Karthik Vijayakumar · Podcaster · Writer · Speaker
I ask the questions that turn a founder's story into trust.
Host of The Underdog Deal and founder of Orii Labs. I help B2B founders win deals against bigger competitors by becoming known before the sale.
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About
I've watched the better product lose.
For 15 years I worked in enterprise software selling into the US, as a programmer, a solutions architect and presales lead at IBM, and a product manager at CollabNet. Again and again, buyers chose the name they knew over the product they liked.
In 2016 I launched my first podcast and went on to interview 275+ founders and CEOs. That's where I learned what a good question can do. In an hour, founders find the story they didn't know they had, and sometimes unlock a decision about their business.
Today I bring it together. At Orii Labs, I turn founders' stories into LinkedIn content buyers trust. On The Underdog Deal, I ask how they won the deals they weren't supposed to win. On stage, I help rooms full of founders ask better questions of their own.
What guests say
What it's like across the table
From founders, CEOs and investors who have been on plenty of podcasts.
“Thanks a ton for helping me narrate my story! Talking to you also helped me define the structure and focus for a TEDx talk.”
Karthik is a brilliant interviewer with great questions. I enjoyed every minute of the conversation, and it was just brilliant. It felt more like a conversation with an old friend. I would absolutely recommend the show to everyone and have started to do so!
Investor
Karthik is a great interviewer who really took the time to go deep and find out the WHY, and even more for his listeners… He really wanted to find the gold for his community. Love the interview series for the way he extracts insights and lessons from so many interesting people!
President and Chief Bargain Officer, Bargains Group
Karthik's questions were thoughtful, well-researched, and drove to a singular, important point. He's clearly capable of going deep with big thinkers. His conversations flow naturally, and he remains light even when topics are heavy. I particularly enjoyed Karthik's ability to connect key moments in one's life story, making them relatable to someone new to the conversation.
Co-founder, ADMCi
Speaking
Talks for founders and the people who back them
For founder communities, accelerators, startup conferences and sales teams. Built on ten years of conversations with founders and 15 years on the vendor side of enterprise deals.
Why the Worse Product Wins (and How Startups Can Stop Losing to the Safe Choice)
Buyers don't pick the best product. They pick the vendor they trust not to fail them. What really decides enterprise deals, drawn from real underdog wins, and what founders can do about it before the first call.
For founders · accelerator cohorts · GTM teams
The Questions That Unlock a Founder's Story
Every founder has stories that make buyers, investors and hires trust them. Most can't see their own. The questions that bring those stories to the surface, from 275+ interviews, and how to use them.
For founders · leadership teams · founder communities
Known Before the Call
Cold outreach is getting harder. How founders become a name their buyers recognize, using stories, LinkedIn and conversations, so the first sales call starts warm.
For founders · sales and marketing teams
Formats
- Keynote
- Fireside chat host
- Panel moderator
- Workshop
- Virtual session
Ten years of interviewing means I'm as comfortable asking the questions on stage as answering them, so hosting a fireside chat or moderating a panel is a natural fit.
What your audience leaves with
- A clear picture of why buyers choose the safe option, and what makes them take a chance on a startup.
- Questions they can use the next day, in a sales call, an investor pitch or a post.
- At least one story from their own company they'll want to start telling.
The podcast · First episodes Nov 5, 2026
The Underdog Deal
How B2B startups win against the incumbents
Every B2B founder knows the feeling: the demo went well, the buyer loved it, and then they picked the bigger company anyway. Each episode, a founder takes us inside one deal they won against a much bigger competitor: who was in the room, what the buyer feared, and what finally tipped it.
Listen on Apple Podcasts, Spotify and YouTube from November 5. Be a guest
Work with me
Orii Labs
Buyers choose the vendor they already know and trust. Orii Labs helps B2B founders and CEOs, pre-seed to Series A, become that vendor on LinkedIn.
Content is half of it. I find your stories and write in your voice, so the right buyers start to know and trust you. The other half is conversations: engaging the people who reach out and warming them up until you're ready to step in.
FAQ
Good questions
Who is Karthik Vijayakumar?
Karthik Vijayakumar is the founder of Orii Labs and host of The Underdog Deal podcast. After 15 years in enterprise software and 275+ founder interviews as a podcast host, he now helps B2B founders win deals against bigger competitors by becoming known and trusted before the sale.
Does Karthik speak at events?
Yes. Karthik gives keynotes and workshops, hosts fireside chats and moderates panels for founder communities, accelerators, startup conferences and sales teams. Send an inquiry through the booking form on this page.
What is The Underdog Deal?
The Underdog Deal is a weekly podcast about how B2B startups win deals against bigger, established competitors. Each episode reconstructs one real deal with the founder who closed it: who was involved, what the buyer feared, and what tipped the decision. It's available at underdogdeal.com.
What does Orii Labs do?
Orii Labs helps B2B founders and CEOs, pre-seed to Series A, turn their stories into LinkedIn content that builds trust with buyers. Work includes a profile rewrite, a voice profile, a content strategy, ready-to-post content, and DM engagement that turns interest into conversations. Learn more at oriilabs.com.
Who does Karthik work with?
Founders and CEOs of B2B startups, from pre-seed to Series A, whose buyers are in the US. He has also written for founders at Series B.
How can I be a guest on The Underdog Deal?
If you've won a deal against a much bigger competitor, apply at underdogdeal.com or message Karthik on LinkedIn.
Where can I find Karthik Vijayakumar online?
On LinkedIn at linkedin.com/in/kartvee (his handle is kartvee on most social platforms), at kartvee.com, and on The Underdog Deal at underdogdeal.com.