Investing
What do you invest in?
We back world-class technical founders building at frontiers of the software-addressable economy.
What are “frontiers of the software-addressable economy”?
Advances in AI have created dramatic new capabilities for software. Today, startups can solve customer problems with software in ways that weren’t possible a few years ago. This expands the addressable market for software startups into areas of the economy that were previously the domain of manual, inefficient, analog processes.
How early do you invest?
As early as inception. We are often the first investors in a company, and are happy to help you incorporate.
Do you invest in solo founders?
Yes. Solo founders can leverage AI to build with the speed of larger teams. We still prefer founding teams of 2–3, but we have and do invest in solo founders.
What is your check size and ownership target?
In Character Labs, we invest $150k for 5% ownership. For Core Investments, we invest up to $2 million for 6–10% ownership.
Will you join my board?
We occasionally take board seats for Core Investments, but it is not a requirement.
Will you invest in my next round?
For companies in Character Labs, yes. We guarantee pro rata participation in your next round. With Core Investments, we often find that allocations are more competitive in the next round (typically a Series A), so we evaluate these situations one at a time.
What’s your policy on competitive portfolio companies?
We do not make Core Investments in competive companies. In Character Labs, we avoid conflicts, but given the early stage of our investments, sometimes this is unavoidable (especially following a pivot).
Do you require a warm intro?
No. You can get in touch by filling out this form. It should only take five minutes and is the best way to get your company into our pipeline.
After you invest, what support can you provide?
We run sprints (including our Design Sprint and Foundation Sprint methods) to help you find and expand product-market fit. We can also help with marketing, fundraising, big decisions, governance, and general advice. We’ll do our best to help you hire, but it’s not something we focus on.
Do you actually have time to work with me?
Yes. We designed our team, systems, and schedules to spend big blocks of time working with founders. It’s our favorite thing to do!
What’s the best way to get in touch?
Just fill out this form. You can also apply specifically for Character Labs or Character Foundations.
Our Sprint Methods
What is the Design Sprint?
Our five-day process for testing ideas by rapidly prototyping and testing with real customers. You can read more here.
Did you really create the Design Sprint?
Yes! Jake created the Design Sprint at Google in 2010. Fun fact: The very first Design Sprint (it didn’t have that name yet) was during the founding of Google Meet (also didn’t have that name yet).
What is the Foundation Sprint?
Our two-day process for starting big projects. You can read more here.
Why did you create the Foundation Sprint?
After founding Character Capital, we started working almost exclusively with founders at pre-seed and seed stage. Those teams had different questions and challenges than the later-stage teams we often worked with at GV. We decided to create a new sprint method that was tailor-made for them.
Have you created any other sprint methods?
Yes! Over the years we have created the Name Sprint, the Pitch Sprint, and sub-sprint techniques like Note and Vote and Magic Lenses. You can read about some of those on this site — and there are others we haven’t shared outside our portfolio.
Will you create more sprint methods in the future?
Undoubtedly! The best way to find out about these is to subscribe to our lightweight weekly newsletter.
Why should I use sprints to build my startup?
- To figure out what to build and how to market it — this is especially important now, because AI has dramatically reduced the cost of building
- To learn from customers in the most productive and efficient way possible
- To capture unique insights that will help you stand out in the market
- To make principled decisions with your team
- To have more fun :)
Did you really work with Slack, Flatiron Health, and all those other companies?
Yes! From 2011 to 2017, Jake and JZ were operating partners at Google Ventures, and our entire job was to help portfolio companies with their product and marketing. During that time, we ran sprints with more than 100 portfolio companies. Many of these stories are in our book Sprint.
Our Sales Pitch
Do founders really ask you for a sales pitch?
Not often. But hey, at least we’re being up front about it.
Okay, fine: Why should I work with you?
- While most investors stop at giving advice and making introductions, we will use our sprint methods and our experience to help you find what matters most: Clarity about what to do, and validation when it’s working.
- We pride ourselves on being the best possible partner to early-stage technical founders, and if you ask around, we’re confident you’ll hear the same.
- We care about so much about integrity that we named our firm Character. When you raise money from an investor, you’re partnering for years — maybe a decade or more. We take this seriously.
Have you invested in any successful companies?
Yeah. You can check out our portfolio above.
Are you up to speed on AI?
More than most, less than some. Fortunately, we find this stuff really interesting, so it doesn’t feel like work to read and play and debate what’s happening in AI and how it will affect the world. We also worked on some of the earliest mainstream applications of AI (at Google and YouTube) and have invested in AI pioneers like Veda from AlphaGo, Jim from Google datacenters, and Jonny from the famous mammogram paper.
Will other founders vouch for you?
Certainly. We can connect you to references, and you’re welcome to reach out to founders directly.
Vulnerable Questions
Is this a good startup idea?
We can give you our opinion, but the best way to find out is to build something that you can put in front of real customers. Action produces information.
Can I really trust what customers tell me?
In our experience with 300+ startups, yes, you can — but only if you follow these rules:
- Focus on customers who match your target profile (i.e. don't ask your mom)
- Show customers real products or marketing (or realistic fakes)
- Show customers multiple options (including competitors) and let them “shop” out loud
- Watch what they do — how they react, when they lean in, etc
- Ask about what they have done and are doing — don’t ask what they would do
- Augment what they say with data about what they are really doing
Do I have product-market fit?
The most popular definitions of product-market fit (“you’ll know it when you feel it” and “when customers are ripping the product from your hands”) aren't very helpful. Our definition is simple: Product-market fit is when you can consistently and sustainably find, convert, service, and retain customers in your target profile. We like this version because it gives you a four-part template for what you need to figure out.
Should I keep going or pivot?
This is one of the hardest questions in startups. Two things are true and seemingly in conflict: You should pivot as soon as possible, because things that don’t show early sparks rarely start working. And also, it often takes longer than you’d like for the sparks to turn into flames. So rushing the decision can be just as bad as waiting.
Unfortunately, we can’t answer this question in the FAQ section of a website, but we can tell you this: The best way to decide is by taking action, gathering information, and looking at the decision from multiple perspectives, and our sprint methods are really helpful for doing that.
