Inside the Mind of Tech Leader Mahesh Guruswamy

47.039 - 59.479 Rudy Moore

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?

60.29 - 83.529 Mahesh Guruswamy

Yeah, sure, sure. So my name is Mahesh 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.

85.191 - 101.253 Rudy Moore

And 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?

102.836 - 109.038 Mahesh Guruswamy

I think the single biggest lesson that I've learned is don't start with the no.

110.358 - 123.802 Rudy Moore

Don't start with no, it is not possible to do X, Y, and Z. I've fired tech people over that one exact thing in my life because it kills creative energy as an entrepreneur and a founder.

124.142 - 147.331 Mahesh Guruswamy

right that that's exactly right this is exactly right and you know the the most successful companies that i work for amazon kajabi kickstarter have all been you know slightly crazy right he had to be a little bit crazy to believe that he can do the things that these companies pulled off really have to be crazy i sound delusional because i believe in my ideas so much it's a borderline insane

148.41 - 167.186 Mahesh Guruswamy

That's what 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? And that's the attitude you should have.

167.785 - 186.248 Rudy Moore

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 every time, you know, 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.

186.308 - 195.59 Rudy Moore

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 if...

196.73 - 213.162 Mahesh Guruswamy

It's so funny. Yeah, it's so funny because I've used the exact same analogy with my teams too. You said, if somebody tells me, this takes me six months or nine months, Elon has spent rockets to space in that time. So why can't we get this thing done sooner? So I'm with you.

213.982 - 233.976 Rudy Moore

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 life 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.

234.036 - 238.559 Rudy Moore

And how do we look at the mystic setting versus a pessimistic setting?

239.119 - 245.447 Mahesh Guruswamy

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.

246.365 - 270.435 Rudy Moore

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, you know, you need to have that crossover and great teamwork. 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 out of 500 hours to build. Right.

270.795 - 273.997 Rudy Moore

So how should entrepreneurs work with their tech team?

274.824 - 298.575 Mahesh Guruswamy

Well, I think my usual MO is doing a little bit of research upfront with customers because, you know, I have a thousand ideas and like 90% of them could be garbage. Right. That's the thing. That's the thing. So I don't like 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.

298.696 - 324.234 Mahesh Guruswamy

I always have a small group of motivated customers who I can go to and ask feedback from. And if directionally the feedback is positive, then you build something which is like an MVP. It's like duct tape and a small thing that you 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 the Ferrari and then trying to sell it.

324.294 - 329.896 Mahesh Guruswamy

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.

330.377 - 342.482 Rudy Moore

Yeah. Or what we do and what Elon does is you build the, like a fake model of a Ferrari or a Mazda and then build it with the money that you made from pre-selling it. Right.

342.942 - 344.243 Unknown

That's right. Yeah.

344.89 - 369.213 Rudy Moore

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 a main company. Like I've always sold products that I think are faster, you know, courses, coaching, education, communities, supplements, e-commerce, right? And I've done pretty well. I've scaled e-commerce brands to a million dollars a day.

369.273 - 391.02 Rudy Moore

So big numbers, but 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.

391.04 - 394.761 Rudy Moore

So how do you balance that for software companies? Yeah.

395.441 - 415.993 Mahesh Guruswamy

I think it comes down to prioritization is what I would say. There's always going to be a thousand different things to do. So as leaders, you have to realize what is most important and figure out what to put it in the top of the list and what to put at the bottom of the list. I think the other dynamic that's playing out, and I know my network will hate me for saying that, is leadership.

416.753 - 436.065 Mahesh Guruswamy

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. And if engineers and product managers and everybody else in tech feels like they have special skills, I think a reckoning is coming.

436.085 - 444.59 Rudy Moore

I think it's like everything now. We were talking with my team, Mark's team today, we went from nine copywriters to two.