Rich DiTieri
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Jeff: [00:00:00] Alright, Rich, man. Thanks for coming on the show. We've known each other for a long time, but it's fun to have you on and get to dig into some of this stuff, and maybe a little bit of stuff I didn't know as much about you.

Rich: Yeah, it is totally my pleasure to be here, man. I'm glad that our 12 year friendship has paid off with my first media appearance in some time.

Jeff: I'm glad it aligned well that the date worked out today. So thanks again for coming on. I'm stoked. So let's jump on in. We normally kick this off with a little warmup. To start I think I've run into this and I'm sure you have as well, product management and product in general can be a fairly To put it loosely broad role.

that in mind, how do you talk about what you do and how do you frame what you do maybe to, to someone outside the tech world, right? Like I always use the example, my mother in law still has no idea, almost 20 years later of being with her daughter, what I do. How do you explain it to, in that kind of context that someone can understand what product management is?

Rich: Yeah, it's a great way to put it because it is super broad. I don't know if this is a controversial take, but I view it as it's to me, it's entrepreneurship is the way I always talk about it, which makes sense for me. And I have the [00:01:00] benefit that everyone that has ever known me is like, Oh Rich is an entrepreneur.

So that tracks. But the way I explain it, including to my kids, I have a four and a six year old, and I say, I solve problems, right? My job is to figure out, is there a problem that needs to solve? Should we solve it? Which I think is always an interesting question because not every problem needs to be solved.

Or is there an opportunity of something like, that there's that to build a solution or make something easier for somebody or whatever. So I tell my kids , Hey, you guys know how you play games on your apps or play apps on your iPad or whatever. Well, Someone needs to figure out if that should get built.

And. And what it should actually look like and what it does and all that. And that's my job. So we figure out, is this something we should do? Can we make it better? Can we solve a problem for somebody or build something fun or cool or interesting? And then I get the people together who actually know how to do it.

Cause I don't actually know how to build anything. But I'm good at bringing people together to do it.

Jeff: I love the framework. , people often, I feel leave out that second part of what is it? You were so busy figuring out if you could do it. You didn't think about if you should do

Rich: that's right. I love that's the Jurassic park. [00:02:00] Exactly. 

All right. Uh, tools. We all have the things we use and love and can't live, day to day. And I feel like even though we're in a world where we're over tooled are there, like three things that you can't live without, work wise?

Jeff: I, I want to narrow it down to that you can't live without.

Rich: know, I'm so simple. I was trying to think about this ahead of time. It's funny. Cause I've actually never really considered myself a product manager. So when you were asking me coming on here, I was like, Oh man, I

Jeff: Dude, you're such a, you're such a product person. Like you, you've always been a product person.

Rich: It's funny. I didn't think about that until a few years ago when I started here, which had that in the title.

And it certainly is more formal in that way than any previous work I've done, but no, there are only three that I really care about, right? Honestly, which is. It's Miro, Asana and Microsoft Teams. Cause we're a hybrid team. I'm remote. I got a couple of people on my team that are spread around the country.

Most of them are in Boston. So teams is like critical, but Miro and Asana are like, if those don't work, like everything comes crumbling down pretty quickly. So yeah, [00:03:00] I'm just a big fan of those. We're big on project management in Asana with a bunch of automations and things to just, It's so easy to just like lose focus on what you're doing when you have a million problems to solve.

There's an abundance of opportunity to build cool things and solve interesting problems. Those to me, they're like blinders. I open it, I filter and I'm like, cool. Now I'm thinking about nothing else. 

Jeff: Back to, should you solve it? And it's not always don't solve it. Cause we might get T Rex's but just more like, is this the most important thing to work on?

Rich: That's right. Yeah. Is this actually a priority? The lens I think about it a lot is, does this move the needle on the business or not? Does this solve a problem that's really relevant for somebody or is acutely painful? Or not. And if it's not cool, it's going to go into the backlog.

Jeff: now, I'm kind of just to hear your answer on this one, because we joke on this show that people come to product from all sorts of different backgrounds. And it's, I think we had last week on someone who has been in product for, since the late nineties to now, and that has been.

I think he's the only one we've had on the show since [00:04:00] doing this, for nine months or something at this point who had that background. But you have an especially esoteric one. You've been a founder, you've done biz dev, you have been a founder again, you were a consultant at Deloitte, like you've been all over before you came to a capital P product role, even though I do maintain you have been a product person for as long as I've known you.

What I guess looking at the world of product right now, what's maybe a controversial thought you have or what's something you see that's popular that you think is being done wrong or maybe not being done that should be being approached differently.

Rich: That's a good question. I think the one that I see crop up in my world and I have to be honest to I'm not hyper connected to the rest of the product world. Cause I never, again, I just didn't consider myself as like that person. I'm way more in the entrepreneurial startup y sort of mindset.

And a problem that I do see come up here is. letting the tail wag the dog, meaning, somebody has an idea and they're like, I want to do this because it seems cool or it's what the customer would want, but [00:05:00] it might not be, or the worst case is the technology driving the business versus the business driving the technology.

We're aware of it. Like we talk about it at work a lot. Like we have something comes up, it gets into a product meeting about we want to go and do this. And now we actually have people around the room who might raise their hands and say, Hey This might be the tail let's not do that thing.

But to me that's far and away. One of the biggest, the second thing I'll say is that, and I actually, I think it's how I ended up in this job actually, because there were folks in the role previously that kind of like never really. Got the stuff across the line that we were hoping to, is thinking about all the different parts of the business.

And rather than often, I think often just the technology or often just the customer, which are good. You gotta understand both of those. But marketing plays a role. Finance plays a role. The cx, the support team plays a role in understanding, hey, if this, if we're gonna go and solve this problem, build this thing, build this product, try to roll this new thing out, whatever it is.[00:06:00] 

There's 10 business processes that are affected by this. And if we don't make sure we understand the waterfall effect of that, you accidentally break stuff like really easily. We have last summer we were a week away from launching a huge internal product and we almost broke the business. Somebody literally had to raise their hand and say Hey, heads up.

Have we figured this little thing out? Because if we don't. I think we killed a business like Overnight . And we were like, whoa. That never came up. . Yeah. And it had never come up. And it was like that one conversation with a particular person in a particular business unit that didn't seem like they'd be affected was like, Hey, wait a minute.

I think this assumption you have isn't true and it's gonna break everything.

Jeff: I think that's an OKR actually is don't destroy the business,

Rich: It's a big one.

Jeff: It's like the unspoken always on OKR is did you destroy the business? If

yes, very bad. 

Rich: Yeah. Yeah, no, you get in a lot of trouble if you destroy the business overnight. Don't do that.

Jeff: yeah. You might even lose your job. 

Rich: Of people, but yeah.

Jeff: so it from that point of you, you're [00:07:00] coming at this, I think very differently.

Again, then a lot, maybe a long time capital P product people. I guess being integrated now into a much bigger org, cause you're coming from companies that either you found it and took zero to one to, a lot of people to you've operate within that world and now you're at EF, which is a fairly large company, thousands of people what do you see around you that.

You think product folks are doing that really rubs maybe other stakeholders wrong way. Like, where is there room to improve how that function works across the board?

Rich: Yeah. I don't know. So EF is interesting here. It's like weirdly siloed. It is the biggest company that you don't realize is the biggest company. We have over 50, 000 employees. It's

Jeff: Yeah, it's huge.

Rich: It's massive. And our Boston office is something like 3000 people to put in perspective of how much bigger it is in Europe.

So like Zurich is our headquarters and it's just so much bigger. But it's interestingly very siloed. So I actually am in this cool spot where I am running products, digital product for basically two internal startups. Yeah. That's awesome. Which is like obviously a [00:08:00] good fit for me, but I don't cross paths a ton with some of the other businesses, product managers, but I see their biggest challenges for sure are that, it's just very difficult to manage all the stakeholders.

In that large of an org, like you, you have basically it's a very large business. I actually don't even know the numbers. So just big is the answer. You have some big business and you have to be super careful not to break a thing that's working. And so the product managers jobs here for some of these larger businesses are like, they're very difficult to succeed at.

I would argue because As you're trying to iterate and make things better, you're always judging it against the cost of, Hey, like this tweet, like if there's a negative effect of this thing, like that's a huge impact on a massive business. So they have to iterate particularly on technology very cautiously.

The folks have done are doing a pretty good job with it, but it just, it means you have to go a little bit slower than you might want to. And so folks that have struggled sometimes come in, try to be really fast. And real like bump into a bunch of brick walls and go, Oh [00:09:00] man, this isn't going to work because it doesn't solve a problem for these 10 people, even though it solves for these other five.

And then they have to stop and totally shift strategy and try again. And so the go slow to go fast is often a better method here. I've seen it's worked well for us.

Jeff: That makes sense, right? It's one thing if you accidentally destroy the business, that is the new upstart that you're going to have. Within a billion dollar company, then, you can probably fix that, but if you destroy the main, one, that's really bad.

Rich: I mean, Even if you just heard it a little bit, it's really problematic, right? And EF is interesting. It's not a digital product company. It's a world, real world experience. It's international education and travel education and life experience. That is almost hard to define. There's like a spontaneity. That happens there and serendipitous learning that is like you put an experience together and you have the serendipitous experience that changes your life. You can't like totally productize that in a perfect way and certainly not digitally. So the digital stuff is second class to that here.

It's really in support of the in person experiences. [00:10:00] And so you treat it with caution.

Jeff: The digital is more about enabling those serendipitous experiences. And how do you help that happen? Not, it's not the business itself. 

Rich: There are businesses here that are more digitally focused, but for the most part it's real world experiences. Yeah.

Jeff: Nice. All right, let's totally pivot here. You posted something on LinkedIn that, goes back to even long before you and I met.

And you talked about in college, but I loved this kind of core thesis that you put forward of find your weird little club, surround yourself with the people that inspire you. And that's just so freaking cool. Like I think, the idea has been put forth before, but you crystallize it in just such a cool sounding way that I'm like, yeah, of course, rich would put it that well.

But, you talk about this thing, Jeezy basement Over at at college and what that turned into for you and how that, inspired you later on. But can you maybe explain that briefly and how has that led to how you look at kind of building networks or building, that weird little club in other ways now?

Rich: [00:11:00] Yeah. I'm so glad you picked up on that one. I'm not a big LinkedIn poster. I'm like just super not that big about LinkedIn. 

Jeff: Realized when I was researching to talk to you today.

Rich: Yeah. It's boy, Rich has not said anything on LinkedIn in

years. And I really, I just, I really don't, but I had logged in for the first time in a while and I got inspired by this post of my friend, Blair Neal.

He used to go by Blar. It's like hard for me to not say Blar. But he, his name is Blair Neal. And he had reposted this time that he had been the basically the digital art production person for this band called Fantagram, which is like a very famous band these days. But we actually booked a GZ basement a million years ago at our little venue.

We basically ran a music venue in college. And it was him sharing this amazing experience of when he ran it at some big festival in LA. And it made me realize how transformational this little club was. So here is very quick context. I went to RPI. It is literally where the word nerd was invented. It stood for drunk.

This is for drunk spelled backwards, K N U R D, because we're all the nerds that [00:12:00] stayed home and studied instead. Not the most social school. I think it was ranked the second most depressed student body in the country or something when I went there. Which makes sense because they also had the second most homework out of any college in the country.

So I was like, yeah, I think these are correlated. But anyway, I, a tougher first year and then eventually found this club. And it was full of just like a bunch of creative weirdos, who were making a bunch of digital art. Everybody was in bands. I was in bands and we ran this music venue and had all kinds of creative people and artists and musicians and everybody coming through the space.

And we were totally the weird kids on campus, like for sure. And I have followed these people over time and they, and so many people have gone on to do incredible things. And to this day, 15, what's it 16 years since I graduated, something like that. My closest group of friends are still the people that I met at that, people who were in my wedding, my best man.

All that stuff was all from that little club. And a bunch of them really went on to, to be tremendously successful. And what I found when I was reflecting on it was that they are all like these [00:13:00] super curious people who get obsessed with the thing and are just sort of like, this is my thing, I'm gonna go and be amazing at it, and just, Kept on trying to be amazing at it and stayed hyper curious.

There were all people that, you could talk to about some random topic that came across, in front of you that day, and you'd talk about it for hours. And so I was thinking about how I followed that through my career. Totally. So it's, I think I've found that there's like this addiction or I'm energized, at least magnetized by curiosity and I'm allergic to apathy. And I think if in your career, like in your, in a given job, I certainly think about it for myself. I've done a lot of career coaching. I think about this when I'm coaching people on career choices. If you don't feel like you fit in, if you don't feel like you can have long conversations with people about something I'm, I love when I'm working with coworkers and something, some random topic comes up about physics or some biological happening or whatever.

And you just go down the rabbit hole with them and realize, oh, man, these people obsessively are interested in [00:14:00] learning and growing too. And if you're surrounded by folks who don't have that drive to just get involved. Keep consuming information and keep growing. If you find you might be getting a little bit stagnant, I think I could also hit with an ethical.

side of it too, and caring about your work. So the Deloitte thing was interesting. I started as a consultant, like you said, and I just so never felt like I fit in there. I was pretty good at the work. I could succeed at it, but I couldn't make myself care about it. A lot of it, some of it I did, but a bunch of it, it was like, man, I just it's very hard to be interested.

And I found a lot of my colleagues, people I was working with, didn't feel like this weird little group of people that I could just talk to about anything. I got a lot of kind of weird looks of like, Rich, why are you like talking about this weird thing? I don't know. It's interesting. And I just didn't last at it.

It just didn't, I felt so allergic to it. And then when we went and started Pintly and found the startup ecosystem in Boston that's when I found, Oh my God, I'm surrounded by people. Who are passionate about solving problems in ed tech or healthcare and biopharma things and alternative energy [00:15:00] and things like that.

There are problems that people really care about solving, even though they're overwhelmingly challenging and they're having fun. We were having a blast back when we were at mass challenge and those early days, and even still now. Because if people care about what they're doing and it's easy to talk to them and it's easy to collaborate, even when it's hard, then the work is fun and it's easier to be successful, I think too.

So yeah, that's what clicked for me. It's like, find your little weird people who care about things that you care about. It's a lot easier to do a good job and enjoy it.

Jeff: Yeah. We joke here sometimes, or I joke with the team here that we somehow have biased ourselves to hiring for almost like obsessiveness or neuroses. And I think you put it a lot better is find people who care because it's very hard to do great things, to do hard things. If you don't have a little bit of obsession I think honestly, the difference often between like good and great [00:16:00] is you can't hit great.

If you're not a little bit obsessed, at

Rich: Yeah, you have to be a little bit crazy for sure. And, obsession is certainly a form of craziness. And I think like when I talk to people about career goals and pathing, you think about any real job or career in terms of role, team, and mission. It's what are you going to do day to day?

What is your actual work? And are you going to enjoy it? If you want to be building things with your hands physically, then sitting on the phone all day, maybe it's going to drive you crazy. Your team is, that's the people you're working with. And that defines the culture. And if you can't get along or like the old Google thing was be stuck in an airport with somebody and enjoy it it's going to be tough.

But then the mission is the product. And , if you can't really care about what you're building it's, even if those other two are there, that it's going to be tough. So you're looking for alignment on those three things. I think the team is most important of the three, but it's way better when you can get close to perfect on all three.

Jeff: Yeah, so I think we started to touch on this, but you started out at Deloitte and then I think it sounds like very quickly realized, maybe this isn't the [00:17:00] thing that you are going to care deeply and emotionally and with deep conviction about. So you, you pivoted hard, man, and you went from being a consultant to, I think probably a company that ended up at the nexus of two separate weird little clubs.

When you started Pintly, so you were, smack dab in Boston tech ecosystem and mass challenge and startup world, but also this growing world that was craft beer, which is how you and I met way back when. And you ended up coming out with a company called Pintly and a app and , solving the discovery problem around like this growing.

industry that was these little local breweries in this world that was popping up. How'd that decision happen? And what was the thesis behind that company? Like, how'd you wind up on this is what we're going to build. And this is, what we're going to help the world understand.

Rich: I think there, there was what felt like an acute problem to solve. So the founding story is actually that it was my roommate from Deloitte who had the idea. I was coming from the Troy area where I graduated [00:18:00] in New York and moving to Boston where I knew nobody.

And Floyd had put this list out of here's people who need roommates. And there was this guy, Tim, and we. We chatted over the internet and I came out to Boston and I was like, I guess I'm going to live with you. And 

Jeff: that stage of life that how that happened. You're like, yeah, sure, that works. I'll live with you for a year, at least.

Rich: yeah, it was just totally serendipitous and basically what would happen is we would travel for work. We would fly out on a Monday. We had, it's called the 3, 4, 5 work week. You fly out on a Monday. You're somewhere else, Loop City, Nebraska, or Harrisburg, Pennsylvania, or wherever it was at a given time.

And then fly back Thursday night and then work from your home office on Friday. And we would, we both basically both get back to our empty apartments on Thursday night and have a beer and talk about, we were both getting pretty into craft beer. And it just started coming up like, man, there's just so many there's this obviously a problem.

Like, how do you know what's good and what isn't? And that was the original thesis. Like there's a discovery problem here. And the idea was, how do you help somebody like my dad? Who's been a local three union [00:19:00] electrician for 40 years and a Bud Light drinker. How do you help him find something that he's willing to take a risk on to try?

At the same time that you help someone like one of our Deloitte colleagues who drinks Bud Light limes and cocktails every time, but would never consider reaching for a craft beer, because he's like, I don't know if that's any good. What even is that? What is a, Double dry hopped imperial stout.

Is that going to kill me? Probably. And so the idea was let's make it easier to discover and you can rise the tide of the whole industry if it's more accessible, because at the time it was very inaccessible. The only real place to read about it was like Beer Advocate or somewhere that was, I think.

Jeff: initial magazines or message boards or stuff like it was very, it's a very insider baseball

Rich: Yeah, very inside baseball, very like in the weeds on little tiny specifics and terminology jargon that just the, if I said any of those words to my he would be like, I don't want that. And that would be the end of it. Like it just wouldn't happen. And so we were like let's make a thing that makes it easy to discover.

That was the initial thesis. And then the second thesis that was, Hey, this [00:20:00] can be a business instead of just like a cool thing is, breweries probably need help growing. There are these little tiny companies comparatively, they're all. Basically mom and pop startups taking up small business loans for the most part to start.

And then helping them grow because they're competing against and Bev and Budweiser and these massive companies that have multi billion dollar revenues and many multi million dollar ad budgets. And so how do we help do that? Turned out the first thesis was right. People really did want.

Help discovering something that was good. And I, like that took off. But the second piece is around the brewery is turnouts are just like wildly incorrect. And we learned, we honestly learned a tremendous amount. We were. Just about to give up and a friend of mine Melanie Gordon who had founded another beer industry startup called tap hunter.

Physically took the book, the lean startup out of her purse and hit me with it. She physically assaulted me with the lean startup. And then , I read it and something like two weeks later, we had our business that was much more sustainable. It wasn't so [00:21:00] focused on helping the breweries.

Advertise because they didn't need to, the industry was growing so fast. It turned out they really didn't need help advertising.

Jeff: Also, it's hard to sell things to a small cash strapped, low margin 

Rich: Totally. What a 

rookie mistake. That was a 20, 20, it was a classic 23 year old founders mistake.

Jeff: right. Looking at you guys, started the app and it grew really fast. I mean, I had operated a small company on the side in the industry for a while at this point. And you guys went from not existing to really existing, like really quick.

From a standpoint of, user growth, which I think is something that ports across all types of, products, whether it be consumer products like that or, whether you're selling, beer understanding and discovery or social media or anything else, like user growth is a huge goal.

What did you guys do? Like how do you go from zero to 50, 000 to a hundred thousand users in a fairly short amount of time?

Rich: Yeah, it was quick. I think it was, I think it was something like a hundred thousand users within the first year. And the first [00:22:00] 10, 000 of those came from the first couple of days. I want to say it was really the first few days was really fast. Yeah, i've reflected on this a bit because there really was the social media was really small comparatively back then It was really like facebook was just about it.

My space was dying. And facebook wasn't this sort of like world dominating thing that it is now There was no instagram or tiktok really anything. I think instagram came out a couple years later so it was really, there's a couple of things. First was we were solving a problem that we understood really well because we were solving a problem for ourselves and people we knew intimately well.

So we used to use my dad as a persona a lot and some of our Deloitte co colleagues as personas a lot. And obviously ourselves on the end of the sort of like advanced user to like brand new. Person spectrum. So that helped a lot. I think we spent a tremendous amount of time trying to understand like what is the problem that really makes it click for a person to be like hooked like immediately.

And we did, we designed the product around that. Like you log in and the very first was like rate a few beers that everybody has tried. It was like [00:23:00] Boston lager and Bud Light and like things that most people have tried a few kind of cool craft ones in there that, maybe someone like Bali blue moon or things like that.

And then , while we were developing that, we did an alpha test. So we took a lot of data and understand, not only took our experience with people in tons of conversations, we then measured it and improved on it with little iterative loops. And then honestly the big user growth in the beginning came from media.

So we very deliberately went after some media outlets like Thrillist was huge back

Jeff: huge back then. Yeah.

Rich: Yeah. And we networked our way to the folks that ran Thrillist and said, Hey, we're about to launch this thing. That's going to be extremely cool. We let them see the alpha and then we coordinated our open beta launch, which is like really our proper V1.

It wasn't even an app. It was just a website. And said, Hey, we would make, you would be the ones to announce it and work that out. So they tried it. They thought the product was cool. And yeah, when we launched, we did a quiet the day before to make sure nothing would explode.

[00:24:00] And then they did their big email blast and it was like 10, 000 users in two days or something like

Jeff: Nice. And then was it just viral from there, people seeing it out and sharing or?

Rich: Yeah, we did build a little virality into the product. And again, this was like really early days for this. I think back to, it's dude, everything does this stuff now. But back then it was like, we were so proud of ourselves for coming up with this. It was, rate and share.

And so we built integrations with Facebook and when Twitter started to grow and, things like that. And then that drove a ton of growth because people are like, Oh, what's that? I want to read your tasting notes, or I want to see what that thing was and click on it and make you sign up and things.

But for the most part, it was, Word of mouth. for that first couple of years, we really focused on building a thing that people would really enjoy using and keep their attention and come 

Jeff: So is it possible I could blame you for the trend of everyone taking pictures of their food now because people were sharing like what they drank

Rich: Man, possibly. I'm not to blame. I think we're more to blame for other things in the beer industry, probably than the [00:25:00] specific food problem. I think we definitely contributed to the like, always needing something new problem. I feel a little guilty about that. It's because that's a personal preference.

I'm addicted to trying new stuff. And I built it into the app to push for that. And then now clearly, it's but no, man, that was early Instagram days. Everyone was posting their food pics right out of the gate. That was like, 

Jeff: Yeah. 

Rich: was day one stuff. I think my first Instagram picture ever was a picture of a bratwurst I was cooking.

If I scroll back and check, I think it might be my first picture ever.

Jeff: It's great to see how some things change and some things just never ever change. 

So one more kind of quick question here is, you guys went into this market from a, looking at a market standpoint, there was, what equates to an 800 pound gorilla in the market when you guys entered, there was a fast follow right after y'all.

And in a funny twist of events, like the gorilla ended up falling down and being subsumed and the winner of the whole thing, and the one still operating going is the one that came probably fast fall on top of you guys. And they ended up acquiring acquiring the other thing the 800 pound gorilla.

But how did you look at entering this and going, [00:26:00] there is this giant incumbent, we can do it better. And then where do you think, maybe The other untapped may have had an insight or something that they were able to end up dominating that market.

Rich: And, I've spent a lot of time,

Up at night, wondering about that, Yeah. . I think in the beginning, the 800 pound gorilla problem, it didn't even seem that intimidating because we were just building a thing that was meant to be deliberately very different than that. Cause the thing that they did great.

And we looked at it and we were like, we're not trying to do that. That club is full. More people can come in really, but it's like a limited, your most extreme end. Of any space. This is actually a lesson I learned since then, and still think about in all kinds of product work today. If you're designing a thing for only the hardcore enthusiasts, your market is really small, really picky, really cheap, and like very difficult to serve.

I'm big into cars and that's a whole problem in the car space too. It's like the enthusiasts are. The pickiest and it's very hard to satisfy that because they're nothing is going to ever be good enough. So that was their market. [00:27:00] And we were like, no, I'm going after the great wide middle.

I want to go, I want to go help the regular people. So it didn't seem so intimidating there. The untapped stuff I think is really interesting and I've thought a lot about that too. They did come in right after us. They had a slightly different angle. It was all about check ins, which was just becoming like a big thing with four square at the time.

It was like a new idea and it was cool. It was super cool. When that app popped up, I looked at it and I was like, damn, that's pretty good. And so did Tim and, we mimicked a few things. Like we added check ins cause it was like an obvious and easy thing. I'm like, Oh, people want to check in.

Cool. We can do that. We can help people do that as they're rating their peers. But honestly, the big thing that changed was we were pivoting on purpose right around that time to move away from a model that in order to exist as a business, like we had all left our jobs. I quit Deloitte, Tim quit Deloitte, my co founder Shannon, who is in Wisconsin, our technology guy he had left his job full time.

And so here you have three people who need to live off of the business. We had raised some money, but it only gets you so far. We needed the app to, to be sustainable. And the that had started on [00:28:00] tap did not do that. They able to last in their day jobs longer. Whereas you could, we couldn't possibly be consultants and do this at the same time.

It was like totally impossible. And so we realized, Hey, there isn't really a good business to solve for breweries here. Like they're not going to benefit from this. There isn't something there. We to in person experiences, which we were very passionate about and did solve a problem. 

Jeff: you're describing a solve that I think , your business and mine both went to, at that point similar-ish timeframes.

Rich: Yeah, we did. And it made sense and it was cool and it worked. There was honestly, it was profitable off of that. It was a good business and a fun business and solved a real problem. Like all those things aligned. But as part of that, we honestly just stopped investing a lot of energy into the digital experience because it, it was only a piece of it.

Whereas on tapped, they went all in and they were like, we're going to make this the, an incredible digital experience. And they did. It's still really good. It's still going. I know. I almost downloaded it the other day and I was like, I got, I can't cause now I'm so out of the loop now.

I don't know what beers to buy anymore. Cause [00:29:00] all the labels have changed. I'm like, boy, if only there was an app for this,

Jeff: Someone should make that I, The history of your life it seems is you just go from one extreme to another. So you went back and ly was over and back to the, you know what I'll call, I guess like the mainstream startup world.

You went to a place called Startup Institute and I guess it's maybe that found what, the whole founder mode is big right now, but you founder mindset went from, directing partnerships and biz dev. It seems like over there to within a couple of years you were running startup Institute.

So off the bat, can you just explain to people startup Institute is?

Rich: So startup Institute was this magical little business that it was like they captured lightning in a bottle for a minute. It was basically the folks that founded it.

essentially invented the idea of a coding bootcamp. At the very same time, they, and some folks on the West coast basically independently and simultaneously came up the idea of a coding bootcamp, which was essentially a career accelerator. That's the word that I was using a lot in the beginning because the bootcamp term hadn't been [00:30:00] coined yet.

I was big on the career accelerator angle, but I guess it doesn't roll off the tongue quite the same way. So it never stuck. But yeah, it was, Hey, quit your job. If you're unhappy in your career and you want to go and do something you're passionate about, care about, could build a better career off of, quit your job, come to us, some unaccredited school in a conference room in Boston that you should totally trust, and we'll teach you a bunch of practical skills over a very short period of time.

It was eight weeks. It was two months. And then you go and you get a job and we'll try to help you get that job. That was the pitch in the early days. It was free So that helped but then it was wildly inexpensive, at first as well And and it was just brilliant because I went and they invited me to be a guest speaker early on When I was still doing Pythony stuff and I met the students and they were all Amazing.

I left the room teaching a class on biz dev and You Just was thinking about all the students, like the whole drive home was like, these people are crazy. They're so smart. They're so nuts. They all just quit their jobs. And they were so [00:31:00] passionate. And then I like, it just had its claws in me.

I was like hooked. I was like, I need to be a part of this thing. Yeah,

Jeff: I'm wrong, but I'm assuming you don't take someone and accelerate them from, join the company and speaking to business development to CEO because everything's going hyper smoothly. Uh, 

Rich: That's a fair guess.

Jeff: It's one or two ways, but but so I guess what, as you ascended there and ended up in that top spot, what needed to be done, like what were the big things that you were looking at and seeing and realigning the company around to try and drive, maybe the next step of success there.

Rich: Yeah, it had hit a wall because the early days, again, it was Wild West. There was, in the beginning, there was no competition. So people came from all over the world, literally, to come to our programs. They were flying from, five or 10 different countries to be a part of.

It was amazing. And all over the country. And then it started, you know, the barrier to entry was super low. Local versions of it, bootcamp started popping up in every major city in the world, certainly based in the U. S. But, there was ones that popped up in other countries too.

And [00:32:00] then the big competitors like General Assembly was the big one in the U. S. They went now out and raised a hundred million dollars. I think it was 92 million if memory serves. Some huge amount of dollars and some other ones raised 30, 40, 50 million. And we had raised single digit millions.

And so that was super tough. At that time to, to compete and find people who needed this experience, which was amazing. The outputs, the outcomes were incredible. The careers that people have launched, the guy that started Link Squares was one of the first Startup Institute students. These are people who have gone on to be like incredibly successful far and away.

But you have to find them and finding people is expensive. As every marketer will tell you very with sad, tired eyes. 

Jeff: I feel like that's a specific remark right now, but

Rich: it's hard. It's, it is. It's hard at acquisition stuff. So yeah, that was the big thing. It was like, Hey, how is this going to keep growing? Regulation started to be a thing. There was no regulation in the beginning and that was a whole piece to navigate. And so our CEO stepped down and she's an amazing woman, Diane Hessen.

She's like brilliant and inspirational. [00:33:00] And I joke, like I worked for a famous CEO. I worked for Diane. And I think the board was thinking at the time was, Hey, who knows how to sell stuff? Who has experience with product and delivering good experiences and getting people together and rallying behind a big goal.

And room looked at me and was like, that's sort of Rich's brand. Let's give it a shot. And I was about as different as CEO as Diane could possibly be. And I think they were like, let's try something really different. So the whole vision was let's keep the quality exceptionally high.

We cannot sacrifice that, but let's start working more B2B and solving the problems that businesses have around talent. And that was the big angle. Cause we were, we're solving a problem very well for an individual person. The person wants to come learn and then build a career, but businesses at the time, unemployment was super low, hard to find really good talent.

It's especially hard to find good talent in the high pace tech and startup world. That's like a whole different kind of person. And to de risk that talent, like hiring is really scary when you bring someone in that you met on the internet and talked to for two hours of interviews, like that could go really bad.

But with our program we had [00:34:00] partners that could get to know people over two months. And so the risk of that hire was massively lowered. So that was the thesis. 

Jeff: So again, back to, the problem there was a real problem and, it was worth solving.

So, 

Rich: for sure. But hard to do, you needed a bunch of money to solve it, that was the hardest part.

Jeff: yeah, I remember those days. Like it was, if you went to a couple, a short bootcamp and learn to code a little bit, you could walk out into a job paying, above six figures.

And there just, there wasn't enough people who knew how to code. It was wild. Building a company was predicated upon finding these hard to find people. And so just anything you could do to up the supply was incredibly a

Rich: and actually surprisingly, the biggest need was in sales. We had four tracks. We had web development, like coding. We had user experience, design, digital marketing, and sales and business development, and that sales track was like every, all of our grads basically were hired before they even finished.

Because they were good. And we taught them really well. I helped build a curriculum. So this guy, Alan Tellio was amazing. And these folks would come out just so much better than your standard new hire. But yeah, they were [00:35:00] like totally wild

Jeff: It makes sense. Like, how do you, what, how do you de risk, the scariest thing in the world isn't hiring always, it's hiring people directly out of college or with no experience in an area, because you have nothing to go off of, no references to talk to, you're just going off of like work ethic and do you think they have potential?

So anything you can do there to de risk that changes the math on it. So that's hugely valuable. You went from there, you ended up founding stack education, which I think at face seems very similar, but I think probably has some very important differences though.

What, assuming you didn't just leave for fun there. I'm assuming something was there. But is there more to leaving and founding this or is it just Hey, this is important problem to solve. And I have the itch to go be a founder again.

Rich: I super didn't have the itch to be a founder. I was so tired, man. Then we were, I was actually about to have my first child. My son, Richie was born basically the day we founded stack. So it's always easy to keep track of everybody's age and how old the business is. Yeah, there was a [00:36:00] really big opportunity that we wanted to solve that we felt an ethical drive to solve too.

So it was a little bit of a we're helping people that we know. You don't like need tons of help necessarily all the time. And we were looking at the higher education space and saying man, you've got like something like 60 percent average completion rate for college.

If you think about that's 60 percent or 40 percent of people start college, take on debt and then never get that degree. And now today we're seeing all the downstream effects of that with conversations around debt and student loans and all this stuff.

And so we saw this opportunity to go and help education, higher education. That was like really entering a tough spot just at the beginning of that timeline. And bring this kind of hyperpractical outcomes driven education to them. And my team, my leadership team and I were like very passionate about it and very capable for it.

And essentially like the board at SI just didn't share the same vision and how to approach it. I didn't really have faith that we'd be able to do a good job at it, which made me not want to do it. if it's worth doing, it's worth doing right. And it felt like it's not going to be right.

And so it finally just hit a [00:37:00] wall and was like, yeah, this, I think the vision is never going to align. So we left, I didn't actually intend to found it. It was a couple of months later, they basically reached out and they were like, Hey, I think we want to do this. Do you want to do it too? Cause I was just taking time off to, to basically try to be a good dad.

And then, yeah. And then we went for it and it was different. It was It was a different kind of program, all, all new subjects and in a bunch of cases too, and directly partnered with universities so the universities could offer it to their alumni and continuing education students and stuff.

Jeff: Yeah. No, I saw I went back, I dug deep and found some of the old voices of stack videos. It's cool to hear that. Like to your point, it really served a purpose , to elevate people up and help people, change the course of what they were doing and, markedly changed their career for a much more upwardly mobile setup.

Rich: It was super rewarding. It was like, there's still people on the street that if I see and remember from those times, like you feel emotion to see them because you're like, oh my God, I see your life and you're like succeeding. And I'm like, I love you.

Jeff: Yeah. 

Rich: Like it's amazing.

Jeff: On the scale of like problems, should we solve, you have [00:38:00] bring back T Rex is on the bad side and, help people get more educated and grow their personal and career and raise themselves up is probably on the very, very good side. Totally balances the fact that you made like the, beer app, they got people just obsessed with novelty.

Rich: did. I really did. I'm like forever spending my career trying to make up for that,

That uh, 

Jeff: is a 

Rich: transgression. 

Jeff: right

there, 

man. 

Rich: And now it's pivoted. It's cool. We've, we moved on from the educational piece and stack. Now we actually got into the healthcare space. Funny enough, right before COVID, we got into clinical trials.

And training people to work in that space and then COVID happened and it was like suddenly everybody's talking about three stage or three phase clinical trials. It was like never a sentence in normal language, normal conversation. And now we're building AI technology to help that industry to help the workforce there.

So again, we followed the, Hey, we're There is a problem to be solved. It's got its challenges to solve it. There's a bunch of issues in the higher education space, but hey, look at this, the academic medical center space. There's a huge opportunity around educating that workforce, which we still [00:39:00] do and using tech now actually help rise that whole tide.

Jeff: And you're still involved at stack, right?

So 

you're still engaged there, but you've through all of that, you have come out still engaged at stack, which is a hugely valuable and awesome, organization to be a part of. And then, you know, you have probably after almost 20 years of doing this, your first capital P product job.

Rich: that's right. It's the first time it's in a job title and it's a huge company. It's so different than the last 10 years of my career, but it's so fun.

Jeff: I feel like you have taken an all new approached the concept of founder mode where you just have decided to, not be a founder necessarily always, but that's where I think, hiring people like that is so incredibly powerful because you bring someone in, if you can apply that level of dedication and, like we said caring,

you can do a lot of special things.

Rich: I agree not to break my own arm patting myself on the back, but I think like there are, there's like certain roles that really benefit from having that kind of perspective. it's awesome. I've [00:40:00] gotten to build it on my team here. Like everybody on my team on the, we call ourselves the tech team.

The tech team here. They all really care. And we're able to share a perspective on all the different parts of the business which I think is one of the hardest things to do and succeed at in a product role, as I've learned is if you don't understand the effect of a decision on the marketing team, because you don't understand what marketing is doing, then.

You could cause a real issue. I'm fortunate that I've worked in every part of the business as an entrepreneur and as a founder, you have to understand all of that. And so my team has benefited from that too. And it's this like crazy high performing team that does not have to work at a frenetic pace.

Nobody's like losing their minds and pulling their hair out because we can approach problems deliberately and try to solve them. On purpose and go slow to go fast because we were already ahead of the curve a little on thinking what all the sort of downstream effects are for decisions. And we're not technologists first where we're business problem, business solution, people first, and the tech comes second.

So we generally avoid the tail wagging the dog problem a [00:41:00] 

Jeff: I And that, that's what I meant by in my mind, you've always been a product person despite whatever your title might be, because I think it's something that's helped. In my own career as well is you can be a marketer, you can be a salesperson, you can be a engineer, you can be in product being a product person just means you look at the entire system or you're looking at how it all works together for what's the big goal you're solving.

And if you can do that, you're going to accelerate in whatever you're doing. And if you

Rich: I think that's, I think that's a great 

Jeff: you're probably going to be, a little slowed for no matter what your title says.

Rich: I think that's a great way to put it. I think if product folks can think of themselves as entrepreneurs and broader business problem solvers, I think that's a path to success in my experience.

Jeff: Exactly. Cool. So I don't want to steal your entire day here, Rich. I could go on talking. It's been a long time since you and I cop. So I could go on forever, but come into the end of the show and I want to give you the rest of your afternoon back. So I appreciate you coming on, dude.

This is great to catch up next time you're in Boston. Let me know. We should actually meet up and say hello, for people who want to follow up , on [00:42:00] other things, maybe ask you about your favorite beer or how you grew or, how they can maybe contribute to, to stack. Where can people find you? What's the best place?

You said you're not really on LinkedIn, 

Rich: It's still probably the best place. You could find me on there. I can miss the message for two weeks and then reply and apologize. And I will mean it. And then say, Hey, sure. I'll be in Boston and we'll meet up. No, for real. Probably LinkedIn's the best. It's probably the best place to find me.

You could sometimes find me it uh, lingo, which is EF's bar on their first floor. Whenever I'm in Boston, I'm usually there. It's got a great craft beer selection and surprisingly good food. 

Jeff: Awesome. Cool, man. It's a pleasure having you on. Thank you so much. And let's not have it be so long before we talk again.

Rich: Yeah, for real, Jeff. Thank you so much. It was a total pleasure today. I really enjoyed it.