3x Exit Founder • I help B2B founders in Southeast Asia • Book a free growth consultation with me • Grew last company to $5m+ ARR • 15+ years of growth leadership 🚀

Hey there! I’m a serial entrepreneur with 3 exits under my belt. 

I’m currently working on Kubegrade, a Kubernetes cluster upgrade tool.

Through all my ventures the key to success has always been to bring maximum value to my clients and building long lasting relationships. 

My passion for client success is equally matched with my love for travel and extreme sports. 

You can find me playing chess, riding motorcycles, diving or kitesurfing the beautiful beaches of Southeast Asia.

Tim Grassin

My wife knows when I'm stuck on a problem.
I get quiet at dinner. I stare at nothing. I wake up at 3am and reach for my phone to write something down.

15 years of startups and it's always been like this.
The problems don't clock out when you do.

𝗧𝗵𝗲 𝘁𝗵𝗶𝗻𝗴 𝗻𝗼𝗯𝗼𝗱𝘆 𝘁𝗲𝗹𝗹𝘀 𝘆𝗼𝘂:
The mental load follows you everywhere.
Dinner with friends? Half your brain is on that product decision.
Vacation? You're thinking about the pipeline.
Sleep? Your subconscious is debugging that user flow.

When we were scaling TendoPay, I'd lie awake running scenarios. 
What if this enterprise deal falls through? What if that feature launch flops? 

What if we're building the wrong thing?
Some of my best solutions came at 2am. Some of my worst spirals did too.

𝗧𝗵𝗲 𝗽𝗮𝘁𝘁𝗲𝗿𝗻 𝗮𝗰𝗿𝗼𝘀𝘀 𝘁𝗵𝗿𝗲𝗲 𝘀𝘁𝗮𝗿𝘁𝘂𝗽𝘀:
Startup #1 - I thought the mental load meant I cared. I wore exhaustion like a badge. Burned out before 30.
Startup #2 - I tried to compartmentalize. Work stays at work. It doesn't work that way. The problems don't respect boundaries.
Startup #3 - I finally accepted it. This is the deal. The mental load is part of the job. Fighting it makes it worse.

𝗪𝗵𝗮𝘁 𝗜'𝘃𝗲 𝗹𝗲𝗮𝗿𝗻𝗲𝗱:
→ The 3am ideas are often good
Keep a notes app ready. Some of my best product decisions came from half-asleep clarity. Write it down, go back to sleep, evaluate in the morning.
→ But the 3am spirals are usually lies
Anxiety at night amplifies everything. That "catastrophic" problem usually looks manageable at 9am with coffee.
→ Your partner sees it before you do
My wife can tell when I'm carrying too much. She's been through three startups with me. When she says "you're not here right now",  she's right.
→ Movement helps more than thinking
When I'm stuck, I go ride my scooter around Bangkok. Or play padel. The solution usually shows up when I stop forcing it.

𝗧𝗵𝗲 𝗿𝗲𝗮𝗹𝗶𝘁𝘆 𝗼𝗳 𝗯𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗞𝘂𝗯𝗲𝗴𝗿𝗮𝗱𝗲 𝗻𝗼𝘄:
My co-founder Caleb is in a different timezone. Sometimes I wake up to messages that need decisions. Sometimes I fall asleep thinking about what we discussed.
The mental load hasn't decreased with experience. I've just gotten better at carrying it.

I know which thoughts are worth chasing at midnight and which ones to let pass.
I know when to grab my phone and write something down, and when to breathe and go back to sleep.
I know that my wife checking in isn't nagging, it's her seeing something I can't.

𝗧𝗵𝗲 𝘁𝗿𝘂𝘁𝗵 𝗜 𝘁𝗲𝗹𝗹 𝗻𝗲𝘄 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀:
This doesn't go away.
You don't reach a level where you stop thinking about the business at dinner. You don't hit an ARR number where the 3am wake-ups stop.
The goal isn't to eliminate the mental load.

It's to build a life that can hold it.

A partner who understands. Movement that clears your head. The wisdom to know which midnight thoughts matter.
Entrepreneurship isn't a job. It's a life that includes a job.

Accept it and carry it.

Kubernetes without the complexity. Developer visibility, platform guardrails. Works with EKS, AKS, GKE, Rancher and more.

We rebuilt our onboarding from scratch.

Here's why and what it means for you.

𝗧𝗵𝗲 𝗣𝗿𝗼𝗯𝗹𝗲𝗺:

New users were getting stuck.

Too many clicks. Not enough context. Unclear next steps.

We heard it directly: "I signed up but didn't know where to start."

That's on us. So we fixed it.

𝗪𝗵𝗮𝘁 𝗪𝗲 𝗖𝗵𝗮𝗻𝗴𝗲𝗱:

→ Step-by-step guidance from first login
No more guessing. Pop-ups walk you through exactly what to do next.

→ Clearer UI and actionable menus
Buttons that make sense. Next steps that are obvious.

→ Built-in assistant
Stuck? Get help instantly without leaving the platform.

→ Resources for every skill level
Deep K8s expertise not required. We added non-technical resources so anyone can follow along.

→ Smarter cluster connection flow

Connecting your first cluster used to be confusing. Now it's straightforward.

𝗧𝗵𝗲 𝗥𝗲𝘀𝘂𝗹𝘁:

Users go from sign-up to "I get it" faster than ever.

Less confusion. Fewer support tickets. More time actually using the product.

And if you ever need to revisit onboarding? It's always there. One click away.

𝗪𝗵𝘆 𝗧𝗵𝗶𝘀 𝗠𝗮𝘁𝘁𝗲𝗿𝘀:

Kubernetes is complex enough. Your tools shouldn't add to the chaos.

We want you productive on day one, not week two.

That's the bar we're holding ourselves to.

Thinking about trying Kubegrade? There's never been a better time to start.

#Kubernetes #DevOps #ProductLed

A founder on Reddit shared something wild:

"We spent $14k on coaching pre-revenue. 78% of our total expenses."

The comments were brutal. And fascinating.

Here's what the thread revealed about why founders skip coaching and when it actually works:

𝗪𝗵𝘆 𝗲𝗮𝗿𝗹𝘆 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀 𝘀𝗸𝗶𝗽 𝗰𝗼𝗮𝗰𝗵𝗶𝗻𝗴:

Every dollar feels like your last dollar.

Credibility is impossible to verify until you've paid.

"Those who can't do, teach" echoes in your head.

Free advice exists everywhere. Why pay?

You think you'll figure it out yourself.

Ego. You don't want to admit you need help.

𝗧𝗵𝗲 𝗿𝗲𝗮𝗹 𝗿𝗶𝘀𝗸𝘀 𝗥𝗲𝗱𝗱𝗶𝘁 𝗰𝗮𝗹𝗹𝗲𝗱 𝗼𝘂𝘁:

"Bad coaches sell confidence, not competence."

Generic frameworks applied to every problem.

No skin in the game. They get paid either way.

"If I were an investor, I'd see this as disqualifying."

The best mentors don't need your money.

One comment: "You're paying to reduce the burden of being responsible."

𝗪𝗵𝗮𝘁 𝘁𝗵𝗲 𝗼𝗿𝗶𝗴𝗶𝗻𝗮𝗹 𝗳𝗼𝘂𝗻𝗱𝗲𝗿 𝘀𝗮𝗶𝗱 𝘄𝗼𝗿𝗸𝗲𝗱:

Found someone with a real track record. 3x founder. YC alum. Meta acquisition.

First free session showed them they were building the wrong thing.

They pivoted immediately. Saved years of wasted effort.

"The value wasn't answers. It was better questions."

Solo founders need someone who isn't their spouse to vent to.

No regrets, even with the skeptics piling on.

The thread surfaced a filter I keep thinking about:

Would the coach take equity instead of cash?

If they won't bet on you, why should you bet on them?

I've been on both sides of this. Paid for advice that was worthless. Also had 
mentors who changed my trajectory completely.

The difference was never the price. It was alignment.

What's your take? Is paid coaching worth it or a trap?

My only new year's resolution for 2026
↓↓↓
Keep showing up

If no one invests in you, invest in yourself

If no one believes in you, believe in yourself

Even if you don’t see the results right away

Keep showing up until you do see the results

Even if you don’t see the results for a very, very long time

Keep showing up

What if the results don’t come?

They’re not going to come if you quit, keep showing up

“I’m tired"
↳ keep showing up
“I don’t feel like it"
↳ keep showing up
"I can’t see any results"
↳keep showing up

I don’t know where to start

Just start, do something

Take that first step, every step you take adds up

And sooner or later
You’ll look back and see you’re at the top of that staircase

It doesn’t matter if you can’t see the top from where you are

Just know that if you keep climbing

If you keep learning how, you can get to that next level

You will soon be exactly where you need to be

If you quit, if you’ve never start climbing

If you’ve never take that first step, you’ll never get there

And you’ll forever live in regret

People don’t make it because they quit, full stop

 → They say they tried everything, sure they tried everything
 → They tried everything, but sticking it out
 → They tried everything, but courage to keep going
 → They tried everything, but showing heart when things got hard
 → They did try quitting, winners do not quit!
 → They show up, rain, hail, or shine
 → They show up when it works

When it’s hard, they show up every single damn time

And that, that right there is the difference, keep showing up

Rain, hail, or shine, success is mine

Hard or easy, slow or long, success is mine

Feel like it, don’t feel like it, success is mine

Failure, setbacks, naysayers, success is mine

A founder on Reddit launched in 23 places over 2 weeks.

94 signups. 12 paying customers. Felt like momentum.

Then the comments started rolling in:

"This is an ad disguised as a story."

"We know none of your successes ever happened."

"Don't scatter links where you can't monitor."

Here's what the thread actually revealed about multi-platform launches:

𝗪𝗵𝘆 𝗶𝘁 𝗳𝗲𝗲𝗹𝘀 𝗽𝗿𝗼𝗱𝘂𝗰𝘁𝗶𝘃𝗲:

Upvotes are visible. Revenue is not.

23 submissions = 23 dopamine hits.

"Spreading surface area" sounds strategic.

Traffic trickles in from everywhere. Feels like growth.

You're busy. Busy feels like progress.

Way better than staring at an empty dashboard.

𝗧𝗵𝗲 𝗮𝘁𝘁𝗿𝗶𝗯𝘂𝘁𝗶𝗼𝗻 𝗽𝗿𝗼𝗯𝗹𝗲𝗺 𝗻𝗼 𝗼𝗻𝗲 𝘁𝗮𝗹𝗸𝘀 𝗮𝗯𝗼𝘂𝘁:

94 signups from 23 sources. Which ones actually convert?

Some directories sent 2 signups. Some sent 15. Which paid?

Product Hunt sends tire-kickers who rarely buy.

One niche directory sent the best customers. But which one?

Without UTMs and tracking, you're guessing.

"It all added up" isn't a strategy. It's hope.

𝗧𝗵𝗲 𝗰𝗼𝗺𝗺𝘂𝗻𝗶𝘁𝘆 𝗽𝘂𝘀𝗵𝗯𝗮𝗰𝗸 𝗽𝗿𝗼𝗯𝗹𝗲𝗺:

"Helpful posts with product mentioned" still reads as self-promo.

Mods and members spot it instantly.

Your reputation burns faster than your traffic grows.

One bad post can get you banned from a valuable community.

Story-as-ad is the most hated format on Reddit.

The founder deleted their account. The comments stayed.

Here's the uncomfortable truth:

Launching everywhere feels like distribution.

But if you can't trace which channel moves revenue, not signups, revenue, 
you're collecting vanity metrics.

12 paying customers from 23 platforms sounds good.

Until you realize you have no idea which 3 platforms actually mattered.

The real strategy isn't launching everywhere.

It's launching somewhere, measuring ruthlessly, then doubling down.

Have you fallen into the "launch everywhere" trap? What actually worked?

#Startups #IndieHackers #ProductLaunch #Marketing

Nick Santora

CIP Cybersecurity Specialist

NovaSync

VP of Growth

aijobs.com

The world’s official free AI job board marketplace.

Founder

PEF Community

Private membership group for post exit founders.

Member

Figure

Investor

OpenAI

SpaceX

Infinite Giving

Investor & Advisor

Mercury

Copy.ai

Hi I'm Nick, currently the VP of Growth at NovaSync. I also advise and invest in cool startups doing cool things. 

__________________________________________________________________________________________

I created a company named Curricula which I led to a $22M exit in 2022. Our small, resourceful animation studio produced a fun animated series of cyber security awareness training content delivered through our custom built cybersecurity focused e-learning SaaS platform. That platform includes a phishing simulation engine that actively engages with employees simulating real-world hacker defense training. 

Curricula is used by thousands of organizations across the globe to help their employees defend against hackers. Curricula supported over 70+ Million minutes of training watched in 2024.

__________________________________________________________________________________________

Earlier in my career, I founded BCSL Brands, a startup studio focused on developing Internet advertising software and services. I sold that business in 2017.

GM - Security Awareness

Making fun cartoons that help employees defend themselves against hackers. I'm leading the former Curricula team during the transition into Huntress as we scale together.

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