Nathan/ You have this novel approach to fixing things, and combine product experience with financing experience. What do you wish people would know or do or prepare before they contact you? What are the questions you really want to engage with?

Spectra/ I want people to be clear about what’s driving them, regardless of whether they’re an investor or a funder. Why are you doing this work? It doesn’t really matter what’s driving you as much, as long as there is something. I don’t think people spend enough time with themselves because, too often, they’re stumped: “What do you mean what’s driving me?”

I am a mission-driven investor and ecosystem builder. I want to build community. It runs through everything I do. So, knowing what gets people to the table and understanding their motivations are important so I can understand where there’s synergy and if the model that I’m using to evaluate opportunities and make investment decisions actually makes sense.

I was referred to a cybersecurity company the other day and I didn’t understand why we were having a conversation. I took it because it was someone I knew but they clearly hadn’t done any research about me or the fact that I invest in mission-driven businesses and that I don’t really care about cybersecurity. So, I think being clear about who you are, is essential. And, when people spend time being clear about who they are and what drives them, it makes them curious about what drives other people. That’s rule number one.

Nathan/ Why aren’t all investors mission-driven? What needs to change?

Spectra/ You know, that’s complex. It feels like it could be. It really depends on where you come from. I’m from Nigeria and I have friends from there who didn’t grow up with a lot of money and had hard lives. We’ve all had lives with varying degrees of difficulty in various axes. My mother was a philanthropist. She was the first entrepreneur I ever knew. She stayed at home to raise her kids and built her business. And it was seasonal, but she made more money than my dad. I grew up with a mother who was the supplier to Nigeria’s largest gift bags for all holidays and events. And she made a ton of money every year that got us to travel and do all these things.

And my dad was a traditional banker who brought in a modest salary. So, I kind of grew up with these two different figures. My dad was more of a traditionalist, climbing the ladder in finance. And my mom, was a stay-at-home mom but also a philanthropist whose business supported a large ecosystem of merchants where I grew up. Every year, if a deal didn’t come in, I’d hear her say, “Ah, this person was depending on this.” So, I grew up with that. It’s in my DNA. As a result, I’ve never seen business and caring at odds with each other.

There are people who work in the same environment that I do that didn’t grow up with my parents or my context; who see the accumulation of wealth as a way to honor their parents. They’re not mission-driven in the same way that I am but in a different way. I think everybody is on some sort of mission but their missions may just be different.

Nathan/ I can relate to that. I tell people that one of the things I’m most thankful to my parents for is growing up in Silicon Valley—at a special time there. My father was an entrepreneur. In that place, especially at that time, being an entrepreneur wasn’t a myth. It was what the next door neighbors did. It’s what my father did. So when I started my first company, people around me were so concerned: “How are you going pay your rent?” And I replied: “I’m just starting a company. What’s the big deal?” That’s when I realized not everyone grows up that way. It’s not a fundamental part of how they view the world.

Spectra/ I grew up in a developing country where most businesses aren’t having to solve social problems. I mean, that, that’s what is needed. [That’s what’s valued, right? We’re not selling McKinsey, uh, presentations. it’s like infrastructure and stuff. So, yeah.

Nathan/ How would you describe to someone to align their values, their strategies, their goals with their finance and funding strategy, day to day? What does that look like?

Spectra/ For me, it’s breaking everything down into questions and keeping top-of-mind, honestly in my heart, as to what really matters to me and the questions that I should be asking myself. Those questions come naturally, for me. For example, I care about doing good in the world, so when I become an investor, it was imperative to simply ask “What kind of investor am I going be? What does ‘doing good’ in the world mean?” This is combined with the way my brain works: I’ve always been someone who sees opportunity or made connections that are not always obvious to others. I intersect so many things so I see many things and care about things others don’t.

What does it mean to give people money? When I started investing, everything was new to me. I had to learn about cap tables and so much more. I quickly came to the conclusion that the systems and paradigms we use today and inherited from finance haven’t necessarily served the world well and are clearly antithetical to equality. So, if I’m going to play in this space, what does that mean for me? The point I got to—which many people get to—is to invest in people that ordinarily wouldn’t get access to capital because of systemic discrimination. Because even when people are trying to be objective, they’re not taking into consideration who gets it, systemically.

My paradigm is to actually invest in things that are going to make the world better—not just underrepresented or marginalized people, but anyone who is making the world better. That quickly led to the question of: “What are the problems of the world? What are the biggest blockers to prosperity for the most marginalized people?” That’s how I came up with the thesis areas that are guiding me today. These questions beget more questions that beget more questions, and I follow my own North Star of what I want to do in the world. I try not to be afraid when I run into roadblocks or an absence of playbooks to guide me. This is where being a product person is very helpful, because that’s a paradigm for figuring things out. And, you just do. At the end of the day, what are we trying to get done? I’m suspicious of current solutions because if they were working we wouldn’t have these problems.

Nathan/ So what do you ask for from the people and companies that approach you. Do you ask for a thesis? How do you come to understand where their values are and what they’re really trying to accomplish?

Spectra/ Because I’ve been a product leader who worked in tech for about 20 years now, I’m usually approached by early stage founders who are looking for advising on one of a few areas: product, go-to market, product positioning, clarifying value proposition, hiring, etc. I’ve been very loud about exclusively hiring and building teams that are high performing. I ask everyone the same question: “What are you building?” Just that simple question reveals a lot. Some people will start with their origin story. Some people will recount their elevator pitch. But, then I ask “Why are you building it?” which is really the question I’m trying to get to. That tells me if they’re in it because they really want to make a difference in their customer’s lives—if it’s really for others or if it’s just for themselves. That is a very strong signal.

I’ve seen groups who won a competition in school and got some money and now’s their looking for more. And, often, they’re just not awake or have a mission. They aren’t as aligned with their company as the person who’s building one because their dad died when the medication he got was a placebo and was never tested on people of color. I’m likelier to invest in people driving diversity in clinical trials than the person who’s building a cybersecurity company because they won a competition.

Nathan/ You’re not the typical investors—yet. Would you advise a company to like tone it down for traditional investors? Or, is there a way that they can share their values and everything you’re talking about in a way that doesn’t confuse traditional investors? Or, should they just not care about them?

Spectra/ As someone who builds products for a living, I’ve learned that if you try to appeal to everyone, you will appeal to no one. I think it’s the same with investors. The best way to stand out is to be and show up Right, in the full glory of your conviction. Investors are driven by conviction. They’re very emotional people. They like to pretend that they have little spreadsheets and they have like criteria and stuff, but they’re very emotional people. This is a very FOMO (fear of missing out) industry. There’s nothing quite like a founder who believes in what they’re saying. It just unmatched—especially with someone who is listening for cues, like me. You can see it, you can smell it. Otherwise, my question would be if they’re going have the convictions to stay the course. Those are the bets I make. I don’t want to work with people just meandering for the next few years. I think conviction is the coolest, sexiest trait ever, honestly. And want to work with founders who have it, whether they’re mission-driven or not. You don’t want somebody on board for the wrong reasons—especially if they’re writing you a really big check.

The worst thing to do is to try and trick people into thinking they’re aligned when they aren’t. If they aren’t interested in your thesis and direction, that doesn’t mean it isn’t the right path for you, just not for you them. It would be worse to try and convince them to get on board with something that doesn’t meet their thesis or plan. It might be disappointing now but it’s much better later. And, the only way to know that is to show-up as yourself, be clear, and see if you truly are aligned. If they’re saying “no” to investing in you, it still doesn’t mean they disagree with your thesis. It may be that they just don’t feel they can help you with it. You may need seed investment and they may specialize in a different phase. Remember that they may be saying “no” to your thesis but they’re saying “yes” to theirs.

Nathan/ I’m so glad that you blew open this myth that investors are not emotional because oh my God all humans are.

Spectra/ I have never met a more emotional set of people, to be honest.

Nathan/ I always tell students that investors, particularly venture capitalists are the the most risk averse people in the highest risk industry.

Spectra/ Talk about constantly being in “flight” mode, right? And with trauma-informed contexts they don’t acknowledge the biochemically emotional state in their bodies. So, no, there’s no truly rational conversation. You can only show-up as your full self.

Nathan/ The way interpret what you shared is: “Whose train are you on? Are you on your own train or theirs? And if they come to ride with you on your train, are they coming to help?” Otherwise, you’ve somehow, weirdly getting on their train with your product and they’re driving?

Spectra/ I think this is my challenge with venture capital. The power dynamic masks the need for this conversation. Too often reduced to “they have money, I need money. I should go to them and try to appeal to them, to get the money.” No! They are looking for places to put their money that are going make them more money. Do you believe your business is going to make them more money? I actually think the most important thing for founders to do before they start fundraising is to be sure they’re convinced of their own business. Don’t come to me because you’re looking for validation. If you’re still looking for validation, you’re too early to be fundraising. Come to me because, you know you business and my priorities. I’m basically saying “yes” or “no.” I’ll invest if I think that getting on your train is going to also get me to where I need to go.

Nathan/ Growing-up in the valley and being around tech for my whole life, I’ve been told that it’s easy to get money, which it isn’t but it in a way it is. What, what you want is money from the right people—those who also have the knowledge, expertise, and network that will benefit you. You don’t just want anyone’s money. You want money from the people who are going to help you succeed—who are on board with what you’re trying to do. And, when you need money badly, it’s really hard to have the conviction to hold out for the right investors or the right sources.

Spectra/ I’m both an idealist and a realist. It’s all about evaluating and managing risk. Like if we do this thing, if we build this thing, you’re managing risk. So if this one investor is not as convinced as the rest of them, but they have a big check and they’re sold enough… go for it. They may have higher expectations of a higher bar but if they’re probably not going fight for you, it’s fine. It’s a calculated risk. Calculate the risk of them having a seat on your board. Then, decide. For me, I just want people to make intentional decisions and not because they don’t think that they deserve more or will ever find what they need. You’re the one deciding if this is a risk you can take. So are they.

I’m a multi-hyphenated person: Nigerian, black, immigrant, on the spectrum, LGBT, non-binary, etc. Of course, I’ve experienced friction in the systems in which we are in and sometimes fails me in some way. But, this is actually what gives me an advantage. This is where my edge comes from. I get access to better deals and cooler founders building unique opportunities that traditional Silicon Valley doesn’t have access to. I get deals from Africans, from Nigeria, I get deals from LGBT people. I get deals from black people. I get them from women. We are in an age where we are all hyper-connected. And for people like me who walk multiple paths and have multiple experiences, I’m super-hyper-connected. And that is an advantage because I mean, I’m just able to go literally where singular focus folks cannot. I’m one or two degrees removed at most from many people that I want to meet these days because of my identities. Most VC aren’t. They’re far away from these days and they don’t attract them.

The thing I want founders to know—especially those who may have one or multiple identities—we are in the age where community is wealth. It’s not a slogan. I can go to Lagos or Cape Town’s demo day just because of my affinity with other Africans and other investors who are building mission-driven ventures. And, I can stay locally in Boston. We are more connected and have more resources and access to more wealth than the dominant narrative tells us that we do. The othernesses that some see as weaknesses—they connect me to all these other places that the folks at Kleiner Perkins don’t get connected to. These perspectives allow me to see things that they can’t see.

Nathan/ I’ve always found that I see things others don’t. That’s what this book is about, to help people find opportunities they otherwise wouldn’t.\

Spectra/ I’ll just give you a quick anecdote. I remember working at this FinTech company as a product leader. I had just moved back from Nigeria and I had a boss who was excited about me and then intimidated when I got there because he realized I was more senior than him. He was constantly trying to block me out of things. We were in this room with the CEO and board, planning this huge conference. We were trying to get reputable folks from Boston to come and speak about finance and financial inclusion and education. And they threw-out a name that I recognized. Here was a bunch of white dudes trying to figure-out how they could get through four or five degrees to get to this person. But, I said that know that person. And they all looked at me, incredulous, and repeated the name thinking I didn’t know who they were discussing. And I replied, yeah, I know that person. I can email them and see if they’d be interested. I think this is actually something that they would be excited about. I was so innocent about it. The folks in the room couldn’t believe there was any way I knew who that is. They were talking about the governor. And, I agree “I know. He was at the event I threw just two weeks ago.”

I used to run an LGBT professional networking group, and he was there with the friend. And not just that event. I’ve seen him at all of my other events. And, when they were playing some song, I remember exactly where he was standing—that was in my mind. I may know him in a different capacity as them, but I know him—and it’s an even better capacity, a more personal one. These people were looking at me like there’s no way I have access to them because they couldn’t imagine him being connected to someone like me (because they aren’t connected in those ways). I am connected in these strange ways to people in governments and other positions because of our social experiences. And, now we all have a shared experience of the friction created in the world by all these very dated notions of who’s who, has power and who doesn’t. Slowly, these traditional people are finding their networks lacking and trying to look outside of their communities. The times have shifted.

Nathan: Thankfully.

This interview is from A Whole New Strategy: Everything You Need To Think And Act More Strategically