3 things that almost made TWS go out of business

DISCLAIMER: THIS IS BROUGHT TO YOU BY XERO. Xero is a cloud accounting software, designed to make life easier for small businesses. Take control of your finances online, anytime, anywhere, all-in-one platform

It’s 2023, and it’s crazy to think that we’re still running our blog – The Woke Salaryman.

Here’s a short recap, in case you’re a new reader:

  • We started this as a side hustle in 2019
  • We decided to go full-time during the pandemic (2020), abandoning our day jobs
  • We rented a smol office and made our first hire in 2021
  • We rented a slightly nicer office and expanded our team to 4-6 people (including ourselves) in 2022

How is it going? We’re not bankrupt yet. And we’re also not making losses. Phew.

Of course, along the way, there were many times we could have been easily put out of business. Some of these were self-inflicted, and others were because of macro-factors well beyond our control.

Here are three of the biggest mistakes that came closest to sinking us.


At the start, we were resistant to the idea of relying on government support.

The first was simply because of time constraints.

Government grants often required us to invest time into paperwork and multi-stage application processes. Time was simply not something we had the luxury of.

Secondly, we read of many companies in Singapore that abuse grants to sustain an otherwise unfeasible business. Without any legitimate customers, we felt that this was an unethical waste of taxpayer dollars.

There was also a sense of pride that we didn’t need to rely on grants to run our business. That’s okay, but we might have gone a little further to not even consider ANY grants/support.

But that was flawed thinking.

20% of businesses fail in the first year, and young businesses need all the safety margin they can get, so financial support is important.

As long as you’re not abusing grants or schemes, there’s nothing to feel guilty about. After all, support schemes are mutually beneficial arrangements for the company and usually a city/government.

It works like this: governments and cities need businesses because businesses drive the economy and jobs, so many people will benefit from your success.

So the grant granter (lol) is not just helping you for fun; they will benefit from you succeeding.

With that said, we eventually did take on some support after our friends nagged us to look into it.

For example, when we made the leap to hire our first colleagues, the JGI (Jobs Growth Incentive) gave us the confidence to hire, because it initially subsidised 25% of their salaries.

This helped to take some of the financial pressure off us, and also made the additional cost of renting a physical office easier.

It helped that this was automatically disbursed to us too, so we didn’t even have to do tons of paperwork.

If you’re a business/job seeker, consider tapping into some of the support schemes and grants announced recently in Budget 2023 aimed at:

  • Employment support. Multiple schemes are available to provide wage offsets and encourage business owners to employ selected groups of workers, such as lower-wage workers, workers above 60, people with disabilities and ex-offenders
  • Dealing with cost pressures. Enhanced Enterprise Financing Schemes have increased loan quantums to support cashflow needs in light of inflationary pressures. The Energy Efficient Grant also aims to bring down energy costs for selected sectors
  • Sustaining innovation. The Enterprise Innovation Scheme supports R&D, innovation and capability development activities.
  • Encouraging corporate volunteerism. Under the Corporate Volunteer Scheme, businesses enjoy 250% tax deduction on wages and qualifying expenses when their staff volunteer or provide services to IPCs.

Also, check out these schemes if you are also running a small business in Singapore:


(Wei Choon) having run this page with just Ruiming for two years, it was hard trusting someone else to do the work.

We don’t like relying on others and every time we needed something done, we would learn how to do it ourselves. As a result, we ended up being able to do a bit of everything.

Perhaps this comes from pride as well, because it was comforting to think that “only we can do this properly”.

Whatever it came from, it held us back quite a bit, because of scalability.

‘Doing everything yourself’ works when you’re a solo freelancer, but when the amount of work increases beyond what is humanly possible for one person, then it’s best to get some help.

Eventually, refusing to let someone else do the work hurt us.

Ruiming, who handled both writing and client management, struggled to write content and became perpetually mentally exhausted. He sent invoices late, was late for client meetings, and suffered from creative blocks.

As for Wei Choon, he became the bottleneck in terms of production output, since drawing comics is often the slowest process and he was the only artist. This translated to delivering work late to clients, and the inability to create new content for our readers.

We eventually did two important things:

  1. Hire and expand

We looked at the most bottlenecked areas of the business and sought to unclog those lanes by expanding the team.

For account management: We hired an account manager who now deals with clients on Ruiming’s behalf. She came from one of our ex-clients, DBS.

For illustration: We hired two additional illustrators. We’ve also had a couple of interns that drew for us along the way.

  1. Automate the stuff we sucked at/disliked

In addition to hiring for the admin stuff, we also looked for digital solutions. One of the biggest headaches was filing taxes and accounting.

We may like personal finance, but we find collecting, organising and filing receipts too tedious. In the end, we automated some of our accounting stuff to a cloud-based accounting software called Xero.

For the day-to-day, this made checking for payments and transactions a lot easier. And when it came to tax filing season, having transactions auto-populated for outsourced accountants to review reduced the amount of pain everyone had to go through significantly.

It might seem like a small thing, but given that we’re a smol company, how we spend our time is extremely important – we don’t have the luxury of manpower, funding or scale that some of our larger, more established competitors have.

Furthermore, if there are already digital solutions to be more efficient, then us not adopting digital solutions is creating a disadvantage for ourselves.

The less time we spend on things we suck at, the more time we have on things we are good at.


In our first year operating TWS, it felt like we were pushing the very cutting edge of content creation.

Because it was just the two of us making stuff from our respective bedrooms, we moved and grew rapidly. Each week, our page experienced exponential growth as we presented topics and formats previously not seen in personal finance.

Two years in, it felt that we had pushed the boundaries enough such that we could afford to rest on our laurels and coast for at least 3 more years.

This turned out to be not the case.

As it turned out, our initial success put us at real risk of becoming complacent.

We also had to deal with rapid changes in the social media landscape

Rise of competitors. It took a while, but many other people have caught on to using comics to explain complex topics such as investing and personal finance.

Unlike 2019, today our comics compete with many others for attention. We’re also very aware of the fact that we’re no longer the ‘newest kid on the block’, and hence not as ‘indie’ as we used to be.

Changes in social media algorithms. As a social media content page, we have a love-hate relationship with social media platforms.

We love being able to reach hundreds and thousands of people at relatively low cost. But at the same time, we dislike being at the mercy of algorithms – which decide what users (see and don’t see).

Case in point: When Facebook and Instagram changed their algorithms to mimic TikTok’s success, short videos were prioritised over photo albums on users’ feeds. As our comics are exclusively photo albums, this was a problem.

It made us realise that we needed to reduce our reliance on one single platform; as this could disrupt our business overnight.

To counter this, we started several things:

  • We created content for LinkedIn and TikTok; which now surprisingly allows photo albums to be uploaded (thanks TikTok).
  • We started a podcast on YouTube and Spotify; creating a new format of content, different from our webcomics.
  • We created a Telegram channel and Substack email newsletters, both of which are immune to social media algorithms

We knew that change would come eventually, but we just didn’t expect it to come so fast. We didn’t get to coast much, sadly.

But, the bigger lesson is this: In content creation, it’s not enough to try to stick to a tried and tested formula. Creating new stuff HAS to be a vital part of your business when it comes to content creation.

Change becomes harder as you scale

An additional caveat to this is that when you become bigger, you move slower, so adapting to change can actually become harder.

In our case, with client obligations, established SOPs that the whole team was following, and established reader expectations, it was much harder to make dramatic changes than before.

It really goes to show just how fast the rate of change is ramping up. The emotional driving force of TWS’ creation is driven by our frustration for our previous companies’ slow pace of change.

Now, we were the ones struggling to change!

What’s next?

It’s been four years since we started The Woke Salaryman.

So far we are still profitable, we have a small office, 4 full-timers and an intern or two from time to time. Ruiming still writes, and Wei Choon still draws, but we do less of each, and we do a bit more of other stuff.

Who knows where we will be in another four years – or even one year from now.

If there’s a recurring theme that we’ve noticed, it’s that while many of the problems are external, the remedy often requires internal rewiring, which is both easy and hard.

Easy, because you have more control over internal stuff, like admin and finances.

Hard, because often the hardest thing to change is yourself.

Stay woke, salaryman.

A message from our sponsor, Xero

One of the funniest ironies in our business journey has been the idea that one of our biggest internal issues was the fact that we were not getting enough external help.

To that end, it has been an absolute lifesaver for us to have outsourced the bulk of our accounting stuff to XERO, which is also the sponsor of this article.

Xero is a cloud accounting platform designed for startups and SMEs.

They also have guides for businesses, from tips to get started for new businesses to how to scale and grow your business once established.

We use Xero and we like Xero.

Want to take more control of your business? With Xero you can. For TWS readers only, get 50% off your first 4 months when you sign up by 28 Feb with the code TWSXERO. T&Cs apply*.

Find out more at: https://www.xero.com/sg/campaign/take-control-of-business/

*Sign up using the promo code TWSXERO to get 50% off for four months. This offer is only available to organisations new to Xero that are based in Singapore. Offer available until 11:59pm SST on 28 February 2022. Discount applies to base Starter, Standard and Premium plan subscriptions only. Offer cannot be used in conjunction with any other plan or conversion offer, does not apply to add-ons and cannot be exchanged for any other Xero offer. At the end of the offer period, the plan will be charged at Xero’s standard rates.

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