Full Transcript: Isa Watson, Founder And CEO Of Squad By Envested On GHOGH Podcast

Full Transcript: Isa Watson, Founder And CEO Of Squad By Envested On GHOGH Podcast

Isa Watson
Isa Watson is the founder of social community platform Squad by Envested. Photo: Anita Sanikop

In episode 35 of the GHOGH podcast, Jamarlin Martin speaks to Isa Watson, founder and CEO of Squad by Envested, a VC-backed software company that is scaling a next-gen platform to build relationships at work.

You can listen to the entire conversation right now in the audio player below. If you prefer to listen on your phone, GHOGH with Jamarlin Martin is available wherever you listen to podcasts — including Apple PodcastsSpotifyYouTube, and SoundCloud.

Listen to GHOGH with Jamarlin Martin | Episode 35: Isa Watson
Jamarlin talks to Isa Watson, founder and CEO of Squad by Envested, a VC-backed software company that is scaling a next-gen platform to build relationships at work.

This is a full transcript of the conversation which has been lightly edited for clarity.

Jamarlin Martin: You’re listening to GHOGH with Jamarlin Martin. We have a go hard or go home approach as we talk to the leading tech leaders, politicians and influencers. Let’s GHOGH! Today we have Isa Watson, the founder and CEO of Squad by Envested. Welcome to the show.

Isa Watson: Thank you for having me.

Jamarlin Martin: Let’s talk a little bit about the platform that you’re building. Can you talk about what problem you are solving?

Isa Watson: Squad is a social community platform and the problem that we’re solving is the fact that people have a hard time cultivating community in the different aspects of their life. Right? So there’s a community that they’re trying to form at work. There’s community in their fitness environments. There’s community in their apartment buildings, whatever the case is. And so with Squad by Envested, we actually started in the workplace as a workplace community engagement platform where people could, at the community level, that’s essentially the whole workplace, but you have groups of people based on interests. So you can have your “new moms” group, your “marketing group”, your “book club group”, etc., and those are called squads and what the platform is, is a central repository for all events and activities going on amongst those groups in the community at large. And what we found was that when we were in the workplace working with companies like Walmart.com and Jet and Vevo and companies like that, we found that the user actually was very interested in not necessarily having their work community as a completely separate entity, but in having their work community consolidated with all the other things that they were interested in. And so with Squad by Envested, you’re able to join multiple communities from your work community, like I said, to other communities that you’re a part of, but having a central repository for all events and activities and things going on in your community. So when we talk about our value proposition it’s really about bringing online communities offline at scale and as a digital native and a millennial, we know that that’s something that we don’t necessarily do as well, being able to kind of cultivate in person opportunities.

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Jamarlin Martin: Let’s talk about your academic background. Seems like you’ve got like 10 degrees in different subjects. But can you talk a little bit about your background?

Isa Watson: Yeah, sure. So I started my career as a chemist. I was always a STEM kid. I love complex problem-solving. I love putting things together and making sense of smaller intricacies. And so that manifested itself in me wanting to study chemistry. At one point, I thought I was going to be the top researcher in some type of oncology and that was my goal. And so I studied chemistry, went to Hampton University and then I was a diabetes chemist at Pfizer. I was really interested in that area because there’s a lot of instances of diabetes in my family. And then I was a clinical data scientist for the drug Lyrica, also at Pfizer. I did my masters in pharmacology along the way. And one of the things, my transition from science to non-science was interesting. I was really interested in expanding my skillset. As a scientist, you’re really in the lab focused on this one thing for an extended period of time. And I really wanted to broaden my skillset and understand not just how science can be created but how science can impact the world. And so I said, ‘Oh, I’m gonna go to business school’. So I went to MIT where I got my MBA and focused on econ and finance, and I thought I was going to go back into business development for pharmaceutical companies, but interestingly I had a lot of opportunities that were thrown at me when I was in business school when I was in the recruiting process, and ended up landing in a completely different place than where I thought it would be, and that was on Wall Street. So I went to JP Morgan Chase where I was working for the senior leadership team in this kind of leadership training program that Jamie Dimon had created, called the management associate program and essentially I was actually launching and building a number of strategic initiatives across different parts of the firm. And so before leaving to found Squad, that was kind of my career path and the catalyst to me leaving JP Morgan to found Squad was really on understanding and first of all, seeing such a great scope of things and divisions at the company. JP Morgan is a 250,000-person company, but also actually seeing the divisions where community was the strongest and understanding the impact that that had to the ROI of that business. And so having those nuances gave me the conviction that this was a problem that can be solved through technology at a much larger scale.

Jamarlin Martin: Folks are starting to reap the value of getting an MBA, getting a masters, even going to college. As you know, there’s a massive debt overhang on students and the economy. How would you rethink investors, corporate America, they want to see the MIT, they want to see the MBA, but to do what you’re doing now, maybe it’s not worth the trade off in terms of the debt?

Isa Watson: I have two conflicting perspectives on it. I’m of the school of thought that experience actually matters more than the titles per se. And that’s why I’m a huge fan of a lot of these high school seniors taking gap years because I think a lot of kids come out of college at 21, 22 and it’s actually very hard to transition them to the real world sometimes because they actually don’t necessarily have meaningful skills, and they haven’t spent time working and building things. That’s kind of one school of thought. But on the flip side, as a person of color, I would be lying to you if I told you that having degrees from MIT, Cornell and Hampton and having hard technical degrees didn’t help me get to where I am. And that’s a huge point of validation. And I think that the more kind of minority boxes that you check, I’m Black and I’m a female, or let’s say I was also LGBT, I feel like the more you need some of that kind of on-paper credibility because that’s sometimes what gets you access to the room.

Jamarlin Martin: Seems like the way they think about, particularly with Black professionals, they don’t see a lot of us across the table or coming in to pitch, and if you have gone to one of their schools, like a Stanford or MIT, the way the investor thinks about it is, I can de-risk my time and possibly money with the credentials. What was your thought process in deciding to go to Hampton?

Isa Watson: So there’s two parts to that. One, I come from a big Hampton family. So my father immigrated to the United States to study engineering at Hampton back in the seventies. So he was recruited from the West indies, the islands to be a part of the drumline. And so I have five siblings, so six kids in total. Four of us have degrees from Hampton.

Jamarlin Martin: A Hampton family. You guys are banging Hampton across the board.

Isa Watson: It’s a Hampton family for sure. But I would say the second part of that actually Jamarlin, is the fact that I grew up in a predominantly white neighborhood and area. So I spent middle high school in a place called Chapel Hill, North Carolina. So kind of your liberal, upper middle class educated white folk, and I felt like growing up in that environment, my schools were great, but I also felt developmentally I was not necessarily confused, but I wasn’t in tune with what it meant to be a Black woman in America. And I just felt like I needed to kind of tap into that and to kind of better understand myself, and to do that, I wanted to focus my education and my next four years and being in a safe environment where like I didn’t have all the other stuff. I wanted to be around a ton of people that looked like me, that would allow me to just focus on my academics and figure out who I was in this world. And so my experience at an HBCU was super foundational to me and my success.

Jamarlin Martin: As you know, there’s a lot of talk about diversity numbers in big tech with Google and Facebook, venture capital investing. A lot of folks are like, “Oh my gosh, Mark Zuckerberg, Google, Salesforce, it’s their fault, they need to be doing more.” Okay. We get that. That’s the popular point of view, that it’s their fault. So when I read about your background, I read about you starting to play with computers at seven, learned about computing at seven. Your father bought the components of a computer and he wanted you to build. I want you to talk about, hey, we get that Google, Facebook, Snapchat, Salesforce, Amazon, they could be doing better in terms of recruiting and making things fair, but how much is it on the culture? Just basics, parenting and culture, and what we prioritize. It’s not all external, we’re going to have to be doing things on our side. You can’t put this all on Google or Facebook’s lap.

Isa Watson: No, it’s definitely a sensitive subject. I will be the first to admit I was really fortunate to have parents that were very strict academically and with experiences. And I think that what you’re speaking about is exposure. What is the exposure that we should give our kids in our community. And so I do think that education, we talk about in the context of school, but education actually starts at home. I always joke about this because my mom was a stay-at-home-mom, for most of my childhood at least. And I had to come home, finish my homework for school and then do my homework that my mom would assign me. And it was actually much harder than the homework at school. And so I do think that communities of color and especially Black people, we should take an elevated and more direct approach to kind of creating opportunities for increased exposure within our homes, right? Especially as it pertains to STEM. But I would also say the harsh reality is that, my dad was an engineer, right. Two percent of PhDs in the biological sciences and chemistry are Black. And so when you think about us having that opportunity and that’s just playing catch up. People may not necessarily have the opportunities for exposure and there’s households like I did in mine, and I do recognize that privilege to an extent, but I would love to see progress in STEM and academic enrichment being more of a focus in the homes of the kids instead of as many video games and TV shows.

Jamarlin Martin: You would say it’s fair to say that the popular opinions and views from activists and folks that are actually doing stuff, there’s not enough of us talking about how do we remix the culture ourselves. You think that’s fair?

Isa Watson: Yeah. I think we should do that more.

Jamarlin Martin: What does this quote mean to you, from Pablo Picasso? “The meaning of life is to find your gift. The purpose of life is to give it away”. I read that you thought about that before you made a transition in your professional life.

Isa Watson: Yeah. So this was before I made a transition from corporate America where I was working all sorts of hours for someone else and for someone else’s goals and ideas to become an entrepreneur where I wanted to have impact at a much, much greater level than I would have been able to do within a large corporation. And so it was just a quote that I used to hear my dad say, right? And so I think that within each of us, there are a certain number of gifts that we’ve been given, right? And we have opportunities to nourish those gifts. And for me, I think it was a combination of STEM and analytics and a splash of being an inspirational person, according to other people, and my older sister for instance, it’s her computer science skills and I started dedication to X Y Z. And so I think that the only way that we can make this world better — we’re taking resources from the world, we should put back more into the world — is to nurture our gifts and give them back to the world in a much greater way than we were able to receive them. And so it’s just something that I think about every single day. What I do, I’m not necessarily doing it for myself, even though, I have to take care of myself and have to pay my bills and things like that, I’m really doing this for a much bigger purpose and something that’s way bigger than just me.

Jamarlin Martin: Would it be fair to say that at some point, hey, I’m working at JP Morgan. I’m working at Pfizer. I’m pursuing the American dream. I want to make a lot of money, however, you have an inflection point where it’s like, “Hey, I’m not really into this stuff is as much as I thought. I really want to use my time on earth to really impact change”.

Isa Watson: Yes.

Jamarlin Martin: Squad has raised capital. How much capital have you raised?

Isa Watson: So we just raised a $3.1 million seed round.

Jamarlin Martin: Okay. Nice. Congratulations. How many investors did you pitch to?

Isa Watson: We pitched to 32 VCs.

Jamarlin Martin: Thirty-two. Got It. And how many investors are in your cap team?

Isa Watson: From that round, it was three investors. We had offers from more.

Jamarlin Martin: How many more would you say?

Isa Watson: We had offers from more than double that?

Jamarlin Martin: Okay.

Isa Watson: But the thing about it, it’s one of those things where once you get an offer to leave than everyone else wants to come on when they had kind of shelved you for a little bit.

Jamarlin Martin: Who was your lead?

Isa Watson: Harrison Metal. They are a $70 million seed stage fund based in San Francisco. And they were the first institutional capital in brands like Heroku and Birchbox and Harry’s. And so, we have a very Silicon Valley-heavy cap table from a VC perspective.

Jamarlin Martin: And they were comfortable with you being in New York or North Carolina?

Isa Watson: No. So we’re in New York City. In fact, I just had my board meeting yesterday and my board member was actually here so they came to our offices and I go to San Francisco a lot. So between them coming to New York and me going to San Francisco, my board members, even though, like I said, most of our investors and board are in Silicon Valley, there’s a great deal of connectivity between.

Jamarlin Martin: And was there any kind of requirement or pressure like, hey, if you built a business in New York and we’re here in the Valley, we would like to see you once a quarter. Was there any guidance on that?

Isa Watson: No. And the great thing — I’m really fortunate — between Harrison Metal, that’s Michael Dearing, Precursor Ventures, that’s Charles Hudson, New Voices Fund with Richelieu Dennis. I’m very fortunate that our biggest VC investors are very supportive and very empowering, but they’re not dictators, right? They don’t impose these arbitrary rules for rules sake. And another thing too is that people say, “well, do you need to move to San Francisco, because your investors are out there?” There’s a mass exodus of talent from San Francisco right now in the Bay Area. And a lot of other markets are receiving a lot of that talent. And so New York has been a beneficiary of all the changes going on in the Bay Area, and the fact that a studio apartment is like $3,500 a month.

Jamarlin Martin: How much time did you spend practicing on your pitch, your live pitch to investors?

Isa Watson: I probably practice for a few weeks before, and practice is iterative, right? So it’s like pitching it to somebody, getting feedback, pitching it again, and there’s a lot of iterations in the deck. And so I think I did my first pitch at the beginning of February this year and we closed in mid-April.

Jamarlin Martin: Did you have friends to help you or did you hire someone possibly to help you on getting your package of your pitch?

Isa Watson: Yeah, it was combination of a few people. So my founder friends. I think that founders that have gone through this offer very useful and helpful perspectives. But also we had some kind of angel people that were just very big tech influencers and Precursor was even very instrumental in that as well. And so we had just people that were very involved with the company, both from an investment and being other founders.

Jamarlin Martin: When you targeted, it sounds like 32 firms, did you filter them based on some of their communicated values at the firm in terms of, very embracing of women, multicultural scope? How did you filter which investors to target?

Isa Watson: I actually did not really look at people’s websites too much because I find that whatever they put on their website is mostly, who cares. The firm that actually led our round probably has the least information on their website.

Jamarlin Martin: Not just websites but articles and stuff online.

Isa Watson: Not even as much. I think for me, for investors. Keep in mind, when you bring an investor on, it’s almost like getting married to somebody. You are contractually in bed with that person for at least eight to 10 years. So I was most concerned with word of mouth, how are these people, their track record, I will look at that. How many of their seed-stage companies make it to Series A, etc. But I was concerned with, “Oh, this is a really great guy”, because the reality is that Lightspeed or Sequoia or whoever may be the funder on paper, but you’re actually attached to that partner. And so I was really concerned about the diligence of the people I was taking money from, and if they were decent people, fundamentally,

Jamarlin Martin: Did you pitch to some of those big elite names in terms of Sequoia, Benchmark?

Isa Watson: Yeah. I did pitch to a few of the elite names and we did get offers from a few of the elite leader stage names to participate in the round. But here’s the thing. So what happens is that a lot of Series A, B, C stage funds. So I’ll throw the Lightspeed, I’ll throw the Sequoia, I’ll throw the Social Capital in there. What they do is they throw $100,000, $250,000 checks to a ton of C stage deals. And what happens is that when you go up for your Series A and someone looks at your cap table and they say, “Oh, Sequoia threw $250,000 in here, why didn’t they lead?” Sometimes that ends up being an impediment to raise. And so I was very adamant about not having any Series A and strictly leader stage investors on my cap table so that I can have the most objective experience going from A.

Jamarlin Martin: An entrepreneur shared with me that a white investor was asking too many questions and she didn’t like the way she was treated in the pitch meeting in terms of the amount of questions, that detail that they were asking. And she made a big fuss in this particular community that the investor was racist. The investor brought her into a meeting to pitch, but she thought that the way she was treated, an example of racism or possibly discrimination based on her gender. But what I’m seeing out there is that a lot of the Black entrepreneurs don’t know what’s smart in terms of, hey, you pitched 32 investors, some folks are out there pitching to 75, 100. It’s hard, period, right? It’s hard to get money. But a lot of entrepreneurs I believe are very quick to say, “Hey, if an investor doesn’t bite, they’re not really interested, they’re racist.” What are your thoughts to that cultural element, being in the Black tech community?

Isa Watson: I think we have to be careful about throwing the R word out there. Not that some people aren’t. And to be honest with you, I think some of it is unconscious bias. I find that there are not that many people where their intention is ill and they’re trying to be wrong. Right? And they’re trying to be unfair. And I think that it’s just a little bit more exposure that is needed. And so one of my investors, you alluded to this earlier, one of my investors told me, he said, “Listen, despite the fact that you built a billion dollar product when you were on Wall Street, despite the fact that you have really strong degrees in schools, you walk into a room and you are high risk, and it’s your job to de-risk yourself.”

Jamarlin Martin: When he says that you’re high risk. He’s just talking about in general, entrepreneurs are high risk, or are you saying there’s certain elements about you that are high risk?

Isa Watson: He’s saying me as a Black woman walking into this pitch meeting and I’m not the 22-year-old white guy who dropped out of Stanford, right?

Jamarlin Martin: Yeah.

Isa Watson: I am a chemistry major.

Jamarlin Martin: You’re not matching the pattern.

Isa Watson: I’m not matching the pattern so that in Silicon Valley standard is high risk. Right? And so I think two things. One is that it is not necessarily healthy for us to think that people are not treating us fairly, right? So I think that we should just continuously do the best that we can cause either way, if we’re bogged down and thinking that people aren’t treated fairly in the situation we probably won’t perform as well as if we didn’t have that in our head. So I think that it’s almost one of those things where it’s like, I’m not saying it doesn’t happen, but to a certain extent kind of ignore it.

Jamarlin Martin: You can become intoxicated with the stuff where you can’t be productive, you can’t have a clear head in terms of being persistent and going out there like everybody else.

Isa Watson: Right. Exactly. And so, I think the second thing is that if you get the sense that an investor is not treating you fairly, kind of say forget it and walk away because I don’t want anyone on my cap table that I don’t feel comfortable with. If someone is asking me questions because they assume that I don’t have domain expertise and they’re asking me questions in a condescending way or whatever the case is. Whatever it is that made me feel uncomfortable. That’s fine. I have the balls to get up and walk away and say, you know what, you’re not the investor for me. And I have done that to people and I have said that to people and it’s okay.

Jamarlin Martin: Was there a meeting of the 32 where you said, I don’t like how you approach that in terms of, you took it personal where you thought that sounds kind of suspect. Did you have any kind of experience with, “would they ask someone else these questions” or something like that?

Isa Watson: It was less about how they asked me questions about the product and about the problem we were solving. It was more so them through their questions implying that I didn’t necessarily fit the bill, like maybe because I didn’t study computer science or I’m a first-time founder and not a fifth-time founder with 10 exits. And so, I had a little bit of that. But to be honest with you I actually can’t even recall all the instances because I probably just ignored them and just kind of said, to hell with them.

Jamarlin Martin: What was your process to get the 32 meetings with investors? What are you doing? How are you hustling to get the meetings?

Isa Watson: Yeah. So I think it’s very iterative. One mistake I see a lot of founders making is treating this like a top of funnel exercise where they are just getting a list of all VCs possible and shooting out cold emails. The reality is that there’s an investment and ROI and networking and being able to get that warm intro to somebody because just imagine someone you know, reaches out to you and says, “Hey Jamarlin, can you take a look at this?” You’re like, okay, cool. That’s my bro since college, or whatever. But we get emails from tons of people, like dozens of hundreds of people a day, and investors do as well. And so I think that, how I approached my process, we were fortunate to actually get a ton of validation behind us from who was on our cap table, but I had to hustle to get that. So one meeting led to one meeting led to the next meeting led to this one particular person, and that one particular person introduced me to these other two people.

Jamarlin Martin: So investors were making introductions?

Isa Watson: Exactly. Investors were making introductions. But I will say the stack rank order for the best introductions is, first, founders. So if there’s a founder, let’s say General Catalyst is back and General Catalyst loves that founder, get that founder. The second is then investors. And then the third is just kind of everyone else.

Jamarlin Martin: How do you get a meeting with Charles Hudson? What was your process there?

Isa Watson: Specifically Charles Hudson is a Toigo alum. So the Toigo Foundation is a finance fellowship for minority MBA students. And Charles went to Stanford. I went to MIT, and so when I was thinking about leaving JP Morgan, I just mentioned it to the president of the Toigo Foundation and she was like, you should talk to this guy who’s a Toigo fellow. You might want to just talk to him before you quit your job. And so that was actually how I initially got in contact with Charles and I actually wasn’t even pitching to Charles. So Charles is a super great guy, but he was almost like an advisor to me and because we were both Toigo alums, and I was into this space that he was familiar with and maybe a year later he became an investor officially, now we actually have a cadence of catching up monthly, but that’s how I met him.

Jamarlin Martin: So it sounds like you had an advantage going in as a founder where you can pull the rolodex from your corporate America experience. That was, it sounds like, very instrumental.

Isa Watson: Yes and no. One of my most influential investors, I met him because there’s a guy that went to my church when I was like 10 years old that I hadn’t seen in 10 years, in North Carolina. He knew this guy from his business school. So it wasn’t just corporate America, it was people. One thing that my dad used to always say to me, he was like, “everyone can add value to your life, but also don’t be selfish about it, think about how you can add value to other people”. And I think that the world is so interconnected that there are these random ways that you can get connected to people and you have to hustle enough to kind of land those jewels and then maximize on those jewels once you land them.

Jamarlin Martin: You mentioned you built a billion dollar product on Wall Street. Can you talk about that? Because I’ve never met anybody who built a billion dollar product on Wall Street. Go ahead.

Isa Watson: So I’ll talk about what I can, because I don’t know like what is public now versus what isn’t. But I used to work in the kind of digital product management function for business banking for JP Morgan Chase. So that’s a division of the bank that banks 5 million American small businesses. And so what I was doing is I was leading an initiative, it was called Small Business Nexgen, and Jamie talked about it in his shareholder letter a few years back, and what that initiative aimed to do was at a very high level to make Chase a much easier institution for businesses to bank with. When you think about all the financial needs of a business, deposit, lending, cash management, credit lines, credit cards. So my job was leading a big digital transformation of that business to deploy a number of products and a consolidated experience for them to actually better serve the 5 million american small businesses that Chase serves. So that was the product that I was referring to.

Jamarlin Martin: What would you look back on based on experience in terms of running your company? “Hey, I wish I knew this before I got into this game as a founder and CEO.” Is there any kind of big thing over the last year or two where you had to learn it, you have to be in the mix and, “Man, I miss-priced the risk of something or industry changes.” Is there any area where you wish you would have known something before launch?

Isa Watson: I don’t think I have anything like that I can think of on the business side. But the one thing I will say is actually more on the personal side. The one thing I wish I would’ve known a little bit more is the toll that being a founder can take on you personally, and just the amount of time and effort that I invest in self-care is really critical to my performance as a founder, to my mental acuity. So I see my therapist once a week. I have a life coach that I see twice a month. I go to a meditation class two to four times a week and I also don’t do nearly as many social things as I once did. My friends circle is super tight and I talk to those three people all the time. And so I think that people think being a founder is really, really glorious thing in the public. But the reality is that it’s actually very lonely and there’s a lot of sacrifice that goes with being a founder. And so I think that was the biggest lesson that I learned in being a fulltime founder. All the other stuff, the product stuff, the pricing stuff, we’ve made a ton of mistakes and as founders you make mistakes all the time. Every week we’ve miss-priced things. We’ve made mistakes and bad calls in the product before, but that just comes with the whole territory of learning, but you should ask me this question in 10 years when I sell this for multiple billions of dollars.

Jamarlin Martin: Okay, got it. Did you choose to communicate to your investors what your exit strategy was like, “Hey, I want to sell it?”

Isa Watson: No, I didn’t because to be honest with you, I’m not even thinking about an exit. I’m thinking about building the biggest business possible today and figuring out how to accelerate our growth. Everyday that’s my focus, and so I would say out of those 32 VCs that we pitched to, maybe a quarter of them asked me about exit strategy. The other ones didn’t and also the reality is, do I want to run a public company? There’s a lot that goes with that, right? I like my independence, I like focusing on building and growing stuff. That’s my thing. But I may have a different answer for you in three years, with that round.

Jamarlin Martin: And what have been the biggest challenges with scaling it? You want to grow, you have capital, on the business side, what has been the biggest challenge in blowing up the platform?

Isa Watson: I would say the biggest challenge, there are two things. One is on product and the second is on team. So on the product side, there’s a focus that you need to have in order to scale and I think that as the product evolves, the business anyone started, from Twitter to Facebook to whatever, is not the business that it is three years or four years later. And so, the one thing that I’ll say is that we’ve had to make some tough decisions on even saying, okay, this one customer that we had that we really admired and adored and loved working with, that customer doesn’t necessarily fit with the main use case of the product, they’re doing all these edge cases and it’s distracting for the team. And so we actually have to kind of graduate that customer to an alumni, right? That’s the euphemism for it, not firing them, graduate them to alumni. And I think that, hard decisions around product and focus are really difficult with scaling because you have these two big opportunities and you’re like this one or that one, but the more you focused on A, the less you can focus on B and vice versa. So I think that’s one thing. And the second thing is team. So the team that gets you from $0 to $1 million in revenue is probably not the same team that gets you from $10 million to $100 million in revenue. And so I think that kind of understanding the inflection points of the company and the team from a talent perspective and where you need to flex up the talent and when, that’s a very difficult part of scaling and is actually really hard for CEOs, harder than you might imagine. I’ve had to have conversations with people letting them go for that exact reason, your skill set was really great for this previous phase, but now we need something different and it’s actually difficult and it’s emotional and you love these people, you respect these people. But you also have to do what’s best for the business.

Jamarlin Martin: How many cities is the Squad platform in?

Isa Watson: About a dozen cities.

Jamarlin Martin: A dozen cities. And do you need human capital on the ground when you go into a city.

Isa Watson: No, not necessarily. So there’s a ton of self-generated content on the platform, self-created content and then user content. And then we also have an integration with Eventbrite too, so we’re able to – based on your zip code – pull in different event recommendations to your various squads or communities where you are. But what I will say is that we have doubled down on focusing on New York and San Francisco. Those are our biggest markets and is where most of our kind of brain power is going right now. Making sure we kind of get those markets saturated pretty well.

Jamarlin Martin: And what are the key KPIs for the organization in terms of growth?

Isa Watson: So I would say it’s the combination of users. We have three types of users. We have your community creators. Those are the people that are creating communities. Very similar to your Meetup group creators or your Eventbrite event creators, right? And then you have your community leaders. So those are people that are liking stuff, engaging in stuff, signing up for stuff. And then you have your lurkers. So there’s a social media rule we call one-nine-ninety. One percent of your users will be creators, nine percent of your users would probably be leader slash participants and 90 percent would be lurkers. And so we actually have a much stronger creator group than that one percent and so we’re focused on amplifying that group, doubling down on that, but as far as metrics specifically, it’s user growth, but it’s also continuing to grow that creative group. And it’s also other things like number of events per community, monthly active usage, things like that.

Jamarlin Martin: Richelieu Dennis, he created a $100 million fund specifically for Black women, which is great. Some brothers have mentioned investors, they’re happy, but they’ll say, “Hey why are the funds being created gender-specific”, in terms of the Black community is not at an investment scale to start kind of fragmenting into pots. What are your thoughts on that in terms of the brothers who may have that point of view?

Isa Watson: Yeah. The brothers who have that point of view are kind of coming from a place of privilege, right? To a certain extent. But first I would say on Richelieu, he’s a phenomenal leader. He has such a strong personal story and he has these amazing women around him, his mom, his wife, women around him. So he has a very unique perspective on kind of the resources that women and Black women need to succeed in this country. And so I would actually say, I look at my business school class at MIT, I look at a lot of the people that have gotten funded in Silicon Valley, you take the top five most highly funded Black men versus top five highest funded Black women, and there is a huge discrepancy. Black men, yes, as Black people, we do have access issues, but I think that it’s more pronounced to be honest with you, with Black women. I can tell, even some investors who will see me and they don’t even know how to interact with me. They’re like, “Do I shake her hand, or do I say like, what’s up sister?” They’re so awkward. And so we’re as a result boxed out of a lot of conversations that Black men can get into easily and I don’t want to over simplify. But to the nerdy white guy who’s writing the check, the Black guy is kind of cool. They’re like, “Oh, I listen to Nas too, I bought my first Jay-Z ticket”. But the Black women don’t have that kind of coolness factor that the Black men do. And so I’ve seen firsthand the discrepancy in funding for Black men versus Black women. And the one thing I also just will add very quickly is that I was telling one of my advisors who was also on Wall Street, I said, “When I was on Wall Street, I felt like I was more Black than I was a woman.” So I identified with being Black way more than identified with women. I didn’t go to any women’s events or anything. And the reason was because my experience was more similar to that of the black men on Wall Street, the different issues that we would have. But as a founder I actually identify as being a female more than identify being Black because I see the divide of my experience being more similar to the white woman than a Black man.

Jamarlin Martin: Explain that.

Isa Watson: So really quickly, on Wall Street, a lot of the issues around promotion, credibility, lack of opportunity, white women didn’t necessarily have those issues the way that I saw my fellow brothers have that same issue on the street. But when I moved toward the VC-backed founder community, the one thing that I saw was women struggle really hard to get into the room, to get access. Whereas the black men, especially those that come from the type of schools that I came from, they had a easier time. I’m not saying they definitively have an easier time getting funded, but they had an easier time getting access.

Jamarlin Martin: What does the data say about white women getting funded and Black men? The way I’m thinking about it is that in general, the white investor or institution is gonna treat the white woman 10 times better on average with the same credentials than a black man. Do you know what the data says?

Isa Watson: I don’t know what the data says.

Jamarlin Martin: Yeah. When you say that you identified more with white women than the black man, specifically in raising VC capital, talk a little bit more about that. I’m trying to wrap my head around that.

Isa Watson: So it’s a little bit of a controversial view, I get it, but it’s just my personal experience. So when I am having more conversation, it’s just a pattern thing. Right? And so like I said, from a pattern perspective, a lot of the people that were having similar experiences to me on Wall Street were the Black men and not the white women, but from a VC perspective, a lot of the things that are said to us or kind of issues that we have to deal with. When I talked to my fellow female founders who are white, I see more similarities with their experience and mine versus that of a Black man. I’m not even gonna name any names, but there is a top three firm I know in Silicon Valley. Everyone listening knows this firm. But one of my homeboys does investments for celebrities and he was walking by the office of one of the partners with one of his friends who was a celebrity and it was like, “Oh, what’s up? Come in, have a seat.” And then next thing you know, by the end of the conversation that day, he walked out with a $9 million check that would never happen to a woman white, black, purple…

Jamarlin Martin: At that firm?

Isa Watson: At that firm. And it’s a top three firm. So my point is that a lot of these…

Jamarlin Martin: I know what firm you’re talking about.

Isa Watson: I’m not going to name no names, but a lot of these circles that are very liberal acting or whatever. They embrace the Black man way more than they embrace the Black woman.

Jamarlin Martin: With that specific firm, and they’re so late to the game in terms of having a female partner. I mean they may have 50 partners and no woman, but I believe they recently had their first female partner and they’ve been in the game for a bit. So I get…

Isa Watson: It’s not just that firm though. I see dudes cultivating deals much easier in casual forums than women are able to. And keep in mind the way that you can break bread with Bob and Lou and dap it up and drink heavily, the social aspect helps men a lot. Whereas I’m going to be buttoned up. I ain’t drinking more than a drink or two. And it is what it is and maybe they’re not as comfortable, maybe they want to dap it up with Terrence, right? But at the end of the day, there is a gender dynamic that impacts the way that deals are created in this world.

Jamarlin Martin: Your view is the comfort factor in terms of folks getting comfortable. Going back to your controversial point of view. Some people will say, hey, there’s not a lot of Black investors out there, but you have a brother in your cap table, Richelieu, you have Charles Hudson in your cap table. But when you say that raising capital you relate more with the white woman than the Black man.

Isa Watson: I want to correct you because I want this to be quoted the right way. I want to say it again for the people in the back. I said that my experience and the patterns in my experience have been more similar to women in general. And so white women happen to be the majority there, women in general than it is to men or Black men, so I don’t relate more.

Jamarlin Martin: Got it. What would you say that our people, Black people, that when we use an ambiguous diversity concept, this is about diversity. This is about, we need more diversity, we need more diversity. So everyone uses this term, diversity. However, the data is suggesting that the real beneficiaries of diversity is gonna be white women. As you know, 52 percent of white women in the United States have voted for MAGA. And in my view when our people, who have been through slavery and we have a unique history in the United States in terms of hostility, that when we use diversity promiscuously to describe a whole bunch of things is that strategically, as you know, diversity, that’s a political issue, right? There’s some groups that are going to get bigger gains than other groups. But when we use the ambiguous diversity umbrella, Black people in America, we end up losing because we don’t have the diversity to power as white women. And so when we are banging and championing diversity, when everything is kind of process on the back end, it’s really, you’re pushing…

Isa Watson: Who is championing diversity? Are you saying that because of the new voices phone?

Jamarlin Martin: No, no, nothing related to Richelieu. I think it’s Black. Like he’s not saying this is a diversity. He’s saying “I’m calling it out”, and I love that. What I’m seeing is that I can put 10 diversity activists, they could be investors, activists, executives and say, “Hey, I want to promote diversity”. But when they say that, I feel like it’s really pushing, unintentionally, an agenda for the advancement of white women just based on how we’re structured here in the United States.

Isa Watson: So I think that it really depends on the environment. Right? I had this conversation super openly with executives at my old firms, and this is one of the reasons I did not have similar patterns of experience to white women when I was in corporate America, was because when diversity programs were implemented, specifically women’s programs were implemented, the box was checked and all of their goals were achieved without the inclusion of any other women, but the white women. And so I never felt that the women conversation included me. I never felt that it did. And I think that’s also a part of why my experience was not similar to that of the white women in corporate America, but I think it’s a little different in the VC founder world. I don’t hear the diversity conversation talked about in the same type of way. I think it’s really more about objectively looking at access, right? And who has the greatest level of access, and I will say that Black women definitely have the lowest level of access.

Jamarlin Martin: So Black women, it sounds like, could be hurt the most if we spend energy arguing for everybody, all the different groups in diversity, it doesn’t matter if you’re rich, poor, whatever. We’re arguing for a broad diversity. But based on the gender and racial dynamics here in the United States, it seems like the Black woman would lose the most in terms of if we don’t call out what needs to happen for Black people in general or Black women specifically.

Isa Watson: Right. Didn’t Malcolm X say something like that? It’s like the most disrespected and underrated person in the U.S. is the Black woman.

Jamarlin Martin: And so for the audience, I definitely believe that we have to be careful in using diversity in an ambiguous way. And if we’re really talking about lifting our people up, that it’s okay to be specific. The problem is specific. And so let’s go back to Richelieu Dennis. So he sells a part of his company to Bain Capital, and that’s the thing that folks need to be aware of, that you don’t have to sell your whole company. I think Richelieu did something very smart where he sold a chunk of his company to tap liquidity. He used capital with the partner bank capital and then he sold it. So there was two sales with his process. And so when I see certain things in the media, it’s like white people, they’re passionate about diversity. They want to see more Black founders get capital, and so it starts to take on a smell that white folks are in the diversity tech scene, saving people, right? We want to go and help the situation. And so you don’t see as much of our people coming in with big wallets, big checks, organization, to save ourselves. And so why I think Richelieu’s new fund is so important is I believe that we have to own our rise for the most part. Do you share that point of view?

Isa Watson: Definitely. Definitely. Richelieu, besides being an amazing person and believer in the Black community and what we contribute to this world, I think Richelieu also saw a huge problem with access, the fact that Black women just have a much harder time getting into these rooms, getting access to funders. And so I’m glad he is pounding his fist against the table. But the one thing I will also say about white people in particular is that I have found in my experience, again, just my experience, that the white people that are the most pro diversity are the ones who are not that loud about it. There are a lot of people that are always talking about it. They’re tweeting about it, making money from it. But where are your checks? And I think about three of my backers in particular, one just sold his company for $2 million and he just writes me checks. He was just writing me checks, and he’s written more checks for Black women than any other of the white people that are loud about it. Second one was an early employee at Netscape. Another one was an early employee at Intuit. And I’m not the only Black woman that they’ve supported and these are very Silicon Valley tech guys. And so I would say on that side, people should be cognisant of who’s attracting. Don’t be attracted to all the noise, follow the dollars. On Richelieu’s side too, we do need people in our community like Rich. And what Rich says to us, his founders, is Rich says, “listen, this isn’t like a one-stop shop type of thing”. You go and become multi-millionaires, multi-billionaires. And that you do for other people what I’m doing for you. He’s trying to kick off that cycle, which I think is just super commendable.

Jamarlin Martin: Where can people find you online?

Isa Watson: So I am most active on Twitter and Instagram, and I am @isadwatson. So those are both my IG and my Twitter handles.

Jamarlin Martin: Thanks for coming on the show. Let’s GHOGH!

Isa Watson: Thank you for having me.

Jamarlin Martin: Thanks everybody for listening to GHOGH. You can check me out at Jamarlin Martin on Twitter and also come check us out at Moguldom.com. That’s M O G U L D O M.com. Be sure to subscribe to our daily newsletter. You can get the latest information on crypto, tech, economic empowerment and politics. Let’s GHOGH!