In this series, AsiaOne speaks to individuals who find themselves changing careers and steering their lives in a new direction, whether by choice or circumstance.
Jon Yongfook Cockle did what many wouldn't at the peak of their career in 2018.
Then 38, he quit his job in Singapore as Aviva's Head of Digital Product & Design to bootstrap his own startup. He also set himself a formidable challenge: to launch one product every month for a year.
By his own admission, his corporate career looked great on paper. He was drawing a good salary of about $20,000 a month and was also leading a great team. But something gnawed at him.
The experienced software developer shared with AsiaOne that it was clear to him that he had "reached the peak of [his] career".
"Any higher in rank and I would be looking at a much more political-style role where your job is more about influence and relationships rather than hands-on building stuff.
"I'm really good at the latter, and terrible at the former. So I had nowhere to go."
He has also lamented on his blog that his product building muscle had "atrophied" after nearly three years of corporate life.
While he realised that "lots of people sit happily at the peak of their career until they retire", Jon was in pursuit of something else.
"I wanted to try creating a product by myself that I could sell and turn into a business," said the UK-born entrepreneur, whose mum is Singaporean.
So quit he did, and for the first seven months, he delivered on his promise, shipping one product every month.
It certainly helped that before he left his job, he had saved up more than $200,000 in cash and liquidable assets. The comfortable financial cushion meant he did not have to make drastic changes to his lifestyle after he quit.
On social media, where the 41-year-old has a sizeable following (close to 14,000 on Instagram and 25,000 on Twitter), it's easy to be envious of his lifestyle, where he "changes countries every few months".
But don't let the glamorous photos of his travels across Southeast Asia and Europe fool you — the guy has discipline.
"I don't work by the pool, or by the beach. I don't have a 'four-hour work week' — I actually keep a fairly strict schedule of working 8am to 4pm every day from a proper coworking space.
"I sit with the same people every day and we have become good friends, similar to how things might be in a regular office with your coworkers, except in my case everyone is working on their own thing rather than for the same company."
Of course, due to the lockdowns, his feet are firmly planted in Bali for now. It helps that the island is where he also found success in the love department. He joked that he met his girlfriend, who owns a home-baking business, "the old-fashioned way... on Instagram".
Save, save, save
Paving enough of a financial runway so you don't have to worry about money while having time to build your product is essential, according to Jon.
"If you're selling a digital product or software product and you're starting from scratch, in 99 per cent of cases it has taken years to crack $10,000 in monthly revenue.
"So yes, I would be realistic and say, if this is something you want for yourself you have to be prepared to go a year or two with no income!"
But the tipping point came on the heels of his seventh product launch. It was then that he realised that juggling multiple products wasn't working. And none of his products were able to provide a sustainable income he could live off of.
By then, his once substantial savings had whittled down by more than half. Of the reality check, he shared that he had "two years of savings but only got serious after burning one year of it".
Seeing his assets dwindling provided the impetus for Jon to pivot and change course.
Knuckling down, Jon decided to focus on one area of interest — auto image generation. In Jan 2020, he launched Bannerbear, a software which scans users' websites to generate Instagram Stories, Pinterest Pins as well as Open Graph images.
Finding the passion to solve a problem
In hindsight, Jon realised that his focus on auto image generation in particular was spurred by a pain point from his corporate experience.
"I had worked in an e-commerce company where we would manually create visual assets every day for all the new products uploaded to the store. It was a tedious process that I would have loved to automate at the time, but there was no solution.
"My North Star became trying to create a product that would have solved that past problem, for companies in the future."
Another thing he also noticed was that from that point on, he began to enjoy his work a lot more.
Within a few months, Bannerbear's revenue grew from a few hundred to US$1,000 (S$1,343) a month, then soon doubled.
By the end of 12 months, Bannerbear was hitting US$6,000 in monthly recurring revenue (MRR), a metric widely used by subscription-based businesses. In January 2021, that number climbed to US$10,000. As of writing, Jon is just a few hundred shy of matching his previous corporate salary.
If you're curious, Jon publishes his revenue stats in real time here.
And to cap it all off, two products he'd rolled out as part of his personal challenge were acquired at the end of 2019, he revealed.
The next goal for Jon? "To grow the business to $1 million in annual revenue."
'Pricing is hard, charge more'
On Twitter where Jon regularly shares his independent startup journey, it is evident that his story is an inspiring one among the indie-hacking circle.
While he's not sure if he has inspired people to quit their jobs, he shared that at the least, "I've shown people that it's possible to grind your way to replacing your full-time salary with revenue from a self-built product."
Trying to distill more secrets of his success, we asked what the biggest lesson he has learnt so far is.
Deciding on the optimum pricing — a notoriously difficult but necessary task for entrepreneurs — is definitely one of them.
"Probably my biggest lessons have been related to pricing of products," shared Jon.
"Engineers have a tendency to underprice their products, and believe that it's impossible to charge higher prices. This is almost always untrue, and in fact usually when you raise prices you find yourself dealing with more serious customers, with more interesting problems to solve, who will stay with you for longer."
This is reiterated in a blog post looking back on his US$10,000 MRR milestone: "Pricing is hard, charge more."
But success even after three years is not guaranteed for many reasons. Besides having sufficient savings, experience counts for budding entrepreneurs wanting to go at it alone.
“Most software developers like me have a dream of creating an original SaaS (software as a service) product, and living off the revenue.
“I think if you're looking to make the jump and work for yourself whether it's in terms of doing freelance work, or building your own service or product, you should have at least five years of industry experience. Ideally 10 years. By the time I left my last job, I had about 20 years of experience in building software products.”
As for when it's time to throw in the towel, Jon has this piece of advice: "If you find yourself burning out, take a step back or work on a new project for a while. You won't do your best work when you're frying your brain or giving yourself anxiety."
For Jon, the moment when he moved beyond US$3,000 in MRR to close in on US$6,000 was when he realised he had reached a sweet spot in his "career".
Sharing his experience on the Indie Hackers website, he wrote: “It feels almost like a job, but a really awesome job where there's a sense of stability but also a sense of ownership.
"Being an indiehacker: 10/10 would recommend."
It's no wonder that he doesn't see himself back behind an office desk and working for a company anytime soon, if at all.
"I don't think I can, really. I was already at the tail end of my corporate life so it would be strange to go back, and I don't think I'd be very useful!"
This article has been edited for clarity.