If you're heading to Pax8 Beyond—or any major MSP channel event—this episode is your tactical prep guide.
Channel legend Len DiCostanzo joins host Carrie Richardson to share strategic insights from his 40+ years in the IT channel, including leadership roles at Autotask, Kaseya, and Datto. Now leading the coaching and consulting practice at MSP Toolkit, Len helps vendors and MSPs alike improve their partner programs and sales performance—and in this conversation, he breaks down what it really takes to make an event worth the investment.
You’ll learn:
- The top mistakes vendors make when exhibiting at trade shows
- What to do instead of hiding behind your booth table
- How to evaluate your event ROI—and what metrics actually matter
- Why relationships, not branding, drive long-term value
- Tips for making every handshake, hallway chat, and happy hour count
Whether you're a first-time sponsor or a seasoned exhibitor, this episode delivers real-world advice to help you turn event spend into sales results.
Find Fox & Crow Group at booth 929 at Pax 8 Beyond.
Read the blog post inspired by the interview here.
Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?
Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success.
Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.
Carrie has helped create and execute successful outbound sales strategies for over 1200 technology-focused businesses including MSPs, manufacturers, distributors and SaaS firms.
Learn more at www.foxcrowgroup.com
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hi, I'm Len De Costanzo.
Carrie Richardson:Good afternoon everybody. Welcome to Win. We're here with a channel legend.
Len DiCostanza:Yes,
Carrie Richardson:A man who needs no introduction, because if you've been in the channel for any time at all, you've probably seen him somewhere already.
Len DiCostanza:Yes.
Carrie Richardson:Thanks for joining us today.
Len DiCostanza:Yeah, Carrie, you say, I've been around and I have been around, but I will tell, and you say, people have seen me somewhere. You're pretty much in that category at this point in your career too. I think we've both
Carrie Richardson:got the the hair to show for it now.
Len DiCostanza:Yeah. We've gotten, we got the experience and the lines to show it, but, it's all good. I've been in this channel now four decades, believe it or not. Literally four decades plus actually,'cause I started my solution provider business 1983, while I was working at and t, my first year outta college, bought a PC and I started writing code on a single floppy pc. And my dad had some friends who had businesses. Next thing I know, I'm writing applications on a pc. And then this thing, the hard drive came out. And I was like, wow, I got a lot of storage room and was able to write code that stored data on a hard drive. And then networks came out and you connected a bunch of computers together and then a big server and then multi-locations. I've seen everything from the MSP or solution provider side. I built my MSP probably. Mid late nineties, I started charging my clients recurring revenue. It wasn't called managed services at the time for me. I went around presenting, probably starting in 97, 98, about my recurring revenue model, and I called it RP Square. So I built my recurring revenue model. And then I remember when we got acquired by a publicly traded company, I built the first partner program to attract MSPs to use our service desk. And I called the program RP Squared Recurring Revenue Partner Program. That was like 2001, and then MSP terms started coming around. So I've been around since it started and I was probably charging 200 plus a user in 97, 98 and telling people about my BTD model, my business technology department model, where I charged a flat rate per user to be the IT department for my clients. So been interesting to watch this market develop and change over my decades in the channel. And here I am today taking all that experience and knowledge, not only as the MSP, but working for vendors like Autotask, where we grew from maybe 800 partners when I joined, but when we were acquired the first time by Vista Equity Partners, and then the second time by Vista in a larger fund and merged with Datto, we had close to 10,000 partners and, that was a fun ride. So I went from being on the MSP side to then coaching MSPs. Actually I had a stint at Kaseya before Autotask as a third party expert for two years helping Kaseya build their MSP channel in the beginning. And then joined Autotask and then we merged with Datto. After Datto, I worked with a company of Cordo Built, helped build their partner program. And we were doing pretty well. We sold that business and. Probably, I guess start of COVID. I started consulting and now I'm MSP toolkit where I actually coach and help vendors build, go to market strategies, partner programs for the channel. MSPs, TSPs, TSDs, distributors, basically whatever acronym you want to throw out there. I help vendors go to market in the channel and build their alternate sales channel. I've been working with MSP still. I probably have coached, thousands of MSPs perhaps. Taking all that experience into MSP toolkit over the last six years, not only working with vendors, helping'em go to market, but also working with their partners and helping them improve operational maturity, grow their revenue, and usually around that vendor's product set. But it's been a lot of fun working in this industry. Carrie, I got to meet you.
Carrie Richardson:That probably makes the journey worth it.
Len DiCostanza:I'm trying to remember how we met
Carrie Richardson:We have a couple of six degrees of separations, because I worked for Mark Cattini at MapInfo.
Len DiCostanza:Oh, that's right. Yes. So at some
Carrie Richardson:point our paths might have crossed
Len DiCostanza:I don't remember the first time we met or how we met, but I, I remember just going, oh, that's what this industry needs. People who find leads make phone calls. I think that was one of the things MSPs were not so good at, coming most of them from a technical background, although now you'll see maybe more business focus folks. But certainly that was a huge need that I think you filled. And I remember grabbing you in for a webinar, one of your first webinars, and then saying, Hey Carrie, we're doing a show in Dallas. Why don't you come speak? It was your first speaking slot.
Carrie Richardson:Yep.
Len DiCostanza:And, we chatted and you like to bring up that I we worked together to get you on the stage for the first time.
Carrie Richardson:I had said that I was nervous and he is and you said don't tell people that.
Len DiCostanza:Yeah.
Carrie Richardson:People paid money to come here and to you talk. Something like that. I guess I'm not anxious when I go on stage anymore, like maybe when I'm speaking in front of a large in-person group, but. The first time it was a webinar and I'd never spoken a webinar where I couldn't see the response from people or hear them or, and it felt like I was just talking into a void. You have to hope that the joke was funny. You have no way of knowing.
Len DiCostanza:Yeah. And think about what you just said. So we probably did that webinar in the 20 11, 12 timeframe maybe. Think about it. We were using a WebEx platform and I always wanted to have video. And they would be like, no, WebEx can't handle it. And I think we tried looking at a couple of other platforms, but doing a webinar without being on screen. And or seeing your audience, right? Yeah. Now if I'm working I remember doing some work with ConnectWise, building out their partner program for cybersecurity and training the global sales team of, 400 people and literally had a big TV screen in the conference room during COVID and seeing everybody, 400 faces on a screen. We've definitely seen a lot of change. And growth in this channel. I think, I think we're here, maybe chatting about PAX eight beyond, we've seen this industry grow to where you can go to a PAX eight beyond and they're gonna have, what, 3000 MSPs? We did Autotask Community Live, our biggest conference. I think we had maybe 1200 MSPs attend, and that was pretty big. And then Dattocon got to, two, 3000 and ConnectWise IT Nation, and now you're at. Pax eight Beyond who, what, three years ago? Didn't even have a conference.
Carrie Richardson:Originally they were gonna have their first event in 2020 or 2021. And COVID, they waited a few more years and they were far better positioned to run an event of that size and caliber by 2023 when they launched. So the few extra years just helped them evolve into a better environment. Next year nobody knows. They haven't told anyone where they're going, which I'm excited about. I'm hoping it's not Orlando.
Len DiCostanza:Yeah. Wow. So this is actually my first PAX eight beyond,
Carrie Richardson:oh, very nice.
Len DiCostanza:I ran into Rob in Las Vegas at Channel Partners. He said he is doing his MSP Legends video. I should come out, they'll be filming out there. So he gave me an invite and I'm like, how could I. How could I say, how could I say no to Rob
Carrie Richardson:MSP legend series is really good. The Pax eight content team is extraordinary.
Len DiCostanza:It looks really good. So hopefully I get to, have a few words on there. Carrie, are you on there?
Carrie Richardson:I am on there. Yeah.
Len DiCostanza:I was just checking the agenda out actually, they're waiting obviously till the very end. To keep people waiting. But you have Neil deGrasse Tyson coming at the end of the event.
Carrie Richardson:Oh, I didn't know he was speaking. That's awesome.
Len DiCostanza:Rob announced, I saw it on LinkedIn and now it's up on the website let's see.
Carrie Richardson:I'm still waiting to find out who the musical guest is.
Len DiCostanza:Yeah I'm sure it'll be somebody good, I'm sure.
Carrie Richardson:You've been to and organized events of this size. What are your key takeaways for vendors who are sponsoring for the first time? How do you manage your time at an event of this size?
Len DiCostanza:Yeah. It's interesting, Carrie, right? We've been to so many events and one year at Autotask we did over 300 events around the world Organizing them is one side of it, right? And your own vendor team getting everybody ready. The other is the attendees getting ready. So you gotta get ready from multiple sides. But I always would tell my vendors who are sponsoring, I'll give you maybe just an example of what kind of coaching you might give. But you go to your own event and you see a vendor sitting behind their table in the booth with their laptop open. They're maybe doing emails or something. And I remember at one show that particular vendor that I observed doing that said they didn't really have a great show and we chatted and then it became part of what I would tell every other vendor, put your table to the side, put your table in the back of the room and be front and center. Be out in the aisle and engage the attendees. You can't be a vendor and expect. Somebody to just come in and want to talk to you, unless maybe they're incented to do that by, oh, I, let me check off this card and say I visited this vendor. But if you wanna have a good show, you have gotta be out there. I. Probably some of our largest customers. I remember even coaching my own team when we were at an event and that's get out there, you see that person walking here, watch this. Hey, what's going on? How's the show going for you? And then the guy will come over and talk to the booth or the young lady. And next thing they're managing 10,000 endpoints and they have a need for what we're providing. So if you're not. Engaging. That's rule number one. You're sponsoring. Make sure you're engaging, make sure you're front and center. Don't hide behind a desk, a chair, or your laptop and so that, that's definitely one of my first and I think most important recommendations. And the second. Make sure you're hanging out at all the events, all the networking, I think a lot of times vendors take their own team or a small, it's okay to take a small group out to dinner of MSBs you want, we all have done it, but just make sure you're present at. All the networking events, don't cut out and go do your thing. If there's something going on at the show, that's why you're there. Be there and be present. And I think it's always about being present and engaging.'cause Carrie it's a relationship business. And if you're not building the relationships, then you're not part of it. You're not part of the community that, that is the MSP community. Be present, be involved, and participate.
Carrie Richardson:What key performance indicators would you hold your team accountable to if you sent them to an event without you?
Len DiCostanza:Whether you're there or not, obviously you would know as good as anyone. You need to come away with leads, interested potential partners or existing partners that wanna look at the larger catalog of offerings you might have. You have to have a good process to. I wanna say, you don't wanna look at an MSP as a lead, but at the end of the day, that's what you're there for, right? Is how do you track your leads? How do you collect them at they show, and how do you quickly turn those leads into an actionable kind of follow up, What did they say in terms of their level of interest? And make sure not only you're tracking the leads, but we used to have our guys, and this is again before some of the newer technology, which. Is immediate, but hey you take a business card, you write on the back, or you fill out a form, take pictures of those things, send them right back, and somebody back in the end would enter it.
Carrie Richardson:We're still doing it that way. I've had too many of those lead scanners fail or people put junk into their registration form. So when you scan the badge, you're getting their Gmail account
Len DiCostanza:yeah. So it's gotta be, how many, that's number one metric. How many leads, how many interactions are you having and what level of interest?
Carrie Richardson:What's reasonable though, if you so look at an ASCII event, for example, where there might be a couple hundred MSPs versus Pax 8 beyond where there's gonna be 3000, how should your expectations be different? Can you talk to more people when there's 3000 of them, or are you still only going to attract the same hundred people you might have spoken to at asci?
Len DiCostanza:The more people you have, more opportunity for sure, you should definitely expect more leads. One of the other things I would say is if you're gonna spend money to go to an event, and you know this too, is like try to get a speaking slot.'cause usually you get a speaking slot, you're paying at a certain level where you might actually get the attendee list itself. You're definitely gonna speak to more folks. But if you want to maximize, you should definitely look for a speaking slot, get on the breakout stage or the main stage. Based on the size and you get a list, now people have all seen you on stage. That's what, we used to do and we love to get on the stage and I was fortunate enough to be that guy on the stage. You're gonna see more leads, but I also think, how big is the team going? If you're at a bigger show, you probably should send more than the two people you send to asci because you're gonna see naturally more people. I look for a breakout or some other event, maybe grab a couple of your existing partners, always have them hanging out with you at the booth, wherever you can. Potentially set up an area in the bar where, Rob was a master at this. I used to say, darn, I wish I had your budget. We laugh a little bit about it'cause when you can sit at the bar and chat with MSPs and offer a cocktail and, it's it's a great way to network and open up conversation. So make sure not only are you meeting them at networking events at your booth, hit that hotel bar, always stay at that onsite hotel. I think a lot of vendors sometimes will be what do you call it, dollar wise, pound foolish. And if you're not at the venue, then realize, you're probably not gonna go back to your room that much and just plan on being at the venue hotel.
Carrie Richardson:If you haven't booked your room for PAX eight beyond, you're not getting one. So it's time to start looking at those offsite alternatives and yeah, we had somebody suggest that you could just sit on that bus in between the hotel and the event and just chat with people all day.
Len DiCostanza:I did a little work with a company that's what they did at IT Nation. They didn't sponsor the event, but they sponsored a bus taking people from the airport to the event. That's actually another little tip. Be creative, right? They sponsored the bus going from the airport to the hotel, and they had a nice captive audience of whoever got in that bus that they could tell the story.
Carrie Richardson:What do you think is the most interesting thing that you guys ever came up with at Autotask or for any of the vendors that you supported over the last 20 years?
Len DiCostanza:Oh my gosh. For us it was just throwing a, I don't wanna say a big ass party, but I guess I did, and I think now every, so if you go to an event and it's not your event, and I think for us it was SMB Nation, I still get folks who run into me and say that it was the best party they were ever at, and we basically rent it out. A room next to Pure nightclub, I think it was Pure nightclub in Caesar's. And we had, maybe a couple of hundred people from the SMB Nation event. And then it drove us for other events to do parties or whatever. But yeah, we did a big party, had everyone there, and then you got free admission into the club at 11 o'clock they opened the doors'cause we were right into the club. And it's pretty ironic now. I was just thinking about how people were so pumped because. When we went in the club, it was p Diddy's birthday and he unveiled Ciroc vodka and he was up on the stage partying and everybody was just like, oh my God. And it's p Diddy's birthday in Pure Night Club. I think for us that, that was great.'cause we really met a lot of MSPs that became our partners. From that moment on and stayed with us, certainly for the decade I was there and beyond. It's, again, it's a community. People wanna have fun, they wanna build relationships. So whatever you can do to bring people together and make'em have some fun, they're gonna remember it. And I would say any vendor that used to come to Autotask Community live our big event, if they said, all right, we're sponsoring this big party and. They just that's when they scooped up. So do something that just brings people in and makes'em have fun at your expense. That's the other thing. It's very expensive and that's when it's more than leads, then you're tracking the sales that came from the leads, what you always want to do, you want to definitely not only track your leads, but then make sure you're tracking every one of your events and everything that you do, all the money you spend to get a lead, and then do those leads, convert, and. I think that'll drive what you do next. It's leads and conversions that are really key
Carrie Richardson:What do you think a reasonable conversion rate for a software company at an event like this is?
Len DiCostanza:You obviously gotta go for the best you can. We just basically used to go how much does a lead normally cost us? And how much does it normally convert? And you just try to go with your norms. I don't really wanna put a number on it because it depends on your product. I work with my vendor clients now, and if you have an easy product that maybe an MSP doesn't have in their toolkit yet, you probably want to see higher leads and more conversions. If you have a"me too" product maybe your conversion rate's gonna be lower'cause you gotta do a rip and replace. You just gotta really think through your product set, where you fit, what's competition look like, and you wanna meet as many people as you can and obviously convert as much as you can. It's really gonna be based on your product and where it fits in the MSP toolkit, to be funny a little MSP toolkit. What would you see as a good number?
Carrie Richardson:I don't know. For us, we're like, I usually look at alright, what's our break even point? How many partners do we need to secure from this event in order for us to consider it being cost neutral? So looking at, what is our t and e for the event? How much did it cost us to go there? And to date it's been me and Ian. But now that we have team members, we're gonna be bringing more people with us. And now our costs are going up.
Len DiCostanza:That's what I mean. It's hard to put a number on it.
Carrie Richardson:So if Len can't put a number on it, what luck do the rest of us have?
Len DiCostanza:The only way you're gonna put a number on it is backing into it. That's really how we started out going about it. I'm going there. I spent this much on the show. Our typical deal is. X and our typical MSP partner size is Y and you gotta say, I need to get, 20 deals out of this that, do business with us. Which means if I have a, 20% close rate, typically that means I need a hundred leads to close 20 to cover my investment. It's hard to put a number on it'cause it's based on so many factors. You kinda have to take each individual show. On its own and what you're spending and what you're looking for.
Carrie Richardson:And on top of that, and then how do you determine whether or not it was when you saw them at asci last month, or if it's when you saw them at PAX eight this month, or perhaps you see them at IT Nation in October. And are you attributing the WIN to the first time you interact with that MSP or the last time?
Len DiCostanza:That's the whole battle because you really have a waterfall approach. I did a webinar, I got 600 MSPs there, and then that is why they probably came to us at an event and why they opened the email and why they visited the website. You just want to be part of the waterfall, and how many leads or conversions were touched by this webinar by that. So you you want to be a part of that waterfall. At least an activity wants to be a part of it.'cause then that means you'll do that activity again. Webinars are always fantastic. I think when we were acquired it was like a 960% ROI on webinars. Why? Because they're cost effective to produce. Now I think people a little burnt out. You maybe get some on demand stuff more, but I think, you just gotta back into a number that's gonna work for you based on your investment. Plus what you wanna achieve. I do the same thing with MSPs when I talk pricing, understand your costs because based on that, then you can determine your profit, whether you mark it up, whether you do value pricing and kind of the same thing. The same principle for me always applies what's and I think you brought it up, jostle on it, but whatever your cost is, that's gonna allow you to predict or target a number that's gonna be important to you.
Carrie Richardson:If you're selling something costs a hundred dollars per client to use versus a hundred dollars per seat to use, the way you're gonna determine your return on investment is going to be significantly different. You sign one client, you get 10,000 seats, you sign one client, you get one seat. How do you make back your ROI? Is it all branding? Does it matter if you're actually generating a return on investment or do you just have to splash your logo everywhere?
Len DiCostanza:Yeah, I think that's really where we're talking about. By the way, Carrie, I feel I have an 11 o'clock call now that I am missing.
Carrie Richardson:Alright, we don't want that happen, so thank you for joining us today, Len, and we will talk to you again soon.
Len DiCostanza:Alright, Carrie. Cheers.