Welcome And The Big Question

Tom DuFore 0:01

Welcome to the Multiply Your Success podcast, where each week we help growth-minded entrepreneurs and franchise leaders take the next step in their expansion journey. I'm your host, Tom Dufour, CEO of Big Sky Franchise Team. And as we open today, I'm wondering as you are scaling your company, are you making sure you're doing as many of the things that give you energy as possible and that you're skilled at? And what is it that brings you the most joy or satisfaction in your business? Well, our guest today is Ashish Gupta, and he shares with us some best practices for sorting out your transition from operator to CEO. Now, Ashish is the founder and CEO of Scale Up Exec, where he helps founders and CEOs scale their businesses by installing world-class operations, systems, and leadership. He has built and exited two companies, including one acquired by a Fortune 500 company and previously operated at Apple, where he gained firsthand exposure to elite execution and operational rigor. Ashish is known for his practical, no-fluff approach to leadership, execution, and sustainable growth, helping entrepreneurs build businesses that deliver both financial success and personal freedom. You're gonna love this interview, so let's go ahead and jump right into it.

Ashish Gupta 1:17

Firstly, thanks for having me here. I'm very uh excited to talk with you. My name is Ashish Gupta. I'm the CEO and founder of ScaleUp Exec.

Tom DuFore 1:27

Perfect. Well, I love this concept of Scale Up Exec. It just sounds fitting for our audience because that is what we help our clients do is scale through franchising and scaling and growing through that. And one of the things, and why I was interested to have you on the show, is this topic of founder psychology and really making that shift from the operator of the business to the true CEO, not just in title, but actually in really executing and running the business. That's a pretty broad statement, but let's start talking through that.

Operator Versus CEO Defined

Ashish Gupta 2:01

So, first it's probably good to define what is an operator versus, at least in my mind, what what is a CEO. So an operator is typically what I see most people who start a business, they're often having their hands in a lot of different things. They're of course working on the product and the service, eventually even taking care of their customers, eventually even doing things like bookkeeping or they're they're just hands are deeply involved in a lot of different areas, especially their hands are involved in decision making, not just high-level strategic decision making, but even day-to-day strategic and execution focused decision making. So an operator is usually somebody who may have even started off at that role. And as the company grew, they may never have let go of those roles. So that's an operator. Second is what is a CEO? I feel like a CEO is somebody who's been able to, at some point, transition from having all of the key decisions being made by them, a lot of the key fires that are happening be solved by them, to now instead having a team in place that they can trust and that understands how they think, understands the way that they would like to make decisions, and have imbibed that and are now able to be the torchbearers of decision making themselves. And the CEO knows and has trust that, okay, if my team is in place, they know how I think, they know how I'd like to act in if I was in their shoes. But I have trust that they're going to make the right decisions without me having to be involved. So now a CEO is where they've let go, but have all the right metrics in place, accountability mechanisms in place to make sure things are still going in the right direction. So I think this is first is just definitions. Does that does that resonate to you as well?

Decide What You Want

Tom DuFore 3:47

Those definitions are fair and accurate. I think that's really, really good. Let's talk about, I guess, a little bit of that transition from that operator into that CEO from one definition to the next. It's not like a light switch, right? It just doesn't happen one day, right? I'm guessing there's a little bit of time in between. So let's talk about this transition time and starting to transition from day to day, or even just, I guess maybe even for an owner, maybe assessing where they are in this journey and where are they in between those definitions.

Two-Week Time Audit Method

Ashish Gupta 4:21

So, first thing is I think it's important to know what is it that you want in your business and your role in your business. For some people, their goal is not to have a fast growing corporation where there's a growing team and a growing revenue and profit and a structure and entity and vision for the future. Some people are very satisfied to have a lifestyle business where it's steady, that generates some amount of cash flow for them personally, and they're satisfied with that. And they may even have an interest to be involved in uh hands-on in different areas of the business. So I think it is important to understand what is it that is your goal for the business, and then what are the things that you're really interested in doing and are uniquely skilled at doing? For many business owners, they think that, oh, if I'm a business owner, that means that I eventually have to become the CEO as well. Or maybe I started a CEO and I have to continue as CEO through the life cycle of that business. It's actually important to figure out is that what you want? And is that what you're uniquely skilled at? Are you actually skilled at being a CEO? For many owners of businesses, they may actually be skilled in doing some technical work. And that might be their unique competence. And it's not necessary for them to be the strategist or the visionary of the business and hence the CEO. So, and I think that's totally okay. It's good to you know take some time to analyze yourself and where what you want, number one, for the goal of the business. And number two, what are what you're uniquely skilled at and get motivation and energy by doing. And then now you can make a decision that, okay, do I actually want to get my hands out of the day-to-day of the business? Or maybe I actually want to be deeply involved in, let's say, product development, because that's where my unique skill set is. And maybe I'll bring in somebody else to operate as the CEO. Just because I'm owner doesn't mean I have to be the CEO. Sometimes it's actually a disservice to the company if you continue operating as a CEO. I didn't mention too much about what we do. We're a fractional CEO company and we jump into a lot of different small, medium-sized businesses where there is this transition happening where an operator wants to turn into a CEO. And many times we actually find that people have enough self-awareness to know that if I go from being an operator to the CEO position, the business is going to suffer. I'm not a really good leader. I don't know how to motivate people, but I'm really good at XYZ in the company. And so maybe I'll just double down in that and I'll bring in somebody else to do the CEO work or the COO work. And that's great. You know, like when somebody has that level of self-awareness, now you can really work with that and create the right structure and create the right team to enable that company's success. And then for many other businesses, we find that they they're very happy to be a lifestyle business and they're happy with the way things are currently operating. And then there's a third case where there's folks that know they have that unique skill set of being a CEO. They have the vision, they can see what they want for the future, they can put together strategies to try and get there. Now maybe they just need the right pieces in the leadership team or in their structure or in their operating procedures to help realize that vision. And so they actually make good candidates to be a CEO. But now it's important to figure out how to get things off of their plate. So let's say we are operating in this third scenario where somebody has the capability and skill set and interest to be a CEO. I usually like to do an analysis. Uh, have them for two weeks understand all the activities that are falling into their plate at the moment. And it could be in a simple spreadsheet. So it could be a simple spreadsheet where they just track, okay, today I did this activity, activity B, activity C. And now for each of them, it's important to grade that activity in a few different things. Number one, is that an activity I was uniquely skilled at doing or not? Number two, is that an activity when I did it, I felt energized? Or did it actually deplete my energy? You know, sometimes we're really skilled at stuff, but actually when we do it, it's like a drain, you know, it feels like a drag. It's not something we'd want to keep on doing, even if we're good at it. And then third is, is this an activity that really moves the needle for the business if I was specifically to do it? So I think these three categorizations are quite important. So now if you, for two weeks, do all of this analysis just to see where your time is going and if it's something that builds your energy, you're good at, and actually it's important for you to do it in the company. Now, after that, you can make a few decisions. Some of these activities you might figure out nobody in the company should be doing this. It's not actually that valuable. Secondly, there might be activities that, okay, it's important for it for this activity to happen in the company. But me as a CEO, I don't have to uniquely be doing this activity. Like, for example, let's say bookkeeping or finances. You know, that's one of the typical things a lot of CEOs, when they're going from operator to an executive, that they keep their hands on just because they're used to doing it. Or maybe they don't have enough trust in other people to start doing it. But it's typically not a good use of time for a CEO to be doing the books or being so hands-on in that stuff. So that would be the second type of activity is the things that somebody else can do in the company. It's still important to do, but somebody else in the company can do. Then third is okay, here's a set of activities that actually it's important for me as CEO to continue doing. And I'm going to continue doing those hereafter. So now once you've got this kind of self-analysis, now you can actually start making decisions. So you'll start cutting out some things, you'll start figuring out can I delegate a few of these activities that fell in that second bucket? And who's really good at being able to take this over, who I trust. And I'll create all the right training mechanisms and I'll create some accountability mechanisms to make sure it's delegated off well. And then thirdly, there'll be the set of things that you're going to keep on doing. And now you'll start actually over time transitioning into a true CEO role.

Tom DuFore 10:20

As the business oftentimes is in a transition as well, where they're growing, the revenue's expanding, but maybe staff hasn't quite backfilled, or there's not enough cash there yet to bring in, probably part of the reason you exist for fractional COO work and others. But how do you work or as an owner for someone that's listening in? I'm thinking, well, okay, that's all well and good to bring in these people or pass off this work. But what happens if those people don't exist yet, or the talent of people don't exist? Maybe you've had some great managers or general managers to run daily operations, but you don't know if you have someone that's maybe at quote a vice president or C-suite type of level. And maybe you can't afford someone or don't even know where to start to bring someone in. So talk through that a little bit.

Offshoring And Fractional Executives

Ashish Gupta 11:11

Yeah, that's a really good point because I think in every small, medium-sized business, your finances you make a lot of decisions. And you're exactly right, you might not be at the phase yet where you have enough cash flow or the prospect that that's going to continue coming in to be able to make the key hires that you need. And also in some industries, like let's say some traditional industries, if you're like a one, two, three, four million a year business, it might be very difficult to access very top-tier talent, let's say if you're a construction business or like something that's not tech or you know, sexy like that. So it even if you do have cash and you're willing to spend it, it just may not be possible to get access to that level of talent. So this is some of the decisions that you do have to make. You ideally you'll see, well, can I simplify things in my business? So like it basically cut out things. So let's say people in my team are not yet at the capability that are needed to make XYZ type of high-level decisions, and I don't yet have the cash to be able to bring in somebody of that skill set who can make those kind of decisions. Is there a way that I can have a hybrid solution for the interim? Like, is there things on my own plate that I can strip away so that I do have enough time to make these important decisions so other people in the team don't have to? Or can I take some subsets of decision making that I can delegate off to people, maybe the ones that are not as critical decision-making tasks? Can I, are there certain people on the team that I can train up and upskill just enough to be able to have ownership over making decisions on these not grand areas, but maybe subsets of that? So it is possible to start going in that direction. And then the third is I think now more and more companies are are very comfortable with offshoring, not just for in the past, we would offshore just for, let's say, uh individual contributor roles like graphic designer or video editor or something like that. You know, something that we wouldn't think is too deeply critical to the to a business. But now people are starting to get comfortable with offshoring even more executive-level decision making. So you could go to Latin America or maybe Eastern Europe, depending on what type of job profile it is that you're looking for. Like, for example, in Eastern Europe, people are very technically skilled. In Latin America, people are very skilled with soft skills, such as sales or customer service. And there's countries like the Philippines where there's really good virtual assistants or customer service representatives, or even with bookkeeping and taxes. So, you know, you can in these countries, you can actually get access to good talent at much more affordable compensation structures. So it's possible to, and then of course, the fourth mechanism, which is what we're now looking at at Scale Up Exec is fractional executives. It's typically hard to get access to really top-tier talent on a full-time compensation level. But if you hire somebody who's really top-tier, who's like scale businesses from zero to nine figures again and again, gotten them to exits multiple times, have been executives at startups as well as large enterprises. It's usually hard if you're less than 100 million a year type business to get access full-time to that type of talent. But let's say on one hour a day or two hours a day in a fractional capacity, it it's now actually possible to get access to that kind of talent. So that ends up being a more affordable mechanism of getting that executive mindset and strategy and direction in a in a bit more affordable way.

Tom DuFore 14:40

That's very, very helpful. So thinking about some of this transition, you've given some, I think, some very practical steps and pointers here. Is someone starting to transition out? Are there maybe some best practices or maybe things to be aware of or avoid as someone starting to kind of make that shift or start to be intentional about it? That might be a better way to phrase it.

Ashish Gupta 15:07

I think maybe a couple of the points that we that uh I touched on before, but I'll try and put it together. So first is make sure you know your finances, what you can afford and can't afford. Secondly, that's self-awareness, what you're really good at and uh what gives you energy and what you're not good at and what doesn't give you energy. So you now start coming up with a scope of what are the things that you should keep in the company and delegate off to somebody else. Now, thirdly, you understand who in the team has that capability and skill set that you can trust. Either they have that skill set already or they have the capacity to upskill themselves if you were to train them and guide them and coach them. Is there somebody in the team that you can pull up to that position to start taking on some of these activities that you think are important for the company? And it might be multiple people, you know, not just one person. So let's say it is in that same same example of bookkeeping. Bookkeeping is likely a skill that you can easily get part-time at a reasonable cost structure for you to be able to delegate off. And it's important to do, it's needed. So let's say you've identified now people already in your team that you can upskill and transition off some activities too. Then the next thing is you need to create a delegation plan that actually will enable their success through this whole transition. It's a lot of people, they might think of delegation that, okay, here's the task. Now I'm gonna give it to you, figure it out, and make it happen. And tell me if you've run across any issues. That's typically what I hear in delegation plans. But that doesn't necessarily give confidence and trust it to somebody and to make sure it doesn't enable their success. So what I like to do is you first, all the things in your head of how you approach this task, uh, you try and jot it down in some bullet points. Then you come up with a few KPIs in there, key performance indicators. Is there a couple of metrics in that activity that if you were to track in data terms, you would know if that activity was being done successfully or not? So, like for example, with bookkeeping, if you know that uh all your finances or your books for every month are closed by the fourth of the month, fourth of the following month or fifth of the following month, then that could be one metric that you keep track of, like how long it takes to close books. There could be other metrics around number of errors or you know how clean those books actually are. So, like that, you come up with a few metrics that are easy to track that you can establish in order for you to figure out if something is going on track or not. Then now thirdly, you come up with a training plan. So this could be you over the course of a week or two providing every every day 30 minutes or 20 minutes or 15 minutes, some coaching or training. And then you provide that to the team member. The team member, then maybe you can watch them and observe how they do that activity and make sure you can give some guidance as they're doing that work real time. And then you, these KPIs that you established, you train them on those KPIs and then now enable them just keep track of those KPIs. And then after you've trained them, it's important to also have regular check-ins. So let's say once a week or for a couple of weeks, you check back in and just see, okay, now that they're doing the activity, do they have any questions or thoughts or any extra guidance that they might need? And then once you feel confident over, let's say, the course of several weeks, you've given them enough training, you've done some follow-on support, and you've got these KPIs in place. Now you monitor with the KPIs. Are things in on track or not off on not on track? If they're off track, now you can meet them again and figure out what the problem is and how to solve that. So I think like this is an example of a delegation plan, but it's important to have something like this in place so that you do enable somebody's success.

Tom DuFore 18:52

That was very, very helpful and succinct. Thank you for sharing that. And Ashish, I want to learn more how you might be able to help me with this. What's the best way for someone to get in touch with you or learn more about what you're doing?

Planning For Upside And Downside

Ashish Gupta 19:05

Probably the easiest place is our website, scaleupexec.com. Uh, on that website, you can actually book some time with me. If you I'm happy to, even if you're not necessarily seeking a fractional executive to come onto your team, but you just want to get some ideas or bound some ideas about a problem that you're facing in your business, I'm happy to be a point of resource. I've now seen quite a few things through the years, and I myself have skilled several businesses and gotten them to exits and also seen a lot of the ups and downs through that journey. I hopefully we'll be able to support you in in your transition. So I'm happy to be available and and meet with people. I've had many misses and many successes as well. So it's I think through each of them, and especially the misses, you learn a lot. Maybe one of the one of the learnings that I had maybe a couple of years ago that has impacted me deeply till today. I've generally been an optimist. And I think as an entrepreneur, most entrepreneurs are optimists. The future is always rosy. Yeah, the future is always very bright. I've had times where I was close to bankruptcy. I was very in a very dire situation in the business because it didn't go as I'd expected, and I'd taken decisions, assuming too heavily a rosy future. Since then I've become much more regulated in how I make decisions. So I whenever I make a decision that's a large decision, I always make sure to think not just about, okay, if this decision goes in the positive direction, what will happen? But also think about if this decision goes in a direction I would not have expected or would not have planned for. Do I have all the right backups in place? Have I, let's say, do I have enough cash in place if this decision doesn't go in the right direction? So making sure I'm thinking not just for the positive, but even for the negative situation. And it's okay if it goes in a negative situation because I've already planned for it now. I know what to do. I'm not gonna get unnerved because of it. So I'm always trying to now think on both ends of the spectrum with when decision making.

Tom DuFore 21:19

That's great advice. And let's look on the flip side. Let's look at a positive, right? Uh win or a highlight, a make or two.

Ashish Gupta 21:28

Yeah, I've had uh several. I've uh a couple of companies I've had, they've scaled quite quite interestingly and have gone to successful exits. Maybe more recently it was kind of interesting. I just got some email and I thought I I thought it was a spam email, but end up getting a CEO of the year award in the fractional executives industry. So I was quite surprised because for me, I've not had any goals of trying to achieve XYZ and this. I just wanted to see if I can share something relevant and help other businesses grow. So it was it was nice to see that that is actually being. Making an impact than being recognized.

Self-Awareness As The Multiplier

Tom DuFore 22:02

Very, very nice. And congratulations on that, by the way. Well, let's uh talk about a multiplier. The name of the show is multiply your success. Have you used a multiplier to grow yourself personally, professionally, or organizations you've run?

Ashish Gupta 22:16

There's so many different multipliers that can exist, but one of the most important actually ties into some of the things I said before, which is which comes from the root of self-awareness. If you know what you're interested in, skilled at, what you're not skilled at, what drive gives you motivation, what depletes your energy, if you understand these things, that itself will help your decision making in terms of what role you should be playing or not playing, what uh direction your business should be going in or not going. Let's say, for example, you've just had a your firstborn baby, and now your life has changed, your life situation has changed. And now your goals and your ambitions for your work have changed. That's totally okay. It's completely okay. And now you, if you know that and you have that awareness, now you can start making appropriate decisions with how you structure your company rather than feeling bad about, oh, I want growth, but actually I want to spend time with my with my baby. So it I think that can be a huge multiplier in the trajectory of your business and not just the business, but even how you feel. Do you feel content or do you feel like regret? Yeah, just that self-awareness, I think, is quite important.

Success As Contentment

Tom DuFore 23:23

Oh, well said. Well said. And the final question we ask every guest is what does success mean to you?

Ashish Gupta 23:30

Maybe a bit unusual answer, but I've seen now personally crazy highs and crazy lows through my journey. And I've seen lots of money and very little money. I've realized that probably all of those things, especially finances, don't mean as much as you previously used to think before you had it would mean. And so I think what's more relevant for a success, the definition of success for me is contentment. Am I contented? If I'm truly contented, then that feels like a successful life. That means I won't have any regrets. Yeah, I'll just be satisfied. And like a deep sense of satisfaction or contentment, I think would be a great definition of success.

Tom DuFore 24:09

Ashish, as we bring this to a close, is there anything you were hoping to share or get across that you haven't had a chance to yet?

Key Takeaways And Closing CTA

Ashish Gupta 24:17

I think some of these key points, and especially around self-awareness, most people in business they immediately start thinking about finances and numbers and metrics and goals and KPIs, but very few think about themselves and especially how their business interrelates with their personal life. As a business owner or CEO, your business life and personal life are deeply intertwined and one impacts the other. If you're having a good day at home with the family, then it often leads to a good day at uh work or vice versa. If you're having a tough day with at work, it can lead to a tough day with your family as well or friends and loved ones. So I think it's really important to think through how your business life and personal life intersect and that there's a common goal between them, a common direction that you're going in that suits both those aspects of your life. And a lot of that then ties into that self-awareness aspect of really understanding yourself and being okay with that, being okay with who you are.

Tom DuFore 25:12

Ashish, thank you so much for a fantastic interview. And let's go ahead and jump into today's three key takeaways. So, takeaway number one is when Ashish talked about what is it that you want in your business? And he said, Some people are satisfied with a lifestyle business, some might want to have a hands-on interest in the business. And he said, figure out do you want to be a CEO or not? And just because you are the owner does not mean that you need to be the CEO. And that's okay. Takeaway number two is that he asked questions of saying, what are you uniquely skilled at and get satisfaction from in your business? Do you have that capability or interest in being the CEO? And this ties back to the first takeaway where he said, think about what tasks and duties will be occurring. And are these skills or tasks that I have skills in or activities? Are these activities that give me energy? Are they important to me in the company? Can I delegate this to someone else? Just great points to be thinking about. Takeaway number three is when he gave us some points to think about beyond and starting to take this next step. And a simple one might be just knowing what you can and can't afford and thinking about how to transition these activities or duties as you're currently doing to someone else and making sure that you're putting metrics in place that are easy to track and follow, to come up with a training plan, to have regular check-ins and monitor with KPIs. And now it's time for today's win-win. So today's win-win is when Ashisha talked about his multiplier. And he said, for him, it's really self-awareness. And I thought that was a great summary, self-awareness. And he said, when you understand the things that you want and don't want, it gives you that great clarity to know what direction to go. And he said, sometimes those priorities change. For example, you have a life-changing event such as your first child being born, maybe your priorities change. Maybe you no longer want to build a large multinational billion-dollar plus organization and you're okay with the lifestyle business. That's okay for things like that to change over time. And so that's the episode today, folks. Please make sure you subscribe to the podcast and give us a review. And remember, if you or anyone you know might be ready to franchise their business or take their franchise company to the next level, please connect with us at Big Sky Franchise Team where you can schedule your free, no obligation consultation. Thanks for tuning in, and we look forward to having you back next week.