Critical feedback when you are crapping your pants

Now, that sounds like a pretty crazy title, right? But if you are a founder you will understand what I mean by it.

When you are balancing precariously on a knife’s edge between ebullient confidence of making a unicorn dent in the universe, and dark depression as to whether you really are crazy and you are going to end up homeless, it can seem like the most modest amount of critical feedback will send you crashing into an abyss of self-loathing and wanting to pack everything in.

I say this because I have felt like this many times in my life. I have contributed to building 3 unicorns with strong resources (But not at the start!) which was cool, but many, many more times I have been broke as hell trying to build startups, lost, and frankly frightened. A good or bad word was enough to send me to either side of the knife’s edge I mentioned. So much of startup is in your mind and your confidence.

People don’t talk enough about how completely terrifying and lonely being a founder is. James Altucher is arguably the most emotionally honest blogger you will find. Occasionally, the dark side of entrepreneurship is reported on, there are articles written that founders always say ‘everything is awesome’ only to commit suicide. This is ridiculous. I have a founder friend attempt it.

This article is actually about critical feedback, or rather how I give feedback to different kinds of founders. For whatever reason, I spend a lot of time daily giving advice/feedback to entrepreneurs, so I have a lot of experience in this. I also have a lot of experience in not spending time giving feedback, which drives some people insane. This sounds weird and I will explain why.

Types of founders and feedback provided

There are 8 types of founders in my view:

1. Super nice, completely clueless, but trying like hell (Often with no support)
2. Experienced founder with a real business, scaling well
3. Experienced founder looking to start another business
4. Inexperienced founder building a business well
5. Experienced founder with a real business, scaling poorly
6. Inexperienced founder building a business poorly
7. Inexperienced founder with an idea and is worth helping
8. Inexperienced founder with an idea and is a waste of time

If you graph these founder types across an X axis, with 8 at the right and 1 on the left, then Y axis degree of critical feedback, with critical (aka harsh) (1) at the top and ignore (7) on the base, you can visualize how I engage people. I will explain how and why now.

The type of person you are, the amount of work you have put in and the degree of success you have achieved so far are critical to understanding this.

Super nice, completely clueless, but trying like hell (Often with no support)

This is the weirdest place to start, but it fits the matrix. There are a number of super well-meaning founders around that are simply clueless, but are trying like hell and begging for guidance with no one to help them. My heart bleeds for these guys.

I am the most honest with this category. Quit, read more and join another startup to learn on someone else’s’ dime is the short response. It sounds harsh, but it is like pulling a band-aid off. If done right, they get it. “No one ever said that to me” is something I will hear.

You just have to. Some people are also in really tough situations, and I don’t mean a Singapore HDB, I mean borderline poverty line.

If you really don’t know much, then joining another startup, with clear goals in mind to learn all you can so you can set up again with a better basis of knowledge and network is super-good idea.

Experienced founder with a real business, scaling well

Generally, experienced founders who are doing well should be given a hard time, as it is needed and they can take it. You can and should be direct, though generally, you can’t say too much that is ‘bad.’ Any negative feedback is pretty constructive and immediately actionable, so feedback goes like water off a duck’s back. The founders are confident and appreciate finding any area they can improve on. To be honest, I am more likely to be helping them think through their current challenged, then poking holes.

Experienced founder looking to start a business

Experienced founders starting a business know what they are in for, you can and should ‘let rip’ without need to choose your words carefully. They will typically appreciate being able to validate assumptions so they don’t waste their time. They likely have cash in the bank and see the opportunity cost by doing things wrong. The whole point of a discussion at this stage is to ensure they are solving a good problem, that the market is big and how they are going to solve it will result in an exit. Feedback is a sounding board.

Inexperienced founder building a business well

Inexperienced, but talented founders who have never done startup before but are doing well are great to deal with. They don’t have egos and are super eager to keep learning. In fact, they are doing well because they want to keep learning and so all feedback is golden. I simply love these founders and it is so rewarding spending time with them. More often than not you give feedback and a week later it is already implemented. Discussions are orientated around what needs to be focused on to go faster, who they can talk to to get advice, where to hire staff etc.

Experienced founder with a real business, scaling poorly

Here is where things start getting ‘dark’ on the feedback scale. One needs to be really careful about one’s words. On the one hand, the founder needs real help to fix stuff; on the other hand they are pretty fragile. Maybe they didn’t raise enough in their last round and so had a hard time hitting ‘ideal’ milestones for the current round and discussions aren’t going so great, and the runway is getting short. Their confidence has taken a real hit. They know it, you know it. Being harsh isn’t needed. They need to be inspired to push through.

This is what is called a ‘sideways deal’ in VC terms and sucks up 80% of investors’ time. You need to kick ass or it is game over, but also, you need to be aware that the founders confidence is super-low and you need a lot of carrot and stick to build them up. If you give negative feedback, you need to follow-up with something inspirational to give them a pick me up when implementing a small positive change.

This is the most difficult place to give advice to founders as you need to balance saving the business and giving the founder the confidence to save it themselves.

Honestly, where the founder is good, but feeling low, this is where my heart breaks the most. It’s also the hardest place to give the ‘right’ feedback, and I’m pretty sure I mess it up a lot.

Inexperienced founder building a business poorly

In stark comparison to the category above, I tend to give critical feedback with near wild abandon. Why? Time opportunity cost.

Basically, you find some nice enough founders, you want to help, and they want help, but they are fundamentally wasting their own time. It is just not working and won’t but (In Asia) they likely don’t have anyone with the balls to tell them. Most people will smile and say ‘keep up the good work,’ which helps no one.

I can tell within, well, I could say 20 seconds, but let’s say 2 minutes, that what they are doing is not working and won’t. Key for me here is they are actually building a business, meaning they have executed not just talked, even if it is not good. I respect that. They are real founders, just not experienced.

I love founders in this category, well the ones that take critical feedback well. A startup in Malaysia comes to mind. I took their whole model to shreds a few months ago, I gave them a plan to execute and met them again (as they chased me) and they genuinely listened and executed to the point I would genuinely give them money now (Almost). I love this kind of founders. They are genuinely trying, have nothing to lose, and find the confidence to do better.

On the other hand, you find founders in the same bucket that don’t take feedback well. They annoy me a lot. They are going nowhere.

Inexperienced founder with an idea and is worth helping

This is a bit of a weird category for most, but my favorite place. Sometimes you find founders that are simply going to achieve something, but just need help to mess up less. Heaven!

The great ones will take direction and achieve even more than you expected. I have set a few startups with guys in this category and mentor a multiple more. They execute, they listen and learn and achieve. Once you build a rapport where they know you care about them, you can shout as much as you want so they achieve more and they triple productivity gladly. Chucking them a bone every now when they do a good job is critical to keep them going 110%.

Inexperienced founder with an idea and is a waste of time

There is a space reserved in hell for ‘founders’ in this category. You find the most ignorant, entitled “founders” ever. I use inverted commas for a reason.

Entrepreneurship, like acting, is a funny category of business. Why? They are the only professions where you can be unemployed and still claim to be something. “I’m an actor”. “What are you in?” “I’m between jobs…”

To be clear, if you have an idea, not executed, not got someone to quit their job to join you, and not even have a website, you are not a founder. You are unemployed. You are a waste of time if you expect more than what you have done yourself.

I don’t really understand why, but there is this pervasive notion in the VC world of espousing being ‘founder friendly’ and ‘giving back.’ The guys who made it made it for themselves, even if they did get some people helping them out a bit. The altruistic notions are not what I am contesting here. What I am is that I have the sense this has transposed into the minds of ‘founders’ that they are somehow ‘entitled’ to something. Investors aren’t free consultants, they exist to make money and you aren’t paying for time.

These are the people that give every other ‘founder’ a bad name. They have the most ignorant sense of entitlement you would be shocked. I have no time at all for these unemployed ‘founders’ and don’t frankly care if I get called an as for saying it in public.

Altruistic aspersions should only be reserved for the hustlers, the dreamers, the guys n’ gals out there bleeding from their heart to do something better, different and more meaningful.

Talent vs no talent time allocation

Steve Jobs was criticized for spending time on the top performing staff instead of non-performing staff. He said the top guys do 3x results so why bother?

I agree.

Hate me all you want, but I am solely interested in results and building more success stories. If you are incapable of achieving anything independently you aren’t a founder, you are an employee at best, and even then I don’t want you on the team.

I like to find top talent who haven’t achieved much yet and invest in them with no expectation of returns. I am happy to wait for years. Typically, I find they come to me for help when they are ready. I want to build successful companies and only great people do this.

Depending on the level of experience, stage of business and degree of success I give feedback in different ways. The extent to which I will spend my time with no expectation of reward varies dramatically. The truth is everyone needs help and someone to get feedback from. How you provide critical feedback also needs to be calibrated. So when you are crapping your pants and getting feedback, understand I’m thinking about how to do it and why.

Take away for you on critical feedback?

Shut up more. Two ears, one mouth. Listen. If you get good, honest, critical feedback, be a filter, not a sponge. The more you listen AND act on that the more people are willing to help you.

If I give you critical feedback (which isn’t dumb) and the next time we talk you have implemented and more, I am encouraged to help you, as is any person you want advice from.

If you have an ego, don’t listen, don’t ship and test, no one will ever have an emotional commitment to helping you. They get off on seeing you grow and that THEY helped YOU. Appeal to their ego, not yours.

Most people will never give you direct, honest feedback. If you find them, cultivate them. You will be surprised how much you can engender when you listen, act and thank.