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Navigating the Angel Investment Landscape as Investors With Ben Pidgeon

Ben Pidgeon

Ben Pidgeon is the Executive Director of VisionTech Partners, an angel investing group where inventors, entrepreneurs, investors, and universities converge to develop innovative technologies. He focuses on recruiting qualified investors, screening investment opportunities, hosting pitch events, and overseeing the group’s stringent due diligence process.

Before joining VisionTech, Ben spent 15 years in the banking industry. He was also the former President and current board member of the Venture Club of Indiana.

Here’s a glimpse of what you’ll learn:

  • Ben Pidgeon explains how VisionTech Partners help people

  • How VisionTech find investors and opportunities

  • Ben explains how they measure the success of their investors

  • VisionTech’s ideal investors’ profile

  • How VisionTech engage with its investors

  • Ben’s advice for entrepreneurs seeking angel funding

In this episode…

Angel investing is a great way to support innovative ideas and help entrepreneurs achieve their dreams. As an investor, joining a network of like-minded people is essential to make a lasting impact and achieve your financial goals.

The risk of losing money, however, is a serious and rightful concern. Ben Pidgeon recommends joining an angel investing group to learn from and collaborate with experienced investors and entrepreneurs. Whether you are a seasoned investor or just starting, having a network can allow for pooling resources, sharing collective experience, and help identify promising startups.

In this episode of The Customer Wins, Richard Walker sits down with Ben Pidgeon, Executive Director of VisionTech Partners, to discuss his journey running an angel investing group. Ben explains how VisionTech finds investors to join the group, the investment strategies, and shares advice for entrepreneurs seeking angel funding.

Resources mentioned in this episode:

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Episode Transcript:

Intro 0:02

Welcome to The Customer Wins podcast where business leaders discuss their secrets and techniques for helping their customers succeed and in turn grow their business.

Richard Walker 0:16

Hi, I'm Rich Walker, the host of The Customer Wins where I talk to business leaders about how they help their customers when and how their focus on customer experience leads to growth. past guests have included Ashton Moore of Model B and Parham Nasseri of InvestorCOM. Today I'm speaking with Ben Pidgeon, executive director of VisionTech Angels, and today's episode is brought to you by Quik! the leader in enterprise forms processing. When the last step to earning your clients business requires processing forms, don't ruin a good relationship with a bad experience. Instead, get Quik Forms, make processing forms a great experience and the easiest part of your transaction, visit to get started. Before introducing today's guests, I want to give a big thank you to Mark Firmin CEO of eTreem for introducing me to Ben. Go check out their website at where they make payment processing better. I'm really excited to introduce today's guests Ben Pidgeon, joined the Indianapolis-based VisionTech Partners and VisionTech Angels in 2016 as the organization's first executive director. Under Ben's leadership VisionTech has reviewed more than 2000 deals conducted due diligence on 100 plus companies completed 120 funding rounds with more than 200 investors writing checks. Also during this time, VisionTech Angels membership has grown to nearly 140 across Indiana and Ohio, while the group's investment portfolio has swelled to 65 companies deploying capital of over $27,000,000, three of whom had successful exits in 2023 alone. Prior to joining VisionTech, Ben spent 15 years in the banking industry, and is a former President and Board member of the Venture Club of Indiana. He's a proud husband and father to three kids plus a dog. Ben, welcome to The Customer Wins.

Ben Pidgeon 2:05

Thanks, Rich. Appreciate it.

Richard Walker 2:06

Now, look, if you haven't heard this podcast before I talk with business leaders about what they're doing to help their customers win, how they built and deliver a great customer experience. And the challenge is to grow their own company. Ben, I always want to understand business better. How does your company help people.

Ben Pidgeon 2:21

VisionTech Angels is a group of volunteer checkwers that I kind of affectionately refer to everybody. Everybody kind of opts into the deal flow. So if you think about the 27 million that we've deployed, those are coming in and anywhere from five to $25,000 checks. Wow. And so that's a lot of cat herding on my part. And that's kind of the role that I play as the professional cat herder. But we help accredited investors, evaluate select, and pool capital into a single purpose LLC, an SPV. And when you pull capital in some of the value in doing that is you can negotiate better terms, sometimes, sometimes you can take a board seat. But also, more importantly, I think you provide a longer runway for these entrepreneurs that you're trying to fund. And you can participate in a bigger round. Sometimes also, if you're writing a $25,000 check, which is often the minimum subscription amount on these unregulated securities, that's not enough to really change the outcome for the startup. It's also not enough to really spend time on any legal due diligence to make sure that you understand what you're getting into. And we will do that, we'll review the documents, we'll try to negotiate better terms, understand some sort of investment thesis around, why does this company win? Or how are they competitively positioned? What is the problem being solved. And so I liked this podcast a lot, because I ended up thinking a lot about how the entrepreneurs help their customers win. Because if they can help their customers win, that's a surefire way to create value and change the valuation of the company, and de-risk the opportunity. So you do end up thinking a lot about that, and I look at probably 400 deals a year, and maybe 80, get to the first funnel that we have. And in that funnel, we're kind of looking for market size, product status, and team. And then we'll invite six at a time to go through a screening meeting. And in that screening meeting, we're doing a little bit closer dive on, what are the milestones that are hypothesized to be able to get accomplished with this funding round? Is there a path to funding all of the milestones? That's a really important one too, because, as you think of the closest proxies if you've ever took out a construction loan for a house from a bank, and the bank underwrites the deal by looking at the builder and the plans and the after-market value. And they say, sure, we'll lend you 80% of the final value of the house, you got to come up with 20%. And then the project is 100% funded, right? But as a startup, you often have these rolling closes, which I'm not a big fan of, because you're kind of, in that example, it's kind of like, okay, if I give you $25,000, I just got your doors and windows, but we still don't have electrical. Right. It's not a real asset that you can get value out of, you can't live in it, if you partially fund it.

Richard Walker 5:42

So the entrepreneur has to keep funding and keep funding and keep funding. Yeah. And you're probably not their sole source of that funding, right?

Ben Pidgeon 5:49

No, no, we don't want to swim alone. The waters got to be warm enough for other people to jump in.

Richard Walker 5:55

I like that. So your primary customer, then is the investor. Right? And secondarily, the company that you're going to help fund, who do you find first, the opportunity that needs funding or the investor?

Ben Pidgeon 6:09

A lot of the investors are joining our network because they know somebody, they were playing golf or having drinks with somebody and they said, check out this company, I'm involved with through VisionTech. And they're curing cancer in a new way, or they're creating value some other way, I should mention that we do life science, b2b SaaS, and hard tech investments. So usually, it's some sort of conversation the investors within the network currently have, and they turn it over to their friends. And basically, that's how I find the investors. But we're always looking for new investors and trying to grow this, I'd love to see our group get to maybe 160 200 investors that participate on a deal-by-deal basis. The secondary customers, the entrepreneur, that helps us with the deal flow. And that comes from current investors, other syndicate partners that we built relationships with that are very similar to us, like other funds, other angel groups, innovation centers that are tech transfer offices, like Purdue University, IU university or Notre Dame. And then sometimes I'll reach out to somebody and say, I really liked this opportunity. I like what you're working on, tell me more. Let's see if it goes anywhere.

Richard Walker 7:26

Alright, so I'm curious how you measure success. I mean, obviously, a financial exit is amazing success, maybe the primary success, but what are the other ways that you look at that your investors are winning by working with you guys?

Ben Pidgeon 7:39

That's an interesting question, actually. Because I think there are different reasons why people write checks. This is a game filled with more valleys than peaks. But when the peaks happen, it's really exciting. And the valleys happen way before the peaks happen. So I find that investors really enjoy not only the deal flow, but the education. What's the difference between a convertible note and a participating preferred equity? What's an option pool? How does the cap table work, all that stuff? And then there's other reasons why people write checks too. Investors write a check, because they're passionate about solving whatever problem that a company is telling you that they're working on solving. And there's a conviction that's developed around solving that particular problem. So and then there's a popularity element to it, too, like, it's cocktail fodder to a certain degree.

Richard Walker 8:40

Well, yeah. So I'm also curious. I mean, you said accredited investor, I think a lot of our audience knows what that means. But do define that, what does it take to be an investor with you guys?

Ben Pidgeon 8:49

Yeah, so I think the accredited investor definition is 200,000 annual income or million dollars in net worth outside of your primary residence, or if you've invest jointly, that it's, or as a married couple $300,000 in annual income. But the way that the subscription agreements work is that you check a box on those definitions, you're not submitting any financial information to verify. That could be one of the things that changes in our industry, I think it'd be to make it a lot more challenging actually capital or early-stage companies if that happens, but maybe a business opportunity or a startup for somebody to come out with an accreditation system that you pay to be a part of, but that's, I kind of got lost in my response there.

Richard Walker 9:38

No, that's okay. I'm just thinking of the type of person who says I'm gonna go invest as an angel. I've met plenty of angel investors, but just to kind of codify it, so to speak. Is it somebody who says I want to have my fingers in a pie and be responsible and participate or is it somebody just says, it's like Monopoly board? I want to have a little bit of everything. And then I've got exposure and diversification handled in different ways, or is it really vanity like I'm on the board, or I'm part of this company that's doing this really cool Life Science Play.

Ben Pidgeon 10:10

It is vanity. But there's a couple other things that I think is worth mentioning, like these are deep out of the money options that you're hoping pay off at some point in the future. And there are other elements of, there're successful entrepreneurs that want to pay it forward. They'll join the group, and they want to lean into some of these opportunities and help give advice, be a sounding board, try to eliminate the echo chamber. And there's quite a bit of pay it forward. I've experienced this myself, so I want to make sure that somebody else isn't experienced the same way that I did. I like when that happens, because usually, it also means that somebody's got knowledge about an industry and can help us de-risk it. But yeah, I mean, it's vanity, it's paid forward. It's education. It's access to deal flow. I mean, I do think that this is an important asset class, I'm clearly biased. I mean, this is my sole job. So let's recognize that there are biases, but I also kind of wonder, like, I feel like the pace of conversations around participating in IPOs, maybe not this year, but certainly in prior years, it felt like all the value was extracted before that IPO. And I think it was because a lot of the large VC funds, extracted all that value with these mega-rounds that happened where the companies were worth $9 billion, or what have you, right, so by the time that, you know, the company is ready to go public and potentially clean up the cap table, you've created a scenario where to get liquidity, you end up going IPO but the IPO is not worth more than, it might even be lower than what the last price a fundraising happens. So it's a really odd dynamic. And so I think the return shifted earlier in the lifecycle, if the VCs went earlier than that kind of trickled down into the earlier investors needing to be in, in a different asset class that is much more risky. I mean, calling the winners is so difficult to do. I don't know anybody that can consistently call the winners. But it's a tremendous amount of fun to sit down across the table from a founder, that's really smart engineer and ask them what they think about the market and what they know. And try to help them out with some business acumen and say, well, yeah, but what's the business model do? How does that work? I always kind of laugh too. This is probably anecdotally, but there's an infinite supply market demand to sell $1 for 90 cents. Right? Right. Like what have you really done, that's a losing business model. So you really got to make sure that you can deliver whatever problem you're solving and generate a margin that makes your business sustainable.

Richard Walker 13:02

Yeah. I think for somebody like myself, and I have been an angel investor, I have put money in and lost it and been part of a board and seen it go through all of its stages. I think part of it for an investor is also the ability to participate without having to be in the day-to-day, because I don't know that I ever want to start another company from scratch the way I did my current company 20 years ago. And I don't think I'd ever have to because I'd have more financial capital at my disposal. But I don't even know if I want to go through those growing pains again, I'd rather watch somebody else do it, and maybe give them some help along the way. So I think it's really cool that you're bringing this capability together. This community of investors that you have, do you build experiences for them? Do you bring them together to golf tournaments? I mean, how do you really engage with them?

Ben Pidgeon 13:50

Yeah, we get together once every other month and listen to two pitches. And then I do a breakfast with Ben. And we usually do a cocktail hour a couple of times a year, but in December, last December, I'm probably going to do it again this year. But last December, we did a tiki-themed holiday party, where everybody got together and we got, I been to a million pitch competitions where you see 60-second pitches, and you don't have enough time to really understand what the risks are, what the opportunity is. And I don't think anybody, this made for TV stuff like Shark Tank, you don't get to see the three or four hours of due diligence that ends up getting completed. So we get together once a year. The CEOs that can make it and the investors that can make it. So we usually get about 60 or 70 people in a room. And last year what we did what was super fun was getting the CEOs to submit a bit of obscure trivia about their company or about them. And I put it down on a list. And if you could talk to everybody on the list and find out who the answer was then you got entered into a raffle to win some, like a bottle of bourbon, or something like that. So some really, really fun ways to kind of force interaction and get some conversations flowing.

Richard Walker 13:50

Yeah, like that. So I'm also curious, then, do you measure outcome of those types of events and interactions? Do you see deal flows go up or investors put their money in? Is there a co-relations?

Ben Pidgeon 15:20

Yeah, there's a correlation. I don't know that I've measured it. I could speak anecdotally. But yeah, I mean, when you get in the same room, and you're sitting across the table from somebody, you've already gotten a check for, you kind of, my light is on a sensor here. Hold on a second. You do you're building trust, right? And if the if the average check size here is five grand, and you're listening to the company on the milestones that they told you, they're gonna complete or accomplish, and either they have been doing them or they haven't, and you get to see the conviction in their eyes and make a decision on whether or not you want to jump in again and see where the company's going? I got to tell you that the one thing that's kind of wild, and it makes angel investing so unique is, the first check is kind of like an anti, like, it's a seat at the table. And after you write that check, you get to see how the entrepreneur, as you've seen, how do they interact with you as an investor post-funding, and when they come back for the second round of funding, because they always do, and milestones are always delayed. You look back on how they treated you and say, well, is this how they're gonna treat me after I write this next check that might be bigger. And there's three categories typically, that that second ask comes from the first one is, gee, the company is doing really well. And I'm super excited about what is going on, they're clearly hit their milestones. Revenue, traction is there, they told me they were going to do X, Y, and Z. And they did X, Y, and Z. So this feels like a winner, the third category, and that's a small sliver, the third category, I'll come back to the second one. But the third category is the exact opposite. This is not going anywhere, I haven't heard from them in 12 months, and they're telling me they're going to run out of money. They can't make payroll in two weeks, unless I write another check. Terrible position. I think, if you're an angel investor, or if you're thinking about getting an angel investing, that's a conversation that will happen. We are two weeks away from running out of money, and I can't make payroll. And those are tough conversations to have. They need to be had. But what happened in between the time that I wrote you the check and now? I mean, did you communicate with me between then and now. And that's also a pretty small seller, the bulk of the three standard deviations of requests is in the gray area where some of the milestones hit, but some of them didn't. So it's not really clear on whether or not they've created value or changed the direction of the company. So as an investor, you got to see, were they intellectually honest about how they approached their business and the feedback they got from the market? Did they react? And then you got to form a thesis on whether or not you're going to participate again?

Richard Walker 18:23

Well, and that's where your value is coming into play, right? Because you talk to so many companies and the investor may not, they may have some experience with their own experiences plus a couple of companies, but you're talking to lots of companies over a longer period of time, you and your team are probably in a better place to help that investor discern the truth, or the potential value of what's going on.

Ben Pidgeon 18:44

Yeah, actually a good best practice, this is free advice that I think is really fun to do. The value of writing an investment memo, when you write the check, and documenting the assumptions, and the thesis on why you think it's a winning bet, at that time that you write that check is a is a valuable document to help you evaluate that next check.

Richard Walker 19:09

So as an investor, you're saying, as you write that check, write down why are you investing? What is it you saw? What do you think the opportunity is? And this is really good, because I've been in a situation on the board of another company where what happened nine months ago to get money has completely changed to today. And in fact that those milestones weren't hit, there was a pivot in the strategy, there was a whole change in the focus of the business, that kind of stuff. And here we are, again, asking for money. So now, what is the thesis or two word?

Ben Pidgeon 19:40

Yeah, and I said, it's important, I probably was a little strong in that, but it's a great document to go back and look at, right, because then you could say, well, what was it and if there was a pivot, then these milestones that were defined or what I thought the thesis was incorrect, but did they communicate To you, did they outline? Does the logic that they use to go into the new direction makes sense?

Richard Walker 20:07

Well, I know you're not a financial adviser, but in financial advisement, we would often sit with a customer and say, what is your investment strategy? What does it need to be based on your risk profile, your timeline, your horizon, your financial capabilities, etc, and you want to have that written down, especially when the customer comes back and says, I'm scared of the market, I want to pull all my money or I've got this new, great thing I want to put my money into. Ben, I remember, and I think this equates a little bit to how some of your investors might work. But I remember as a financial advisor, my mentor, and I had a client, who just wanted to keep gambling as money in the stock market. And he said, take 5% of your portfolio, go have fun, go do whatever you want. He's like, no, I want to put in more. He's like, I have a better idea. Let's take all your money, you have a million dollars, you need $2 million to retire, let's take all your money to Vegas today at bet on black. I would never do that. I can't risk that much, then why are you playing this game? And so I think the good way to look at this is to cordon off some of your portfolio that you're willing to lose on these high-risk bets, right and put them into a system like you're offering. So I'm also curious, something else? What is the best advice you could give to an entrepreneur who is seeking angel funding, so that they don't have that communication problem? Or that they are in a better position to ask for the second, third, fourth round?

Ben Pidgeon 21:23

Yeah, this is gonna be a long answer. And I'll do my best to kind of answer it succinctly advice to entrepreneurs, understand your cap table, understand your ownership percentage that you have, how much you're giving away when you're bringing in capital, I think it also is really important to understand, like the pressures on once you take outside capital, you have to perform, we were testing a thesis, and you are accountable to a shareholder, a group of investors that want to see you succeed, and likely, they're your best advocates for that next round of funding. So you need to bring them along in the journey that you're going to experience. So quarterly communications at a minimum, maybe monthly communications in some situations, but communicate the efforts that you're doing, what's happened historically, in the last month, or since the last communication? What can I expect for the next period of time as in terms of accomplishment, but understanding your cap table communication, and I go back to this, what are the milestones? What are you going to accomplish with the money that you're gonna get today. So if you're gonna raise a million dollars, a million and a half dollars, you need to tie that to specific milestones that are smart. And a timeline, usually 12 to 24 months. And in order to de-risk it as an angel investor, what you end up thinking about is, sure my money comes together with a million dollars, whatever, you get your 18 months of runway, but do the milestones that you're defining get accomplished before you run out of money? Do you get there in month 12, and you still have six months of runway and that's the moment that you're going to go out for your next round of funding, because it's going to take six months to fundraise. And the better you can manage, and balance those interests and communicate what's going on with your business with external interests, the better you are positioned to receive that next round of funding. Now, the other thing that I would say as to everybody says, well, and this is part of the reason why I say no your cap table and how it works and really know the risk of the convertible note or the safe. But I say that because you could go to market and try to raise money on a $20 million valuation hypothetically right. But if you're raising 2 million on a 20-year post would be 22. And you've got a 10% ownership stake that you're selling. And if you have no revenue, you haven't figured out product market fit, there's still a tremendous amount of risk on the table, you might find a coastal investor to give you that $2 million, because of the idea. It, it might take you two years to find that person. So now there's timing risk. If anybody else in the market sees the same problem that you do, right, you may lose out on that opportunity. Do you want to take two years to fundraise? Maybe not. Alternatively, you could be raising $200,000 on a $2 million valuation and get it done in two weeks. Right. But again, you're kind of balancing this, gee, I can accomplish a lot more with 2 million what can I really do with 200,000 But you're giving up the same equity.

Richard Walker 24:51

I have two friends who have built businesses over multiple year periods that did that and small little pieces. 100,000 here 50,000 here 200,000 here and then it just kept going and kept growing. And they kept hitting milestones, but they never got to a point of like, I'm gonna go raise 10 million or something like that. You make me think of something else when we talk about opportunity, like artificial intelligence is one of the hottest topics right now. And I think in the past year, over 10,000, new products are now AI, they all just came out suddenly. Do you guys invest in AI-driven solutions?

Ben Pidgeon 25:23

Yeah, so the answer is no, I have not yet. I'm absolutely willing to look at it. I'm seeking out opportunities in AI. I think there's massive productivity increases coming in the pipeline. But I think that a lot of the 10,000 options out there have unproven business models, or unproven value propositions that are use cases that are still being validated. And so until I see that, that business case, where I can get in early enough is when we'll probably write that first check. But I would not play ostrich with AI, I think to totally ignore it and say it's not going to become a thing. It's just a fad is probably the equivalent of Kodak saying we don't need to worry about digital cameras.

Richard Walker 26:12

Yeah, part of the way I look at it, we're coming out with a product this fall, and it is driven by AI tool sets. But I feel like AI has become such a buzzword, it's almost a negative to attach my product to AI. And really what I think about it, as was the fundamental problem we're solving, who cares how we're solving it, can we solve it? Yeah, we can solve it now. Because these tools are available to us. We may not have been able to do that two years ago. But I think if you have the fundamentals in place, especially if you have a human component to it that is irreplaceable, like any kind of concept of AI today, then you have a more defensible product and therefore a better position to go after a market.

Ben Pidgeon 26:54

So on that topic, actually, I totally agree. I think what AI does is enables a process power. There's a framework that I like to reference called the 7 Powers by Hamilton Helmer. And one of his powers is process power, which is basically your ability to deliver a solution at a lower cost than anybody else. And I think that's exactly what AI could be doing in your use case, right? If you're out there offering a solution or a job to be done at a significantly reduced cost than was traditionally in terms of hours spent, or just processing, I think AI can step up into that processing power, under a great definition and create sustainable value.

Richard Walker 27:46

Yeah, it's funny, I often tell entrepreneurs, because I started my first business when I was 12. I've started 10 companies. And I love talking to people who want to become entrepreneurs, or have just become I say, look, your first idea is not your best idea. It's the one that got you started. And here I am in year 21. And I think our new product called Form Extract is the best idea we've ever had. And part of that reason for that is because we built this legacy and this history and this content expertise. And now we know how to apply the AI-driven tool to a new problem that our audience wants, which is how do I get data off forms? So I think when entrepreneurs, they often think of the pivot like I've got to switch gears entirely. I don't think of pivot, I think of an expansion in addition to what we're doing to address product needs and problems that we can only see because we've been doing it long enough. Ben, look, we have to wrap up here. So before I do that, I want to ask you another question. How should people connect with you? What's the best way to find you?

Ben Pidgeon 28:44

Yeah, I'm happy to connect on LinkedIn. Find me at Ben Pidgeon on LinkedIn under VisionTech, or go to And always looking for new investors. So either one of those is a great way to connect. Can I get my email? Yeah, please. Whatever you want. Shoot me an email at

Richard Walker 29:11

Perfect. Awesome. All right. So here's my last question. Who has had the biggest impact on your leadership style or how you approach your role today?

Ben Pidgeon 29:19

Yeah, I talked about this a little bit earlier. And I think I've got a couple of people that I immediately we go to and one is Tony Petrucciani, he's the managing partner of VisionTech, great guy, intellectual, plays devil's advocate, helps when you problem solve, make decisions, and is just really funny to talk to. He's a great guy. And the other two people I'd like to mention are Todd and Kim Saxton. Todd is the strategy professor I had my MBA program at Kelly. And Kim is the marketing professor that I had an MBA Kelly. So just great individuals. I think a lot of what I end up doing is kind of honing the skill of critical thinking. And when you say what is critical thinking? And I like that question a lot, because the first time I heard it, I was like, well, you think critically, and it's not, I think the critical thinking piece is like being intellectually honest and assessing the inputs and the desired outputs and understanding your resource constraints and where power lies and then applying all these methodologies to try to make some sort of thesis come up and I don't think I could be here without those three people. And there's probably many more that I'm missing out on. But those come to mind right now.

Richard Walker 30:45

And I love it. I love hearing about people have influenced you and how they've influenced you. Which is why I love asking this question. You actually made me think of my high school government teacher who made us debate, the opposite thing we prepared to debate, right? Yeah, it just opened our eyes to like, well, wait a minute, we have to see the other perspectives debate our own perspective so well. So that's awesome. I want to give a big thank you to Ben Pidgeon, executive director of VisionTech Partners for being on this episode of The Customer Wins. Go check out Ben's website at And don't forget to check out Quik! at where we make processing forums easy. I hope you've enjoyed this discussion, will click the like button and share with someone and subscribe to our channels for future episodes of The Customers Win. Ben, thank you so much for joining me today.

Ben Pidgeon 31:36

It was a pleasure to chat. Thank you Rich.

Outro 31:39

Thanks for listening to The Customer Wins podcast. We'll see you again next time and be sure to click subscribe to get future episodes.


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