Asking for a Hustler

What should founders do next after selling their first companies?

I've been talking to founders who are trying to figure out their next act. These are Southeast Asian-based founders who have exited their previous startups and are now trying to position themselves for the next step in their careers. They know that they ultimately want to found another company, but many other questions arise.

There’s the matter of problem selection, as in what’s the next problem they want to solve as they choose what market to build their business in. Some are considering leaving Asia and moving to the US, while others are considering the business models most likely to succeed in Southeast Asia.

Then there’s the question of what experiences they want to gain next. Is it a functional area, such as more sales or product experience? Or a specific vertical, such as e-commerce or fintech?

Should they pause on entrepreneurship, and get a job? It may sound like a step backwards to some, but if they eventually want to start a fintech company, for example, working at a bigger financial services institution first to see how things operate at scale would be a wise next move.

Here’s how I’ve addressed these general buckets of questions.

Should I move to the US?

Southeast Asia is not a single market but comprises 11 countries with different languages, currencies, and regulatory regimes. By comparison, many founders see the US as the promised land, with higher per capita GDP, a large market size, and a unified language—plus lots of innovation.

But it’s not so simple. Founders should assess their competitive edge before deciding to start a new company in the US, and consider factors like market access and cost competitiveness. If you haven’t grown up there, studied there, or worked there, you are likely working at a disadvantage compared to native founders.

Of course, this can all be overcome, but I find it helpful to push founders to really reflect on what they think their edge is, relative to everyone else, before being seduced by market size alone.

What are the right business models for Southeast Asia?

Thin-margin businesses like marketplaces and e-commerce face challenges in Southeast Asia, and startups may lack advantages that established businesses have, such as well-established distribution.

Exploring innovative business models that leverage AI and human resources could lead to full-stack integrated solutions that compete with incumbents. This approach may be more attractive to private equity investors given the services component, and can be cash-generating out of the gate—especially when compared to traditional pure software tech venture startups.

I recently wrote a post here about greenfield opportunities in Southeast Asia, for a slightly deeper dive.

Should I just get a job?

It can feel attractive to get a paycheck after years of slogging to make payroll. I encourage founders to be strategic in this choice, reflecting on the types of experiences they want to acquire or networks they would like to build for their next startup.

For example, if you're trying to start your next company in the US, but aren't from there originally, perhaps look for a job based in the US first, ideally in an industry you think you might be interested in starting a company in. If you found that your prior company was hindered by lack of sales experience, you might want to go to a company that is well-known for a great sales process and strong go-to-market teams. Perhaps you think that your next business should be in digitizing industrial companies, but you have only worked in pure software. There may be an opportunity to work in an industrial firm to gain exposure there.

At the same time, if you already know and understand the sector you want to build in, there may not be anything new to gain from getting a job.

If you are already at work on your second venture, tell us about it here!

Happy plotting!

Shiyan

This article was written by Hustle Fund Managing Partner Shiyan Koh, based in Singapore. In her spare time she plays Padel, continuously thwarts her children’s efforts to get more screen time, and hunts for the best bak chor mee. 🍜