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Josh Schachter:
Hey, everybody, and welcome to this episode of CS and BS Unchurned. I’m Josh Schachter, your host. Usually, I have Christy and John and and the cast of characters, and they’ve all abandoned me this week. And, it’s, like, back to being OG when it was just my podcast, and I could do whatever I wanted. So, this is fun. And I’m really excited about my guest today, mister John Gleason. John is a former CS executive at Motive. He’s also the founder and the GP at Success Venture Partners, and he’s one of the key organizers of the customer success meetup, which is storming various cities and, the the the meetup of all meetups in the customer success community.

Josh Schachter:
So, John, thank you for being with me today.

John Gleeson:
Oh, man, Josh. It’s so good to catch up, and I’m honored to finally get to join, the pod. This is awesome. So thank you.

Josh Schachter:
We’re honored to have you. We’re honored to have you. And and Christy and John send their very best. They’re they’re stuck in transit in flights today. But we’re really excited. We talked about actually, we’re gonna do this episode. This episode was gonna be with with, with 5 people, and somehow we got it down to to 2. Right? It was gonna be with with Gemma, Cipriani Espanera as well.

Josh Schachter:
We were gonna talk about, all things VC and venture in the world of customer success. Now we’re gonna talk about all things Success Venture Partners and what you guys are doing over there with your portfolio and your thesis and all that stuff. So I’m really excited about the conversation.

John Gleeson:
You have stuck with me, man. Yeah. There’s many people. Right?

Josh Schachter:
We’re stuck together. We’re stuck together. Alright. So, before we tell everybody to to invest their money, in your fund, let’s let’s, like, let’s boost the credibility a bit. Let’s let’s start to, like, do some some validation of of who you are and your background and and that you know your shit. So so tell us, John, you were you left tell us your background. Are you, you know, your VP at Motive? Yeah. Go.

John Gleeson:
Okay. Cool. And I’ll give you you know what? I’m gonna give you, like, the long answer because I think it’s, like, always important for people in CS to, like, understand maybe, like, where somebody came from to understand, you know, where where they’re going. Perfect. So, for me, like, I’m a startup person, like, through and through. If people are familiar with, like, the work of, like, Steve Blank and Starting Lean and the Lean Canvas and all of that, I came out of that class, teaching, you know, I was always an entrepreneur, but I didn’t quite know, like, you know, where my entrepreneurial canvas would be until I found my way into that course on how to build, like, a high growth technology software business. So for for folks who haven’t read, Starting Lean, you know, 5 Steps to Epiphany, all that Steve Blank work, like, put it on your your mind screen.

Josh Schachter:
Like the he’s like the godfather of of start ups and and iteration and lean start up. Like you said, before there was Eric Ries and and those folks, it was it was Steve Blank. Right? He’s, I don’t is he a professor somewhere? He’s somehow academic.

John Gleeson:
Right? Yeah. He’s a professor at Berkeley.

Josh Schachter:
At Berkeley?

John Gleeson:
Yeah. Yep. At Berkeley. And and, yeah, everybody, like, riffed off of his work. And, Yeah. 90% of the companies out there, they get founded with that test iterate type model.

Josh Schachter:
Yeah. I reached out to him 4 years ago to invest in UpdateAI when we didn’t even know what we were. And I somehow came across his email, and he was kind enough to to respond, not not invest, but I was happy with the response at that point.

John Gleeson:
Are you, like, always stoked when you, like, send off that cold email to somebody you admire and they, like, they actually respond to you? Like, woah. This is so cool. I’m connecting with my hero.

Josh Schachter:
Oh, totally. Totally. I mean, quick story. When I was in college, I was running the ice hockey team. Right? And I know you’re a hockey player. And so I ran the the club hockey team at Columbia. I think our annual budget was like $10,000 which is not a lot of money with New York sheets of ice, right, even back 20 years ago. And this is, like, even before digital.

Josh Schachter:
I went into the alumni office or the administrative office. There’s, like, a big encyclopedia, encyclopedic book, like, a 1,000 pages of all the alumni email addresses and stuff. And Henry Kravis was an alumnus of of Columbia. Henry Kravis is the Kravis in the k and KKR. Right? So billionaire upon billionaire. I went to high school where he went to high school, I knew he kind of had a connection to hockey. I cold emailed Henry Kravis and asked him to donate money, this billionaire, right, like, barbarians at the gates, like, the guy who started all of private equity and asked him to or the leveraged buyout and asked him to donate to the Columbia ice hockey club team. And he responded.

Josh Schachter:
No. He didn’t. But he responded, And I was, you know, 19 year old kid. I was so excited that this guy had even just responded. Okay. Now back to now back to your background, John.

John Gleeson:
So that’s the original Steve, seed for me, Steve Blank. But, anyways, I was in this course, and we had to, like, build a company. So chapter 1 for me was basically joining a company that I connected with in this class, hire number 1, preproduct market fit, move to New York City because we had a a thesis that our ideal customers were in New York and, like, literally, like, hustled my way around New York, much like you’ve been doing for the last few years. Just like, you know, like, you get your subway card. You go uptown. You go downtown. You eat pizza all day and just will your way in front of your first customers. So that was, like, chapter 1 for me.

John Gleeson:
And it it went, like, really well. Basically, we found some product market fit, so then I became, like, seller number 1. I was, you know, boots on the ground. Did the proverbial first $1,000,000 in sales, and that was going well. So then we had to, like, hire a sales team. So the founders are like, hey. Build the sales team. I was like, cool.

John Gleeson:
Can do that. So built out the 1st sales team. And then we had all these customers that we needed to renew, and the founders are like, yo. We’ve been reading this thing called customer success. You know, here’s a blog post. Oh, yeah. By the way, this is your new job. You’re the figure it out guy.

John Gleeson:
Figure out customer success. And I actually, like, went into that being like, well, this is a silly name. This probably isn’t very good for my career. You know, like, give me something substance with, like, sales. Everyone knows what that is. Anyways, it turned out to be, like, a really good thing for my career. The whole category of customer success was, like, exploding at at this point in time. Ethi Cannata, the original, Gainsight CMO, was putting on these amazing events, and they just, like they needed people to go on stage.

John Gleeson:
So long before, I was worth my salt in customer success, I started to, you know, help the Gainsight crew evangelize this this movement.

Josh Schachter:
Sounded like the original pulses that you attended and spoke at?

John Gleeson:
Yeah. Original pulses. We did, like, you know, virtual pulses too live from New York, and we’d, like, go, like, film in Bryant Park. So this is, yeah, this is, like, the Nice. Way not way back in the day, but, like, almost 10 years ago now. Yeah. Yeah. Yeah.

John Gleeson:
That was, like, chapter 1 was just, like, coming of age, like, found my way into customer success As the 1st hire in a startup, though, and this is where, like, chapter 2 starts, you get to ride shotgun with the founders on everything that they’re doing. And so one of those things was fundraising. And, you know, this again, 10 years ago, you actually got on a plane and you went to Sand Hill Road. And I was like, dang, man. I would love to be on the other side of the table one day. Like, venture seems like the most exciting thing ever. These are people, and their job is to take interviews all day to learn about what the future is gonna look like. That seems endlessly stimulating, but that was not an option for me at that point in my career.

John Gleeson:
But I I basically took the insight, which was, okay. These folks are investing $1,000,000 in a company. They’re making a bet. I don’t have $1,000,000 to invest, but I have 4 years of my life. So, like, pick a winner. I I would say, like, joining a start up, joining a company is probably the most concentrated bet you can make. Yeah. And so I just, like, set up Crunchbase, and, every company that raised a a seed or a series a over the span of about 6 months, I just, like, did my homework.

John Gleeson:
So chapter 2 really started for me when I found this little company called KeepTruckin’. Less than $1,000,000 in ARR. A lot of people in New York thought I was crazy. They were like, what do you mean you’re moving across the country to join a company that is digitizing something for truckers? Like, it’s just, like, outside of the world that people knew. But I love the founders, and I was like, no. This is gonna be big. And then so the conclusion of chapter 2 was really through that company from less than a1000000 in ARR to $300,000,000 in ARR when I left, and we created a $3,000,000,000 company.

Josh Schachter:
So What what was it about? So it was called KeepTruckin’, now it’s Motive, right, by the time you left? And by the way, it’s such good advice. Listen. Now now is really tough for for SaaS and for CS and and and a lot of people out there looking for their next thing. So not not everybody has that ability right now to perhaps be so selective, and judicial. But, like, I love the fact that you thought about it in the sense of my next role. If I’m gonna go the startup route, if I’m not gonna go work for Procter and Gamble or whatever, then it’s really the biggest bet that I’m gonna make. Like, that’s my investment. That’s, like, the same thing as calling my money manager and saying, hey.

Josh Schachter:
You know, put it all on this ETF. So Yeah. You you wanna really feel that conviction, not just for the sake of, like, oh, cool. Like, I’m gonna get this title, and I’m gonna be at the start up. Like, no. Like, this this equity I want to actually have work out. I hate like, I like the way that you that you position that for yourself.

John Gleeson:
Yeah. Oh, it’s so important. And, you know yeah. I can’t stress that enough. And and I think too, like, doing those exhaustive searches where you, like, find the company that you want and you, like, will your way into it. Because that’s what I did at, at KeepTruckin’ Moto. Like, they’d already hired their head of customer success, but I was like, I love this company so much. I’m gonna, like, find a path in.

John Gleeson:
I’m gonna make even a role for me in the company. It’s like I always say it’s like, I would rather be the player on a team who’s, like, the 4th line, to use a hockey term, but, like, winning a championship or have the chance to win a championship every single year, then the superstar, the team that’s not going to the playoffs, maybe you get to go to the all star game, but, like, the end of the Yeah. At the end of your career, like, you know, the the people who have really achieved the most did so alongside the very best team. So, like, you know, make it all about the company, the team, you know, all boats rise, I think, with a rising tide. And, I think that gets overlooked so often.

Josh Schachter:
And by the way, we know from we’ll just stick with Aki here. Like, we we know that those those plumbers, right, those 3rd, 4th line guys that are doing the grind work, when they make a deep playoff run and they’re up for free agency, the the money comes. Right? So they get rewarded for playing that that that role position. They get rewarded for it from being on on the team that has been successful even if they weren’t playing that marquee role. So there’s something to be said in your career as well. Like, you want those logos to follow with you and that story to be part of your story. You know?

John Gleeson:
Totally. Yeah. Totally. So chapter 2. So now we’re moving to chapter 3. So I made a goal when I got out to Silicon Valley. Like, I want to get into venture on the other side of it. And one of the ways that you get into venture is, 1, building a really good network, but 2, making some investments.

John Gleeson:
Like, you need to have kind of a track record before you can even get into venture. So we got out to Silicon Valley, started to write some some seed checks, very small. Like, we’re not talking a lot, like, $5,000, really small checks.

Josh Schachter:
You had left you had left Motive at this point?

John Gleeson:
Oh, no. So I’d left my first start up, joined Motive. Now I’m in, like, Silicon Valley. I’m I’m on the stage where I wanna be. Motive’s going really well. We started the meetup. Janan, had started the meetup and I joined. So it’s starting to see, like, you know, just like the piping of how Silicon Valley works, around networks and, you know, people helping people and putting back in and then getting opportunities to invest in your friends or your friends’ companies, things like that.

John Gleeson:
And so, while I was at Motive, you know, I always said to myself, when Motive IPOs, I’ll go into Venture. And the thing that I need to get into Venture is to have a track record. So I just started to write, like, some seed checks. Then Index Ventures, who was on our board, was like, hey. You keep passing us some pretty good deals. Like, do you wanna be be a scout with Index Ventures? And, basically, that’s where they set up, like, a bank account in your name, their money’s in it, and you get to write checks, to seed stage and precede stage companies, and it’s all part of building their pipeline. Most famous scout. Yep.

John Gleeson:
So I became a scout with Index Ventures, which was a wonderful experience. The most famous example of, like, a scout hitting a home run is Jason Calacanis. Right? He was a scout with Sequoia. That’s how he wrote that check into, Uber. That obviously ended very, very well, for for him. So became a scout with index, started to build out that track record, and I always thought, like, yeah. Motive’s gonna IPO. Maybe I’ll put the hard press on on Index, and I’ll get to finally get into venture, with Index Ventures.

John Gleeson:
But, really, the epiphany that came to me while I was doing this, and I think you’ll appreciate this, is there was nobody out there investing professionally who had the post sales side of the go to market strategy, in their head or had seen it at scale, through as many stages of growth as as I had. And that was really compelling to founders. And so, like, you know, you’ve been out there fundraising, Building a cap table with all the skills that you’re going to need to be successful as a company is, is important. And so I found myself, like, winning space on these really competitive cap tables where there’s not a lot of space left and being able to just, yeah, create room for this value that I can offer. This is still

Josh Schachter:
as a scout. This is still as a index venture scout.

John Gleeson:
Yeah. This is still as an index venture scout. But once I started to see this happen, like, man, I couldn’t put that back in the box. And I was like, there’s gotta be a venture firm that exists that provides value to entrepreneurs for everything that happens after they get that logo. And so that’s what we’ve been building, really, for the last year now, is a a venture firm that our value add to entrepreneurs isn’t, you know, helping them hire. It is. We can help them hire, but it’s really like working with them on everything that they need to do once they land that first customer or that 10th customer or that 100 customer. So really bridging from, like, pre seed, seed all the way to series a is where we can help.

Josh Schachter:
And what what’s the, what’s the driving force for you to focus on post sales and customer success? Is it I mean, it sounds like I guess it’s because it’s your background and also just there wasn’t anything out there at the you know, before you started this?

John Gleeson:
Yeah. So okay. So, you know, like, you know, how these, like, funding rounds happen is, like, generally, you know, a company will raise, let’s say let’s call it, like, an institutional seat. They’ll raise an institutional seat. You know, big name x, y, z will come on. They’ll buy up most of that cap table. And then there’s maybe $1,000,000 left over, and then everybody fights over that remaining space. Right? There’s some scarcity there.

John Gleeson:
And I saw, you know, founders or other founders of other companies winning that allocation. I saw some, like, smaller funds work a lot with, like, go to market fund, GTM fund as as you know. Yep. So they’re kind of, you know, creating space for themselves there. And I just saw, like, this opportunity where it’s like when I shared with founders, you know, hey. What are you gonna do once you get that customer? They’re like, I never even thought of that. I’m definitely gonna need some help with that. You could win allocation.

John Gleeson:
And so, like, I’m not investing per se in the next, like, CS technology. I’m investing across, like, all of SaaS. The thing that I help founders with is customer success post sales, expansion, account management, onboarding, the things that I learned and got really good at at at KeepTruckin Motive. And that’s like a winning strategy. There’s basically, like, 3 pillars in ventures, like your ability to source. So can you see the best companies, your ability to pick them, which is TBD. You don’t really know if you’re good at that for about 7 years. It takes a while for startups to become a thing, and your ability to win allocation.

John Gleeson:
And so the customer success thing for me is my secret sauce or, like, my competitive wedge in order to win allocation in really hot companies.

Josh Schachter:
Yeah. Because you can go in there with and talk about immediate value that you can add to to the company. Yeah.

John Gleeson:
Yeah. And unique value prop too. Right? Yeah. Yeah.

Josh Schachter:
So alright. So that’s the 3rd pillar. So let’s go to the other 2 pillars. So sourcing and making the decision of what to invest in. What are you seeing right now in your deal flow? What what are the trends and patterns out there? Your you recently closed your first fund, right, and not too long ago, and so you’re just starting to deploy capital. Is that right?

John Gleeson:
Yeah. So I’ve wrote 2 checks out of the fund to date. So we just did our 1st close, about 2 months ago. And, yeah, we’ve written 2 checks out of the fund. So pretty cool.

Josh Schachter:
Are are you are you are you sharing the names or or not publicly?

John Gleeson:
I can share one of them, and I can share a little bit about the second one. Okay. I don’t think I can share name yet. But I can

Josh Schachter:
You got you got an audio. If they’re CS based, I don’t know. But, you know, you’ve got a captain captive audience here of inquiring minds of CS leaders and practitioners. So, you know, shoot with what you can.

John Gleeson:
Cool. Well, maybe what I’ll do is I’ll share with you, like, just my thesis for the world because I think, like, you and I have, like, a very, very similar thesis, about the world. So, like, both of us love AI, and, you know, we’re not building foundational models, and I can’t even afford to play at that level of market. So we’re at the, like, the app end of the, AI

Josh Schachter:
ecosystem. Anthropic investments.

John Gleeson:
No anthropic investments. It’s kinda like you know, I always think of, like, the analog is like cloud where it’s like, we’re not building a super scaler here. I’m not AWS. I’m trying to find, like, the next Salesforce, that technology that’s built on this this technology to come. Just like you’re you’re gonna be the next Salesforce. Right? You’re building on that infrastructure. So, you and I both know, like, there’s 2 places that these models work really, really well right now at the application layer. It’s 1, support.

John Gleeson:
Right? Finding the right ish answer in large datasets

Josh Schachter:
Mhmm.

John Gleeson:
To make the people, you know, serving the customer more effective. So that’s number 1. Let’s call it support. And number 2 is, like, writing code. Right? It’s really good at writing really good code. So the change in the world is, 1, you can now or hopefully, we’re getting there. Update dotai is solving this. You can now serve your customer with a greater margin, or with a better margin than you’ve ever had to or been able to before.

John Gleeson:
That’s really important. And you can also build at a faster pace than ever before. Right?

Josh Schachter:
Yep.

John Gleeson:
So pillar 1 of my investment thesis is, like, undoubtedly, the cost to serve customers is gonna come down, and your competitive mode in this is you have to know your customers at a better level than ever before because the pace of innovation is, like, changing so quickly. That’s why we’re seeing, like, you know, all these companies that, like, you probably win business off of at series b, series c, series d, more mature companies who, like, you almost have feature parity with them because some of those modes, those technical modes have been eroded because of the shift. So, you know, why you’re winning is because you are out there in the world understanding your competitors and your customers at a better level, and you can build faster than ever before. So, like, pillar number 1, margins improve. The key to success is know your customers at a better level than than ever before and certainly better than your your competitors. So that’s pillar number 1 in my thesis. So, like, I call it things that serve customers and or the people that serve customers. As that happens, what I think we’re gonna see is we’re gonna see actually more and more software fly into spaces that have been truly underserved by technology and software.

John Gleeson:
Like Motive, we brought 1 in 4 commercial vehicles or SMB commercial vehicles online for the first time ever. People at every investment round, you know, everybody always say, oh, it’s too small of a market. It’s too small of a market. It’s too small of a market. We always took a discount, I think, on our valuation because, like, people pigeonhole us into trucking. Well, you know, joke’s on them. We created a $3,000,000,000 encounter company. Yeah.

John Gleeson:
Rich

Josh Schachter:
riches riches in the niches. Riches in the niches. That’s what I always say.

John Gleeson:
Niches. I love I love that. I’m gonna steal that. Yep. But, yeah, especially too, though, as the margins get better, we’re gonna see it be possible to actually serve smaller and smaller niches. And so I’m really long, like, vertical SaaS things. So the first, the first investment out of the fund is called a company called Lomi. I’ll tell you about it in a minute.

John Gleeson:
But, serving these real world spaces, maybe smaller TAMs than, traditionally would have been acceptable. But if you can really serve their needs well, you can expand out the total, value that you can basically extract from that that customer base and give them lots and lots of solutions Sure. That that help to look around. So pillar number 1 is things that serve customers and or the people that serve customers. Pillar number 2 is technology for the real world or vertical SaaS for, underserved areas of of the world who haven’t experienced, like, all that software can do for them. That’s pillar number 2.

Josh Schachter:
So so tell us about what was it Lomi?

John Gleeson:
Yeah. Lomi.

Josh Schachter:
How do you loan loan me? Like, loan me the money?

John Gleeson:
No. No. Lomi, like, the gardening that I did over the weekend, the soil, man, it was Lomi. It was, the the highest quality soil.

Josh Schachter:
Okay. How do you spell that? Because I wanna I wanna give them the proper plug here, but people need to go what to need to know what to go to.

John Gleeson:
Yeah. L o a m y. Okay.

Josh Schachter:
Lomi. Lomi.ai, I’m gonna guess.

John Gleeson:
I think it’s getlomi.com. Okay. Dot

Josh Schachter:
com. Yeah. Google around for it. You’ll find it.

John Gleeson:
Google around for it. But, anyways, it’s 2 founders out of Motive. That’s one of my sourcing flywheels is just, like, a lot of people come to me when they’re building stuff for the real world. Right? Motive’s known for has a company that built stuff for the real world. Anyways, these founders came out of, Motive. The one of the founders was actually on my original customer success team, at at Motive or keep tracking before moving into product. But at Accor, what they’re doing is they’re building a logistics solution for the low end of the agriculture industry. So, you know, you show up to Costco, on any given Tuesday, you can get get blueberries for $8.99.

John Gleeson:
Right? Downstream, those blueberries are coming from, let’s say, Driscoll’s. Right? Downstream from there, Driscoll’s is sourcing from, let’s say, 20,000 farms around the globe so that they can procure berries, so that on any given Tuesday, they can deliver to, to Costco. Well, the problem there is, like, most produce actually, like, doesn’t make it to the shelves. Only 4 out of 10 berries get to the the supermarket shelf. And it’s like

Josh Schachter:
just Because of expiration of the food or or all kinds of things.

John Gleeson:
Yeah. Fruit doesn’t wait for anyone. Actually, here’s here’s when I was doing my due diligence on this, when COVID hit, they canceled all visas, Right? All visas got canceled. The very next day, they reinstated one visa. It was the h one b a visa. I wanna say it’s the farm laborers visa. And basically, what they realized was like, if they didn’t have hands to pick this fruit, like, we would have a massive food

Josh Schachter:
The food supply. Yeah.

John Gleeson:
Food insecurity problem. And so, like, the very next day, they reinstated this visa. Anyways, Lomi is solving the logistics problem, that exists between 20,000 farmers and getting the berries to Driscoll so that they can end up. And it’s a logistics problem at its core. So these founders are you know, they built a logistics solution at at Motive. They know the problem cold, and I’ve worked with them for 5, 6 years, and part of the stage that I invest in is just, like, knowing the right founders to solve the right problem, and and it’s a bet on on people too. So Cool. That’s the first investment out of the fund.

John Gleeson:
I’m super stoked on it, but, yeah, solving a real world problem for a space where the existing incumbent is is literally you know, looks like Windows 95.

Josh Schachter:
No. I love it. It actually reminds me a couple of years ago, I sat down with the CEO of the Boox, like bouquet, the boox.com. And I’m actually a big user. I have been historically, in that product, just really high quality flowers. I felt this guilt when I lived over in California. My whole family was on the East Coast. So I signed up to this, like, you know, bouquet subscription for my mother and my grandmother just as, like, you know, on demand or in the background.

Josh Schachter:
I didn’t even realize it, but all of a sudden, they receive it every 3 months and think that I’m, you know, God’s gift to, you know, being a grandchild or whatever. But anyways, I remember sitting down with the CEO and that company, despite all the like, it’s a subscription business, it’s a B2C business, you know, all these sorts of things, It’s actually a logistics business because it was all about how to get the flowers from Ecuador. I think they were primarily sourcing them and reduce the time it took to get to, distribute them to the actual, you know, end customers. And they saved, like, 1 week per shipment of flowers on the end to end supply chain. And that’s what allowed their flowers to stay nicer for an extra week, which is where you pay premium for higher quality flowers. Yeah. So it’s the same thing. I totally buy into

John Gleeson:
it. Cool. That’s awesome. I was taking notes there. I’m gonna do some Googling on that.

Josh Schachter:
Yeah. Check it. Yeah. Yeah. Yeah. I can I can try to introduce you to John Tabis over at the Boox? Good guy. I think he’s I think he’s kind of like emeritus status right now, you know, because he paid his dues building the company for the 1st decade. Yeah, similar type of model.

Josh Schachter:
Yeah.

John Gleeson:
Cool. Love it.

Josh Schachter:
So the other thing that you’re very active in and people, you know, maybe even primarily know of you from is, the customer success meetups that you do. And so you you’ve now been expanding them. You’ve got really exciting stuff coming in for the fall in New York City. Tell us a little bit about for for folks that, you know, maybe haven’t been to one of the meetups, give us the rundown on what you and and Junan and and Monica and the team have been doing there with those meetups for a few years.

John Gleeson:
Yeah. So okay. I’ll tell you, like, the genesis of of the meetup. So we really, like it was an excuse to just talk to, like, the very best leaders in customer success. We’ve been doing them since 2016. Janine always jokes that at the first meetup, there was more pizzas than there were people. I think it was raining in San Francisco and the warriors were playing, in the playoffs. So that was a flop.

John Gleeson:
But, basically, over the years, what it’s come to be is is, like, really cool in person community. We you you see us on LinkedIn. We’re really not very good on LinkedIn. You probably would never know that we had existed, because of LinkedIn. But we’ve just been hosting these events where we put people who are, like, deep in practice on stage. We’ve got a mailing list, and we send out a notification, and we kinda throw a party with it. We have really good food now. We’ve graduated from pizzas.

John Gleeson:
I like to think, like, conference level content. You get really good speakers. Yep. And, and, yeah, we we we host them. So now we’ve got them going in San Francisco, New York City, New York City just because, like, I have such an affinity for New York because the 1st years of my career, and I love the CS leaders in in New York. And, yeah, our goal with it is, like, we don’t make money with it. It’s, you know, not trying to become another job, although it it is a job in and of itself. We do it because we love it.

John Gleeson:
We we’ve had people at our meetups who become best friends, who go mountain biking together on the weekends, who’ve helped each other get different jobs. So the reward for us is just, like, seeing, like, this very organic in person community flourish, and that’s a good dopamine kick when you step back from the evening, and it’s been a great great event. People are smiling. So, anyways, that’s what it is. We’re hosting our biggest meetup ever next fall, October 3rd in New York. It’s gonna be 800 people. We’ve had so much demand for our recent meetups that we’re running out of, like, venues, free venues to to host them. We send an email and, like, 500 people sign up.

John Gleeson:
We can usually only accommodate about 200 per fire code. And, yeah. So that that’s what it is, but it’s it’s really like

Josh Schachter:
So I’ve got my I’ve got my I I bought 3 tickets the other week, for the I know.

John Gleeson:
I saw that. That was awesome. And as I came through, I said, yes. There we go.

Josh Schachter:
Yeah. You you got me on the discount. I have to say, I was gonna be there either way, John. I shouldn’t admit that. But, you know, as I had to do it. And, actually, one of them one of the tickets is for somebody who I don’t even know who that will be yet. It was just, you know, we we wanna come strong.

John Gleeson:
Maybe maybe whoever, like, emails in,

Josh Schachter:
podcast

John Gleeson:
with, the best new lead for Update dotai.

Josh Schachter:
Okay. Done. Done. Let’s do it. I’ll take it. Great. If you email me, josh@update.ai, with a lead, that that that that becomes something or even close to something, then you will be rewarded with a free ticket to the

John Gleeson:
It’s up the bar. Fortune 5 106 figure deal. Come on. We love the community. Good news for Josh here.

Josh Schachter:
I’ll I’ll take I’ll take anything over a 10 k ACV. How about that? That that that that feels worthy, of of a free ticket to the event. What’s the what’s it called, John? What or is there a website or anything?

John Gleeson:
We’re working on the website right now. Gainsight’s gonna be a big sponsor. So we said we wouldn’t, spend a lot of time promoting it till after Pulse. So we’re May 20th.

Josh Schachter:
Yeah.

John Gleeson:
We gotta get going. You can visit us at, I think, customer success meetup.com. There’s some information there. We’re gonna launch the website and all the speakers, hopefully, this week if Janan finishes the website.

Josh Schachter:
Love it. Come on, Jinan. Get on it. Get on it. And Jinan, I I forget his last name, but he’s he’s a a a a customer success, leader manager at Slack. Right?

John Gleeson:
Yep. Yep. He’s the head of customer success for the Americas at Slack. He’s one of the best long tail customer success I’ve ever met. He’s good.

Josh Schachter:
Awesome. Cool. What else, John? That’s all I got for you. You know, Christy and and and John Johnson weren’t here for the hard balls. Team. So I threw you some softies.

John Gleeson:
I don’t know. What’s, like, what’s, you know, what’s, like, what do you think of just like all these releases last week? Like, I’m curious to pick your mind. Like we had, update AI or sorry. Home Home. You know, the big, the big a one. I’m looking at your hat right now, and all I can think of is

Josh Schachter:
Yeah. No. Omni. Right? OpenAI Omni?

John Gleeson:
Yeah. So we well, just like 4 do we say 0 or 4 dot o or the new, new I

Josh Schachter:
think it’s Omni. I think they’re calling it Omni. Yeah. Yeah. Because I think it’s a 4, and then I think the it’s like the, you know, the Latin or the Greek o. I think it’s omni. Okay. I could be wrong.

Josh Schachter:
But, yeah. I love it.

John Gleeson:
Google’s going down, and then we, yeah, we have Facebook scorching the earth with their, open source

Josh Schachter:
Yeah.

John Gleeson:
Models too. So, like, yeah, what what’s your take on the world?

Josh Schachter:
Oh, it’s hard to keep up, honestly. I mean, I I’ve fiddled around a little bit with Omni. I’m a big chat GPT fan despite fact that we have AI in our platform. I mean, I’m still I’m still I still use Chat gbt probably a good 20 times a day. I mean, to probably to a fault, honestly, because I probably lean on it in times where I don’t have to lean on it, where it’s like, I’ll feed it I’m writing an email, and I’ll feed it a paragraph to polish for me when probably would have been quicker not to do that. But I just you know, every once in a while, it just it just gives me gold in in ways to think about what I’m writing. Usually, it’s what I’m writing. Right? But a lot of times, it’s other, you know, looking up references and things like that.

Josh Schachter:
And, I think, if memory serves, because I was at Pulse last week, so my head was completely at a booth and buried.

John Gleeson:
You had a full on week.

Josh Schachter:
Yeah. Yeah. I’m still kind of at my post pulse recovery. But by the way, it was amazing. I will give since Gainsight’s sponsoring your event and and we work closely with them, It was exciting, and I was a little bit dubious of Pulse in Missouri in St. Louis. So, you know, Nick was on 2 weeks ago, and I kinda ribbed him a little bit. I was like, so, Nick, what’s the real reason of cost savings that Pulse is in St.

Josh Schachter:
Louis this year? You know? And he he wouldn’t let me get there. But then I but then I I was there last week, and I was like, you know, maybe maybe it wasn’t just a you know, because it was cheaper than Moscow. And, like, St. Louis actually was a really nice place for it because you kind of took over a little bit. It’s a small it’s a small city, so it had more of, like, a vibe around Pulse. You know, the the conference center is the conference center. It was just as nice or or or, you know, whatever as Moscone. And, and it was easier for folks to get to for most of us.

Josh Schachter:
So it yeah. So it was a good event. That being said, yeah, I am completely anything that happened in the news in the past week, I’m completely out of. I just happened to to read about the the, ChatGPT Omni before, like, while I was on the flight over there. And something that’s exciting, I think, still trying to figure out, like, how we would apply it in our product, not tomorrow, but, you know, let’s say next year or later downstream, next couple of quarters, is so as you know, we we take, recordings and the transcriptions and we synthesize insights and generate all that stuff, right, for for customer conversations. But now there seems like there’s more availability for generating insights around video and and imagery. And so I’m thinking to myself, like, how could we use that? So if you’re in a call and you’re showing your QBR deck or your onboarding deck or whatever, and now all of a sudden, you know, GPT is able and these other technologies are able to give you insights around what’s on the screen. That or or somebody’s body language.

Josh Schachter:
Right? Like, that’s even the next gen of sentiment and those sorts of things.

John Gleeson:
Oh, I, like, I completely, completely agree. 1, when you were saying, you know, you rely on it to a fault, I’m the same way. I found myself on an airplane, with no Wi Fi a week ago, and I was like, what do I do? How do I do my job? And I agree too. I think like we’ve seen so much around, tax. That’s been amazing, but, you know, if we’re going to take it to the next level, I think like the voice image and even, like, avatars, like, I was blown away. Did you see Reid Hoffman AI?

Josh Schachter:
Oh, I haven’t booked I haven’t seen it. No. I hear it’s pretty impressive though.

John Gleeson:
Oh, it’s so cool. It’s like it I I challenge everybody to, like, watch that and just, like, think about, like, what the future could be like. But, basically, yeah, it’s they trained up this model on every podcast, every book, everything that Reid Hoffman has ever done. So it’s like the all knowing Reid, and Reid Hoffman has a conversation with his avatar. So it’s face and voice. The voice sounds like Reid Hoffman, and he puts Reid to work or Reid Hoffman puts his AI to work, and it’s it’s pretty amazing, the dialogue that they have. And you start to see, like, where, like, yeah, the outer bounds maybe of of AI could be. I felt like watching that, I was getting, like, a glimpse into into the future, which the second investment is, is in that is is in that thing.

Josh Schachter:
Okay. The there

John Gleeson:
was from 6¢. She started 6¢, and, I’ll I’ll I’ll I’ll see.

Josh Schachter:
I know I know you’re saying too much. I know. You’re trying to keep it on lockdown. It’s fine. We won’t I won’t I won’t beat you into that one.

John Gleeson:
Everybody can everybody can Google that. But, no, I agree. I think, like, we’re, like, in in anyone. It’s such exciting times for you, you know, like, creating the category really that you are. It’s gonna be fun.

Josh Schachter:
Yeah. Yeah. Totally. I mean, when when we first kinda came across when when because we weren’t really early to GPT. My younger cousin tells me in hindsight that he I told you 9 months earlier that to go use GPT. It’s like, Ben, I don’t know. Did you really? Are you just claiming that now? But, anyway, so we kinda came into it around the same time as everybody else. And we had been developing our own NLP, you know, natural language processing.

Josh Schachter:
And I remember giving it to my head of data science to play around with and coming back with him to him 2 weeks later. And I was like, Sergei, what do you think? And I was worried that he was gonna be completely crestfallen, and this is it. Like, he’s he’s leaving the company. And he came back. He’s like, well, it’s better than ours. Great. Like, we will never catch up, and that’s fine. But then and so then, like, my heart sinks.

Josh Schachter:
And I’m, again, waiting for him to leave. And he’s like, but this is really exciting because we can do so much more now. And that’s really like, it for us, it just unlocked a universe of of capabilities that, you know, now we’re we’re continuing to to roll out. So it is exciting times. It is exciting times.

John Gleeson:
I think, like, I think we’re entering one of the most exciting, albeit, like, different scary times ever. Totally. But, I just, like, I feel like I have so much, like, I’m so invigorated right now on, like, startups and people who are building. And it it’ll be like any other technology shift that has come before, but it’s like these early years where, like, you know, the sky’s the limit, really, of what we can do, and it’s just fun to pay attention. It’s, you know, it’s so interesting. Like, I was like I always like I like studying, like, technology shifts that have come before, like the iPad or, you know, mobile or certainly, like, the cloud is the one that, and you think about so many of those things that you, like, just take for for granted. And, like, that, like, that didn’t exist. And like, now you can’t live without them.

John Gleeson:
It’s like I spent the weekend, thinking about my lawn as middle aged people do. And like this dearth of content online and all these other middle aged dudes talking about their lawn on YouTube, it’s, like, one of my biggest sources. And, like, I, like, pinched myself because, like, that wasn’t something that, like, even in Carthage existed. Like, YouTube wasn’t a wasn’t a thing. I was reading over, like, old blog posts over the weekend where it’s, like, Chris Dixon had wrote, the things that people are doing in their garage this weekend are the jobs that people will have in 10 years from now, is an old blog post from, like, 2,000 15 or something. But it’s so true. It’s like, you know, you’re building a company around this, but there’s lots of folks like us who are, like, playing with all of these releases and trying to build things.

Josh Schachter:
Yeah. I think

John Gleeson:
that come out. And, like, that will be what our job is or what it looks like in 10 years from now, the things that are happening in the start ups or in the garages today.

Josh Schachter:
Yeah. Well or or not none of us have jobs. And so the job is that we’re just we have to find new hobbies. There there is a school of of folks that that believe in that. Like, we need to get you we need to find hobbies quickly within the next decade.

John Gleeson:
But yeah. Well, we could we could start a hockey team together. There we go. There you go. We’ll do it.

Josh Schachter:
There you go. Yeah. Cross continental hockey team. I like it. Which we could call it, like, the KHL. You know? Yeah. Cool. Alright, John.

Josh Schachter:
Let’s leave it at that. How can people reach you, if they wanna reach out to you about the CS meetups? Will you give them the domain there? Janan, get get you know, John, get get get on that. The Success Venture Partners, you know, everything else you got going on.

John Gleeson:
Yeah. Just email me. I try my best to respond to all of my emails. So it’s just John, this is dangerous. I’m gonna get spammed so hard.

Josh Schachter:
Yeah. Totally.

John Gleeson:
But it’s just johnjoechen@successvp.com. There’s really, like, yeah, 3 things that I love to to do is I love to see the future. So if you’re building a great company or you know somebody building a great company, it’s never too early to get in touch with folks doing that. So send it my way. That’s really

Josh Schachter:
fun. That is a good question, though, because, so the first thing when I get, you know, inbound or whatever from from, investors, my request my question to them is, well, what stage are you interested in? What what levels of of revenues are you looking at? So what is your response for that?

John Gleeson:
For me, it’s the earlier, the better. Like, I love to meet 2 founders who are just coming out of, you know, a a great company, have seen some success before, maybe, maybe not, and, like, are in that ideation phase where I can, like, help them maybe find their first, like, institutional investor, where I can, like, come alongside them in their journey. I’m trying to help them as best I can, like, even before it really gets off the ground. Early is better. But, certainly, if if, you know, a company is about to raise a really hot series a and there was one spot left on the cap table, that’s helpful too. But earlier, the better. I’m new. So I’m working really hard, and I’m trying to help as many people as I can.

John Gleeson:
So that’s, like, that’s number 2 is like the meetup. Bring great people. If we can help somebody via the meetup, we’d love to help, on that one. Like, if you’re coming in to meet up to look for a job, that’s cool. That’s one of the reasons we do it. But try and put back into the community before you take out. And if you email me looking for your next job, like, make it a little bit maybe more specific. Be like, yo.

John Gleeson:
I noticed that you’re connected to the CEO of this company. Could you make an introduction? Here’s a blurb that you can forward, stuff like that. Yeah. Make it easy on the people, who are trying to help you, or else you’ll get buried in the bottom of their inbox because you have to wait till the weekend when they have time to do that.

Josh Schachter:
Alright. Well, that’s the golden tip of the hour right there because that that applies to many people out there. Very good advice. John Gleason, thank you so much for spending the afternoon with us.

John Gleeson:
Oh, of course. Well, have a wonderful afternoon, and I cannot wait to see you, in probably 2 weeks if my Yes. My flight come true. Yes.

Josh Schachter:
Thanks, man.