Greg Segall

Being CEO of your company can be very challenging. Showing great leadership skills, uplifting your team, and at the same time, managing the company well. Nevertheless, being the head and voice doesn't mean that you have to carry everything by yourself.

Today in The Frame of Mind Coaching™ Podcast, I have the pleasure of coaching Greg Segall, CEO & Founder of Alyce, an amazing personal gifting platform, perfect for finding presents for prospects, customers or employees.

In this episode, Greg and I discuss the steps and processes necessary for having and maintaining great team communication,  how to encourage them to be part of the conversation and how to stop eating rotten mangoes.

If there's a challenge you'd like to talk about on the podcast or privately, please reach out to me at:

Episode Transcript

Kim Ades: [00:00:05]
Hello, hello. My name is Kim Ades and I am the President and Founder of Frame of Mind Coaching, and I want to welcome all of you to The Frame of Mind Coaching Podcast, where we invite guests from all over the world, leaders typically, to come onto the show and get coached live and in person.

Today, I want to introduce to you, my guest. His name is Greg Segall and he is the President and CEO of a company called

Greg, welcome.

Greg Segall: [00:00:35]
Thank you. Nice to be here.

Kim Ades: [00:00:37]
So first, where are you located?

Greg Segall: [00:00:39]
I am in Boston, of all places. No snow on the ground, thankfully.

Kim Ades: [00:00:43]
Boston without a Boston accent.

Greg Segall: [00:00:46]
Well, originally from Connecticut, so... Connecticut folks talk fast. Boston has, you know, the obvious accent, but I would say most people in Boston don't have a Boston accent. So.

Kim Ades: [00:00:56]
If you were Canadian, you would disagree. But anyway, tell us what is

Greg Segall: [00:01:03]
So, Alyce is a B2B sales and marketing platform for enterprises, and we use gifting as a way to connect with people and get to know them. What we call the five to nine, which is anything that's not your nine to five.

So we use gifting as a way to be able to invest in relationships with people. And that is one of the top ways that you can show that you have appreciation and build reciprocity and, you know, depth of those relationships as you're going into it.

Kim Ades: [00:01:31]
So can you be more specific? Are you talking about giving a gift to someone who's already your client? Or are you talking about giving a gift to someone that you want to... A prospect, for example.

Greg Segall: [00:01:43]
Yeah, it's more... We focus much more on the prospect side of things where it's much harder to actually build rapport. So if you think about it, you have a million different people that are trying to sell the same types of products, technology has become fairly ubiquitous, you know, as a whole and, you know, sending a gift to somebody, and basically showing that you value their time is insanely powerful compared to the same 70 million sequences and emails and cadences that people are getting.

I mean, I'm sure your BS meter is up to here and seeing that somebody is actually just trying to throw you in some sort of a template. So this forces somebody to think more about who the person is. You know, Alyce is able to figure out who they are in their five to nine, and then we use that as a way to power the gifting experience in the investment experience.

Kim Ades: [00:02:25]
So I want to know a little bit more because I'm very curious about this. So, how would I identify a good gift for someone? And then, would it be a campaign? I'm giving the same gift to all of these people who are in the same role? Like how would it work? For example, let's take me as an example, right?

Greg Segall: [00:02:42]

Kim Ades: [00:02:43]
So, I run a coaching company, presumably I want to get to know people, VPs of HR. So do I select one and really get to know that one person and send them a gift? Or do I send all the VPs of HR some cool HR e-gift?.

Greg Segall: [00:02:58]
No, everybody is an individual person, right? You're not a persona, right? You're not like Kim, the coach... Or the coach. You're Kim, the coach, right? And you have your own perspective and your own individuality, you know, that's around that.

So the whole base of Alyce is to make sure that you're building one-to-one connections at scale. So it does all the hard work for you. So it's able to figure out who the person is, it's able to figure out what they're interested in, and then we have a marketplace of 30,000 products in there, right? And those are all experiences and, you know, could be gift cards, could be physical products, all types of things that we've highly curated, that are things that people want, like B to C products.

And then you're able... The system's able to pick out an individual gift for each one of those people. You're able to type an individual message, send that off to the person. And then, the beauty of Alyce is that we don't send the thing to you.

Like, how many people have sent me, like chocolate? I'm, like, a gym nut. I don't eat junk food, you know, at all. And yet that's the same thing. Or people send me things for like golfing events. I don't golf. I'm a baseball guy, football guy, you know, a basketball guy that's there. So that's what it does.

And so when the person gets the gift, we call it an invitation; then the person can either accept that invitation. They can exchange for anything else in the marketplace, right? Typically around 2,000 to 2,500 options per price points, or they can donate the value to a charity of their choice.

So you'll see many times, I think we're probably close to about 15% of people end up donating, you know, the gift value to charity.

So, Alyce was founded with a double bottom line at the beginning of the business. Like how do we make sure that giving experience is really amazing between two people? Like, you're building a personal experience between two people? How are you making sure you're giving back to the planet? That's why we don't send the thing. It's so wasteful. Nobody ever... You don't care about the gift. You care about the action on the other end, right?

Kim Ades: [00:04:42]

Greg Segall: [00:04:42]
The building the relationship. And the final thing is how do we build in just giving back to, you know, to those in need as part of the actual core of the business model. So that's why right from the get-go that was all built into the Alyce model from there.

Kim Ades: [00:04:53]
I really, really like it. Can you give me an example of some gifts that you gave to someone or that one of your clients gave to someone that made an incredible experience for that person who received a gift?

Greg Segall: [00:05:06]
Yeah. So I have a couple of good examples. So one of them, my favorite... I'll give you, like, my two favorites that I like getting out there.

One of them is a custom map. So what you can do is you can go on and you can actually pick a location anywhere you want in whatever zooming in or out of that location you want. And then it'll actually send you like a super high quality print of that location. So a lot of times I'll learn and I'll figure out that somebody's traveled or lived in, like, Barcelona, or they lived in China or they lived wherever it was.

And so I'll send them a map so that they can actually, like, have a nice printout. And now when they stare at that on their wall, they're always thinking of me, right? And that's a really good thing.

I always ask about kids or pets, you know, at the same time. So for kids, like, I love getting tinker crate, for example, or Kiwi crate, depending on what their age is, it's activities, you know, like a three month set of activities that now they can either their child and other thinking about me in terms of, you know, every time they're doing that activity, that's there.

And again, it's not about me, but it's about like the, the ability for that person to be able to do that. And yeah, I would say probably 50 to 60% of those people end up exchanging for something else that they want, right? Camping gear, or, you know, I don't know, other travel stuff or whatever it might be. Like, they have a million different options they can go into based on what their interests are.

Kim Ades: [00:06:16]
So tell me a little bit about your business, how many people do you have? Like, give us a sense of how long have you been doing this.

Greg Segall: [00:06:24]
So, we actually just celebrated our five-year anniversary.

Kim Ades: [00:06:27]

Greg Segall: [00:06:28]
But... I always put this as a caveat. I had my daughter right when we... When I started the business. And so, I consider that first year plus not really, you know, the business because I was really spending time with her. And I just came off of my previous business. I had sold that business.

So I was like, kind of in this like nice "let me spend as much time with my daughter as humanly possible and support my wife and, you know, and do all that". So we've been really at this, like in the current incarnation of the company for about two and a half years.

If you look at how we've been selling, who we've been selling to and everything else, you know, we have tens and tens of thousands of users. You know, we have hundreds of customers. Most of them are very large enterprise organizations that are using it. You can see our website if you want names, you know, that are that on top of that.

You know, that's... We're trying to be very, very focused on who we go after and really go deep in that specific segment, you know, of folks, and obviously you'll see the business continue to grow. So we've been, we've had a killer year for ourselves this year, so it's been really good.

Kim Ades: [00:07:24]
So I love the term "in this incarnation of the business", because what that means is you've changed over time.

Greg Segall: [00:07:32]

Kim Ades: [00:07:32]
Indicating flexibility and ability to kind of make things work when sometimes they weren't initially. So let's talk a little bit about your challenge. What's your greatest challenge today?

Greg Segall: [00:07:45]
So, as the incarnations have happened and there's many micro incarnations (you know, if you want to continue on that theme) of the business, it's really come to my attention that, you know, as we've gone past a hundred employees, now it's past 150 employees and during, you know, 200 employees, one of the key things that I noticed is that my voice, I am able to talk to less people as often. And my voice and what I say has heavy, heavy weight because of that fact.

So when you look across a business, as it's continued to scale, and we've gone from, you know, maybe it was two years ago, we're at 20 people, 25 people, and now it's 160 or so. And it's very apparent to me that I can't just have those normal interactions. And now with COVID it's even less, you know, where everybody's working from home.

So, the key for me is how do I, as CEO, make sure that my voice and the things that I'm talking about have the right context? Both from a timing perspective and then also from a weight perspective.

As you and I were talking right before we get on here is, like, I'm a very off the cuff type of a person, right? I'm trying to become more, you know, thoughtful and more planned out in terms of the way that I'm doing things, and I think I've made improvements there.

But even that is something where, you know, I could say something off the cuff because I had just heard a podcast and like, I'm thinking about something, and then somebody feels like, Oh, is that something that's really important now? Instead of it being, Hey, like, you know, this is a moment, you know, that's... Or something that I've said that, you know, is just a... Is more about inquiry, not about action.

Kim Ades: [00:09:13] Okay. So, it's very interesting, 'cause I have a team of coaches and when I first started coaching, everybody thought I could be the only coach. Like, "you're the only coach. It's Kim. It's Frame of Mind Coaching. You're the only voice in the company". And I quickly discovered that I didn't want to be the only voice in the company. And so, there was a distinction between being the face and the voice, right?

So my team of coaches, they can coach, I have no concern whatsoever. So, you said you had a baby. Let me use that as an analogy. Are you the only person who has ever taken care of your baby outside of you and your wife?

Greg Segall: [00:09:50]
Well, we had a nanny before and obviously she's in school now, so... You know, I mean, it depends on what, how do you define care.

Kim Ades: [00:09:57]
So, let's go to the nanny, okay? So before you chose your nanny, right? You may be interviewed a whole bunch of them. You looked at the references and you did all that, but once you chose your nanny, you didn't just say "there's the baby. Go get it. See you later". Right?

So there's a process of handover. What was the handover process? You held the baby, you gave the baby to your nanny. You made sure she grabbed it well. It, her... Is it a girl or a boy?

Greg Segall: [00:10:27]
It's a girl. Yeah, yeah.

Kim Ades: [00:10:28]
Your daughter?

Greg Segall: [00:10:29]
My daughter, yeah.

Kim Ades: [00:10:29]
Didn't want to call it an "it", but... You made sure that the nanny had a good, strong hold of your daughter before you let go. But for a period of time, you're both holding at the same time. Even if it was short, there was a period of time where you were both there.

And so what I would encourage you to consider is the same kind of process where right now you're the voice, but maybe what you do is you bring someone right beside you. Maybe two people right beside you, so you're the voice together. And maybe you lead and they have a tiny play in this. And then slowly they take up a bigger part in things that you do.

So you're partnering together where you're, let's call it "on stage" or in conversations at the same time and you back off. So there's a handover process. So you might start the conversation and leave. Or you might start the conversation and say, okay, as you double up with other people that you know and trust, that you do less and less of the talking.

So, that's kind of a visual that maybe might help you in terms of what you can do to hand things over where you're... You know, at first you're here and then you're slowly, slowly backing up. Does that make sense?

Greg Segall: [00:11:52]
Yeah, it does. I think there's... You know, you also don't just hand over the baby and just be like, "Oh yeah, just go take care of it". You're also typically saying, "here are all the things you need to know". Right?

Kim Ades: [00:12:02]
That's exactly...

Greg Segall: [00:12:03]
So, that goes with the context, you know?

Kim Ades: [00:12:04]
I was going there next. Okay. I was going to talk a little bit about training.

Greg Segall: [00:12:07]
I'll coach myself, I guess here, you know.

Kim Ades: [00:12:09] Yeah. So, first it's this concept of, you're both holding the baby at the same time, and then you're slowly backing up and you're checking in though, right? "Hey, are things okay? Are you comfortable? Have you experienced any problems? Oh, the baby was crying. Here's what I do when the baby cries, et cetera". Right? Conceptually, that's what we're after.

But the second piece of it is, absolutely, a little bit of training about the uniqueness of this baby, because not all babies are the same and especially this one, right? You have a unique point of view, you have a unique way of coming at this, your values are unique, et cetera. So now the question is, are you spending most of your time facing the public, potential clients, et cetera? And how much time can we carve out for actually training people on the voice, the angle, the concepts, the values, the perspectives, the priorities, and you know...

It's not about you getting more and more silent. It's about helping them more easily be able to take on a voice where they understand philosophically, where you're coming from. And so, sure that you might use some of your ideas, but that you're also encouraging them to say, "so here's the baseline, be creative too".

Greg Segall: [00:13:30]
How about in the case though, of... I mean, this is just something I'm trying to work on too... In terms of, like, there's a lot of things moving, right? As the company is scaling, there's so many things that are happening every single day. And there's so many, both internal and external factors to the thought process, you know, and some of the things that are happening there.

I think that's a good frame of reference in terms of like, how to actually talk and bring folks along on the journey that's there, but there's also the... I would say that's when things are structured. But what about when they're unstructured, right? And that's where I'm actually trying to hold that back now, you know, from folks and not say that until I have more of a frame of reference, you know, for it, but that's the other...

Kim Ades: [00:14:10]
I'll tell you. I think some of the most brilliant things can come out of unstructured conversation.

Greg Segall: [00:14:17]

Kim Ades: [00:14:17]
And so, what makes sense is not for you not to have unstructured conversation, 'cause that's where your genius comes from. It's when you talk, you're like, "Oh my God, I just said something really smart". Right? That's what happens. So I don't want you not to talk. I want you to talk. That's where that's the brilliance. But what's really important is to debrief after you talk.

So you say, "I said this. It's a one-off you don't have to use it ever again". Or you say, "I said this. Let's put it in our training manual. It was so good". Right? And that's the distinction. It's the post-random conversation debrief that needs to happen. Right?

So again, I'll use an example. When I train coaches, we have a series of concepts, principles, and strategies for coaching. They didn't come from a book. They came from here. Right? That's it. Here's how we do it.

Well, the other day I was having conversation with someone who was talking about someone in her life who was constantly, constantly kind of putting her down and giving her all the lists of things she was doing wrong. And I said, "Hey, you know, just cause she gives you a mango, you don't have to eat it. Especially when you know every mango she gives you is rotten. Stop eating rotten mangoes".

Greg Segall: [00:15:38]

Kim Ades: [00:15:38]
That doesn't come from a book. But I'm like, "wow, that was a good one. Stop eating rotten mangoes". And again, random. Never came up before, came up in one conversation. And I said, "that's good. That can be used in other coaching scenarios too, just because someone gives you a mango and historically it has always been opened up and rotten. You don't have to keep eating those mangoes".

Greg Segall: [00:16:03]

Kim Ades: [00:16:04]
So for you, it's the same thing. Some things that come out of your mouth are going to be genius. Brilliant. Just cause they only came out once doesn't mean they can't come out a million times again.

Greg Segall: [00:16:15]
Yeah. Well I think the... I mean, I think that's glorifying my geniusness, but that's definitely... Most of the things I say are not genius. You know, a lot of it is just, you know, either searching for conversation, and I think the issue is that I just... Again, I need to take more time and actually build construct and context around the statement, you know, and the whatnot that's happening there.

I think what happens is the end of your time is pulled so thin on that, that, you know, I just forget to do that many times, you know. So it's a habit that I think I just need to put more into play. I like the pre or the post brief... Forgot what we just called it.

Kim Ades: [00:16:52]

Greg Segall: [00:16:52]
You know, I think that debrief, you know, which I think is an Interesting angle on that, which is okay, "Hey, you know, we just said this, you know, what are the actions? What are the thoughts that come out of this?" Yeah.

Kim Ades: [00:17:02]
And I'll push you one step further, 'cause I'm guessing, and I might be totally wrong. Like, you seem like an action kind of guy, you take action, you make things... You move things fast. And so, if one of those action items was "we're creating a handbook, an handbook, for internal use", you might assign someone to put things in that handbook.

And so in the debrief you might say "that goes into the handbook". So someone's capturing it. And the moment it's in writing, it becomes a little more tangible, a little more real, and it becomes part of your playbook. And I think, you know, again, you're... I just get a feel your playbook is very, very unique. And so that has to be captured so that it can be passed along to the next hundred people who joined your company, who won't be able to necessarily get it from you directly.

Greg Segall: [00:17:57]
Yeah. I think there's... Those are on the bigger things. Right? And a lot of times, I'm very much a brainstorm-out-loud type of a person. Right? That's my thing. I think just different personalities. Some people like to be very contemplative in our thinking, come up with some sort of a, you know, hypothesis on something or decision on something and then try and work their way backwards from that. Right? Or some people get emotionally attached to that.

I'm much the opposite where I'm kind of like always searching and pushing the envelope and using my thought process to, you know, to challenge folks. And sometimes I think that can come across as like doubting, instead of it coming across as, like, just understanding, "Hey, I don't think this is, you know, this is something I should want to talk about. Not because I don't feel like you're actually doing your job well".

So that's another thing that I think is a really big challenge when you're thinking about it's the micro versus the macro conversations, you know. Like, there's philosophical, bigger things, and then there's the smaller, like micro things that I think, you know, I'm using that I think can also cause some of the doubt, which is something else I'd love to just hear your thoughts on too.

Kim Ades: [00:19:01]
So, I think what you're talking about is how you process. You're talking about how you process information, how you solve problems, how you think things through. The how part. And for you, the important component is to tell people "here's how I'm doing this. This is my thinking process. So, let me show you not only what I'm thinking, but how I'm thinking".

So again, the debrief is very useful, but in this case, it's the pro brief. I don't know if that word exists, but it's the "here's what I'm about to do" kind of conversation.

Greg Segall: [00:19:36]

Kim Ades: [00:19:36]
Pre-brief! There you go. Right? The thing that happens before and say, "Hey, there's... You know, like my mind is spinning. I just want you to know, I want to talk this out because I think that we can come up with an even better solution". So when they know where you're coming from and what your intentions are, they don't feel uncomfortable. They don't feel, you know, like they're coming into question. They sort of start to understand "here's the way he comes at it. Okay, fine".

Greg Segall: [00:20:08]

Kim Ades: [00:20:09]

Greg Segall: [00:20:09]
Yeah, that makes sense. I mean, it goes back to the context thing and I like that idea about the intentions. I'm just stating that out. It's funny. I was listening to a podcast the other day. And it was with Claire Johnson from Stripe. I don't know if she's still there or not. This is a podcast from maybe like a year ago and she's talking about how she created a one pager on how to work with me, you know, and I think that's something that we're... I've been considering doing, you know, even just for myself, you know. I started a draft of that like  last week, just so people can understand like where I'm coming from, you know, on that as well, so...

Kim Ades: [00:20:41]
Yeah. And it's that concept, except that you also have some fine, you know... It's probably working with you as not just a flat...

Greg Segall: [00:20:52]

Kim Ades: [00:20:53]
Experience, you also have some moments. And so, even so you want to capture what you're about to do before you do it, and then once you do it, you want to say, "Hey, here's what just happened".

Greg Segall: [00:21:03]

Kim Ades: [00:21:03]
Right? "Here's the good stuff. Here's the not so good stuff". And it's okay to have not so good stuff in order for us to find the good stuff. So that they're comfortable with the process from start to finish and they know where you're coming from.

Greg Segall: [00:21:15]
Yeah. Yeah. I think that's well put. Yeah.

Kim Ades: [00:21:21]
It's your baby.

Greg Segall: [00:21:23]
Yeah. It's not my mango. Yeah. Yeah. That makes sense.

Kim Ades: [00:21:27]
No, rotten mangoes here.

Greg Segall: [00:21:29]
No rotten mangoes here. Right.

Kim Ades: [00:21:30]
Okay. Well, that's always helpful.

Greg Segall: [00:21:33]
Yeah. That's very helpful. Yeah. I think it's, you know, it's something that I feel, like, I know it's good to have a reminder. It's also good to have a different frame of reference or a different perspective, you know, on that as well, because it's something where I'm always thinking about that.

And I know it gets me into hot water, especially with folks that have different personalities, that are more contemplative and, you know, inward, versus me, who's much more like outward. "Hey, let's go. Like, here's the thought process, blah, blah, blah". And that, that I think, you know,  is where I think that friction is coming.

Kim Ades: [00:22:03]
I get it, and it sounds like you need to verbally talk things out and when they hear you talking, maybe what goes on in their mind is, "Oh, no, another change. Oh no, we didn't do it right. Oh no, I'm getting criticized".

Greg Segall: [00:22:17]
Yeah. And I will tell you, I've definitely made marked improvement there, but it still comes up. And I think it's more amplified because of the time I'm able to devote to different folks, you know, in the business versus where it used to be before. We could have a half an hour conversation or an hour walk around wherever it was, you know, go back a year ago, even.

You know, so that's the fundamentals that, you know, I want to empower the team. And I also want to make sure that I'm understanding my ability to influence, you know, and how I'm influencing even in the subconscious, I think is the bigger thing, which is what I'm trying to be, like, very perceptive too. But it's very... It's tricky because I have to constantly remind myself and be thinking, you know, about that, and that's just like against my normal personality.

Kim Ades: [00:23:02]
You know, in university, they used to tell us how to write essays by saying, "say what you're going to say, say it, then say what you just said". That's exactly what you need to get... You know, what you need to start doing.

Greg Segall: [00:23:15]

Kim Ades: [00:23:16]

Greg Segall: [00:23:17]
I was an art student, so it was probably more relevant to like, "well, just sketch it out and then paint it. And you can always repaint it, you know".

Kim Ades: [00:23:24]
Okay. That works too.

Greg Segall: [00:23:26]
Since we're going on metaphors here, but yeah, that's it. Cool.

Kim Ades: [00:23:29]
Greg, thank you so much for being on my podcast.

Greg Segall: [00:23:31]
Thank you very much too.

Kim Ades: [00:23:32]
It was such a pleasure. It was great to meet you.

Greg Segall: [00:23:34]
You as well.

Kim Ades: [00:23:35]
For those of you who are listening. If there's a challenge that you have, that you want to share on the podcast, please reach out to me.

My email address is

And if you have a challenge that you're not so willing to share on the podcast, but still want to discuss, please reach out to me as well.

My email address is

Greg, I wish you the best of luck.

Greg Segall: [00:23:56]
Thank you very much.

Kim Ades: [00:23:57]
It was great to meet you

Greg Segall: [00:23:59]
You as well. Thanks.

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