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Josh Schachter:
Then we’re right back.

Ben Winn:
Can we

Kristi Faltorusso:
do our music?

Josh Schachter:
Yeah. Oh, they changed the UI here. So I’m just

Kristi Faltorusso:
Oh, gosh. Here we go.

Ben Winn:
Play the music live now?

Interlude:
Yeah. Oh, yeah. Churned is presented by Update.

Josh Schachter:
But we’re we’re updating our branding series.

Interlude:
Welcome to UnChurned,

Kristi Faltorusso:
a show about

Interlude:
the leaders and innovators of companies who have forged incredible customer relationships and stories you can use to advance your own career. Here’s your host, Josh Schechter.

Josh Schachter:
Hello, everybody. I’m back. This is Josh, cohost of Unchurned, here with my wonderful cohost, Christy Falterusso, and not with John Johnson this time.

Kristi Faltorusso:
Sadly, John. John, when was the last time all 3 of us were on an episode? I feel like that’s been a while.

Josh Schachter:
It’s been a while. I mean, isn’t that the point of having the 3 of us?

Ben Winn:
It’s not so that

Josh Schachter:
we can all banter. It’s so that we can rotate and get the week off.

Kristi Faltorusso:
Oh, I’m here for the banter. But okay.

Josh Schachter:
Yeah. Well, John, listen. If you’re listening, I have a sincere message for you. Fuck me.

Ben Winn:
Oh, gosh. Here we go.

Josh Schachter:
I I know what

Kristi Faltorusso:
you guys Well, He had a similar message for Josh last week. So in all fairness, the 2 of them are just in this little Yeah. Love Yeah. Thing.

Josh Schachter:
Lovefest. Love triangle.

Ben Winn:
Love triangle with you right now.

Kristi Faltorusso:
Is it a triangle? I don’t wanna be part of this triangle.

Ben Winn:
Sandwich?

Kristi Faltorusso:
I guess we’re a square, though. Ben’s here.

Josh Schachter:
Yeah. That’s right.

Ben Winn:
I’m just observer. I’m sitting in the corner while you guys are doing it.

Kristi Faltorusso:
Oh, no. No. No.

Ben Winn:
Smoking in a dark chair. Well, that

Josh Schachter:
was a circle back to, to his telling me to fuck me last week. So that’s all. Otherwise, I don’t use

Kristi Faltorusso:
Oh, no. Okay. Let’s exclusive language. Let’s go right into the episode. It’s Ben, did have you ever listened to an episode? Probably not. Right?

Ben Winn:
Not in a while. I when it started, but it’s been a bit. He’s never listened

Josh Schachter:
to an episode.

Kristi Faltorusso:
Forget it.

Josh Schachter:
I mean, he was doing that when he was on it two and a half years ago. He’s like, I think you were one of the top 5 first five people that were on the episode

Ben Winn:
on our show. I’m a VC now. I don’t listen to anything except my own voice. That’s just the rule.

Kristi Faltorusso:
This is true. We’re gonna dive into

Ben Winn:
it. Venture capital.

Josh Schachter:
We are. Christie, do you wanna introduce him?

Interlude:
No. I’m gonna introduce himself.

Josh Schachter:
I love John usually does this.

Kristi Faltorusso:
Ben Win. Ben Win.

Josh Schachter:
Like, oh, Ben like, as if people know who the guest is. But, yeah, who who are you talking to today?

Kristi Faltorusso:
Our guest today is the famous is the one, the only Ben Winn. Ben, you wanna introduce yourself? Whoo.

Ben Winn:
Should I cheer?

Josh Schachter:
Wait. Hold on. Hold on. Hold on. Ben, Christy no longer knows what you do. That’s why that’s why she said you mentioned yourself.

Kristi Faltorusso:
At the VC firm, but I don’t forget the title. I mean, it’s, like, head of community. Isn’t it, like, community? That’s

Josh Schachter:
a success. Yeah. That’s an element

Kristi Faltorusso:
of success. But he’s orchestrating that through community.

Josh Schachter:
Then what do you do?

Kristi Faltorusso:
No. You’re you’re both right. Josh.

Ben Winn:
Yeah. I you know, you’re vastly right. I frame it as, customers partially customer success for the companies that we invest in. So we invest in companies, and it’s my team’s job to help make the companies we invest in successful.

Josh Schachter:
There’s no there’s no fucking way that Ben actually frames it like that to his portfolio companies. He’s just cushioning this right now for you, Chris.

Ben Winn:
I don’t

Kristi Faltorusso:
know that. When when have you when was the last time you were on his LinkedIn profile?

Josh Schachter:
He’s just still trying to be an influencer in the top the CS top 100, you know, success hacker Christy Feltaliza.

Kristi Faltorusso:
About that.

Josh Schachter:
That’s why he says it like that. He’s not in customer success. Ben, you’re not in customer success.

Ben Winn:
It’s all marketing.

Kristi Faltorusso:
He wants to make people successful.

Ben Winn:
Exactly.

Kristi Faltorusso:
Aren’t we all in isn’t everyone in customer success? Just like everyone’s in sales?

Josh Schachter:
Everyone’s a founder?

Kristi Faltorusso:
Everyone’s the CEO of their career?

Josh Schachter:
Yeah. Yeah. You work 15 hours a day and then tell me that everybody’s a founder. Okay. I digress.

Kristi Faltorusso:
I wanna exercise 15 hours

Josh Schachter:
a day. Out. I had to get that out.

Kristi Faltorusso:
Are you done, Josh?

Josh Schachter:
Yeah. So, Ben, you’re the director of communities. Communities. So the first question as well, what are the many communities that you direct? Yeah. Well, let’s start there.

Kristi Faltorusso:
At First Mark. Right?

Josh Schachter:
Yeah.

Ben Winn:
Firstmark. So Okay. For helpful context, Firstmark is an early stage venture capital fund based out of New York. We invest primarily in series a. And, historically, we’ve invested in companies like Pinterest, Shopify, Airbnb, DraftKings. List goes on and on. I can’t take any credit for those, although I’d love to. But those were long time before I I joined investments.

Ben Winn:
And Firstmark was also early to platform, which is a term that is I didn’t know about really until I joined VC. And a lot of people don’t know about it until they’re in the VC world, but it is essentially the I mean, it comes to life differently at each at each, fund. But at Firstmark, it touches a little bit of deal flow generation, so companies we haven’t invested in, and then a lot of portfolio support and founder acceleration. So

Josh Schachter:
It means you do shit to help your startups.

Ben Winn:
Exactly. Exactly. So as part of that, we build I build and run well, I took over, running and have launched some new communities. We run communities for CROs, CMOs, CPOs, CTOs, CFOs, founders that we haven’t invested in that are early stage founders in New York, founders we have invested in. We run large summits and networks of angel investors. There’s probably 14, 15 different communities of all shapes and sizes that we run. But our most fit quote, unquote famous would be our guilds, which are, communities that started out just sort of connecting the executives within our portfolio. So all the CMOs across the Firstmark portfolio.

Ben Winn:
But then a couple years ago, we started adding in select folks from the broader Unicorn ecosystem into those groups. And now what that looks like is we have functional communities across all, sorry, functional communities across all of those, areas I outlined, CRO, CTO, CFO, etcetera. And we have nearly 3,000 members representing over 60% of the Unicorn ecosystem. And those communities all get a lot of value proactively provided to them so that we can then activate folks in those communities for our founders and our portfolio companies if and when the need arises. So it’s, a lot of different communities touching basically all the great tech companies.

Josh Schachter:
I love that. So you’ve built a mouse trap for biz dev leads for your portfolio companies.

Ben Winn:
That’s one way to that’s one that’s one way to frame it. We like to think of it as, you know and we’re pretty honest about it with people in the group is, you know, we do it because, a, we’re we’re huge on New York as an ecosystem to build in and to find companies in. And so we believe that it’s it’s a good thing for all of VC for us to just invest in the New York ecosystem. 2, it’s hugely valuable to all of the execs, whether in a portfolio or not, to be in a community with the best CFOs in the world. So when SVB had its, you know, little incident last year, you know, we had over 450 CFOs exchanging hundreds of messages over a 48 hour period to figure out who was getting their funds and how are they were getting them and where they were moving them around and problem solving with each other. That’s immensely valuable, regardless of whether or not they’re in a portfolio. And then the third one is, hopefully, we can use, the context we have from running these communities to figure out good win win wins so that, when a company is looking to sell to a certain type of when a company we invest in is looking to sell into a new type of company, hopefully, that company is interested in knowing what’s cool and upcoming and what kind of access they can get, early access, preferred access to cutting edge AI technology for, just as an example. So we try to make sure it’s always a win win win for everyone involved.

Kristi Faltorusso:
Ben, how many portfolios do you guys have active right now?

Ben Winn:
We’ve got a 120 active portfolio companies.

Kristi Faltorusso:
That’s great. And then so what is your interaction with them? So, obviously, you’re orchestrating these communities, which is much broader scope. But what’s your direct interaction with each of the Portcos?

Ben Winn:
It varies. So we’re we are a high conviction investor. So we tend to do a smaller number of deals, but we go in with a larger check. We tend to take a board seat. So we our partners are very involved with those companies. I build relationships with a lot of the founders and their executive team members over time through our communities, our summits, our in person events, our remote events. But a lot of it also goes through our partners, where basically they will understand what the most critical role is that a company is looking to fill, and then they’ll let know, and then we’ll we’ll chase after that. Or, you know, I I talked with a huge with a a $5,000,000,000 company last week that’s just looking to run, like, some high value AI pilots.

Ben Winn:
And so I was able to figure out who in our portfolio might be a fit and then introduce the founders of those companies to that company. And that’s just a great way for me as a, you know, a VC to show up and actually be helpful, which is the old trope. But, hopefully, it’s actually helpful for people in a portfolio.

Josh Schachter:
What principles have you taken from your life and customer success into venture capital?

Ben Winn:
So that’s a good question.

Josh Schachter:
I’m sure I have to answer that. I mean, it’s like, we’re we’re a CS podcast, but at the same time, that’s a that’s a shitty question.

Ben Winn:
Oh, it’s always a pretty special answer. Everything’s customer success as long as you’re, the the CS at the macro level. You’re doing it very well when you figure out how to for create that win win win. Like, that that’s the whole the whole structure. Create value for the customer, extract value for yourself, and and do it in a way that everyone walks away feeling really happy. So

Kristi Faltorusso:
Ben, so you talked about the portfolio coming. These are all series a companies, you mentioned. Right?

Ben Winn:
The most part? A 120 active portfolio companies, but, only a third, I’d say, are probably series a. And Okay. The earlier stage folk are seed in series a, and the earlier stage ones are the ones that I tend to spend the most time with because they generally want and need the most support from from our team.

Kristi Faltorusso:
From your standpoint, what are some of the biggest challenges that you’re seeing folks navigate right now?

Ben Winn:
There’s a few. Everything’s pretty unique. The the ones that are not unique that will come as no surprise are sourcing customers or, you know, early user adoption and getting feedback and and, that sort of thing. A big one that’s come up recently is building culture and distributed teams. If you’re a team of, like, 6 and you’re distributed across the country or in multiple countries, how do you work together well and and cross time zones and and build culture? Finding talent is probably always one of the most critical ones because especially at that c to series b, the right leader can make or break your company. If you bring in the wrong VP of product at the series a, like, you’re screwed. You can be screwed. Yeah.

Ben Winn:
But if you bring in the right one, then that’s a rocket ship. So those sorts of things are are definitely top of mind for people at all times. The the last one I’ll mention is probably just figuring out the balance of growth versus profitability and where to focus your time and where to focus your resources. Should you just focus a 100% on growth? Or should you be given the market, you know, should you really be hyper focused on just being profitable even if that means slower growth? And figuring out the right way to calibrate those settings is, is definitely top of mind for founders.

Kristi Faltorusso:
Josh, how does that resonate with you being a founder right now? I would agree.

Josh Schachter:
I I would everything

Kristi Faltorusso:
you said, are those all of your same challenges?

Ben Winn:
No. Your distributed team, You’re early stage. Yeah. Like, what are you focused on?

Josh Schachter:
No. I I agree. I think Christie’s new podcast, she’s so sweet, is the greatest thing since sliced bread. So, like, 100%. We’re not we’re on the same page. Yeah. What’s what’s going

Kristi Faltorusso:
on with that list?

Josh Schachter:
Are you

Kristi Faltorusso:
are you still distracted by, Jackson barking in the background, and he had to go quiet the dog, and then he came back.

Josh Schachter:
So welcome back, Josh. People embroiled in this story of where I was and, like like, the fact that I’ve had 3 different people come to the door at the worst timing, and my dog is triggered by doorbells and

Ben Winn:
Spike Lee dropped by with muffins.

Josh Schachter:
Yeah. Spike Lee

Kristi Faltorusso:
Yes.

Josh Schachter:
Yeah, dropped by with muffins.

Ben Winn:
With muffins. Sorry behind that

Josh Schachter:
for all people that don’t have that context. Anyway, Ben, how are you keeping connected to this? Because you you were a maven of the CS community. One might even say you were, like, at the same level as Christie Falterusso of the CS community. Yeah, you may say that. May say that. And yeah. Like but now it’s, like, you know, the rumors of your demise have been, you know, falsely

Ben Winn:
Greatly exaggerated. Great.

Josh Schachter:
Thank you. Greatly exaggerated. Are you still keeping in touch with what’s going on in CS? And maybe tell people that are new to the world what you were doing in CS before.

Ben Winn:
Sure. So so before this, I was, head of brand and community marketing at Catalyst, which, has now merged with Tatango as of a few months ago. And, so, you know, before that, I was leading CS at Healthtech Company. So I’ve been in CS I was in CS for 9 years or something like that, either leading it or at a company that was building software for it. And I love the CS community. So, yeah, I’m still a lot of my friends are from there. I I’m still very connected, but I I would say I’m a little more out of touch on the, just on the technology side. And so what sort of what’s happening where, because we don’t spend much time in that space, as a firm.

Ben Winn:
So it’s just my mind’s much these days, it’s much more spent on, like, weird AI tech and DevOps stuff and, like, all these obscure different technologies, rather than CS world. But

Josh Schachter:
So what

Interlude:
did you were also instrumental in CS and focus?

Kristi Faltorusso:
Right?

Ben Winn:
Like Yes. I founded a CS community. Yes. CS and focus. That was that was yeah. It was my whole that was my whole world for for

Kristi Faltorusso:
It was your whole identity for a long time. Okay. Like, I feel like you’re completely downplaying it. I feel like you did a great job of, you know, starting I and you started that in Toronto. Right? CSN Focus? That was in Canada. Yeah.

Ben Winn:
Yeah. Yeah.

Kristi Faltorusso:
And then you you started the the to branch it out when you came to New York, and so then you started to do more in person events. And so I feel like you’re downplaying your role in customer success slightly by just positioning it as, like, you had these titles at these two companies, and you did this for, like, 90 years.

Ben Winn:
I I was the most sought after customer success thought leader in the world for Globally across Canada and New York. I’m most well known for the memes that I would create at Catalyst, when I started there. But no

Kristi Faltorusso:
one’s coaching corner and the community. I’m like, I can sit here and just brag on you for hours, Ben, because you did do so much. And listen, obviously, I got to to watch a lot of that alongside and be a part of some of the things that you you orchestrated there at Catalyst. But you did a lot for the community in bringing folks together and especially during a very pivotal time because a lot of that overlapped, though, with the pandemic. And so I I think you were doing a lot of really special work. Can you talk a little bit about some of the programs that you had launched and kind of what you envisioned for the community as a result of some of that?

Ben Winn:
Yeah. I mean, again, it all goes back to and, again, I think anything, anything done well, again, it’s just like, you bring a customer success mentality literally literally any practice, and you’re gonna do well. So taking it to marketing, the idea was early on, you know, peep one of the big pain points because in CS, you have to figure out what are people trying to achieve, and then how can I help them do it? So early on at Catalyst, I talked to a bunch of customer success people, and their big complaint was, you know, I don’t know how to get promoted, or I’m trying to break into CS. So I’m trying to elevate my job, or I’m trying to figure out what my next step should be. And no one really had a good way to connect with mentors and mentees. And, you know, in speaking with people like yourself and and, you know, customer success executives out there, a pain point for them was, well, I wanna give back. I love giving back, but it’s hard to know where and how I should spend my time to have the most impact. And I obviously wanna spend my time with people that are gonna actually listen to what I say and and where they’re gonna actually action the feedback that I give them.

Ben Winn:
So the idea behind the Catalyst coaching corner, which was the first, sort of special project, I guess, the program I launched at Catalyst, was let’s just connect excellent customer success executives with sort of the next generation of customer success leaders. And our first cohort was sort of really hacked together, and it was maybe 50 or no. Maybe even less. Maybe 30 mentors and 50 mentees. And it was phenomenal. And the last time I looked at the program, it was something like, I don’t know, 2,000 people now that have been through the program and a 150 mentors. And it’s just it’s gotten, it’s got it went huge, because people really recognized. Again, I always have said that, like, building community for CS people is like shooting fish in a barrel because you’re taking people that are natural relationship builders that want to help each other, and you’re like, here’s an even easier way to help each other.

Ben Winn:
And then by doing so, you know, selfishly, raised the profile of Catalyst a lot, gave us tons of of, you know, good karma out in the world by helping people with their careers. And the goal was, okay, if we help this next generation of CS people get promoted and elevate, then over time, that will help us grow into new comp you know, grow on the sales side and the growth side. So that was one big one that was that was super fun and impactful. We I did the podcast, which was originally called NPS I Love You. We did that for a year before rebranding to Humans of SaaS. That was the other one. That and then I did that for a couple years. That was really, really fun.

Ben Winn:
Got to meet and talk to great people on that. We did retain me. That was, you know, I’ve never been given the green light for a April fools joke before, to actually invest real money in an April fools joke. But Catalyst, I think I asked permission. I might have just done it and then asked permission later. But, we launched the fur Retain Me, which was a fake dating app for CSMs. And it worked so well, except for the couple people that thought it was real. And we’re very What

Josh Schachter:
do you mean you launched a fake dating app? Like, it was an actual app that you you Oh, yeah.

Kristi Faltorusso:
There was a website. Like, you went to it. Yeah.

Interlude:
It was a good thing. Website.

Ben Winn:
Yeah. It was you got a little pretty pretty far down the funnel before it matched you with Catalyst because Catalyst like, we had all these sort of funny rationales as to why Catalyst was your perfect match because it was, like, so reliable and trustworthy. And, you know, it I

Kristi Faltorusso:
I can’t remember what that look for in a partner. Yes. Right? Exactly. It

Ben Winn:
was catalyst to the software.

Kristi Faltorusso:
It was very cheeky, but very cute.

Ben Winn:
Yes. And, again, that was just like a super fun, brand building and and marketing campaign. And then the last one that I still love, that if I have the free time, I’d love to do is we launched the Unicornian, which was a it was basically The Onion, but for tech. And so it was just like all the tech things you complain about and think are stupid. Let’s do that, like, the, you know, an onion style publication. And that was really, really fun to just write. And it was very good

Josh Schachter:
Are you are you getting this creative outlet from VC? Like, are you not bored out of your mind at Firstmark now with your portcos? Because you can’t, like, do, like, the unicornian, like, for you know?

Ben Winn:
I definitely cannot do the unicornian unless I do it under, like, a fake name and and, something like

Kristi Faltorusso:
that. It’d still be a little tricky. I wouldn’t do it, Ben. Don’t do it.

Ben Winn:
Exactly.

Kristi Faltorusso:
But if you have ideas for me and Josh, we’re all ears.

Ben Winn:
Great. I’ll send them to you. So fortunately, I do have my so my husband’s a fashion photographer, and I’ve been working with him for years. And so my creative outlet has now become much more of that, where when I get to do shoots and production and, like, all that cool stuff, that’s my creative outlet. I get to do some cool stuff at Firstmark. We just did a, a founder event a few weeks ago that was, MasterChef, and it was, like, the founder. And we pitched we brought a bunch of founders to a competitive cooking experience, which, again You did a cook you did

Josh Schachter:
a cooking class. Cool.

Ben Winn:
It was a cooking class.

Kristi Faltorusso:
That’s not what it was. Josh, if you’re not listening, it was a competition.

Josh Schachter:
Oh, yeah.

Kristi Faltorusso:
Nailed and this is, like, nailed it if you’ve never seen that. Yeah.

Josh Schachter:
I’ve never seen it.

Kristi Faltorusso:
Oh, you should watch it. It’s so good.

Ben Winn:
Watch it.

Kristi Faltorusso:
It’s like it’s like normal people baking show. Like, somebody comes and makes some beautiful cake, and then they give, like, average people, like yourself, Josh, the option to try to make it that exact same thing. And so it’s,

Josh Schachter:
like Joe.

Ben Winn:
And so everyone failed to play.

Kristi Faltorusso:
Like and every yeah. And it’s, like, one person fails less miserably than the other

Josh Schachter:
2. Fun fact. I’m addicted to Is It Cake on Netflix.

Kristi Faltorusso:
Well, I mean, the question is, is it cake? I can never tell. I don’t know. So it’s crazy.

Ben Winn:
Like, chops off half her microphone, and it’s cake.

Kristi Faltorusso:
Every day, I’m walking around my house with a knife looking cake. Nothing is cake.

Ben Winn:
It’s just all sliced up right now.

Kristi Faltorusso:
It’s just all it’s just all broken wires at this point. It’s I am every day.

Josh Schachter:
Cool. Alright. So you’re having fun. You’re having fun. Different way.

Ben Winn:
Having having fun different way. But the big thing with BC and and why I still do, why I do recommend to people, you know, as as a potential path, is that, like, the the big thing Cattle said more fun than I’ll ever have, I think, at a at a company. Like, it was just so much fun. And, here, I’m learning more than I ever have because the like, you know, especially when you invest across multiple swim lanes, like, you have to understand all this different technology. If I’m gonna lead communities of CFOs and CMOs and CTOs, like, I have to be on par with them in terms of being able to understand what they’re saying, host an event, you know, have that sort of knowledge that requires a lot of research and a lot of deep thought. And so, I’m by no means an expert in all these areas, but I’m learning more than I ever have before. So it’s it’s a great career from a being challenged to learn new things perspective.

Josh Schachter:
What would

Kristi Faltorusso:
The biggest learning curve. No. Sorry, Josh.

Josh Schachter:
No. Yeah.

Kristi Faltorusso:
Learning curve. You made this transition. Wasn’t the first pivot you’ve had in your career. What was the hardest part about going from kinda in house at Catalyst to now this role?

Ben Winn:
The biggest one for me was I am very I was a very good b plus, a minus student all through school. Like, I and without studying. Right? So I was like, I can I didn’t care care about getting a plus? Like, could not give a shit. Both my siblings were, like, a plus straight students. I was like, I can have fun and then just get these good marks. And I’ve got through most of my career doing that. Right? Like, shipping quickly, getting it to good enough or, like, better than good enough, but not, like, perfect. Get it to that 80% and ship.

Ben Winn:
And so I was able to do a lot of stuff really quickly, which is great when you’re trying to grow and scale a business at series a, series b, series c. But VCs, that’s a that’s not how it’s it’s a plus every time. They’d rather you ship, you know, 3 things perfectly than 10 things at an a minus. And And so for me, it was a really big change culturally and just like a muscle I hadn’t flexed in a long time to spend that time and get every change the way that I thought the way that I worked to go from shipping quickly b plus a minus work to shipping slow a plus.

Josh Schachter:
Christie, what was your GPA?

Kristi Faltorusso:
A 398. Would you like the teacher’s email address, who gave me an a minus? Because I’ll never forget her ever.

Josh Schachter:
I’m I’m still alive.

Ben Winn:
You’re like, you haven’t killed her?

Kristi Faltorusso:
Maybe not. I don’t know. I realized how long ago I graduated college. So, and she was not young, so possibly not. But it was one of my journalism professors, and she gave me an a minus. You believe it?

Ben Winn:
I was dorky.

Kristi Faltorusso:
I went What was yours? I didn’t win. Yeah. Josh.

Josh Schachter:
Christie has me beat. I got I got one beat. Yeah.

Kristi Faltorusso:
But Josh went to Columbia, and I went to post. So it’s like

Josh Schachter:
But don’t you know that, like, you know what I’m saying?

Kristi Faltorusso:
Canada. Just went to Canada.

Josh Schachter:
I got one c. And, it was the only c that I’d gotten, and I was pretty distraught. But I was able to convince the the professor it was for deterministic models. And it was way over my I didn’t understand a single thing, not a single

Kristi Faltorusso:
I don’t even know what you’re talking about.

Interlude:
So Yeah.

Josh Schachter:
It was like I would get a g. Statistics, probability, deterministic models, like like stoicasting, blah blah blah. And Yeah. But the professor felt bad for me, and I showed up to so many office hours just trying to understand it that he turned my seat to a b minus just out of, like, the kindness in his heart.

Kristi Faltorusso:
See? Hard work does pay off.

Josh Schachter:
Hard work pays off. Yeah.

Kristi Faltorusso:
Or at least being good. At least being gritty. Okay.

Josh Schachter:
I also think I worked too hard. I think I didn’t, like, enjoy well, I enjoyed college, not enough of high school. That’s okay. We could turn this into

Kristi Faltorusso:
I enjoyed high school more, but that’s why I went to Post and not Columbia. Did you go to Columbia for grad school or just under for undergrad, Josh?

Josh Schachter:
Undergrad. Undergrad. Before, you know, be prior prior to, 10ths and you know?

Kristi Faltorusso:
Okay. Okay.

Ben Winn:
Student refugee camps

Kristi Faltorusso:
and stuff. Pretense? Got it.

Josh Schachter:
Yeah. Pretense.

Ben Winn:
That’s how we’re measuring things now.

Josh Schachter:
Yeah. Yeah. Do we have anything else to talk about, Ben?

Kristi Faltorusso:
Everything.

Josh Schachter:
I mean

Kristi Faltorusso:
Should we have Ben over? Should we go see Ben? We haven’t seen Ben

Josh Schachter:
in a long time.

Ben Winn:
Yeah. I was gonna say, like, when’s the when’s the pool party? Like, we gotta provide these.

Kristi Faltorusso:
I know. I was supposed to plan it for July, but it’s looking it’s looking like an August date.

Ben Winn:
Alright. How’s what’s going on? What have I missed in the world of customer success that I need to know about?

Kristi Faltorusso:
Oh, gosh.

Ben Winn:
As someone who’s, like, the the only news that I know is the catalyst to tango merger thing. Like, so beyond that, there’s, like, nothing in my.

Josh Schachter:
Life. Well well, Christy, you guys just had an acquisition. You had a couple acquisitions.

Kristi Faltorusso:
Have an we had 2 acquisitions. So we’ve been acquiring onboarding software. So we had an acquisition with a company called Status and then an acquisition of another company recently that we just announced called Baton. Oh, that’s awesome. Yeah. So another onboarding platform. Yeah. And they were in New York, which is cool because, like, actually now some of the employees that came along are in New York.

Kristi Faltorusso:
So now I feel like Right. I have other people in New York that now work for the same company as I do, which is pretty cool because I’ve done Alex Alex

Josh Schachter:
Alex, their CEO, lives 2 blocks from me. Did you

Ben Winn:
know that?

Kristi Faltorusso:
No. No? Their CEO is Peter.

Josh Schachter:
Oh, Peter’s CEO. Now are they co CEOs? Alex. You know Alex and Peter. One of their halves I don’t

Ben Winn:
know Alex.

Josh Schachter:
Of founders. Maybe he’s not there.

Kristi Faltorusso:
Okay. I know Peter.

Ben Winn:
I don’t

Kristi Faltorusso:
know Alex. Okay. Anyway,

Ben Winn:
he’s

Kristi Faltorusso:
your friend? He’s neighbors? He

Josh Schachter:
he’s a really nice guy. He lives in a

Kristi Faltorusso:
Is he friends with Spike Lee?

Ben Winn:
Does he brought No.

Kristi Faltorusso:
Does he also bring you muffins?

Josh Schachter:
But you know what? I think Ben has probably met Peter and Alex at my apartment before for one of my happy hours. I’m not sure you were there.

Ben Winn:
I’m sure I had.

Josh Schachter:
No. Yeah. Anyway okay. This is not interesting to anybody, but the But this is,

Ben Winn:
like, no client success is acquired onboarding software. Yeah.

Kristi Faltorusso:
So we’re going down that path. Josh, what about you? What’s going on in your world? What’s up with that? What’s

Ben Winn:
the update on update?

Josh Schachter:
We’ve had a good year and we’re raising. So we feel like we earned the right to raise. Yeah. To to That’s a lot. That’s exciting. So we’re getting larger and larger logos. And SaaS is is is all, you know, hung up on churn right now and making sure the customers are sticky. So it’s and then there’s the whole AI thing.

Josh Schachter:
So it’s kind of like

Ben Winn:
heard of it?

Josh Schachter:
Yeah. You think you heard it? Like, everything’s kinda coming together. We’re focusing our go to market, and we’re raising money to to amp that up. So, I’m, like, in the trenches right now. I think I have 4 VC calls today. Oh, wow. So yeah. No.

Josh Schachter:
I don’t know for at first mark, for First Mark Ready yet. Do you guys still have Joseph Esas? Is he still a partner there or venture partner?

Ben Winn:
No. No.

Josh Schachter:
Oh, okay. He was with you guys for a little while. He was the president, well, he was the CTO of eharmony, the dating website when I was there.

Kristi Faltorusso:
Is eharmony still around?

Josh Schachter:
They are technically. Technically.

Ben Winn:
Yeah. It’s technically over 70 to sign up.

Josh Schachter:
Yeah. Exactly. Exactly.

Ben Winn:
Okay. I am doing a, closed door AMA with the founder of Hinge next week. So that’ll be fun. Oh, that’s cool.

Josh Schachter:
That’ll be Nice. Yeah.

Ben Winn:
Have, like, a bunch of founders in their response to be like, oh, I met my fiancee on there. I met my spouse on there. And then my brother who just got engaged last week, he met his, fiancee 7 years ago on Hinge. So

Kristi Faltorusso:
So I’m wondering what the the success rate is in current time though because I don’t know if anyone watches this stuff on TikTok, but, like, epic dating fail stories and seems everyone hates dating apps, but it’s, like, the only way to meet people. So it’s, like, this necessary evil, but it doesn’t feel like it’s as successful as it once was.

Josh Schachter:
Well, step 1 is to delete TikTok. Yes. That’s probably better. No. It’s how

Kristi Faltorusso:
I learn how to, like, get dressed and put on makeup. No. All these 22 year olds. Are you kidding me? I watch more get ready with me videos than, like, anyone.

Josh Schachter:
I mean, Kylie, I’m cool. I met my girlfriend on Hinge, Christy. Jess and I met on Hinge.

Kristi Faltorusso:
Is that how you I knew you guys been on an app. I didn’t know which one.

Josh Schachter:
It was Hinge. Yep.

Kristi Faltorusso:
Is Hinge the one where the girl, like, gets to say no. That’s Bumble. Bumble. Okay.

Ben Winn:
Hinge, I think, is like their I I mean, their differentiator, I think, is, like, in the prompts that it gives you. So it, like, helps you start conversations and get to know people better rather than just, like, a Josh,

Kristi Faltorusso:
what was your prompt to meet Jess? Everyone who’s listening I’m

Josh Schachter:
trying to

Kristi Faltorusso:
be my mom wants to know.

Josh Schachter:
I’m trying to be witty. I can tell you I can tell you one that got a lot of good responses from women.

Kristi Faltorusso:
Okay. What do you got?

Josh Schachter:
Was like the 3 causes that I care most about. Oh, interesting. Can you try to guess one of them, Kristi?

Kristi Faltorusso:
Is it no. I can’t. Is it dogs? Is it dogs? I’m guessing. Is, like, one of them pet related? I don’t know.

Josh Schachter:
No. No. No. Actually, I don’t know if I remember the 3rd.

Ben Winn:
Are they

Kristi Faltorusso:
because I’m, like, I don’t know if you’re going, like, are you going political? Are you going religious? Like, I don’t I don’t know where are you going with this? No. Go down

Josh Schachter:
with. Climate change. Right? Preventing climate change. One was one was gun control. And then, I forget what the third one was, to be honest with you. But, anyways, that that was always good. And then I did the, they do like a 2 truths and a lie. I hope we don’t have any listeners at this point.

Josh Schachter:
I’m pretty sure like everybody’s like already like tailed off.

Kristi Faltorusso:
They dropped. They dropped. Okay. So so go give me what are your okay. So what were your 2 truths and a lie?

Josh Schachter:
So so, well, I I can’t think of it all the time. So you know you know, it’s you’re gonna know which is which. I love pizza. Nope. Got that wrong. I love cheese, but I hate pizza. I guess

Kristi Faltorusso:
that was Love cheese. Hate pizza. Continue.

Josh Schachter:
So that was a lie. Love cheese. Hate pizza.

Kristi Faltorusso:
Oh, there.

Josh Schachter:
And that got so because it’s the opposite. I love pizza and hate cheese. And that got so many responses from from women in New York because they couldn’t believe they’re like, oh my god. Right.

Ben Winn:
I hope

Josh Schachter:
you don’t hate pizza. Pizza. Yeah. Exactly. So that was, like, the number one. That’s it. If you want if you’re a

Ben Winn:
guy that unhinged Localize your like, do, like, a local base, like, if you know your Yeah. Like, answer. That’s a good that’s a good time.

Josh Schachter:
Yeah. You could probably even go hyperlocal and be, like, favorite pizza places. Or you do, like, the the Dave Portnoy version of it, and you can, like, you know, have people Yeah. On top

Ben Winn:
of that side. Like, you could get really Yeah. And you’re going very targeted.

Josh Schachter:
Yeah. Yeah.

Ben Winn:
I like that for you.

Josh Schachter:
But I I’ve probably been on more dating apps than anybody that you guys both know. I definitely have been on more dating apps than anybody you both know.

Kristi Faltorusso:
How many dating apps are there?

Josh Schachter:
Well, first of all, I was I was single for a while. Right? But, like, second of all, because I worked at eharmony, I was exposed to, like, the whole flurry.

Kristi Faltorusso:
Work to eharmony?

Josh Schachter:
Yeah. That was actually my first, like, proper job in tech. And, so I was a product manager. And what do you do? You get inspiration. Well, you sign up for all of the dating apps. So I was on them all, like, you know,

Kristi Faltorusso:
this is

Josh Schachter:
best? Who did it? Okay.

Kristi Faltorusso:
Plenty of fish. I’m guessing not plenty of fish.

Josh Schachter:
Plenty of Fish is really interesting. So Plenty of Fish. Again, we don’t have anybody

Ben Winn:
here listening to any

Josh Schachter:
like, Plenty of Fish was, like, a guy and his assistant in, like, the basement of a house. I’m exaggerating, like, in New Jersey.

Kristi Faltorusso:
You could tell that by the UI, though.

Josh Schachter:
Right. But this guy was making, like, 10 mil a year as just, like, a lead generation to the actual dating site. So you would come there, and then you would just Oh,

Kristi Faltorusso:
that’s how he was monetizing it?

Josh Schachter:
Yes. Yes. And so, like,

Kristi Faltorusso:
it’s like the juice. Grimy. Like Yeah. Plenty of fish. Horrible.

Ben Winn:
Yeah. I feel like every murder show I watch starts out with, like, well, she broke up with her husband and then just joined Plenty of Fish when she met the perfect guy, and then it’s Yeah. Devolves.

Kristi Faltorusso:
Definitely the it’s definitely the beginning of every 2020 episode.

Josh Schachter:
But so we would advertise we would advertise on on Plenty of Fish for eHarmony, and I was part of a startup that they started. They were trying to go more casual, and so we started jazzed. Jazzed.com.

Kristi Faltorusso:
That didn’t do well, did it?

Josh Schachter:
That was, like, the hookup version, but, like, it did not do well. It was out of business in 18 months. They moved me over then to mothership.

Kristi Faltorusso:
Surprise it lasts that long. The name alone doesn’t really, like, it doesn’t give me jazz.

Ben Winn:
Yeah. What would rumors find exciting? Yeah.

Josh Schachter:
Well, that’s the thing. Like like, the company is being run by, like, the 75 year old, you you know, like, very religious, like, conservative southern guy that, like, you weren’t gonna get very far with, like, a more progressive website. And they had passed on purchasing OkCupid for 30,000,000 a year prior. Can you imagine OkCupid for 30,000,000? Now it’s probably

Ben Winn:
for, what,

Josh Schachter:
3,000,000,000 something? And then, like, no. We can build it ourselves. Well, we couldn’t, but we tried. And this is probably right around the time that Tinder was being incubated. So they, you know,

Kristi Faltorusso:
they were.

Josh Schachter:
But, yeah, OkCupid back in the day had some cool features. They were they were doing some cool stuff. I don’t know what that was.

Kristi Faltorusso:
And today, what would be the top app?

Josh Schachter:
All Clearly Hinge. That’s where I met my, you know

Kristi Faltorusso:
Okay. My

Josh Schachter:
other half.

Kristi Faltorusso:
I know that there was other ones. It was, like, bagel and donut, and then there was like there there was

Josh Schachter:
a lot. Circular

Kristi Faltorusso:
scale. Like, the really niche ones. Right? You had, like, the the popular farmer one? Farmers only or farm yeah. It was, like, farmers only, which that’s wild.

Josh Schachter:
They do have in New York, they have the Locks Club.

Kristi Faltorusso:
Do they?

Ben Winn:
Yeah. There’s the Locks Club. Like LOAC, but,

Josh Schachter:
that’s funny. Yeah. Yeah. Yeah. For, like, for all the people in my neighborhood, all those upper east side folks, right, that locks What’s

Ben Winn:
the Oh, I’d

Kristi Faltorusso:
be like, that’s targeted. I like that.

Ben Winn:
Yeah. What’s the elite one for, like, extra hot people? Isn’t there, like, a a one you could apply to?

Josh Schachter:
Raya. What is it called? Raya. Raya? I’m really enjoying this right now because, like, I

Kristi Faltorusso:
Wait. Hold on. How do you get on

Josh Schachter:
that site? About this until nobody is listening to the rest of the show.

Kristi Faltorusso:
How do you get how do you get approved for this really hot cheating?

Josh Schachter:
I’ve tried. I’ve tried in the past. I never was able to.

Ben Winn:
No. No. You I’m serious. Founder. I’m a founder.

Kristi Faltorusso:
Make a certain amount of money. Like okay. So is this, like, one of those ones where it’s like, if you’re a guy, you could be less attractive if your income is over x, and if you’re a girl, you don’t have to make any money, you don’t have to have any morals, but you have to be really hot.

Ben Winn:
This is also what we have for founders at pitch us, by the way.

Kristi Faltorusso:
Oh, interesting. Okay.

Josh Schachter:
That’s your criteria.

Ben Winn:
Definitely not. This is not just for legal disclaimer. Definitely not.

Josh Schachter:
No. You have to you had to submit your TikTok or your Instagram. They had to look at your phone number. And you had to be a referral. I don’t know. But you had to be a referral, and I never was accepted. And it was a little bit more like arts artsy people. It’s kinda like Soho House.

Josh Schachter:
Right? Like, they’re looking not to get,

Kristi Faltorusso:
like,

Josh Schachter:
you know, a little bit more of, like, the the actors, the athletes, the artists.

Kristi Faltorusso:
Yeah. I’m not fancy enough for that stuff. It’s good to get married.

Josh Schachter:
Yeah. No. There’s lots.

Ben Winn:
I want to bring it to something vaguely relevant. I actually do have a question for you guys, which is, have you seen any cool innovative uses uses of AI in customer success beyond, like, chat gbt products? Like, are there any

Josh Schachter:
Or my own company.

Ben Winn:
Data AI, which we know about. Or But maybe people ways people are using UpdateAI or ways maybe a client success you guys have put into practice.

Kristi Faltorusso:
Not in customer success, but customer experience more like for support agents, like call centers and stuff like that, like that customer experience side. I feel like they’re doing really interesting stuff. Customer success, not What

Josh Schachter:
are they doing that stuff

Kristi Faltorusso:
for 10 years?

Josh Schachter:
They’ve been doing that stuff for 10 years, Christy. That’s nothing wrong.

Kristi Faltorusso:
Well, so so I’m just saying, like, I mean, like, I listened to the CEO not CEO, but somebody from, Microsoft was talking the other day, and it was, like, what they were doing. And it was, I don’t know, know, wrote it all down. It’s actually effective because

Josh Schachter:
you’re saving time.

Kristi Faltorusso:
Their innovation around what they were doing. I was kinda sitting there, like, oh, wow. Okay. Like, that’s cool. They’re doing like a voice augmentation for people in call centers. So that way if you outsource your teams in India, it localizes their voices so you don’t know. So if you’re calling from the states and you speak with somebody, they have, like, a 100% retention on calls with 0 escalations. Like, I’ve been listening to all these, like, case studies and success stories about stuff and, like, I think those are really interesting ways.

Kristi Faltorusso:
Obvi obviously, like, things to maintain omnichannel experiences for customers who are in those experiences, better chatbot experiences. I think what folks are trying to do is figure out how to create better employee experiences as well as customer experiences through AI, which I think is really nice cause I think a lot of people are still trying to figure out, if I am a human in that ecosystem, do I will I have a job in 6 to 12 months? And there’s a lot of fear that people are navigating, so I think it’s more like, how do you enhance the humans that we have and and and make the work that they do better?

Ben Winn:
Yeah. Is there a world, Josh, where something like UpdateAI just eclipses all customer success software and that you can just follow people from call to call, track their emails as well somehow, and then basically just, like, do all of it. So I don’t have to, like, go somewhere to look at a health score or look at, like, the most recent thing. I’m basically getting fed. Here’s the context of what happened and where. Here’s the recommended action. Should I do it? Hit yes or no. And then it sort of takes care of it.

Ben Winn:
Like, is that in the in the in the near future?

Josh Schachter:
Yeah. You want a job in product at my company? That’s, like, that’s the vision. That’s the vision. That’s awesome. But, yeah, I mean, CSPs are antiquated. What? Who said that?

Kristi Faltorusso:
I was gonna say, actually, it’s interesting who will get there first because I think the CSPs who house all the data will likely leverage technology like Update to go and be a part of that and leverage all the data to do all those cool things you just said as opposed to it being backwards where all the customer data now goes into UpdateAI. I agree. I do think that you’re gonna see some really interesting use cases, but I don’t think anyone’s nailed it just yet. I think there’s a lot of, like, ideation that’s happening right now, but I haven’t seen anything in practice. And I think a lot of companies right now are advertising AI first and all of this stuff. But when you go and see, I’m, like, no. Just because, like, you have some, like, features that maybe are using AI functionality. I wouldn’t say you’re an AI first platform.

Ben Winn:
Did you guys see the thing about Amazon? Amazon Go where you could walk in and take a sandwich and, like, it would just charge your account.

Kristi Faltorusso:
Yeah. It was

Ben Winn:
like it was a whole call center in India where they were watching people. Like, there was, like, little to no actual AI happening. It was all this

Kristi Faltorusso:
part of the realize that.

Ben Winn:
Yeah. It was, like, entirely vaporware. Like, I feel like there’s like, most of AI is still that where it’s, like, sub like, we’re just farming out all this other stuff to, like, someone else.

Josh Schachter:
I love that so much.

Ben Winn:
And charging way more for it.

Josh Schachter:
I can you imagine being Amazon that big of a company and still running that scheme? Like, I I respect that so much that they that they

Kristi Faltorusso:
good for them.

Ben Winn:
Right? Because, like, I mean Yeah. I know.

Kristi Faltorusso:
Well, it’s like Josh. Josh’s company will worth be worth $1,000,000,000 one day just because he was smart enough to have AI in the name.

Ben Winn:
Yeah. Exactly. We well, this

Josh Schachter:
is free. That was the only domain available. This is 4 years ago. I hate all this.

Kristi Faltorusso:
Exactly. That that that worked for you. Yeah.

Ben Winn:
We invested 10 years ago in a company called x.ai. And we’re like, goddamn. Like, it would have been worth so much. Just the domain alone

Kristi Faltorusso:
Just the domain.

Ben Winn:
We could have just flipped to Elon for an insane

Kristi Faltorusso:
amount of money. Say, like, isn’t x calling? Like or Twitter. Does anyone even call it x?

Ben Winn:
Trying to. It’s hard. Are you?

Kristi Faltorusso:
It’s called Twitter.

Ben Winn:
I kinda hate myself whenever I say it. But

Kristi Faltorusso:
It just feels wrong.

Ben Winn:
Yeah.

Kristi Faltorusso:
Yeah. Is that how we end?

Josh Schachter:
I think so. Sad x. Ben, I think you should actually come and be a cohost when when in in in when one of us are in abstention.

Kristi Faltorusso:
You should bear sanding.

Josh Schachter:
Yeah.

Ben Winn:
I’m always happy to be in the air.

Kristi Faltorusso:
I can’t. I have a real job, and I have real work, and I have real things I have to do now. But thanks.

Ben Winn:
I still love CS, and I love, moderating conversation with interesting people. So this has been a blast. I’m always happy to if all of you get into, like, an actual fight with each other and can’t stand to be on at the same time, I’m happy to stop.

Kristi Faltorusso:
It’ll be Josh and John first.

Josh Schachter:
Yeah. Yeah.

Kristi Faltorusso:
Probably sell tickets on pay per view.

Josh Schachter:
Yep. That’d be fun.

Ben Winn:
That’s see, you could do a whole marketing campaign around that. Alright. Well, I know that.

Kristi Faltorusso:
I can’t, but you can. And, we’ll get this pool party on the schedule for,

Ben Winn:
for

Kristi Faltorusso:
our fellow New Yorkers. Although, I keep inviting Josh to come over on Fridays, and Josh doesn’t wanna come over. So and hang out with you.

Josh Schachter:
Slash has a day, Josh. Have a wonderful week after 4th July, everybody. Ben, thanks so much being on the program. Christie, love you as always. Bye.

Kristi Faltorusso:
Thanks for having

Josh Schachter:
me. Bye.