Inside CTOx with Christopher Grant (Final).m4a
Wed, Nov 12, 2025

0:00 - Christopher Grant
are you doing this for real? Are you actually serious about this? That was kind of a, kind of a big shift and really kind of set the stage for, for, you know, being able to succeed kind of going forward. So, um, I think it was a really important thing to have that kind of conversation with myself about, are you serious about this?

0:17 - Donna
Welcome to Inside CTOx Podcast. I'm Donna, head of membership and partnership. And today we're stepping Inside the minds of some of the most in tech leaders out there. This isn't just a podcast. It's a place where CTOx journeys come alive. Where stories of struggles, breakthroughs and growths unfold. We're here to unpack the experiences of real CTOs navigating through our CTOx accelerator and membership program. So sit back, tune in, let's get into the story. Today, we're talking with Christopher Grant, a tech leader with nearly 30 years experience across startups. And Fortune 50s. At Home Depot, he led the migration of the $5 billion site with zero downtime. Very impressive. At Google Clyde, he helped shape products and guide enterprise innovation. And now, as founder of Nibari Consulting, he's a fractional CTOx helping mid-market companies turn tech into business wins. And outside of tech, you'll find him deep in the woods, strumming his guitar and carefully tending to his bonsais. Let's dive into his journey of leadership, innovation and craft in every sense of the word. Christopher, welcome.

1:36 - Christopher Grant
Great, great. Thanks for having me. It's exciting.

1:39 - Donna
My pleasure. Was that an accurate description of you?

1:42 - Christopher Grant
It was. It was. Yeah, it's nice to hear it all pulled together like that. So, appreciate that.

1:48 - Donna
Very impressive. Very impressive. Background there. So thanks for sharing. So what I like to do is let's, let's rewind a little bit, um, back to, if you can even remember that far back to before CTOx, CTOx, what was the spark that made you say yes to CTOx?

2:10 - Christopher Grant
Yeah, you know, that's a good question. Um, you know, I think it was really the idea of helping, you know, companies more directly and, um, you know, a lot of what I've kind of focused on in the past was, so I had a, I had a startup years and years ago before the, the.com Boston, it was just so excited to work with companies. And then a lot of the things I've been working on with the, the, the fortune 50 companies that we're working on has been really helping them grow. And so, you know, as the years kind of went on and, and, uh, things kind of moved up, it was really excited to kind of work with smaller and smaller companies. And so, you know, when we started, you know, looking into CTOx and seeing that there is an opportunity to actually, you know, do this on my own, but with the support of, you know, an entire community of people doing the same thing, it was really exciting to be able to, you know, get hands on. And so that was one of the reasons why I initially started looking into it. And yeah.

3:07 - Donna
Oh, that's great. That's great. So thinking back in, in the accelerator, as you started, Was there a particular moment that really, let's say, pushed you to your limits? Like, tell us about that.

3:24 - Christopher Grant
Oh, yeah. The, you know, the one that, it sounds silly, but the one that was, that really was a challenge is to send my first cold email.

3:32 - Donna
So it sounds silly.

3:34 - Christopher Grant
It's just an email, push the button. But, you know, it's funny because kind of being a tech guy, you know, we don't get into a lot of that. And so, you know, did I did I put the right thing in, you know, once it's out there, you can't pull it back. And so it was it was a bit of a learning curve. And honestly, after you know, after I had gone through it, I spent way too much time worrying about it. It's it's one of those things, you know, you get over that first bump, and you're like, Oh, well, that was nothing. So it's funny, because there's just all this this stress and consternation about sending that first and who's it gonna go to? Does it go to two people, 200 people, what? So yeah, no, that was interesting and challenging to get through, but yeah, we got through it all just fine. Now I'm sending out thousands on a regular basis, so it's good.

4:24 - Donna
That's really good. And what was the thing that just made you like hit that button? Were you just like, I'm just gonna do it today? Was it something on a particular day or just peer pressure from the other side?

4:36 - Christopher Grant
You know, honestly, kind of all the above. I mean, it was it was basically like, you know, I had to like, talk myself through it and be like, Look, this really isn't a big deal. It's just like the first and I'm never gonna meet these people, you know, or hopefully, let me rephrase that. Hopefully, I'll meet some of them. Hopefully, my, my work is useful. And I'll meet some of them and they'll appreciate it. But, you know, in the bigger picture, it's like, I don't actually know these people, you know, and so I'm sending out, you know, an introduction. And if it doesn't work, if they don't like me, you know, maybe I'll, you know, not see them again and I could try again with another group of people. So it was really more of getting in the right headspace for realizing that it's just an ongoing thing and nothing to really be worried about, I think.

5:17 - Donna
Yeah, that really, that mindset is like such a shift for people. And then once you go there, that's it, it's behind you and you just power through.

5:26 - Christopher Grant
It's the first, it's that first one, you know, it's like, you know, that first step is the hardest step, they say. And so that was, it was same thing with that one.

5:36 - Donna
And looking at your own evolution since joining CTOx, what's caught you most off guard about how you've grown?

5:47 - Christopher Grant
Yeah, you know, I think that's a good question. I think it's really the commitment that I have to this. And it's interesting because I see it with other members as well. And it's really it's one of those things that you get out of it what you put into it. And so I think early on, I was, you know, balancing my my day job with, you know, trying to figure out, is this something I'm going to do? And do you put in the time that you want to put into it? Are you actually do? I mean, you can kind of do some of the work. What are you really committing to it each week? And so that that is really kind of one of the big things that that I noticed. And then really once I kind of asked myself, well, are you doing this for real? Are you actually serious about this? That was kind of a, kind of a big shift and really kind of set the stage for, for, you know, being able to succeed kind of going forward. So, um, I think it was a really important thing to have that kind of conversation with myself about, are you serious about this or is this just another thing you're playing with? Um, um, so yeah, I think it's just really, you know, you put into it, you get out of it, what you put into it. And if you only put in half the effort, you're only going to get out half the results.

7:04 - Donna
That's very true. There's a lot of CTOx-Xers that are in a similar situation where they're working and try to do this either on the side or to try to transition over. What advice do you have for the people in the same situation you were in before you took that leap?

7:22 - Christopher Grant
It's an interesting one because you can definitely do it. I think I think the thing is to treat it like an actual job, like it is your destination and that, you know, this conversation of burning the ships, burning the boats, you know, are you going to actually commit to it or not? You know, I think one of the things is a lot of people that have regular jobs think about this backup that they have and they can go to it so they don't put in the effort, they don't commit as fully as they can. You know, they can get back on that ship or wherever, you know, that, you know, wherever they came from, you know, but if you, if you have that mindset that you're going to get fired, that you're going to get laid off, that you're going to quit, that you're no longer going to have this job, then suddenly it kind of comes into perspective that, you know, it may not be urgent to do this stuff, but it's extremely important to do this stuff. And I think part of that is setting up the foundation. So even if you can't put a hundred percent of your effort into it, setting up the foundation, what are the key areas that you actually do need to work on? And so for me, one of the more important things was figuring out how to build that pipeline so that when I do, or when I did switch over to a full time, that I wouldn't be relying on one client that I could build a client base. And so that was important for me. Some other people are more interested in building up the IP. They want to build their software, their frameworks or whatever. So whatever it is that's most important to you, make sure you're front-loading that piece of it. In the time that you do have available. So, yeah, I mean, it was just really, you know, focusing on, you know, your objectives and making sure that it's, you know, you're doing what's important to you and not just the urgent day-to-day tasks that come up from your day job.

9:08 - Donna
Yeah, that's so true. And, you know, we always encourage a pipeline. It does give you a little bit of that security that, you know, you have those leads in the pipeline and you can reach and engage with them. So that's really, really important. Great point. Thinking about the community, and we're very, very strong in our community from CTOx. Is there a particular connection or relationship or someone that you've met through CTOx that's had a sort of profound impact on you?

9:43 - Christopher Grant
You know, that's interesting. I mean, honestly, most of the people that I connect have been great. I would say George is an interesting person. It really just kind of goes to show what you can do and what you can put into, you know, he's got a lot of prompts. He's always, he's a great example of somebody who contributes to the organization, contributes back, you know, and I think it's that kind of, you know, again, to the point earlier, you get out of it what you put into it, you know, there's a great community there, but if you don't, you know, participate in the community, then you're not really going to get a lot out of it. So I think a lot of it, you know, the people that I've interacted with the most are the people that are in there, you know, contributing and asking the questions, you know, being vulnerable and, you know, hearing what they've done, their successes and their failures in all that. And then even when we get on the calls and there's these little nuggets that come up and then you follow up with somebody after the fact on that call, You know, I heard you say that thing that was really important. That was really cool. And then you have these side conversations. It's really engaging. And honestly, that's one of the big things that has kept me with CTOx, you know, beyond kind of going through that first accelerator is the community. It's actually interacting with the people, interacting with, you know, with all the new people that are coming in and the alumni as well, and really kind of sticking with it there. It's just been really, really rich. And useful for me.

11:14 - Donna
We get that feedback a lot from the community, like the importance of it. And I think, you know, I've been involved in a lot of communities in the past in various different aspects. And this community by far is the most supportive. Like you talk about being vulnerable and, you know, people sharing their mistakes and sharing their worries and their fears. And there's just so much love that's just poured back in every time somebody has that moment, like, it's just so wonderful to see because it's not it's not a competitive community. It's one of support. Everybody's just rooting for each other. And it's so great. You see those posts and somebody like signs a client, everybody's like, yay, emojis and congrats. It's fantastic.

12:00 - Christopher Grant
And I will say so I've been a part of a lot of other networks and, you know, kind of balancing them. And it was an interesting kind of growth for me to kind of go through some of those other ones. And end up with CTOx. And honestly, one of the things that I enjoy the most about this community is the fact that we're kind of all doing the same thing. You know, we're all trying to do the fractional CTOx thing. We're all struggling with a lot of the same questions. And how do we, you know, that first email is a common thing that comes up for a lot of people. And so it's nice to be able to get on calls where you actually share the same focus, the same direction, the same, you know, kind of not necessarily history, but, you know, background, I guess, and what you're to do versus kind of some of these other communities where you get people all over the place. But then also, you know, I don't know if you mentioned this earlier, but the networking with the marketing group as well. So yeah, it's not like you're just focused with the technology. There is this cross pollination of the other networking groups as well. So you get the focus of what you're interested in and what you're focusing on, but you also get to work with other people that are outside of the technology space and kind of work with them a little bit as well. So it's, it's, it's a great mix of, you know, focus plus kind of breadth of, you know, uh, experiences. So.

13:13 - Donna
No, it's great. It's great. It's so much great, great feedback, um, from that. Um, and being able to share, like you said, that, that one moment of, you know, I just need to send that email is, is so good. Um, thinking, thinking about that, like what's, what's one insight or mindset shift, um, through the acceleration. Is nigh a non-negotiable in your toolkit, never going back?

13:43 - Christopher Grant
Honestly, I think it's probably traceability and tracking of what I'm doing. So, you know, one of the nice things, I'll say it, I'll say it, I'll say it a couple days. One of the nice things and one of the annoying things at the same time is we've got this, you know, this weekly update on, on how are you doing you know, how much time did you spend on your, you know, and at first, I was like, Oh, man, there's that other email again, I got to fill this out. And, you know, one of the things is like, you know, they say if you don't track it, you know, you don't remember what it was, if you don't, you know, anyways, if you don't put the numbers on it, you're not going to improve it, you know, if you're not tracking, you're not going to improve it. And so it's the same thing with my business, right? So if I'm not tracking how many people I'm reaching out to, if I'm not tracking how much effort I'm putting in with my If I'm not tracking how many calls that I'm actually, you know, on a week, how do I know that I'm improving or, or growing that? And so that's kind of turned out, you know, from, you know, filling out the form and, and, and getting this on a regular basis, you know, like, Oh, here's the thing that the, that the group's doing too. It's actually something I've internalized and I've got additional spreadsheets and things that I'm actually tracking. Now I'm going into my tools and double checking and seeing, you know, I've got my Friday checklist. So, um, you know, So being able to go through and say, hey, I do want to get X number of calls a week that I'm on that are sales calls, or I'm reaching out to my network. How many times did I reach out to my old peers that I talked to recently? There's this conversation of 100 cups of coffee, and that's another thing. So reaching out and just having random networking conversations. So I'm tracking a lot of that in spreadsheets and things now, and honestly, Before that, it was really just, you know, how am I doing on my code and how am I, you know, my programming and all the rest of the stuff. So that's really turned into one of those non-negotiables where I don't know how I can succeed without tracking all of those little metrics. And part of that is finding the systems where it's not overkill. It's how do you actually, you know, kind of track that throughout the week without like spending so much time on that. And that's been a good balance there, I think.

15:51 - Donna
That's great to hear because yeah, tracking is so important and I think Sometimes we track for tracking sake, which is not the reason we do it or we track it because one of our VAs just honed you into the answer. But actually the tracking is to, you know, success is about making a lot of small moves and small tweaks, small improvements that all add up to one big shift. And, and the only real way to do that is to track through and say, okay, what am I, you know, what have I done last week? Worked, what didn't, let's tweak something, reevaluate it and et cetera, et cetera, et cetera. So I think it's one thing that, yeah, we all initially kind of rile against, but that's kind of where the success comes from

16:38 - Donna
So it's good to hear that.

16:40 - Christopher Grant
And one of the things is, the hardest thing about change is change, right? And so if we're not used to doing something new, it's going to feel awkward at first and I I think that's one of the things is like, you know, the sales calls, you know, the, the, the accountability sessions, all of this stuff feels awkward at first when you first get in there because you're not used to it, you know? And these are some of the things that, that, you know, you need to get through. And then once you, once you, you learn, you know, that it's not, it's like that first email, like once you learn that these things aren't scary, that they're not, you know, it's, it's really comfortable and it's a good community. And so everybody's there to help. And these are proven patterns that work. It's just a matter of trying them out. And then, like I said, I've got additional spreadsheets. So it's, you know, go through and learn what you're supposed to do, do the job, you know, the lessons, do the lessons and what you're taught and then modify it for, you know, your own organization, your own personal needs. And so, you know, I think that's one of the things there is just, you know, trust the process to some degree.

17:40 - Donna
Trust the process. We love that. We love that. Okay. Switching gears. We're switching gears a little bit here. If we were to check in a year from now, what's something that you hoped will be different or let's say radically better because of the journey through CTOx?

18:06 - Christopher Grant
Obviously, clients are a good thing there. Let's see. I think honestly, it's the engagement that I'm, so I would say the one thing that I think would be rather the better is the engagement with my network. So, you know, having shifted through the Fortune 50 companies and through Google, a lot of times what happens is you end up just focusing on the people that you're working with day in, day out, and you get kind of this bubble that you live in. And it was exceptionally so. At Google, Google is so big that there's so many people that you don't get outside of your bubble. And so, you know, one of the things that the community thing is engaging with the community, you know, talking with people in different industries, you know, working in different niches. And so a year from now, really, how have I expanded that, you know, beyond CTUX? How have I reached out to other, you know, groups, other people? How have I expanded my network? How have I built my own networks? And a lot of that is, is really driven from what I've learned with CTOx. The reason why I ended up here and why I renewed and why I'm still with it is because of the way that it works, the way that it succeeds. A lot of the other groups that I've been with haven't really had that. I've learned a lot about how to successfully engage with people, pushing yourself to have those multiple calls to go through and the accountability sessions, all the rest of that. Just the office hours that are set up to drop in and have conversations. There's just so many different avenues with the CTX community that I've seen a lot of ways to kind of implement that with, you know, other people that I work with, you know, just to drop in and have virtual coffee. So I think a year from now, it's really switching from just the individual project focus and the work that I do one-on-one with people to just having a broader network, a a larger group of people that I'm really engaged with, working with, talking with, and just generally enjoy being around.

20:14 - Donna
Building that network is such an important part. I mean, definitely what we've seen is those that have been the most successful definitely have that network and are able to reach out and build that network. And to those that don't have a network, we're saying, you know, get out there and start building one. It's never too late. It's like a mailing list. It's never too late to build that network and optimize for conversations. Sometimes we, you know, we get into the little bit of like sell, sell, sell. We're just trying to like close those clients. And we forget that actually human conversations are such an important part of this whole thing.

20:51 - Christopher Grant
Yeah. Yeah.

20:53 - Donna
So more conversations is what we want to see. Okay. Thank you, Christopher. All right. No, Christopher doesn't. This like, like any of our previous guests, but we have our Final segment. I'm going to do something a little bit different. I'm going to ask. You got me a little over here. I know you're a little bit worried. Don't relax. Relax. Um, I'm going to ask ChatGPT live. Cause you know, we all love ChatGPTs. We've got a bunch of customized ChatGPTs. So we thought we got to get it involved in this podcast. So I'm going to ask it for a question. To ask you, completely generated on the spot and you've got to answer it. Are you game? Oh, wow.

21:36 - Christopher Grant
All right. All right. We'll try it. We'll try it.

21:40 - Donna
Okay. Let's see what it says.

21:42 - Donna
All right.

21:43 - Donna
So here we go. I'm going to ask it in. Yeah, I'm not going to type. I'm going to, it's because my typing is going to be terrible. So hello, ChachuPT. We love a bit of spontaneity, so we thought who better to challenge us than A, What question would you like to ask a fractional CTOx at this exact moment in time?

22:09 - Christopher Grant
Okay.

22:12 - Donna
Hmm. Okay. This is a little bit different. Don't worry. It's not about AI. So ChatGPT would like to know. Christopher, if legacy tech had a voice, what do you think it would say to you right now? Would it plead for mercy, argue for redemption or whisper secrets you've ignored?

22:43 - Christopher Grant
You know, that's, I like that one actually.

22:45 - Christopher Grant
That's a good one for you.

22:46 - Christopher Grant
I like that one because I work with like Um, and, uh, you know, one of the things I think. I've learned over the years and I is, is very relevant here is, so I think the answer is the last one there, which is, you know, the secrets portion of that. And, and the reason I say that is because every time that I've approached legacy tech or worked with teams that have approached legacy tech, the first thing that the developer wants to do, the first thing that you know, anybody wants to do is to change it, is to fix it, to make it better. And a lot of that is not necessarily because it's broken, it's because it's old. And there's a lot of times where things were put in place for a reason, right? And a lot of times I see engineers just going through the motion to change things without actually trying to understand why was something done this way? Why was something done that way? And then you see that engineers end up in a worse boat because they ignored the reason it was done in the first place. And then they add up extra layers of complexity or novelty or whatever the new thing is. And so I think that legacy tech would probably tell me secrets about why it was the way it was and maybe things where the bodies are buried on the bad code because I would feel like the legacy tech would want the, a little bit of an upgrade, but also there's lessons learned in there about what to do and what not to do. So I would hope that the legacy tech would tell me some of those secrets to help me out in the future.

24:28 - Donna
That's a good one. That's a really good, really good question. It does come up with some good stuff, doesn't it? All right. Well, listen, Chris, thank you so much. Thank you so much for sharing your journey, sharing your insights with us today. We really appreciate your time. Thank you.

24:48 - Christopher Grant
Thank you. This is a great session. Thank you.

24:51 - Donna
Stories, experiences, and advice you hear today are incredibly valuable, not just for CTOs, but for the broader tech community and leaders. To our listeners, thanks for tuning in to Insight CTOx. Don't forget to follow us on social media, tag us, and share your favorite insights from the episode. We love hearing your feedback. Make sure to subscribe and check in again for our next episode, where we'll continue to explore the stories behind the tech leaders shaping the future.

25:18 - Donna
Until next time.