Jay Paulynice

Co-Founder at @OatfinHQ | 15+ years as a software engineer | @Cornell alum

[Jay Paulynice @jpaulynice]

I had some time to put together an architecture diagram of what we've been working on at @oatfinhq. Pretty cool stuff I would say...

[Jay Paulynice @jpaulynice]

@duolingo Hello! I have a 863 day streak, how do I get a free one year of Super Duolingo? I would appreciate it. My username is: @ jpaulynice

[Jay Paulynice @jpaulynice]

@nikitabier X is for B2C marketing whereas LinkedIn is for B2B marketing

[Jay Paulynice @jpaulynice]

It’s been almost 6 years since I wrote the first line of code that would eventually become @OatfinHQ. From the outside, it might look like things are going well now. But it didn’t start that way.

In the early days, I dealt with intense imposter syndrome. I constantly questioned whether I was even the right person to build this.

I was a strong developer, but I knew plenty of people smarter than me who could’ve built something like Oatfin.

My dream job was to work at Google. But I failed the onsite interview at least five times. That stuck with me for a long time.

It made me question whether I was even good enough to be there, let alone build a company.

But over time, I started to realize something:
Being the "smartest" person isn’t what determines who actually builds something meaningful.

It’s who stays.
Who keeps showing up when things are unclear.
Who keeps building when there’s no validation.
Who keeps going when quitting would be the easier, more rational choice.

There are a lot of smart people out there. Not all of them stick with one problem for 6 years.

That’s where the edge comes from.

Imposter syndrome never fully leaves.

But it gets a lot quieter when your track record starts speaking louder than your doubts.

[Jay Paulynice @jpaulynice]

Back in 2020, I walked away from a six-figure software engineering job without a clear plan.

Reflecting on almost six years of building @OatfinHQ, I had a strong sense we were onto something. Across many companies I had worked at, cloud infrastructure was consistently a major pain point.

Just a conviction that something was broken.

At first, it didn’t look like much. Long nights, second-guessing, and building without validation. No clear roadmap, just a belief that if infrastructure felt this painful everywhere I’d been, it wasn’t just me.

Over time, patterns started to emerge.

It wasn’t the tools. It was the complexity behind them.
More services. More environments. More edge cases.
Everything worked… until it didn’t.

That’s when Oatfin really started to take shape.

Instead of adding more tooling, we focused on removing friction — making infrastructure something teams could actually reason about, not fight against.

The early years were slow. No momentum, no clear signals. Just persistence.

But eventually, things started to click.

Customers came in. Use cases got clearer. The vision sharpened.

And for the first time, it felt like we weren’t just pushing…

...we were compounding.

[Jay Paulynice @jpaulynice]

Most DevOps teams don’t have a tooling problem. They have a scale problem disguised as a tooling problem.

We ran into this at @OatfinHQ. Early on, spinning up infrastructure was manageable. A few services, a few environments, some scripts holding things together.

Then things started to break.

Not because the tools were bad — but because the system didn’t scale with the complexity.

Here’s what actually happens as you grow:

More services → more dependencies
More environments → more drift
More engineers → more inconsistency

At some point, “just follow this runbook” stops working.

So we stepped back and asked a different question:
What would this look like if it were self-service from day one?

That shift changed everything.

Instead of:
→ Engineers manually stitching infrastructure together

We moved to:
→ Declarative templates + automated provisioning
→ Standardized environments across teams
→ Infrastructure that behaves predictably, every time

We saw fewer production incidents, dramatically lower cognitive load for engineers, and almost zero time wasted debugging “works on my machine / staging but not prod” issues.

The biggest lesson:

Scaling infrastructure isn’t about adding more tools. It’s about removing variability.

[Jay Paulynice @jpaulynice]

Building @oatfinhq has been THE hardest thing I’ve ever done in my life.

But for the first time, it feels like we’re not just pushing…

...we’re compounding.

For the first two years, it was just belief. No revenue. No validation. Just building, questioning, and figuring out if we were even solving the right problem.

What changed wasn’t some big breakthrough moment.
It was clarity.

Getting clear on who we’re building for
Getting clear on the problem we actually solve
And staying stubborn about doing it the right way

The growth we’re seeing now is just the output of that clarity. It’s the sound of the flywheel finally starting to catch. We spent years laying the track, and now the train is actually moving.

There’s still a long way to go.

But this part of the journey feels different. We aren't just fighting for survival anymore; we’re building for the future.

[Jay Paulynice @jpaulynice]

It’s not often you get the opportunity to decline a VC or accelerator. But sometimes, you have to stick to your guns.

Over the past few weeks, I went through a full process—conversations, diligence, and ultimately, an offer for 10% of the company valuing @oatfinhq at $3M.

In the end, I decided to pass.

Not because it wasn't a good opportunity—it was. But because at this stage, with real ARR, low churn, and a profitable business, it didn’t feel like the right fit. More importantly, we last raised at an $8M valuation.

Accepting a $3M valuation would have been a massive "down-round" signal and, frankly, a bad deal for our existing investors who backed us early.

One thing I’ve learned as a founder: not every “yes” is the right yes. Sometimes the most important decision is saying no to preserve the long-term integrity of your company.

Conviction matters.

Onward.

[Jay Paulynice @jpaulynice]

In building @OatfinHQ, I’ve realized that being stubborn is actually a superpower.

As kids, we’re often told stubbornness is a negative trait. In the startup world, it’s often exactly the opposite.

Early on, I was told so many things: our space was too crowded, the timing was wrong, we should pivot. The advice came from people I respect—investors and mentors who genuinely wanted us to succeed.

It would have been easy to listen. It would have been “logical” to pivot.

But I stayed stubborn.

I stayed obsessed with the problem we were solving, even when the data didn’t make sense to anyone else yet.

Today, that stubbornness is exactly why we’re still here—and growing.

Expert advice is a great data point, but it isn’t a roadmap. In the end, you have to be the one who believes in the vision when nobody else can see it yet.

[Jay Paulynice @jpaulynice]

@hthieblot Porsche

[Jay Paulynice @jpaulynice]

What are you vibe coding this weekend?

[Jay Paulynice @jpaulynice]

Most startups don’t fail because of bad ideas.

They fail because their infrastructure becomes unmanageable faster than they can scale it.

[Jay Paulynice @jpaulynice]

For a long time, my voice here was about survival—getting @oatfinhq off the ground, proving we could even exist.

But 2026 feels… weird.

It’s not a breakthrough year. It’s a forced transition. We’re moving from a scrappy startup to a real company—and that requires a completely different skill set.

It’s trading the adrenaline of the “save” for the discipline of the “system.” Less doing the work. More building the machine that does the work.

This phase doesn’t get talked about enough.

[Jay Paulynice @jpaulynice]

It’s something I struggle with, and I suspect many investors do too. There’s no easy way to say it without crushing a founder’s dream.

Some founders just aren’t credible.

Not because they aren’t smart. Not because the problem isn’t big. Not because the product is bad.

It usually comes down to founder–market fit.

Yes, you found a real problem. Yes, you researched it. Yes, you built something.

But the harder question is: Why are you the right founder to solve it? Have you paid your dues and do you have the battle scars to prove it?

Credibility doesn’t come from decks or demos. It comes from proximity to the problem.

For me, I knew that if I wanted to build a startup one day, I first had to work at one. So after leaving Akamai, I joined multiple startups. Some succeeded. Some failed.

But they all struggled with the same thing: cloud infrastructure.

I didn’t start with a company. I started with a python script — something simple that automated cloud deployments.

Then I went back to the startups I had worked at and showed them how I solved the problem.

Those teams became our first customers.

Founder–market fit isn’t about having the perfect background. It’s about having real scars, real opinions, and real pull from the market. That’s where credibility actually comes from.

You hear a lot about "The PayPal Mafia" and it's a perfect example:

They didn’t just research payments. They lived it. Fraud, scaling, regulation, existential risk. They survived chaos. Made daily high-stakes decisions. Learned hard lessons in real-time.

They earned credibility, not borrowed it from a resume.

Investors trust founders like that, because even if a company fails, the judgment and insight are real.

[Jay Paulynice @jpaulynice]

From a founder perspective, I think with your first startup, you want to prove that you can build something and get customers to pay for it.

And maybe, if things go right, you walk away with a small exit that sets you up to swing bigger the next time.

Once you have that track record, raising money becomes a lot easier — you don’t have to chase investors. They’ll be the ones knocking down your door, trying to invest.

Building a startup is really hard and so in the absence of a track record, investors look at your pedigree (Ivy League material, Google, etc.) to see what you've done over time. It's not a perfect science, but it's a good proxy to judge whether you’re likely to survive the brutal slog of building a company from scratch.

With a track record of execution — even on a small scale — that signal becomes much stronger. Investors don’t have to guess if you can ship a product, find paying customers, and navigate early-stage chaos; they can see it in your history.

In short: your first startup is less about the size of the exit and more about proving you can execute. Everything else — funding, bigger opportunities, credibility — tends to follow naturally once you’ve demonstrated that ability.

[Jay Paulynice @jpaulynice]

It sounds counterintuitive, but one thing I’ve learned building @OatfinHQ is that you have to ignore your competitors.

Everyone says you need to "watch the market" and "benchmark the competition," but obsessing over what others are doing only distracts you from the hard work of building your own product, serving your users, and iterating fast.

Take pricing as an example. When we first launched, one of our competitors charged $49/month. At first, we were tempted to match it—but we realized that doing so would undermine our value and create unnecessary pressure on early growth. Instead, we focused on solving real problems for our users. The right pricing became obvious from the value we delivered.

We could have undercut them, but then it would just trigger a race to the bottom—and nobody wins there.

So we went a different route: we introduced a free Community Edition, while pricing the SaaS edition at $299/user/month and the Enterprise Edition at $2,999/user/year. This allowed us to deliver real value, give users options, and avoid competing on price alone.

[Jay Paulynice @jpaulynice]

Being a founder and angel investor puts me in a unique position: I see both sides of the table.

I understand the pressure, uncertainty, and trade-offs founders face every day — because I’ve lived them — while also thinking critically about what makes a startup investable.

It gives me a sharper lens for spotting opportunities, mentoring effectively, and making decisions that balance risk and growth.