Most Dumb Ideas Are Definitely Dumb
Ajay Kulkarni of Tiger Data on How to Know When Your Gut Is Right
Written by: Paige Bennett
Original photography by: Irina Logra
Summary
- From "Dumb Idea" to success: Tiger Data (formerly Timescale) CEO Ajay Kulkarni built a time-series database for PostgreSQL despite skepticism, now serving Tesla, NASA, and JP Morgan after raising $180 million.
- The Pain Test framework: Successful startups identify real pain points—Ajay's team experienced frustration managing IoT data across multiple databases, validating their solution when others shared the same struggle.
- Learning from failure: Ajay's previous startup Sensobi dominated BlackBerry but failed to pivot to iPhone, missing out on WhatsApp-level success and teaching him that creativity and market awareness matter more than timing.
- Intellectual honesty as strategy: Tiger Data maintains a low-ego culture focused on seeing reality clearly, exemplified by their quick rebrand from Timescale when the name no longer fit their expanded offerings.
- Sorting priorities: Ajay prioritizes family and self-care as "glass balls" that can't be replaced, while treating the business as a "rubber ball" that can bounce back—a balance that ultimately improves both.
Introduction
Every day, the world generates an estimated 402.74 million terabytes of data, with around 90% of the world’s data generated within just the last two years. In response, companies like Tiger Data and platforms like PostgreSQL are on the prowl to find ways to expand data storage, management, and security for the data needs of the future.
When Tiger Data first launched, then known as Timescale, the idea to bring time-series to PostgreSQL when companies were moving toward NoSQL databases was controversial. One of the top responses to the company’s launch was “While I appreciate PostgreSQL every day, am I the only one who thinks this is a rather bad idea?”
But Ajay Kulkarni, CEO and co-founder of Tiger Data, knew there were pain points with juggling data in different systems. “I think most great ideas, they sound crazy in the beginning if you haven't felt it,” he says.
Understanding this pain point for developers helped him move forward with the idea for what is now Tiger Data, even if there were concerns about the idea being ‘crazy’ or ‘dumb’.
“One thing I've learned is like, if something feels dumb, you have to ask yourself, ‘is it really dumb, or is it actually brilliant?’”
Ajay clearly found proof in his brilliant idea. Today, Tiger Data powers companies and organizations such as Tesla, NASA, and JP Morgan Chase. The startup has raised $180 million since its launch.
This journey to success came with many challenges along the way, but these challenges give way to lessons on how to differentiate another ‘dumb idea’ from a truly brilliant one.
The Pain Test
The Ice Cream for Cats Framework
Testing extreme and seemingly ridiculous ideas is all part of the process to finding whether you truly understand your target audience. First: do you understand their pain? Do you really understand it?
Ajay likens it to pitching an ice cream for cats. The idea probably sounds absurd to someone without pets, but for pet owners, it could be a chance to pamper their cats with a special treat. Niche products like cat strollers or pet hotels can similarly solve unique concerns for pet owners. At this stage of testing, you have to understand the pain points for the target audience, and you have to trust your gut instincts on whether the idea has any footing.
For Tiger Data’s founders, they had been working in IoT (Internet of Things), managing data for 100,000+ devices with data split across multiple databases. The sensor data is one place, while business data was in another. This stalled development, where even one task that should take about 10 seconds could require a two-week sprint.
“We’re like, ‘This is kind of dumb’ and ‘I wonder if we could do better,” Ajay says. “So, we built the first version of this for ourselves. As we started talking to people, we realized that other people were like, ‘Actually, wait, can I can I use this thing, too?’ So, we knew that we knew this pain existed.”
Personally feeling this pain drove the founders’ conviction that something like a time-series database with PostgreSQL was necessary, despite the naysayers.
The Contrarian Reality Check
Originally, the idea for Tiger Data, then Timescale, was considered ridiculous for such an “old-fashioned” database. People doubted the company could scale or that it would work quickly enough to meet developers’ needs.
But as Ajay points out, there are many household-name companies out there today that disrupted existing ideas. It may have at one time seemed crazy to rent someone’s couch or guest house, but Airbnb is wildly successful with a market cap of over $70 billion. Another example is Amazon, which started out by selling books online, or Netflix, which people thought could never replace companies like Blockbuster.
Then, there’s Uber.
“I dismissed Uber, because I thought Uber was just like a luxury car service,” Ajay says. “Uber was probably the first company that I dismissed, and I totally missed it, you know? I was like, ‘A black car service? Yeah, that's cool, that's fine.’ But no, it’s reinventing transportation.”
Transformative ideas may sound off-the-wall. Why try to reinvent the wheel? But those who know the pain in a system know they aren’t just recreating something that already exists. They’re transforming that industry with a solution to an existing problem.
Following your gut can help decipher between a good idea and a weak one, but it’s not the only metric to consider.
One thing I've learned is like, if something feels dumb, you have to ask yourself, ‘is it really dumb, or is it actually brilliant?”
— Ajay Kulkarni, Co-Founder and CEO of Tiger Data
The WhatsApp Lesson: When Following Your Gut Isn't Enough
The BlackBerry Success Story
Ajay had to learn a hard lesson early on, though — sometimes, failure is inevitable. Even a gut-check can’t always protect you. But the failure doesn’t define you or your chance at success; it’s what you do with that failure.
It all started with a previous startup Ajay had founded, Sensobi. Back in 2008 and 2009, Sensobi was massive. It was the leading address book for BlackBerry devices. BlackBerry was at the time a huge success, and Sensobi was experiencing viral growth and a diverse userbase spanning from wine distributors to parents of children who had special needs to a producer at Roc-A-Fella Records, all of whom were relying on this technology daily.
Then came the turning point: should Ajay and the team stick with this momentum, or was it time to pivot with rising interest in iPhone?
Even Ajay’s dad said to him, “Why are you building a BlackBerry app? The future is iPhone.”
However, the gut instinct was to ride the momentum. Hindsight is 20/20, though. BlackBerry’s success quickly fizzled out, and we all know how Apple’s story has turned out.
“That's kind of like being the tallest person on a sinking ship,” Ajay says of Sensobi’s success.
The Email Never Sent
While Sensobi was gaining popularity with BlackBerry users, another company was also building a similar address book. Someone from that team reached out with feedback and wanted to stay in touch.
“Me being young and dumb and whatever, I actually never responded,” Ajay recounts.
Sensobi later went through a series of acquisitions: it was acquired by GroupMe, GroupMe was acquired by Skype, and then Skype was acquired by Microsoft.
Meanwhile, the company that had reached out to Ajay to connect ended up in one of the biggest M&A deals of all time. That other company was acquired by WhatsApp, which was later acquired by Facebook (now Meta) in 2014 in a whopping $19 billion deal.
“Oftentimes, you look at a company and say, ‘Oh, hey, they got lucky. They’re at the right time, right place,” Ajay says. “But I look at this story, and I was like, ‘We were at the same place at the same time. Were they smarter and better than us? Okay. Maybe, but we’re not dumb. Maybe they’re a little bit better, but it's not like ‘Oh, they’re amazing. We’re terrible.’”
The difference lies in that when WhatsApp noticed Apple’s success in launching push notifications, they pivoted into messaging after starting as just an address book.
“The thing I learned from that was like, holy cow. The limiting factor for us at that point, it wasn’t timing, and it wasn't luck. It was our own creativity and imagination,” Ajay shares.
The Real Lesson
It would be easy to feel defeated as a founder after an experience like that. You seemingly did everything right. You found a problem and solved it. You drew in more and more customers. You continued on with an opportunity that your gut instinct said was the right call for the future.
But you missed out on much higher potential. So, what do you do next?
For Ajay, it wasn’t time to quit. In fact, he was just getting started.
“The main thing I took away from that was like, dude, we were this close. Let’s fucking go. Let’s do it again,” he says.
“I think every company is probably one or two steps away from being on a rocket-ship trajectory, and you just have to listen to the market, be brutally honest with yourself. It’s not easy, but it’s there.”
Ajay used his experience with Sensobi to drive his creativity and passion into new ventures, taking the hard lessons he learned with him. It’s what has allowed Tiger Data to make smart moves, particularly in the time of AI.
“The main limiting factor is no excuses.”
Intellectual Honesty as a Superpower
No Excuses, Clear Eyes
The experience with Sensobi, and the miss of collaborating with WhatsApp, has shaped Tiger Data’s culture today.
“I try really hard to look at situations with clear eyes and a steady mind,” Ajay explains. “I think if you don’t see reality for what it is, then you can’t really respond to it. So, for example, if you’re making mistakes but your ego is preventing you from seeing that, you're going to keep making those mistakes, right? It usually works that way.”
But Ajay says, “If you want to win, if you want to be successful, you have to be honest with yourself so you can look at reality for what it is.”
With that lesson, he sought out leaders who felt the same way. The result is a low-ego culture set on simply finding the right answers, not arguing that you’re right.
The Rebrand Decision
Throwing ego aside was essential in redefining the business once known as Timescale. As the company grew and adapted its offerings beyond just time-series, they knew it was time to face reality and consider an update.
Ajay likened the situation as having a restaurant called Best Pizza. It’s a great name for a place that sells just pizza, but if you add in top-tier burgers and milkshakes, too, people still aren’t going to go to your shop for that.
“Timescale was like that. It was a great name when we were a time-series database, but then we started to do a lot more than just time series,” he says. “We realized that our name was holding us back. So, we changed to a name that gave us the flexibility to really be whatever we wanted it to be.”
This is where trusting your instincts comes back into play, though. Timescale’s leaders needed to decide: were they fully pivoting, or just refreshing the identity to match who they were in the moment?
“Tiger made a lot of sense because Tiger was our mascot. In fact, we didn't even change our logo. Our logo stayed the same, even though we changed our name,” Ajay explains.
The shift paid off — it took three weeks to execute with a 200-person team of employees, but they trusted that they could (and should!) move quickly.
If you want to win, if you want to be successful, you have to be honest with yourself so you can look at reality for what it is.”
— Ajay Kulkarni, Co-Founder and CEO of Tiger Data
Some Things Break When They Slip Through the Cracks
The Entrepreneur’s Juggling Act
Having the clarity to know when to pivot or persist is more than just market timing and gut instinct. The juggling act of work/life balance also comes into play. Ajay recalls hearing a famous dot-com era entrepreneur speak while he was in business school.
The speaker said, “As an entrepreneur, you’re juggling a lot of balls. And every now and then, you’re gonna drop a ball. Now, some of these balls are rubber, and if you drop them, they’ll bounce right back. Some of these balls are glass, so if you drop it, it’s broken forever. The key is to know which ones are glass and to not drop them.”
This is how Ajay feels about his family: they are the glass ball to never drop.
“My wife, my kids, my parents, they’re all number one,” Ajay says. “The business is great and look, you know, I do spend a lot of time on the business, but my family is number one, and I’ve tried to keep that in mind.”
Keeping Your Priorities Straight
To prioritize family over everything, Ajay recommends having boundaries and rituals to keep business matters out during those special moments with his loved ones.
Ajay’s friend, Frederic Kerrest, co-founder of Okta, gave him sage advice: at dinnertime, everyone’s phones go on a shelf, and the family goes phone-free for a few hours. This time to reconnect and bond with loved ones can help founders feel sharper and more present both with family and back at the office when it’s time to focus solely on the business.
Outside of prioritizing family, Ajay also recommends focusing on other self care. For him, that means tending to his fitness and mental health are top items on his daily to-do list.
“You have to take time some time off to sharpen the saw,” he says. “I love to exercise. There is a book called Essentialism that talks about how you have to protect the key asset, and the key asset is you. But it’s tricky.”
The Business as a Rubber Ball
Building a startup can feel intimidating and urgent, but Ajay reminds us that the business is a rubber ball. If you drop the ball on work while prioritizing your family and health, it’s okay — your startup is the rubber ball, and it can bounce back.
“Am I always successful? Probably not as much as I'd like to be,” Ajay confesses. But that doesn’t change his rituals or priorities. He still focuses on his rituals for those glass balls.
And the result is ironic. Even if you feel like you’re dropping the rubber ball to focus on the glass, you’ll find that protecting the glass can make you even better at juggling the rubber balls.
Conclusion: The Gut Check Framework
Trusting your gut plays a huge role in startup success. But as Ajay can attest, you also have to be honest with yourself about whether to keep persisting, or to pivot.
When it comes to deciding, ask yourself: 1) do you feel the pain personally, 2) can you see reality clearly, even if it contradicts your plans, and 3) are you protecting what can’t be replaced?
At the end of the day, don’t sweat the outcome. Even if it feels like a major mistake, your decision ultimately shapes what comes next. Missing out on an opportunity that eventually became part of WhatsApp didn’t break Ajay; instead, it fueled Tiger Data. Embracing time-scale may have been a decision that was once ridiculed, but it’s now a forward-thinking startup continuing to scale successfully.
And no matter what challenges your startup journey brings, don’t forget to keep your priorities straight, and never drop the glass ball.
Author: Paige Bennett
Paige is a freelance editor and writer with nearly a decade of professional experience covering marketing, sales, and lifestyle content. Her work appears on the main HubSpot blogs, Business Insider, Better Homes & Gardens, Reader's Digest, and more. She earned her Bachelor’s degree in Journalism from Ohio University, specializing in gender studies and sustainability. Fun fact: as of this writing, she has sustained a 1,200+ day meditation streak (we can only imagine what her Duolingo streak must be!)
