Inside CTOx with Bob Stewart (Final).m4a
Wed, Nov 12, 2025

0:00 - Bob Stewart
There's a light at the end of the tunnel and it's Leora at the end with a flashlight going.

0:08 - 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 innovative tech leaders out there. This isn't just a podcast. It's a place where CTO journeys come alive, where stories of struggles, breakthroughs and growth 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. Welcome to another edition of the Inside CTOx podcast. Today, we are blessed with a very special guest, Bob Stewart. Bob has over 25 years experience as a technology leader and is now the founder of ApexVelocity.ai, a fractional CTO advisory. He helps tech leaders tackle AI governance, compliance, and scalable innovation. Former firefighter and rescue driver, wow, he brings mission-driven urgency into technology. Known as a spiritual technologist, Bob sees AI as a co-creative partner, not a threat. Dedicated to building ethical, scalable systems that safeguard people, data, and our futures. Welcome, Bob.

1:34 - Bob Stewart
Thank you. Pleasure to be here. Thanks for having me on.

1:37 - Donna
That's quite a, that's quite a resume. Quite impressive. Former firefighter and diver. Wow. Rescue diver. Wow.

1:47 - Bob Stewart
I'm sure you have about 20 years on 20 of fire and rescue service as a volunteer. In my community. All the fun stuff.

1:59 - Donna
Wow. That's, that's truly amazing. Truly amazing. Um, so welcome to the CTOx podcast. Uh, we're going to, to dive right in here and thinking back, um, you know, life before CTOx, if you can remember that far back, what was the real trigger that pushed you into saying yes to joining CTOx? Was it ambition? Frustration, something else entirely.

2:26 - Bob Stewart
I think it was the bespoke nature of the niche of CTOs and a year's worth of exploration. So I'm sort of the quintessential person you shouldn't give up on. I went to my first 15 minute call. I blew off my next one. And then I came back a year later once I had you know, been through a gauntlet of a couple other coaches to find, you know, the focus of what ultimately I then knew I needed to do. And I haven't looked back. Honestly, it's one of the most well-organized machines of, you know, from a coaching systems delivery perspective that I've come across. And I've spent thousands, if not tens of thousands of dollars, you know, in coaching. So it's been wonderful so far.

3:28 - Donna
Thank you. That's very, very kind words. We appreciate that. Everybody has their, their different story of joining, but they're, they're all like equally valuable to the community. So we appreciate you sharing that. Every accelerator has its breaking point. When did you, when did you feel the most heat? And what did you do to push through that?

3:50 - Bob Stewart
Yeah, I'd say that I'm still on the gas pedal with that one. You know, the process of identifying yourself and figuring out who you are personally versus who you are professionally, and how you fit into the marketplace and then deliver that, that's been the biggest And I'd say that the peer aspect of the program has been the most motivating, you know, not wanting to let other people down, not wanting to let myself down, making weekly commitments to pushing the ball forward down the field, getting it across the line, and then saying, okay, now where, and turning around and running the other way. So it's been through each of those parts of the process of working through the system that Lior has laid out of first understanding who you are to whom, and what do you solve for whom, and how do you solve it in a way that is going to delight people and can scale, and then applying that to how do you find people that will work and that, you know, that will want to work with you. And then, you know, getting into the delivery side. And it's certainly been, you know, a challenge, but yet, you know, one of those things that you can see that there's a light at the end of the tunnel and it's Leora at the end with a flashlight going, Yeah, I think having that light at the end of the tunnel over that, having Leo over that flashlight, I think that's, that's important for people to see that because you know, that's where we're, we're, we're driving to.

5:56 - Donna
Cause this, this isn't an easy, it's an, it's never an easy challenge. Um, but you know, that's, that's what makes the reward all the more rewarding at the end of it. For sure.

6:08 - Bob Stewart
Yeah, and seeing and being able to connect with someone who's sort of been there, done that, has the type of a practice that I aspire to have and can save me a lot of time. That's what I'm all about. I don't have time to reinvent the wheel at this stage of my career. So that was the big motivator of joining CTOx is it's a proven process, it's a pathway that's well-defined and it's got a trailblazer running out front, marking the trail as we move through the market.

6:44 - Donna
All of the lessons, none of the scars. That's what we try to encourage people for.

6:48 - Bob Stewart
Occasional stick in the eye, but yeah.

6:53 - Donna
Absolutely. And since joining CTOx, what has been the most surprising curve ball in your personal growth? Like something you were like, wow, saw that one coming.

7:05 - Bob Stewart
That's a great question. A personal curveball would really fall more around, for me, recognizing that other people see a value in me that I don't necessarily see. So the opportunity to get peer review and peer feedback where people say, hey, you know, you give good advice. And even though I never really questioned my ability. It was more of my willingness to expose myself and put myself out there. And I'd say that that's been one of the more delightful things. And maybe I'm guilty of liking it when other people say nice things about me, but I'll keep that.

7:51 - Donna
No crime in that. Yeah, no crime in that. You mentioned peers and this comes up a lot in the conversations that we have. How does the peer group in CTOx compared to other peer groups that you've experienced in the past?

8:05 - Bob Stewart
Well, you're surrounded by other CTOs. So, you know, one of the things that CTOs, well, I'm speaking for myself, but that can become a bit of an issue is that you have conversations with folks and then you don't know whether they actually understood what you were talking about. Because a lot of people will sit there and go like this and go, yeah, that sounds great. But you know, you know, when you talk When you hear them talking about you later, they're like, yeah, he lost me at hello. And in the case of this, you've got other seasoned CTOs who are listening to what it is that you say. They're measuring it against a career that has brought their entire life work to that moment to be there with you. And so when they reflect, they're actually genuinely providing information that is valuable because they've been there, done that, or they have the bandwidth to actually absorb what it is that you're trying to accomplish or do. And then to in turn challenge you and motivate you to look at things from a different perspective than you may have brought with your intrinsic baggage as a human. And so I think that it's been that aspect of the peer review and the peer progress and the accountability to one another to actually want to help the other person. Oftentimes in life, you run into someone and you tell them, oh, I got this good thing and that's good thing going for you. And they're all like, oh, yeah, that's great. But if things were not going good for you, they'd be like, oh, that's just so bad. Feel good about it, right? Because yeah, at least it's not all just me, you know, well, finally, he's got a problem. But these, these are, these are people who, you know, genuinely want to make progress themselves, they want positive feedback, and they want to reciprocate by giving, you know, constructive feedback to you. And I think that that's the difference is the, the affinity of the peers in the CTOx program.

10:24 - Donna
That's great. And I like the way you're saying it's genuine because I see this over and over again, like the members, they just, they're really rooting for each other. They're really just so supportive and they want everybody to win. It's not a competitive or negative environment. The community is such a big part of like CTOx. Has there been a particular person or story that's challenged you or challenged your thinking in any way through the community?

10:58 - Bob Stewart
I think Marisa would be the one who comes to mind. Marisa would be the one who comes to mind. She has, you know, I latched on early to who she was and what she had accomplished in her career and who else she had supported in in her careers, multiple big, big names, named people. And, and so, you know, I think that the the opportunity to, to share with her has been one of the most pleasant surprises in terms of someone that can look at me and look at what I have been and look at it from a more holistic, broader perspective than just the CTOx work. And then challenge me to find, you know, how that can be amplified to then create the demand side of the CTOx work.

12:11 - Donna
It absolutely does. She's our, you know, head of coaching. And just all around badass. And yeah, she's challenging. She will not let it go. If she thinks somebody is not living up to their potential, she's definitely going to challenge you. So she'll be delighted to hear that for sure. What's one principle or insight, let's say, that you've picked up through the CTOx your time here at C2X, that you're just going to fight to keep like, no matter what, like nothing's going to change your mind or holding onto this one.

12:51 - Bob Stewart
I would say it's, uh, it's Lior's perspective on leverage, um, and how to, how to, um, how he has, um, structured his. Practice to allow him to scale in a way that is sustainable and gives him the power to call his own shots in terms of what deals he cuts, with whom he cuts them, how they fit into his portfolio, and And to make sure that all of those are in amplification of the systems that he has laid down over the course of building, you know, CTO X and his other ventures. So I would say it's that it's that was that mindset that he brings to the table and I find a great deal of value in listening.

14:09 - Donna
Yeah, he's, he's, I mean, Lior is just so great. And it's so interesting when, when he talks, it just all seems to make sense. Like things that, that were confusing before, or you weren't really sure where it's going. Like you listen to Lior, and you're like, that makes total sense. Like just the way he's, he's able to explain it.

14:27 - Bob Stewart
And it's not just, it's not just that, I'd say that he, he did a post a while, a little while back where he basically said, well, this whole thing just went terribly. And we just had a really bad, I don't forget what it was, like a really bad quarter, a really bad month. And so then we had to do X, Y, and Z. And now it's up to everybody on the team to turn it around. And the vulnerability and the willingness to talk about not just everything goes great, but how to handle when everything isn't going great has been a delight to be a part of

15:12 - Donna
Definitely that vulnerability, it comes up over and over again from the team, from the leadership, from the members, everybody at some point feels that vulnerability. What would you say to people or what advice would you give when you're feeling that vulnerable? What should members or any members of the community, what should they do?

15:37 - Bob Stewart
Yeah. At the end of the day, you got to remember that you're really just competing with yourself. And that what other people think or say or do doesn't matter. It's a case of believing in your own intrinsic worth as a person. And as long as you remain focused, solutions will present themselves. So I'd say that, oftentimes for me, it's setting some sort of a micro goal, like by the end of next month, I'm going to get this and then setting internal goals that I feel that I need to achieve in order to justify doing that. And so, yeah, those are some of the things that, you know, when I find myself stuck somewhere, it's really usually because I haven't figured out what is big enough to motivate me to power through it. So I need to then do that, so.

16:53 - Donna
And just small steps, they all make, they to make a big difference.

16:58 - Bob Stewart
Consistency wins the race.

17:00 - Donna
That's it, that's it. Bob, when we check back in with you again a year from now, which we most certainly will, what would shock you about how your C2X journey changed the way that you lead and how you deliver to your clients?

17:19 - Bob Stewart
The view from my super yacht in St. Bart's would shock me.

17:25 - Donna
Shocked by the awe and the beauty of St. Bart's.

17:30 - Bob Stewart
Racing super yachts, yeah.

17:35 - Donna
I wouldn't be shocked if you told me one day you were racing super yachts. That would not shock me in the least.

17:42 - Bob Stewart
I have associates and friends who will probably see this that race super yachts in St. Bart's. Yeah, there is an entirely grander world than we often allow ourselves to experience. I heard it put the ask of life a penny and a penny it will surely pay. So I'm now beyond asking for just pennies and I'm applying 30 years of tech career towards achieving a sustainable practice that has a consistent recurring revenue stream. And it doesn't take a lot to have a lot. It takes commitment. And I have that. So I'm not always the smartest, but oftentimes I can just work shorter, longer, faster, stronger.

18:49 - Donna
Sounds like a song. You do sound like you're going to break into song, which I'd love to see. Yeah. The commitment, you know, again, we see it over and over again. Like it's such an important, important part of that.

19:04 - Bob Stewart
It's a decision.

19:06 - Donna
That's it. You decide to do it and you commit to it and, and, you know, taking action bias toward action, as Leor often says.

19:16 - Bob Stewart
That's a distinction. Oh, I would say, though, that that gap in the game, the the entire principle of that and looking back to see how far you've come has been one of the biggest takeaways for sure.

19:32 - Donna
Yeah, it's a wonderful book. I really love love that book. Ben Hardy's such a great writer in that, too, with Dan Sullivan. And yeah, I think sometimes, you know, we're focused on so much of the now that we forget to look back. And this is why I love to do these podcasts. I love to talk to the members and go think back to, you know, six months ago, a year ago, like it's such an incredible journey that so many of our members have been on. That's great.

20:06 - Bob Stewart
Okay.

20:07 - Donna
Thank you, Bob. Now for our Final question. This is where I get most excited. Bob doesn't know anything about this. He's a little nervous. All right. I'm going to ask chat GPT live right now for a thought provoking, timely question. And Bob has to answer it. Are you up for the challenge, Bob? Oh, every day.

20:34 - Bob Stewart
Okay. Sounds good.

20:38 - Donna
No, no, no. No prepared needed.

20:41 - Bob Stewart
Oh yeah. Prepared. Preparation.

20:46 - Donna
Very appropriate. Very appropriate classes. Okay. So I'm going to, I'm going to ask Chat GPT. Hello, Chat GPT. We love a bit of spontaneity here. So we thought who better to challenge us than AI? What question would you like to ask a fractional CTO at this exact moment? Moment in time. Okay. Let's see what it's saying. Okay. Ah, okay. This is a good one. This is a good one for you, Bob. Awesome. You ready? If you could erase one best practice that's become in tech leadership over the last two decades, which would you scrap and what would you replace it with?

21:44 - Bob Stewart
I think I'd, I'd scrap the way velocity is measured in terms of time and I'd replace it with how it's measured in terms of getting it right the first time by having adequate requirements. In other words, most people will start a project and then measure how long it takes to get to this other point and call that velocity. In reality, the task has to be done, but then this task has to be handed off to another person. And what's not measured is the time it takes to get to here, and that this was not accepted, and then had to go back and be done, and then had to go back and be done, and then had to go back and be done. So now you have this much plus this much plus this much plus this much. And the reality is, is that because you didn't measure what was going to be required for the next stage and make that be a part of the input stage, you've, you've misapplied that you've misapplied velocity is productivity, not time, not.

23:23 - Bob Stewart
not points on a sprint.

23:27 - Bob Stewart
It's actually GSD.

23:33 - Donna
Those are very dramatic taking off the glasses.

23:40 - Donna
Bob, I love that.

23:42 - Donna
Thank you so much.

23:43 - Donna
Thank you so much for sharing.

23:44 - Donna
This has been a lot of fun and I appreciate your vulnerability in sharing with us today, your insight, sides and the value you bring to the community.

23:53 - Donna
We all love you here at CTOx.

23:56 - Donna
Thanks for sharing and we'll see you again next time.

24:01 - Bob Stewart
I love you too.

24:02 - Bob Stewart
Take care.

24:04 - Donna
Stories, experiences and advice you hear today are incredibly valuable, not just for CTOs, but for the broader tech community and leaders.

24:12 - Donna
To our listeners, thanks for tuning in to Inside CTOx.

24:16 - Donna
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24:21 - Donna
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24:23 - Donna
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24:31 - Donna
Until next time.