I'm thrilled to finally release today's angel investing with Amanda Robson, or as everyone calls her, Robby.
She is the ultimate go getter, raised in Canada and landing in San Francisco in her early 20s to follow her passion for tech. She carved out her own path in VC with zero contacts and working crazy hours to build her career. That was back then though. Now?
Now she's the youngest ever partner at Cowboy Ventures, which was co-founded by none other than Aileen Lee. The woman who coined the ultimate title to bestow on a startup- "unicorn".
Amanda led a US$3.2-million investment round in a securities-software company called Drata, now worth US$1 billion. She's also the founder of the incredible Modern Angels group, a community of over 250 female and non-binary angel investors who support and learn from each other on their investing journeys. And if that's all not enough, she also made it on the Forbes 30 Under 30 list!
Full interview below!
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I joined Cowboy about four years ago and we do seed and pre-seed stage investing. I cover software infrastructure for us and our team is small.
We all put a lot of effort into branding and talking about the areas that we invest in. There are six of us full time. Myself, Jill, and Aileen who are partners, and then we have two amazing associates and our incredible EA Mae.
I don't angel invest myself because for me it's tricky from a conflict of interest perspective. Instead, I started an angel community and network called Modern Angels, because I wanted to see more female and non-binary operators on cap tables.
The network actually started very organically. I was having dinner with a couple of friends who are amazing operators. One is super senior at Figma, another is an exec at Upstart. I assumed that both of them were doing a lot of angel investing because we show them opportunities at Cowboy and here we always bring in operators to our rounds and make sure it's a really diverse, awesome group in our investments whenever we lead rounds.
I assumed that was the case at most funds, and that because they're both such amazing operators, that they were getting access to more deal flow, and it turned out that wasn't the case.
It felt like there was a bridge that needed to be built between VCs and some of these incredible operators who wanted to angel invest. I took some of their information down around check size and the sectors they like to invest in, and I started sending it to friends in VC as I wanted to give that kind of access to women who might not be directly in my network.
I tweeted it out and I very quickly had 100 women DM me. These are incredible women, like the GM at the Gap, the head of products at Instacart, the CMO at Loom… women who I did not think had an access problem or I just thought were more actively angel investing. This ended up being a way for a lot of them to even just get started in angel investing.
The way it works is it's a community and database.
We have a Slack community where everybody talks about deal flow and asks questions they might have about angel investing. We do a lot of community events and educational events. We've done AMAs with really famous angel investors like Elad Gil, and we did a conference last year where we had a bunch of angels meeting each other and learning together. At the conference, VCs talked about their experience (with angels) and also some founders spoke about why they like to work with angels.
In addition to that, we have this database, which is now in an Airtable, which has all of the womens’ information about where they like to invest, their check size, and their angel investing experience. All the things that VCs or founders would need to see in order to figure out who would be a good fit for the round.
It's about 50% word of mouth and then 50% through socials. I don't know if you call it advertisement, but we have a Twitter page and an Instagram page. I tweet about it myself too.
A lot of women and non-binary angel investors hear about it through that and will DM me. There's an onboarding form through the website, but I'd say it's a combination of word of mouth as the community grows and social media.
I think that investments done in the next couple of years are going to be really high potential. It's not just because valuations across the border are down, but also the quality of ideas are going to go up for what gets funded. I just invest in enterprise so that's really the perspective I'm coming from.
When you think about it, budgets are being cut. There are headlines about layoffs almost every day. Because budgets are more constrained, what ends up getting new budget are tools that really have strong ROI.
It's not just like a 10% or 15% better productivity improvement, these new tools really have to show significant ROI. The bar for what is going to get allocated budget is really high. Tools built in the next couple of years that are actually able to sell effectively are going to be really high quality and have a ton of potential.
I think the quality of ideas of what's going to get funded is going to go up and we’re already seeing it go up, but at the same time, it's a tougher environment in general to operate in. You just get grittier founders that are willing to take the risk at this point. I think there are a bunch of reasons why this is a really good time to invest, but from my perspective, it's really about the quality of ideas (and founders) that are going to come out of this period.
If you look at just the amount of capital that's been raised over the last couple of years, there are a lot of investors and VC dollars out there. So, yes, I think it's still going to be competitive, but I also think that a lot of funds put money into companies that maybe weren't super efficient.
There's a good amount of cleanup that's being done, especially at later stages where you have companies that are valued at a billion or a billion and a half and they still haven't truly hit product-market fit. That's a tough situation to be in.
Cowboy is a seed and pre-seed-focused fund, so we're very stage focused and then we have a few areas that we really specialize in. I (focus on) software infrastructure and that covers developer tools, data infrastructure tools, analytics tools, and security. My partner Jill is based in York and does fintech investing for us. And Aileen, who's our third investor (and founder of Cowboy) does a lot of application layer SaaS, but she also does healthcare and consumer.
She's probably the most broad among us, but she's been investing for a very long time and is a savant when it comes to seed-stage investing. She's definitely seen it all.
Yes, she did. She is an amazing marketer in addition to being an amazing VC. I think in the original “unicorn” post she did, she captured a sentiment that really resonated with people. It's interesting because at Cowboy, we spent a lot of time with our companies on positioning, messaging, and storytelling, and you can really see how Aileen is exceptional at all those things.
My journey was not directly into VC. I see and have friends who came into VC because their families were in VC or they grew up in the Bay Area and they were just always exposed to it. I was kind of more of an outsider.
I went to school in Canada, and when I was in undergrad, I didn't really know much about venture capital or what it was. Honestly, for me, it was really just step-function career-wise. When I was in Toronto, I started by doing internships in banking and realized that if I stayed in Toronto, I would only be working with natural resource companies.
Now, there's a pretty big tech scene in Toronto, but there really wasn't back then. You'd be working with metals and mining companies in investment banking, or paper companies, and I thought tech companies were much more interesting.
I cold-called my way to an investment bank for post-graduation work in San Francisco. While I was doing that, I was just working with founders helping them figure out how to actually sell themselves and how to position themselves to potential buyers.
I loved working with founders, but it's a very moment-in-time thing when you're working with them in banking because you're really just there to perform a transaction. I wanted to work with founders for a longer period of time.
I got recruited to Norwest, the first fund I worked at, because I could do a bunch of different types of investing there. It was everything from Seed stage to Series B and up to Series E. When I was there, everything I loved and was bringing in was Seed or early Series A. For me, it was really like seeing what I liked and just kind of taking different data points from what my role was at the time to figure out where to go next.
The reason I loved Pre-Seed, Seed, and early Series A was because it's the most people-oriented type of investing that you can do. There really isn't much data. You might have a product, but you can't just kind of look at numbers and understand whether or not a company is a leader in the space.
I’m an extrovert and love people, and love studying people. For me, it was just the type of investing that was most interesting, and I really wanted to become an expert in it. After doing early to late stage investing at Norwest for a number of years, I moved to Cowboy to just do Seed stage full time.
No, definitely not. I think it's maybe more helpful for folks because I think sometimes if you're an undergrad or you haven't been exposed to a role, but it just seems like what you should be doing before you actually know what it involves, you'll kind of commit yourself to that path.
Sometimes it's better to kind of go with what feels right and go with what you turn out to be fairly good at. That's really been helpful because I never felt pressured to do a certain path because I didn’t have this preconceived notion of what I should be doing.
It was really what I liked doing and just kept leaning into that. Now, like at Cowboy, I feel like just the way that our team works and the way that I've tried to build my brand, the way I work with my companies, and the type of companies I invest in, it all just feels very authentic and not like a forced thing.
One of the frameworks I like to use is we are only investing in founders where they should be able to be successful without us, but we should hopefully help them get there faster, especially at the early stages, because we really just focus on getting companies to product-market fit and ready to scale.
The first thing we do when we invest in a company is we have a kickoff meeting to make sure we are fully aligned on where we want to go, like big dreaming three years from now where we're wildly successful. What do we need to do in the next year to set ourselves up for that?
We have a lot of these kinds of conversations when we're looking at a company to invest in. Then there is a post-investment, longer strategy session where we really dig into those questions. From there, we have very frequent communication.
We're not just doing a monthly check in and seeing what's going on. A lot of times, especially if something's going on around hiring or their early product launch, it could be a daily thing where we're working with our founders because we need to be really in sync with what's going on, like a sounding board on everything from hiring to products to launch strategy, to positioning to PR to go to market strategy. We help on a bunch of different axes.
I think the best way to describe how we work with companies is we are like the pit crew for them, so they're really driving the car, but we're helping them go a lot faster.
One of the biggest ones are founders that are looking for a problem because they're super smart individuals, but there's no real reason why they are best suited to go after a particular problem space.
It doesn't always mean that they have to have worked in that space before. That happens a lot where you have a security engineer who saw problems in their prior roles, so they're building a tool that they wish they had in one of their prior roles, but that's not always the case.
We have founders in our portfolio who were kind of outsiders but became experts in their space and then were wildly successful building products there. A good example is Drata. The founders came from the edtech space. Before Drata, they had built a company called Portfolium, and they had been exposed to compliance products there and really saw the need for something better.
They weren't your most natural fit as far as security or compliance background founders, but they did a bunch of research and pre-work that led them to become experts.
One of the biggest things that we also look for in founders is that we back people that are what we call “learning animals”. Folks that we think can just pick things up and learn really quickly. The reason that's so important is that at the earliest stage, you're doing everything from sales, product engineering, customer success, ops, and all of that in the founding team.
You need to be able to cover a bunch of areas and, especially for first time founders, they've never done that before. They need to be able to cover off all those functions. They also need to scale themselves from being the scrappy get to product-market fit founders, to them being the founders who can hire really amazing execs and scale out teams, and then be the founders that can scale out that team to eventually take them public.
These are all very different skill sets in a way. We're looking for folks who are learners. You can actually tell a lot about that in a diligence process because we're very iterative and work with founders very similarly in diligence processes to when we invest. We ask a lot of questions, we keep them informed on what's going on in our diligence, and what the open areas we're digging into are
It’s funny because of the stage that we're investing in, it's not as important as the quality of thinking that goes behind the idea. I will say that the best pitch decks in general tell the story, and they tell a story on how that company is going to become a really important generational company.
I think sometimes founders can get into data dump mode where they're like, “okay, we need a team slide, we need a product slide, we need a market size slide”. They just dump all this data in, which doesn't tell you a story, it doesn't tell you, okay, here's where we're ultimately trying to go. Here's what we're the best team set up to do this. Here's our first initial edge.
It's not just about the deck for us, we're backing people who we really think are visionaries and have this view of where the world is going to be and how they are a super important part of that world.
They can also execute in the near term and know what the needle-moving things are to do in the next three months, six months, or year, to set themselves up for that. They're really good at that long-term, short-term thinking.
A pitch deck should be a representation of their thinking. If they are just dumping data into a deck to try and check boxes, then it does raise a question of whether you’re just going through the motions of what you think you need to do as a founder versus you being really intentional about how you're setting yourself up to really go after something massive.
