B.O.O.S.T. Podcast
B.O.O.S.T. Podcast
Scaling Smart: Ashish Gupta on Leadership, Growth, and Business Turnarounds | EP160
What does it take to scale a business, build a powerhouse team, and navigate uncertainty like a seasoned leader? We sit down with Ashish Gupta—serial entrepreneur, former Apple executive, and fractional COO—to uncover the strategies that have helped him turn around over 20 businesses and drive exponential growth.
From leadership evolution to the future of entrepreneurship, Ashish shares invaluable insights that every business owner needs to hear. If you're looking to sharpen your leadership skills and future-proof your business, this conversation is packed with game-changing advice.
Tune in now and take your business to the next level!
LinkedIn: https://www.linkedin.com/in/ashish-gup/
Website: https://scaleupexec.com/
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There's two types of people that I've seen as an entrepreneur. The first type is that visionary or strategy type of person who can really think about the future, the direction that a company needs to go in. And the second type of person is that execution focused person, somebody who's able to take all these different ideas and visions and boil it down into what actually needs to get done today, tomorrow and the day after. And from what I've seen, 90% of people are not both.
Kelly Leonard:That was Ashish Gupta. Ashish has had a long journey in business and tech, selling two businesses where he was founder level, managing a $2 billion a year budget at Apple, and now running a fractional COO firm that has turned around over 20 businesses. He's an expert at helping leaders and businesses reach their potential. And in this episode, Ashish shares strategies to secure thought leadership space. I'm Kelly Leonard. And this is the Boost Podcast.
Announcer:Welcome to the Boost Podcast, the podcast created to ignite your business and career potential. Whether you're a seasoned entrepreneur launching your entrepreneurial journey, an established business leader, or early career professional, we've got you covered. In each episode, host Kelly Leonard and her guests dive into one aspect of Kelly's signature Boost framework, ensuring you get practical, actionable insights to tips, and takeaways to build your brand, optimize relationships, obtain more leads, secure thought leadership space, and tap into new markets. Get ready for bite-sized, power-packed interviews with entrepreneurs and business leaders. Greatness awaits you. So let's boost together. And now, here's Kelly Leonard.
Kelly Leonard:Hey, Ashish. Welcome to the Boost Podcast.
Ashish Gupta:Thank you so much for having me. Looking forward to this.
Kelly Leonard:And so for folks who are hearing your name for the first time, tell us a little bit more about yourself.
Ashish Gupta:Well, I've been in tech most of my career. I was previously the co-founder of a wireless company. We built it up. It was one of those starting in a garage type stories and eventually did build up. It was acquired by Qualcomm, a Fortune 500. After that, I was in Apple in management, managing a pretty sizable operations team and really learned a lot about leadership and management there. And eventually I had the entrepreneurial bug again. I quit Apple. I acquired a distressed e-commerce business and spent four or five quite painful years in turning every aspect of that business around. from the team, the culture, the operations, the B2B and B2C channels. Eventually, it did turn around. It was acquired in April of 2023. And after that, I had the chance to help several small and medium-sized businesses as a fractional COO. These were businesses where the founders were stuck, the revenues had plateaued, teams were burnt out. And I retooled those businesses within three, four months. Their revenues grew 30%, 40%. And eventually, I had more engagements that I could handle myself and built up a fractional COO firm called Scale Up Exec. And we've got a team of some of the most skilled COOs I've come across. And it's really fascinating just to be able to see the impact you can have in the small, medium-sized business space when you bring in really top-tier folks.
Kelly Leonard:Wow, I love it. I mean, you've had a remarkable career and a remarkable journey with the two founder-level exits and then your senior management role at Apple. So from your perspective, how has your leadership style evolved over the years? And then what are some of the key lessons that you've learned that you think might be helpful to share with our listeners?
Ashish Gupta:Yeah, it's definitely evolved quite a bit. And one of the areas... that it's evolved in that I found to be useful for others as well is that I found it best to not have a one size fits all approach to being a manager or a leader. And what that means is each team member that you have is unique. So it's important as a leader to understand what's unique about them and to not judge any of that. And there's, I guess, three key areas that I try to understand from each team member in order to be a good leader for them. First is what type of work environment gives them energy? versus what type of work environment or work drains their energy. So for example, some people are really energized when their managers are really deeply involved in their work, while others like to just have directional guidance. Second point is understand what they're skilled at versus what they're not so skilled at. So for example, somebody might be really skilled in analytical work, but not in soft skills, and that's totally okay. It's not needed to judge that, but to understand that and now be able to provide them the right environment to let them thrive. And then third is understand what their life situation is currently and how does that impact their personal ambition or goals. So for example, maybe they just had their first child and so their work life needs might be different and that's totally okay. No need to ding them on that. Actually now try and see how you can support them so that they actually feel like there's somebody who cares and understands and that will allow them to thrive in their work.
Kelly Leonard:Yeah, I definitely appreciate the last piece in particular because I think oftentimes leaders Thank you so much. that oftentimes the workplace may not be the best place to support folks who are dealing with just life, just living. Exactly.
Ashish Gupta:And that's where I think one of the differences between a great leader and And a typical leader is somebody that really understands their people that to that level and can support them through that.
Kelly Leonard:Now, has that always been your approach in terms of just even when you think of like these three pillars, if you will, that you just described? Has that always been your approach to leadership? Or did something happen in you over the course of your professional life where you were like, you know what, I've been exposed to so many different leadership styles. And so I'm going to take this element from this person and this from that person and then create my own from there.
Ashish Gupta:I think before I stepped early on, before I stepped into being a manager, I had seen and observed many different managers for my own managers, as well as other leaders. And especially in places like Apple, where it's kind of like a grand central station where a lot of some of the best people in the world come, including leaders. They come through there and then eventually they diversify into a lot of other places. So you get to see what things you like and don't like that you'd want to incorporate into your own leadership style. So I observed some of these things in many different people, and then I started applying them for myself, and I started seeing results. I started seeing that my team members were happier, they were more effective in their work, and were able to accomplish much more.
Kelly Leonard:Awesome. Let's talk a bit about scaling businesses, because I know you've helped numerous businesses scale rapidly, even you mentioned mentioned in your introduction about distressed companies. What are the common some of the most common challenges entrepreneurs face when they are trying to scale and then how can they overcome these obstacles to secure their thought leadership space?
Ashish Gupta:Yeah, I think a lot of this boils down to the entrepreneur themselves. So firstly, it's important for an entrepreneur to be clear on what they actually want. For example, many, many entrepreneurs They think they want to grow their business, but in reality, they actually want a lifestyle business that gives them cash every month or whatever else. And that's okay. There's nothing wrong with that. So it's important to understand, do you actually want growth in your business? Because there is an implication to that in terms of what it demands from you and your team. And it requires different sets of people, different finances and everything else. So let's say if you do want growth and you're very clear and you're honest to yourself that you do want growth, then now you want to understand yourself. So, for example, there's two types of people that I've seen as an entrepreneur. The first type is that visionary or strategy type of person who can really think about the future, the direction that a company needs to go in. And the second type of person is that execution focused person, somebody who's able to take all these different ideas and visions and boil it down into what actually needs to get done today, tomorrow, and the day after. And from what I've seen, 90% of people are not both.
Kelly Leonard:They're
Ashish Gupta:usually one or the other. And if you can really be honest to yourself and assess which of these am I, now you can get help to fill in the gaps of what you are not. So I think this is one of the first pieces of is really trying to understand yourself. And then second, that I've seen pretty much every Every entrepreneur do, maybe not in the best way, is to use their time effectively. And many entrepreneurs, they love to say, I'm so busy, I work 60 hours, 80 hours, 100 hours a week, and I don't have time for X, Y, Z. But most of the time when I really start diving deep into that, to understand what is taking up an entrepreneur's time. I usually find that only a portion of their work is actually needle moving work for the business. It almost becomes a habit to sit in that chair and be there X number of hours every day. But the real effective work might only be a small portion of those hours that you're sitting in that chair. So now it's important for an entrepreneur to think, well, how do I remove the low value work that I'm currently involved in from my plate, shift it off somewhere else so that now every hour that I'm actually here and working, it's effective and needle moving for the business.
Kelly Leonard:That's really good. Yeah, because that is that's so that's so true. Oftentimes we conflate busy work for that more effective work that you mentioned. So thank you for for lifting that up. You mentioned growth in terms of, you know, scale, like actually being clear on what you actually want and whether or not you want to grow or have lifestyle business. And so when we think about growth, share with us a little bit about like in your experience, what are some of the essential qualities of a high performing team and how can business leaders cultivate these qualities to drive success and innovation in their enterprise?
Ashish Gupta:Yeah, that's a good question. Actually, I think a lot of this starts from culture and culture is like one of those words where many people, many leaders think it's just a fluff word. I actually remember going into the meeting, a CEO of a two billion valued company and asked him, what does the culture look like for your your company? And he said, well, there's a whiteboard up there and the it's written. Don't ask me what's written there, but it's written over there. That's our culture. And and I realized that, OK, something is missing here for me. A strong culture is when, let's say, you as a leader are not in a meeting that your team members are in. You actually will know without having to be there how your team members will make decisions, how they will think and process things, and eventually what the outcome might end up being. That's when you know that there's a really strong culture in a company. A culture evolves as the business evolves. For example, at some point in your business, you might not need innovation in your culture, you might instead need a really well-oiled machine. And if you have innovation in your culture, that actually might slow things down. But maybe there's a future time when innovation actually might become relevant. So it's important to understand right now what is actually needed and for the near term, what is needed in the culture of your company. And I like to define culture as two things. One is values and second is behaviors. So for example, a value might be teamwork and a behavior that exemplifies teamwork might be like, let's say when you see a team member is working on something that you have knowledge in, you will actually reach out to them and offer your support in ensuring their success. So that might be a behavior that defines a value. And so for a company, you'd want to, for your culture, define a set of values, maybe two to four. And then for each of those values, define maybe three to five behaviors that exemplify those values. And now once you've defined that, firstly, you as a leader should be the best model of those values and behaviors. And then it'll start flowing down into the rest of your team. And then you can actually implement it into or incorporate it into a lot of the processes that your team has every week and even reward people in performance reviews if they've modeled that culture.
Kelly Leonard:Okay. I would be remiss if I didn't like sort of also when we talk about leadership and when you think about uncertainty and particularly like right now, given the current economic climate, I would love to hear from your perspective What strategies you would recommend for entrepreneurs and small business owners to navigate uncertainty and to maintain their leadership positions as well?
Ashish Gupta:Two things come to mind. First is optimize and second is optionalize. So by optimize. I mean that optimize for speed to profits and building a cash reserve. So if you focus your business purely on growth instead of profits, let's say a downturn comes about in the economy, you might not be able to make it through. So really try and optimize for building profits in your business as soon as possible. And even if you have cash on hand and you have reserves on hand, spend it as if you had less. So for example, you can go through your bottom line and see what are all the different cost points, renegotiate supplier contracts, see if there's labor intensive tasks that you can quickly cut out or semi-automate. Are there team functions that you can offshore to lower cost places rather than having them here? So like that, you know, go through your bottom line and see are there ways that you can optimize there? And on your top line, are there growth investments that are showing low results that could be cut out? And so even go through on your growth areas and see, are you really spending every dollar the best that you can? And then our second point was optionalize. So let's say this might be around, let's say tariffs have a chance of impacting you because your supply chain might be based in high risk countries or with high risk suppliers. So now let's look at what are the different options that I have, assuming that a certain policy gets instituted. So if a tariff gets instituted that affects my supply chain, now can I shift to... lower risk geographies or suppliers and already start thinking through that and building out those options.
Kelly Leonard:Awesome. Thank you for that. Ashish, this has been really, really helpful conversation. I appreciate your insights. If folks are listening and want to tap into all the great work that you're doing, what's the best way for them to reach you?
Ashish Gupta:Yeah, best way is scaleupexec.com. That's my website. And on there, you can directly book time with me. I'd love to, even if you're not looking to bring on fractional execs to your team, I'm just happy to look at are there ways that I could help your business in different ways or just with ideas or analyzing it. So I'm an open book here. So feel free to set up time with me through scaleupexec.com.
Kelly Leonard:Awesome. Thank you for your time today.
Ashish Gupta:Yeah, this is great. Thank you.
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