The Inquisitive VC: Mario Gabriele — Charge Ventures
Mario Gabriele is a Venture Partner at Charge Ventures, and the creator of The Generalist, a media company and community covering tech from idea to IPO.
We talk about Mario going full time into writing, how to ask good questions, the creator economy, and Charge Ventures.
NA: Thanks for joining me, Mario. You stepped away from venture investing full time to go full time on The Generalist. Could you talk through why you made that decision, how difficult it was to get to that decision and then execute on it?
MG: It was definitely something that took a lot of months to untangle. Partially, I think because I really enjoyed working with my coworkers at Charge, we’re a really small team, but I think great people and very smart folks that I was enjoying learning from.
I think the fund has an exciting trajectory and has a real opportunity to own a part of the New York pre-seed market and part of the US pre-seed market, which I think is an exciting space, and has a pretty differentiated approach.
All those things made it hard to take a little bit of a step back. The reasons that I wanted to do it were more personal than anything else. I just really love to write and always wanted to have that be a significant part of my life, either professionally or personally. As I started to see The Generalist grow bit by bit and the opportunity to materialize in my mind a little bit more clearly, it felt like I should try and give it a shot.
NA: I think it’s great that you’re doing something that you truly enjoy. It’s a great motivation for others as well, especially when you’re building that whole process out in public on Twitter. I’ve seen a few of the topics that you go through on The Generalist, you have sections where you interview guests. How do you go about formulating questions to extract the most value from your guests?
MG: Such a good question. I am definitely still thinking through it all the time. A few things that I found useful:
One is focusing the scope of the interview one way or another. Because I have The Miss and The Prologue, that gives me a lens in which to answer questions where The Miss is focused on an investor’s anti-portfolio. I know I really want to get the meat of that story as much as possible, versus The Prologue where I’m mostly interested in figuring out the more operating background of different people. I would say, that is one thing that helps a great deal.
Two, I am personally always interested in hearing more of the personal side from folks, I think, we end up hearing a lot about people’s work history, so, as much as possible, I like to hear about their childhoods, about their sort of early heroes, about the books that maybe they think found impactful, the things that round them out as a person.
The third thing is, I have been talking to people in advance, talking to other folks that know them well or even putting a question out on social media and saying, “Hey, I’m gonna interview this person, what do you think I should ask?” That’s been another way to sort of triangulate different ideas, but above all, it hopefully ends up being a little bit of a conversation and through that, maybe you don’t get every question on your list, but you’ve got something else that you couldn’t have predicted.
NA: Definitely a great way to go about it. As you mentioned, you have The Miss, you have The Prologue, and you have quite a few others. I want to understand how you think about what you want to write about and then what’s that process from the initial thought to actually having that final copy ready to get published?
MG: The one that’s really stressful to write is the Sunday email because that’s the one where it’s all my own analysis, whereas, the S-1 Club ultimately, we have something that we are working from and same for the others, like the interviews are based on the source text.
The process for that one is, I start getting stressed around Tuesday, and then for the next couple days, I sort of futz around online, thinking about half ideas that I think might be something and then Thursday, usually I’ll start writing it out in in a little bit of detail and finish it, or finish a draft on Friday.
Then Saturday, I almost inevitably end up rewriting it pretty heavily one way or another because I either like to show it to my girlfriend who’s a great editor and very helpful, or I look at it again, myself, and I think I haven’t really been as clear as I wanted to. It’s a little bit of a longer process than I would like, but hopefully, each time you get a little bit better, and ultimately, it’s a fun, enjoyable pain.
NA: This is with your investor hat on and also actually being part of the Creator economy. There’s been a lot of talk about it over the past few years. COVID’s definitely accelerated that whole process of people taking starting things up. What are your thoughts on the creator economy?
MG: I think it’s a really interesting movement. I think the biggest change has been almost one of branding more than anything else, we’ve had influencers for a really long time and we’ve had, certainly YouTubers, Instagrammers and streamers for at least the last few years where it’s felt like there was a lot of money in those things.
I think the venture framing of the “Creator Economy” has opened it up in this way that is maybe more graspable for people where we start to think okay, it actually is the solo newsletter analysts or it is like a podcast host. That’s been sort of the biggest change, I think and coupled with that has really been an influx of capital and focus towards it, which is, there are some creator-focused funds emerging, there are plenty of generalist funds that are now starting to talk explicitly about wanting to invest in the creator economy.
I think the result will be a new class of tools, especially on the operational administrative side. We have plenty of platforms for creators and things like that but when it comes to actually try to run yourself as a business, there’s not a lot there at the moment. I think in the same way that there have been plenty of big winners in taking what used to be a Fortune 500 function or process and serving startups with a similar solution, I think you’ll see the same thing for creators.
NA: So you definitely reckon there is some sort of market there instead of them using tools for designed for maybe small, medium businesses?
MG: Yeah, I think there’ll be some cases where the existing tools work totally well, and maybe venture is blowing it out of proportion. But there’s usually some interesting functionality you can unlock when you profile your customer in a totally new way. Whether that’s going to be analytics for your audience, or whether that’s going to be incorporation or tax servicing or banking or growth, all of those are such core functions now for startups, but if I, as building The Generalist was like, I should start using Mixpanel, or Heat or any of those things, they’ll be way over my head, and really hard to maintain.
So what would it mean to have, a creator-focused version of that? I think there’s a bunch of different things that can be built. The tricky thing I think will be having enough horizontality where, if you start with newsletter writers, you can eventually scale across to other personas in the creative stack otherwise, maybe it ends up being just a little bit more of a niche tool.
NA: That’s a great outlook. If you were to raise a fund or more relevantly a rolling fund, what would be your investment thesis? What would you invest in?
MG: Oh, man. I mean, I definitely would focus on the early stage just because that’s my bias and where my network is. I guess, opportunistically, maybe I would look at some later stage stuff.
Geographically, I previously did a Master’s in International Development with a focus on tech in emerging markets. So, on a personal level, I would love to see more deals out of Africa, Latin America, and Asia. That’s not something that Charge does at all. We’re North America focused, but if I could get decent deal flow from those places, I think there are huge price arbitrage opportunities as well as it being a real net positive globally.
I think above all, I would probably want to just create a networked fund more than anything else. I’m not sure I really ascribe in a major way to the notion that venture is going to be defined by these anointed pickers who can figure out what the best company is, and super early and just make sure they’re in every deal.
I think venture sort of sprawls outwards and gets more competitive unless you’re at a top tier fund, it’s just going to be so difficult without having some sort of distributed approach. I guess it would be less about specific sectors or geographies as much as it would be about, a specific structure.
NA: That’s a really interesting answer. For someone who might be pursuing taking up writing, what would be a piece of advice that you would give them?
MG: I guess it would depend on what sort of writing they wanted to do. If they’re mostly interested in tech and venture, I think that the only real advice I have is, just keep at it and be consistent. I think, putting yourself on some sort of forcing function of the day you publish or the frequency with which you publish just puts you in the position to benefit from the compounding growth of self-improvement.
I personally most enjoy writing fiction, which is not something that I do a lot publicly. But obviously, we have a little bit different advice in that scenario, so, I guess it depends.
NA: What’s your vision for The Generalist? Where do you hope for it to be saying the next five years?
MG: Man, if it’s going strong in five years, then something went really well. That would be amazing. I’m very hopeful that that will be true. I think that the goal, for now, is to build the most thoughtful, transparent tech community I can. To do that as a solo creator, but leveraging and benefiting from an audience that is engaged in making it a better and better community themselves. That’s the hope, if I can do that, I will feel very good about it.
NA: Are you able to talk about, what’s the last publicly announced investment you made with them and why’d you make it?
MG: The two last ones that we did were Stream and Bedrock. Bedrock is very deep tech, fascinating company. They’re basically trying to map subsea and so they are taking almost like an autonomy-based approach to do that. A really talented technical team, kind of a moonshot style idea.
Stream is very relevant to the pandemic in general. These guys started the company at the start of the coronavirus outbreak, basically a way for people to monetize video streams. So if I wanted to host an event I could spin up a page very easily and pay gate it with Stream and accept RSVPs. So they’ve been growing super fast and are obviously writing up a lot of market timing based trends.
NA: Those two are quite different, but very interesting companies. I saw on the Charge website, The Collective. Could you talk a little bit about The Collective and why Charge has this kind of program running alongside these angel investors?
MG: Yeah, I think that the vision is really, to the earlier point, one of decentralization to a certain extent. I think it’s clear that there are so many more good deals than any single person or single team could really be aware of and accessing those deals, both sourcing them and winning them is more efficient at the edges to a certain extent.
By having a network of really smart founders, angels, VP’s of product and engineering at different companies that are interested in angel investing, it sort of serves two purposes. One, it gives those people the chance to invest in companies with a little bit less overhead, because we carve out allocations for them to invest in our companies at a later stage when we’re able to.
On the second side, it sort of solves some problems for Charge, which is improved sourcing, it improves the ability to win deals and it also offers networked portfolio support. If one of our companies needs to think through a marketing strategy, in The Collective there would be people who have run that function for years at bigger companies or have been through that challenge as a founder at their own company.
The last decade of venture has really, in some ways been defined by the Andreessen Horowitz portfolio model of just having a massive staff of people to provide different services. It’s really hard to do that as an insurgent fund. This is sort of a capital-efficient way to drive towards the same outcome.
NA: Yeah, I definitely see the value in that. It is a really interesting model. That’s everything I wanted to cover Mario. Once again thanks for joining me!
MG: Yeah. Well, this was super fun, thanks for having me.
