16 August, 2023

PowerUp Podcast | Episode 1 – Matt Crane MGMT Boston

PowerUp Podcast | Episode 1 with Matt Crane MGMT Boston

Special Guest: Matt Crane

Mike and Adam chat with Matt Crane of MGMT Boston about the differences between the startup scene on the West Coast and in Boston, what the Endeca effect is, and what’s next for MGMT Boston.

Follow Matt and the happenings over at MGMT Boston at mgmtboston.com, and sign up for the newsletter at mgmtboston.substack.com!

Stay in touch with the Tech Superpowers team and everything we’re up to over at tsp.me and on Instagram.


Podcast Transcript:

Adam Fisk: [00:00:00] What’s up everyone? Welcome to another episode of Power Up Boston, brought to you by Tech Superpowers, uh, where we connect with folks from the Boston Startup community to discuss the scale up journey. My name is Adam Fisk, and as always, we are joined by Michael Oh. Hello, and today we are joined by Matt Crane.

Excited to be here. So Matt, you came to know tech superpowers in a very interesting way, where you came and ran an event out of our space. So before we started talking through MGMT, Boston, your kind of latest focus, I wanted to spend some time really just starting with your background. Uh, you are a Boston guy.

You grew up in Boston, right? That’s right. I grew up in the area, born and raised. Awesome. So we have that kind of Boston pride here. Technically I am a transplant and Mike is a transplant. But kind of close enough all said and done. So, yeah. Why don’t you tell us a little bit about your kind of background.

I, I know you started out in like investment banks and, and the like. 

Matt Crane: Yeah, absolutely. So I came outta college in 2010, um, for Providence, which really enjoyed that experience and it was obviously an interesting time, right? The financial crisis had sort of, um, we were cresting out of it. At the time it didn’t feel like that.

It sort of felt like we were floating around the bottom. I was a finance major and it was sort of my dream to work on Wall Street like’s kind, what I had grown up in terms of this type of elite career, mergers, acquisitions, trading, stocks, that whole thing, like it just seemed very romantic and maybe romantics the wrong word, but it seemed like a high powered career that I sort of wanted for myself.

And, and obviously as, as we all know, what something seems like versus the reality of what the experience is like are, are super different, but. Coming outta school that that’s what I wanted to do. So I started actually at Bank of America in their private wealth group, which was a super interesting experience.

Got to work with some great people there. And you know, you sort of figure out how people build their wealth and mm-hmm. The learning from that is like a million different ways, right? All the different families that we worked with, there was no like pattern matching, right? Like everyone had a very different um, Way that they sort of came up or inherited, right?

So that was an interesting thing to sort of learn. And then I transitioned over to the institutional side of things at this bank called Pacific Crest, um, which is now part of Key Bank. And it was a really interesting sort of time and place to transition into. This was 2012 into 2013 because it was a software or sort of a technology focused bank.

So we were on the Facebook i p o, the Workday IPOs, and it was really the beginning of kind of like. This confluence of revolutions, you know, the cloud revolution companies that had web apps instead of on-prem. It was like just a lot happening from an institutional finance perspective, but also from a tech perspective.

And you know what I sort of uncovered through that process, which I think is like a great career learning that I talk a lot about with friends and and other people today, is that the best way to have a really impactful career is to be a part of an industry that’s rapidly growing, right? Yeah. And sort of investment banks.

We’re not right. Coming outta the financial crisis, technology had changed them a lot, but you know, software companies and tech companies weren’t. So that was sort of the realization that I got through that experience and that led me to pushing a bit of a reset button on my career and moving out to San Francisco with a friend of mine, my friend, my good friend, college roommate, Dale McDermott, and he was being relocated out there for his job.

So I was lucky enough to basically take all my stuff. Put it in his moving truck and then fly across the country and go out there to San Francisco and you know, start to try to break into the software scene out there. 

Adam Fisk: It is interesting to hear starting in Boston, starting and seeing kind of where things are and then following the Exodus almost to the west coast where everything’s popping out.

Starting to see that stuff like there. And I know with. Your journey out with the organization. You started out with them in San Francisco. You came in at a relatively low employee account. When, especially when we talk about scale ups, especially when we talk about enterprise, I think you were number 75, right?

Matt Crane: The 150, 170 fifth employee, the company had just raised their series C from Excel. The, the company’s name was at roll. And a few interesting things from that. Number one is like the company was growing head count really rapidly. So like things were breaking and you know, They were adding a bunch of functions, so I got to see that up close from a very junior employee standpoint.

Mm-hmm. So it was sort of like a, mm-hmm. Watch and listen as opposed to sort of act. And the other thing that was really interesting about AdRoll is it was, um, an advertising technology business. So we worked with other technology businesses or businesses that had websites, and you got to see how those business models ran.

So it was almost like an incredibly wide horizontal slice of the internet ecosystem. And then I got to witness because I was there from 2013 to 2015, that advent of mobile, which was super interesting because you began to see advertisers shift their strategy. Mobile apps were obviously becoming more prevalent and.

More important to the advertising ecosystem. And with that, you know, their business changed too and, and we really got to see that up close. So it was sort of in many ways my first platform shift and I got to see that up close and like that was an incredible experience. I can give a quick example, which is AdRoll at the time was one of the largest advertisers on Facebook’s exchange because Facebook allowed a lot of sort of advertising ecosystem partners to advertise on their web exchange.

Then when they launched their mobile exchange, they did not let any more external partners, none. So that platform shift happened. Facebook kind of took their share of ad dollars with them, and we got to see that up close, which was interesting to say the least. In 

Michael Oh: some ways when you’re in the technology world as much and as long as we have, you sort of see them, but it’s, it’s funny how you, you’re in a platform and you sort of.

There’s so many people that are in a part of that platform and it’s almost like it never was anything different years in the past or will be anything different years in, in the future. So it’s fascinating to take that little bit of that longer view. And I think another comment which you, which you made earlier, which I really love is, is that idea of like, if you wanna be successful, A lot of it is the race, not the horse.

Right? You need to be in a growing marketplace. You need to be in an, an area and industry that’s vibrant and you know, the, the, the whole sort of industry is sort of carrying you with you. And I think that’s a really key lesson for anybody who’s, who’s obviously trying to work their way up. 

Matt Crane: Yeah, absolutely.

And then that took me to Liftoff, which was a mobile advertising technology business. And that was super interesting too, because that was sort of at the beginning of the platform shift and I got to see that. We would work with advertisers like, you know, Uber and Hotel Tonight, like the original kind of mobile advertisers that we kind of wistfully think back of, of like the first apps that you used on your phone, the dating apps, like all of those early ones.

And then sort of saw how like almost the crossing the chasm journey of the mobile ecosystem in terms of then later working with the larger retailers like a Target or a Nike or a Walmart, you know, as that. Sort of ecosystem changed and more of those sort of like large, you know, legacy incumbent brands would come onto mobile and got to see that whole journey.

I was lucky enough to be the 20th employee at that company and sort of, we grew to hundreds of employees and then were later acquired by Blackstone. Um, went through a merger, like all, all this different stuff, and that was sort of the up close, like hands on the steering wheel experience of like what it was like to be inside a rapidly growing business.

And like thousands of learnings from that. Coming 

Adam Fisk: from my personal background where I’ve been with the tech superpowers team for 11 years. I was with Apple for many years and seeing how we have gone through our own kind of startup, our own scale up journey as we’ve tried certain things out, gone through that kind of, I guess, dealing with ambiguity cycle.

But one of the things that was most interesting in our pre-conversation before we recorded was the amount of bosses you had. In the amount of time you were with Liftoff. Right. I don’t know if you wanna speak to that kind of Sure. In your going through this process, things always changing and really being in that kind of prototypical founding team.

Matt Crane: Yeah, of course. A quick comment to that and then I’ll expand a little bit is everyone knows in a startup, or at least like a venture backed business, like the oldie constant is change. A lot is thrown at you. And I think, you know, one thing that I reflect back on is I spent almost eight years in that business and like it was a really great experience, but.

I spent maybe three to five hours with that team before I made the decision to join. Right? Like that’s an interview process. That’s pretty common. You invest these very small amounts of time to then invest a ton of time in your career. Looking back, you’re like, you know, I didn’t even know these people and I decided to sort of join.

You know, I was 27 years old, so like the stakes were pretty low. But it is funny, when you think back, you make these large career decisions and. I joined Harry, mark and Phil. So Mark Ellis was one of our founders and our C E O Harry Robertson was the C T o and Phil Crosby was the sort of head of product and two great technical founders and a business founder, like a very well-rounded founding team.

Very good people that like ran the business really, really well. And I was like, I was honestly, you know, proud to work with them and, and still, you know, enjoy their company immensely. But that was complete luck, right? Like I didn’t know that going in and I think going through different. Organizational changes, different people being the right fits at different stages of the company journey.

Like I had almost 10 bosses in 10 years in San Francisco between the two businesses at AdRoll and Liftoff. And I think what you learn through that is just like you have to have a steady hand understanding what are the must-haves to sort of survive in that world. For me, obviously it’s like good people and I think anyone would say that, but then you, you become a lot more discerning about sort of how to figure that out.

Later. Looking back right at the time, there’s a lot of luck involved and I think everyone who’s had some level of success has to understand that some of that just is luck. I think it’s fascinating ’cause 

Michael Oh: you have this [00:10:00] experience in, in a few different places. You’ve had that sort of eight, 10 years in the west coast and seeing, you know, essentially this, this wave of growth and these platform shifts and all these types of things like.

At the end of that period, other than, hey, there’s a lot of luck involved, you know, rolling the dice. When you say yes to an interview, were there any lessons or thoughts that you said, oh, you know, my former self eight years ago would’ve been really nice if I had known something?

Matt Crane: Yeah, I think the thing that I got right, which is important is like you wanna have an area or sort of enough responsibility end.

Space with which to like do really good work. So the pitch to me was like, we’re 20 people. You’ll be one of the first customer success managers and you get to own like a big part of kind of crafting what that role means for us. When you hear that, you should hear two things. One is like that could go really, really wrong.

And interestingly, the other first customer success manager, I found out on my second day that he was leaving, he was going to take another job. So like that was a little scary. But the positive of that is like if you sort of go in with the right attitude and. If it’s the right fit and if it’s the right people around you, then you can really grow your career much more rapidly than in a more established company.

And so you have to sort of like look for those opportunities and weigh them appropriately. And I think you’re, your weighing machine just gets better, right? Then you can understand later, okay, what is this industry like? Where are we sort of at on the curve? And you’ll never get it right, but you can at least sort of approximate better when you’ve seen that.

And you know, you’ll hear people say like, You know, you get to learn what good looks like. You know, you can sort of start to see talent calibers, you know, when you’ve had enough people you’ve interviewed or people you’ve interviewed with and like, those are just really important things that I think you have to experience.

It’s hard to get right at the very beginning, but those are all, you know, part of kind of the experience. You want to go into a place, and obviously it’s gonna be different for everyone in terms of like what stage of company, what industry. But I learned, um, and I stole this from Twitter where I steal a lot of great content that I read.

One of the first round Capital founders, his name’s Josh Koppelman, he said, when you join a startup, you’re making two betts. The first bet is that the company you joined is gonna be a good company and it’s gonna be valuable. But the second bet is that the market it’s in is gonna be big, valuable and important.

And you kind of need to get both right to have at least like the. Big time financial and career success. And that’s almost right, like three years ago, right? That would’ve been cryptocurrency or, or web three, you know? Now you might say it’s ai, but a year from now, like we could also be saying something different.

So it’s really hard to get right, but it’s important to at least say, like, refer back from prior experience to say, okay, where are we sort of at here and, and what are some distinguishing features of like this company that I could join versus all the ones that I can Google and sort of see their very similar websites online.

Yeah, no, I think that’s, 

Michael Oh: That’s very key. A lot of time, like you said, when when you’re going into these jobs, it’s three to five hours and maybe to a certain extent, you almost don’t really think that you have a choice. Right. You might have an offer that’s in front of you. Sure. And then the alternative is keep interviewing, keep finding stuff.

Right. And so I think it’s, it’s hard when you’re not doing kind of an A to B comparison, but you sort of a to who knows what to know exactly what happens. But I like that idea of sort of like, Being able to take, you know, some of that experience, find the things that are good, you know, the things that you, you’ve sort of picked out and sort of say, does that work within this job that they’re offering me?

And is this something that that gives me that potential to grow? 

Matt Crane: Yeah, and you can kind of go through like the old school business school competitive advantages matrix, but like if you just imagine that every industry goes through an S-curve of sort of like you could be too early, it doesn’t grow very fast, and then there’s sort of that rapid ascent and then it flattening.

I think it’s a really useful exercise to try to figure out, and you’ll never get it right, but like approximately where do you think you are on that curve? It’s, I think it’s just helpful to make better career decisions, but also, you know, try to figure out how to tip the scales in your favor to some extent.

Now, since 

Adam Fisk: being on the West coast and in San Francisco, you’ve been back in Boston for about a year kicking off M G M T, Boston, but I guess really the first thing to prime this is how are the two kind of startup communities. Different between Boston, between the West coast. I know everybody kind of looks westward to the Silicon Valley, to everything going on, maybe with rose colored glasses.

But since you’ve been in both camps, how are we the same? How are we different? 

Matt Crane: You know, the first thing that’s important to say is, you know, from a talent or quality perspective, what are the differences? And I, and I would say I can stand here feeling pretty confident that. There are not huge talent discrepancies between the Boston and the West Coast.

The biggest difference is size, right? You know, the West Coast is the largest ecosystem in the world, but what I said to Michael, which I’ll repeat again here is comparison is the thief of joy. And what you’re really looking to understand is if you want to build a career in technology, where are some places that you can build an elite career in technology?

I think the first answer to that is like maybe anywhere. Now, you know, now we’re in a remote world, but the second is in terms of Boston, can you build an elite technology career gear? And I think the answer is unequivocally yes. Like there’s a really deep level of, you know, investors here. Like literally the entire class from I.

Early stage angel networks to seed stage firms to Fidelity and Wellington, right? Like some of the biggest financial firms in the world, the entire lifecycle of funding. So that’s great. This is arguably the best medical town in the world. So in terms of biotech, which I sort of put aside from like just a core way or a category of things that I approach, but that obviously bleeds out in terms of there’s biotech, but there’s also great health tech companies here and you know what you might wanna call crossover companies in terms of.

Companies solving software problems for the medical field, like those are here. And then there’s just great software companies that solve consumer problems. And you know, B two B E SaaS problems. Like one of the criticisms of Boston might say, well, you know, there’s just not as many consumer companies here and the regular sort of person understands consumer companies, but Whoop is here and TripAdvisor is here.

So like that, right? That argument doesn’t necessarily even hold weight. It’s just a matter of like, I think we all as humans only have a certain amount of things that we can fit into our brain. And when you talk about tech, you’re thinking about Google and Facebook and Netflix, and those just happen to be on the West Coast.

And if you want to go deeper and understand like what’s in Boston, there’s incredible companies here and incredible people that have built their career here that have then moved, you know, out to the Bay Area to either be investors or you know, entrepreneurs out there too. So in terms of like seeding talent and getting great experience, you can for sure do all that here and.

I’m sort of proud to rediscover that coming back. ’cause that was one of my open questions. Like what’s the sort of, you know, software world like here? Is it really small? And the answer is big enough and it’s been great. And, you know, the people here are immensely talented and there’s serious horsepower in Boston.

For me, like the 

Michael Oh: one thing that I, I’ve always seen coming out of Boston is, This sort of vibrancy in youth that comes from these academic institutions that are these places where people really, really want to come. Right. And, and we’re talking not only across the the country but across the world. You know, m i t, Harvard, you know, there’s so many great universities, but also a lot of smaller universities, a lot of the universities that are focused on business and entrepreneurship and is an amazing kind of, you know, place and energy.

And then those people are sort of hitting the ground running in the professional lives. There’s a lot of ideas, startups, energy. I mean, back when I was at, at m i t, you know, it was the sort of the, the entrepreneurship competitions, the $50,000 to start your business, that kind of stuff. And I mean, that, that was like very early days.

But it feels like now if you have a good idea and you’ve got like the energy and the drive to do it, there’s gotta be so many opportunities to come out of school and try something out. Right? I mean, it’s like you have so little risk compared to, you know, I just turned 50, I’ve got kids, there’s so much on the line, I.

When you make a big business decision. But you know, when you’re in your twenties it’s easy to roll the dice. It’s like, ah, yeah, let’s try 

Matt Crane: this out. Right. One funny thing this, it’s silly that I didn’t know this, but like sort of when you graduated the world that you entered into professionally at least, and you know, we’re having this economic moment where things are a little harder in the funding world and you know, this sort of got a pullback and is it a recession?

Is it not a recession? And I ask like a five times c r o, who’s been through many different technology cycles. Hey, like when you guys ran a demo with your sort of on-premise solution, like how did you do that? And his answer was they had to travel to prospects, right? Like you had to get on a plane or a train or a bus or whatever with the laptop, with the software preloaded and show it to them in person.

So what people complained about sort of what, like how our things are. I think you have to remember how far we’ve come even in. 20 years, right? Yeah. The problems that you have are, you know, there are higher class problems than those logistical challenges of, uh, traveling Salesforce on a plane, right? You just need to send emails.

Adam Fisk: Yeah, exactly. The amount of vendor calls that I’ve had where it’s like we have four different people, not only on the tech superpower side, but the vendor side. Everybody in different time zone states, like locations, right? And then you get that email every now and then being like, Hey, I’m in the area. Do you want to like meet in real life and.

I have to catch myself every now and then be like, we could just do a Zoom call. It actually might be faster and easier if we did a Zoom call. I could fit that in. If you come into real life, we forget how far we’ve 

Matt Crane: come, Adam. Right? Exactly. 

Adam Fisk: Yeah. Uh, but to your comment and kind of teeing up M G M T Boston, in one of the previous Power Up Boston events that we had, there was a really interesting open question of.

We have a ton of talent in the founder of community in Boston. We have all these folks that are jumping out of M I T or Harvard or any of the other schools in the area, and they get their jump. They’re maybe starting out at like Greentown Labs and they get to the point where they have to start thinking of, well, do I just move to the West Coast?

Do I go to Austin? Is Boston too small for me? I. [00:20:00] The question was, well, what can we do to say no, stay in Boston? You have the community here. As you’ve started up M G M T, Boston, has that been one of those questions that you’ve been asking, not only the community, but yourself of. How can we make it so people don’t do the, Hey, I, I’m out to San Francisco for 10 years and I come back.

Matt Crane: Yeah, certainly. And I, I think there’s so many layers to that. We would spin up different work streams, there would be different initiatives to talk about sort of all the different things. Where I found in Boston, but I really think this is a universal thing, is that there’s different sort of ecosystem stages to a start B ecosystem.

There’s the early stage and like that can be early stage company and also just early stage industry like. People kind of hanging out with like no frills and, and that’s a lot more dynamic I think, anywhere around the world just because, you know, no one’s accomplished anything. Everyone wants to help each other.

And I think there’s, it’s just more natural. And then there’s the growth stage, which is like, we have a company, you know, we have employees, we have stakeholders. We’re trying to achieve a customer outcome. And you know, that’s a really great experience for an employee. From like a founder perspective, almost those two ecosystems are separate just because they have different initiatives of what they’re trying and they’re more siloed.

Where some of this came from is there’s definitely opportunities to connect the two, and as an employee, or better stated, an operator, and I can go into that, you are more likely to be in that sort of growth stage because that’s just where more employees are and you’re less likely to have the same type of exposure to the early stage.

You can learn so much from the early stage and you can contribute so much to the early stage. So that was definitely one thing that I, I was sort of focused on helping with. It’s really hard for just any individual person who’s busy with their job and their life, and that’s where the name comes from.

Like, you’re busy managing your life and your career. We wanna help you manage your awareness of like this great ecosystem around you. It’s hard to say, okay, I actually want to help out from an early stage perspective. Where do I go? There’s no answer to that. It’s an evolving stream of kind of like, Discussions, conversations, places, events, you know, all different things and, and it’s kind of different for everybody.

But yeah, where this comes from is like the employee or, or the operator, which is, you know, an operator’s, a decision maker, right? They’re someone who allocates resources, they’re. Working hard to motivate their team and succeed for their company. Like they do all these amazing things, but they’re employees.

Right? And that is just not as impactful sounding as it should be. So how do you unlock, you know, some of these people who want to get great career experience outside of their day-to-day without just switching jobs, right? There’s a great market for that. It’s called recruiting. And there’s, you know, plenty of job boards that run that.

And, and I, I looked at that and I was like, well, That exists. And I, I think it’s good to an extent, but if you wanted to just widen your aperture of an ecosystem to either help out, to meet people, to make connections, like, you know, there should just be a a another way to do that, that’s like a committed process or sort of an organization committed to do that.

And that, that’s kind of the mission that I set out to do, which is to help operators grow. Because at the end of the day, You can get so many great opportunities and like, let’s take HubSpot for example. It’s probably the most successful business out of Boston over the last decade and a half. You can only have so much exposure, even at the biggest business in terms of the problems you work on and the go to market model because it’s one business, right?

But if you had access to 20, you could still keep your job at HubSpot. Like how great would that be and how many more skills would you have and opportunities would you have over a longer period of time? ’cause you know, Again, it’s all about sort of building over the long term. Like that just feels like a more impactful experience for someone who you could call an employee, but really has all of this great stuff that they’ve been through that they can offer to more people to grow an ecosystem and did that solution 

Michael Oh: as you’re describing, which I think is amazing.

I mean in the sense that there’s so many resources that are oriented at early stage, at founders, at the people that are like trying to get investments and all that kind of stuff. And nobody’s really thinking about, I think the operators in, in this way, at least, certainly as, as I’ve heard. But is that something that, that came from your experience with some of these startups 

Matt Crane: on the West Coast?

Totally. I mean, this is the problem I’ve always had. You know, I came up through an organization and I love so much about it and I just love learning about other businesses. And I think lucky to work for a. Advertising business, which is works with other growth stage businesses. Like I’ve got a lot of great access to that and I just wanted to go deeper and sort of share that stuff.

You know, there’s a lot of great venture firms that do similar things. They have platform teams and they, and, and you know, one of them that I’d like to give a shout out here is underscore does an amazing job in Boston in terms of connecting folks across the ecosystem, but at the end of the day, they’re sort of limited in the, in the way that they’re in service to their portfolio.

And they just only have so much, so much time. But in terms of serving an entire ecosystem, it almost sort of needs to be an external group that’s trying to, to help with that, that doesn’t have the same type of constraints perhaps. And I think the other thing I would say is just that as a person looks to say, like advise a company, you know, you might think that those types of opportunities, or I’d say historically, those types of opportunities are gonna go to someone with a name brand because they’re sort of almost easier to find.

But if you’re designing, say like how to set up maybe HubSpot for the first time. That sort of like VP level person that you might imagine being so great, probably hasn’t done that in a few years. Right. There’s actually probably a person on his or her team, right. That has done it. And they might actually be more helpful to you as an earlier stage person.

So it’s, it’s almost like matching folks without saying, Hey, are you looking for a job? You should come over here and set up our HubSpot instance, right? Like, The best person at doing that probably isn’t looking for the job, but would love, love another way to sort of test their skills externally. And that’s sort of the thought process behind the model that we’re looking to build.

Yeah. And it’s collaborative 

Michael Oh: in the same way that maybe going to college is collaborative, right? I mean in the sense that like you, you think about having a job being siloed within that job. The interface with the people within that same organization, and I think it is quite easy to sort of slot in and not reach out to somebody that’s outside of like my immediate collaborators at work.

But you know, I think we’ve all had that experience in a college type of setup. I remember going to school and you’re dealing with people that are studying physics and I was in aeronautical engineering and it’s a really interesting kind of exchange of ideas. That actually is very hard to replicate in professional life.

And I, and I think what you’re trying to do is also kind of create these, you know, more coincidental conversations. Things where people are maybe inspiring each other. They’re looking for same, you know, solutions to certain things, but then also saying, Hey, have you ever thought of this because our business is very different from yours, but maybe this approach would work in yours.

Matt Crane: Yeah, and I think we all get stuck into like the early stage, the late stage and the growth stage. And it’s a seed round. No, it’s a pre-seed round. At the end of the day, a lot of these problems overlap and people want to sort of try to do different things at different levels of scale. And if you give them the opportunity to do that in small, medium, and large ways, like I think the whole ecosystem benefits and people’s career benefits in that.

That grows Boston. And I think, you know, when I thought about what’s the model here, it’s just fun to do it in a local community where you can bump into folks. There’s nothing, you know, maybe special about a geographic area anymore because like these markets are, they’re up above in the cloud, right? But there’s a fun thing about sort of building within a community that you are putting roots down in and a person that might live sort of 15 minutes away that you’ll see.

And I think there’s something special about that, especially after Covid like. To try to bring that back in a way is, it’s a fun thing to do, and 

Adam Fisk: to be honest, there’s the need to sometimes to have that space where you can commiserate, right? Where you’re in a room, you are kind of just hanging out, talking through and just going through the stuff that maybe really working or you’re hitting blockers and roadblocks on, and having that person that’s across the table be like, oh yeah, no, exactly.

I ran through the same exact thing. Sure it was different, but these were the 10 steps that we went through. You will probably only need three of them, but it’s kick-starting that brain of being like, oh, okay. I was too close to it. I was looking at the problem, and it was so isolated into this minutiae that really isn’t important in the grand scheme of things that that outsider perspective is just so, so important and like, It is really a thing that we, at least on the tech super power side, when we talk to our clients, a lot of our clients in wildly different industries and focuses are all having very similar stages.

Those growth paths where everyone’s gonna hit them at the same points generally, and the solution may be completely different, but talking at a very, very high level, sometimes that is incredibly helpful and. Honestly for us, sometimes talking to our clients and hearing them say, oh, this is what we are doing, and me just being like, all right, I’m gonna write that down quickly.

Maybe I, I think about that a little bit differently with our team and that, that ability to have that conversation. I can see it being, I. So, so valuable. Totally. So now one of the kind of big pieces that I know M G M T, Boston and you in particular had been focusing on, and I know when you and Mike first spoke, it was yet to be, uh, launched, but it is now here.

Is a big kind of piece called the Ende Effect. Why don’t you tell us a little bit about that? 

Matt Crane: Yeah, and I think it’s a great little microcosm of the ecosystem that’s sort of shown in a few different ways. So the first is in the fall of last year when I started taking notes around, okay, what’s this Boston ecosystem like?

And you know, what are some great companies to know? One theme, if you will, that kept coming up was the alumni network of this former software company called Adca. That sold to Oracle in 2011. What happened there? And sort of peeling back the layers on that, and I had kind of put in a couple different places.

The first was like the initial things I’d learned, like, seems like this is a great alumni network, you know, that you could sort of loosely compare to the PayPal mafiaa, just in terms of an analogy. I [00:30:00] won’t compare talent level or outcome or anything like that. But in terms of the analogy of sort of, you know, what these folks went on to do and then.

From there, the first company that I decided to profile was jellyfish, you know, incredible Boston area, B two B software company. You could call it Salesforce for engineering, but I’m sure if someone mm-hmm. Jellyfish was on the podcast, they’d do a much better, deeper job. And the founders of Jellyfish came from adca.

So I was like, okay, this is another great Boston area company or, or rather, the first one that seems super interesting. And these founders also had this formative experience and decided to work together again. Right. Which is. Which is a big achievement when you go through a large growth experience. And so I sort of called that out.

And then, you know, as I progressed through, I was really lucky enough to get in touch with, with a guy by the name of Jeff B and Jeff’s a really, really great, talented marketer who just started a new C M O job. But I caught him like in between sort of a few months off and we met for coffee and I was just like, Hey, I’d love to learn sort of about the story.

And we, you know, we got to chatting and I was like, you know, I’d really love if it’s possible to sort of pull out. This is, I think, something I just like to do informally. Like I always wanna know the why behind something, you know, the facts and figures of started in this year and acquired in this year and here’s what they did.

That’s cool. But like, what was everything behind that? We, we got to chatting and sort of agreed to collaborate on a series that was basically like, what did people from that time learn about cross section of things that’s applicable today. And we were really lucky enough to chat with the founder, um, Steve Papa, who was the c e o and sort of a, a host of some of the early stage folks.

Like just learn really cool stuff. And they had a lot of things that I kind of experienced in a different way, um, and to a much smaller degree than they have, obviously being much further along in their careers. But going through platform shifts, seeing what good talent looks like, seeing what good tech looked like.

And I think those learnings are really applicable to someone, you know, call them an employee, call them an operator who’s looking for a similar experience and wants to have a great career. But in terms of great companies and how they’re building things and. Then how you can benefit from that. And Deca isn’t exactly 

Michael Oh: like a household name, right?

I mean, compared to Facebook and Google. And I think to a certain degree, that’s sort of what we were talking about earlier, like Boston, I mean, people know of Oracle, right? And of course if Oracle bought them for a billion dollars, they clearly were doing something right. But when, when you run into people and, and you know, even, even I, as I was reading through it, I was, I was learning about companies that are clearly part of this Boston.

Sort of startup and scale up ecosystem and and have been successful. But to a large degree, these successes have been maybe less publicized or a little bit behind the scenes, you know, that kind of stuff. I mean, what are your sort of observations when you’re trying to kind of bring this into maybe the larger conversation about startups where people are sort of looking at more household names and pairing these things?

Matt Crane: Yeah, I think it’s a fair question and, and it’s hard to answer, right, because it’s sort of like the reality that doesn’t necessarily exist, but. I think the first thing I’d say, which is important is like the m and a ecosystem is alive and well in Boston. Like private equity firms and strategics are very active here because they know there are great companies being built here.

Right? And to that extent, like that maybe is part of the problem, right? Some of these companies get acquired before they can become these large, you know, multi-billion dollar platform type companies. And I think the really the answer to your question is companies need to make a commitment at the founder and team level, and obviously the team’s gonna change over to sort of reach that threshold like, State are going to be a big platform, like they’re going to go public and they’re going to.

Become like a tent pole ecosystem company. Like that’s so sort of a commitment that you need to make because you need to say no to some of these offers. And I think testament to HubSpot, they, they sort of said that they were gonna do that and they have done that. And you look at it today, like it has so much runway, it is a massive business.

Toast I think also should get a lot of credit. They’re building a massive business and they took those lessons from Endeca. I obviously don’t have the numbers in front of me, but like I think they’re serving like single digit percentages of restaurants. There’s a lot bigger of a market there for them if they can continue to make the commitment to grow to sort of that level.

And some of it’s luck too. Like for whatever reason, you know, mark Zuckerberg went out to the Bay area instead of staying in Boston, so maybe, maybe this whole conversation is different if he never left. And you know, there’s only a few, like a handful of platform companies per shift, per decade and those, those happen to be in the Bay Area from the last sort of 10, 20 years.

There’s only a handful of them. Right. So maybe in ai, like certainly Boston, I think will compete if, if that is the next platform that we all believe it to be, right. The fact of the matter, it might be just the math of it is, I think it’s long odds wherever you know, you are going to be. We have a 

Michael Oh: vendor called, uh, Meraki that was actually an M I T startup.

Um, and they were purchased by Cisco for a billion dollars and they absolutely could have done the full play. They could have tried to basically compete with the big guys. And it makes me think, yeah, I mean, as a founder and as somebody who’s kind of going through this journey, and, and if you have great success, you do have to make a choice, right?

Because you are gonna be getting these offers. You’re gonna get these big. Companies saying, yeah, here’s a billion dollars, here’s hundreds of million dollars. But it doesn’t happen to all of us, of course, but it is a matter of sort of committing to, okay, are we gonna be like HubSpot or do we just say, Hey, this is the journey we, we chose, you know, this is a great outcome.

Clearly it was, you know, for Sanji, the people in Meraki, To be bought out by Cisco and, and there’s still a tremendously great, you know, sort of product and we use it every day. So it is quite interesting how a lot of this comes down to intention rather than maybe circumstances or kind of like just what happens on the day.

Matt Crane: And the thing that I always like to say, which I think is important to remember when we talk about startups is startups are filled with people, right? That make technology and products are important and markets are important, but I’m at least, I’m a people first person. Like I think people drive these outcomes in.

You know, that’s just, could just be a people thing and not, not in terms of what’s in the water here versus there, but like people are the ones that, you know, make these big outcomes. And it is a small number of people that are kind of driving that. So it could just be a timing thing, you know, watch out for the next 3, 5, 10 years.

Like there’s no reason why that person can’t pop up in Boston or is already here. 

Adam Fisk: Speaking of one of the things that I think has stuck in my head the most in this piece is the concept of unreasonable things. And that was something that when I was reading through, Seeing the kind of term unreasonable things.

I was like, alright, I wonder where this is going. Is it the kind of negative focus of it, of people pushing against what is possible? But as I was starting to read, and especially reading the feedback from the team members, I grew to be like, oh, okay, so now I know what you mean by this. And I think is really, really important for operators, for individuals, team leaders, or just honestly team members themselves of sometimes the concept of what is currently unreasonable isn’t a terrible thing.

It is the kind of pushing for one step further and what really to me is the. Differentiator between that unreasonable thing being looked at fondly or not so fondly is trust. A in your operator, trust in your founder, trust in your team to be like, okay, I understand that the request of do this by this day on its face, no.

No, I’m not gonna do that. That’s, that’s not possible, but it is. Oh, okay. I actually, I do have the trust in the team. I have the trust that we can get this done and have that momentum. To be really just constantly moving forward was really a piece that I’m like, oh, okay. So when I’m asking my team to do X, Y, and Z, and I have that like internal guilt of, oh, Man, this, this sucks.

I know that they are already so overwhelmed and have these things to do, and I’m just popping one more stone onto the pile when that comes through, and that we see that success, that that celebration is so necessary, and that’s really what brings teams together and what brings people from Enda to jellyfish, from jellyfish to et cetera.

That was really, really impactful. Really powerful to read. 

Matt Crane: Especially from these, uh, these teams who have gone from A to B to B to C. Totally. It’s funny when you think about like a startup, right? It’s a very unnatural human experiment to throw a bunch of people together and say, we need to execute on this extremely unreasonable timeline.

Here’s a few million dollars to do it. You know, we’re gonna put the engineers here and the salespeople here, and they’re very different types of people and we all need to collaborate to sort of, you know, achieve this outcome. So it’s very unnatural. I think it is the first thing to say. The second thing to say is like, if you’re going to sort of do that, you need to be, I think, and this is, and I only really had, you know, 30 minutes with Steve Papa, who was the CEO and founder.

What I sort of heard about him in the background was that he really bet on people and he kind of was good at identifying talent and giving them the sort of like green space to go out and do unreasonable things. And I think what that comes down to in startups is like, You’re investing in products and markets and all this stuff.

You’re investing in people too. You need to give them the responsibility and space and sort of throw them in the water and maybe the deep end to let them surprise you and sort of make those asymmetric betts on people. In the same way that venture capitalists are betting on companies that are non-consensus, right?

You need to do the same thing with people, and I think if you find the right group and you sort of ask ’em to do things like they will surprise you because. Humans are really resilient and, and talented and creative. And you know, if you find that right mix, like that’s what it’s all about. Right? That’s the reason you’re in that unnatural experiment of a startup is to, you know, build those relationships, sort of forge through dashing to meetings and trying to mm-hmm.

You know, hip these deadlines. And I think the person who’s probably most well known for sort of like diagramming that culture as Frank Sluman at Snowflake, you know, his book Amped Up and you know, he sort of tests people to say, Hey, when do you think I can have this by? And you know it’s Monday and it’s like, I think I can have it by Wednesday.

And he’s like, well, what about later today? Right? Like it takes a special person to drive that pace to sort of ask about reasonable things, but then to have people sort of surprised to the upside, like that’s the whole point. 

Adam Fisk: [00:40:00] So you have completed the end cut. It’s been a great read. Honestly, that will be my plug for today.

I really will put it in the show notes, but please go through and read this. There’s a lot in there, a lot of really interesting. Learnings, uh, it’s the time to see what these people have already gone through. What’s next with M G M T, Boston? Where, where are you going next? 

Matt Crane: So, continuing to produce good media every week.

So bring the community, bring the operators, you know, that, that live and work here. Great startups every week for as, for as long as I can and as diligently as I can. And then I’m also launching, um, this summer, what I’m calling the MGMT, Boston Operator Community. Which is effectively a way to sort of put together that initial group that I sort of described before of operators in the ecosystem who wanna learn more about what’s around them company-wise, connect with great people who have that desire to grow beyond their day-to-day and wanna do that through a variety of ways and sort of help ecosystem build, help themselves, help the companies, maybe even their early stage companies around them.

Sort of figure out what else we can do to grow and help each other.  

Adam Fisk: Well, fantastic. I think the last question, which is the topical question of where startups, uh, should be focusing, maybe their attention, their efforts. We’ve heard a lot from various folks in the community that Twitter was at, honestly a great place to find that sense of community, find the folks in the Boston startup, even if they are.

Maybe Boston alumni, they’re not based at here anymore, but they still have that wealth of knowledge. There is the upstart. Now there is threads which launched with, which 

Matt Crane: has no discoverability, right? Like you can’t, it has nothing, right? There’s no homepage, there’s no search, but, but it is, all of your Instagram friends are also on threads.

Adam Fisk: You’ll come tell her, right? It’s there and the, the algorithm will serve you. The engagement is starting to crater in there, but where do you see the, the Boston community? Where do you see the, the startup community? Talking outside of the kind of in-person community building pieces, like what MGMT Boston is bringing?

Matt Crane: I think it’s good to start with like the indexes. So built in Boston is great for that. Like if you wanna sort of see the really wide swath of everything that’s here and that’s like all stages of companies. That’s sort, I’m. Our startups, our technology companies, or even just touch technology. I think that’s a great resource.

Uh, venture Fizz is like, if you’re looking for a job, you know, that just covers sort of software companies here. I think that’s a great platform. Boston o you know, the Beat is a great newsletter, you know, every, that comes out every day. Um, I gotta give a shout out to Abigail Reese, who writes Tech Deals Every two weeks.

It’s a roundup of all the funding announcements, um, which is hilarious to know that that is a script that runs. Off of form defiling. So founders, if you’re raising money, um, you cannot keep that private because unfortunately it is public, right? But she does a great job, I think, of reaching out to let people know ahead of time, shout out to Abigail.

And then I think the honest, like true answer is you have to make the effort to go out to stuff and meet people. I. I understand, I, I’ve got two kids, like I can’t even do that once a week anymore. But just even going to something once a month, like you can’t measure the sort of r o i that you get from those in-person stuff.

And, and a lot of it will be a waste of time because you just can never know. But like I think you get so much from putting yourself out there and going to stuff and meeting with people and, you know, telling your story and kind of veering introspectively from others. That that is probably the greatest way to sort of learn more about the ecosystem.

Really unavoidable. And if you’re remote, you know, reaching out to people on LinkedIn and just saying, Hey, I thought this was really cool. I saw this. I’d love to, you know, grab a virtual coffee or whatever. That works too. And I respond to all that stuff. That’s great. And, 

Michael Oh: and it’s great to have your time on this podcast and multiple conversations.

Thank you. That you and I have had, you know, one thing I mentioned on, on one of those is just I’m impressed by the amount of research that you’re doing to just keep on top of the companies in the ecosystem, but then the depth of research as you’re doing. The reporting that you’re doing and the, and the weekly newsletter as well.

So my hat’s off to you. ’cause even if it’s not going out to these events, you’re putting a lot of time into MGMT, Boston and, and we really look forward to kind of seeing what you cover next and events as well. I know that you are like us creating reasons and places for people to sort of get together for those coincidences, those kind of, uh, lovely conversations to happen.

And I think that’s, Another big piece. I mean, to me, I’m really optimistic about the Boston startup and scale of ecosystem. You know, it’s been 30 years of my professional journey has been always around this world, but I do love that you’re really trying to go beyond just the siloed company and then deal with your collaborators and immediate sort of work associates.

Let’s create more of that community assist each other, you know, on the small problems, on the big problems, maybe even company to company. These sort of conversations start to happen. To me, that’s really, I think where Boston can really thrive. 

Matt Crane: Absolutely. There’s a lot to do, so just gotta get after it. 

Adam Fisk: So that is all the time we have for this episode of PowerUp Boston.

I want to thank you again for listening to us, and we’ll be back at it soon with another fantastic guest. In the meantime, you can find everything that. Tech Superpowers is up to, and everything we’re about to be doing over on Instagram at @techsuperpowers and at our website tsp.me. In terms of plugs. Matt, where can we find you and everything you are up to?

Matt Crane: You could find me at mgmtboston.com or you can sign up for the newsletter.

Adam Fisk: Until we talk to you next time, from everyone over here at Tech Superpowers, we’ll talk soon. 

Matt Crane: See you.

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