🧪 From product marketer to bootstrapped multipreneur: career lessons

Marketers Help Marketers

Hello hello 👋🏽,


Welcome to the 12th edition of Marketers Help Marketers newsletter.

I am really excited about this one.

A couple of weeks ago, I sent a newsletter about product marketing careers, thanks to all the wisdom Siddhartha shared.

This week, I'm diving into Siddhartha's career journey itself.

Let me tell you why his story is so compelling:

  • He's one of India's earliest product marketers who built a thriving corporate career

  • He's a successful bootstrapped multipreneur who built several income streams before leaving his job to build his businesses

He proves you can transition from marketing employee to business owner, gradually validating your ideas while still holding your job.

Because honestly, most of us dream about doing this, very few actually pull it off.

So it’s stories like these that help understand how other marketers made that jump, and what that process actually looks like.

This newsletter is a (highly) condensed version of our 2+ hour conversation, releasing in 2 parts (part 1 dropped today).

As a newsletter subscriber, you always get the good stuff first. 🫶

This one's going to be long, but trust me, it's worth it.

Siddhartha is the kind of marketer who makes you rethink what's possible.

By day (well, formerly), he led marketing at VWO after stints at Freshworks, Sulekha, and Shiksha.

On the side, he laid foundations for multiple businesses: successful Airbnb rentals in Goa, a popular product marketing course at GrowthSchool (now in its 13th batch), and a progressive rock (and profitable) band called Time Throttle that has toured across India.

Oh, and he spent 8 years creating India's largest crossword puzzle, which became a board game, later.

His career path wasn't planned. A PGDM at MICA led to performance marketing at Shiksha.com, then SaaS roles at Freshworks and VWO.

He wanted to work at an advertising agency but ended up in digital marketing. Something he did not want to pursue at the time. But in hindsight, it was the best "thing" that happened to him.

Each role was built on skills from the previous one. A Star Wars May 4th campaign he ran at Freshworks - a side project gave him the confidence to transition from marketing ops to product marketing.

And the rest is history.

Building multiple income streams (the smart way)

What sets Siddhartha apart is how he built several income streams before leaving his job.

While he was still employed full-time, in his free time, he:

Created India's largest crossword puzzle (8 years, 30-40 minutes daily)

Started teaching product marketing (free sessions → paid cohorts at GrowthSchool)

Listed rooms in his Goa home on Airbnb (a highly rated property)

Performed with his band, Time Throttle (who have already done a pan-India tour)

These weren't overnight successes.

They required consistent effort over the years.

So if you are a marketer considering side projects: 

start small but be consistent.

The key is to plant seeds early and nurture them alongside your main career.

Throughout our conversation, Siddhartha shared several career principles that shaped his path.

These insights apply whether you're planning your own leap or just want to grow faster.

Finding your footing takes time

Here's a truth that applies to most careers: it takes time to find your footing.

People take usually three jobs or seven years to find a good footing.

Siddhartha Kathapalia

Siddhartha had four jobs in five years before finding stability at VWO. Then he spent four years growing within the same company before going solo.

For early-career marketers feeling lost: you're right on schedule. If you're in your first or second marketing role and still figuring things out, that's completely normal.

Focus on the relevance of opportunities in the next 2-3 years

Siddhartha judges career moves on a 2-3 year horizon. Most of us can't predict beyond that anyway.

Will this role still matter then? Will it unlock multiple next opportunities? If both answers are yes, make the jump.

That mindset led him from performance marketing to marketing operations to product marketing, each time expanding his options.

When considering your next move, ask:

- How will this position me in the next 2-3 years?

- Does it open multiple paths or just one linear progression?

- Will I build transferable skills or just role-specific ones?

Never switch jobs with only one offer

"Have two and choose the better of them so that you have something to compare," Siddhartha advises.

A data point in isolation means nothing. For instance, when joining Freshworks, he also had offers from other companies.

He chose Freshworks because B2B SaaS felt like a growing field that would take him with it.

Do a high volume of work

One approach that consistently worked: taking on many projects simultaneously.

"Pick up 10 projects, two of them will move forward," he shared about his VWO days.

This is especially important if you work in an environment with slow decision-making processes.

Instead of perfecting one campaign for months, try launching multiple smaller ones.

Learn from each, iterate quickly, double down on what works.

The comfort of being “second best”

Siddhartha shared an interesting perspective: sometimes, aiming for "second best" removes unnecessary pressure.

This isn't about settling. It's about setting realistic goals that challenge you while maintaining your sanity.

"Being second best is absolutely fine unless you have that kind of ego, that kind of determination to be the absolute best."

Be in the business of being nice

This one is my favorite.

Siddhartha champions kindness.

"You can be nice and still do business," he learned at VWO.

This philosophy serves him well as an entrepreneur, his Airbnb business as well as product marketing cohort have some of the highest ratings.

Being nice always pays off.

The company is bigger than you

This one's huge and underrated.

Early in his career, he tried changing organizations to fit his vision. This created friction.

Later, he realized his role was enhancing existing systems, not overhauling them.

"I'm not here to change things. I'm here to help the organization work," Siddhartha learned by his fourth job.

External factors matter & impact your career decisions

Sometimes life circumstances dictate career moves.

For Siddhartha, marriage meant moving to Delhi. Layoffs at Sulekha meant preparing for change.

Recognize when external factors drive decisions. Embrace them rather than fight them.

Teaching to learn

"Everyone should have a teacher and everyone should teach. This is the Yin-Yang concept."

Siddhartha Kathpalia

To master something, teach it.

"If you can mentor someone, you should do that. Because while answering questions, you get more clarity."

His teaching journey: free sessions → small Zoom groups → structured course.

"You'll be asked questions you've never thought about. You'll be asked to define things you take for granted."

This process forced him to clarify his thinking and deepen his expertise.

These are just the highlights from our 2+ hour conversation.

There's so much more in the full episode -

stories about his band's marketing strategies (how he uses his product marketing chops there), how he built his Airbnb empire from scratch, and his framework for making career decisions.

If you're curious about the entrepreneurial path or just want more career wisdom, the full episode is worth your time.

In conclusion

What struck me most about Siddhartha was his balanced approach to success.

He doesn't chase growth at any cost. Instead, he prioritizes fulfillment while building sustainable businesses.

"If given a situation where there's aggressive growth or slow-paced growth but with a good feeling, I will go for the good feeling."

His parting advice:

"Most projects you pick up will fail. A few will succeed and a few will succeed disproportionately. The idea is to find those disproportionate ones."

Siddhartha Kathapalia

This perspective reminds us that marketing, like life, is about experimentation, resilience, and staying true to yourself.

As always, I'd love to hear your thoughts. Just hit reply or find me on LinkedIn.

Have an amazing week ahead! ✨

Your marketer friend,
Mita ✌🏽