The Book I Wish I Had with Cheryl Contee

Episode 26 October 27, 2021 01:02:05
The Book I Wish I Had with Cheryl Contee
Why IT Matters
The Book I Wish I Had with Cheryl Contee

Oct 27 2021 | 01:02:05

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Show Notes

The other title for this episode was going to be “Love is What Gives Us Hope,” but you’ll need to listen all the way through to know why.  Tune in with Cheryl Contee, both a visionary futurist and pragmatic, highly-successful business owner and entrepreneur.  We dig back into the systemic forces that drive investment in technology and how they shape outcomes that have real consequences for equity of all kinds.  Rather than run away from what we call “The System” and allow the people and forces who have perennially benefited from retaining their power and privilege, we walk through how to completely eradicate “meritocracy” in favor of inclusion and the corporate and cultural structures that need revision.  We also talk about Chery’s book, “The Mechanical Bull,” and her successes, journey, and lessons from building businesses - this is a must-learn for underrepresented application developers and business owners.

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Episode Transcript

Speaker 0 00:00:07 Welcome everyone to another episode of why it matters. I'm Tracy, <inaudible> director of innovation here at now. It matters and I'm joined by my cohost, Tim Lockie everybody. Thanks for joining us. Um, today's guest is someone who I personally have had threaded interactions with over the span, I believe of about 10 years or more. And I just want to say, Cheryl, I am honored to have you here because I am both delighted to reconnect with you in 2021. And I've also had some of the most incredible conversations with you about what it means to look at our world and be visionary about where we want to go, but also be pragmatic about what we want to do and unpicking things like bias and race and, and how do we serve nonprofits? And I feel like you're a person who's done so much. Um, it's just a great, great, great pleasure to have you here. And I'll let you tell folks what you're on about now in 2021. Thank you for being here. Speaker 1 00:01:20 Oh, thank you, Tracy. And Tim for having me, I would say back at you at Tracy. I mean, I remember our conversations well, uh, and just, you know, thinking about wow, you know, she, they are so smart, you know, they are really smart and I wish I could find a way to spend more time talking to this amazing brilliant person. So this is a pleasure for me. So let's, I'll tell a little bit about myself. Uh, I am the chair and founder of do big things. Do big things is a digital agency that works with leading, uh, candidates, causes, corporations and campaigns to provide the new narrative and new tech for the new era in which we're living today. I am also, uh, the chief innovation officer at the impact seat. Uh, the impact seat is a venture fund that focuses on investing in the ideas that solve the world's biggest problems with an eye towards diverse founders because diverse led firms win. Uh, we do that through a three pronged approach of investment advocacy and philanthropy. Speaker 0 00:02:39 That's amazing. Um, I, and, and by the way, like throughout all of that, one of the threads is the technology we use in the future. We want to see. And I, we, we arrived at this point in, in our pre-game for the conversation, but I want to open up with the question of Cheryl, what is that future? What does that future look like? And what is the actual real implications, good, bad, and ugly for how we're all acting right now, because there's a lot embedded in the answer you gave us. And I want our listeners to hear it. Speaker 1 00:03:19 Well, it is a big question, you know, and I don't necessarily have a crystal ball, but, you know, because I tend to think differently than other people, you know, I've tended to, I think be pretty good at calling, uh, the next, the next challenge ahead of us. Look, we're, we're headed into a challenging time. There's no question about that. And I think there's a lot of wishful thinking about the end, you know, when is this going to end? And when can we go back to normal and that's not going to happen. Okay, we're never going to go back to the way things were. Uh, I think in particular, for example, you know, the great resignation, you know, people in the face of random and potentially early mortality looked around and said, I don't think I want to do this anymore, whatever it is. And I certainly want to be treated better if I'm going to do something differently. Speaker 1 00:04:16 And so that's putting a lot of pressure on, you know, the, the powers that be, you know, and including, uh, business, small business owners, but even, you know, big companies, big platforms, you know, no matter what organization you're in, you're likely having to make some changes in order to retain and attract your people. And that's, that's going to happen for a while. You know, people, I had to have this conversation with, uh, one of the folks that we fund, you know, they, um, one of the funds that we fund the, those funds invest in other, uh, diverse led firms. And they were trying to, uh, recruit, uh, an expert in HubSpot, you know, to their specific, relatively small, uh, California and city. Uh, and they specialize in FinTech. I was like, yeah, that person isn't there. And they're not going to come in the office. Speaker 1 00:05:09 Like, even if you could find that person in your city, which might be difficult, they don't have to come to the office if they don't want to. And we've heard, I've heard a lot of that, you know, that people just don't even, you know, they look especially women on whom the pandemic has been, uh, you know, very difficult, you know, for, for women and families, you know, they understand now how amazing remote work can be in terms of being able to manage your own schedule, which is so important, you know, especially when you're talking about navigating childcare. So on that front, I think on a number of different fronts, you know, people just don't want the same, same. Um, and, uh, another thing I think that's important to note is this time is going to go on longer than people think like it's going to take us longer even to get to the post period. Speaker 1 00:06:04 I would guess another 12 to 24 months. Why is that in this country? We still have large areas of the country that are dealing with rising cases of COVID or lots of cases of COVID at the time that we're talking, you know, holidays are coming up, people are going to be gathering, right? Like the same thing happened last year. We, we know what the we've seen this movie before. And, you know, because poor companies, I mean, poor countries are having trouble getting access to the vaccine because the pharmaceutical companies don't want to give up the formula to have it be made, uh, in country capitalism at work, the same thing could happen. Delta came from a country that where the vaccines, you know, were unavailable, you know, there's nothing to prevent another highly contagious, even more lethal version of COVID making the rounds. So you should assume that, you know, we might cycle through this in part because the systems that got us here, aren't the systems that are going to get out, get us out of it. Speaker 1 00:07:15 You know, whether it's inequality, whether it's climate change, whether it is, you know, putting this disease to bed and ensuring, you know, health care. So that's my, you know, my take and one of the things I've, I do a fair number of podcasts, and some of them are more business related, like really hard for, you know, these are, these are, you know, people who are not necessarily impact entrepreneurs, for example, uh, you know, what I've been saying is look, map your business slash life strategy to the world that is coming, not the world that you see around you today because that world is disappearing before our eyes. And so it's really important, you know, to look at the way, the ways in which things have changed and start to map in that direction, not hope that the changes that you've had to make and will make in this time, that those, that you, you can abandon them later. Speaker 2 00:08:14 Do you, do you think that this, that is really insightful? Thank you. And I don't hear anything there that seems incorrect. You're out of alignment. Um, I think it's just, most people don't want to say it out loud. Um, I'm really curious if you feel like a lot of this is business externalities. So, you know, it's a really intriguing thought, the systems that created this mess, they were good at creating this mess. They did some other things, but they also created this mess that that's like, that's what they're going to do. So looking at them to clean up this mess probably doesn't make sense. Um, are a lot of, uh, is a lot of this business externality, or do you feel like it, it would have come no matter what? So it wasn't extra morality that just the systems don't help clean it up. Okay. Speaker 1 00:09:03 I mean, this systems, you know what I mean? You know, by systems like, you know, thinking really macro, right. Just how we, how we engage in commerce, how we govern ourselves, you know, how we regulate, uh, things. Yeah. You know, like it worked for a time, but it was already pretty rickety right before this, like, you know, people were already, there was a lot of tension, you know, that's why Barack Obama was able to get elected. That's why Trump was able to get elected. That's why people are really into folks like AOC or Warren or Bernie Sanders, because, you know, these were people who were saying pretty clearly, Hey, these systems don't work for you. Do they? And I'm going to do something about it. The problem is that they haven't really been able to keep their promise. You know, there's, there's been at best, you know, incremental changes around the margins to make it the system slightly less terrible, right. Or in the case of certain administrations, like they didn't care how terrible if it met their ideological needs. So, right. You know, I think that looking at how, for example, our healthcare system is structured. It's not working the way that our educational system is. You know, it's not working. Congress is clearly a complete basket case, but that's not working like Speaker 0 00:10:30 What's going on in Congress right Speaker 1 00:10:32 Now. But if you think about it, if you take a really big step back, you know, Congress in its time was incredibly innovative in terms of the structure. But, you know, that was the 18th century. And we don't live in that time anymore, where the best that we can do is gathered together as many votes as possible. And then send that person to talk to some other people that other people have selected. Like, we don't even have to do that anymore. We could also just like vote using our mobile phones like we do for American idol. So, you know, at what point, right, if more people literally are voting in American idol, which that was the case for a while, then are actually showing up at the polls, like something is wrong, right? Like, we're not like we're not designing for the future. We're trying to hold onto this past. I mean, I read something by a conservative, you know, the other day who they called the constitution colorblind. So again, no, I mean, it's not like there's like a lot of racism just like baked in there. Like the fact, for example, that black people were considered eights of a person, like Speaker 0 00:11:45 Part of the constitution. Speaker 1 00:11:46 It was not in any way, colorblind. They were actually pretty explicit about it. So I think that there are people who write, you know, yearn for this yesterday that didn't exist and is not going to exist. Speaker 0 00:12:04 And COVID bye bye. What you are saying has sort of exacerbated our yearning, right? I mean, my, my wife will tell you, I look back at the seventies with the absolute rose colored glasses that we were all wearing back then. So I'm like, it was the coolest decade with the coolest music and the coolest clothing. But, you know, I'm aware that I'm doing that. I think what's happening as a society that you're calling out is that we're unaware of the fact that we are looking back on the way things used to be trying to get there in a context that is fundamentally shifted with this sort of wistful yearning of what life could be. Like, if we just go back to the same rigid structures that kept community segregated funding on available votes, disenfranchised, and people in systemic issues oppressed. Right? Yeah. Speaker 1 00:13:06 And there are people who are very threatened by the fact that the status will must change. Like th there is no choice. Like it, it must change in order for us to get out of this period. So yeah. You know, back to your question, Tim, you know, in terms of business externalities, those externalities are now internal. I mean, you just can't treat people the same way that you did before. You know, you cannot work the same way in which you work before the products and services that people are going to need are going to change and the needs that people have now, there are people who need to be retrained because the work that they did before the pandemic is going to go away like it's, and it's not going to come back, you know, and you also have nonprofits who are used to doing, for example, you know, in-person work, you know, on the ground, like field work and field is never going to be the same again, Speaker 0 00:14:09 Field so real big in the pandemic Speaker 1 00:14:12 That sure. Because, you know, all of a sudden they really, you know, had, you know, the old excuses of like, oh, but I know my community and I have this clipboard and you know, why would I share my old Excel spreadsheet names or my outlook list? Like, you know, none of those excuses, you know, held water anymore. Like you had to innovate in order to actually even just fulfill the basics of your mission and report back to the philanthropists who were funding it. So, you know, I really do think it is a, it is a moment in which of course everyone is trying to just, you know, put one foot in front of the other and survive at the same time. It really is necessary to pull back and look at, you know, how things are changing in order to adapt to the new realities in front of us. Speaker 0 00:15:06 Can I ask a follow up Cheryl on that? I want to know this. I went, I I've been candid about this in previous recordings. I went through a journey particularly during the Trump administration and also January six really did scar me personally because I was such a believer in the democratic system and my whole life had been shaped towards if we participate in democracy, enough, democracy will bend. Um, and I think the journey for me personally in 2021 has been where, where has change possible anymore. Um, and so the question I have, that's a very meta question based on what you are saying is, is the system itself that sort of big word, the system is the system itself broken enough to warrant wholescale replacement. And if so, with what, and if the system's not broken enough to warrant wholescale replacement, what are we doing wrong? That these voices that are critical to participation in it that have a direct effect on the day-to-day working lives of people in nonprofits or in the tech industry or in the startup world of, you know, developer apps, what are we doing wrong that we need to do different so that we can make the system work for us again? Speaker 1 00:16:33 Well, that's a big question. Speaker 0 00:16:35 I do that, Speaker 1 00:16:38 But I think those really are the questions that we need to be asking. You know, the SIS, you know, there are all kinds of systems are big systems, right? There are small systems, there's plumbing systems, ceiling systems. Speaker 0 00:16:51 Yeah. I'm interviewing to be on my town planning commission. I'm learning all about that plumbing and sewer and wow. Yeah, Speaker 1 00:16:58 That's a, it's a lot, it's a lot of responsibility. There's a lot of systems look, you know, we can all look around and see that the system is broken. Okay. Th th the system is fundamentally, it has, you know, begun to not be gone. So has, has failed most of the American public. Right. So, uh, you know, when, if you really embrace that, which I think most leaders in power have not because the system works just fine for them. Like they're okay with it. And they have an investment in, you know, a vested interest in, you know, mostly maintaining things the way they are and, you know, tossing people, a bone like a child tax credit, which I don't want to dismiss it. It's probably kept a lot of people fed, you know, and, and kept poverty at bay for many, many families and hungry children, but, you know, a child tax credit. Speaker 1 00:17:52 And it doesn't even begin to address, you know, the, the challenges, you know, we saw, you know, in the pandemic, how, you know, there were, you know, in a time when a lot of people had to teach kids from home, how was, how were, how was that going to happen? Like if you've got somebody working for minimum wage and their kid, you don't have internet access, don't really have a great computer and you actually have to go out cause you're a single mom. Like the system didn't work for any of the, for any of the people we're talking about in that moment. And still doesn't and still doesn't, it didn't work that great before, but they were managing barely right. They were surviving in that context. And in a context that, you know, continues in some of these places, kids still can't go to school or if they can, there's no job for that single mom to go back to if they were working in a restaurant, for example, that restaurant might've closed forever. Speaker 1 00:18:52 Certainly you can, you know, a lot of restaurants have closed forever here in the bay area where I live, where that were hugely popular before the pandemic and they're gone. So, you know, I do think that because the system, as we know it is broken for most people. Yeah. We're going to have to take a, a wholesale approach to figuring out how do we make sure the system works for more people and we've done it before. Like it's not, I mean, this is doable. Like we're, we're not. So, you know, for example, world war one and two, you know, that was the extremely painful and traumatic process of moving most of the earth from feudal societies run by monarchs to either benevolent dictatorships that had some sort of democratic, you know, engine or structure to it, at least in, in name only perhaps, or, you know, governments that were some kind of combination of capitalism, socialism, and democracy. Speaker 1 00:19:57 Those systems don't work anymore. It's not, again, the people for whom it does work, don't want it to change. And yet there's a whole bunch of people who elect them, you know, or that they represent who, you know, are starting to ask some big questions. So, you know, what does that mean? You ask like, you know, what, what, what comes next? You know, I think a lot of negotiation, you know, we can see it right now, you know, in the, in the halls of power where you have, you know, people who, you know, are shouting at the top of their voices that, you know, we're going to have to do things differently in the future. If we expect to, you know, democratize success and prosperity. And there are people who are resisting that because they think that if they give that any kind of, where other people get more immune, somehow they might get less. And that's the, that's the attitude that we have to change Speaker 0 00:20:57 That sort of perspective on, you know, for lack of a better way of saying it, make the pie higher. Right? I mean, I described this as a rising tide lifts, all boats. And the problem is, is that sometimes the tide rises five centimeters and that's negligible to someone who already has a fancy boat, but it means the world to somebody who doesn't. And that might be enough for them to get where they're going next. I, what gives you hope? Because I have been short on hope and long on cynicism this year. What gives you hope? Because we haven't even begun to unpick a lot of the structural sort of outcomes of all of this, but how do you, how do you retain hope right now? Speaker 1 00:21:48 No, that's a great question. I mean, you know, right. You're, you're right. We have not unpicked or, you know, unpacked, like, you know, the reality of the structural outcomes to then look at the structures and start to, you know, make some course corrections. Absolutely. Like there's a lot of people who are in complete denial about that. Uh, you know, what gives me hope is, uh, the creativity and resilience of human beings, you know, like I do believe that we can figure it out, uh, you know, we can figure it out the easy way, you know, that song violence, you know, with negotiation where we can do it the hard way, like world war one and two, you know, like there's, we can be, you know, we can have a peaceful transfer of power, like, you know, uh Declarc to Mandela, or we can not do that. Speaker 0 00:22:43 I love that you just invoked Declarc to Mandela, uh, by the way, thank you for that. Uh, because you know what I am looking at in some of the work that you're doing in particular, and I, I want to ask you to put on your VC hat for a minute. Um, because you know, when, when we're looking at something like the impact seat and the work that it's trying to do, how do you create measurements and indicators that tell you that this is really actually sustaining that new hope versus just throwing good money after bad, trying to perpetuate the system that we're in, because I would agree with you that the system's broken, what I think we're all disagreeing on is how to fix those mens. Like is, is the system so broken that we need to throw it out? Or is it just the limitation of our imagination around what's possible? That's broken? Speaker 1 00:23:40 Oh, no, I disagree with you that th that there are people who, that everyone agrees that the system is broken. I mean, you know, conservatives are Here and there, even some, you know, like you've got a Joe mansion, you know, was basically like, you know, I don't want to change the system because then that might give people hope or expectations of help in the future. Speaker 0 00:24:06 We don't want to, we don't want to like, you know, create the idea that government should be there for the people. Speaker 1 00:24:12 Yeah. Or should it help you in any way, even though it's your money, it's your money? Like, you know, you, that has seems also to have gotten lost in the context that we're talking about taxpayers money, like the idea theoretically of taxes was that, you know, you pay into the system and the system, you know, together, if we pull our resources, you get it back. But actually it comes back to you in the form of roads and education libraries, you know, clean water, like that was the theory. And again, like that concept, you know, it has really begun to erode, you know, that the government feels like it's the government's money, not our money. Right. So that's, that's number one, right? Like let's return to actually dialoguing about like, that's our money that needs to come back to us in ways that we can feel and understand 'cause right now, half of that budget goes to the military and like, what are they spending that on? Exactly. People should be asking more questions about that, but yeah, in terms of though, you know, what gives, what was the question again? So Speaker 0 00:25:23 What gives you hope was the starting question, but then I, I had asked you, you know, in explicit, what do you measure then to direct to this fix? Speaker 1 00:25:33 Well, look as a, as a VC, you know, there are, there are parts in VC, you know, venture capital, you know, for those who are unfamiliar, you know, in the VC world, you know, for those of us who are trying to make an impact with our investments and actually solve big problems, not necessarily small problems, but, but bigger problems, even that even talking in that manner and making that a priority is a pretty major shift in the way that, you know, for example, you know, in the 20th century, right, that then people were investing like that concept is still, is still novel to a certain extent. And when you look at, for example, the amount of venture funding of any kind seed pre-seed seed all the way through series D you know, when you look at the amount that goes to women, that's something like, it's still something like two to 4% of all venture funding going to female founders, which if you understand that women by 75 to 85% of everything, okay, look it up, look it up. Speaker 1 00:26:38 If you don't believe me, we buy all of the things. Those two numbers don't make any sense. Okay. That is some, like, you know, like 19th century thinking that that would even in any way make any sense. I mean, why wouldn't you want the people who are some of the representatives of the people who are going to buy the product to inform you about the product or service it. Right. Okay. So, uh, one of the things, for example, it gives me hope, uh, structurally you've probably heard that the NASDAQ has changed, uh, their rules around boards, and it didn't get a lot of media, which I don't know why, because it's actually a really big deal. Uh, so for those of you who are unfamiliar recently, the NASDAQ, uh, you know, trading platform said, look, you know, starting now, you know, we're going to give you a little time to figure it out, but starting now, you can't be, you can't be listed on the NASDAQ unless your board has diverse representation. Speaker 1 00:27:39 And, you know, you might think, you know, your immediate thought might be like, oh, you know, are they being nice? Like, is it virtue signaling, you know, these that they know they're doing it because it makes money. Okay. Like all of the studies show, all of the data shows that diverse led firms are more innovative. They are more productive, they are more profitable. So if you want ROI, you need DEI and taking away that excuse because, you know, you're, we're all in tech. You've, you've heard these, there's like, oh, there's not the pipeline. Oh, you know, I believe in meritocracy, like, blah, blah, blah, blah, blah. When you remove those excuses, then it's like, okay, if you, if we're all acknowledging that diversity of that form makes more money, and you have said that the most important thing is to make money. How are you changing your business practices? Speaker 2 00:28:39 Yeah. I mean, it's interesting. Just thinking about NASDAQ on that. Isn't another word for portfolio diversity. Like we have, like, there's nobody out there with that would not say you have to have, you know, a strategic pro portfolio, but when it comes to human capital, like that's just been completely overlooked. Um, so, Speaker 1 00:28:59 Uh, yeah, no, exactly. Tim and, and that's why I say, you know, when logic leaves the room, you can be sure that racism and sexism and homophobia have entered because none of this, none of what I talked about just now makes any sense. It doesn't make any sense. Uh, except it, it does privilege, you know, a certain group of, you know, people, you know, who've been trying to keep, you know, this, these systems and this access to themselves, um, you know, to their own benefit, even, even if it's costs, even if it costs them, it feels safer. You know, that, that kind of thinking is starting to away. I, Speaker 0 00:29:43 Yeah. Finally learn, oh, I was just going to say, I've finally learned in job interviews. Now this took me 20 years or more in tech to finally learn in job interviews that when I'm talking to a leadership team member of an organization or a business owner who is selling me on the idea that what they are running is an absolute meritocracy and all ideas are valid. That actually doesn't mean I have a place. What that actually means is that they are saying in a very direct way, I believe in the status quo. And I believe that I benefit from the status quo. So you are here to benefit me, benefiting the status quo. And that's why this is a meritocracy, uh, because I benefited from that meritocracy and now you need to imitate me. There is no space for you to be anything else. Other than that, that took me 20 years to figure out and some really hard lessons along the way. Speaker 1 00:30:42 Oh yeah. Meritocracy. Yeah. What it means is, well, I'm on top and I deserve to be on top. Speaker 0 00:30:47 Yeah. And I'm blind. Speaker 1 00:30:50 Yeah. Yeah. Yeah. I don't want, let's not talk about that. You know, I worked hard, like sure, you worked hard, but you know, you asked about metrics. So, you know, I'm a senior advisor on a fund on a bunch of different funds, but you know, this fund focuses on, um, female led startups and they told me, look, Cheryl, you know, we work really hard to lead as much bias out of our system as possible so that we could get more, um, women of color founders funded. And I said, you know, we felt like we did a pretty good job until it came to venture capitalists, writing checks. And these angels who, you know, at least theoretically, you know, said that this was a thing that they wanted to do, but it took them on average, uh, six or seven introductions to funders to get a white female startup funded. It took them 55 0 to get a woman of color startup funded. Wow. So America literally asked me to do 10 times the work in order to get the same result, which is something I write about in my book. Ah, mechanical bull. Speaker 1 00:32:09 Yeah. So for those who don't know, you know, my startup attentively, um, was the first, as far as we know, uh, with a black female founder to be acquired by a NASDAQ company, there was a company before mine, 20 years ago, probably a one eight a lot, um, was the first woman of color to have her, um, her, uh, company was bought by a New York stock exchange. Um, so yeah, you know, for that to have happened in 2016, something is wrong. You know, it's not like black women don't work hard. It's not like we don't have good ideas. Right. Like, that's crazy. So, you know, how do we start to build more logic? So in the book, you know, I talk about that, you know, how did I, how did I get through and how did I get to a successful exit, which, you know, has been elusive, um, for people, you know, who come in a package like this, uh, you know, but I wrote the book about, I wish that I'd had, you know, someone sat me down, you know, after, you know, the exit and said, look, Cheryl, more people have been to the moon literally than have done what you have done as an American. Speaker 1 00:33:19 And you have an obligation to help others. So mechanical bullets, it's not just my story. It has a lot of investors stories that has a lot of a diverse set of other founders stories. But, you know, every chapter is describing the process. It describes the life cycle, but it's also, you know, if you don't look like, you know, a, uh, Harvard or Stanford dropout, who is a white male, who comes from an upper middle class family, you know, here's the, the thing that's going to happen to you, maybe what the speed bump that might happen to you at this phase and here's how to get over it. And, you know, at most of the, um, most shoppers also have an investor insight, which, you know, if you're an investor who says that you're, you want to help startups like this, here's a way in which you can be helpful. Now, Speaker 2 00:34:07 Can you give us an example of both a speed bump and an investor insight from, from a mechanical bull? Speaker 1 00:34:15 Ah, so a speed bump, for example, is just getting funding. As I mentioned, you know, like if you, you know, you have to plan, you know, that it's going to take you. And I, you know, when they told me that number, it made sense to me because at some point I figured out in the process in getting our, um, first checks in for attentively that it was a numbers game that I was just going to have to knock on a lot of doors, you know, in order to find that investor. And I didn't, you know, I just intuited that, but yeah, you know, it's going to take you longer and you're going to have to knock on more doors. And also, you know, because, uh, you know, there's no runway, right. You know, there's usually it takes six to 12 months to have a funding cycle. Speaker 1 00:34:57 You know, if you are, you know, a woman or you are a minority or God help you, if you're both, you know, it might take you not six months, but 12 months to, to raise that money. And that has direct impact on your runway. You know, you have to plan to stretch that money a little bit further, which is not fair, but right now it's the way it is. So, you know, those are the things, when we talk about structure, you know, it should be, you know, it shouldn't be perceived that businesses that are diverse led are riskier because that's why it was hard to get those checks. And it's like, oh, I don't know, something, something, something feel right. I feel uncomfortable. Oh, right. Yeah. I just, I feel uncomfortable. Or maybe they feel more comfortable over there. Yeah. You know, like, no, it's, it's, it's, that's not, that's no. Okay. Uh, they're not only are they less risky, like someone who is willing and able to talk to 50 funders, that's a person worth investing in, right. That's a person who believes in their product. That's a person who is dynamic, willing to work hard, willing to do the research, which are all of the things that investors say that they want at the seed stage. Speaker 2 00:36:20 What, and what do they really want? I mean, are they looking for what they have funded in the past? Is it just like, they're just looking to do more of the same because that's less risky what's um, yeah. What, what is it? Speaker 1 00:36:35 Yeah. Pattern matching is a thing, you know, that people often talk the talk about where, you know, and that was a really big problem where, you know, there was a John Doerr, you know, came right out. He's a big investor. Right. Tracey's heard of him, she's nodding her head. Uh, you know, and he came right out and said, you know, when I see, you know, a business, you know, a startup that's led by, you know, a white male drop out from Harvard or Stanford or MIT, you know, I'm going to invest in that because in the past investing in that made me a lot of money. Right. But there's a lot of people who aren't that a lot of people. So, you know, that's a, that's a challenge, you know? So an investor insight, you asked for an example, you know, in the past, you know, like for example, in tech, you know, we're all technologists, you know, there was this perception that, you know, white men were driving, you know, adoption, which I don't know that it was ever true, but that was the perception. Speaker 1 00:37:31 So Google glass would be an example right. Of, you know, not understanding that women by 75 to 85% of everything, you know, they only tested it on white guys basically in, or that they gave it out to a bunch of like, you know, white nerds, you know, thinking that would make it hip and cool and popular. When in fact, you know, the people who drive, if you actually look at the numbers again, this is where racism and sexism and homophobia, distort market forces. You actually look at the data, the people who drive tech adoption are millennials, moms, and minorities, what used to be called minorities. Right. So, you know, by apple understands that, you know, almost every commercial they have is extremely diverse and has more people of color. Right. So they get it right. Of like, you know, there are women, you know, actually in virtual using it. So, you know, so our CTO at my old company attentively, you know, she was testing out Google glass. She was an early adopter. And she said, you know, I love this because I can pictures with my kids, you know, and not have to have a phone in front of my face. You know, it's feels more natural, but, you know, I wish there were some recipe apps, you know, there are four golf apps and zero recipe apps, and I'm going to quote her. I don't know who they're building this for. Speaker 1 00:38:55 So that's my investor insight. It's like, do you actually, if you, are you actually thinking about wha why, why this product will or will not be successful using the data and not your feelings or your sense of your own personal culture? Speaker 0 00:39:12 I did in a different life, you know, before I fell into non-profit tech. And I'm, I'm very clear. I did fall into nonprofit tech. I got a master's of public administration, and I was gearing up to be a policy wonk of some nature or another for where those master's programs shunted you in the nineties was there like go work for the government, right? Well, we'll teach you all the government stuff and you'll go do policy analysis. Um, I moved out to the west coast instead, and I wound up working for an organization called the applied research center, which published a magazine called color lines magazine. Cheryl, I know, you know, these places, uh, the founder, Gary would always say, you, you, you can't look at the intent of people doing policy. You have to look at the outcome of the policy itself. And at the time that was a revolutionary way of doing policy analysis, which was now 20 years ago, because policy analysis was always as an extension of existing structures, not what the people who are on the ground were experiencing it. Speaker 0 00:40:24 And then you sort of backwards engineer the policy. What you're saying makes a lot of sense to me, you know, when you relate it to the struggles of people who are affected by wide-scale policy decisions. I mean, one of the most interesting and heart-wrenching things I ever looked into was what was going on with downwinders on, on Navajo nation, for example, and, and how policy didn't care, you know, the policy was to drive the space race, and the competition with the Soviet union, the policy did not consider the outcome on the downwinders. And I want to know, like, what now do you think has changed in the industry? Because we were talking before we hit record about, you know, the moment that 2020 gave us, I have some cynicism about its durability, but I feel like maybe you have more hope in terms of shifting the way that industry think about this, that produces a more equitable outcome. Speaker 1 00:41:34 Yeah. I don't even know if it's hope Tracy, you know, it's just, it's literally looking at, you know, what's happening. I, you know, I think it's, I, everything you've said about policy is correct. And even the concept of nonprofit tech, like that is a thing, you know, and I, I do a fair amount of talking to, you know, younger people, you know, in MBA programs or college programs. And I say, look, the job that I have now did not exist when I was in college. I was part of a cohort that created it. And that is especially true of your generation, that the, the jobs of the future aren't here yet, and you might have to invent them. And you know, everything that you're saying about policy is now being applied to, you know, capitalism and businesses where people are saying, look, which is, you know, back to the future, you know, certainly the early 20th century was a lot about that, right? Speaker 1 00:42:26 The impact. But, you know, you can't just start a company, you know, with a certain intent and not look at the outcome. People are, are really demanding that companies take responsibility for the outcome of what their businesses generate in the world. And, you know, that's new, at least in this century, in this century is not new in the last century. You know, a lot of the, you know, workplace reforms, you know, certainly were, you know, driven by people saying, Hey, you know, it'd be cool if, you know, you didn't have children, you know, working in cutting their fingers off in factories. Like, it'd be great if you allow people to go to the bathroom, for example, in, you know, this giant seamstress factory or et cetera, Speaker 0 00:43:13 Week 40 hours. Yeah. I mean, you're talking about the labor movement, right. This is sort of like the 21st century version of that. I see. I see where you're kind of heading. Yeah. Speaker 1 00:43:24 But yeah, but it's beyond labor, you know, if, for example, you know, Facebook right now, as we speak is under a lot of pressure for the fact that they knew they looked at their own data and knew that Instagram was harming teens and did nothing. They did nothing. Okay. And that guy, their CTO was recently gently fired. I don't know if people noticed that or not. And, uh, you know, he's been there, he was there for 13 years, you know, he presided over all of this, like failure to actually adapt in any way or take any responsibility for the outcome, the outcomes of, you know, Facebook's products, the person that they put in his place does give me a little bit of hope. Uh, it's the person who was running the hardware division, uh, at Facebook and that, you know, if you've used any of, um, Facebook's hardware, like the Oculus quest two, I've got one right here. Speaker 1 00:44:21 Uh, I have one at home and in the office, you know, I have been using portal, you know, during this time, which is a great, it, it allows you to tell augmented, uh, reality stories. It's a great, you know, grandparents to grandchild, uh, facilitating, you know, it's magical. I mean, those products might as well have been made by ma you know, fairies from outer space. Like they are so elegant, you know, they're, they're really well done. So, you know, my hope is that, you know, someone with at least like more, uh, a broader sense of sensitivity and an ability to inspire their team, you know, to literally creating magic will do something to improve the newsfeed of Facebook and Instagram. Uh, but in the meantime, yeah, you know, I out other outcomes are climate change. You know, the, we have lived through, you know, the ability of, you know, all of these companies to pour whatever they wanted into the environment. You know, again, with, you know, in the latter part of the 20th century, some pushback, you know, from the environmental movement, you know, somewhat successful to at least make it slightly less terrible. But in the meantime, the climate change, you know, they, they weren't successful really on that front. You know, we're, we're right now starting to get ankle deep in it, literally and figuratively, you know, the systems that created climate change are not the ones that are gonna get us out of climate change. End of story. Speaker 2 00:45:52 One, the, that therefore Speaker 1 00:45:53 You have to look forward, you have to look forward to the people, creating the things that will do that. Speaker 2 00:45:59 One of the things I hear you saying here, or I'm curious if I'm hearing you say it is, I think there's a, a B if there's a before and an after the, before is, you know, you drive bottom line decision making in your company for shareholder value and the after is going to be, if that, if that is also not creating value or at least not creating negative value for the earth and for not just shareholders, but the people buying your products, um, then you don't ha you actually don't have a company, uh, talent, won't, won't show up their investors, won't show up there. Your board will look at that and, and be like, I don't want my name attached to that. Uh, uh, is that when you look at vectoring for the future and, and business strategy, is that what you, is that what you see like an actual double bottom line, if you are not hitting both of these, then a symbol doesn't cut it anymore. Speaker 1 00:46:59 Yeah. I think we're, we're all seeing that, you know, in, you know, in play, you know, where if you're not, um, you know, and even even like that concept of shareholder return, right? Like, you know, if you're only investing, you know, for example, in acquiring companies that are only led by white guys, you actually aren't driving the maximum shareholder value. Okay. You aren't, but so that, you know, we can take that off the table. Like, you know, if you are a world in which your shareholders are going to die, because their homes are going to their fancy homes and Malibu are going to burn down, you're not creating shareholder value. Okay. Like, so, you know, I think we're in a process where like, redefining, like, what do you really mean when you say shareholder value? Because it actually like two plus two doesn't equal five. Speaker 1 00:47:50 My man. Okay. So like, please explain yourself again, like what you think you were doing with this company and think about how you might make it, make it different going forward, because yeah. You know, you looked at Facebook, you know, and I, you know, I have been a fan, you know, I've been a Facebook users since, before it was cool. You know, a lot of my stuff, you know, about my son, you know, it's probably the main way in which I keep in touch with a lot of my cousins, but they're having trouble recruiting, you know, that like recruiting is a lot harder for them. And so as retention, you know, because of their policies and then that starts to erode shareholder value because you're not as efficient as you used to be. So, you know, I think that, that, you're absolutely, you know, Tim, you know, you's zeroed in, on, you know, the fallacy, right. You know, the fantasies that we've been sold, you know, just aren't cutting it in this period. We can all see it. Now. We're all starting to strip that away. You know, COVID really forced us to look at a lot of that stuff. Speaker 2 00:48:50 Well, and, and a lot of this is going to drive scarcity to a degree where wealth is actually not able to insulate in the way that it used to. You know, you see that in Portland and the fires in Washington. And, um, and I think that's actually starting to drive a collective consciousness that has kind of been held by a few extremists or considered extremists that are now like going to be considered mainstream kind of overnight, um, which is, which would be very hard pill to swallow by that way. Yeah. Speaker 1 00:49:21 Oh, absolutely. Let me show you just a super quick graphic. I don't know if you've seen this. This is from a, uh, a deck that I did, um, on generational wealth and, you know, you can see the numbers, right. You know, like if you're white, this looks amazing for you. Right. Congratulations, white people like that looks amazing. This looks slightly less amazing for people who are, you know, people of color. And, you know, if you juxtapose that in your mind with the fact that in just 20 years, most people are going to be these people okay. In America, like this is not okay. Like this does not equal a safe, you know, safe functioning society. Like that looks like the French revolution. Okay. And Speaker 2 00:50:14 That's great humility. <inaudible>, you know, like literally 25 times less sunny, you know, Speaker 1 00:50:24 Right. In a way that, you know, like, it just doesn't like, even if you, you know, think that, you know, oh, well, outcome shouldn't be fair or equal, like the distance between those numbers, you know, in terms of what that will do to our economy. You know, if there are just fewer people who have more right to spend. And so many people who have so much less to spend, that's not, you know, the middle class is what has always driven American prosperity. And, you know, if we think that, you know, concentrating wealth and power in the hands of a few people is, you know, then a spell, you know, a peaceful and prosperous society, again, a fantasy. We can already see that unraveling right before us Speaker 0 00:51:10 Cheryl. One of the things that you're also implying in all of this is adjusting our expectations of timeline of delivery, or at least that's what it feels like to me. And I don't have an answer personally yet for how do we make that leap in our thinking? So I believe everything. I mean, like I'm an absolute believer in what we've been talking about, but when confronted with a business, that's like, look, that's great for 10 years from now, but what I really need to solve for is Q4 and Q1. And we're going to go full tilt towards Q4 and Q1. And we'll worry about cleaning that up later. How do you break through that logic? How do you even begin to make a dent in that when it's always going to be, you know, Q4 Q1 or Q2 Q3, that's coming up, that's going to be driving the interest. Speaker 1 00:52:14 Oh, you know, look, I've been a business owner for, you know, it's starting to get to be 20 years now. Okay. And yeah, of course, you know, you've got your numbers, you know, that are right ahead of you. You want to end the year, you know, in the black for sure. But you know, anyone who's not looking around at their competition, you know, to figure out, okay, well, how am I positioning myself? You know, within this marketplace, how can I differentiate myself? You know, and you know, what is the, what does you know, where are the gaps? You know, what are the problems and can, are we really providing a solution? You know, you're not your business. Isn't going to stay in business very long. You know, if you're only thinking, you know, 90 days ahead, right? Like, you know, businesses that are successful long-term and, you know, most businesses fail by they're in their first year in America. And of those that succeed, most of those are gone by their third year. So if you want to make it past three years, you got to think past three years. Speaker 2 00:53:19 We, um, I think that we've been surprised to find that philanthropy also is a more time bound in terms of its investment horizon than we expected. And so we've just engaged philanthropy, um, as an organization in the last year. And that was surprising to us. Is it surprising to you? I mean, it seems like you've been in this, in the philanthropy world longer. Um, does that, does that track, is that, uh, does that make sense? Speaker 1 00:53:47 It doesn't surprise me, you know, again, there, you know, a lot of these folks are, you know, products of the systems for eight, you know, they, they know those systems well, and, you know, even, even as they are working to, uh, you know, improve people's lives, you know, they're doing it within the context that they feel familiar with. And, you know, in COVID I was actually, you know, both surprised and, uh, you know, heartened by the fact that a lot of from know, uh, philanthropic institution said, you know what? This is a year where we know that we're only required to spend five, five, whole percent of our, you know, of our treasurer, you know, on, uh, helping other, uh, you know, helping people. And this seems like a time when maybe we need to spend more than that. Maybe a lot more people need a lot more help right now. Speaker 1 00:54:43 And that's going to be true for a while. You know, it's going take it's, you know, this is a global transformational and traumatic event. It is going in, we will never go back to normal. That's clear things are going to be different in some very specific ways going forward, probably permanently. And, uh, you know, there are more people who are recovering, who are figuring out, you know, how are, how are we going to make it, you know, going forward. So, you know, I do think that there are ways in which, um, you know, foundations can support, um, nonprofits in particular right now. So many nonprofits need, uh, training, you know, they're, you know, we saw, you know, in the, you know, in the wake of COVID, you know, how far behind, um, the nonprofit, uh, you know, tech infrastructure has become compared to corporate infrastructure. Speaker 1 00:55:43 And so, you know, this is, yeah. I mean, it's really, you know, as someone who sits at the juncture of both, you know, seeing what people are doing, how they're approaching, um, you know, tack, you know, in service of goals in the corporate sphere versus, you know, the th you know, the nonprofits fear like light, like 10 years behind. Okay. Easily. Um, and so they need to get in order to really achieve change, especially in this time, how are you as a philanthropic leader? How are you helping your grantees get 10 years ahead, leapfrog 10 years now, Speaker 0 00:56:17 That's been a personal pain source. It's like, we can build a hundred year clock, but we can't build a hundred year foundation. Speaker 1 00:56:26 Right. Or, and even if it's not a hundred years, even if it's like 10 on your grantees now to actually be 10 years ahead of the people who are oppressing, right, who are, you know, the systems that are, you know, keeping people down, like, and there was a time I'm not talking about a thing that's not achievable. There was a time when, you know, aside from porn, you know, nonprofits were actually the cutting edge, absolutely. On the cutting edge and way ahead of corporations. And we were kicking their asses very successfully and they felt that they felt it and they figured it out, and they very much invested and up their game, you know, and accelerated forward in order to more effectively in part, um, you know, cope with, uh, nonprofits were putting pressure on them. So, you know, this is a problem, you know, the knowledge gap and the skills gap, the strategic gap between, you know, corporate technology and nonprofit technology, that's become a pretty wide chasm. Speaker 1 00:57:36 And, you know, that's a place where, you know, foundations really can play a huge part because look, it's hard for a grantee to come to a foundation, say, uh, you know, our digital beam is not as tight as it could be. Can you help us? Right. Like, that's a lot to ask, whereas you already know, okay. Like we all live through COVID, you know, your grantees, you know, have just barely, you know, done probably the minimum in some cases, right. To be functional during COVID. So you need to help them move forward, move further, faster in this time. And you can, Speaker 0 00:58:15 Yeah. We touched Leon Wilson from the Cleveland foundation who talked a lot about this too, at one point as well, and really hammer down on that idea that this is about acceleration, not reinforcing the status quo. Speaker 1 00:58:30 Yeah, exactly. Speaker 0 00:58:35 I mean, Cheryl, this is the conversation that I could just gently go through for the rest of my day. I really am so grateful for the time you've spent. What's the burning thing. That's on the tip of your tongue that you want to make sure gets out there in the world, uh, regarding all of this. Speaker 1 00:58:53 Well, no, I'm so grateful to you, Tracy, and you, Tim, you know, for having me on. And yet I don't always get to, you know, talk about, you know, this stuff, you know, I, I definitely see myself as a futurist, you know, the way in which people are working now, all of my teams had been virtual and remote everyone to started working the way my team has been working for over a decade. So, uh, you know, I've been pretty good at sort of, you know, seeing where the future is going and yeah. You know, I want people to have hope, you know, at do big things. Certainly, you know, we wouldn't, you know, we have an amazing team out there that works, you know, side by side, you know, with nonprofits too, you know, and, you know, build movements of millions of people, you know, who actually do care about the future, you know, at, uh, the impact seat, we're funding the future. We're building a new economy, you know, with every investment, you know, and an economy that hopefully will, you know, again, work for more people and build more prosperity. So, you know, that's, that's what I'm focused on right now. And I hope that other people will, you know, your takeaway will be, you know, what am I doing, you know, to impact the future, even as we all struggle through this present moment. Speaker 0 01:00:13 Gosh, Speaker 2 01:00:15 Cheryl, thanks for that. Um, really appreciate it and thank you for, um, thank you for sharing hope. Um, I think that there are a lot of features to, um, uh, kind of roll the other direction, uh, on, on hope and, and I think it's an easier message to sell. Uh, and so I appreciate that, you know, uh, there's a lot of hope in what you talk about, Speaker 1 01:00:38 Easier for whom, you know, one of my, you know, big fights that I've had with clients and the environmental movement is that, you know, the gloom and doom, it only attracts a certain group of people, you know? And in fact, what inspires in all of, again, all of the research says this, what inspires most people, you know, to work on behalf of the planet is love. It's love and spirituality and positivity, you know? And so, you know, that's been really tough. So, you know, Ted lasso, you know, one of the great things about, you know, American culture and one that continues somehow to buoy us along is our relentless optimism. It's that relentless optimism in the face of things that should make us less optimistic is why it overwhelmed, overwhelming, right? Like evidence that it might be hard, you know, it's why we went. It's why we do the impossible. Well, thanks. Y'all Speaker 2 01:01:37 Cheryl. Thank you so much. I'm tin lucky. Speaker 0 01:01:40 I am Tracy. Crohn's Zack, and you've been listening to why it matters. Speaker 2 01:01:45 What matters is a thought leadership project of now it matters a strategic services from offering, advising and guiding to nonprofit and social impact organizations. Speaker 0 01:01:54 If you like what you've heard, please subscribe, check out our playlist and visit us at now. It matters.com to learn more about us.

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