Inside CTOx with Sanjay Akut (Final).m4a
Wed, Dec 10, 2025

0:00 - Sanjay Akut
And it was the call with Marissa and Lior from CTOx that just cemented it in my mind. I mean, it just, there was no doubt going forward. So I kind of finished up what I needed to finish up and negotiated my exit and all of those things. And yeah, and I was off and running from there.

0:21 - Donna
Welcome to Inside CTOx Podcast. I'm Donna, Head of Membership and Partnership, and today we're stepping Inside 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 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. Welcome back to another edition of Inside CTOx. And today, I'm delighted to introduce you to Sanjay, a builder at heart in both business and life. He launched his first software company at just 19, running it for over a decade before stepping into the senior tech leadership role. But what makes Sanjay's story truly resonate isn't just the code or the companies, it's the commitment. Together with his wife, Stephanie, Sanjay has raised four incredible sons, including their adopted son, David, from Nigeria. A testament to the depth of his values and vision. Last year, with the support of CTOx, he made the bold return to entrepreneurship, launching Tukatek, a venture that's more than just a business. It's a declaration that success, freedom and family don't need to compete. Sanjay is proof that you can lead with both heart and hustle. Welcome to the podcast.

1:56 - Sanjay Akut
Thanks, Donna. Very much appreciate it.

1:59 - Donna
I'm delighted that we could, we could finally jump on. It's been quite a journey.

2:04 - Sanjay Akut
And I don't know where to go after that terrific intro, so I hope I live up to it.

2:11 - Donna
I have no doubt, no doubt. So Sanjay, you were one of the first people to join CTOx. So tell us a little bit about that journey and how it all got started.

2:22 - Sanjay Akut
Sure, so yeah, I was an entrepreneur at heart. I did that for the first 11 years of my career, then jumped into corporate. And so I was the most recently chief technology officer for an immigration law firm in the Washington DC area. And I knew that I wanted to get back into being an entrepreneur. And I had been kicking around the ideas of probably offering myself as a fractional CTO. And so I am sure that I had done searches and all those things, which kind of made me come across the CTOx ads and things like that. And it was just so fortuitous to me. I mean, really all the ads from Leor specifically, they just spoke to me, you know, are you thinking about this and all these things. So I just got on a call and said, I am thinking about this. My first call was before I left full-time I hadn't left yet. And it was the call with Marissa and Lior from CTOx that just cemented it in my mind. I mean, it just, there was no doubt going forward. So I kind of finished up what I needed to finish up and negotiated my exit and all of those things. And yeah, and I was off and running from there.

3:43 - Donna
That's great. That's really great. And was there anything specific you remember about that call? Any words of wisdom from Leor? Or just the general feeling that this is the right thing to do?

3:54 - Sanjay Akut
Yeah, I think it was the general feeling. I had been thinking about it for so long that it was just like, can I do this again? It was like a little bit of self-doubt. And I'll tell you that just the attitude of Leor and Marissa kind of totally erased that. It was like, you got this, man. And they asked me a bunch of questions. And I think They get a really good sense for, it wasn't lip service for sure. I think they get a really good sense for whether or not you might be successful with this thing. So yeah, I mean really just getting off the call, because that first call, it wasn't tactical at all. There wasn't anything really, oh yeah, I hadn't thought of that. It was just kind of this general, what are you thinking about, and here's what we do, and here's how we can help you. And it was that. Part of me not wanting to go into it again myself was like, you're in it alone. Entrepreneurship is lonely. And you know, and so who do I, yeah. And all the, I had been in corporate for the last 20 years. So everyone there, my network that I've built up, these guys aren't entrepreneurs. They're corporate technology folks. So it's something, it's just very different. It's hard to relate. So hearing from two folks that have been there, done that, and been successful doing it, but then also knowing that they would be that support avenue for me. That if I'm stuck or if I just need to riff on an idea or like this problem or something like that, that there's somebody there. And this was before there was so many people, right? That there's just somebody there was reassuring. And like I said, I got off off that call and it was just a no brainer to me. It was like, okay, we're doing this now and let's go. And so that was that.

5:47 - Donna
We, we hear that so often, like it just seems to have come at the right time. You just see that ad or the call happens at just exactly the right moment in your journey. And it just sort of cements it for that. So you were, we have to say one of our most successful CTO Xers. Tell me a little bit about your journey to that first client. Did it come easy? Was it a bit tougher? Did it just fall in your lap?

6:16 - Sanjay Akut
Well, it was, it did come like quote unquote easy from a timing perspective. I think I held the record for a while, but somebody beat me, which I'm glad that somebody beat me. And so, cause that's the goal, right? We want everyone to be successful. So that's awesome. But yeah, it was that first call. Whenever we got tactical in having that first call and really kind of setting up the game plan and the flight plan and all of those things, it was that idea of activating my network. And so, and I had basically said, oh, I don't, cause I'm not, I don't, I didn't run any like real outbound marketing at all to get started. I just activated my network. And the activation of the network was as simple a well-written LinkedIn post announcing to everybody that I'm doing this. And so, Leora and Marissa were able to give me some advice on, you know, how to then take it further when people reach out, that whole activating the network idea. And it literally was that. It was, I think it was less than a month, I forget now, but it was just within a few weeks that I had signed up my first client from there. So yeah, it was, then we were just off and running. And, and it was network referral after network referral that just kind of kept it growing from there for sure. So yeah, I would say, and it wasn't like, I hate saying easy, right?

7:45 - Donna
Nothing's ever easy.

7:47 - Sanjay Akut
And it was, it was my 20 years of experience and my reputation and all of that stuff that like made them kind of feel trusted with me that they were able to do it. But just from a time, it definitely didn't take as long was thinking that client one would take to land, right? And then you have a whole host of other problems to deal with, which is like, I have this client, what the heck? What am I doing now? And multiple clients. And when you're in corporate CTO, you're, it's just you have one client, your employer, and that whole juggling and time management and all those things. And just being able to lean on Lior and Marissa was just outstanding. It was just, I can't I can't talk enough about how much that support helped.

8:31 - Donna
Oh, thank you. Thank you. This serve, when the CTOXers get through that attract and convert, and they get into that serve section of the course, it's so exciting. It's so exciting to see. But yeah, you really feel like, oh, I thought I knew a lot, and then I get in here.

8:47 - Sanjay Akut
Right, right.

8:48 - Sanjay Akut
And I also don't want to diminish your role, Donna, when you then joined CTOx, because I was before you, right? You were. And so, yeah, and then you kind of helping with the further attracting and just we had a couple of calls about, hey, I got this on a sales call or this was my pitch and this is what I heard. And I mean, just that I just can't talk enough about the network. It's just it's a lonely journey. This entrepreneurship can be. And so finding like minded folks that you can just talk to about because we're all kind of going through the same things, you know, and it just, it just, even if you don't come out of it with a, that solved my problem, you feel better being able to just talk about it with somebody who understands.

9:33 - Donna
So yeah, the community aspect comes up time and time again. And on these podcasts, the interviews that I've been doing, it's, it's mentioned on almost, I think every single podcast, because you're right. It is, it can be, it can be a lonely journey. So just having a few friends along the way, even if they're just. Giving you that moral support more than anything is so important. Was there anybody in the network that you particularly connected with as the other members?

10:00 - Sanjay Akut
I mean the fellow early joiners I think because we were, it was a smaller network at the time.

10:11 - Donna
Yeah we have a little finder network yeah.

10:14 - Sanjay Akut
Yeah George comes to mind as like somebody that he and I I just kind of like were able to shoot Slack messages. It wasn't even anything big. It's not like we had, it was further both in our journeys where we finally jumped on a call and were able to have a face to face. But, you know, hearing some of the things he was going through on the group calls and then the occasional Slack message was just, just invaluable for sure.

10:40 - Donna
He's had quite a journey as well. We've, we've interviewed him for one of our podcasts. It's real journey, real journey. Now, Sandy, you've been ahead of the curve just more than once. When was the last time you felt that the curve was ahead of you?

11:01 - Sanjay Akut
I mean, maybe it was this, just the AI thing, like just a couple of years ago, you know, it's like, and this is what I'm hearing from my clients too, and I was feeling it a little bit also, is am I behind on this? And we were very early adopters. We were using AI and even the GPT models before Cat GPT was like announced and turned public and all of those things. But I don't know, I kind of felt that way. It was part of the impetus for me to make the move last year because I thought I might be behind this curve now. I spoke on the subject at law firm technology events because I was the CTO of a law firm and lots of companies would come up me a law firm specifically asking how how do they get started and things like that and and for a while I was thinking like am I behind you know not from a technology perspective but from a just like a this is a new thing perspective and I think I'm not taking advantage of it because when I did my company when I was 19 we started in 1993 aging myself now and then this little thing called the internet came about, right? And so, and there was the boom and the burst. And so, and we weren't an internet, we were actually a touchscreen kiosk system company back then, before we were all carrying around touchscreens in our pockets. And so, we were ahead of the technology curve for sure, way ahead of our time, I think. But in my mind, I kind of felt like I missed the boom, the dot com boom. And so this was kind of my chance, again, this is what I thought, was like, I am not going to miss this AI revolution that the whole world is going through right now, you know? Because I've been lucky enough, I'm old enough to have gone through the PC kind of change of the whole world, right? Whole world changed whenever the PC became a thing, then the internet, then the mobile revolution, phone launching and that changed the whole world. And now to go through a fourth one is like, it's so exciting for me.

13:15 - Donna
It's pretty incredible. So yeah, you're right to, to, I think the fact that you can identify that earlier on, like learn from those, let's not say mistakes, but those situations before I'm willing to take action. Like, I think that's, that kind of speaks to your success. Like you have that attitude. Um, so yeah. Going to serve you well. Now you mentioned you started a company at 19, got into then the corporate enterprise world, then got back into the entrepreneurial world. What did you have to learn and unlearn to move from that big corporate enterprise into that SMB smaller scale?

14:00 - Sanjay Akut
Yeah, so I was, I benefited in my career, Donna, from taking a number of different leadership roles in different sized corporations. So from billion dollar, thousands of people, and I was, you know, an IT leader to startups. So I was the chief technology officer of giftcards.com whenever it was very early on. And it's so I think I was employee 30 or 40 or something like that at the time. And so then we were scrappy, you know, and then whenever you move over into another role, then I was lucky enough that I had a number of different corporate technology gigs at kind of larger companies, smaller companies. I was an IT leader at our local utility company, the light company here. And so, I mean, just like, it can't be better capitalized, right? Like we just had lots of resources. And so, and I was told this by a number of folks in all the organizations that was my entrepreneurial spirit that made me successful in corporate world because I hate bureaucracy. I want to get things done quickly. I want value, all those things. I just, I mean, it's kind of like literally I was told that a number of times that that was what made me successful. So, so I never really became typical corporate guy. I would say the biggest thing was just resources, right? Like the budget that I Some of the organizations were, were very different than when I started Tukutek, you know, a few less zeros for sure.

15:41 - Donna
Well, but money's, money's not everything we, we, we tell ourselves. That's right.

15:46 - Sanjay Akut
And I think you can get spoiled a little bit and it's fun to like figure it out in a scrappy way. I, I enjoyed that. And I did that for the first 11 years of my career too. So obviously, so. So that wasn't like new to me at all.

16:01 - Donna
That's, that's great. It's so interesting that like, you know, having that journey and sort of coming back around again to where you are now. So thinking about that whole journey and all the things that you've learned and unlearned, what would be one principle that you now live by and would defend to the death?

16:24 - Sanjay Akut
That's a good question, Donna. So I would say, um, I think a lot of my success has been around my ability to communicate and collaborate with other folks. So I am, I'm a chief technology officer, so I'm a very technical person, but I think I'm like, I would be considered not your typical tech guy. I say that I, I can still write code and all those things, so I can, I have street tread with the devs on teams, right? But I can also then translate that into normal speak and speak to executives and all of those things, and even just bring people together and calm situations down. So it was really, it's my ability to work with people. And when you're running a business, I mean, that's just what you're doing, whether it's managing folks on your team or managing relationships with clients and vendors and all of those things. I mean, I just think that that is, so I don't know if it's necessarily a principle, but it is, you know, people first. It's that, oh, that is one that Leora and Marissa gave me, which was the who, not how.

17:32 - Donna
Yes, we love that one.

17:34 - Sanjay Akut
Which is all about people, you know, who, not how. Oh, I really embraced who, not how for sure, you know. So who can do this for me, right? Like, not how does this get done, but who can I bring on to do that? And that is one that I absolutely So we'll always stand by it, I've become a disciple of the who not how movement for sure.

17:54 - Donna
Who not how disciples, I like it.

17:57 - Sanjay Akut
Yes, that's right, yes.

17:59 - Donna
So fast forward 12 months from today, what does an ideal world, what would a typical day look like, Magic wand question here.

18:13 - Sanjay Akut
Oh, typical day, magic wand question. That I wake up whenever I want. And maybe I am in Florida. We're going to be moving from Pittsburgh to Florida next year, actually. That's the plan. It'll always be nice weather for me. And then I will be able to golf, maybe at a club or something like that, play some pickleball. My ideal world I think and check in on how the company is doing right like so build something that is sustainable and able to run and build something that maybe my kids can run and take over at some point and and I'm just checking in advising I don't think I'll ever like retire retire just because I just like it it's just what I like to do but it is certainly I'm you know, over the last year, comes with the territory. And that would be my idea when a year would be, I mean, a year would be awesome, you know, to be able to just like, and it's still running and everything's going and all of those things, but I'm able to just spend my time. My wife and I want to travel a lot and, you know, so maybe we are play some golf and then catch a flight to wherever we choose to go at that time.

19:40 - Donna
I recommend the South of France.

19:45 - Sanjay Akut
I will meet you there.

19:49 - Donna
Just at the top of my head. That's where I would recommend. Thank you so much Sanjay. Thank you. So for our Final segment, I get so excited about this because I've had so much fun with this segment and you don't know anything about this.

20:06 - Sanjay Akut
You haven't seen the other podcast. No, I'm anxiously awaiting what this is.

20:10 - Donna
The members have been so great about not, I think maybe, well, I don't know if it's a good thing or a bad thing, but they're not telling each other. So there's no preparation so far. When this gets out a bit more, people are going to know in advance. So these questions are going to be a lot of fun for you first folk of Gran. So for our Final segment, we're going to do something special. I'm going to ask Chacha live, right here, for a thought-provoking, timely question, completely generated on the spot. And you have to answer it. Are you game?

20:47 - Sanjay Akut
I'm game. Let's go.

20:49 - Donna
All right.

20:51 - Donna
Well, I'm going to use a voice action here, so bear with me a second. Here we go. Hello, Chat GPT. We love a bit of spontaneity, so we thought who better to challenge us than AI? What question would you like to ask Fractional CTO Sanjay at this exact moment in time? Okay, it's thinking, it's thinking. Sanjay, Chat GPT would like to know, surprisingly an AI question, if AI could now do 70% of your current value delivery, what's the 30% left that only you can do, and are you actually prioritizing it?

21:49 - Sanjay Akut
That's a great question, and that is very much in line with the who not how, where the who becomes AI, right?

21:58 - Donna
Yes, that's right.

22:01 - Sanjay Akut
And so the, who is AI in that sense? And so, um, like who, if I'm, if we have tickets and user stories and things like that, that need to get done and it's AI doing them and not people doing them, then great. Uh, and the think, 30%, which is just very far off is that relationship. It's the people piece. It is servicing my customer, my clients and making sure that they are feeling comfortable with where things are and where things things are delivered and I'm the one giving messages out and all of those things. We are transitioning into a little bit more of a software company. We're starting to offer platforms to our clients and kind of transitioning into that role. But there's still clients at the end of the day who are kind of like signing up because they trust me to deliver for them. And so that relationship and working with the clients and bringing on new clients while we fully get lots of support from AI on sales and marketing, the actual like kind of closing of deals. Yeah, it just can't be done with AI at this point. And so, yeah, that's the piece. It's that people piece, I just think. And boy, that would be awesome if 70% everything was just delivered autonomously in the background. We're working on it for sure.

23:28 - Donna
Well, AI is not out there playing golf and definitely not the company that you no doubt are Sanjay on the golf course. 30% playing golf. I love it.

23:42 - Sanjay Akut
Thank you so much.

23:44 - Donna
Thank you so much for joining us, for sharing your journey, sharing your insight and your wisdom. We really, really appreciate it. And we'll see you again next time.

23:54 - Sanjay Akut
Thanks, Donna. Appreciate it.

23:55 - 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 Inside 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.

24:23 - Donna
Until next time.