Basically, it became apparent after doing that that, even though all our partners wanted to continue with Matter, not enough of them honestly were in the financial position to do that. I spent the last two years going from “it looks really good for us” to a waiting game to “oh, maybe this current model doesn’t work.” On one hand, I think what we did was we created a model that was actually perfect for the industry and what the industry needs. I continue to believe in our mission. The industry needs a space where innovation can happen — both on the entrepreneurial side and in a way where we can inject it into media institutions that matter.

We created this pretty creative unique business model to make that happen in a very risky space. Early-stage media is very risky. VCs aren’t clamoring to get into this space. But it’s very necessary. There are huge problems to be solved in this space and some need to be solved from the outside and some from the inside.

So the model we had developed was: We can make early-stage risky bets by investing money from strategic media companies and we can reduce the risk of those investments by providing services to those media companies that they would probably be paying a lot more for but they didn’t have to pay for them because it was the investment. It takes the risk out of the equation.

I still believe in that model. I wish and hope Matter could still exist based on that model. But the flipside of that model is that Matter is not diversified. It’s overly concentrated in depending on media companies for its future. The macro environment for media companies, especially journalism companies, is worse not better than when we started. It’s kind of a Catch-22 there.

The world has changed dramatically in the last seven years — what should I pour myself into next? I want to be clear, it could be Matter again. But I’m very specifically separating myself out from that to give myself the widest options.

I’m proud of the team we’d built. I’m proud we were able to figure out how to replicate and scale the culture; it’s not something that’s easy to do and we were able to do that in our expansion to New York. I’m proud that we were able to get in the right direction in terms of diversity and inclusion for our portfolio. In our second fund, 50 percent of our CEO founders — not just the founders but the CEOs — were women and 40 percent were entrepreneurs of color. I wish that were even better, but I think in an industry where that’s been pretty horrible both on the VC side and in terms of media, I think the seeds we planted there are going to be really important for future leaders within this industry.

I’m proud of a number of things, but at the end of the day what we created were experiences that literally changed how some founders and some leaders approached their lives and their work and are able to achieve their goals better and able to be leaders that then affect others.

Obviously, I wish I had cracked a sustainable business model for Matter. I’m not sure exactly how to do that because I’m pretty proud of the creative business model we came up, with but obviously looking back it was overly concentrated within media journalism companies. Matter’s success depended on their financial success, and ultimately the top-down trends in the industry are really hard. We had set ourselves up to be vulnerable to things that were out of our control. We could have maybe had a more resilient business model behind what we did. But if we did there would have been a lot of tradeoffs — we wouldn’t have been as specialized and impactful in the media and journalism space.

When we started Matter, I decided that we needed to take a venture capital approach to this. I still think that was the right starting point for Matter, because there really wasn’t anything offered like it in the marketplace when we started. However, I wish that we could have figured out a model that was a mix of companies that are on the venture capital journey — I feel like there’s an opportunity in the middle, in between nonprofits and venture capital. I think especially this space is one where I call it, to use a baseball analogy, instead of looking for only grand slams, what are the good doubles? We made a lot of investments over time that we knew were never going to be grand slams, but that we thought could be good sustainable, viable doubles that were actually solving a really important problem in this space. I’m glad we made those bets. What I wish is that I had figured out a way to have more of a supportive ecosystem from an investment perspective for those doubles.

Now, I think part of that is issues around the label of what media actually means. At Matter, we’ve always intentionally been very broad about that — we see it as the connective tissue of society — but in a lot of VCs’ minds, media is content and something that isn’t scalable.

The other thing you see in this sort of environment is that the power of network effects are so strong, as well as backed by data, that the marketplace is almost anti-competitive when it comes to the big tech companies right now. It’s so hard to break into that space. Obviously, there are huge cracks, and trust is a big issue, and there will be big opportunities in this space. But there’s not enough of an ecosystem betting on that at the moment because of the power of the big players.

The second part of that is, if so, what would the model be for an investor in zebra companies? I’m especially interested in the question of: Can an investor in zebra companies still make risky early-stage bets? Obviously, that’s the stage I play in and I think it’s tremendously important that there be capital out there that is making early-stage bets on entrepreneurs. There’s obviously a ton of capital out there for people who have already proven out their business models, but the real value-add is who will be there to bet on companies early.

In the venture capital model, the way that works is you’re able to make lots of risky early-stage bets because hopefully you end up having some hits come out of there that can make up for the inevitable losses coming from failed bets. What I don’t completely understand yet in the zebra movement is: If we’re saying that you’re taking the grand slams out of the portfolio, does that mean that the risk-reward balance changes? And does that mean you can’t make earlier-stage bets? That’s something I wouldn’t like if that were the outcome. I don’t think that’s what they’re going for at all, but I think the next stage here is a real model. I do know there’s a lot of experimentation being done in the different types of structures that you can do to invest in the zebra type company.

And the word “empowered” — it’s just too broad. So we changed our focus to “inclusive” because inclusivity is such a huge problem and opportunity within media and within venture capital. We wanted to really sharpen our focus on that. Post-2016, you look at what’s happening, the diversity and inclusion standards right now within newsrooms, and it’s worse than it was in the 1970s. You don’t have diverse and inclusive leadership within news, while at the same time you have an administration coming in that can be an existential threat, especially to non-whites and non-males. And so the issue we saw coming was a potentially huge frog-in-the-pot problem within journalism — where journalists and journalism organizations wouldn’t actually react and recognize the extent of these existential issues quickly enough because they didn’t have diverse leaders. We really wanted to put out a call for people working in that space, as well as to back more entrepreneurs of color.

We have a lot of media organizations who still haven’t changed much in the last 20 years. Then we have some who say we need to change and need to come up with the next big thing. I don’t think it’s any of those. The focus needs to be: If you’re going to be long-term sustainable, how do you build an organization with a culture and processes that enable teams to constantly be understanding their audience and adjusting — constantly be experimenting with new technologies, and constantly seeking out new sustainable business models? If you’re a leader of a media organization and that’s not the No. 1 thing you’re thinking about every single day, I don’t think you’re leading your organization to long-term success.

Culture is a fuzzy word. Culture is hard. But ultimately at the end of the day culture is going to be the key competitive and sustainable advantage that’s going to be ultimately what cracks it for a media organization. The hard work needs to be done there. That’s the hard work we were focused on at Matter. It would have been much easier to ignore that side of things. But then why were we doing what we were doing in the first place?