The most common advice when starting a company is “do things that don’t scale,” and that’s absolutely right.
But at some point, if you’re successful, you need to stop doing things that DON’T scale and start doing things that DO scale. That means shifting focus from building the product to building the organization that builds the product.
This is one of the toughest transitions for founders, especially CEOs. Almost nobody gets it right the first time and a surprising number of otherwise successful companies don’t survive the transition.
It’s challenging for a few reasons.
- Counter-Intuitive – You’ve succeeded because you did things that don’t scale and now need to do the opposite. You reached $100K in MRR doing most of the sales yourself, but to get to $1M in MRR, you need to stop selling and build a sales team.
- Pressure to Grow – The pressure to grow never stops. So, changing your focus to things that don’t directly impact growth feels like the wrong thing to do.
- Unclear Steps – Even if you get over how counter-intuitive it is and get comfortable with making the change despite the pressure to grow, it’s not obvious how.
Here’s what usually happens.
- Scaling Things That Don’t Scale – You need to grow, so you try to do more of the things you’ve been doing which don’t scale. Eventually, they stop working and you have to figure out what to do.
- 3.0x Headcount, 0.5x Results – To fix the problem, you start hiring lots of people to scale things that don’t scale and to figure out things that do scale. Founders don’t want to spend all their time interviewing (who does?), so they hire “experienced” people from larger companies. After 6 to 9 months, the founder will realize they’ve tripled their headcount but are executing and growing at half the speed.
- Clean House – After the initial panic, they spend 3 months cleaning house. They fire the “experienced” people, most new hires, and start again. This time, determined not to make the same errors, they prioritize hiring the right people.
There are variations to the story, but if you ask a late-stage founder, they’ll likely tell you a similar story.
I know what you might be thinking. This isn't what you need help with. You need help expanding to a new country, new market, etc. That's what most companies talk to me about.
Surprisingly, the vast majority of the time, after digging into those topics, I find that isn't their first order problem. Yes, they need to do those things but don't have a sufficiently effective organization to support those initiatives.
Southeast Asia Challenges
This transition is particularly difficult in Southeast Asia.
- Fewer Founders – At every stage, there are fewer founders, but it gets thinner the further along you get. That means fewer people to learn from and receive support.
- More Fragmented – In addition to fewer founders, there's more fragmentation (country, language, etc.). That means fewer people to learn from and receive support.
- Less Experienced Teams – There are fewer people who've worked at startups that have made the transition. In SF, there are likely people on your team that have and can help you, even if you haven't. This is not the case in Southeast Asia.
- Lower Salaries – Salaries in Southeast Asia are significantly lower, allowing for larger teams earlier in a startup’s lifecycle. That forces founders to deal with these problems sooner.
We’ve noticed this with companies in and outside our portfolio, so we wanted to create a structured way to help.
Program Details
The Iterative Scale Program is a 6-week program where Iterative invests $1M to $2M into a Seed or Series A company and works with them like our accelerator program but focused on scaling.
The program consists of...
- Orientation – A one-day, in-person kick-off where founders will meet Brian, Hsu Ken, and the other companies in the cohort. The goal is to discuss challenges, share yours, and identify key areas to work on together over the next six weeks.
- Office Hours – Weekly 1:1 sessions with Brian or Hsu Ken to debug your company’s challenges. These discussions help troubleshoot your biggest obstacles and provide tactical guidance.
- Group Office Hours – Bi-weekly sessions where 3-4 companies meet to discuss common challenges. This format allows founders to learn from each other's experiences and get multiple perspectives on scaling issues.
Since this is the first batch, Brian and I will work with these companies directly.
Who Should Apply
We're looking to invest in and work with companies generating over $500K in annual revenue. We understand there’s a lot of nuance here, so take this as a rough guideline.
This originally started as an initiative to support existing Iterative companies, but we thought it might be a good opportunity to work with founders who we missed at an earlier stage.
As a result, this is open to companies in our portfolio as well as those outside it.
How to Apply
The program starts on 4 November 2025, so we’re already talking to companies and our process is fast.
- Send Deck – Send us a deck so we can begin learning about your business.
- Initial Call – If it seems like a good fit, we'll schedule an initial call to learn more.
- Diligence – We’ll write an internal memo based on the initial call and our research. The goal is to understand the business better for the final call.
- Final Call – We do a final call to discuss any questions or concerns that arose while writing the memo.
- Decision – We decide and hopefully make you an offer. If you accept, we transfer our $ immediately.
Our aim is complete this process in 4 weeks.
Apply by sending your deck to terri@iterative.vc.
