LIU024: Dennis Thankachan: Lightyear and Beyond
The Everything Feed - All Packet Pushers Pods
October 8, 2026
Lightyear CEO and co-founder Dennis Thankachan shares his transition from investment banking to entrepreneurship and the lessons learned from his early startup failure.
Speakers Kevin, Alexis, Dennis Thankachan
TopicsTechnology
Kevin (0:05)
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Welcome to Life in Uptime, the show where we talk with the people behind the networks that keep our world connected. I'm Kevin, joined by Alexis, and every week we sit down with engineers, leaders, and builders in tech to uncover the stories behind their careers. How they started, what they've learned, and where they're headed next. Our goal is simple, to help you see how far can take you no matter where you start from.
Alexis (1:08)
All right, guys, today we have a very special guest for you. We're here with Dennis. He is the CEO and co-founder of Lightyear. Now, before Lightyear, he worked in investment banking and invested in software and telecom companies.
And we are so excited to have him on the show today to talk about everything he's done. Dennis, welcome to Life in Uptime. How are you doing?
Dennis Thankachan (1:33)
Doing great. Thank you for having me on. Excited to chat here.
Alexis (1:37)
Absolutely. Now, I'm curious, telecom to me, I guess my first experience in networking was through Cisco. And I never, it sounds bad to say, but I feel like I only really worked on one end of the Internet. Like after I gave customers their switches and their routers, I never really asked a lot of questions about how they were getting connected to the Internet or to anything, until I started working with Megaport. And then I was like, oh wait, companies have to buy Internet too. Like it's not, it's not just, it's not just consumers. And then I got introduced to like the whole world of telecom.
How did you get started in telecom?
Dennis Thankachan (2:24)
I will say that I also deeply underappreciated telecom until I ended up investing in the space. I still remember when I was a computer science undergrad, tracking the bits from pop to pop for my networking course and finding it amazing that I'm seeing something instantly online, that there are many different points of presence being traversed by information. And it's kind of amazing that all of that actually works.
But the thing that most amazed me about connectivity and why I got started was, in 2019, I set out after spending a few years investing in telecom and feeling like I really knew the price, investigating the massive trillion-dollar area that is business telecom spend, and being kind of appalled by how things are done.
By 2019, 2020, it feels like every segment of our lives has been transformed by the internet, cloud and software. You buy flights differently, you buy clothing differently, you buy services differently, you get a car differently. However, the way that enterprises like giant companies spending millions and millions of dollars on the most important stuff, get their connectivity really is very similar to the way that it was in 1997 It's just the products they're buying are different. Maybe they're buying 10 gigs rather than T1s. And that's just amazing to me. And the question that I asked was, oh, could this also be transformed by software? And would that be better for the enterprise? With investigation, I became really, really convinced that the answer was yes, and that if me plus a team of people could build something, it'd be both a really fun and exciting journey and also potentially a great way to build a career.
Alexis (4:21)
Do you think that, I mean, studying computer science and coming from a more technical background before pivoting into business, is that why you were looking at this from an automation standpoint?
Dennis Thankachan (4:35)
Yeah, so I studied computer science with the intention of creating a business.
Alexis (4:44)
Okay.
Kevin (4:45)
Interesting.
Dennis Thankachan (4:47)
When I was in college, it was around the time of the craze of the social network film, Y Combinator becoming a bigger thing, and the notion of creating a startup being very, very exciting. And prior to college, I was making websites to make money, basically trying to find any way I could create something that could result in making money and just became very, very passionate about that. And then this whole startup craze invigorated young CS graduates on that particular path. So I was really hell bent on creating some sort of a technology product or thing at some point in my career. And really it was a matter of searching for that thing.
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