Living The Red Life - How to Deliver Bad News & Still Win in Business

Episode Date: March 3, 2025

SUMMARYMahesh Guruswamy, a seasoned tech leader and author, joins the podcast to share invaluable insights on entrepreneurship, business strategy, and hiring for success. With a background in major tech companies like Amazon, Mahesh has a unique perspective on what it takes to scale a business, the common pitfalls entrepreneurs face, and how to build a winning team.Throughout the episode, Mahesh dives deep into the importance of market research, why competitor analysis is crucial, and why being first to market isn't always the best move. He also shares hard-earned lessons from his own entrepreneurial journey, including financial struggles and how he turned them into a driving force for success. Whether you're a startup founder or looking to scale your business, this episode is packed with practical advice you can apply immediately.CHAPTERS02:35 - The Harsh Reality of Entrepreneurship05:10 - Why Most Entrepreneurs Skip Market Research07:45 - How to Identify a Winning Business Idea10:20 - Why You Shouldn’t Always Be First in the Market12:55 - The Power of Competitor Analysis15:30 - Hiring Your First Tech Person: What to Look For18:05 - The “Plumber” Approach to Early-Stage Tech20:40 - The Biggest Lesson from Amazon’s Work Culture23:15 - Overcoming Financial Hardships & Learning from Failure25:50 - How to Deliver Bad News & Still Win in BusinessGUEST DETAILSWebsite: MaheshGuruswamy.comBook: How to Deliver Bad News and Get Away With It (Available on Amazon, Barnes & Noble)Connect with Rudy Mawer:LinkedInInstagramFacebookTwitter

My name is Rudy Moore, host of Living the Red Life podcast. And I'm here to change the way you see your life in your earpiece every single week. If you're ready to start living the red life, ditch the blue pill, take the red pill, join me in wonderland and change your life. Hello and welcome back to another episode of living the red life. Today, we're going to dive into the world of tech and how to use tech to actually grow companies faster.

The only me today is one of the world's top experts on that. Uh, behind the scenes running the tech of some of the biggest companies on the planet, Kickstarter, Kajabi, Amazon Alexa. Uh, so no one better to answer that question and talk all about the tech side of what we do in entrepreneurship and business. Mahesh, welcome to the show. I've been a mirror. Good. of what we do in entrepreneurship and business. Mahesh, welcome to the show. Happy to be here. Good. So I set you up for hopefully success here, some big boots to step into, right? Some of these big things you've done a lot. But if someone doesn't know who you are, do you mind just giving a

minute overview of yourself? Yeah, sure. Sure. So my name is Mayesh Guruswamy. I'm currently the CTO of Kickstarter, been in the software development space for about 20 some years. First 10 years was individual contributor, middle level management. Last 10 years have been in executive roles. So work for pre-IPO companies, IPO companies, early stage startups and everything in the middle. IPO companies, early stage startups and everything in the middle. And uh, great. And you know, you work for some of the biggest companies on the planet, so I want to start there, like, what are just some of the biggest lessons from work, not even tech lessons, just general, like, from working with these like super high performing billion dollar

brands? billion dollar brands. I think the single biggest lesson that I've learned is don't start with the no. Don't start with no, it is not possible to do x, y, and z. I fired tech people over that one exact thing in my life because it kills creative energy as an entrepreneur and a founder. That's exactly right. That's exactly right. This is exactly right. And you know, the most successful companies that I work for, Amazon, Kajabi, Kickstarter, have all been, you know, slightly crazy, right?

You have to be a little bit crazy to believe that you can do the things that these companies pulled off. I really have to be crazy. I sound delusional because I believe in my ideas so much. It's a borderline insane. As I tell up and coming leaders, up and coming executives, don't start with the no, especially if you have aspirations to get into the executive C-suite, you cannot tell a founder no. You cannot tell a successful CEO, no, you can't do this. With enough money and time, I can

move the planet. Right. Yeah. And that's the attitude you should have. Yeah. That's what I tell them too. You know, like you're obviously probably a smarter tech person than many that I've had to hire and fire, but, uh, every time, you know, that's, it's probably

like one of the biggest disruptors to me when someone says that in my team. And I always, you know, my staff know I have this ongoing kind of joke. Now, if anyone says no, I always say, so you're telling me Elon Musk can fly to space and bring a rocket straight back, but you can't integrate and zap this data thing here. It's so funny. Yeah. It's so funny.

Cause I've used the exact same analogy with my teams too. You says, if somebody tells me this this take me six months or nine months like Elon has spent rockets to like space in that time so why can't we get this thing done like sooner so I'm with you. Well I like that and look but I think let's talk about this for a second because that is the difference between winners and losers in business and I think overall why if is a lot of people are looking at what can't happen or what could go wrong or why it can't happen but the most successful people on the planet are looking at how can we make it happen right and how do we look at it all.

It's a mystic setting versus a pessimistic setting. That's right, that's right. I think Archimedes said this right, the long enough lever you can move the earth. So I believe in it. Yeah. So how do you juggle? Let's, you know, it's a great transition because I do think the hardest part with entrepreneur and tech is that, uh, you know, you need to have that crossover and great teamwork, but the entrepreneur has a million ideas and some of those ideas.

I always joke with my team. It takes me five seconds to come up with an idea and then like 50 hours or 500 hours to build right? So how should entrepreneurs work with their tech scene? Well I think my my usual MO is doing a little bit of research up front with customers because you know I have a thousand ideas and like 90% of them could be garbage. That's the thing. So I don't mobilize my team to go build something until I have some level of conviction that this is going to work for our customers. So I talk to customers. I always have a small group of motivated customers who I can go to and ask feedback from.

And if it's directionally the feedback is positive, then you build something which is like an MVP, it's like duct tape and you know, like a small thing that you like get it out, test it. And if it works, then you release it to the entire world and keep scaling. I don't believe in building a Ferrari and then trying to sell it. I'll like build a Pinto and then see if there's an interest in it and then like scale it up to something much more expensive. Yeah. Or what we do and what Elon does is you build the like a fake model of a Ferrari or a moth

of it and then build it with the money that you made from pre-selling it. Right? That's right. That's right. And I do think, you know, tech and especially, you know, I've owned and co-owned and had equity in a few software

companies, but never been like main company. Like I've always sold products that I think are faster, you know, courses, coaching, education, communities, supplement, e-commerce, right? And I've done pretty well. I, supplement e-commerce, right. And I've done pretty well. I've scaled e-commerce to a million dollars a day.

So big numbers. Whenever I've been part of a software company and I've done a few iterations, I've always found it's like, as a marketer, I'm like, Hey, we need these 10 things to sell this, better hooks and unique selling points. And then the tech team, you know, and the software companies at least are like, Oh yeah, we'll put that on the two year roadmap. Right. So how do you balance that for software companies?

Well, I think it, uh, I think it comes down to prioritization is, is what I would say. There's always going to be a thousand different things to do. So as leaders, you have to like realize what is most important and, and figure out like what to put it in the top of the list and what to like put at the bottom of the list, I think the other dynamic that's playing out in, I know my network will hate me for saying that is software development is becoming commoditized faster and faster and faster, right? It is not a hard to learn skill as it was 10, 15 years ago.

So, and if engineers and product managers and everybody else in tech feels like they have special skills, that's who you could think a reckoning is coming. So I think it's like everything now, like, you know, we were talking with my team, Mark's team today, we went from nine poppy riders to two. All right. With more than ever because of AI and my design team, like even me now in Photoshop, it's like, Oh, I really love this photo, my video team creative team took, but it needs to be portrait for, for Instagram or I can just drag it in

Photoshop and click AI generate. And it now creates the sky and the ground. So I see it, whereas that would have been a two hour Photoshop edit from my designer before. So, you know, and this drives, I always talk about Amazon where you live in a world where everyone wants stuff now they want it. Yeah. Instacart.

I get my groceries now. Uber eats. I get my food now. Uber. I get a taxi now on Netflix. I get to watch my movies now, killed by. I think it's going to be the same for everything that comes after that easy consumer stuff

is like, well, software, there's out the box solutions now and you don't have to custom code it all from ground up maybe, right? So that's right. That's right. That's right. And this like, I think software teams have, you know, aversion to sometimes buying something off the shelf and like deploying it, and I actively tell my teams, let's get it out, let's get feedback and see, see how it behaves in the

market before, before investing too much time in it. Uh, so it's a hundred percent right. I think as long as the U S is a consuming economy, it's always going to be, I want stuff today, I don't want to wait. I think it's always going to be that case. It's going to get, I think it's going to get worse because it's like, they're going to have Amazon drones dropping stuff off, more stuff off online, right? So it's really, is going to do more for you.

So I mean, it's actually going you get way more aggressive, uh, next couple of decades, and then it will maybe balance out, you know, that you're going to be able to isolate the other day, you're going to be able to fly from London to New York in an hour and a half, right? Yeah. I believe that. I believe that. So, so back to the tech side, what, what are some of the biggest, um, you know, lessons from, uh, being part of these companies growing, right?

Like all things, like if you were starting out as an entrepreneur now, you've worked in some of the best businesses on the planet with probably some of the best people on the planet. If you were an entrepreneur that's brand new, what would be some general tips you've seen from these companies growing? Yeah, I'll start with Amazon because I think Amazon had a profound impact on me as a person and as a leader. The secret sauce for Amazon is its leadership principles. So I think everybody looks at the output of what Amazon produces, but the way the teams behave is in lockstep.

And a lot of it, like a hundred percent of his guided by the leadership principles, which is if you go to the Amazon's career side, there's like a 10 or 12 leadership principles, I think they've changed it over the years, but like dive deep, deliver results, think big, disagree and commit. Like every single person at Amazon behaves the same way. And it makes it very, very easy to ship software. Everybody thinks the same way. So I think the leadership principles were a reflection of Jeff from the earlier days and his executive team. And a lot of that is funneled into like the way Amazon behaves and builds products. So that's number one, have a strong set of,

you know, like, like for example, you have a company, so you should have like a list of tenants for your team. This is how Rudy thinks. This is what made me successful. And I want all of you to behave like this and you will even recruit people who will sort of show those skills. That's number one. Uh, the other one that I think you mentioned it, uh, Kajabi's

secret sauce is its community. It is a, you know, they have, there are raving fans who like, gather together to talk about Kajabi and how to use the product and how to make like your first sale, how to build your first email list, et cetera. And Kajabi pays a lot of attention to that community. So any entrepreneur, if they want to be successful in selling products or services or their own time, they have to build a community.

Without community, nothing exists today. So that I would say is Kajabi. And Kickstarter, I think the biggest takeaway for me is, you know, Kickstarter came about in a time when it was hard to fund arts projects, music projects, etc. And Perry and the founders, they're like, well, we don't believe in traditional venture capital funding. So we're going to do this other thing. And so think outside the box. Like, you know, you don't have to pattern match because every other leader or executive or company is doing the same thing. And, you know, resist against pattern matching

and do something which is creative. So I would say, have a strong sense of what made you successful and make sure you build your team the same way that exhibits those same principles. Pay attention to community and threes go against the grain grain is what I would say. Yeah.

So I love that. A follow-up question, which maybe it's a question out of those three big companies, right, including Kickstarter now, what's one principle that you've seen across all of them that you would bear in pretty much every big billion dollar brand or successful company? I would say obsess over customers is what I would say is the common theme across all these companies that have made them successful. Like work, start with the customer and work backwards. Like what does your customer want? What are their pain points? What do they wake up thinking? What do they go to bed thinking? And if you understand that, then you can basically build billion dollar

brands and that's how Amazon did it. That's how, you know, all these other companies did it. But let's go down that rabbit hole a little then. So how do I start? How do I do that? If I'm a new entrepreneur? I would say, you know, I advise a lot of startups on the side. So people ask me advice on, Hey, I'm building this product.

Like, what do you think about this? And my, my advice to all of them would be talk to your customers first. If you can't find 10 people to give you feedback on your idea, you're probably not going to be super successful as an entrepreneur, right? idea, you're probably not going to be super successful as an entrepreneur, right? So find those 10, 20, 50 fans of yours or free idea who are like behind you. Uh, and I do the same way for, for my network too. So you find your fans, ask them for feedback, draw them like a little sketch of this is what I'm thinking.

What do you think about this? And, and you'll be surprised at how many people will volunteer their time to go talk to come talk to you because they're passionate about the project you're working on. So I would say like, that's the number one thing. Talk to your customers before investing any time or money into an idea. Yeah. I really want to like echo that because you know, I, my coaching programs and agency, we've worked with thousands of businesses and startups, you know, a lot in that zero to million and like half a mil to 10 mil range is kind of most people I work with.

And the amount of them that get on a zoom with me, right, they join my community or program. They're three years into the business. They're still only making a couple of hundred grand a year. They tell me what their product is. And I'm like, how, you know, I'm like, it's just, doesn't sound that great. Like it, and they kind of like, I mean, the problem is they like get an idea one way, they're kind of kind of passionate about it and they like stumble into it. And they never like maybe rain check themselves and go like, is, could this be a $20 million company? Right. Like, and I think I've, as an entrepreneur, I've created lots of companies to a few million, some to 10 million, and I'm constantly jumping to the next big thing.

And you have to evolve because I think the first thing you start on isn't going to be the thing that makes sure your money, but a lot of them just stick to it, right? They just get, why don't they don't actually take a step back and go, is this the right thing I should be doing? That's right. That's right. That's right. And you're limited time on this planet, so you have to make it count.

Yeah. And I mean, you know, the entrepreneurs, they're like the master, right? I always say they're the all-star. So they can easily go start a new product or launch something new if they're great. And sometimes they should self-evaluate and then I think second time around do what you say, right? Like now you've got the soft skills of marketing and business and hiring and those things like actually look like, does this fit the criteria of a good

company and a product, right? Does it have big demographics and whatever blue ocean and unique, right? Is what's the addressable market size? How saturated is the market, right? Like what other companies have done similar? That's right. That's right. That's right. Most people and it's, it's right, that's right, that's right.

Most people, and it's kind of interesting to observe it, most people will not Google their product idea to see if there are competitors in the market. That's the very first thing I do when somebody reaches out to me for advice or venture capital funding, I will Google their product, their ideas, if there are other competitors

and their pitch deck doesn't have a competitor's line. I'm like, well, you haven't thought through this fully. Well, it's funny because I actually, yeah, now you say it because one of the first things I ask when someone hires us or comes on our group programs, I go, what are some of the biggest competitors in your space? What ads are they running? What funnels, what price plane? And half the time they say, I don't know. And I'm like, what do you mean you don't know? That's like, you know, it's like, I always say, I'm like, that's the bread from trail that you can like follow, you know?

And then you just create a new event, you know, halfway once you get down the trail somewhat. So it's- That's right. That's right. And back at, going back to Amazon, like that was drilled into my head. So if I ever presented, or anybody presented an idea

with the competitive aspect of it left out, you would get skewered. Because the question would be, well, we know Google is doing this, we know Microsoft is doing this. Why is this not in this proposal? What are you doing to compete against these competitors? Well, it's common sense. They've already invested at that level. They've already invested billions of dollars or tens or hundreds of millions into that venture, right? So it's like, well, let's see

what they figured out along the way and where they're at and then save those three years and a hundred million in a time. So, so, but I think it's interesting because I mean, some entrepreneurs don't do it because they almost feel like it's copying or they shouldn't or it's unethical, but it's like, that's just business, right? Like, do you agree? That's just like, you know, and then copy someone's idea, but you should be doing market research on the industry. Yeah, exactly.

I think it's not copying it. One is shows that having a competitor is actually a good sign that the market is healthy. There's space for you to compete. That's number one. Number two, it shows that you have done your research. And I think you mentioned that phrase when we were talking, what is the blue ocean here? If it is a competitive market, what are you doing to navigate this path to find a blue ocean in this sort of ocean you're in?

So I think it's just like, as English common sense, I think most entrepreneurs, not most, but many entrepreneurs, they feel like their idea is so cool and so awesome that there's nobody else doing it. But chances are somebody is doing it somewhere. Yeah. And I think also like, uh, you know, to echo the, the competitor thing, like, I learned long ago and I heard it from some billionaire. I think it's like, you, people think you want to be first, but often you don't because it takes millions to educate an industry if you're first, where you're second, the first person paid to educate them on the idea.

Right. Now, obviously it's sometimes good to be first if you're trying to be like a unicorn billion dollar brand like Uber or whatever, but for most there's normal entrepreneurs that are trying to make a few mill to start. Right. Like it's probably good to know an industry that exists that you can do well in to make your first few million. And then maybe after that, you can go on and create the unicorn of some sort. That's right. That's right. That's right. Yeah. So, you know, last few questions, we were almost up to time. I do want to shift back to the tech side. I know you obviously you've worked in massive tech teams, but a lot of our entrepreneurs are hiring their first tech person on Upwork or whatever, right?

Like what are some of the just sort of key attributes and skills you want from your first tech hire? Well, A, they don't start with a no. So I think that's the first thing you want to look for. And B, you don't need to hire a super senior experienced person as your first tech hire. I think if you're hiring your first engineer, you want to look for kind of cultural match. Does this person like match your speed?

And that's what you're looking for. Um, and do they believe in AI like speeding them up? That's number two, you want to look for. And number three, do they understand the realities of the world we live in? You know, engineering, software development is not as sacred as it was 10, 15 years ago. So do they understand the dynamic and they're more geared towards, you know, I want to get this product out so that we can get customers to use it and make some money versus I want to do something for puristic integrity or something like that.

Right. So, and there are many engineers and things like that. So I was like those three of what I would recommend, like people look for. Yeah. And I think it's, it's interesting also because when you first hire the tech person, you probably don't want this super high level person because what you want someone that's like decently skilled. So they know how to kind of tackle problems. Someone that's a self starter.

Cause even the skilled people, there's hundreds of softwares right now. So like even that guy, he's like, I give him a new thing. He's like, yeah, I don't know that software, but within an hour of re YouTube in it, he's figured it out. Right. So that's more important. Someone that has that fast adaptability will YouTube it, figure it out and how, and you want that like, I found my best tech people are more like me where they can holistically

see a big picture on how to zap stuff together and connect it. And that's tech people have been the smartest like tech geniuses, but they only look in one lane because they're the, let's say can't be done. And I'm like, well, what if you zap, you know, I don't know tech that well, but I've been doing it for years. I'm like, but what if you zap it here and do it there? And then they go, oh, well, you could do it that way. And I'm like, we'll go do it there and then they go oh well you could do it that way and I'm like we'll go do it then you know yeah that's exactly right like what you need is if first tech high is a plumber right who can just like jing them things together duct tape stuff together and get the water to go from a to b yeah and then as you get you know to tens of millions you bring in the real

you know super clean and you know you rebuild it it all and those things. But yeah, I think that's awesome advice. So last couple of questions, just, you know, more as a successful person that you are, I ask everyone on the podcast, what's one of your biggest successes that you're proud of? Where you're like, wow, I did good. I feel I made it a bit at this point, you know, was it a hire or a breakthrough of a project? Um, that's a good one. I think, I think, uh, the release of my first book, I would consider that as, um, as my kind of big win is sort of indicated that I've sort of made it again.

Like I don't, you know, made it is very subjective, but in my mind, I feel like I'm, you know, made it with my first book. So you're not working like Donald sort of, you know, at least. But, you know, we being as entrepreneurial people, we've never made it in our own head because we just list the IUP. Like you, I mean, you have to roll a flex and say, well, I did better than the average kid in my class, you know That's right. That's right. That's right. Yeah. Yeah, I mean, I think another thing will be interesting for your viewers is I was never academically Talented I was always like the average student in class and I think back to my class I was like, I think I beat like 90% of them

So, you know, I think good about you can tell you, you can tell you have more the soft skills, the personal skills, the right mindset, probably let you excel through developers that were maybe more code smart, right? That's right. That's right. Yeah. Which I love, which I think is how it should be. Uh, so last question, um, biggest failure or challenge you had to have with them?

Um, I was broke once. I think right after my son was born, we were living on, we were both my wife and I were making tax salaries, but we're spending way too much living above our means, we're living paycheck to paycheck and one month we just were flat out broke. And I think that day we decided that we're never going to be like this again. So I think it was a good lesson learned and advised the younger people that I give is don't live above your means, save every dollar. I think you can spend it once, once you get to a comfortable level financially.

So yeah, that will be the biggest failure. Do you still look back to, do you still look back to that moment now? You have probably some good amount of wealth at this point. Do you ever look back and go, wow, that's cool? Oh yeah, 100%. That car ride back home, I would never forget it. I keep reminding myself that, yeah, you were broke once. So never forget that.

And ground yourself, be humble and keep learning. Love it. Well, that's a great place to wrap. Awesome episode. You know, tech is often seen as boring. But this is one of my favorite episodes I've shot recently. So I really have bigger conversations and some really great tips for the tech side and also lessons from these big brands. So where do people grab the book or find you on LinkedIn? Yeah. The, the name of the book is how to deliver bad news and get away with it. Uh, you can find it anywhere where books are sold, Amazon, Barnes and Nobles, et cetera.

Uh, and you can find me on LinkedIn or on my personal site, my hashgroswami.com. Good. And I'm sure you got very good at that working with these big brands and big companies and going into the books. Yeah. Good. Good. Well, it's been a pleasure.

Thank you so much for your time. Guys go check out the books. Every book I think is awesome. And I always say books, you know, 10, 20 years, 30 years of knowledge condensed into, you know, an hour or few hours of reading and you can't beat it. So check out the book buddy thanks so much for jumping on a great episode and guys until next time keep living the red life..