I often get asked by startup founders which numbers/KPIs (Key Performance Indicators) investors care about and what are the numbers that drive investors to invest or not. In this article I will review some of the numbers I look at and give insight into how I evaluate these numbers. This article is intended for seed and pre-seed startup founders, but I hope that round A or even B startup founders will find it useful.

You add more hiring managers, more interviewers. Need to fill more roles. All of a sudden, things start breaking....

On average, I make 100 micro decisions each week. As a CEO, I get requests from every function plus from customers, investors, candidates, etc. And every time, I need to decide how to respond and how much time to allocate. When I described this challenge to my executive coach, Dave Story, he surprised me. I expected him to tell me to say "yes" less often and give me some decision-making frameworks. Instead, he made a small observation...

Startups are hard, that is not a secret. There are many risks that startup founders are aware of — funding running out, clients not paying, employees retention issues are just examples of common known problems. But there are also several hidden problems that founders, and new early stage investors are unaware of (or do not pay attention to) that could very easily kill your startup. These hidden issues are hidden because they do not seem like a problems at first, until it is usually too late to solve them — startup with these issues are walking dead.

Managers: Have you ever wanted to promote somebody but needed to wait a few months until the next "performance cycle"? Lalit Singh and I built 20 teams before we started Vareto, and this used to bother us immensely. So we fixed it.

Founders: what’s your “why”? A common mistake both founders and investors make is not reflecting on the founder’s motivation for starting a company. And I don’t mean the “market why” or “why now” question. I mean the “personal why.” Why are you starting a company, and this company in particular?

Founders: I highly recommend creating a 1-page summary of your business. It's helpful for investors (saves time on FAQs!), but even more importantly, it's helpful for you. It's only when you see the different aspects of your business in one place that you can connect the dots. If your audience is X, then why are your first customers A and B? If you're saying the problem is Y, then why are you building feature C? Achieve clarity, then execute brilliantly. The rest will follow.

As an angel, I frequently help other founders with fundraising. One of the most common rejection reasons they hear is, "It's too early." This is so vague. It's also baffling when it comes from investors that have recently invested in pre-revenue and even pre-product companies. What could be earlier than that? Here's the thing. "Too early" is often just the short version of, "I don't have enough conviction to invest now, but I'd like to stay in touch and invest later if things take off." So why don't investors just say that? Because founders tend to confuse "I don't have conviction" with "you don't believe in me." It feels personal, and investors don't want to burn bridges. Fortunately, this is solvable.

If you’re reading this, the door is already open. Maybe you’ve been at a big tech company a few years and it’s not as exciting as it used to be. Maybe a founder reached out to you about an open role and you can’t get the idea out of your head.

In this article, I share the unique tactics and moats in human-in-the-loop businesses that you can leverage to make the market “tip” in your business’ direction. I gathered these for you by spending the last 3+ years around operators at human-in-the-loop businesses, investing in a few of them, and building one from scratch at Yobs.

There is a clear gap between how AI/ML insiders and outsiders evaluate the sector and what it takes for an AI/ML upstart to win its category. I encourage you to use the framework in these essays when thinking of your own enterprise AI/ML startup and building your product roadmap. This will be a constant work in progress so any feedback is welcome!

An old (but still relevant) article I wrote about developing better product sense and passing PM interviews.