Kickstarter’s Former Tech Chief on Hiring, Scaling & Startup Fails
episodePreviously titled “Inside the Mind of Tech Leader Mahesh Guruswamy” — renamed by the publisher on Aug 2, 2026
Transcript
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Transcript generated automatically by AI and may contain errors.
What are the harsh realities of entrepreneurship?
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 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.
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?
Why do entrepreneurs often skip market research?
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've fired tech people over that one exact thing in my life because it kills creative energy as an entrepreneur and a founder.
How can I identify a winning business idea?
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 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.
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.
Why shouldn’t you always be first in the market?
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...
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.
What is the power of competitor analysis?
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. And how do we look at the 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.
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Chapters
10 chapters
1
What are the harsh realities of entrepreneurship?
0:47–1:42
2
Why do entrepreneurs often skip market research?
1:42–2:04
3
How can I identify a winning business idea?
2:04–3:06
4
Why shouldn’t you always be first in the market?
3:06–3:33
5
What is the power of competitor analysis?
3:33–4:06
6
What should I look for when hiring my first tech person?
4:06–4:58
7
What is the 'Plumber' approach to early-stage tech?
4:58–5:30
8
What is the biggest lesson from Amazon’s work culture?
5:30–6:09
9
How do I overcome financial hardships in business?
6:09–6:35
10
How do I deliver bad news and still win in business?
6:35–26:34
Speakers
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