up in Northern Virginia so I didn't really have a lot of time to meet people.

0:26:36 - (Linda Jellison): I just worked and then I come out of, of selling my company and now I've just, I'm surrounded by, by people and meeting new people every day.

0:26:46 - (Peter Offringa): Yeah, I would add, I think what we noticed coming out of that period of 21, 2021 and 2022, after we kind of raised the dues, is first just a high caliber of new members. I think, you know, certainly indicative of again the influx of talent into Florida. But you know, these are individuals who you meet and they're very down to earth and very conversational. But then you go look at their LinkedIn, you find out that they were C level at some Fortune 500 company, you know, very impressive background or, you know, started a company that sold for eight or nine figures and had a write up in Bloomberg or Forbes magazine and, you know, and had had some level of fame themselves. And, you know, so it was, it was really, I don't know, refreshing to have those type of people want to engage with us in the group.

0:27:47 - (Peter Offringa): And then I'd say the second thing is that Linda and I and a couple of other individuals along with our staff, Kim, we've mentioned coming out of that period, we're doing a lot of the heavy lifting ourselves, putting in a lot of the time and the energy to make the organization work. And then over the last year or two, we've seen another level or another round of people who have been with the organization long enough that they're familiar with it, see our mission and are inspired by it, and now they're leaning in.

0:28:21 - (Peter Offringa): So, you know, we have a whole additional circle of individuals who have joined the board, who have volunteered their time, who, you know, lead due diligence. We even had an individual who basically built an app for us. An app, A website, an app where we manage all of our information flow and, you know, due diligence and deals and I mean, and it's amazing, like Vibe coded the whole thing and he maintains it. So, you know, it's, it's, it's refreshing to have, you know, other people kind of raise their hand and put in the time to make sure that the group is successful because they think it's important.

0:28:59 - (D): Peter and Linda, as you're talking, I mean, this is what gets me so excited about doing conversations like this and helping communities like yours build and grow is because you get excited equal parts to come see really interesting companies, support the next generation of entrepreneurs and to hang out with the people that are, who knows what their background is. But it's probably really interesting. And so like doing that kind of work alongside others that make you smarter and better and are just a joy to be around is what these investor communities are all about and what is so special about them.

0:29:32 - (D): The age of AI is changing a lot of how these communities run. I want to, I would love to hear about what's happening right now. So the group seems to have grown quite a bit. 50ish members at this point, as I understand it. And you all are contemplating the next phase of the bridge journey. So it sounds like perhaps not the. Maybe it's a big decision the same way that it was to double member dues. I don't know if we're going to go up to 10k or what the next step is, But I'd love to hear what's next for Bridge.

0:30:09 - (Linda Jellison): So I guess one thing that as we speak, I think there's another key to the. I'll just step back for a second. Another key to the whole love of angel investing, and that's the entrepreneurs themselves. And so there's great people that we meet as members, as group members. It's really fun and exciting to be part of building an ecosystem in Sarasota that includes a lot more of these. But then there's also just the meaning of that and talking with and helping the entrepreneurs themselves.

0:30:42 - (Linda Jellison): So I think going forward, we have such. I feel like we have such a good balance now, and I think part of our what's next is going to be how big do we want to get? It's. To be honest, growing an angel group is like growing a company. So you start. You start out with the. With the founders and then the founders. It's a lot of fun. You grow to be 50 people. And then there are some people who don't want to be more than 50 people, and there's other people that do because they know that with that growth also comes change.

0:31:18 - (Linda Jellison): So I think that's one of our big topics. I don't even know that we. That we put raising the dues specifically on the agenda at all. I just think with the idea, I think meeting, we just want to see what is the next step for our group. Do we want to continue to recruit? Is there some way that this group morphs? Yeah, I think this was. We meet quarterly for the board, and we talk about the board business. But I think we realized there's, you know, there's all kind of changes that can be made. The way we invest as members, you know, how much we're investing.

0:31:59 - (Linda Jellison): Do we want to do more deals, smaller amounts of money? Do we want to do smaller. I mean, less deals, bigger amounts of money. So I think all of that's going to play into our conversations next week.

0:32:12 - (Peter Offringa): Yeah, I would say, you know, we're reaching an interesting inflection point. I think with. With 50 members, we're still at a level where all the members know each other. We can all fit in a room and still have a conversation that's manageable.

0:32:32 - (D): Depends on how much wine.

0:32:33 - (Peter Offringa): As we get larger. Yeah, I mean, as we get larger, let's say if we had 100 members, how would we still manage that dynamic? As you think through all of the, you know, machinations of running an angel group, you know, we still value having live meetings where we listen to pitches and we can answer, ask questions and then have a constructive conversation among the members afterwards about the companies. Well, that's easier to do when you're at 50 members versus 100.

0:33:06 - (Peter Offringa): At the same time, we want to maximize our impact. So Obviously with a 100 members or 200, we can write bigger checks and have more benefit to the startups that we choose to invest in. And of course, with bigger checks, you potentially have board seats or more involvement with the company. So that's important to us as well. So I think, yeah, big topic will be striking that balance or maintaining that balance as we grow.

0:33:37 - (Peter Offringa): I think another challenge for us is just process. Like as we see more and more companies applying for funding, you know, we, we recognize that, you know, our due diligence process could be improved and scaled. You know, whether we use more automation or we create different investment committee tracks, you know, by industry type, we want to make sure that we can capitalize on all the, you know, all the deals, all the companies that are coming through, because that pipeline keeps getting bigger and bigger.

0:34:09 - (Peter Offringa): You know, we can't have 100 people evaluate, you know, 50 companies a month, you know, individually. It's just not going to scale. And then I think the last thing that's really interesting is as you know, our, the amount of capital we have access to continues to increase. We're really trying to be thoughtful about how much growth we can engender in our own community. You know, it's interesting we pulled some stats and you know, we, we, we, we've done over half of our investments over the last eight years in the southwest Florida area, but that's really been accelerating over the last two years in terms of that proportion, you know, and I think ideally for a, for an angel group that's regionally based, you know, I think ideally 80% of one's investments, you know, the local market. And so the question for us is, or the opportunity is how can we help get more companies to choose to, you know, headquarter here and grow here so that, so that we can invest in them locally.

0:35:23 - (D): Peter, I'm glad you brought that up. One of the challenges I consistently see with region focused, region specific investor communities is they will often launch with this grandiose focus that 80% of our investment activity will be into local companies. And we're also going to run on a monthly cadence and look at four companies a month and then they realize very quickly that that is not sustainable.

0:35:49 - (D): It sounds like that tone has changed over the years as the local ecosystem has grown. Is that a challenge that you all resonate with? And if so, how has it evolved?

0:35:59 - (Peter Offringa): Oh, absolutely. When I joined five years ago, the majority of our deals were outside of Florida and I think certainly benefiting from the growth of economic activity in Florida. More and more of those deals as of late have been within Florida. And then even in the last year or two, more than half of our investments have been in the southwest Florida area, let's say within a hundred mile radius of Sarasota.

0:36:33 - (D): And why, why is that, that it's shifted so much?

0:36:35 - (Peter Offringa): I, I think a couple reasons. One, there is more startup activity here, you know, so Florida is, you know, economically, you know, growing. There's a lot more entrepreneurship than there was previously. Whether that's a reflection of. Well, it's probably a reflection of all the factors we've talked about. More entrepreneurs moving here, more capital. And so that has certainly helped us in terms of finding more deals or having more, I guess, a bigger pool of deals. I think secondarily bridge angels reputation has improved. We're more visible.

0:37:17 - (Peter Offringa): We are on more lists, if you will, of I've seen various lists of the top 10 angel groups in Florida or venture groups that you need to know or just word of mouth, you know, that more individuals are familiar with. So I think what that does is, you know, as founders are looking to do a fundraise, let's say from Florida venture capital sources, you know, our name is often on the list. We have a good reputation, you know, and we're not just a check writer. We also have great expertise. And so I think that, I think that that's really helped with the influx of, you know, higher quality deals from, you know, the local, the regional area.

0:37:56 - (Linda Jellison): I think what echo everything Peter said, in fact, I was thinking as he was speaking that early on it was just so odd if we got a company from Sarasota and typically it was somebody who had an idea and it was more like a lifestyle company. So I believe at our last screening committee we screened 40 companies. Actually it was a pre screen. Even before the screening, we screened 40 companies. Probably out of those 40 companies, what would you say, Peter? At least 10 or 11 were Sarasota based.

0:38:33 - (Linda Jellison): Yeah, which is a huge, huge change from then, from when we first started. Now I don't know if that's just because our reputation wasn't out there in terms of knowing that you could actually apply whether, you know, the word of mouth is just, I think in the last couple of years really, really increased because of Peter, like people like Peter who are not only out for, out in the community for Bridge Angels, but many other technical group. We have a ton of other members who do the same thing.

0:39:06 - (Linda Jellison): And so they're representing them themselves in maybe another group. But they're also talking about Bridge Angels, which I think then that word spreads, that word spreads even more. So I think, I think that has a lot to do with how many companies we're seeing. But I also think it has a lot to do that the growth of the tech has definitely flourished even in Sarasota here.

0:39:32 - (D): So we are recording this in September of 2026. I would love to just understand what is the mind map across the two of you for what is local entrepreneurship mean? What does it look like, who are the key players there? I've spent zero time, which we got to fix that, but I spent zero time in Sarasota County. Tell me about your ecosystem. Who's doing stuff? Who should we know about? As specific as you can be?

0:40:00 - (Peter Offringa): Yeah, no, I think that, you know, what I think is interesting for Sarasota and probably similar to other mid market communities is you know, we, we see activity but it's not, doesn't have a focus area. So like other cities perhaps, you know, we have, we have sas, we have companies that are, you know, building software solutions for various industries. We have some health care, health tech, we have some sports tech.

0:40:37 - (Peter Offringa): And you know, and a lot of those are interesting plays. And we do have, we do. One thing we do see is startups that align with the type of industries that are prevalent in Florida. So while our startups aren't necessarily doing, let's say novel research that you would see in Silicon Valley, what they're taking is concepts like software as a service, but then applying it to industries that have customers, a captive customer base in Florida.

0:41:16 - (Peter Offringa): So examples would be a company we just invested in recently in Lakewood Ranch, Florida which is a suburb of Sarasota, that created a SaaS for wealth managers. Well, what do we have a lot of insane for in Sarasota? Wealth managers. So while not necessarily a novel idea, the company has a lot of customers per se. And so we saw that one of our best investments actually came out of Tampa. They built a software platform for retirement communities. Well, what do we have a lot of in Florida? Retirement communities? So you know, building a CRM or ERP system isn't necessarily novel, but there's a large customer base. So we do see that, you know, repeating in sports, Sports tech, health tech.

0:42:02 - (Peter Offringa): So it does create some Interesting dynamics in that where it's more. The innovation is being applied to industries that have a large presence here in Florida, which does make for a successful investment. Then the other aspect to this is more formative, which is what can be a nucleus for a particular theme or thematic that then kind of everything builds on. You know, when we look to like Tampa as an example, where you know, there's a large Air force base there, CENTCOM is based there. And so as a result of that military presence, some cybersecurity companies have emerged and Tampa has developed a bit of a reputation around cybersecurity. Now know before, which recently went public, came out of there and then ReliaQuest, which is I think a $4 billion kind of private company now in the security space as alumni have know before. So they, they kind of organized around cybersecurity.

0:43:08 - (Peter Offringa): We have one asset in Sarasota, which is the Mote Marine Aquarium, which is actually doing a lot of research in the ocean technology space. And so they, they actually want to take their research and start to commercialize it. And they have focus areas in robotics, biotech, taking organisms from the ocean and applying aspects of that to either solving diseases or other bio applications. There's some big data aspects of that.

0:43:48 - (Peter Offringa): So they're looking at creating kind of an innovation park, as they call it, around the. The ocean tech space, which I think could be really exciting because that would be unique to Saraso. There aren't a lot of other cities in the country that have a large ocean technology presence.

0:44:06 - (D): It's interesting. The thing I often see is investor communities existing doesn't necessarily mean that the startup cultivation ecosystem is there as well. Like having organizations that are focused on helping companies get up and going, get trained, get ready, are a great place for the investor networks to then plug into. Do you see any builders that are really leaning in, in the Sarasota area specifically to help support, you know, entrepreneurs getting off the ground?

0:44:37 - (Peter Offringa): Yeah, I guess I'll start. So we, you know, we don't have a formal incubator or accelerator here. We do have a, an organization that started about a year ago that is a venture studio specifically. And they've had some success with their model. The core team comes up with the ideas, they kind of build them out, bring them to market and then they get funded and hire an operational team around that. And they're cooking three or four ideas which are just coming to market now.

0:45:17 - (Peter Offringa): So we feel like that's going to be a good source of, you know, of activity. We have an organization that I Am also on the board of called Sarasota Tech. This is more of a community organization which kind of anchors on or started with the idea of meetups. So we didn't have meetups in Sarasota and people came here from larger markets and said, where's the tech meetup? So we started with meetups, but it's evolved into not just monthly meetups, but we actually had a speaker conference earlier this year, and we're going to do another one next year where we rented out a large space for a full day and had speakers and panels and all tech.

0:46:04 - (Peter Offringa): And then recently we've introduced monthly, what we call special interest groups where we get, you know, invite individuals to come and listen to a talk and do some networking and. And what. What we're discovering and I think is what is another interesting and unique aspect of Sarasota is that with remote work, there's a lot of talent that's distributed throughout our area there. That talent is just working independently, often in their home.

0:46:34 - (Peter Offringa): So the classic, almost comical example is you go to these tech meetups and you meet some individual and lo and behold, they're an engineer from Amazon or Google or Facebook or, you know, some Fortun 500 company and they're doing great things, but they're just sitting in their, you know, home office all day and, you know, they don't even know that three doors down or maybe two streets away, there's another engineer doing similar stuff for another, you know, Fortune 500 or hyperscaler technology company.

0:47:06 - (Peter Offringa): And so, you know, one of our other goals with organizations like Sarasota Tech and, you know, even Bridge tries to help with that, is, you know, get. Get this talent together in a room, let them talk to each other, and then hopefully coming out of that, you know, maybe they have some shared ideas and they'll decide to do a business together.

0:47:23 - (D): Linda, did he miss anything?

0:47:25 - (Linda Jellison): He did a great job, in fact. Yes, he's the.

0:47:28 - (Peter Offringa): The.

0:47:29 - (Linda Jellison): I think all the tech startups that we have in Sarasota have really just flourished in the last couple of years. Initially, Bridge, we and still have, we have an affiliation with the Adifo family office. They're one of our biggest sponsors and they are linked to the Adidas family, who have an incubator in Orlando. So I think at the time that we were really getting some companies out of there, there really was nothing in Sarasota. So this has been a real recent development and I think it's just growing.

0:48:06 - (Linda Jellison): We don't have a college per se in Sarasota, but we have other universities that are, you know, we have University of Tampa and we have, you know, we have other universities that aren't far away. But sometimes that's a good place for, you know, having incubators for startups. So I think Sarasota realized a need for just having some here in the community and that's what's been growing up over the last couple years.

0:48:35 - (D): Final thoughts for. Let's say you are speaking to someone who's listening to this. Let's say I'm in a traditionally tourist type town, 120,000 people, let's say, got a few friends excited to try to build an investment community around it. What would be your one or two words of advice?

0:48:58 - (Linda Jellison): For me, words of advice would be to get started, don't give up just because you might stumble a little bit in the beginning. Because I think once you get the rhythm, it progresses. But I think you also have to realize that as a member led group, that member led group also needs support. They need people who a know what they're doing in terms of due diligence and investing and even legal. So you have to, I think you have to build some kind of a staff even if you're small and then you can kind of take it from there.

0:49:35 - (Linda Jellison): I don't think it's, I think it would be very difficult to grow an investment group if you're just members getting in a room because people, lives change, things happen, people aren't always available to do what they say. And then it's when you're actually working with an entrepreneur and you make a promise and the promise is we'll get back to you in a couple of weeks. They're generally counting on that, whether the answer is yes or no.

0:50:00 - (Linda Jellison): So there's a lot of timing that it's really critical to kind of stay in the mood and make sure you're getting answers back.

0:50:08 - (Peter Offringa): Yeah, I would say my coaching, particularly for a tourist oriented town like a Sarasota would be, don't be surprised by the resources that are actually available. Get the word out. You know, I think what we discovered is, you know, our assumption was there's, and I've often even heard this, you know, there's, there's no talent in Sarasota. It's all retired people. And then you get the word out and, and all of these amazing people surface who have just, you know, wonderful, deep, rich experiences and, and, and, and, and so that exists. You know, the challenge is how do you, how do you uncover those people? So let's get the word out, you know, whether it's meetups or.

0:50:50 - (Peter Offringa): Or whatever. And then. And then I think, you know, just be consistent, you know, establish, you know, some goals around investment. You know, the nice thing is, you know, getting a couple people to commit to making investments periodically probably isn't that hard. I think what is harder is just being. Having a process and being consistent, you know, whether it's meeting monthly and making it clear, you know, through a website or an app, you know, how, how founders can engage and then just repeat.

0:51:19 - (Peter Offringa): I think repeat and refine. That's what we did. It was a grind, right, Linda? For the last five or six years, it's been a grind, but we just stuck with it. And we kept doing the same thing month in and month out. And when it worked, it just takes some time.

0:51:37 - (D): Well, Linda, Peter, thank you for taking the time to speak with me today. It's been wonderful learning about your community, and I look forward very much to our next conversation.

0:51:47 - (Linda Jellison): Thank you very much.

0:51:49 - (Peter Offringa): Awesome. Appreciate it. Yeah, that was fun.

0:51:52 - (D): Thanks for listening to this episode of the Diligent Observer. I'm your host, Andrew, and if you're an angel investor looking for essential angel intel in five minutes every week, I think you'd enjoy my newsletter. I send my best stuff, interesting deals and more straight to your inbox, so you never miss a thing. Subscribe today@thediligentobserver.com.