Cloudflare vs. the Crawlers & The Nonprofit Tech Divide | [Sidecar Sync Episode 90]

Summary:

In this dog-dedicated episode of Sidecar Sync (Happy 12th to Ninja!), Amith Nagarajan and Mallory Mejias tackle two extremes of the nonprofit tech landscape. First, they dig into Cloudflare’s bold new default to block AI content scrapers—what it means for associations, the rise of pay-per-crawl, and whether blocking AI is smart strategy or short-sighted fear. Then, they shift gears to dissect a revealing Chronicle of Philanthropy survey on nonprofit tech adoption, where some orgs are experimenting with AI while others still won’t accept credit cards. The result? A growing digital divide—and plenty of lessons for association leaders looking to future-proof.

Timestamps:

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Amith Nagarajan is the Chairman of Blue Cypress 🔗 https://BlueCypress.io, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

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Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space.

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Read the Transcript

🤖 Please note this transcript was generated using (you guessed it) AI, so please excuse any errors 🤖

[00:00:00] Amith: Welcome to the Sidecar Sync Podcast, your home for all things innovation, artificial intelligence and associations.

[00:00:14] Greetings, and welcome to the Sidecar Sync, your Home for content at the intersection of artificial intelligence and all things associations. My name is Amith Nagarajan.

[00:00:24] Mallory: And my name is Mallory Mejias,

[00:00:26] Amith: and we're your hosts and, uh, can't wait to dig into these topics. Mallory, this is gonna be a fun one. How are you doing today?

[00:00:32] Mallory: I. I am doing well, Amith. I see you're in Utah. You've got your nice Utah background. How's that been?

[00:00:39] Amith: I got here last night after three days on the road, so I'll be here for a while. This is kind of our, uh, Western migration for the summer from New Orleans. And, uh, escape the heat, come up into the higher altitude and enjoy the, the, the thin clear and cooler mountain air.

[00:00:55] So I look forward to this every year. I do the drive, uh, mainly to. Bring my dogs. Uh, [00:01:00] one of my dogs turned 12 yesterday. Oh. Um, so he had his, uh, 12th birthday on the last segment of our drive out to Utah. So that was super fun. And then, uh, some of my Canadian colleagues I was speaking with reminded me that yesterday was Canada Day, so I guess my, my dog is an honorary Canadian, so it was a great day and I'm very happy to be here in Utah.

[00:01:20] How are you doing?

[00:01:22] Mallory: I'm doing well, and correct me if I'm wrong, but you like long car rides, is that correct? I know I do not like doing long drives, but I think that you do.

[00:01:31] Amith: I do. I, I have to say it's 30 hours of driving over three days, so 10 hours a day, three days in a row, couple nights in the hotel.

[00:01:38] That's not my favorite. But, uh, you know, it's just me and the dogs hanging out. My family flies and, uh, that's cool. Um, I'm, I'm actually good with that. I kinda like. The long road trips 'cause listen to a lot of podcasts, listen to some music, talk to people on the phone. Uh, see a lot of the country, you know, you kind of forget how big this country is until you take some time to drive through it.

[00:01:57] And even though I tend to take some, not [00:02:00] necessarily the exact same route, but very similar route, each time I do the drive, you see different things. You notice different things. You can stop in different places and um, you know, you just kind of. Pay attention to things that a lot of times mm-hmm. In our daily digital life, we don't pay attention to so much of what's around us.

[00:02:16] And, uh, I think that's an interesting opportunity. So I, I got a whole bunch of interesting ideas for, uh, things we can do for work and ideas for my family and stuff like that, just driving. So I, I always have found driving to be a liberating, uh, kind of adventure in a way. I love it.

[00:02:32] Mallory: Yeah, I like that it can be a bit meditative, I think.

[00:02:34] I don't like being a passenger in a long car ride. I mind less if I'm actually doing the driving myself. I wanted to ask, what is your dog's name that turned 12?

[00:02:45] Amith: His name is Ninja.

[00:02:46] Mallory: I. Ninja Turn 12. Yeah. So we're doing episode 90 of the sidecar sink. We're gonna dedicate this one to ninja's 12th birthday.

[00:02:54] Amith: Fantastic. Well, and at 12, I think in dog years, he's 84. But, uh, we can round that up. So [00:03:00] he's, oh

[00:03:00] Mallory: no, he's the, he's an old man. He's the elder.

[00:03:03] Amith: He's the elder statesman of the family. So.

[00:03:06] Mallory: We are potentially, I guess I'll share it with the audience, going to adopt a second dog. Um, we have been like looking at adoption places.

[00:03:14] We've been filling out applications. Some of these applications can be kind of intense, which is a good thing, making sure they're placing a dog with the right family. But we did just lose out on a really cute puppy because we live in an apartment. And not a house. And they said, no negotiations. There has to be a house.

[00:03:31] So hopefully in one of these future episodes I'll be coming to you guys to tell you about my new second dog.

[00:03:37] Amith: Awesome. Well good luck with that. And yeah, getting, uh, adopting a dog is amazing. Mm-hmm. Uh, that's. How Ninja came into our family, and, uh, he and his, uh, siblings were left on the side of a road in a box somewhere in rural Louisiana.

[00:03:50] And fortunately, uh, the local, the good folks who do, uh, a lot of work in in the area found, found those dogs and, uh, ninja's been part of the family since. [00:04:00] So, oh, it's quite an amazing story. And, uh, yeah, he's a, he's a great dog.

[00:04:04] Mallory: That's what we're really going for is that companion pet piece. I mean, I always say to my husband, our dog doesn't know any different.

[00:04:11] He feels bad for her because she is, you know, an only dog. But, uh, I think she lives a pretty happy life. However, it would be nice to see her play around and do things when we're in the house. When I'm working from home, maybe bark a little bit less. At the door while I'm doing the podcast, but you never know.

[00:04:27] Amith: Yeah. Or bark a little bit more 'cause they're, you know, they, one of my dogs starts barking, the other one starts barking. So, you know, we'll, we'll see what happens. Good luck with that.

[00:04:36] Mallory: Oh yeah. Thank you. Well, episode 90 in honor of Ninja, we are talking about two critical topics that represent opposite ends.

[00:04:44] Of the technology spectrum. First, we'll dive into cloud flare's, new AI blocking and pay per crawl system, a fundamental shift in how organizations can protect their valuable content from AI scrapers. Then we'll examine the Chronicle of Philanthropies new [00:05:00] nonprofit. Tech survey revealing that while some organizations worry about AI stealing their content, others are still struggling to accept things like online payments.

[00:05:09] So first I wanna talk about CloudFlare, which handles about 16% of global internet traffic. It's launched a default setting to block AI content scrapers and crawlers without explicit consent from site owners. This move is significant because AI companies have been scraping vast amounts of web content to train models without compensating or even notifying content creators.

[00:05:33] Many content creators and publishers are losing traffic and revenue as AI models answer user queries directly bypassing the original websites and undermining the traditional web ecosystem where creators are rewarded through ad revenue. The blocking system works through several mechanisms. New domains.

[00:05:50] Registering with CloudFlare are prompted to allow or block AI crawlers giving website owners direct control. All CloudFlare customers, including [00:06:00] those on the free tier, can toggle the AI scrapers and crawlers option with a single click. The system uses machine learning models and traffic analysis to detect bots, even those attempting to disguise themselves by spoofing user agents.

[00:06:14] Each request is assigned a BOT score to distinguish between legitimate users and automated scraping attempts. The real innovation though is Cloudflare's Pay Per Crawl Initiative. A new system allowing website owners to charge AI companies micro fees each time their bots crawl and scrape content. All new CloudFlare domains now block AI crawlers by default, and site owners can set specific rules, allow free access block entirely, or charge a fee per crawl.

[00:06:46] CloudFlare acts as the intermediary handling payments and tech logistics. When an AI bot requests content, it must present payment intent in its headers, publishers can monitor which bots are crawling their site, set their own prices, and view [00:07:00] detailed analytics. The system is currently in private beta with major publishers like Time in The Atlantic already participating.

[00:07:07] Now for associations who create valuable content, including research reports, educational materials, member only resources, and industry publications, all of which may be scraped for AI training without compensation. This raises some strategic questions about whether associations should, should perhaps block AI scrapers, how to balance member value.

[00:07:27] With exclusive content versus discoverability and whether pay per crawl could become a non-dues revenue stream. So a lot to unpack here. Amit, it seems like a, a major shift in the way the web works. What's your take on pay per crawl and blocking AI scrapers and all of that?

[00:07:46] Amith: So Mallory, on my long drive, one of the things I did is listen to a lot of podcasts and one podcast in particular I happened to be listening to when I was entering the state of Utah yesterday afternoon, uh, was the Google episode, uh, from the folks that acquired, which [00:08:00] is one of my favorite pods I've talked about here before.

[00:08:02] And I'm sure you've had a chance to listen to some of their stuff. They do a really good deep business history and they pick a company. And in the case of Google, this is just the first episode of several. This one I think was like three hours and 45 minutes. So there, there. Episodes tend to be much longer than the sidecar sync.

[00:08:17] They, they deeply, deeply research a company and they, they share a lot of interesting insights. So one of the things, uh, I'm linking back to what we're talking about here with Cloudflare's Move is that when you're at, uh, when you're essentially this, uh, point through which people discover content or gain value, uh, there's a lot of power there and there's a lot of opportunity there.

[00:08:35] And so the monetization aspect is very interesting. I think that could be a way for them to generate a new revenue stream. They're already doing pretty well, uh, but. Know, they, they have an opportunity for a new potential revenue stream. And I also think that the ability to like just reflexively say, Hey, we're just gonna block all crawlers, is something a lot of people will say, well, yeah, like, we're just gonna do that.

[00:08:56] And as you pointed out, since that's the default setting, uh, for [00:09:00] existing sites, I believe, uh, that would mean that, uh, people would have to go and proactively turn that back on. Uh, so what's gonna happen with this? And so many sites, uh, utilize CloudFlare services, um, you're gonna have a lot of. Uh, AI and other types of, there's lots of other crawlers by the way, not just AI will be blocked.

[00:09:18] Um, and that will have an interesting ripple effect because there's actually lots of things on the web that rely upon crawling websites. Obviously search indexes are the most obvious ones, uh, but just being able to, for example, include your content in some of your own. Uses. So let's say that you use a vendor like raa.io that uses, uh, your website as a source of content for newsletters.

[00:09:38] Well, the raa.io crawler might get blocked as well, even though it's a service you pay for to construct and build your newsletter. So, um, there's just things to be thinking about. I think there'll be some repercussions where people will flip the bit. On the other direction and say, no, it's just available for everyone.

[00:09:54] So I think it's interesting. Now, the, the broader theme that I think is worth thinking about pretty deeply for [00:10:00] association leaders is whether or not, uh, your content should be available at all publicly, should be partially available public in partially privately, uh, or exclusively privately. It's an interesting question.

[00:10:13] Uh, before Ascend, I published a different book called The Open Garden Organization, which argued that in the world we live in, and this was circa 2017, it definitely talked about AI already back then, but it was talking just generally about the business model of associations. And my argument was that trying to live in a box where people have to enter that world, that closed garden, uh, was problematic because there's too many good options out there in the world.

[00:10:38] Uh, and I still believe that's true. Um, but I, I have thought. On how you might go about being competitive, uh, in the world today. So, uh, the, the essence of which essentially is you can't ignore ai. You can't just say, you know, we're gonna push AI away. But what you can do is embrace AI for yourself and have your own contemporary cutting edge AI services of various [00:11:00] flavors.

[00:11:00] On your website available either publicly or to the members or others who pay and, and then be competitive that way. Because if you're not gonna use AI, then people are just gonna get their content somewhere else because it's just too hard to get it the traditional way. Mm-hmm. So that's, that's my initial reaction to this.

[00:11:17] Mallory: What is your gut instinct? I'm thinking the Shakespearean phrase to be or not to be, to block or not to block. What would be your gut instinct at this point, if you were an association, CEO, on whether you would want to block AI scrapers or perhaps try to monetize it? What are your thoughts?

[00:11:34] Amith: I don't know enough about how CloudFlare has implemented their feature set, and if the granularity allows you to whitelist certain crawlers.

[00:11:43] Mm-hmm. So if you could say, yes, Google can keep scraping. Yes, Bing can keep scraping. And, and yes, Bing is still out there. They still represent a portion of search traffic and there's others, uh, that are out there that do, uh, do actually provide important services that drive traffic to you. So be thoughtful about that.

[00:11:58] I wouldn't just flip it on and say, [00:12:00] Hey, like, no one can access my content, because then you're isolating yourself. So I'd be very careful about that. Even though AI tools are absolutely putting a big dent in organic web traffic through search, there's still a lot of traffic coming through search. So you wanna be careful to not turn that tap off.

[00:12:17] So that'd be one thing I'd be very thoughtful about. Um, the other thing I would say is just because you allow. Tools to scrape your content doesn't mean you're allowing them to scrape your content behind your firewall. So if you have a paywall or firewall, essentially that prevents people from in the public accessing your content, uh, like certain types of content, let's say there's certain blogs or things you put on your public website, yes, a scraper can come and grab that stuff.

[00:12:43] Um, but let's say you have, you know, really detailed and rich research reports or other kinds of information that you have to be, uh, a paying member to access. The bots can't get that. Just because they can crawl your site doesn't mean they can penetrate past a paywall. They're not hacking your website, they're just [00:13:00] grabbing what's publicly available.

[00:13:01] So also make sure to separate and not conflate those two issues. Just because you allow an AI to scrape your website does not mean at all that they're allowed to get into your private content. And a lot of people I talk to get confused by that issue. They say, oh, if I enable this, that means I'm handing over the keys to the kingdom.

[00:13:19] And that's not at all the case.

[00:13:22] Mallory: Okay, so I, I feel like there still could be value in letting these AI scrapers look at your publicly available content, because if someone is on chat, GPT or Claude and it links back to your association website, there is value in that. Um, hundred percent. So I guess it's more of an open-ended kind of discussion that will continue to have, but definitely, definitely interesting to, to discuss on the pod.

[00:13:46] Amith: Right. I mean, it's, it's like how do you stop a tornado? Well, you don't, you get to safe ground and then you come back out after it's gone through and you figure out what the world looks like. And to some people, AI feels like a tornado ripping up their hometown and it's terrible. [00:14:00] Um, but then the flip side of it is, is that when you rebuild the new world, as terrible as that destruction was, which is exactly what's happening to a lot of associations right now, it gives you an opportunity to build a new, um, without.

[00:14:13] The mindset and really the prior, you know, uh, world existing quite the same way. And so I would say also anticipate the tornado is coming and maybe build something that's not tornado proof, but perhaps even somehow harnesses the energy of the tornado to benefit you. Right? So, uh, what I'm trying to describe essentially is AI is not going away.

[00:14:34] People are not gonna stop using it. And whether or not the intellectual property issue is murky, which I think it still very much is, um, or not. People will be using it. End users are receiving so much enormity of value from using CHA pt and Claude and Gemini and all these other tools that they're not gonna stop using them.

[00:14:54] It's like if you had said, you know, prior to Google, you don't have Google, and now that Google's here, oh, well [00:15:00] actually you know what? You can't use Google anymore. For some reason, that's not gonna happen. People are just gonna come to Google because the value it created was so enormous. The same thing is happening at perhaps an even higher order of magnitude.

[00:15:10] I mean, not even perhaps is definitely an even higher level of value creation. So. You as an association can try to block it, can try to avoid it, can try to prevent it, but I, I think you have to figure out how to play nice in the world where most people get most of their information through an ai. You just have to figure that out.

[00:15:30] So there's this whole world called AI engine optimization, or ai eeo uh, one of our keynotes to digital Now in 2024, Sharon Guy brought up that topic and talked about it quite extensively. Um, and I think that there's a lot of people out there talking now about how to optimize for ai. I think it's an important thing to be thinking about.

[00:15:47] How do you make your content conceivable by ai? Like it's the inverse of this whole blocking thing. How do you make your content set up so that it's actually really helpful for the ai? Of the world to be able to read it. And there's one other reason [00:16:00] why that might be useful is that there's this concept of personal AI assistance that are, you know, around the corner.

[00:16:05] You can think, you might think you already have that in chat GPT or something like that, but you really don't. You have the same chat GPT that everyone else has, right? So Mallory, you and I, when we log into Claude, we can tailor it a little bit, but it's essentially the same model, um, the world we're heading towards and all the major vendors think this.

[00:16:22] They're all heading towards the world where you truly have personalized ais that are far more deeply tailored. And part of that will mean that, um, when I have my AI go off and do research for me, which I actually do that already with, uh, deep research and Claude and, and Google. Uh. That is also scraping.

[00:16:39] So you're gonna stop me from being able to include your website in my research activity, and that's problematic. So there's many layers to this. It's not as simple as, oh yes, they offered me to block ai. I'm worried about ai. Yes, I will turn on blocking. And if you're a CloudFlare customer, and many of you are, even if you don't realize it, many of you have CloudFlare as part of your DNS infrastructure.

[00:16:58] If not. For more [00:17:00] than that. Uh, you need to go look at this because if you're automatically blocking AI by default, that might be actually really, really bad for you in terms of traffic and just in general usability.

[00:17:10] Mallory: Mm-hmm. From the technical side, I know CloudFlare mentioned it's going to assign a bot score to identify how likely it is that it's a, a bot versus an actual user.

[00:17:22] From with your technical expertise, do you think that will get more and more difficult to do in the future to identify like an AI bot scraping your site versus another? 'cause I assume the, the bots will just get better at looking like users, if that makes sense.

[00:17:36] Amith: So, I dunno the insight of what CloudFlare is doing, but traditionally bot detection, uh, AI was looking at patterns and machine, classical machine learning, which is looking for this stuff, which is what they're using, uh, is essentially looking for like the frequency and the approach, the type of approach that.

[00:17:51] The, the kind of the order of operations. So what does a classical bot do? A bot goes to your homepage, it looks for a site map, it tries to figure out what [00:18:00] other pages are, and then it kind of in parallel will try to grab all these other pages. Most end users don't do that, right? Mm-hmm. Most end users actually end up on a landing page on your website, somewhere in your website maybe goes to a page or two, uh, whereas a bot tends to not do that.

[00:18:14] A bot tends to kind of like. Go after your whole site kind of in parallel at the same time. Or if it's not one of those, it's going kind of sequentially. One page. The next page, I found a link on a page. It's doing it quite quickly. Now, of course, people are very smart and so are ai, so they might say, Hey, let's not worry about crawling Mallory's website right away.

[00:18:31] Let's. Hit Mallory's website. Now let's get an index of what's on it, and let's just go back like a page every hour or two hours because we don't really care if we've indexed Mallory's website instantly. We can do that across all the websites. We might be indexing a million websites this way, and we can crawl Mallory's site over the next 2, 3, 4 days.

[00:18:49] That would be harder for a bot to detect what would make it more detectable to a bot. Well, you could tell me, Mallory, what would make it seem automated perhaps maybe coming in every hour. Exactly. On the hour, [00:19:00] right? Yep. I mean. Some of us might do that, but most people are a little bit more irregular than that, right?

[00:19:04] So, and there's other things like that beyond just the frequency. And so that's what these ml uh, you know, these machine learning, uh, techniques look for is, is pattern detection. They look for features in the data that essentially are detectable, and then they'll do a scoring, a probability of. Bought or not bought.

[00:19:20] Uh, but there's, it's, it's move, counter move. It's like hacking and, and uh, you know, threat detection and threat prevention and it's, it's like anything else in life. There's, there's move, counter move and, uh, that's gonna be going on with this stuff. But I, I would think, I would certainly think about that, but I would zoom out and say, what does this mean for my business?

[00:19:38] I wanna make sure that I do not penalize my customers. Do not create friction for your members, for your customers, for your users. They will be completely unforgiving as they should be because it's not their job to worry about your business model. It's their job to do whatever their job is. Um, might be as a consumer, it might be in, in whatever their line of work is.

[00:19:56] Um, so if you make your organization harder to deal with, even [00:20:00] unintentionally, you will suffer. Your members will suffer initially and then they will leave, and then you will suffer. So make sure you're not penalizing the end customer because of your concern over this. Um, and again, the other thing is, is that, you know, you can't fight the tornado.

[00:20:16] Um, you have to be aware that it's coming and you know, maybe it is gonna tear things up a bit for you initially, but there's an opportunity here as well.

[00:20:26] Mallory: Moving to topic two for today. The Chronicle of Philanthropy recently commissioned an exclusive survey conducted by Clarion Research asking over 350 nonprofit leaders about their approaches to technology, the challenges they face implementing it, and the promise they see that it holds.

[00:20:44] The findings reveal a sector at a crossroads where organizations that can't afford to modernize are pulling ahead and those that can't fear being left behind entirely. The most striking finding is the investment gap. Nearly nine in 10 nonprofit leaders [00:21:00] say technology is vital to their fundraising success.

[00:21:02] Again, this was a general survey about the, the whole nonprofit market, yet most spend less than 3% of their budgets on it. In contrast for-profit companies spit nearly 6% of their budgets on technology last year. This investment gap has made it difficult for organizations to adapt to a rapidly digitized world where AI's already disrupting industries.

[00:21:23] Many nonprofits still struggle with basic email management or cybersecurity protections. The survey reveals this is creating winners and losers in the sector. Organizations spending more than 3% of their budgets on technology are twice as likely to report using it in advanced ways. This creates a reinforcing cycle where the most digitally savvy groups attract more funding for flashy.

[00:21:47] AI driven tools, while they're less technologically sophisticated, peers fall further behind. As Melissa Luan, executive director of the Housing Nonprofit Rebuilding Together Peninsula put it, it's an endless [00:22:00] cycle of being considerate, inefficient, but then not being able to access the skills that would make us more efficient.

[00:22:06] The barriers are clear. 89% of respondents cited budget constraints as a primary barrier to technology adoption. While 64% cited lack of in-house staffing or technical expertise, two thirds of leaders think technology deficits are hampering their organization's growth with manual processes, eating up, staff time, and complicating communications.

[00:22:28] The reality on the ground is start. Some organizations still exclusively accept paper checks because they don't wanna pay credit card charges while others are experimenting with artificial intelligence. For associations, we think these findings serve as a warning and a call to action. The parallels are clear.

[00:22:45] Associations face similar budget constraints, expertise gaps, and the risk of falling behind member expectations. Amit, as I mentioned, this survey was focused on the general nonprofit market as a whole, but do you feel like the insights from the [00:23:00] survey are applicable to association specifically?

[00:23:03] Amith: Completely. They're applicable to every organization out there and to individuals as well. If you think about it, how you invest, and that's both dollars and time will determine the fate of your organization. You need to invest at a minimum, a lot of energy, and certainly dollars. Help. So if you are investing half as much, uh, in both dollars and energy, then the next organization over you can predict quite clearly exactly what's gonna happen.

[00:23:29] It's unlikely that you will keep up. It's just very simple. I mean, the report was extremely insightful on the one hand. And then the flip side of it is you can say, well, I mean, it's kind of obvious that if you invest more in technology, you're going to have more of it. Probably better technology, you're probably going to use it more 'cause it's more important to you since you've invested in it.

[00:23:50] So I think it's, uh, it's, you know, basically, uh, when you think about how an organization prioritizes the budget often tells you the story. So if you go and [00:24:00] pull the nine 90 for any not-for-profit in the United States, you can pretty quickly figure out A, what their priorities are, and B, who's in charge.

[00:24:07] So if you find them spending next to nothing on technology as a percentage of annual budget, it means they're not prioritizing it, they don't value it. It also might mean that they haven't, uh, created the right roles internally, or the roles perhaps for technology are buried somewhere within other departments and they just haven't elevated it to a function that is.

[00:24:28] Really at the importance level that it should be. So it's definitely applicable, and I should say before really going into a whole lot of detail on this topic, Mallory, especially for our perhaps newer listeners that might not be as familiar with us, um, here at Sidecar and Sidecar is part of the Blue Cypress family, is that I am deeply biased on this topic.

[00:24:46] Uh, so our family of companies sell technology solutions. Obviously sidecars in the business is selling educ. Ha, which is a form of investment in learning ai. Uh, and I've been a vendor to this community for almost 30 years. So obviously I'm [00:25:00] biased because my profession, my livelihood depends on us selling stuff to people.

[00:25:04] Um, but that doesn't mean that it's, uh, inaccurate. Right. So I just wanted to be clear that, um, there are lots of companies who wanna sell you stuff. Um, and the key to it is to separate the mindset of deflecting, the constant influx of inquiries from vendors selling you stuff, from the things that are actually gonna move the needle for your business.

[00:25:24] You should think deeply about where your opportunities are, where your problems are, um, and obviously educating yourself on capabilities of ai. Understanding AI helps you think more clearly about where you might be able to solve some of those things. And then go figure out which vendors or which technologies can help you solve the problems that you determine are important to you.

[00:25:43] Um, you know, even though I've worked with hundreds and hundreds of associations all over the world for years and years and years, I know nothing about your association compared to what, you know. Uh, I can tell you a lot about technology. I can tell you a lot about ai, but you. Know your business, you know your pain better than I ever will.

[00:25:59] And so what you have [00:26:00] to look at is, um, that analysis and that analysis is informed by your level of education on tech and on ai. And then from there prioritized, uh, you know, prioritized goals that are very clear and very simple. And then invest in those. Uh, the other thing we talk about a lot on this pod Mallory constantly is we talk about experimentation, right?

[00:26:19] And so I think this is an opportunity. Don't go invest a crazy amount of money in something just 'cause you're like, oh, we're. 3%. We need to get to 6%. Let's just throw our money at whatever. Um, even if it's a Blue Cypress company, don't do that. You know, don't just throw your money at something without thinking about it because you are behind.

[00:26:35] And by the way, I don't think associations really ever do that. It's quite the opposite. They think deeply, deeply, deeply, for a long, long time about. Every dollar they spend most of the time. Uh, but my point is this, um, you should be investing after you've had a little bit of a proof of concept. So if you think that it could be really awesome to automate, let's say your member application process, let's say in your association, signing up for membership isn't as simple as just filling out a few [00:27:00] form fields on a website and providing a credit card number.

[00:27:02] Maybe your organization has a process where people have to submit information to support that application and there's some person who has to review it. Maybe you look at that and say, yeah, we. We process 6,000 of these a year. Wouldn't it be great if the 500 a month that are going through our pipeline could be 99% automated instead of 30% automated?

[00:27:20] Sure, we'll do a little MVP, see if it actually bears fruit and then invest in it because maybe it is a massive upside for you. Uh, but again, experimentation. I guess my point is don't forget about that. Don't be like so worried that you're behind, which you probably are obviously, but like focus still on the incremental experiments and learn by making small bets.

[00:27:40] Once those bets work, just like we talked about in a recent pod about the idea of bullets and then cannonballs go big. Once you realize something works, go, go after it. Once you had empirical results that show you that there's ROI.

[00:27:55] Mallory: I wanna touch on what you said about the influx of vendor inquiries. I wrote [00:28:00] that down 'cause I thought it was a, a fun phrase.

[00:28:02] We've all been to the association focused centric events. We've seen the expo halls, we've been a part of them, right? As a part of Sidecar and the Blue Cypress family of companies. And I can imagine for association leaders, I can empathize. It's overwhelming. I like what you said about having a plan, establishing what.

[00:28:20] Is going to make an impact on your association's business model first. But my counterpoint to that is in the world of ai, often use cases are popping up, even companies that we've never thought of. So it might be an association leader who says, we've got to overhaul this membership signup process, but maybe the bigger opportunity is, um, a knowledge agent on their website.

[00:28:44] So I guess, how do you recommend kind of conducting that planning piece? And establishing what you need right now, but then also being open to perhaps something you've never considered that could be around in a month.

[00:28:56] Amith: First education. Right. I think we go back to that a lot when we talk about [00:29:00] stuff, Mallory, is that if you're not opening your mind to the idea that there's opportunities beyond what you've personally struggled with or, or thought about for years, um, you need to do that.

[00:29:10] You need to open up your mind and allow other ideas in. So education is critical. Uh, and then having. Uh, partners, they might be vendors, they might be other association executives at other groups that are perhaps further along, forming a way of, of getting insight from others who have more knowledge around AI and opportunities is important.

[00:29:29] I love the example you gave, I gave a very tactical on the ground, you know, pain point that causes staff time, but doesn't really necessarily. You know, impede the member's journey. It might slow it down just a touch, but it doesn't really harm the member journey. Uh, and, and I do think those are very valuable use cases by the way, but they're, they're kind of, there's not a lot of sizzle to that.

[00:29:47] And there isn't, uh, to your point, a fundamental shift in the business model. Whereas if you have an AI knowledge agent and you were to say to the world, Hey, listen, wouldn't it be great if we had. The, the intelligence, the [00:30:00] knowledge, and maybe even a little bit of a sliver of the wisdom of the thousand smartest members in our association all put together in one digital brain that could be available at all times to instantly answer any question and support the workflow of our members.

[00:30:16] And if you were to say that even a handful of years ago, people would've thought you were talking about something. Purely outta the realm of sci-fi, right? But now we're there and we have associations doing exactly that, uh, with knowledge agents. And that is not a thing that you would've thought to be a priority perhaps even a year ago.

[00:30:31] Maybe your association doesn't even fully realize what you can do with that technology right now. And so you're right, that might become the priority. You might say, you know what? This is such a compelling. Idea. We need to go and try this now. It's not what's, it's not what we would've said six months ago.

[00:30:47] And that's why I think the strategic planning process needs to be really thought about, uh, deeply as well. Because when you say, Hey, we're gonna do a five year plan, or even a three year plan, I don't know how you can do that. Like, I don't know how you can go into a boardroom [00:31:00] and, you know, work with your board, work with senior staff, work with an outside vendor, uh, that's helping you with the process and think that you have something that you really are gonna stick with.

[00:31:08] Certainly for, I still see people doing five-year plans, but even the three. Are plans that have become more popular. Um, maybe it's like a general directional thing, but stuff is changing so fast. You have to have a more nimble mindset.

[00:31:22] Mallory: Hmm. Yeah, I was thinking maybe five year, 10 or further than that, plans more of A-B-H-A-G thing.

[00:31:28] A big, hairy, audacious goal. Maybe just a point, a North star that you're, you're heading toward. But I, I agree with you. I cannot imagine at sidecar how we could be like in five years, here's the path we're taking.

[00:31:40] Amith: I. Right. And that's exactly right. I mean, we're saying for sidecar, you know, even the term BHAG, where it's a 15 to 20 year, uh, largely viewed as an unattainable goal, something so outlandish that people have no idea, including yourself, you have no idea how to get there.

[00:31:52] I think that's an important thing to still be, uh, directionally interesting. Um, but I think even A-B-H-A-G could be narrowed down to say, Hey, [00:32:00] this is our five year bhag. Like at Sidecar, we've said that to the world that like. We are on a very clear mission between now and the end of the decade to help educate a million association professionals around the world on ai.

[00:32:11] And we think that's important because if we help a million people in this sector learn ai, then we're helping move the needle in terms of obviously AI adoption, but more importantly, um, helping those individuals and everyone around them in their careers and helping the organizations that they are employed by, uh, not only be relevant but thrive in an a in an age of ai.

[00:32:30] But we don't know how to do that. Like, we don't know exactly how to get those million people signed up and learning and all that. And we're well on our way to, you know, having larger and large numbers, which is exciting, but it's not anywhere close to a million yet. And, uh, I think I'm confident we're gonna get there, but I don't know how to do it yet.

[00:32:45] So we're figuring that out as we go. So to your point, that's directionally the case, but our priorities that we're investing in, the things we're doing are super dynamic. We're, we're talking about a 12 month window at a time, but we're evolving them quarterly, even sometimes we change them weekly. Uh, and you [00:33:00] have to be thoughtful.

[00:33:00] Uh, you know, when John. Spence was with you recently on the pod. He talked about not shining, uh, not chasing the, uh, red shiny balls or the chasing the squirrels. And, uh, I, it's funny when I listened to that recording after you guys had a chat, I'm like, John, I know you were talking to me, um, because I'm famous for doing that, but.

[00:33:17] Uh, I hundred percent. I do. I

[00:33:18] Mallory: remember the part you're talking, we filmed that a few, a few weeks ago, but yes, I actually know the part you're talking about. I was like, are already talking about a

[00:33:25] Amith: Yep, that's exactly I think who he had in mind. At least I'm the very typical entrepreneur who likes to go after a lot of different things and I think there's, there's, there's space for that.

[00:33:33] I. But you also have to know how to stick to things to allow them to work, is what his point was, is like focus enough, don't pivot so much. We're like, oh, I'm impatient. You know, this initiative we started three weeks ago isn't working. Let's pivot. Um, you know, let's, let's focus on, on having the right balance.

[00:33:49] And, and what you have to look for are leading indicators. You have to say, Hey, um, our knowledge agent we just rolled out. Um, we don't have thousands of users on it every day, but. What are the early users saying? Are they actually receiving [00:34:00] the value we hypothesized, or is the value underwhelming? And if the value is incredible, but you only have 10 users, that's still, you made a big difference in 10 people's lives.

[00:34:09] How can we make that 50? How can we make that a hundred? And maybe you get to thousands of users soon thereafter. These things tend to mushroom, they tend to accelerate at. Unconventional rates, right? What we call exponentials, which is unconventional in most of our minds in terms of what's happened in business.

[00:34:24] Mallory, I do wanna point out one other thing that I think is really interesting is being able to punch above your weight class. Mm-hmm. Uh, put another way, associations, how can they be, how can they be as powerful as the biggest companies around the planet? Right. I've heard for decades that we can't have an experience for our customer.

[00:34:41] Quite as elegant, quite as simple, quite as clean as Amazon or Netflix, or name the company that you aspire to be more like in terms of the excellence of the customer experience, the quality of the, uh, of the work that they provide because they just don't have the resources and. I'm here to say, and I've said [00:35:00] before, that's no longer true.

[00:35:01] You have the same resources that even the largest companies on Earth have, and in fact, you have something that they don't have, which is the ability to make decisions much, much faster. Even if you're in association with a lot of committees and a lot of people with their hands in the process, you can still move faster than these behemoth organizations because you do not have the overhead, uh, and kind of the inertia of massive.

[00:35:24] Existing business models to the scale they do, you do have that. You just have a small version of that. So my point really about cost is that yes, you have to invest. Everything costs money ultimately, whether it's through time or through a direct investment of dollars. Um, but those dollars go so much further.

[00:35:41] Um, I'll give you one example. Uh, it's thematically something we've talked about a lot in the last few months on the pod, which is building. Custom software to meet your exact needs, right? You've had these, these two competing options historically, which is to try to take off the shelf software to solve a problem, or on the other end build [00:36:00] custom.

[00:36:00] People haven't really built custom except in the largest of associations for some time, um, because they've been afraid for, uh, to have to maintain it. It's expensive to build, it's hard to maintain. It ends up being buggy. Uh, it's really, really tough, but. You need to come back and reevaluate those assumptions because now using the types of tools we talk about on this pod all over and over and over again, like Claude and like others, uh, like Gemini has a new, uh, AI coding agent called Gemini, CLI, which is really awesome too.

[00:36:28] Um, you don't have those same constraints. You now have way more throughput. Every dollar you spend gets you a hundred x, a thousand x, a million x what you would've gotten. So you can create solutions on your website and internally that are. Bespoke that are tailored to your specific use cases and you can let them change over time.

[00:36:47] There's all sorts of issues to consider in that journey, but it's possible now. Whereas previously, you know, even a small change to your website might have cost you $50,000, a hundred thousand dollars, something that's just ridiculous. You can't keep doing that. [00:37:00] But now if these things are all basically, you know, close to zero in terms of incremental cost, in the grand scheme, it opens up new doors.

[00:37:06] So what I'm encouraging people to think about simply put is. Don't carry forward the assumptions of what you cannot do. Reevaluate those assumptions continuously because when you have these resources coming to you at the speed, they're coming with the power they, they have you too will benefit if you're willing to reevaluate those old assumptions.

[00:37:28] Mallory: And that's what I wanted to touch on too. So, 64% of folks in the survey cited a lack of in-house staffing or technical expertise as a barrier to technology adoption. You might wanna reevaluate that. Uh, I guess if you have no one on your team that's even a little bit, uh, technically savvy, that could be an issue.

[00:37:45] But now with things like Claude Code and like you mentioned, Gemini CL, I reevaluate what you thought prior.

[00:37:52] Amith: Yeah, I think that's the A great point, and I'd add to that it's not even so much how technically competent they are. It's how curious are they?

[00:37:59] Mallory: Hmm. [00:38:00] Well, everybody, thank you for tuning into today's episode.

[00:38:05] Happy Birthday to Ninja, 84 years old in human years. We will see you all next week.

[00:38:14] Amith: Thanks for tuning into the Sidecar Sync Podcast. If you want to dive deeper into anything mentioned in this episode, please check out the links in our show notes. And if you're looking for more in-depth AI education for you, your entire team, or your members, head to sidecar.ai.