In our third edition, we dive into our recent interview with Ajay Kulkarni, CEO and co-founder of Timescale. Launched in 2017, the company has grown at a breakneck pace, raising $180 million in funding, achieving unicorn status, acquiring over 1,000 customers and building a passionate community of more than 50,000+ developers. Ajay’s interview was raw, honest, and bullshit-free. He spoke candidly about the mindset and strategy involved in building a company of this scale and truly held nothing back, offering a unique behind-the-scenes look at Timescale’s journey.

Here are the top actionable takeaways that founders can learn from Ajay’s experience building Timescale into a unicorn in less than 5 years.

#1: Convert setbacks and failures into rocket fuel.

“Like you think you’re really smart, you have these big visions and aspirations. And then I’m having an okay soft landing [Ajay’s first tech company resulted in an acqui-hire]. And I remember looking at all these people who would raise bigger rounds, build bigger businesses, employ more people and I remember thinking that I’m like, wow, I thought I was smart, but are all these entrepreneurs that much better than me? They had better exits. And I kind of felt like I had so much more to prove. And I almost felt like, I don’t know, like a big chip on my shoulder just to prove to myself that they weren’t better than me. I think that’s probably what fueled me with Timescale, is just like, to be like, hey, that exit, I could do so much better than that. I’m smarter and better than that.”

Actionable Takeaway: Leverage that “chip on your shoulder” and use setbacks and disappointing outcomes as fuel and motivation for your next venture.

#2: Avoid being motivated by negative emotions.

“I’m not really motivated by fear and I try not to be motivated by negative emotions. I’m more motivated by positive emotions, like this desire to build something, to really prove it to myself. There are different motivational structures. There’s, positive ones and negative ones, and I think, like revenge or creating grievances, it’s kind of like the dark side of the force. It’ll fuel you, but it’s going to wear you down, man. It’s going to wear you down. It’s going to make you really angry, bitter person. And I feel like I try to prescribe more to the light side of the Force, which is to be inspired, to be motivated to build something for the greater good, to build something new in this world.

Like life is short. So make the most of your time to add to the world and make the world a better place because you were here. That motivates me and I feel like that’s a lot healthier and I don’t know. Yeah, those things are probably decoupled. I think to build something big, to be an entrepreneur, you probably need some type of irrational thing driving you. But that thing could be the dark side of the force or the light side and it’s up to you.”

Actionable takeaway: Harness the positive emotions of ambition and creation as the motivational force for your entrepreneurial journey, rather than resorting to fear or negative emotions. Aim to choose a drive that not only fuels your success, but also contributes to the greater good, fostering personal growth and a healthier mindset

#3: Use intellectual honesty to determine if you are heading down the right path.

“One of our strengths as a company, and especially with myself and Mike as founders, is that we try to be very thoughtful and have opinions, but we also believe in intellectual honesty and clarity, and we try not to be stubborn. And a year into the IoT platform [Timescale eventually pivoted to a database product], we’re like, why isn’t this thing more successful? It’s semi-successful which is almost the worst. I think bad ideas are easy to kill, great ideas are easy to recognize. But when you have a good idea, you’re like, why isn’t it great? Should we kill it or not, right? And so I think that’s what kind of gave us pause. We’re like, hey, either we’re building the wrong thing or we’re building the right thing but at the wrong time or the right thing at the right time, but we’re the wrong people to build it.

And we’re like, we’re not sure what it is, but something feels off about the traction being good, but not great. And I think another one of our strengths is just really listening, super hyper listening when we talk to customers or developers or to the market. And it was really remarkable. When we talk about the database, people would literally kind of lean forward and be like, oh, hey, wait, what was that thing? Can you tell me more about that? Because we’re using, like, Cassandra or Mongo or whatever, and it’s not working. And that sounds useful. And after a while, were like, no one’s getting that excited about our IoT platform. Maybe the database, maybe that’s the thing to do. So that’s how we did it.

Timescale is built upon intellectual honesty and not being afraid to admit that maybe you made some wrong assumptions or wrong decisions”

Actionable takeaway: Embrace intellectual honesty in your pursuit of greatness. When it comes to your product, don’t settle for merely ‘good’ – expect ‘great’. If your good idea isn’t making the expected impact, question your assumptions, listen to your customers, and take massive actions. Recognizing the difference between good and great can illuminate a new direction for your business, one that aligns with your market’s true needs.

#4: Play the long game: harness the power of community.

“Early days, first couple of years of the company, we did not really think much about monetization and really focused on building the community. Everything we built was open source, everything was free. The way we built it is we just tried to really help. First, we provide a lot of value. We had an active, we still do, but early on we launched our Slack channel where we provide free support. And myself, my co founder, would be really active in it, our engineers are active in it. And so it’s kind of like, hey, let’s build something for free, build a community and provide a ton of value and then we’ll figure out how to monetize it. And we had some hypotheses. So that’s how in the beginning we kind of built the community.

Actionable takeaway: In the early stages of your company, prioritize community building and value creation over immediate monetization. Provide your product or service for free, engage actively with your audience, and foster a strong community. This community-led approach can help establish a loyal user base and a solid foundation for your company.

#5: Prioritize shortening decision making cycles.

“Our biggest risk is not strategy or market or funding or team. I think it’s just execution. And not that we’re dumb or lazy. No, we’re hardworking and we’re smart, but even then, are some things taking a month to be decided? That when they could have been decided in 1 hour meeting? That’s what I worry about. One of our operating principles at Timescale is shortened the cycle. And we kind of have this assumption that says, hey, I assume you’re working as hard as you can because you’re a Timescale we hire the best and the brightest, and everyone is just hustling. So I’m assuming that I don’t want you to work every hour of every day. You’re just going to burn out, and that’s not sustainable, but I’m assuming you’re going to hard work, hard as you can.

But if we want to move faster, how do we shorten the cycle? Are there some things that take a month that should take a week and they take a week? Take like, a day? There’s some things that we’re debating that are totally reversible. Like, if it’s a reversible thing, then you don’t have to debate it, just try it. And if it doesn’t work, just revert it. I’ve been guilty of that too. I remember at one point I was kind of debating something with my co founder. He was like, hey, Ajay, what’s the downside if we get this wrong and revert in a month? I’m like, yeah, not much downside. So that’s what I worry about. It’s like, hey, are we just working on the right things, and are we shortening the cycle as much as we can?”

Actionable takeaway: To enhance execution and efficiency, intentionally shorten your decision-making cycle. Reflect on whether certain decisions or tasks are taking longer than necessary. Could a process that takes a month be done in a week? Or a week’s task completed in a day? Prioritize actions with reversible outcomes and don’t hesitate to try new strategies. If they don’t yield desired results, make adjustments. This strategy allows you to maintain productivity and pace, ensuring you’re focusing on the right areas at the right time.

#6: Understand your GTM motion to determine if you need analysts.

“Analysts can be helpful. It depends what type of business you have. If you’re a top down go to market, I think you need analysts early on. We’re more bottoms up, we’re more PLG. We just added our first sales leader at the end of last year, so we got this far without a real sales team, right? So really PLG, really bottoms up. And so for that, we’re really targeting an individual developer who cares more about what their peers say on Hacker News and Twitter and Reddit than what, I don’t know, Gartner says now as we move up the we are starting to engage with analysts, but it hasn’t been a big part of strategy so far, but it’ll become bigger as we go on. Now, if were a top down company, I’d have a totally different answer.”

Actionable takeaway: The necessity of analysts in your business depends on your GTM strategy. If you are adopting a top-down approach, analysts could be essential from early stages. However, if you have a PLG. model with a bottom-up strategy, your initial focus might be more on peer opinion and community sentiment. As your business evolves and starts targeting larger organizations, integrating analysts into your strategy may become more relevant. Understanding your GTM motion is critical to determine when and how to effectively engage with analysts.

#7: Articulate a Strong POV and vision for the future

“We believe every company is becoming a software company, and databases are the foundation for great software. But in particular, at Timescale, we believe that postgres provides a great starting point to build a great database. And so we believe that by building a really great database platform, we can build a fundamental building block for every company in the world, whether five, six years from now. Again, I think the database needs to be reimagined. I think the database in the cloud will look very different. You’ll see some stuff for us in the next few months, the next couple of years that reimagines the database experience. In five, six years, I think you’ll see the next evolution of the database paradigm. I think you’ll see us super focused on the customer building, the next wave of computing, the future of computing.”

Actionable takeaway: Harness a strong point of view (POV) as a rally point for both employees and customers, aligning them with a shared vision of the future. Invest time in crafting a clear, concise, and compelling future vision can inspire innovation, drive adaptability, and foster a customer-centric focus, preparing your company for the industry’s ongoing evolution.