Last year I began writing small angel checks in early stage startups and advising founders on product design. I probably know 1% of what there is to know about either of these topics. But: in the same year since I've started investing and advising, I've had dozens of conversations with other designers who have also taken their first step down this path, or wanted to start but weren't sure how.
While it's too early to say if I'm particularly good at any of this, it seems worthwhile to share what I've learned so far to help anyone who is just a step behind me. In the future, this will be a nice artifact to calibrate against. Grain of salt, etc.
Please shoot me a direct message on Twitter or fill out the feedback form below if anything here is incorrect or needs clarification.
The term "design advising" is too nebulous, and I've had to explain myself to many early stage founders who were unsure about what I would bring to the table. My flavor of design advising is: providing tactical product and design feedback through structured critique, helping with hiring (not recruiting), and making strategic introductions.
When to start advising
Before we dive in, it's good to consider ahead of time why advising is interesting at all in the first place. For me, it's about scratching an itch that I can't scratch anywhere else in my life. It's about working at the super early stage on undesigned solutions with people who dared to go all-in on some vision in their head. I find it inspiring, and it keeps me grounded in my day job.
Ways to be helpful
Finding startups and founders
The easiest and most obvious way to get started as a design advisor is to have inbound requests from founders. This only happens when you have the skills and reputation in the industry that lead people to seek out your advice. Or, of course, it's very common to collaborate with former colleagues as they leave a job to start something new. Leaning on an existing network of trust and goodwill is probably the best way to dip your toes, learn, and figure out if design advising feels good to you.
The second easiest way is to advertise that you are an advisor and investor. Put it in your Twitter bio, on your website, or write a blog post about it. I've seen other advisors be successful by putting up a mini pitch about how they like to work with startups (see @mxstbr's page on angel investing) or get listed on public directories of angels and advisors (see devtools-angels and Design Angels).
One thing I didn't realize early on in my time as an advisor was that I should also be going outbound and cold messaging founders. This quickly becomes a sales-y type of interaction where I'm trying to prove to someone I haven't met that my advice is worth their time and equity. Outbound is undoubtedly harder without a track record or public reputation for being useful to startup founders, but I keep a thread running in the back of my head when I see an exciting product or company launch: I wonder if I could convince that founder to let me help out?
When I first started meeting founders, I wanted to help with anything and everything. Unfortunately, that's neither realistic or possible. For example, I have many responsibilities at my day job that must come first. Over time, I have honed in my pitch to be explicit about how I can and can't help. See the notes above about ways to be helpful, and find your own unique combination of value to bring to the table.
There are many good ways to figure out the right working relationship with a founder, but my general principle is to keep it as simple as possible. My contract typically looks like this:
I like to set up a working relationship in 3, 6, or 12 month chunks, meeting weekly or every other week.
In some cases, founders don't actually need a rigorous schedule of feedback or critique time, and what they really want is my phone number on-hand for any design-related situation they may come across in the future. In these cases, it can make sense to hand-wave that I've written an imaginary angel check into their company, convert that into shares, and then collaborate as needed.
I'm sure there are many other ways to set up a working agreement with founders, but my guiding rule is to be as founder-friendly as possible. I've been on the other side of the cap table where I know how much work it can be to manage expectations and relationships with lots of equity holders. I want to be the advisor that is low stress + high value.
Disclaimer: angel investing is very popular right now. This means there are competitive pressures, FOMO, and other highly-variable factors at play in the market. While angel investing should become more accessible to more people over time, it is wildly risky and most people would be much better off getting rich slowly.
I'm too early to know if I'm good at angel investing or not. But, I have learned some things! Here's the short list:
Advising and investing has been a lot of fun for me, but I'm still learning. If you're reading this and you're further ahead, I'd love to hear your tips or corrections about anything I've written above.
If you're a startup founder or early stage designer and want to chat about working together, please reach out!
A small favor
Was anything I wrote confusing, outdated, or incorrect? Please let me know! Just write a few words below and I’ll be sure to amend this post with your suggestions.