S03 EP08 with Nancy Henriquez - Coaching Process

Nancy Henriquez has been building businesses since before she had a roadmap for it. She founded an MSP, grew it, sold it, then started another one. Now she runs Sibyl Consulting Group, leads community at MSP Unplugged, and is in the middle of a new acquisition.

This episode takes the listener through what it took to shift from reactive operator to proactive one, why delegation is the growth lever most owners resist longest, and how AI is landing across the MSP space right now. Nancy also opens up about Claudia, the AI second brain she built on Claude, seeded with her own book and coaching frameworks, that now manages her inbox, reads meeting sentiment, and coaches her on her own capacity.

Author of Break-Fix to Breakthrough. First generation American. ADHD superpowered woman. 

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

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Transcript

Michael Cupps: [00:00:00] Hello, and welcome to The Habit Architect. I'm your host, Michael Cupps. Thanks again for joining us, today, we're gonna talk to, what I consider a powerful woman. She's, she's really impressive. I've had the opportunity to meet her, oh, probably a month or two ago at a luncheon, and we kinda picked up conversation from there, and I'm so impressed with how she conducts her business and, and more importantly, how much business she's doing across a lot of different channels, and it's really exciting.

Michael Cupps: 'Cause of the way that things are happening today, a lot of people work in multiple jobs. And when I say that, it's maybe not multiple jobs, but it's they have a job and they're doing a side hustle, or they're, they have a job and they're doing some volunteering, or they're maybe p- participating in a non-profit.

Michael Cupps: Her name is Nancy Henriquez. She's gonna join us. She has founded businesses. She has bought businesses. She has grown businesses from zero and up and built communities and so on.

Michael Cupps: So without further ado, let's bring Nancy from backstage on, and we'll let her introduce all of the things that she has been running and doing. Hello, Nancy. 

Nancy Henriquez: Hello, Michael. How are you? 

Michael Cupps: It's great to see you again. I'm so glad you ha- you could take time [00:01:00] to, to visit with us. I know you've got a lot going on, I'm so impressed with the way that you run your businesses, and you have a big acquisition that you're part of now and that, that's maybe not public yet, but we'll talk about, a little bit about that and how it supports your business.

Michael Cupps: But why don't we start with just you introduce yourself because I think you can do better justice than I could. 

Nancy Henriquez: Yeah. Thank you very much. First and foremost, thank you so much for having me on the show. this is amazing. And Zelda is leaving her office there, for those that can see on video. My little dog has, She, she's always along my side, so she just left her office. 

Michael Cupps: There 

Nancy Henriquez: no, so thank you again for having me. I'm, Nancy Henriques for those that don't know me. and so I, have been an entrepreneur since very young.

Nancy Henriquez: I, although didn't have a roadmap per se, I would say a- like many in the IT world that have started an IT services-based company, you start because you love the technology and you wanna help people, and then you become an accidental entrepreneur. That is [00:02:00] exactly what happened to me. Yeah ... and, slowly but surely I grew one business, sold it, started another because, I can't help but torture myself.

Nancy Henriquez: Yeah. Basically sold it. grew it, sold it, and then, had the opportunity to then work for a few other companies where I got to, scale in multiple different ways. I got to grow communities within the managed service provider space, and, it's been quite a journey, for sure 

Michael Cupps: That's fantastic.

Michael Cupps: That's and I don't wanna get too personal, but your, I think you mentioned that your family's originally from El Salvador, and they- Yeah ... they moved to the US. Are you second generation, first generation? What's, 

Nancy Henriquez: I'm first generation. I am first generation, yes. I've had the privilege to be born in this country, but the same privilege of being so close to my roots- 

Michael Cupps: Yes

Nancy Henriquez: that it has been, embodied in who I am, 100%. 

Michael Cupps: Yeah. And I only mention that because I, I love that f- that story that you guys [00:03:00] moved here, and you've not, you're not just finding a job, you're building businesses. You're employing more people. It's, and it's fantastic, and that's what I just love about that, that heritage of your story.

Nancy Henriquez: I have written a book, right behind me on my shoulder. It's called, Yeah ... Break Fix to Breakthrough. it was a, a collection of experience that I got to, put on paper and, be able to help others that, either can relate to my story or have been where I was, and, be able to help them with some of the mistakes and some of the, lows that I had in life and be able to learn from that, 

Michael Cupps: yeah. 

Nancy Henriquez: one of the things I, as you mentioned, my family is from El Salvador. I like to say that I come from an entrepreneurial family, although, not formal. So my, my grandmother was illiterate. She didn't learn how to read or write. She didn't have the access to school in that way.

Nancy Henriquez: But talk about side hustles. That, that woman- was not only raising kids, but she was lifting up a community, i- [00:04:00] in, in her way, and she was, she had a little store at some point in time just selling different types of supplies. she would sell cheese that she would make homegrown cheese. 

Michael Cupps: Wow.

Nancy Henriquez: and as I tell her and my family, with the language that I know and able to have, the education that I've been able to have, the access that I have been able to have, how can I not, 

Nancy Henriquez: do more than what she was able to do with what little she had? 

Michael Cupps: Yeah. That's fantastic. and we underestimate sometimes the value of what we learn from our grandparents, our parents, that, they were the original problem-solvers, right? they figured out ways to manage what they had to do to keep the family and to keep the community, as you said with your grandmother.

Michael Cupps: And I'm so thankful for that in my life, 'cause I grew up on a farm, and we had to do stuff, right? And I think in the age of AI, those problem-solvers are gonna be really the innovators, I think, because they know how to solve problems.

Michael Cupps: And now it's not just saying AI for AI's sake, it's here's how we're gonna use it in this solution to solve that problem. and I look forward to talking to you about that, too. [00:05:00] But, I wanna start, though, with... A- and then I wanna get into MSP, too, because I know that's where you exist as well.

Michael Cupps: But, how are you managing all that? How do you say- ... "Okay, this is what I'm gonna spend on this one. This is what I'm gonna spend on this one." How are you doing that? 

Nancy Henriquez: and it's- it's really funny and interesting 'cause when we met during that luncheon, we had a conversation about ADHD.

Nancy Henriquez: Yep. And, and I- I think that, ADHD has become a superpower for me in that way, where, Love it ... I- I like to say that it's a, I'm firing on all cylinders. so I- I dedicate... I do have blocks of time where I dedicate to each thing. but the other side to that is I just don't sleep.

Nancy Henriquez: it- it really is... And- and I- I tell, I teach this a lot in coaching, right? Where, it's all about delegation. It's knowing your strengths- Yeah ... and sticking to what your strengths are, and then being able to delegate from that. finding partners that can help it, yeah, can [00:06:00] jump in and help- Yeah

Nancy Henriquez: in multiple ways in areas that allow you to do a lot more, with the limited time that we all have. 

Michael Cupps: I'm glad you said that. I do applaud that- that ADHD can be a superpower. But I think delegation is one of the things that people struggle with, especially in your case.

Michael Cupps: You own a business, and you're- you're expanding that through acquisition and just general j- organic growth. And it's so easy for owners and CEOs to just say I'll do it. I'll do it. I'll do it." And, because they know it and they have the domain knowledge, and certainly they're qualified to do it, but should they, is the, is a real question that people should ask.

Michael Cupps: And- and not many people talk about delegation as being a superpower, but I think it is, and- and I'm glad you- you mentioned it. Oh, 100%. 'Cause, it's trusting people to- to do what you need to do, and you just get there faster, right? Oh, yeah ... when you can properly delegate. 

Nancy Henriquez: Just, yesterday I had someone, make a post or comment on a post that I had made where they said, "I am terrible at managing people."

Nancy Henriquez: And I said- ... "But I'm sure [00:07:00] that you are prompting your AI." Yes. So if you are prompting your AI, it's the same way to- Yeah ... being able to delegate to people. You have to prompt them, you have to guide them, you have to, Yeah ... put guardrails. You have to then, train it and- and you have to then retrain, Yeah

Nancy Henriquez: If you think about it in the same way you're doing it and for some reason it's easier for you to think about when it comes to telling an AI what it is that- Yeah ... you want, the instructions- Yeah ... that you want from them, but it's a little bit harder for, from, for people.

Nancy Henriquez: Yeah. And, his response was, "I hadn't thought about it that way, so I'm going to now think about do- framing it in that fashion." 

Michael Cupps: 

Nancy Henriquez: I said good." 

Michael Cupps: Yeah, exactly. Let's get into the MSP business.

Michael Cupps: so for what, if people... I don't know if I have a lot of MSP, people that watch the podcast, but it's a managed service provider, and essentially that's a business, and you can probably explain it, that helps other businesses manage all their IT stuff. Is that fair to say? Or maybe you could say it more elegantly.

Nancy Henriquez: I like to say it is like a, [00:08:00] having an IT department that is just outsourced. So everything from your help desk, so when something is broken, they are helping, they're jumping on and helping in that way. But more when it comes to a managed service provider, it's the proactiveness of being able to manage all of the computers, the environment so that those problems are less, seen less, 

Nancy Henriquez: and of course protected as much as possible. 

Michael Cupps: and so there's a lot of MSPs out there, and maybe they specialize in security or, desktop or things like that. But you obviously have run a successful MSP, and you've grown it and you've sold it, then you're building another one and you're making an acquisition that helps that.

Michael Cupps: So what was the breakthrough moments for you in your business that... and maybe they're all in the book, you can say that, but, maybe you could highlight it for us. 

Nancy Henriquez: But, definitely a few key things, that came from that. And one, the first thing was my mindset.

Nancy Henriquez: I had to change my mindset from a reactive mindset to a proactive mindset. Especially going [00:09:00] into a proactive business where we're wanting our clients to be proactive about their technology, but yet our leadership mindset is stuck in a reactive mode. And so that was the very first thing where I realized I, I need to change how I'm thinking, even how I'm handling myself and- my, my leadership, that goes to delegation.

Nancy Henriquez: That was the next thing, which was- Yeah ... how do I then, make sure that I am properly delegating? I have to let go in order to grow, which is that saying that a lot of people say. but that, it's so hard when you start the business, and I know many business owners can probably relate to this.

Nancy Henriquez: you start a business, it's your baby. It's- Yeah ... you put so much energy and love and thought into it, that it is hard to then trust someone and let go of being able to, have some help. But if you- Yeah ... don't do that, then you can't focus on the right [00:10:00] things in order to then be able to operate more efficiently.

Michael Cupps: Yeah. 

Nancy Henriquez: Yeah. And so that was, biggest thing, for me there. The, I would say, the second, breakthrough w- was community. It was having mentors, coaches, just peers that we w- continued to talk about what was going on within our businesses. and you, I honestly believe that you cannot grow a business on your own.

Nancy Henriquez: and so having a community that you can rely on, that can help you, get out of a pickle when you're in one- Yes ... or can spark an idea when you are immersed in what you're doing it changes the game for you. 

Michael Cupps: I love those two things.

Michael Cupps: Being proactive and thinking about community are two things that actually go hand in hand, because you're gonna see ideas, you're gonna hear thoughts, you're gonna hear bad stories and bad examples of where you don't wanna be from good examples to where you wanna be and you aspire to be.

Michael Cupps: So I think that those two are interlinked, and that's fantastic. The, I'm curious what you think about AI coming [00:11:00] into the MSP business. Because AI allows you to be proactive, because you can start listening to signals you couldn't listen to before. You can think further ahead, things like that.

Michael Cupps: But it also, like you said, sometimes being in a, running an MSP business is a reactive business. So how is AI influencing that business? 

Nancy Henriquez: Several years ago, I started to see the convergence of IT and HR in, ... large enterprises. And when I started to see that happening, I was like, okay, it's only a matter of time before that trickles down and reaches small business. And the reason, and what is the reason? Why is that happening in larger enterprises?

Nancy Henriquez: Now you bring on AI agents that are coming into play, right? and all of a sudden, IT, who's dealing with technology, is now needing to also train people, on using AI, or how to govern it, right? Yep. and many different aspects of this were just converging, and so I had that idea or that thought of this is going to impact the [00:12:00] MSP space, sooner rather than later.

Nancy Henriquez: And are we prepared as technologists to also be able to manage people? because once we have The AI, in tune to what is- it's needed. Yeah. Now we have to really, tune it up to how humans function. Yeah. and to be able to assist in those ways. And so that's where for me it was like, "Okay, this is much bigger than the last wave of technology that was coming, that was emerging," like moving things to the cloud and things like that.

Nancy Henriquez: and then of course how I use AI personally has been creating that second brain. I named her Claudia because she's- Yeah ... she's based on Claude. Yeah. and then, the, in Spanish it's inteligencia artificial, so it's IA instead of AI.

Nancy Henriquez: and so that's Claudia. 

Michael Cupps: I, and I wanna talk about Claudia as well. the I think you're right that the in- the intersection of humans and agents, the, the... [00:13:00] If you read a lot of the press, it's how AI's gonna replace humans and blah, blah, blah, blah, blah, and there's so much of that out there, but what's really gonna be happening is there's gonna be a blend of these things that work together, and I think you're right.

Michael Cupps: that HR and IT are gonna be partners on this more than they, probably ever imagined is probably- Yeah ... the most, astute, astute, observation because it is happening. And there are some technologists that think we can just do away with humans," and then there's the humans that say, it's gonna be a blend, and I, my I applaud you for f- for making that intersection. I'm sure your customers like that too because I talk to a lot of small businesses. As Enterprise Diagnostics does kind of the exit readiness. And when you start looking out a few years and if you wanna value your business in a way that you can sell it at a premium, you've, the, the CEO particularly has to start thinking bigger.

Michael Cupps: but there's so many little things along the way that have to change or are changing that make you more competitive. So you've hit on a bunch of amazing stories that say, you have to delegate to get better, right? You said it's something to grow. Get- Let it- Give up to 

Nancy Henriquez: growth

Michael Cupps: And that's so true. So do you think that, MSPs are early [00:14:00] adopters of AI, or are they laggards, or not sure yet? 

Nancy Henriquez: They're humans. I think there's a spectrum, just as much as any, any other business.

Nancy Henriquez: And, I find it hilarious when, we're having similar conversations and I'm coming across some that are resistant to AI just as much as, some other, normal people are resistant to AI. Yeah, 

Michael Cupps: yeah. 

Nancy Henriquez: and then there's those that are the early adopters. They're jumping- 

Nancy Henriquez: on board. They have multiple agents deployed. They're helping their clients deploy multiple agents as well. and they're orchestrating, at this point, an entire fleet of AI, agents in multiple ways. And then there's those that are just, you know, really just trying to get their head above water and- 

Nancy Henriquez: not able to think about what AI is, actually able to do or how to even leverage it to help customers and things like that. So we've got the gamut, I think. and so I... But I think that's part of the fascinating aspect [00:15:00] of where we are in time today- is that because of these different pendulum swings, Yep

Nancy Henriquez: I think that it is gonna be a blend of things. It's gonna be, an intersection of human and technology like never before. Yeah. and it's just a matter of, whether managed service providers will be able to help manage that, that technology for their customers just as much as they're managing the rest of the infrastructure and everything else.

Michael Cupps: Yeah. In that respect, it's a huge opportunity for MSPs as well, I think so. Now you've got, you're making this huge acquisition and, Yeah ... we can't mention it by name, but it's related to the MSP community. So tell us a little bit about what- whatever you can share at this point.

Nancy Henriquez: Yeah, it's, it's a backup and disaster recovery business. so this, this business, is a legacy business. It's been around for about 20 years working with MSPs already. and so when I...

Nancy Henriquez: When it was brought to me actually, at first I was like, "It's a backup business." Yeah. "It's a commodity. I don't [00:16:00] know if I want to." Yeah. Yeah. but when they told me, "Just take a look at it," and I saw that it's, it's MSPs that are reselling it currently, I immediately knew, okay, this is meant to be.

Nancy Henriquez: I love to help MSPs grow their businesses. I've been doing it through coaching. I've been doing it through community building. and so this is now another opportunity for me to be able to do that, and, I f- wholly believe in the fact that if I help others grow, I grow with them.

Nancy Henriquez: Yeah. And so that, it's a natural, natural outcome of just being able to grow together. And so that's, that, this business is, I'm looking forward to it. I'm looking forward to- Yeah ... growing it, and to- That's fantastic ... to seeing where we go. Yeah. 

Michael Cupps: So Claudia's an interesting example. I know you're part of the Anthropic, partner program. I'm, I'm not sure if there's a formal name for it, but you're part of the Anthropic, so you're learning and working with them to build solutions for your customers and your own self, and Claudia's one of those functions.

Michael Cupps: We had [00:17:00] a guest a coup- couple weeks ago, maybe a month ago, and he had built a, a, a second brain using Obsidian and some other things and it was for, when you described yours, it's hey, they're doing the same things coming from different angles. So tell us a little bit about Claudia 'cause I'm fascinated by this.

Nancy Henriquez: So Claudia started off as my chief of staff and has continued to develop. Now I, now she fully, I think, more second brain is definitely more accurate of a description. she's doing the menial tasks, everything from triaging my inbox, my calendar, managing my calendar. it, and now the, I was laughing the other day because she was yelling at me.

Nancy Henriquez: And I say- ... yelling at me because I've given her my own personality. Yeah. and so she's now coaching me on time and c- my capacity- Ah ... and, alerting me on certain things. and so I'm having her track not just projects that I'm managing, update me on certain things, and she's got this beautiful dashboard [00:18:00] available for me.

Nancy Henriquez: But beyond that, she, I have her telling me things like, sentiments in meetings and conversations- Yes ... red flags that I should be looking out for, So it, she really has become, Yeah ... almost a second brain. 

Michael Cupps: Yeah. 

Nancy Henriquez: And, my, my oldest, I have a 20-year-old, son who is, very much against AI and continuously tells me, "I'm sorry, mom, but..."

Nancy Henriquez: Yeah. I'm like, "It's okay. It's okay. It's not for you. It's cool." 

Michael Cupps: I hope that someday I can sit down with you and you show me how Claudia works because I've started building mine, but it's not near as advanced as yours. But I, what I really think is interesting is y- you started the show talking about ADHD being a superpower, and what this technology actually has the ability to do is help that, right?

Michael Cupps: Because y- shouldn't have to remember every detail, right? You shouldn't... now we can get there together in a different way, and I think it I think it's a, a fantastic opportunity. By the way, we have a 25-year-old, and she is anti-AI as well. So there's something- ... about that group of people [00:19:00] that are like, "Hey, wait a minute."

Michael Cupps: Yeah. And we need that. 

Nancy Henriquez: that it's using. 

Michael Cupps: we need people that'll tap the brakes on some of, some of the other stuff. but it is an interesting thing, and I'm really fascinated by what you're building. and I think it's important because I think- People are wondering where it f- affects them and how it, how can it help them?

Michael Cupps: It's not just get a Copilot license from your company, right? That's ... A- actually, I think that's almost more disturbing 'cause people don't know what to do with it. But there's a huge opportunity for us all as individuals to figure out where it fits in our lives. It's not for everybody, but where it does fit, and it can take over some of those things that will help you just do more and be better.

Michael Cupps: And I think s- I wrote a book on time management and priority management, so it fits in my world, but I really do believe it's where you put your attention is where y- your life is, right? And if you, if the, you're putting your attention on things you don't really enjoy, then you're wasting time, if you will.

Michael Cupps: So give it to somebody that d- or something that does that, and you can p- put your attention on things you care about, right? 

Nancy Henriquez: Exactly, 100%. I, my 20-year-old would, would tell me, you're gonna lose your critical thinking, [00:20:00] Mom."

Michael Cupps: Yeah. 

Nancy Henriquez: and I'm like, "No. No. That's, 

Michael Cupps: Yeah

Nancy Henriquez: because of the way that I am leveraging Claudia- Yeah ... it's, she's enhancing my critical thinking. She's a- Exactly ... a bouncing board for me. She's allowing me- Yeah ... to, like you said, remove some of the tasks from my brain 

Michael Cupps: Yeah ... 

Nancy Henriquez: I can focus on the things that I should be paying attention to.

Michael Cupps: Yeah. The neural energy we have to spend to multitask is really costly to our bodies, right? And our brain. And if you can, if it ... I just think that actually gets that fuel back into your brain, because it's- Yeah ... something y- you can just rely that it's taken off. Your delegation theory.

Michael Cupps: It, it, when you can delegate it and not worry about it, your brain can focus on the things that you really wanna think about. And so I agree. But I also understand your son's point of perspective, and we have a lot of sci-fi movies about AI taking over the world and stuff. So there's a lot of that out there, but, I appreciate that.

Michael Cupps: So you got Claudia, you've got the book, you've got MSP, MSP Unplugged. I saw something about a conference or something that you, you were picking some music for. Is this something that's on, coming up on your horizon? 

Nancy Henriquez: TechCon Unplugged [00:21:00] is the, annual conference that MSP Unplugged hosts.

Nancy Henriquez: It's, September 17th through the 19th in Chicago. And, w- it's, one of the coolest things about it is that it's a room full of MSPs, peers, that have come together and put together the agenda, the content, and, the conversations that are going in. So it is, I would say, truly a conference of giving, giving- 

Nancy Henriquez: and sharing, and knowledge share like no other. 

Michael Cupps: Good luck with that show as well. And we're up against the time, but I do ask, and I'm afraid to ask this question 'cause we already talked about Claudia, but, we ask every guest a q- a question at the end. It's like, what are you going to take off your plate and give to AI in the future?

Michael Cupps: And I, and obviously with Claudia you're doing a lot of that. But is there anything that stands out that is something you do and, that you're gonna hand off? 

Nancy Henriquez: I'm already handing off. but I would answer that in the sense of now I'm looking at, what can I take off from my employees and- 

Nancy Henriquez: hand to AI. I truly believe that, every employee [00:22:00] should probably be paired with an AI agent at this point in time, of their own. And that's what I'm looking into now is how can I make my employees' lives easier and, have them focus on more, higher value functions than, the tasks that they're doing now.

Michael Cupps: And I agree with you. that is the next wave is how do we assist people to do something, to do more, to do... And it's not to cram more work into it, it's to do the work that fulfills them as well. So that's great. 

Nancy Henriquez: Exactly. 

Michael Cupps: I hope you'll come back and join us again and talk about this, and especially after the acquisition so you can share some more information about that, 'cause I'm really interested in the mechanics of what you're gonna do with that and the, it, to create value over time. So that's awesome.

Michael Cupps: So thank you so much. we pass- we posted the various websites for Sibyl Consulting and the book, et cetera, and we'll post more of that later. If you have any questions for Nancy, please put them in the chat, and we'll make sure she gets them and answers, them if it, even if it's later on. So thank you so much.

Nancy Henriquez: Thank you again so much for having me on, Michael. This has been a great conversation. [00:23:00] I love that. And you know what? When it comes to building habits, what you can do one thing at a time, empower yourself and, absolutely delegation allows you to do that even more. 

Michael Cupps: Said, Nancy. Thank you so much. Everybody, be sure to tune in next week as well, and do like and share, and check out enterprisediagnostics.ai, who's one of our sponsors, or Time Bandit, timebandit.io as well. Thank you so much, and have a great week