5/7/26

Matt Gregory – Operations, Startups, and Learning to Ask Better Questions

Patrick Dyer Wolf (00:12)

Hey Matt.

Matt Gregory (00:13)

How's it going?

Patrick Dyer Wolf (00:16)

Pretty good, man. How are you? You were in a pushy mood yesterday. Are you still in a pushy mood or not anymore?

Matt Gregory (00:19)

Yeah, yeah,

No, I mean, I think I've been, ⁓ for whatever reason, served a lot of horoscope content on Instagram recently. And there's a lot going on for Libras right now. think ⁓ net, net, net, net, net, it's very positive, but ⁓ maybe that has to do with the intensity of my day yesterday. I'm also getting started with some consulting projects and stuff, so using different parts of my brain.

Patrick Dyer Wolf (00:49)

good it's all firing things are lighting up and all the quadrants I just had I just had a conversation well so I do I don't know what demographic I'm part of by doing this but I've been doing some asynchronous whatsapp voice memo messaging with with certain people including my friend Rachel from college and she she's she's sort of into the horoscope

Matt Gregory (00:50)

Yeah, it's all firing. Yes, yep.

Patrick Dyer Wolf (01:19)

insofar as it is an entry point into real discussion of the human condition and relationships. I guess I qualify that to say like she's not a kook, but like ⁓ I've got, I have a growing appreciation and we just went to a ⁓ dinner at my friend's house where the theme was like your star chart. Anyway, I got like a seven page packet about all my shit.

Matt Gregory (01:44)

Thank

Patrick Dyer Wolf (01:47)

So I could really dive into it if I give it a second. Right, yeah.

Matt Gregory (01:47)

that's cool. Like a little goodie bag. That's really

cool. Yeah, know, Heej and I have both been served this content and we've been talking about it more ⁓ because it's the year of the, is it like the fire horse? Which my son Will's big concern is if your horse is on fire, don't your pants burn? That's Will's concern.

Patrick Dyer Wolf (02:10)

I didn't know it was a fire horse. I thought it was just a horse.

That's my concern as well.

Matt Gregory (02:18)

You

know, pants and underwear. He's worried about both pants and underwear.

Patrick Dyer Wolf (02:22)

And do we know the answer? We don't know.

Matt Gregory (02:25)

So far I'm intact Yep. And you too.

Patrick Dyer Wolf (02:28)

good and if you

if you get burned off the horse you just get back on

Matt Gregory (02:33)

Just keep on ridin'. Yep.

Patrick Dyer Wolf (02:35)

Yeah.

⁓ Well, today we have a great guest on the show.

Matt Gregory (02:42)

You

Patrick Dyer Wolf (02:44)

This is like when Garth Brooks hosted SNL and was also the musical guest. I wonder how many times that's happened.

Matt Gregory (02:52)

Yeah, I didn't I didn't actually know that happened, but it does feel somewhat similar

Patrick Dyer Wolf (02:58)

say that as if it's fresh in people's memory. That was probably in 1998. don't know. Yeah. Matt, you're the guest.

Matt Gregory (03:02)

That was a good time.

Yeah, this is fun. I got kind of jealous because Pat had an episode and I didn't have an episode yet. So ⁓ I'm excited to be in the spotlight.

Patrick Dyer Wolf (03:21)

Yeah, we're flipping the table. Yeah, I'm a little nervous. So I should say that you always do a fantastic organizational job of coagulating thoughts and writing a very well-worded question list that you give to the guests in advance so that they can wrap their head around what we're going to be talking about. And then you guide the conversation. You steer the good ship.

Matt Gregory (03:23)

Little nervous. Little nervous.

Patrick Dyer Wolf (03:50)

But now, how's this gonna go? I'm out here flailing already. And I made some notes, but I didn't send them to you, I was too ashamed of them, and they were not organized.

Matt Gregory (03:56)

⁓ I f-

Yeah, well, I'm very happy to be here in any context. I don't need any pre-read. And excited to chat with you.

Patrick Dyer Wolf (04:15)

Okay good, because all my questions are gotcha questions. I feel like we should say that we've known each other for long time. We've known each other since college.

Matt Gregory (04:22)

dear.

Yep. Met in 2003.

Patrick Dyer Wolf (04:35)

2003, 23 years ago. And ⁓ it's been my pleasure to be doing this with you this past year or whatever, sort of like, it's just an excuse to hang out is the biggest positive for me. like, ⁓ you know, to get to talk about whatever, but also to get to about

Matt Gregory (04:37)

23 years ago.

Yeah.

Patrick Dyer Wolf (05:05)

talk about stuff that feels important and interesting and to kind of get to meet all these people that you have gotten to meet in those intervening years and before. ⁓

because your network is so varied and robust. It's just like, you know, we're only, how many episodes have we done? Eight, six, eight. ⁓ Already just like the breadth of the people we've talked to ⁓ has been amazing, you know, and in a related story, like I would say that you are probably the ideal person to host.

Matt Gregory (05:32)

We've published eight.

Patrick Dyer Wolf (05:53)

a podcast such as this, because just in reviewing your CV, your resume, it has been a winding and varied trail ⁓ of just like different...

⁓ Industries, places, I mean just a quick, to give people a little bit of a sense of the scale here, then you can jump in wherever you like. We knew each other in college. ⁓ I think you dipped a toe in some finance and the publishing world even, is that right? ⁓ You made your way sort of into the food space. ⁓

Matt Gregory (06:28)

Mm-hmm.

Patrick Dyer Wolf (06:39)

in a few different capacities. ⁓ And then also the baby food space. You've done some consulting. ⁓ You have worked in the respiratory health space at Sensory Cloud, which I didn't, maybe I knew but didn't remember that the FEND respirator was the Time Magazine best invention of 2020.

Matt Gregory (07:04)

Mm-hmm.

Patrick Dyer Wolf (07:10)

⁓ I didn't know this either. You were an innovator in residence at Tufts. You then obviously went over to the hair removal space at Nood N-O-O-D. Now are there rival Nood brands? It seems like there's a bra brand also Nood or is that related?

Matt Gregory (07:31)

There is another company that's called Nood ⁓ that I think is ⁓ like a bra, ⁓ like an enclosure, unrelated. Yep.

Patrick Dyer Wolf (07:38)

They're not related. Okay. ⁓

did this coaching program at Brown University ⁓ and received a certification. And you've started your own coaching business, and you started this podcast, Trail Map which we've been doing for the better part of a year now, I guess. ⁓ so you talk about a sort of ⁓ winding path. It's funny.

have a family book group which has read some ambitious things recently. ⁓ We meet on Zoom and we...

Matt Gregory (08:24)

Is this your

family that's in a book club or are these other families?

Patrick Dyer Wolf (08:29)

It's my family. It's me, Mary, her parents, my mom, her mom's best friend, her brother. It's another nice excuse to just hang out with your people that you like to talk to. ⁓

Matt Gregory (08:31)

that's nice. That's nice. Look good people.

Yeah.

And what was the word you

used? said, ⁓ intense, but, ⁓ ambitious.

Patrick Dyer Wolf (08:48)

Ambitious. So

we did like a bunch of Shakespeare was the like the the Henry ad not even like the fun ones. It was the history ones. I think it was a joint ⁓ Mary's mom and brother got together on this to sort of like think of something that could be grounding in these sort of trepidatious geopolitical and historical times.

Matt Gregory (08:53)

Good Lord.

Whose idea was that?

Yeah, sure.

Sure.

Patrick Dyer Wolf (09:17)

And I think it was that and it was also just like great brain exercise. You know, going. Yeah.

Matt Gregory (09:23)

Can we pause here just for one

second because I need, just while it's top of mind, I need to say that there are a lot of people that have been very supportive of us as we've been building the Trail Map podcast. But Mary, your wife's mom,

Patrick Dyer Wolf (09:40)

Mar-Margie-Margret?

Margie for short. Yeah.

Matt Gregory (09:43)

Margie ⁓

has been just top of that list. I'm so appreciative to her coming through with ideas for potential guests. Just her general like, well, I'll wake up every, you know, three to six weeks to a very thoughtful text from her, ⁓ you know, encouraging us on our way. And I just am very, very appreciative. So wanted to call that out.

Patrick Dyer Wolf (09:50)

100%.

100%, I'm right there with you and...

You know, she's one of one. I'm very grateful for her. Huge shout out to Margie, who we call Monnie because that's what the kids call her and now it's weird for me to think of her as anything else. she had, right. ⁓ But it's true, she's been so, ⁓ and not just supportive in like, ⁓ like she's really listened to the episodes and I think she enjoys it too, so. ⁓

Matt Gregory (10:21)

Yeah, that's how.

Yeah, yeah, it's weird how those grandparent names stick. They stick.

Yeah. Yeah.

Really nice.

Patrick Dyer Wolf (10:47)

Yes.

So in our book club with her and all those other family members, we recently read The Odyssey, which I don't know if you ever had to read that. I was supposed to read it in high school. I don't think I made it very far on my personal Odyssey. But like your resume here is like a kind of an Odyssey, man. Like you have, you've been, started in Boston, you made it out to San Francisco, you made it back. You've done, I mean, I didn't even list all the things you've done.

Matt Gregory (10:53)

boy. did, ⁓

Yeah.

Patrick Dyer Wolf (11:17)

and ⁓

Matt Gregory (11:18)

I actually

lived in New York City between Boston and San Francisco too for 11 months. ⁓

Patrick Dyer Wolf (11:21)

Yes, yep. See, I'm leaving stuff out left and right.

Do you, okay, so when we first knew each other in college, do you remember what you thought ⁓ you were gonna set out to do or what you wanted to do the most? What was your head space like at that time?

Matt Gregory (11:40)

That's a really good question.

I think, you know, so when Pat and I met in 2003, I had just finished up at a prep school in the Boston area called Middlesex. Shout out to Middlesex people. And, you know, it's a wonderful school, great teachers, very supportive community, you know.

super privileged community. We're in Concord, Massachusetts, just beautiful part of Boston area. And so for me, was a huge ⁓ step from that. Leaving Massachusetts, even if it was just to Connecticut, going down to Connecticut, Wesleyan felt so much closer to the real world than anything that I'd ever experienced before.

And so I remember in college, like putting a lot of my energy towards college ⁓ and not really, not really having much focus on career beyond that. ⁓ I guess with the exception of like, did do summer jobs ⁓ and I always, I was a kid growing up that like hated summer camp. ⁓ And it's somewhat ironic because I ended up

being a camp counselor and having that be one of my favorite jobs. being a ⁓ summer camper, I'd much rather just hang out with my parents and my cousins. And so that's what I did a lot growing up. But then once I came of an age where I could hold a job, I started working. ⁓ I think like, so that entrepreneurial bug was in me. I also grew up in a family where

There was lot of interest in entrepreneurship. My dad in his last chapter of his career ran the entrepreneurship program at Northeastern University for over 10 years and had an amazing experience with that. And then my grandfather was a venture capital guy who...

did venture, did VC work at a time when it was very focused on supporting cool ideas from entrepreneurs and figuring out how to give them the capital they needed to be successful. you and I grew up, you know, both my dad and my grandfather are important role models for me. And so I think I had that influence in the back of my mind. And then I had these summer internships and stuff.

But I remember very clearly, you know, spring of 2007 when we were getting ready to graduate from Wesleyan and Pat and I actually lived together in a, was it a quad?

Patrick Dyer Wolf (14:46)

Or was it five? Yeah.

Matt Gregory (14:47)

It was five of us, yeah.

And ⁓ I remember that we have some wonderful roommates, Jeff, Charlie, and Matt, all of whom went into finance. And I remember like ⁓ being like, you know, they were going to these recruiting conversations. And I don't think I was panicking about it, but

I was like, it's interesting. I'm not doing any of this, like, you know, recruiting or, you know, having any of these, these conversations that they are. ⁓ And I think it's because, you know, my parents growing up, it always sort of instilled in me this idea that like things will like work out and take their path. And, and so I didn't feel like a huge rush to like land that big job. ⁓

And so I think my career, this is a long answer to your short question, but like, ⁓ it's been like a, it's been very organic and it's been pursuing, there are definite threads, even if it feels like looking at it, my resume, there's, it's like all over the place. There are definite threads and it, ⁓ yeah. So I could say more about that, but that's where I'll leave it.

Patrick Dyer Wolf (15:51)

Great answer.

Yeah, I mean, can you draw one or two of the bigger threads that you've kind of followed through, or is that, we? Yeah.

Matt Gregory (16:21)

Yeah. Yeah.

Yeah. No, I mean, I think, ⁓ you know, I think that my first job out of school ⁓ was in wealth management in Boston at a what's called a family office or, you know, it's a ⁓ multifamily office. So they had, you know, probably under 100 clients. ⁓ And, you know, these are really wealthy families. ⁓ And I was doing client service work there.

And I think of any of my jobs, although I was good at it, there was a relationship component, and there was a project, a management component, which I was, think, naturally good at. My heart wasn't in it so much. And so I did that because I was like, oh, I graduated college. I must get a job. And then I think...

From there, think, you know, so it didn't really apply to this role, but I think to answer your question from there, the theme of like building things has always been the most energizing for me. You know, so I've followed that, that thread of building. Like how can I be involved with building things that I think are cool that like excite me?

Patrick Dyer Wolf (17:46)

Yeah, sort of ⁓ shepherding things, seeing them through and like in a multi-capacity sort of way. ⁓ And so, know, can you show us your footfalls in a couple of other places where you've helped to build something?

Matt Gregory (17:51)

Yep. Yep.

Yeah, so I ⁓ I worked, I also need to give a shout out to a company called Harvard Common Press, where I both had summer internships ⁓ in college and then I actually went to work there after finance, after wealth management. It was a small cookbook ⁓ and parenting guide publishing business. ⁓

You know, like there was, as with many industries, there's massive consolidation in the publishing industry. And this was one of like, you know, a few really awesome, you know, independently owned, owned by Bruce Shaw publishers. And, ⁓ you know, so I had an opportunity there to be part of launching parenting guides and launching cookbooks.

So that was my first taste of like this process this kind of multidisciplinary process of building new things ⁓ and The coolest feeling of like creating something physical like a cookbook ⁓ You know working with the cookbook author to do publicity like to figure out like okay, where can we send this author? You know on a publicity tour, you know

calling up radio stations to be like, could this author be on the radio show as like an interview guest? So like that was, and I was very junior at the time. like, so I was doing lots of manual and like lots of cold calling, lots of pitching. And that was an exciting process. And then I kind of,

⁓ Something that's been a big theme of mine in my career has been like, so I went from there to a company called Two Degrees Food, which was a ⁓ energy bar company with a social mission. So every bar we sold, like a Clif bar, we gave a therapeutic food product through Partners in Health to a malnourished child. ⁓ And amazing mission. ⁓

really wonderful team. And I ⁓ built a relationship with both the founders ⁓ who, yeah, anyway, another story, they, I'm still close with both of them and they built an incredible relationship. I think at the time, Will, one of the founders, know, he maybe he was 25 and the other founder, Lauren, he was, you know, in his, think.

late 50s, early 60s. so they built this collaboration. And I ended up going on to be their head of operations and help them build this business. ⁓ And a big part of that was building products for them. And so that's something that I've done a lot of at Two Degrees and then at

Plum Organics, the baby food company, and then at Sensory Cloud in Boston, and then at Nood. And now I'm doing it more on a fractional basis. And I can get more into building a product, what that means, but that's a big theme as you look at my resume.

Patrick Dyer Wolf (21:42)

Yeah. I mean.

Matt Gregory (21:45)

You asked for,

sorry, you asked for one, a couple of different like themes. The other theme that I would just throw out there is like education and mentorship as being another one that like is important to me and that I've looked for ways to find that. And yeah, we can talk about that more if you want.

Patrick Dyer Wolf (21:58)

Mm-hmm.

Yeah,

I think there's a couple different examples of that in your timeline.

I love the partnership at two degrees you were talking about, where it's like a very young and a more experienced person coming together to kind of like share those perspectives. It reminds us.

reminds me of when we were talking to Paul Tasner about just the different values that people of different generations and experience levels can bring. It seems sort of common sense to me, but maybe rarer than it should be. ⁓ Also, I think you briefly mentioned that your social mission was involved with Partners in Health, which...

Maybe some of you may know about that, and Paul Farmer, just an amazing guy, read the book about him at some point that Tracy Kidder wrote. Yeah, yeah. So, I mean, that must have been cool or interesting or fulfilling to be tied to that whole operation, too.

Matt Gregory (23:08)

Mountains Beyond mountains. Yeah. Yep.

Yeah. Yeah, I'll just say, mean, I think, I think one of the things I like about startups and small businesses is it's, you can, you can set out to do whatever you want. Like, you know, you could, you can, you know, and there's not, and that's why that's one of the reasons that I think Trail Map is exciting to me is like, I want more people.

to be inspired to go after things that excite them.

Patrick Dyer Wolf (23:55)

Yeah, I was gonna say another thread that's kind of occurring to me is that you seem to be, you seem to have gravitated to these relatively small operations ⁓ where you can be a proportionately larger piece of that operation and have like, not just influence, but like a lot of different influences and work with all of the important people who are really shaping what's being done.

Matt Gregory (24:17)

Yeah.

Patrick Dyer Wolf (24:24)

as opposed to trying to work your way up this giant ladder where it's a big ship and it's hard to steer a huge ship, ⁓ I think Jerry Seinfeld said at some point, it's like, I want to be on a surfboard. That's standup comedy, as opposed to making a movie. That's a big ship. ⁓ Does that seem like another thread? You're trying to be on an agile place that's doing something creative and you can be a part of that creativity.

Matt Gregory (24:28)

Yeah.

Yeah, yeah, yeah.

Maybe, you know, I think there's part of me that says, yes, absolutely. And then there's another part of me that I Plum Organics shortly after I joined the company, got acquired by Campbell's Soup. ⁓ And that's a huge company. And it was a really interesting experience because we were.

Patrick Dyer Wolf (25:17)

That happened while

you were there. So you were working basically as in for Campbells, but it was still intact kind of as itself.

Matt Gregory (25:20)

Yeah. Yeah.

for Campbell's.

Yeah. Yeah.

Well, it's I mean, now it's it it has been sold multiple times ⁓ by, you know, got sold by Campbell's to another company. actually not sure where where it sits now. ⁓ God. I mean, when I, you know, so I think. I guess I would say, yes, I've spent a lot of time in small like sub 10 person companies. You know, when I joined Plum, it was 40 people.

⁓ And it grew to be about 100 people in Emeryville, California. ⁓ And then we were acquired by Campbell's, which is thousands of people. ⁓ And I have to say, I liked the 40 person, the 100 person, the thousand person environment too, because instead of as a startup reaching out to a law firm and getting

build hourly, I could reach out to in-house counsel and not get billed that way. if I needed somebody who was a process engineer, I could go find a process engineer at Campbell's who could help me. I think the thing that ⁓

is, I mean, there's definitely more red tape, ⁓ you know, to get things done. And there's also a higher ⁓ bar in terms of ⁓ credentials that you need to get things done. But I'm not at all close minded to the idea of working for another big company. I think it just would have to feel like it was doing something that I was excited about. So, yeah.

Patrick Dyer Wolf (27:11)

It makes sense. mean, for sure,

there's going to be advantages and disadvantages to both ends of that spectrum, as you're describing. And as we've seen with a lot of our guests, like I was just watching the interview with Christina and talking about how she's essentially a one-woman operation right now, ⁓ coming from a bigger company. And it's great to be able to make your own hours. But then when you want anybody to pick up your slack, that's not going to happen.

Matt Gregory (27:15)

Yeah. Yeah.

Patrick Dyer Wolf (27:40)

You know, so it's just, but I think that's a good unifying thought that you have is just like, regardless of the size of the operation, like the overall mission has to feel worthwhile and exciting and, you know, worth being a part of. So. ⁓

Matt Gregory (27:53)

Yeah. Yeah.

Patrick Dyer Wolf (28:02)

I also wanted to explain that, you know, we've been doing this podcast for a while now and we had kind of, we've kind of been talking about the concept of it for like years, almost in like a.

Matt Gregory (28:15)

Well,

you're very humble, but I mean, this is Pat's idea. This podcast is really Pat's idea. On the record.

Patrick Dyer Wolf (28:21)

I mean, well,

the reason I bring it up is because I was never going to do it, but you made it happen. you know, you so like my idea was, I was calling it, what do you do? And it was because I don't know what anybody does in their job. And I wanted to have it a chance to just have, you like you, you do a school report about your family so that you can just like interview your family and actually like learn about their life.

And I was gonna do that for my but for you know friends and people I knew be like I know your job title Maybe from the internet, but I don't know what that means ⁓ And now you know this is for me. It's been a great like You're kind of opening me up to your world of all these these people with all these skills and experiences ⁓ and you you sort of have a familiarity with them from ⁓

from either working with them or knowing them in various capacities. ⁓ I think it ⁓ kind of works, I think, for us to be doing it this way because I don't know them from Adam. So I'm kind of coming at... Yeah. ⁓

Matt Gregory (29:41)

Why don't you explain to Pat what you do for work? Is that

the overall format of our show in your mind? That's funny.

Patrick Dyer Wolf (29:47)

Maybe, yeah. mean, you have

some idea, so you're able to guide it. I have no idea. I ⁓ think it's been nice to sort of like, just as you've been doing, taking us through your history, there for sure are common threads that people, especially people who are leading these kinds of careers have.

Matt Gregory (29:55)

I don't think that's, I mean, okay, sure.

Patrick Dyer Wolf (30:17)

regardless of whether they're a scientist or a chef or a landscape architect or somebody starting their own neck warmer business. I guess my sort of question is, are you enjoying this as much as I am? is it sort of just like, you, because I've been,

sort of surprised and delighted and ⁓ have you felt those things as we've been talking to all these wonderful people?

Matt Gregory (30:54)

yeah.

Yeah, I mean, I I have loved this and I'm so appreciative to you for, ⁓ you know, donating your time. To be clear, Trail Map is not a profitable endeavor.

Patrick Dyer Wolf (31:13)

We need some venture capital. Matt, can you hook?

Matt Gregory (31:15)

⁓ And we don't know if it ever will be, but I love the idea of building a ⁓ library of conversations with different people about their lives. And I feel like I've learned a lot from it. ⁓ And yeah, so I feel a lot of those same feelings as you, think. ⁓

⁓ Yeah, I mean, I think that one of the things that I really enjoy and I think I'm good at is getting to know people ⁓ and quickly learning. I think I'm a pretty quick learn in terms of quick study in terms of like, how does this role fit into the larger ecosystem of roles? ⁓ And that's kind of the way my brain works.

generally, I have a very process and map oriented brain. And it's consistent with the type of work I do too. I'm like, okay, how does this piece fit into the whole? Whether we're talking about launching a new product or what a specific person does for work. I think that Christina alluded to this too in her episode.

Being in product management has slightly different meanings depending on the industry that you're in. I would say that's kind of what I've done in the CPG space. It's different. Product management is different in tech. Consumer packaged goods, that's kind of what I've done. CPG, yeah. But I think one thing that...

Patrick Dyer Wolf (32:59)

what's CBG

CPG. ⁓

Matt Gregory (33:10)

is consistent with people who do product management is that they are very, generalists, they're quick studies, they like to put pieces together and that's kind of what I do. ⁓ And I think about in terms of like, I just did a talk at ⁓ my high school Middlesex last weekend on careers ⁓ and I was part of a panel with another

incredible recent grad, Steph Graham, who ⁓ we were talking about, you know, skills that are important, as you're setting off, in college and, we're talking to high schoolers, but in college and then, on your career. And one of the skills that I think is really important is being good at being a beginner, being good at like asking beginner questions and like really like, how do you familiarize yourself? I remember

⁓ When I joined Plum, one of my coworkers, Jen Brush, ⁓ I listened to her on the phone call. She was talking to a manufacturer of some sort of baby food and probably a manufacturer where she had no real idea how they manufactured. But I listened to the way that she presented herself and the types of questions that she asked and like the way that she like quickly oriented herself to

the way that the manufacturer worked. And I was like blown away by it. And I was freaked out because I was like, I don't know if I can do that. I was in the same role as her. was reporting to her. was like, I don't know if I can do that. That seems really hard. And I think it just takes practice. But as you get better at it, it makes it easier to like, to have any conversation and to sit, you know, and to try to really learn quickly, like who you're talking to.

⁓ So I don't know if that answers your question. I think it does.

Patrick Dyer Wolf (35:08)

I think it does. I mean, I think there's an element of just being present, which is sort of in vogue, but it's for a reason. I think hand in hand with that, what I was gonna say, sort of in talking about the origin of the show is just like in having worked with you on this for several months, you're probably the most professional.

Matt Gregory (35:12)

Yeah. Yeah. Yeah.

Patrick Dyer Wolf (35:36)

In a sense, in a communicative sense, you're very responsive, clear about what you expect and what needs to happen in a way that doesn't feel annoying or nagging or whatever. Just compared to the other emails that bop in I work in the music industry.

Matt Gregory (35:55)

I don't know.

Patrick Dyer Wolf (36:06)

Probably people are probably just drunk 24 hours a I'm just kidding. But going against the trend of everybody has a phone all the time, so you kind of expect people to flake out on you or just change plans at the last minute or something. ⁓ I think in addition to the ability to communicate with

different types of people that you were describing. I think you have this, I don't know if skill is the right word or whatever, like tendency ⁓ to just like do all the things that you need to do so that like the thing that needs to happen will happen and the person ⁓ feels comfortable and taken care of ⁓

And it seems simple, in the experience, like in my experience, it seems simple because like all the seams have been sewed up. But I think, I don't think it's that, maybe I just haven't worked, you know, I haven't worked in the type of spaces that you have, so maybe it's more common there. like, ⁓ just in my experience of the world, that's something that's relatively rare, those combination of things.

Matt Gregory (37:29)

Yeah, I mean,

thank you for saying that. That means a lot. ⁓ As I was preparing for this episode, I was like, this will be interesting. I wonder if like this will, how I'll feel. Like that makes me feel really good. ⁓ I think the interesting thing about that.

Patrick Dyer Wolf (37:47)

I don't know how aware of that you are, but that's really how I perceive you.

Matt Gregory (37:56)

is that's probably born from nerves, from like a nervousness or like an anxiety that... ⁓

you know, that's that's that is ⁓ managed by me through preparation through like, you know, and and born from nerves, I don't know that it's still as motivated by nerves as it probably was initially, you know, like it. I think putting myself out there like I have for my career is scary. It feels exposed.

It feels like you're exposed for what you know, what you don't know, and that's terrifying at some level to me. so I still, I I have a lot of nervous energy and my...

I mean, one of the areas where I'm really grateful to Heejin my wife, is that she is one of the most available, caring, supportive people ever that I've ever experienced. And she has a real...

She just has like a, she's just very, very good at being with people as they're feeling different things. Her friends, you me, you her family, like, I think she makes a huge effort with that. And so, you know, I think she's made it safe for me to, when I'm feeling nervous about a power dynamic or, you know, somebody that I need to interact with, can talk to her about it and,

that's been a huge source of support. And I think through the course of talking to her about it, I'm working on building the, know, the, ⁓ you know, internal fortitude where I don't need to rely on her every time I'm like up and down or whatever. ⁓ But, you know, I will say that, you know, part of putting yourself out there like that is about having an incredible source of... ⁓

safety and support.

Patrick Dyer Wolf (40:30)

Yeah, just like a North Star slash backstop, I guess. Yeah.

Matt Gregory (40:36)

Yeah, yeah.

I think ⁓ I don't like it when I get communications from people that haven't been thought through and that feel like, I mean, a good example of this is like dealing with really busy doctors sometimes. It feels like you get like a.

part of the information, not all the information. have to ask a question a hundred different ways to get the answer. ⁓ And so I think, you know, I think one thing that ⁓ I feel lucky for is that I'm, you know, my life is like, and a lot of the guests that we've had on the show are people that are in yourself, you know, they're people that are incredibly present people.

like that are willing to be open, be vulnerable. ⁓ And I just, that's the personality type that I'm most attracted to, so.

Patrick Dyer Wolf (41:44)

Yeah, mean, I'm sort of used to your communication style now, but at first, I mean, it's not like we weren't in touch before, but just not really in this capacity. At first, it was just such a like, my God, why can't it just be this way with everyone I deal with? And I will say in defense of doctors, a lot of them have a lot of, just a huge volume of stuff going on.

Matt Gregory (42:08)

No, no, no, no, no, I get that. I get that. I get that. I get that. I know you're married to a doctor too, so I don't... ⁓

Patrick Dyer Wolf (42:15)

But even people

who, the point is even people who don't have an overwhelming volume of literal things going on don't take the time to communicate well. An undervalued thing. I'm sort of curious if there have been points along this trail for you. I don't know if low point is the exact right term, but times where you were like, ah, I wish this could have gone.

different way or I wish I could have stayed here longer or I just I don't like how this ended or something to that effect.

Matt Gregory (42:52)

⁓ Yeah, good question. I ⁓ relatively few in my professional life. I feel that way more about college and earlier years. ⁓ I think that in my... Well, I think ⁓ I look back on Middlesex and Wesleyan and... ⁓

Patrick Dyer Wolf (43:13)

How's that?

Matt Gregory (43:21)

And both of those schools have so much to offer in different areas. And I think I felt.

I think I had a good deal of growing up to do at that point in my life and I didn't have maybe the confidence to really explore things that could have been interesting to me at that point in like a place of safety. so I have some regrets around that, like just like where I was allocating my

attention and energy ⁓ in college.

Patrick Dyer Wolf (44:05)

Yeah, I feel, mean.

Matt Gregory (44:07)

That might just

be the nature of growing up.

Patrick Dyer Wolf (44:10)

Maybe it is, yeah. I kind of, you know, just like thinking about...

that era of life, always sort of...

I don't know, know nothing is ever zero or a hundred but like I played a decent amount of sports in high school and I'm like, I should have done some plays, you know, or like something. It's like, why did I play all these sports? was just cause like it was cool at the time and I wanted to be cool, you know, like, and then, you know, look at.

Matt Gregory (44:26)

Yeah. Yeah. Yeah.

Yeah.

Yeah. No, I think that...

Yeah, go ahead.

Patrick Dyer Wolf (44:40)

No, was just saying, and then looking back, it was like, I didn't have to do that. Why'd I do that?

Matt Gregory (44:43)

Yeah.

Yeah, I think that the cool factor was important in the 2000s in school. I'm curious to see how that changes. Like we both have kids now. And my sense is from Will that like, I mean, my sense is that's changing a bit. So that's a good thing.

Patrick Dyer Wolf (44:55)

And like a

Big time.

I know, and it's almost come back, it's almost flipped on me. My son ⁓ does not have the immediate interest in team sports or whatever. sometimes that is frustrating to me because I want to share that interest I have with him. then I have to remind myself, that's cool.

He likes all these other things. It doesn't matter. And I agree with you that I don't think the same pressure is the same traditional gender role pressure I don't think is there in the same way as it even 20 years later, 30 years later. Sure, for sure.

Matt Gregory (45:54)

Yeah, I mean, I think some of it is.

But I feel exactly I can relate. We should talk more about that at some point, because I completely I completely agree. And I've observed the same thing.

Patrick Dyer Wolf (46:05)

Yeah, bonus content.

Yeah. I don't know if you have anything to say about this, but this thought comes up to me a lot whenever I dip my toe into sort of like various other areas of the economy. How do you feel about the amount of like jargon that gets used in the corporate world?

Matt Gregory (46:35)

Mm.

Patrick Dyer Wolf (46:37)

It seems like you have been able to harness it in your capacities. Do you have any thoughts about how people use? mean, even just like, going to your website, this is not a knock on you. I'm just saying, your website, Big Forest, Fractional Operations Leadership for Consumer Brands. I had to look up what that means. I didn't know what that means. No offense. Do you have any thoughts on jargon?

Matt Gregory (47:02)

Yeah, I

Yeah, I mean, I think it's a slippery slope. And I think if people are saying things that they don't know what they mean, that's a bad thing. I think within my orbit in consumer products, people know what I mean. And there's a shorthand.

⁓ that we use to talk to each other.

But I also understand why that's alienating to the rest of the world. ⁓ And I think ⁓ if I'm really tired in writing an email, I might lean into jargon more. But ⁓ I think using words to really making sure your words are precise and that you're explaining what you mean fully is an important thing to do. ⁓

a friend who's an IP lawyer ⁓ who I'm hoping to have on the show in a couple months. ⁓ And he is like a like master class communicator, like his emails, you know, because and he said to me like, actually, this is this is a this is a good connection point to ⁓ he said, you know, as a lawyer like his, he's really a teacher.

Like that's his primary job. And so he's teaching people about IP. I think like, you know, I think when I, like the way that I approach communication is, you know, through a lens of, you know, if somebody was learning about this for the first time, they could figure it out. You know, if there's jargon, they could figure it out. So, and I think that's like, there is part of me that's like this educator part of me.

⁓ that's coming to light there.

Patrick Dyer Wolf (49:12)

Yeah, I guess it's just, it's a matter of knowing who you're talking to and where they are. And I think, I mean, I should be a little more reflective in that there's every area, every industry has its jargon. Certainly the music world has its own jargon. And it's just, I think it just goes back to what we talking about earlier and being a good communicator, just like knowing whether you're making yourself clear in the

the right situation. ⁓

Matt Gregory (49:43)

Yep. Can I tell

people what fractional operations leader for consumer brands means?

Patrick Dyer Wolf (49:47)

Please

do, and you can turn this into a plug if you play it right.

Matt Gregory (49:51)

Okay, so right now I'm running a company called Big Forest, which was named by my son Will. ⁓ Yep. ⁓ And ⁓ Trail Map is a product of Big Forest. ⁓ Our other big product is ⁓ that ⁓ I do consulting. ⁓ And fractional means I'm not a full-time consultant anywhere. So I give somebody a company that I'm working with part of my time.

Patrick Dyer Wolf (49:57)

I didn't know that.

Matt Gregory (50:21)

That's the fractional piece ⁓ and then operations, know for consumer brands so operations for for consumer brands typically means anything related to ⁓ The way the business operates which is usually with a supply chain that goes out and produces products ⁓ It could include or be connected to quality assurance

Patrick Dyer Wolf (50:23)

Makes sense.

Matt Gregory (50:50)

It could include or be connected to finance of the business. ⁓ It could include ⁓ org, ⁓ like org design, like who's on the team, hiring, firing, job descriptions, all of that stuff. ⁓ And those are the big buckets, right? it's, you know, process, like the way the company operates. So.

Yeah, right now I'm working with my biggest client right now is a supplement business in Los Angeles called Innovix ⁓ And I'm their fractional director of operations for the next four months. ⁓ And so I'm helping them with all of those buckets.

Patrick Dyer Wolf (51:39)

So does that mean you have a four month contract which will be revisited or is that generally like you agree on a certain amount of time that you'll work together?

Matt Gregory (51:42)

Mm-hmm.

Yeah, I mean, think ⁓ it's four months. Not every contract has an end date, but that's what we agreed to. And ⁓ we kind of let it play out and see what happens. So, yeah.

Patrick Dyer Wolf (52:05)

Cool. Yeah.

Not to tie everything back to the TV show, The Bear, I just... We were talking about this TV show, The Bear, which some people may know ⁓ is about a chef in Chicago ⁓ who...

has worked at fancy restaurants in various places and comes back to run his brother's sandwich shop. And then when his brother dies, and then he turns it gradually into a nicer, nicer restaurant. ⁓

The fourth season, episode ⁓ seven.

the episode entitled Bears, which is the wedding episode. The character Richie comes to a realization, he's talking with somebody about a Zen garden and they're being rocks laid in various places and he realizes that he is the sand between those rocks. He's not a rock. He's the one who is the place for those rocks to sit and...

Matt Gregory (53:21)

Mm.

Patrick Dyer Wolf (53:26)

connects them and allows them to exist. ⁓ I had a really emotional reaction watching that episode because ⁓ it seems sort of like... ⁓

Matt Gregory (53:27)

Mm-hmm. Mm-hmm.

Patrick Dyer Wolf (53:45)

liberating, like I could feel that like maybe that is the thing that's okay to be is someone who allows, ⁓ you know, other people to interact and exist in the way, in the best way possible. ⁓ And, you know, I guess it's aspirational for me too, but I see, I can see parts of myself in that and I,

I see parts of all the things that you do in that. I'm curious if that resonates for you at all.

Matt Gregory (54:19)

It does. Yeah. I mean, I think it makes me think of the book, Artist's Way, ⁓ because ⁓ something that I know Pat has begun reading, my wife, Heejin, is in the midst of, ⁓ And I think one of the pieces that the author ⁓ points out is that, you know, everybody has

a creative artistic side. ⁓ And that side can get blocked for a whole variety of different reasons. ⁓ And ⁓ I think... ⁓

I think that being the sand between the rocks is definitely an important role. And I think you can build a career doing that. You can build a life doing that. But I do think it leaves a certain amount of stuff on the table, which is your own output, your own uniquely you output. And I think I've...

I started feeling that like an itch ⁓ about probably five years ago. ⁓ And I even remember articulating it to the founder, David of Sensory Cloud. said, I'm loving helping you realize your dream of launching FEND and all that stuff, but I want my own dream. And he is a professor too. And he...

Patrick Dyer Wolf (55:57)

Nah.

Matt Gregory (56:02)

kind of coached me through it. And he was like, you'll get there, you'll find it. ⁓ And I think that like for me, Trail Map has been a real exercise in, even though I'm facilitating the conversation, you know, that of somebody else's life and path, like it feels like something that I'm creating. So it's like, you know, and I think I feel unblocked in a way there that I haven't.

ever before. ⁓ And so I, you know, I think a lot like I'd really like to write a book at some point, I'd really like to do more talking, like speaking. I, you know, maybe, I think there are lot of things that like, and maybe they're maybe they're not even professionally aligned, like, maybe it's doubling down on that sourdough. ⁓

you know, ⁓ bread baking ⁓ hobby or, you know, something like that. Yeah, pandemic vibes. But I think, you know, as I think about Big Forest and what it stands for, I think, you know, ⁓ you know, a collection of activities that help other people get unblocked, help them do their best work. And then, you know, I think ⁓ in doing that,

Patrick Dyer Wolf (57:04)

Yeah.

pandemic vibes.

Matt Gregory (57:30)

Create my own things ⁓ so I think that's that's my answer

Patrick Dyer Wolf (57:37)

Yeah, think you're in a good spot now for being able to blend, I mean, you're kind of saying that, but blend being the sand and being a rock. And I think the ideal scenario is where ⁓ you're able to alternate and sometimes be both at the same time. ⁓ So I think, you know, mean.

Matt Gregory (57:45)

Yep. Yep.

Patrick Dyer Wolf (58:04)

It seems like ⁓ all of the threads that we were talking about are still existent and going on in these things that you're doing now.

Matt Gregory (58:16)

Yep.

Patrick Dyer Wolf (58:17)

Do you feel like your college, high school self that was sort of like head down and focused on school, what's your conversation with that self? Is that self stoked now? Are you?

Matt Gregory (58:42)

Yeah,

I think so. think so. think ⁓ the conversation that I have with my wife sometimes is like with the skill sets that I have, like ⁓ are there other things not related to consumer products or other things that I'd like to be doing, you know, that would be energizing to me. And I think college is a really uniquely good

time to try a huge variety of things at a low risk, like when you don't have to really think about how you're using your time. ⁓ So like, for instance, know, Wesleyan had a huge film department, like I would have loved to take some more film type classes ⁓ or. Yeah. Yeah, well, I mean, that's that's seriously like one of the.

Patrick Dyer Wolf (59:31)

We could make the podcast more cinematic. could start doing more work on my lighting.

Matt Gregory (59:37)

You know, I don't think there's any reason we need to keep it a secret. Like, I would love to, from an editorial perspective with this podcast, get to a place where we have more like B-roll and more documentary type footage of, you know, the go on site. You know, if, you know, when we do an interview, if like we, even if we film the interview like this on Riverside, like I'd love to go visit the person and do like...

a tour of the thing that they're working on and show that and have that be, and I think it could be really compelling. yeah, that's all in the works.

Patrick Dyer Wolf (1:00:17)

Let's do it.

we've made some references to your family, but you have wonderful wife, Heejin and awesome son, Willy Will, is he going by Will now? Or Willy? Willy, okay. ⁓ And ⁓ how are they, first of all?

Matt Gregory (1:00:39)

He's still going by Willy.

They're doing really well. Heejin is, I think, excellent artist and is a really great mom, too. Has put a ton of energy into being an incredible mom for Will. I think Heej has done a really good job of

Patrick Dyer Wolf (1:00:55)

Excellent artist, by the way.

Matt Gregory (1:01:16)

building a community for herself in our town in Brookline. She has a lot of really nice friends that many of whom she's been nice to share with me too. So I feel good about that. And then Willy, he's in second grade at the public school near us. And he has

some big interests in Lord of the Rings, Star Wars, in ⁓ Harry Potter. And yeah, so he is very much into the fantasy books like his mom. ⁓

Patrick Dyer Wolf (1:01:57)

the heavy hitters.

were watching the first Lord of the Rings movie and the the rider, the horses, what are they called? know, the kings that were killed by the former ring holders that are now like these shadow riders. I sound like an idiot right now. That was too scary, especially for Nellie. So we're gonna have to come back to that.

Matt Gregory (1:02:10)

Yeah. ⁓

⁓

Yeah, Yeah, ⁓

Patrick Dyer Wolf (1:02:36)

Yeah, number four, it's real.

Yeah, there's only a few scary parts in that. I don't feel like we've really nailed down what a good cook you are and how many of your, like a lot of the stops on your journey have touched on food, but I think they don't really do justice to the amount of culinary experience and expertise that you have.

Matt Gregory (1:03:14)

thank you. don't, I mean, I do enjoy cooking a lot ⁓ and love talking about food. love going out to restaurants ⁓ and I'm trying to get better at, I think you asked earlier about things that ⁓ I might've done differently or regrets or whatever. I think one thing is, especially like early in my career boundaries were very hard for me to establish with work.

and I think the first thing, ⁓ and I mean, again, like Heejin Heejin's, been immensely patient, ⁓ with this. though I know it's frustrating to her. ⁓ like there were a lot of times before we, you know, had will and before we like had real responsibilities where I would spend, you know, weekends working, ⁓ versus like going to explore whatever.

⁓ or cooking ⁓ and I think I'm

Patrick Dyer Wolf (1:04:19)

But you would spend weekends

cooking or you'd spend weekends working instead of cooking? Instead of cooking. yeah, yeah.

Matt Gregory (1:04:22)

Working instead of cooking. Yeah.

And so I think I'm getting much better at the boundaries stuff with work and finding times and realizing how much cooking and shopping, like I love going to the grocery store. ⁓ I was at Whole Foods ⁓ near our house a couple of weeks ago and ⁓ Chris Kimball, who's the ⁓ guy behind, he started America's Test Kitchen. And now he has Milk Street.

Patrick Dyer Wolf (1:04:49)

yeah.

Matt Gregory (1:04:52)

was there shopping too. Yeah, I don't like, my god, this is crazy. ⁓ I didn't say hi to him. I should have, but I should have. I really should have. But I think, you know, I love cooking and I also generally ⁓ struggle with social media. ⁓ Like I just don't know. Well, but except for

Patrick Dyer Wolf (1:04:53)

He was there? Wow. That's where the magic happens. Ah. Regards.

No, that's cool.

Well that's fine, social media sucks.

Matt Gregory (1:05:18)

Instagram videos around cooking. Like I think that like, you know, it's it's really inspiring. ⁓ And I've gotten a lot of good recipes that way.

Patrick Dyer Wolf (1:05:21)

That's true.

I shouldn't say it sucks, because that's a cranky old man, broad brush thing to say. I want to give a shout out to my wife, Mary. Her social media digest on both Facebook and Instagram, her entire meta digest is somehow the most wholesomely curated digest I've ever seen. It's all stuff that's useful to her life. No filler. All killer, no filler.

Matt Gregory (1:05:29)

No, no. It does suck. It does suck.

my God.

It's so wild that you're saying it in those words because Heejin's the same way. She's like, I feel like I have just defeated social media and all I get is cooking, parenting, know, like just wholesome stuff. And I open my thing, maybe it's just being a guy. I open my thing and I'm like, my God, this is horrible.

Patrick Dyer Wolf (1:06:01)

Wow, okay.

Yeah.

Yeah, probably.

I mean, you click on one boobs and you're cooked, you know? But she follows this mama docs travel, like doctors who are moms who travel, and gets all sorts of advice. And she participates too in other doctors' questions and then has useful things to say. The comment threads are actually useful. Unreal. Unreal to me.

Matt Gregory (1:06:29)

Yeah. Yeah. Yeah.

Yeah, yeah,

yeah, so it is, it just, just know folks, it can be useful if you, if you it correctly.

Patrick Dyer Wolf (1:06:51)

It can be, yeah.

still in its early state. mean, you know, people are like, this is the world we live in. It's only been a thing for like 10 years. It's crazy. Maybe we'll figure it out. Maybe, maybe.

Matt Gregory (1:07:00)

Yeah.

I think, unfortunately, incentives are not in the right place.

Patrick Dyer Wolf (1:07:11)

They rarely are though, I don't know.

Matt Gregory (1:07:14)

Yeah, I'm not sure. that's funny that you say that about your wife, because that's exactly conversation Heej and I have all the time.

Patrick Dyer Wolf (1:07:24)

Yeah. Well, Matt, thank you so much for joining us on the Trail Map podcast. Can we do a post-show wrap-up like we normally do? But...

Matt Gregory (1:07:31)

This was fun.

Yeah, let's do it. Let's do it.

You

Patrick Dyer Wolf (1:07:42)

I thought that was a good episode. hope it wasn't too scattershot. tried to tie it together, I hope you...

Matt Gregory (1:07:43)

That guest is full of shit.

No.

It was great. It

was a great, really helpful conversation. I appreciate you taking the time ⁓ and the thoughtfulness around it.

Patrick Dyer Wolf (1:08:05)

I mean, you know, it's easy to do. It's easy ⁓ to reflect back what you see in front of you.

Matt Gregory (1:08:11)

Yeah. Yeah,

so. ⁓

What's

I'm brain dead.

Patrick Dyer Wolf (1:08:24)

You

⁓ We have like, so you're like, think working on like three or four other episodes right now that we've recorded. I'm stoked for those.

Matt Gregory (1:08:36)

Yes, I have two

Matt Gregory – Operations, Startups, and Learning to Ask Better Questions

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