Hallway Conference

Channel Veteran Len DiCostanzo Shares Tips on Virtual and Live Event Engagement

January 11, 2022 Carrie Simpson
Hallway Conference
Channel Veteran Len DiCostanzo Shares Tips on Virtual and Live Event Engagement
Show Notes Transcript

Len DiCostanzo was the host of the very first webinar I was ever invited to present on.  This was several years ago, but he gave me advice that has stuck to me to this day, and is still absolutely relevant:

"Don't ever tell the audience you're nervous, or that it's your first time presenting, or that you're hung over from the party the night before at the event.  Everyone here paid to see you speak today, both with their money and their time, and they came here to listen to an expert and you owe it to your audience to give them value. If you start your presentation by saying how nervous you are everyone will question their investment."

Len has built the channel programs for major channel players including Autotask (now Datto) - he successfully exited from his own managed IT services provider before moving into the vendor world. 

On Hallway Conference, Len shares the differences between presenting on stage and presenting on a virtual event.  Learn a little about his consulting practice, MSP Toolkit

Learn a little about Len!  If you've been in the channel more than a couple of years, you've surely met him in the hallway!

Learn more about Managed Sales Pros - Better Leads for MSPs at www.managedsalespros.com


Welcome to Hallway Conference with Carrie Simpson, the podcast for conference goers looking to make more of their annual business trip. Hear from experienced and successful professionals who step beyond the keynote and breakout rooms finding gold and ideas picked up in the hallway and perfected on the patio. She’s got secrets…and she’s telling. Here to start the show, your host, Carrie Simpson.


Carrie: Good afternoon, everybody. My name is Carrie Simpson and I am your host for Hallway Conference. Thank you so much for joining us today. With me today is a channel legend, Len DiCostanzo. I’ve been pronouncing your name wrong for 10 years. 

Len: No, you have not. You did it perfectly, Carrie. 

Carrie: But which one is it? 

Len: Len DiCostanzo.

Carrie: Len DiCostanz-o? 

Len: Yes. 

Carrie: Now, the circle of life, the first event that I ever was hosted on was a webinar that was done by Autotask that Len planned and he gave me some great advice at the beginning of that and I have given that advice to everybody that I’ve met that has done any sort of stage or webinar speech ever since and that was, do you remember?

Len: Man, I’ve given out a lot of tips, Carrie, but I remember breaking you in quite a bit. We looked at your slides, got yourself prepared, but, no, tell me. 

Carrie: You said don’t ever tell anybody it’s your first time presenting. Don’t ever tell anyone you’re tired. Don’t ever say that you’re hungover. Don’t say any of that. When you get on stage, people paid good money to see you talk, you’re the expert, that’s what they’re here for, and if you’re gonna say first thing, “I didn’t prepare well enough,” or, “I don’t know what I’m doing,” you’ve lost your audience at the very beginning. 

Len: Yeah.

Carrie: And it’s not respectful, right? Like they’ve come here to see an expert, they don’t know it’s your first time presenting so you have to give it everything you’ve got and you never tell anyone that you’re nervous or anxious or anything, because I remember saying on that, “Oh, I’m really anxious, I’ve never done this before,” and afterwards, you were like, “Don’t ever say that again.” I’m like, “Well, it won’t ever be my first time again though.”

Len: Yeah, well I think you did it on the webinar, Carrie, and then we actually brought you to a live event in Dallas and that was your first live presentation as well and I think we kind of followed from the webinar to the live event and that’s where I really think you gotta, you know, kinda be your best because now you’re in front of folks. And just - you’re the expert, you know, and you’re gonna teach some folks at least one nugget. And even if you don’t, let the audience give that one nugget and it looks like it came from you because there’s gonna be some good folks in the audience as well as some newbies taking everything you have so there’s a range of folks in there, just use your audience is another kind of thing I try to use now. 

Carrie: That’s one thing I’ve really kind of thought about as my career has grown is the number of people that are at an event for the first time, they’re investing in something for their business for the first time, right? They wrote that check to go to IT Nation, they wrote that check to go to Autotask Community Live or whatever event it is, there’s lots of people there who have never attended a professional industry event to learn from people on how to grow their business so it’s kind of cool that you get to be somebody’s first something all the time. 

Len: Yeah.

Carrie: Right? Like you’re gonna stand up on stage and this is gonna be the first time anyone’s heard like the concept of make more phone calls isn’t really that profound but if you’ve never thought about how much volume it would take to produce the results that you want, that could be a pretty disruptive conversation for your business. 

Len: Yeah. Well, definitely you have to, you know, know your audience, know who’s showing up at the event and, nowadays, as you know very well, Carrie, due to, you know, both of us being acquired, there’s ton of new folks show up that are actually at a pretty high level, meaning private equity firms looking to invest and acquire and find good people so you just — you never know when you go to an event who’s there, who’s watching, learning, trying to find out who’s who, and, you know, you just gotta be ready at an event. Big deal. 

Carrie: I’ve had a lot of really interesting opportunities from people that I met, you know, five, six years ago that we didn’t really talk after the event, we didn’t really connect and then walking around the event this past week, people were like, “Oh, yeah, I remember meeting you in whatever year and you did a seminar on,” probably lead generation for me, “and I was in the room there and our business was only a million in annual recurring then and now we’re at 5 million in annual recurring and we followed the steps that you taught us and thanks so much.” Like you never know whose business journey you get to be a part of so that’s really cool. 

Len: Yes, yes. Well, you know, no doubt. I know we’re gonna try to, you know, our hallway conversations about an event and as you know now that you’re a veteran, you go to all the events, you’re gonna run into those folks and that’s kind of the best feeling I ever get, somebody kind of coming up to me and sometimes I’ve literally gotten a hug, Carrie, a hug and a kiss going, “You changed my business back in,” whatever, because I’m a dinosaur like, you know, I’ve been here — I’m in my fourth decade, Carrie, doing this stuff. And guy will come up and say, “I never heard anyone talk about managed services ’til I heard you talk about recurring revenue before there was managed service,” and those are the best kinds of things. We actually helped someone’s business grow and, you know, make them have some success, feed their families, all that good stuff. 

Carrie: I don’t know how long Autotask webinars are archived for, but the pricing and bundling webinar that you did on a kind of quarterly basis for them, I’ve been pointing people to those for years. They were very impactful. They’re still relevant to this day, which is interesting. You know, some content will stale date very quickly but that particular presentation I think you could still stand up and give today. It would still be wildly relevant to the market. 

Len: Well, Carrie, it’s funny you say it, Mark Cattini, my former CEO, great man, actually took Autotask, you know, where we got to, which is two acquisitions, but he likened it to those songs, those one-hit wonder songs, you know? And he said, “I could live off of that forever,” and, you know, I’m, to this day, obviously, over the years, I’ve been in this industry a long time, have my own business so I really understand the model and what folks are trying to do but, you know, pricing is so important, so valuable or whatever and you just evolve it a little bit, you tweak it a little bit, but, at the end of the day, I often say, I’ve been doing this for almost four decades, it’s the same thing, except there’s new technology, more automation, more process, more people interested, more people looking at you and helping you but the business of being an MSP, not that much different and pricing follows it, every client, as I work with vendors now helping them build their MSP channel and every vendor has product sets and services and what they don’t understand is how to fit those products and services inside an MSP business model, inside the MSP’s core offerings or inside their portfolio, and that pricing and bundling does just that, so you could say, “Hey, MSP, here’s how you should price,” and now let’s stick in, you know, ConnectWise and cybersecurity stack and here’s how you price that into your bundle. Here’s how you grow and expand in your client base. So, it’s very relevant to this day, as you said, and every time I work with a vendor, I am typically doing a pricing and bundling session tied to their product set and positioning it inside the MSP. 

Carrie: I think partner enablement is essential for the success of vendors in the channel right now and there are some vendors who are doing a really good job of it. I know a lot of them have invested heavily in third party companies that are teaching the MSPs to do something, I know like for AppRiver, I do some sales masterclasses for their partners and, I mean, you’ve been doing this for how many decades now? You said four? 

Len: Yeah, partner enablement about two.

Carrie: Well, but you had to learn the MSP’s businesses inside and out before you could successfully assist with partner enablement. I think a lot of people come into the channel, and I know this because I work with vendors all the time who hire marketing agencies, for example, for outside the channel. I mean, not veteran channel companies but you get a new company, a new vendor coming into the channel, new software and a lot of those companies are founded by MSP business owners who developed a technology to help them solve a problem that they’re having and they realized that that problem is universal. You come into the channel and they try to sell their services the way that they sold their managed services offering and it’s just a completely different ballgame and they flounder a bit. So, it’s nice that there are resources, you know, like MSP Toolkit, where a vendor can come into the market and say like, “We need someone to help us figure this out,” because the traditional marketing agencies are failing the larger veteran channel companies right now and they have to come back to basics. They don’t understand how the MSP business works, especially that small MSP business, and you’d think that the people that owned that MSP who started the software company will be like, “Okay, well, I was a million-dollar MSP once, I had to buy a ton of stuff for my business, what resonated with me? What problems was I trying to solve?” Because the problems at the beginning are all the same.

Len: Well, they’re all the same throughout, essentially. That’s why peer groups have become so successful because everybody’s got the same issue. That’s what I’m saying. Business of being an MSP is pretty much the same if you kinda take a look at a framework, right? Like not everyone might do a UCaaS solution but the framework of building a UCaaS practice is the same for every MSP. So if you’re a vendor and you wanna get into an MSP, know how to help them build a practice, whether they outsource or like you were saying earlier, build it themselves, hire their own people, because you can outsource so much, maybe at some point you wanna bring it in house, you just gotta know how to do it. It’s funny you bring enabling up but I remember being a solution provider probably pre MSP because I sold my business 2001 and I would love when vendor channel reps would come in and go, “How can I help you?” I’m like, “How can you help me? You know, tell me what services I need to deliver? How long does it take to set up your stuff? How much money can I make?” Like that is the start of enablement is bringing them in and then showing them how to do it and that’s where pricing and bundling comes in, but every vendor I work with, the number one place I look is that enablement. And, typically, you’ll see technical enablement, you know? Getting the tech certified. Now, and certainly at Autotask when we built our partner program and I think every vendor now kinda gets it, always got it, but you gotta advance to a point. For example, everyone always gave marketing literature. I remember when we launched our Autotask partner program, we included a free marketing automation platform and I know some bigger vendors did that but I think it’s key to understand where the gaps are, how can you help your partners, and, you know, just enable them and a wide swath: technical, sales, marketing. In your case, how special is it? You know, business development, like talking to you right now, I just thought, “Gosh, my next vendor program, I better have a business development readiness checklist,” because it’s not just sales and marketing, that marketing comes in, you need, you know, what you do, you need that BDR calling down, you know, profiling and making sure they fit and where do they go next and what’s the next steps, where do they fit in terms of negotiation and bringing them in as a partner. So, you just gave me an idea there, Carrie.

Carrie: I am the anti-profile, like I don’t go in for the, well, we have to figure out who are — you know who your profile is when you’re doing outbound? Whoever picks up the goddamn phone. Like I don’t care how big they are, I don’t care how small, like the only person you’re going to be able to talk to is the person that picks up the phone. And there is a 0 percent chance that you’re gonna predict who answers the phone when you call in. So, you know, you’re like, “Well, they’re like in their 40s and they’re married and they golf and they do this and they…,” like, yeah, that’s every MSP in the channel pretty much so unless you’re gonna target like the four MSPs that are owned by women in the channel or some other, you know, niche group —

Len: Really narrow focus.

Carrie: Yeah, like the odds are you’re not going to be able to figure out right off the bat who your UCP is, especially as a new vendor, go in, try different buckets, see where the message resonates. When’s it good — who closes fastest? Is it the $5 million MSP or the $1 million MSP, you know? Is the buyer journey 365 days long or 35 days long? Nobody knows this coming into the market with their brand new product because they’ve sold it to a couple of their peers, for example, they’ve sold it to some friends, they’ve done a little bit of prospecting. I’m seeing a ton of software hitting the market right now from MSPs, big MSPs, successful. centrexIT just launched a new integrated software or integrated — they’re calling it an ITSM management platform, which I assume is a PSA but I don’t know yet, I only had, you know, I’ve read the press release but, you know, there was a big MSP that had a big problem, they were gonna change, I talked to them at the [inaudible] conference two years ago, the last conference before the world shut down. I sat down with Sean from centrexIT and he was like, “You know, we’re thinking about changing to service now but it’s, you know, X number of dollars to implement and I think we can build it ourselves. I think we can build something better. I don’t think we need to spend a million dollars to implement and a million dollars a year to use ConnectWise or ServiceNow. I think we can build our own.” I was like, “Okay.”

Len: Now they did it. 

Carrie: But they launched it yesterday so, God damn, good on them, and I’m excited to see what happens there. But like there’s lots of companies like that. There’s lots of opportunity for us, Len. We’re not old yet. We got lots of fight left in us. 

Len: Yeah. What was funny, you know, what’s interesting to me about what you just said is that partners now actually use those four letters, ITSM. That’s definitely something I’ve been, you know, looking at, talking about for many years and that’s IT service management. I mean, that’s really the framework, the best practice framework, you know, trying to get your MSP to really service your clients better, right? It’s an IT term that is now, you know, squarely one of the key frameworks an MSP has to follow, kind of like ITIL or any of the other best practice frameworks out there. 

Carrie: So they built this around the ITIL 4 framework. 

Len: Yeah, yeah. 

Carrie: So I think it’s gonna be an interesting year in the channel. I think there’s a ton more companies like that kicking their way in.

Len: Yeah.

Carrie: It’s gonna be fun to see if we can unseat some of the —

Len: Incumbent?

Carrie: — kings in the channel. 

Len: Yes. 

Carrie: I think the market’s right for some disruption. 

Len: You know, I think the market’s always right. That’s why, you know, I love when folks, you know, sometimes, even including me, it’s like, “Oh, gee, you missed that boat. Oh, you missed that boat.” You never miss the boat. You just gotta get on it. You just gotta figure it out and do it because there’s always room, you know? There’s always room for another CRM, doesn’t mean Salesforce cornered the market, make a lighter, tighter, easier CRM and you’ll get some users and get some momentum. So it’s really been good to see, like you said, you know, MSPs taking their wares to the market and, interestingly, Carrie, in my early days as a solution provider, I was a developer, I was a coder. I wrote so many applications, like I used to sit in front of my computer and write software. And there was no internet. I moved more to infrastructure.

Carrie: I remember those days. 

Len: And, in fact, I remember writing a time and billing application to track my time, my tickets in my business, and I had a few people using it. And this company, ConnectWise, was also doing the same. They were an MSP and people were starting to use it. Well, I got acquired in 2001 and they acquired my software, my business and kinda didn’t let us focus on continuing with the software. They didn’t see an opportunity there. And we all know what happened with ConnectWise and the Autotasks of the world, you know, 20 years later, they’re a $1.3 billion company. So, that boat I missed. I got on a few other boats.

Carrie: What are the other boats? So, if you could like get into your time machine and, you know, go back 10 years, what company do you wish you had joined? Like if you had had the opportunity and been invited and the money was right, where would you have gone? 

Len: Well, I mean, it might sound, you know, cliché or whatever but I ended up in the perfect spot. I mean, I had been kind of — it always seemed like I was a little bit ahead, meaning I was always doing services. I never sold product for 10 years in my business, it was all about writing software, understand the business process, automating it with software back on single floppy, double floppy, one hard drive, then a network and all this stuff so I’ve seen this whole thing. You know, when I ran into, you know, my first client after I sold my business was Kaseya and I, you know, kind of got more deeply involved with RMM and then when I ran into Autotask, it was just, “This is me,” you know? I’ve been an MSP, a solution provider, and I had a piece of software that, you know, kind of integrated all key business processes into one solution, you don’t have to go buy all different stuff, everything was in one place, which is what I was trying to do myself. And, you know, it was a perfect spot where I got to be in front of MSPs and kind of share my experience and tie it to the solution, wa la, you know, here I am today and I couldn’t have been in a better place. We were acquired twice, 2013 and then 2017, merged with Datto. Great ride. So, I think if I were to look back, I would have just — I would have hoped Mark Cattini would have waited three more years to sell because, in three more years, ConnectWise was bought for $1.3 billion. We weren’t quite bought for that amount but, you know, valuations just jumped up so the only thing I would change about where I was was the timing of our sale. So, it was a wonderful run. I’m still living and enjoying it to this day. 

Carrie: Well, I mean, you guys threw a hell of an event too. Autotask Community Live was always a fun time. Always well timed, well produced, and I liked how Autotask always paid attention not only to the attendees but what would be good for the vendors, right? We didn’t have to sit in the solution hall for eight full hours while people wandered in and out one at a time. Like as a small vendor coming into the space, that show was really great for us because there was only two of us at the time that could come and work a booth and we couldn’t both stand there for eight hours a day, we still had a business to run, so like for a smaller vendor, those events were fantastic. We got a ton of ROI at them. So let’s talk a little bit about how you put together an event that’s going to be attractive to both attendees and sponsors. Where do you start? 

Len: Yes. Where do you start? Well, man, first off, you know, I think most every vendor in the channel doesn’t really have a big enough team to put on a huge event, like I know, we just did a ConnectWise IT Nation, much like Community Live, DattoCon, all these events, you have people with real jobs, right? Like you just said, you know, you’re at a booth but you got a business to run. Well, there are people who run marketing and have to drive leads. Oh, now we gotta plan an event. So, number one is really just organization and structure and who’s your point and making sure you have your internal folks, you know, ready to go and, hopefully, your experience has given you a nice little process or, like my buddy Rob over Datto, you know, you observe how another vendor does it and the first DattoCon, you know, I remember walking in and going, “Hey, Rob, this looks strangely familiar.” You’ve been to so many Autotask events, he’s like, “Why mess with a good thing?” So, you know, I think you just gotta realize people have real jobs and you gotta kinda organize internally and then really talk to your partners. What do they wanna hear, you know? What do they want to see so you have a great agenda? That’s obviously number one. You can’t have a bad agenda. And one of the things, one of our biggest ROIs was attendees who came to our event that drove adoption in their companies of Autotask, north of 60 percent. You might see partners just using ticketing, but we had a whole track. How do you take CRM and quoting and project management and roll it into tickets and your billing and your contracts and, you know, great agendas lead to results or ROI that you’re looking for, which for us at the time early on was an education of that was adoption of your offering. And then, over time, we realized, wow, we have a thousand people coming next year, what do we do? You set up not only an agenda but now you’ve got your large partners who wanna be treated differently. You got, you know, smaller partners that you know you have to treat differently. Like you mentioned earlier, smaller guys, you know, there’s a certain way they operate. Everybody’s doing everything. So, the agendas right, look at your audience, what kind of segments are attending. Our biggest probably development project was our UI, our new UI dashboard interface, and I remember that event where we brought in groups of partners to help us design the darn thing and you just started taking your event over time and you just have to make sure you’re hitting key groups. (A), you want to grow your event, you don’t just want people who want to learn your product, like they want to go meet their peers, they wanna meet Carrie Simpson from any vendor from any company, right? That they wanna go and see. Usually, they wanna see their vendors who they work with there so they could chat with them. So you have to have a pretty open door in terms of competition. Now, at Autotask, we never had ConnectWise and ConnectWise never had us but we always tried and, you know, I think, in today’s world, that’s even more true is like everybody’s got similar products. So, you know, agenda, you gotta, you know, hit that wide swath of attendees, you gotta look at your vendor sponsors that you’re bringing in. That’s a huge ROI to help defray the cost. You’re gonna not let certain folks come? The word gets around. “Ah, the heck with that event.” So internal organization, look at your agenda, make it broad enough to hit a wide swath of your partners, focus on your vendors, that’s kinda one of my key roles was bringing vendors like you in and, you know, there’s probably a couple of key points, at least for a live event. And I know we just did IT Nation, I thought they did a heck of a job, especially coming out of COVID and, you know, it’s been quite a while but, you know, top notch event in my opinion, looked very professional, very well organized. And I just finished some work there at ConnectWise and I know they are running a mile a minute just in the business itself, integrating, you know, more than five acquisitions over the last couple of years. And so a lot of work there and to know that they could put an event on like that with a team that has real jobs in addition to putting that event on, you know, I just thought it was tremendous. A lot of hallway conversations, Carrie.

Carrie: Yeah, I like that event. I think of all the IT Nations that I have attended, either, you know, just as a random sitting in the bar because I couldn’t afford the sponsorship or because I didn’t want to afford the sponsorship. Actually ConnectWise was really good to me when I started my business, because I worked with so many partners that used ConnectWise and that’s what we did all of our outbound calling in previously, I was like, look, you guys, I can go buy a seat at ConnectWise and whatever, right? But I’ve got 10 partners that use it and I need to understand it better. So if you would be so kind as to allow me to come to your event, I’m coming to sit-in sessions because I don’t know how to use ConnectWise and your partners don’t either, right? They don’t use it for this. They don’t use it for sales and marketing. They use it for managing their tickets and they’re trying to use it as a CRM system, there’s gotta be some workarounds so we can make this go better. So, before going to a ConnectWise event, we maybe were able to make eight calls an hour in ConnectWise, because of the way that we had to move through the data, right? Okay, click on this. No, a new note, not — so people get lazy in ConnectWise. One of the things that I don’t like about ConnectWise is it lets people be super lazy, or at least back when we used it, the way that you could take notes in ConnectWise was you had the subject line and then you had the content of the note but you could just go and keep adding to that note so if you add a lazy sales rep, instead of starting a new instance the way you’d open a new ticket, they’d just go back to the old ticket or note and they’d just put their notes in so you never got a really accurate overview of how many times you had to touch the lead. You couldn’t pull a report because you pull the report, it would only show one instance of that interaction because they just log their notes in the same spot. It’s like, okay, we can’t do it like that, we have to figure out a way where we can show the MSP how many calls it takes to get to that actual conversation and, you know, what changes along the way. So how do we show an MSP in ConnectWise the journey from the minute the lead hits their system until they off cord, like realistically ConnectWise should be able to do that. But try and figure out how to make outbound calls efficient in ConnectWise, it was like banging your head against the wall and then throw the cloud application in there, which 10 years ago was abysmally slow compared to the on-premise version, you just got a caller sitting there waiting for everything to load and then clicking the dial in phone number and you literally were able to go from eight calls an hour to 17 just by attending one ConnectWise event and sitting in sessions. So, I mean, they were very good to me to allow me to do that. But they only allowed me to do that once. Next year, I had put my money on the table. And it was — like I remember like putting that on my Visa and just hoping we were still in business by the time IT Nation arrived because you have to pay for it way, way early if you want any sort of booth placement, any sort of anything. Like there should be a company that tells new vendors how to sponsor events properly because we had no idea. It’s like, okay, there’s 2,000 people coming to ConnectWise so I guess we’re gonna need 2,000 somethings to give away and Tracie was like, “Yeah, okay. Like what are we gonna do?” Oh, let’s give away coffee. That was like back when we were doing our Glengarry Glen Ross thing. So, I had 2,000 pounds of coffee in my hotel room at IT Nation.

Len: Yeah, no, I remember the days. Well, the nice thing is you learned as you went and that’s the value of like the ConnectWise peer groups, all the peer groups that are out there and all the training organizations you had mentioned earlier, you know? People have done this before, it’s not rocket science, you know? So, go find the folks that have done it and I think that’s key. And as MSP Toolkit, my own kind of consulting right now, that’s really what it’s about, just taking, like you, your years of experience and cutting people’s time short to learn and, heck, I did some work with ConnectWise over the last year to help them build out their partner program for cybersecurity. So, everybody could use a little help. Number one, they all got real jobs. Number two, you know, they have people that have come and gone so they lose a little institutional memory there. And if you could bring in someone that knows what’s up, it’s gonna take that learning curve and you know, slice it, you know, way more than half. And then to your point, they gotta then learn and implement and evolve it and make it their own and away they go. So, I remember those early days, Carrie.

Carrie: God, I didn’t know that you needed to do site visit — like so when we started spending more on sponsorships, I had no idea that you had to go do site visits to figure out what stuff, like I just assumed like the person hosting the event would take care of it. And that is not the case. So, you know, I wish I’d invested some money and this is probably like the key takeaway for me, and if, you know, for the MSPs or the new vendors watching, invest a little bit of money at the very beginning talking to some experts that can help you avoid the biggest missteps. Like for us, I could have saved a ton of money not buying 2,000 pounds of coffee, I should have bought like 100 pounds of coffee, right? And we had to ship them from New Orleans because we had them custom made and like we did a whole thing and I ended up sending, I wanna say I sent like 500 pounds of coffee home with Datto because they were the only people that had like enough whatever space, right? With the company that ships home all the shit. I was like, “All right, who can who can take home 500 pounds of coffee?” I’m not gonna throw it away and I’m not gonna pay to ship it home. What am I gonna do? It’s gonna go bad. I think they had coffee in their offices for like two years after that.

Len: Yeah, well, you know, I mean, those tchotchkes, I guess, they call ’em.

Carrie: But why are people so hesitant to invest in things like that? Like we were too, right? Like, well, what do we need to learn? How hard could it be to sponsor an event? Well, it turns out pretty hard.

Len: You know, I think one of the things we chatted about was, you know, prefab booths, things like that, like I used to not necessarily be for that, you know? But I think when a vendor or whoever’s putting on an event, when you think about the vendors coming, especially like the smaller ones or certain levels of sponsorship, having things kind of look and feel the same and then letting the vendor kind of customize inside the booth, like have your name, everybody looking the same, and then the big guys come and drop their 80 grand and build a house, you know? Just the channel partners and, you know, LogMeIn, doing some work with LogMeIn, they won the best booth of channel partners but it was a building, it literally was, you know, put together by engineers and shipped and a bar and a lounge and an office and this and, you know, so some vendors do their homework, they’ve been doing it a while, others, you know, “Hey, I’m only gonna invest, you know, 20 grand, 30 grand 10 grand,” make it easy for them, give them the lay of the land. That’s why I thought we always tried to do is, you know, what are our vendors gonna experience? And we did our best. Obviously, you’re gonna have, you know, the far corner booth for the last five sponsors, unfortunately, and —

Carrie: Dude, I got that booth even if I was the first five sponsors. Always. Like one of the reasons I stopped sponsoring IT Nation is there was, like the prospectus came out and I was like, “Here is my money, take my money,” and I still got like the world’s shittiest booth and I’m like, “I’m done,” like I don’t even know, I can’t buy this thing any faster and I can’t spend any more money. Like I want a good booth one day, please.

Len: Yeah, well, I think working with you, Carrie, too, and you learn, even if you’ve done it, you know, it’s like, okay, I guess let’s put a bar down by Carrie’s booth, you know, and everybody will do the pub crawl by Carrie’s booth. So, you know, again, if you’re thinking about the vendors and why they’re there, what’s their ROI go? Hey, they gotta get leads, they gotta find partners. And if they’re a sponsor and they don’t get those leads, they won’t come back or they’ll question it. So you always have to be thinking at these events, like is there gonna be enough traffic and, you know, we started to do things like, you know, put instead of being the sponsor hall and go in the sponsor hall, while lunch is going on in another spot, make sure lunch is spread out throughout the sponsor hall so people gotta go. They have to be there. And, you know, you kinda learn these things as you go but the bottom line is, sponsors are the key to any event, because without a sponsor list, you’re not gonna have an event. The events are not trivial. I can’t even — I mean, I could venture a guess because I know probably our last event, 2017, before we merged Datto, I think we were a couple million bucks to run Autotask Community Live. We had about 1,200 maybe or so MSPs, another couple hundred vendors, you know, attendees, things like that, and they’re not cheap. So you better take care of your vendor sponsors, and as an MSP, you need to understand that too because if you don’t visit booths, then that event might not be there too long, you know? Or that sponsor that you wanna see won’t show up because no one visited them. So I think attendees have it on themselves to not stay in their room, to not, you know, go hang out by the pool, you know? You gotta visit your sponsors and it was totally a line item, I’d be up, you know, hosting the event, first thing I’d say and the last thing, visit your vendor sponsors, you know? They make the event happen so real important. 

Carrie: So, as an attendee, so when you’re gonna sponsor an event, not organize an event, one of the things that I’ve really kind of frowned upon in the last few years is how the lead generation teams are incentivized, “Just get business cards, just get as many business cards as you can,” you know? Like that’s the — like, “Go stand in the middle of the hallway and meet people.” You know who’s really good at that? You remember Jan from eFolder? 

Len: Yeah.

Carrie: I once watched Jan from eFolder work a channel partner’s room during the award ceremony and she just went to every table and she bullied everybody at that table into voting for — maybe she wasn’t with eFolder at the time, I can’t remember who she — because she’s bounced around a bit, but like she’s like a channel maven at this point. You don’t say no to Jan. She’s like, she comes over to the table, she just sits down, she’s like, “Open up the app, vote for us. Open up the app, vote for us. Open up the app, vote for us.” Everybody at the table, what? You’re gonna say no to Jan?

Len: Yes.

Carrie: No, you’re not. So, she was awesome at that. But are people being incentivized for the wrong types of behavior? At IT Nation, I didn’t visit a ton of vendors, right? Like I’m a vendor so I don’t wanna go waste their time when they could be talking to prospects, I’ll find them at the bar later or I’ll grab a card and I’ll call them after the event. But how do you encourage people to collect leads in a way where they’re not gonna bother everybody that’s not interested in talking to them? So I went to an event before IT Nation, so IT Nation doesn’t give you the list when you sponsor, right? You don’t get the full list of everyone that sponsored, you only get the people that come to your booth, which I like because if I went to your booth and I interacted with you and I gave you a card or I let you scan my tag, I want you to interact with me. If I didn’t, I don’t. So, part of the challenge I’m seeing is so I went to an event and now that I’m doing some work with MSP Core out of Canada, I work for an MSP now so I can go as an attendee without, you know, being a schmuck, and the number of people that emailed me after that event saying, “Hey, thanks for stopping by our booth,” I didn’t stop at anybody’s booth, I was at the pool. And I was — no, I wasn’t at the pool, it was in New Jersey, it was cold, but I mean, the only thing that I buy for MSP Core is other MSPs, right? That’s the only thing I do. I don’t choose software for them. I’m gonna choose the new RMM for, you know, a $35 million MSP? No. Like I don’t even know how to use one. Stop emailing me. 

Len: Yeah. 

Carrie: So, how do we incentivize — so if I think about like the way that my inbox got slammed after that and I thought, “No wonder MSPs hate us,” I’ve got like 27 emails today, none from people I wanted to talk to. So, how do you incentivize the vendors to engage differently or how do you incentivize the people working the event to not just like throw everybody into the fishbowl and then like bother them for the next five years?

Len: Yeah, that’s a wonderful question. I think, you know, touching both sides, but, I mean, you know, I did all the events at Autotask, we had a whole event kind of team and process and you always try to train your people how to do it and it’s always those conversations that bubble everything up. So, what we tried to do, maybe silly, Carrie, but, you know, now, of course, you have an iPad but we actually had paper forms with key questions, and based on those questions, as you’re dialoguing, “No, I’m not interested,” is a pretty important, you know, button to tag and you can even send an email saying, “Hey, I know you’re not interested but kind of remember us and here’s a couple of things coming up,” and then, hopefully, your connected lead processing engine, in your Marketos or whatever you’re using to market, you can take the info you gathered and make sure it’s in there and then we, you know, as automation took hold, we took that form, put it on an iPad. Now you can have, you know, you kind of rep, “So what do you do? What do you do for our member?” You obviously gotta — I’ll give you an example, one at IT Nations —

Carrie: And what do you do, right? Like if you have no buying authority for the RMM or for the, you know, like there is no reason for you to keep talking to them if, you know, like, “Oh, I’m the wife of so and so, that’s why I’m here.”

Len: Yeah, but on your form, are you the decision maker? 

Carrie: Oh, so they’re filling out the form?

Len: Well, you’re talking to them, like you’re talking to this person who has paid to come to the event. They may be the admin responsible for billing. They can’t pick an RMM. They may not even know what an RMM is. But they may know the tech who has their hands on the RMM. So your team at the event just has to be real educated as to how to be at this event. Now, you know, it’s interesting point because I’m working with a vendor-client right now and they were at IT Nation and I was hanging at the booth and trying to kinda observe, it’s maybe the second MSP event they’ve ever been to, and, at one point, I’m like, “Guys, you cannot wait for a partner to come in your booth.” To your point, they may not be coming because they’re not interested but they may not be coming because your company name doesn’t mean anything if they’ve never heard of you. And I said, “Here, watch this, guys,” and I went back to my roots, Carrie, and I, you know, some MSP walking by like, “What are you doing for blah, blah, blah?” Um, well, not really, haven’t really thought about it. Well, how about this? Come on in, blah, blah, blah, talk to, you know, they’re managing 10,000 users, okay? The solution this vendor is bringing to market monetizes end users. You are going to let that person walked by because you were sitting there hoping they came in. So, you do have to be a little, I don’t wanna say aggressive, but they know why you’re there, they try to not go to you, especially if they don’t know you. If you’re their vendor, they’ll come right up. Yeah, use you and then you talk with them but you gotta be active. You gotta, wherever you go, you gotta ask the questions and make sure you gather, not a business card, make sure you gathering the right information, you could pop it into your lead processing engine, your marketing machine, and, hopefully, act on the deal again and that’s what we were trying to do and, you know, we kinda went down the path of paper form then you got to enter them and it would be the rep who went that entered them and they would get those leads because it was typically in their territory. But, bottom line, collect the right info, make sure it’s entered into your systems properly, and that your systems are automated and can handle that because, I’m telling you too, I’m getting, you know, “Hey, look, I’m a consultant. I’m not interested in using your product but I need to know about it so I can share it with my clients.” Boy, am I getting so many emails, you know, matter of fact, I’m with Autotask for 12 years, then I’m with Datto. I get data reps trying to sell me Autotask or, you know, the CMSP toolkit. So —

Carrie: Don’t you know who I am?

Len: It’s like I used to kind of say that, I’m like, oh, no, you know, I’m not really a prospect, I’m a consultant, like I just try to — but they don’t gather that info, you know? They just wanna scan your badge, have a lead count, they did their job. But if you scan a badge, you’re not gathering the right info. So, we didn’t even ever get the kind of — you go to an event, they’ll give you a scanner to collect leads. It’s a nice, easy way to do it but only if the people at the booth scanned the badge of the person who’s really interested. But if you’re gonna scan a badge and you can’t go, “This person said call that person,” then you’ve missed half the boat. So, I tend to push one-on-one conversations, gather the right information, make sure it’s put into your lead engine, and you gotta deal with it in an automated way. Otherwise, it’s just not gonna happen.

Carrie: Small vendors, that was just always brutal, right? You worked the booth and the booth closes at nine and then the party’s until midnight and then the other party’s until four and then I’m like connecting with people on LinkedIn so that I don’t forget, we’ve got like the 25 cards we got at the booth, like, all right, we can’t — gotta get these in like right now while we’re thinking about it or they’re going to the bottom of the handbag or they’re gonna get thrown in the hotel garbage because somebody cleans the room, right? There are so many things that can happen between you getting that card and you talking to that person. Like, for us, it was always like here’s the thing that we do at the event so we got, I mean, as we grew and we could afford to do more, we did more, but we had a card scanner, it went right into the CRM, we put our notes in, we wrote them, old school.

Len: What I gotta tell you is even if you don’t have a connected lead processing, you don’t have a form, you gotta at least try to write on your cards, “What the heck? What’s this lead about?” Because you’re right, Carrie, so much happens. So I think one of the keys to sponsoring an event as a vendor is to know why you’re going, right? Are you going there to just get your name out so you don’t care if you get any leads? I don’t think so. But it’s definitely part of it, right? You wanna get out there. But it’s about finding somebody, some MSP that’s gonna either use your product, if that’s the way it’s intended to be used inside the business, or to sell with or through the partner and, you know, we talked about profiling, it’s like you just have to know, “Do you have clients that you service and that you can sell and deploy my software? That’s good enough for me. I don’t care if you have 200 or 10,000. I’ll treat you different, but I’m okay having a long tail as long as I have a lot of automation in my sign-up and enablement and, you know, I don’t care what size you are, just are you kinda in that category that’s gonna either consume or resell my stuff? I got a good lead, let me get it in my system and start chatting with you, you know? So, I think you just have to know why you’re there and it’s to collect leads and you better have a good process to do that.

Carrie: How do you attribute ROI from event sponsorship? Is it the first event you meet them at or the last event you attend before they buy something from you? Right? If you’re gonna meet some — like so our first IT Nation event, fabulous, absolutely able to measure return on investment, we made a 300 percent return on our first IT Nation investment and I, you know, didn’t really know how to do that math when we first started our business but, you know, now I can so I can go — and we’ve tracked all of that for years, right? So we have people that we’ve seen at IT Nation every year for five years that bought from us on year six, so do I attribute the revenue to IT Nation 2016 or whenever we met them or do I attribute it to IT Nation 2021?

Len: That’s pretty much the age-old question, Carrie, and you might have, you know, better answers than me. All I know is we call it waterfall, right? I mean, basically, every touch and then you count how many touches, not necessarily what event led to it, although most folks measure the last touch as the reason the sale happened. But you and I both know that’s not the case. That first event where they met Carrie Simpson or Len and they started to like the company because they liked you and then they went back home and watched a webinar, then they got a call from somebody following up the lead and they spoke to that person and then they continued to kinda touch, every touch is important, usually that last touch is attributed to it. To me, that first touch is pretty darn important. But you just gotta have a — you know, we used to try to put a percentage kinda to it, you know, based on the touch but clearly for us when we were acquired, our webinars, particularly like a 960 ROI, on a 960 percent ROI, the lowest cost, best lead gen engine in the company, you just got to have ways to drag people in because once they’re in, in my opinion, now you can talk to them. And if you don’t mess up, one day they’ll buy. And if you want to go, hey, the last touch has been this for 70 percent, well, then maybe your last touch is pretty good. But that first touch is so important and every touch in between. So, you know, I don’t know. I really — I’m not a marketer. All I know is every touch is important.

Carrie: We’re for all marketers. We’re all marketers, don’t say that. 

Len: Yeah.

Carrie: Everyone’s in marketing. Everyone’s in sales. 

Len: Yeah, I agree with you. I agree with you. I guess I’m not a professional marketer, I don’t know. But I’ve done enough marketing in my day to certainly know every touch is important and from the first to the last and you just have to have really good engagement along the journey. That buyer journey is obviously so important. You wanna go, “First we’ll do this, that we’ll do that, then we’ll do that.” But —

Carrie: The buyer’s like, “No.

Len: Yeah, no, that’s not the way I buy, you know?

Carrie: Take me off your stupid mailing list. I don’t wanna be on it, you know? I’ll come to your webinars but don’t send me stuff after.

Len: There you go. It’s like, “Let me decide,” but, you know, it’s clear that a lot of weight is put on that last touch but you just have to weigh everything and attribute some percent of that revenue to the touches that you had, in my opinion, because I used to fight like mad. I brought them in on a webinar, that should be tied to the webinar. No, no, no. The call-out by the rep is what got them in. Okay, maybe it was a good demo, but they would have not heard of it. So, every touch is important, Carrie. 

Carrie: Yeah, I think so. 

Len: What do you look at as the most important?

Carrie: I don’t, which I think is terrible. It’s terrible to admit that but, I mean, we weren’t mature enough as a business when we were sponsoring trade shows to understand how to measure whether or not it worked or not. We just kept going and like prayed, like that was our whole marketing plan. But we do a lot of cold calling, right? So we were able to say, like even now, people will — I’ll get inbound leads now, it’s like, “Oh, we met you in IT Nation four years ago or three years ago.” Really? Three years ago? Who was keynoting because that’s the only one I can remember what happened at that IT Nation? Was that the Simon Sinek one or was it the one where everybody cried? It was that like the Prophet. I love that everybody hated that keynote. I love that keynote. But when people say that, like when they say like where they remember us from, like that’s great because now we can say, okay, well, we can obviously attribute this revenue to that. But we also produced two years of content in between meeting you and you buying that they went and consumed so it’s all important but, as a smaller vendor, how much money and time can you spend trying to figure that out at the beginning? Like for us, it was like, well, everybody goes to IT Nation so I guess we’ll go there and then, well, Autotask, now we know about that, so I guess we’re gonna go there too, you know? And then now where do we go? Like what else should we do?

Len: You gotta go to all the watering holes, unfortunately. I think that’s the other fact of life here.

Carrie: Oh, it’s exhausting though. Like how nice was — like, okay, like real talk here. The pandemic for me was ultimately like I am so goddamn bored and I miss seeing like my — I saw the people in the channel more than I saw my family the year before the pandemic hit and then the year the pandemic, it was just, well, it’s nice that I don’t have to be in a different city every day for the next 100 days in a row but I also really missed the relationships that I formed over the last eight years because I, you know, I saw you pretty often and Tracie and I were both like, “Okay, when do we get back? When do we get to an appointment?” and now I’m back on the road, I’m like, no, I don’t think this is the life for me anymore. Like having a couple of stable years where I didn’t have to be somewhere different. I don’t know if I’m going back to road warrior life. I might go to the big events only from here on in.

Len: No, that’s interesting you say it, but, yes, I’ve been remote for many years pre-pandemic when I left unceremoniously from Datto after our merger, I joined a company based out in New Zealand, my team was in New Zealand, so I was on Teams 2018, ’19. And then the pandemic hit and it was, to me, no different. But, you know, I put 150,000 miles a year on my United, you know, account, and then all of a sudden, nothing. And the nice thing is, is through the pandemic, I started picking up some clients and I started traveling to client locations, which is a little different than going to an event. But, definitely, I got a little bit of a breather and — but when we went out like IT Nation, I did channel partners three weeks ago, first week in November, Bobby Dimarzo and the team over there, Kelly Dan’s gonna do a great job at channel partners and you just — it was great, seeing folks again and kind of being out and I think those interactions really help you, whether you’re a vendor or an MSP, just like anything, it’s like this hallway chat we’re having, you know? You just pick up a lot and there’s so much value to it. I mean, I would say during the pandemic, the biggest webinar I did, I maybe had 500 people on it and I went out and bought a nice big screen and I could see everybody so it was kinda like I’m here presenting and I could see people but you couldn’t chat with them after. You couldn’t, you know, run into them in the hall and have them go, “Hey, I liked your presentation and here’s,” you know, blah, blah, blah, or, “What about this? What about that?” which gives you feedback to go evolve your own self, evolve your presentation, so, you know, remote is great, it’s a whole new kind of approach for most people. In fact, most people tell you — I mean, I was doing Citrix meta frame in like early 90s, remote access was key. I had construction clients with groups and projects all over the place. I had to connect them, right? So it’s just way better to be in person. You can follow up very easy and it was good to actually be back on the road. The unfortunate thing for this IT Nation event though, Carrie, is I kinda felt like, I don’t know how you say, the elder statesman. I mean, I used to be the young guy in the channel, you know? Now you got young guys and these guys coming up, “Oh, I remember when,” or, “I saw you here and haven’t seen you in so long.” It’s like, oh, crap, I am now the oldest guy in the channel.

Carrie: It doesn’t feel like it’s been that long like when I think about it, my first IT Nation was probably 2013, I didn’t have my own business at that time, really. I came when we were trying to figure out managed services for a call center that I was helping another person build and I saw this opportunity in the market and I went to the event just trying to figure out what the hell managed services was at the time.

Len: Yeah, well.

Carrie: Now, it’s, what? 2021. I’m a few years older, several years wiser —

Len: Wiser.

Carrie: Wiser.

Len: You’re the queen of the channel now and everybody knows —

Carrie: No, Tracie is the queen of the channel —

Len: Oh, Tracie’s the queen? You know, you paved the way, Carrie —

Carrie: I’m like the head of state or whatever. Tracie’s the president of the channel, I guess I could be the queen. It’s just a name, in title only.

Len: That was a good thing you always did. You know, you put your people first, front and center. You got them out there and you tried to stay in the background, Carrie, but it was really hard for you to do that. 

Carrie: Well, I do like glitter. 

Len: Yeah. You like to be out front.

Carrie: I like to have a good time too so the channel was — I mean, I was so glad I quit drinking years before I even discovered the channel. I think channel would have killed me. I don’t know how people do it. Like Tracie and I had to divide the days. I do the morning shift, I go to the coffee, like back when we were small vendor, like anytime there was a round table anywhere, I’m at it, like, “Here’s my business card. Hi, I’m Carrie, we do lead generation.” Like whether I’m sponsoring or not, I’m working those tables every minute I get. I’m at every break. I’m at every breakfast. Now I’m like, “We’re gonna go to the keynote. Do I really have to go to breakfast today?” But I had to — like now that I’m starting a new consulting company, I’m like, “Okay, we’re right back in it,” because Ian, my husband, Ian and I are starting this consulting business and we go and walk around the little IT Nation event, he’s like, “Yeah, you wanna leave?” And I was like no, you can’t leave, like welcome to being a vendor because he’s been in MSP for a lot of years now and I was like, no, no, the day’s just starting, we’re not — the vendors don’t even start partying until four. So, you know, get your pants on, let’s go —

Len: Well, now, sometimes ’til seven, actually at four or five because the sponsor hall opens and then you get on there.

Carrie: You gotta go home and at least put a clean suit on.

Len: I mean, I think you just kind of hit on another valuable tip there, Carrie, is, you know, always be working, you know? It’s not always closing, you know? You gotta sit at the tables, you gotta go to the breakfast, the lunch, and, as a vendor, if you want solid ROI, you better send a team there that isn’t looking for the sponsor hall to close so they can —

Carrie: So they can go drink.

Len: Well, go drink or leave the event, go to their room, like one of the things that was always tough, you want your sales team there but if you’re gonna put your sales team at an event, realize they’re gonna go to their room and sell. So you gotta kinda have a really fine mix at an event of people whose job is to be at the event and do exactly what you said, participate, because you realize there’s gonna be some folks that actually have to go do their real job. A sales rep, month end, going to an event is the worst that you could possibly put a sales rep in that position but you gotta work the event, like you said, don’t stop, never stops, you know? I remember, you know, Autotask Community Live and the host and like, you know, all these folks that are front and center, like, you know, you got Rob doing his DattoCon, you’re always on. You have to be on all the time. You have to have a certain level of energy to do this job and be everywhere. That’s key. Give your card out.

Carrie: Well, and you can’t be a Rob. Actually, Rob Rae gave me a really great piece of advice as well back in the day, besides like, oh, like somebody come up to the table and I was like, I was shitty to them, right? Like I don’t like them. I think they’re a charlatan. I don’t like this person, right? Like I have no respect for them. I think they muddy the water in my space, like I think — I just don’t like them at all. And Rob’s like, “Carrie, you have no idea whose ass you’re gonna have to kiss in five years. You can’t be shitty to people at events, like you can’t be rude to anyone because, one day, that guy,” and he told me a story about, you know, somebody that he didn’t particularly care for once who was now in a leadership position at a different company that he now had to do business with because he wasn’t at level platforms anymore, now he was the channel chief at Datto and this was a big Datto partner and now he’s in a place where, you know, good thing he wasn’t, like even though he didn’t care for him, good thing he wasn’t shitty to him because, you know, now they have to work together and it’s like you don’t know who you’re going to have to work for in five years and you don’t know you’re gonna have to work with in five years so you can’t walk around events just like you’re better than everyone. 

Len: Oh, yeah.

Carrie: It’s like you’re not better than anyone and I was like, okay, but I am better than that person. 

Len: Yeah, yeah. It’s funny you say it, you know, for those that maybe don’t know or remember Autotask now, maybe there’s some newbies, but, you know, Autotask and ConnectWise, you know, top competitors. We were — every RMM competed, the PSAs competed, and my friend Tony Thomas, industry friend, was at ConnectWise and he would always ring me up every year. “Hey, Len, I gotta come to Autotask Community Live.” I’m like, “Tony, I can’t have you come in,” and we started to have fun with it. And fast forward, there I am working with ConnectWise. Who am I working with? Tony Thomas. So, you know, you just have to be a professional.

Carrie: Channel’s too small. The channel is too small. 

Len: You have to be a professional and, you know, Tony was a great professional himself and we dealt with it great and if we ever had a problem with integrations, I call him, he’d call me so, you know, top competitors, you still have to respect each other and, you know, I was in Autotask 12 years so it would be funny, I’d be sitting in a ConnectWise meeting and you can literally see some of the ConnectWise, you know, elder statesman like looking at me going, “You’re that guy,” you know? “You’re that guy at Autotask that made me have to do this, that made me have to do that,” but it was in a fun, good way so you just have to really embrace it. And one other quick story is I remember, much like you, there was this one MSP that I just didn’t get, right? It just always seemed to be hanging around and, I don’t know, we sometimes get a feel for — they just wanna hang out and get drinks or they wanna hang out and go eat or something like that and I just remember one day being at an event and there this guy was again, but, you know, you’re always nice and professional and just turned out he was one of the more interesting guys when I finally started to get to know him and he ended up becoming like one of the spokespeople I used to call on because he was just a really smart, well-connected kind of person who just didn’t come across as dynamic, outgoing, whatever, but he was and, you know, I love finding that out. That’s why events are great.

Carrie: That happened to me at one of the bus tour events that were put on this year. They did like the MSP initiative, we went like we’d go city to city —

Len: Yeah.

Carrie: — and we went to the Michigan one, which was about an hour away from the house, so it was nice to get out, see everyone. There was this guy, like awkward, so awkward, and not really comfortable approaching groups, like maybe he was a new business owner, like nobody was talking to this guy. He was standing by himself at a table and he must have like stood at that table by himself for 30 minutes and then he walked over and he got some food and he went back to his table. I wasn’t hungry but I went and got food and I went to the table and I’m like this poor — like there’s only 20 of us at the event and here’s like guy 21 and nobody’s — like not one vendor, nobody’s introduced themselves, he’s just like — and this guy’s running a million-dollar MSP. He got one employee. How much money is that guy putting down to the bottom line? He’s smarter than all of us. 

Len: Yeah, yeah, yeah.

Carrie: And nobody’s talking to him. Not one vendor has approached him. But he is like he was super awkward and a little disheveled and looked like he just finished like servicing a client on site, you know? He’s like got the Polo on, it’s untucked, and kept the jeans and he was very soft spoken. Very —

Len: Yeah, you never know. 

Carrie: Yeah, but a conversation with this guy and I’m like I wanna know how he did that. How is he running a million dollars with one person?

Len: Yeah, that’s, I think, you know, a couple of really good event kind of pieces of advice, you know? You gotta —

Carrie: Talk to everyone.

Len: Talk to everyone, reach out, that’s your job, you’re a vendor, know why you’re there and it’s about getting your name out, number one. Number two, get solid leads. You’re an MSP, talk to every vendor, because you never even know if that vendor’s offering may help you, may drive more revenue, may make you more automated. So both sides have to really work at an event and I think, if we wanna go back to the last IT Nation, I mean, that’s what I saw. I mean, it was a lot of engagement there.

Carrie: I think they did a great job of that, like I love that they didn’t keep the vendor hall open a billion hours, they kept it open but you didn’t have to be there, right? Like the attendees weren’t expecting you to work the booth because the booth hours were very structured, right? We’re not gonna have booth time while there is breakouts and keynotes on because I think that they cannibalized themselves a bit in previous years because they had the vendor hall open but then you’ve got your sponsors giving their breakout sessions and if I have to choose, like, hey, do I wanna go talk to six people in this time or do I wanna listen to one vendor pitch? Like I should be able to do both. If I wanna talk to vendors and I wanna listen to vendors, how do I structure my day if the vendor hall is open all the time? What’s the easiest thing to do? Just go to the vendor hall. So if I’m a sponsor paying for that breakout session and you’re taking those people and moving them somewhere where there’s food and drinks and, you know, like, now, all of a sudden, I got eight people in the room and the 30 that would have come are now like having a coffee and chit-chatting with my competition at their booth. I don’t like that.

Len: But that’s where, again, we started, you know, early on. It’s you have to understand why your vendors are paying you money to be at your event and be very mindful of the time you give them in front of your attendees and how you do it. You can’t have — like I used to actually try to take competing vendors and just make sure that they weren’t necessarily, you know, even look at your agenda, where do you please people? Oh, do you wanna be against your competition or not, right? And listen to your vendors of how they want to kind of be positioned there. So, be very mindful as you put these events on, not only of your vendors but how you’re gonna direct your MSPs or your attendees to go visit them at the right time. And events are not trivial, Carrie, from multiple ends, you know?

Carrie: You know, maybe you don’t know that coming into them, right? If I could give anybody that was coming into the channel right now and trying to figure out their way around events, you know, Len runs a consulting practice called MSP Toolkit and he’s been doing this for 40 years. Maybe give him a call and ask him, you know, how do you structure your year? If this is your — like you got a finite budget, what events do you absolutely have to go to? And that’s different for a PE-backed vendor than it would be for another vendor, right? If I’m a small vendor, bootstrapped, trying to figure out my stuff, I’m probably going to start with the ASCII circuit or the ChannelPro circuit or something where, you know, I can figure out what my pitch is in a much smaller room and talk to MSPs that maybe aren’t prepared to spend the $5,000 and week out of the office that it takes to go to IT Nation, right? So, if you’re going to go to a local event, you’re going to get a different crowd than you will at a national event. And if I’m a smaller bootstrapped guy, like that’s where I’m going to start. I’m going to go make all my mistakes at smaller events before I try and go hit the mainstage at IT Nation.

Len: Yeah, and you better be ready when you do make that move, your business better be ready because if you’re making the move —

Carrie: Oh, we got crushed in first event.

Len: Yeah, if you’re making the move to the big event, you better make sure your business process, your lead process, all the stuff we’ve been chatting about is in order because another thing you kind of learn in the channel is, if you mess up, it’s gonna take you a while to kind of come back, you know? I won’t name a vendor but I certainly remember so many vendors coming in, PE-backed, a lot of money, come into the event, big parties, everybody loves them, start buying their product, and then it doesn’t work when it absolutely positively has to work. All that party stuff, all that relationship stuff that is so important, is what actually says, “I can’t work with those guys because I have clients, I gotta pay my bills, I gotta pay my people.” So your solution, your process, your frame, it all has to work so that you can go to an event and be present and recruit hard and hit the big ones, and funny you say it, I have one vendor client, budget for the year $300,000. We started doing a few small events, a couple big ones. Next year’s budget, $2.2 million, because they saw going to the bigger events is —

Carrie: More than I made last year.

Len: Well, because they’re a big vendor trying to come in to the channel and they have, you know, one side of their business but the whole point is, you know, they learned in year one, we did a few small things, couple big ones, and they learned the buyer they want is probably at IT Nation, is probably at DattoCon, probably at, you know, Kaseya, some of the big vendor names out there in the channel and that’s where you’re gonna find your bigger MSPs you know? Because everybody wants to go learn, you know, big and small. So, a lot of stuff to think about Carrie.

Carrie: Yeah, well, it’s been nice catching up. It was great to see you at IT Nation. I’m glad we got to finally connect. It’s been a few — a lot of years, actually, not just like pandemic but you were you were off New Zealanding for a year or two. 

Len: Thank you for having me. Hopefully, they cut this up really nice but, you know, Len from MSP Toolkit, if you guys want to get a hold of me, my email is Len@MSPtoolkit.com. Connect with me on LinkedIn. Love working with vendors trying to get in the channel. Love working with experienced vendors who still need some help, you know, putting together their programs and I certainly love working with MSPs because that’s where MSP Toolkit — what it’s all about is making sure the MSPs have the right tools, best practices to grow their business. So, I appreciate you having me and I look forward to the next time we meet at an event.

Carrie: Thanks, Len for joining us today and we’ll see you next time in the hallway.


You’ve been listening to Hallway Conference with Carrie Simpson. We work in the managed IT services industry and look forward to providing solutions to sales leaders, business technology manufacturers, distributor SaaS vendors, and resellers. To find out more about Carrie and her team, visit www.managedsalespros.com. And we’d love to connect with you on LinkedIn, search “tinfoilhat2.” Will we see you at this year’s annual conference? We will if you’re in the Hallway.