Office Hours: What's the Most Annoying Thing About Investors?

And what to do about it.

“What's the most annoying thing about investors?” Hsu Ken asked in a LinkedIn poll.

Turns out, there were a lot.

Even though ‘overly generic feedback’ won the poll, founders added other things they found unhelpful into the comments. Things like…

While we can't account for every investor, we thought it'd be helpful to give more context into why these happen.

In this month's Office Hours newsletter, Hsu Ken dives into some of these traits founders had a stronger reaction to - and how to navigate through them.

Question of the Month

What’s happening behind the scenes to give founders these impressions?

Hsu Ken: Having spent most of my career as a founder and the last few as an investor, I see both sides now. Like in any industry, there are bad actors (both investors and founders) but the majority of people are good and trying to do a good job. The founder and investor dynamic is particularly sensitive for three reasons.

First, the power dynamic between founders and investors - typically, it's in the investors’ favour. Second, the sheer volume of rejections founders have to endure. Third, how important fundraising is for the founder’s company. The company may cease to exist if they aren’t successful.

That’s why it’s important for investors to empathetic during the fundraising process but also for founders to prepare themselves for how difficult the process is.

Let’s jump into some of the topics that were brought up in the original thread. My goal is to translate what the behaviours mean and highlight what's (probably) happening on the investor’s side.

1. Ghosting or Being Vague – They’re not that interested but aren’t telling you directly because (1) they are busy and writing a thoughtful rejection takes time or (2) they want to preserve their optionality in case they change their mind.

2. Lacking Empathy – Most investors try to empathise with founders but the reality is most investors haven’t been founders. It’s not impossible but it’s harder to empathise when you haven’t experienced it yourself. Being founder is such a unique experience.

3. Overestimating Value Add – I kind of shrug at this one a little. Investors think they can add a lot of value and founders think their company is going to change the world. Both are opinions that will be proven long term. It’s up to the other side to decide whether they believe them or not. That’s the game.

4. Lacking Operating Experience – Related to my response on empathy above. The Southeast Asia ecosystem is young. There’s a lack of operating experience across the board (founders, investors, etc.). We’ll get there :)

5. Having More Opinions Than Analysis – Unfortunately, investors see more pitches than they have time to do deep, thoughtful analysis on. As a result, they have to quickly prioritise the small minority of pitches (probably less than 5%) to learn more about. That prioritisation is done based on what an investor thinks is interesting, which are opinions informed by previous analyses, what they’ve learned, talking to people, etc.

I’m not condoning any of the behaviours above but I do think there’s often a misunderstanding on what the other side is like. It’s not going to change overnight but I do think we’re headed in the right direction.

Given things won’t change overnight, here are two things founders should keep in mind when fundraising.

1. Don’t Take It Personally – Easy to say but remember an investor is just a person with an opinion. People have different opinions and that’s okay. If they disagree with you, it doesn’t mean you’re dumb or doing something dumb. They just have a different opinion on what they think will happen. Plenty of investors have been wrong and missed out on some of the biggest companies (us, included!).

2. You Have Agency – Remember that you have agency. If you don’t like how an investor is treating you or don’t think they believe in what you’re doing, you can walk away. You don’t have to have them as an investor. It might not feel like it sometimes but founders are not beggars - you get to choose who you do business with.

At the end of the day, you only need a handful of investors to believe in what you’re doing and you get to choose who they are.

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Until the Next One…

Alternatively, if you have any other startup questions you'd like for Hsu Ken or Brian to answer, just hit reply and let us know! You can also leave comments directly in our Substack.

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