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The Dirt: Diversifying the Boston tech sector with Smarter in the City


smarter in the city

The statistics for minorities in technology and entrepreneurship are underwhelming to put it mildly.

  • 9.2% of tech industry employees are Latinx and African Americans
  • 0.2% of venture funding goes to black females
  • 20% of firms with paid employees are owned by minorities
  • The average net worth of blacks in Boston is $8

Enter Smarter in the City, which was created as a way to diversify Boston’s tech sector by reaching out to entrepreneurs with less traditional backgrounds from less traditional neighborhoods in Boston. The organization believes that supporting a diverse ecosystem of entrepreneurs makes the startup community better while also allowing mentors to go back into their communities and improve diversity in their own organizations. Since their founding in 2014, they have helped launch 20 startups led by underrepresented entrepreneurs.

In this episode, I spoke with Smarter in the City mentor and board member Tim Buntel. Tim was one of our earliest Product Heroes, but in this interview we focused on the work they are doing at Smarter in the City to increase diversity in the Boston tech scene, including:

  • Why product managers sometimes make the best mentors
  • Why we should care about diversity in tech sector and entrepreneurship
  • How to get involved in Smarter in the City as a mentor or an applicant

Learn more about Smarter in the City on their website.

Listen to the show

Show notes


Heath: Tim, you actually were one of our first product heroes. It was summer a year ago.

Tim: Okay.

Heath: And so we’re trying to make the rounds and reaching out to our product heroes and say, Hey, I’d love to have you back in to talk about something else. Could be an update to what we talked about at the time or could be something totally new that you’re really excited about or working on and so we decided to have you come back today and maybe we’ll just start off by having you describe what is a typical day in your role as VP of XebiaLabs? What’s it like?

Tim: XebiaLabs, we’re a DevOps software company creating tools that enterprises use for DevOps initiative, so it’s pretty typical types of challenges that most product managers face, right? So, we spend a lot of time on focus and prioritization. Figuring out what are the most important problems for us to solve? In what sequence should we solve those problems? This happens through meetings with other PM’s on the team, so I lead the team of product managers and UX folks. There’s lots of conversations with internal stakeholders, customers and their proxies and it tends about the typical things, how do we solve problems in a way that’s gonna impact the market, delight our users through user research, user experience, UI design and that sorta thing.

I spend a lot of time on visibility of what we’re doing, both internally and externally, from helping the company understand what we’re doing and why is the internal piece of that.

That’s within the executive team, but broadly everyone in the company needs to understand what we’re doing. We invest a lot in communicating that through newsletters and town hall meetings and those sorts of things. Also, externally, right? We have to make sure that the market understands what we’re doing and why. That’s PR, analyst relations, events, we do a lot of customer outreach in real life and webinars. Just last night and the night before we did a viewing party at the office for the 24 hour DevOps conference, which is a great event. This was a virtual, online, 24 hour conference on DevOps, so we hosted a track there and that’s another way we kinda do the outreach-

Heath: So the whole thing was virtual?

Tim: Yeah, so it was entirely online, done with YouTube live channels and Google Hangouts. I was a moderator, I was sort of managing, bringing the speakers in. I would turn it over to them, they would give their presentation and demos and slides. Just like you would in any normal conference. Then we had dedicated slack channels for the participants to interact with the speakers afterwards, and it ran for a full 24 hours across-

Heath: Wow-

Tim: Five tracks, I think?

Heath: Okay.

Tim: I had never done a virtual conference like that before. Done lots of real life conferences, but we ended up with over 33,000 people registering for that event worldwide.

Heath: Wow.

Tim: It is a great way to amplify the reach of the message and DevOps certainly is a hot topic. I spent a lot of time doing that. That’s a kind of corporate visibility about what we’re doing and why. In the more leadership side of things I spend a lot of time with alignment. Making sure that the organization is moving towards the same goals, so that we’re not pointing in different directions when it comes to sales and support and engineering. Then finally the team. I originally joined XebiaLabs to build a product organization within the company. That has continued to be a large part of what I do. That’s everything from hiring to mentoring, to knowledge sharing, bringing the teams together. Both in person … We do have a geographically distributed team in a couple of different cities, so bringing them together to have professional social interactions and that sorta thing.

Kind of typical, larger enterprise product organization types of challenges.

Heath: You’ve been a mentor and a board member for Smarter In The City for over three and a half years. Tell me about that organization, what it does and what’s your role?

Tim: Yeah, this is great. This is one of my deepest passions. It’s a great project, and I’m so proud of it. Smarter In The City started a few years ago down in the Dudley Square neighborhood of Boston, which is in the kind of the socially challenged parts of the city. It hasn’t been that Dorchester, Mattapan, Roxbury area has been left out of a lot of a lot of the economic opportunity that’s happened in the city.

So, the idea of Smarter In The City was to look at ways that we could diversify Boston’s tech sector, by reaching out to entrepreneurs who were interested in doing technology start ups that would be coming from those less traditional backgrounds and those less traditional neighborhoods. Supporting local minority run businesses. How we do that is sort of a pretty traditional accelerator program, so we … Couple of times a year have a cohort of on average five or six start ups that we provide the typical set of services. We have office space that they can use, we have mentor matching, we have competitions where they can earn cash, we have legal support and all those sorts of things, but really the focus is on tackling some of those diversity issues and bringing entrepreneurs into Boston’s tech scene who may not have otherwise had an opportunity to be there.

Heath: What is it about product managers that you think make the best mentors for startups?

Tim: I feel that the most important thing in an early stage startup is getting that product market fit. Understanding who your customer is, what you can do for them and that’s the kind of thing that product managers live and breathe every day. Product managers know how to ask the tough questions that an entrepreneur would need to answer to make sure that they’ve achieved that right kind of product market fit. I also think that product managers have a great skill and background in data centric ways of answering those questions. Being able to go out and use qualitative abilities, like customer interviews or quantitative activities like surveys and those disciplines are really important in those early stage start ups to make sure that the entrepreneurs are finding the right evidence to make the case for their business before they go and invest in building a product and that’s what we most often see.

We’ll have folks who are very eager to solve a problem. Their heart is in the right place but they simply haven’t done the homework on the market. I think product managers, they have those skills already and can share them with entrepreneurs in a way that makes them much more successful early on.

Heath: Product managers themselves seem to be a group that is very into reaching out to one another, learning from one another, sharing? I don’t know if it’s because there is no formal … I’ve heard it many times over, there’s no formal product management school or training. There is no major for product management, so how do you learn? You find a product manager and you follow them around like a puppy dog kind of thing and so it feels to me that, that role just always seems to naturally gravitate toward learning from within?

Tim: Right and I would also offer that I think it’s a great benefit to the product managers too, to take that entrepreneurial mindset back into their jobs, right? Especially folks who are in a more established corporate environment maybe, to spend some time with people who are taking this entrepreneurial approach to a fresh problem. That can remind product managers that they should be doing that in regardless of what their products are, right? You should strive to be an innovation driven enterprise, whether you have zero customers or 10,000 customers.

By mixing established product people with new entrepreneurs you get a great cross pollination. It’s an experience for both.

Heath: That’s the prototypical … Those who seem to volunteer and give more of their time get an equal amount out of it, whether it’s just reminding them what they love so much about what they do or reminding them that, Hey, I’m sitting here, and I’m giving this advice. I need to follow what I say. Because I think whether it’s innovation or some of these customers facing activities, product managers often are challenged to protect that time spent on innovative activities looking forward planning and what have you and no better way to remind yourself than saying to someone else, Hey, you need to do this, that and the other.

Heath: What do you think someone should look for in a mentor?

Tim: Yeah, so we provide a number of different mentoring opportunities. Precisely because different people have different skills and they have different ways of offering that to the companies that go through our program or the entrepreneurs. Some folks come in and just provide a workshop. If you have an area of expertise that you wanna share, we’ve had folks come in that have given assistance on how do you give a good pitch? Or what are some revenue models that might be interesting for a new business? Those can be done in a one off sort of way. We have some folks who come in and offer sort of office hours. If, you have an expertise in legal or financial or product or engineering, you can just make yourself available for ad hoc conversations, but the most valuable relationships are those ongoing mentoring relationships, where we find someone who, either based on their background or based on the skills that are represented in the startup.

A lack of a certain skill? Where we can partner a mentor who is gonna go with that company through the entire six months or five or six months while they’re in the program. What we look for there, is partially skill based. If we have a start up that lacks a technical co-founder for example, we might partner them with someone who has a more technical background, who can guide them through figuring out how to get the technical pieces of their business off the ground. For example, we were talking about product folks, if you have someone who still needs a lot of validation, we might partner them with someone who has a strong background in that sort of work and also we look to the mixture and diversity of the teams as well. A big part of what Smarter In The City is trying to do is diversify the tech sector. We also wanna make sure we have a diverse participation in all of those teams as well.

We wanna make sure that, that’s a mix of ages and genders and races and different economic backgrounds, because the more of those voices are present in the conversation, the better the outcomes are gonna be. All right, so, if we have certain minority entrepreneurs and they’re only working with close colleagues in their same age or, sort of background, they’re gonna lack some of that diversity that you can get by mixing mentors. We like to keep the mentor base diverse as well.

Heath: As far as criteria for Smarter In The City, is it geographic? You mentioned those towns in the Boston areas, is it a particular ethnicity, gender, socioeconomic? How do people gravitate towards Smarter In The City versus some of the others that are out there?

Tim: The focus is really on Dudley Square and that part of the city. We are open to lots of different kinds of entrepreneurs. We have had young, we have had old, we’ve had men, we’ve had women, lots of different backgrounds. Really what we’re trying to do is find voices who are typically not represented in the usual places. This is something that lots of organizations are doing. Mass Challenges worked really hard to diversify their participants base and so forth. I also find one of the side benefits of that is that you start to explore problems that are less expected as well, right? Often when we have entrepreneurs who are coming from different backgrounds or from different kinds of neighborhoods, they tend to solve the problems that they have experienced in those communities in those neighborhoods and those may be different kinds of problems than the typical entrepreneur in Kendall Square in Cambridge or in the Seaport District might be solving.

We love to see that as well. We like to see folks who are drawing on their own diverse backgrounds and experience in the business ideas that they bring to the table. We’ll see lots of startups that focus on things like health and nutrition, which is a big problem in some of these neighborhoods or economic opportunity. We wanna find ways that the entrepreneurship can have financial economic impact on those neighborhoods as well. You diversify the entrepreneur base, you also end up solving problems that otherwise may go unsolved.

Heath: Why should we care about diversity as it relates specifically to entrepreneurship and technology? What’s the value of diversity for the companies themselves or for their users, what have you?

Tim: Yes, so it’s really that notion that the more voices you have present in a conversation, the richer the outcomes are gonna be. We know that from all of our experience that different perspectives have the ability to solve problems in more creative ways and by staying within a really tightly defined group, you’re gonna miss that opportunity to solve problems and come at them from unusual angles, right? We believe that supporting a diverse ecosystem of entrepreneurs is gonna make the startup community better, but it also allows our mentors to go back into their communities and improve the diversity in their own organizations as well. We have one of our early companies in the beginning of Smarter In The City was called Tech Connection. Melissa James was the founder and CEO of that organization. She’s gone on to be wildly successful, helping to bring diversity candidates into large corporations that are seeking to diversify their technical workforce.

And that’s another great example of it’s not just the start ups in these communities, but it’s really helping bring that message of diversity to the broader Boston tech scene.

Heath: How do we increase diversity? Is it about opportunity? Is it about financial? What are the ways that we’re attacking that problem?

Tim: I think the most important first step is to decide that it’s important. We have to have these conversations within every organization. Discuss it and recognize the fact that the tech community generally doesn’t reflect the kind of wonderful variety of people in our community. Once we’ve decided that, that’s important to us I think you’ll find that it begins to happen naturally, because you start to seek out those other voices. Sometimes they’re right in front of you and you don’t even know it. We have another organization in Smarter In The City current cohort called Project 99, that’s looking to do just this, where they’re trying to give support to employees from diverse backgrounds, typically younger, so millennial minority employees at larger corporations to give them the support that they need to be successful in those organizations. In many cases we find that opportunity for diversity is already there if you just look after it.

You can make a plan to seek out that untapped talent, if you don’t already have it. Somebody like Melissa with Tech Connection can help find those sources of untapped talent and then finally get involved. Smarter In The City is always looking for folks who wanna donate time or money or expertise to a community and we’re not the only one of course. There’s lots of other great organizations in Boston and beyond that are always looking for volunteers, mentors, donors and so forth, right?

Heath: It’s funny, I admit I chuckled a little when you identified millennials as a segment that was in need of this diversification and focus and everyone seems to like their hammer on millennials, but they have problems and needs, too.

Tim: Yeah and you know what I think what we’re seeing is a lot of … We’re seeing some of the focus that’s been happening in the last decade or so and diversity is starting to bear fruit. We’ve been, not enough yet, but we have been investing in a lot of STEM training for girls and for other folks who are not traditionally open to those kinds of opportunities and I think now we’re just starting to get to the point where some of those early investments are paying off and you’re getting more folks into the workforce coming from that background, but when they arrive there they’re finding that they’re in the presence of a giant organization that historically hadn’t been very diverse. Project 99 and others are trying to tackle that problem by saying, Hey, let’s make sure that as these young more diverse people who are coming into these different fields and professions, that they have the support from peers and from others to make sure that they’re really successful. We wouldn’t wanna do that great investment of diversifying the workforce and then having those people struggle and potentially fail when they get there.

Heath: And let’s face it, they are the future worker, customer, user and so not unlike if you make products that are to be used or expected to be used by women and you have no women on your team, how do expect to serve the needs of those future potential customers.

Tim: Exactly. Exactly, if you go to the typical product meet up and it’s all a bunch of 30 or 40 something white guys, that really doesn’t speak to the diversity of the user community and again, it misses opportunities. As entrepreneurs and I would include in that investors as well, you’re looking for these big high impact problems that you can solve and if you’re only dealing with the problem space that you’re aware of, you’re missing out on a huge piece of opportunity.

Heath: Yeah. By keeping your team diverse, your understanding of the breath of problems you can tackle is much wider. Therefore, there’s more opportunity there for everybody. We’ve got these programs like Smarter In The City, tech diversity, resilient coders, what we’re doing here is diversifying and finding untapped talent. Another similar example, one of my wife’s former colleagues, she founded a company that was based on matching companies that needed skills with moms who … They don’t wanna go back full-time. For whatever reason. Can you imagine the amount of just pure, raw talent that no one cared to think of, because there was no real way to tap into that and when you bring that up it’s like a, Duh. They didn’t just magically forget everything when they had a child.

It’s just that they don’t wanna come back full-time and by choosing not to go into these diverse areas or not to tap into a segment, you’re just choosing not to win really.

Tim: And ironic that at the same time you hear so many people complain how hard it is to find great talent.

Heath: Right.

Tim: You’re like, Oh, the talent’s there, you just have to be willing to find it.

Heath: Exactly-

Tim: And you have to be willing to, in some cases, give a little bit of extra support to understand that the initial experience any way for some folks who are joining an organization with a less traditional background or pathway into that role, they might need a little bit more help at the beginning, but, boy the payoff in the long-term, both for the employee, as well as for the organization is gonna be really dramatic.

Heath: Feels like we’re making inroads and certainly, if you consider a metric being the number of organizations that are focused on diversity, both from the upfront investment arm and the actual companies themselves, but how do you think we collectively are doing here?

Tim: I mean the numbers are still really stark I think. From Smarter In The City, we shared some of the statistics in some of our grant proposals and it’s still really shocking. It’s less than 10% of tech industry employees. Our African American or Latino Latinas, the one that shocked me the most was venture funding? The amount of venture funding of the total that goes to black females is 0.2%. W have just so far to go. I think it’s great that there is a lot of awareness of it, but we need to make sure that every single company and organization, as we said before, starts by having this conversation and says, What can we do to improve what we’re doing to make our workforce more diverse, so that we can reap those benefits. Right?

Heath: Yeah.

Tim: And I think if every organization has that conversation and at the same time reaches out and supports efforts like Smarter In The City, like resilient coders, like code squad, right? Then I think you’re gonna see those both improve at the same time. Companies will find themselves of reaping the benefits of a more diverse workforce and all of these organizations will flourish. It’s tough to be a non-profit these days, too. While it’s good that we have all of these groups out here, that are trying to solve this problem, remember that they’re non-profits and that means we have to support them as an industry that is making a lot of profit. We need to be paying back to help support this at the same time.

Heath: You’ve been here three and a half years, did you wanna talk about any of the former or current cohort classes that you’ve been through. Some of the more interesting ideas?

Tim: Yeah, there’s been great ones over the years, the SmarterinTheCity.Com website we have a great portfolio and you can see some videos. We did just kick off our new cohort a couple of weeks ago and I’m really excited about some of the companies there, we have one company called Food For All, which is looking at reducing food waste by providing what they call affordable leftovers, so it gives you an opportunity to use an app to find last minute food before a restaurant closes that the restaurant will sell you at a discount to avoid having to throw it out. It’s a great way for people who wanna save a few bucks on dinner and who maybe wanna try a restaurant that they may not have gone to otherwise. Really interesting match of solving kind of a social problem, which is the huge amount of food waste in this country and also a great marketing opportunity for restaurants. We have a company with an app black conservator, which is sort of a news and information aggregator, specifically for stories on black lives and sports and entertainments, sort of pulling all that all in one place.

It’s amazing to realize that, that’s absent in the video landscape today. Lots of organizations produce information that’s interesting to that market, but nobody pulls it all together. Black conservator is doing that, it’s a great thing. Project 99 I mentioned before, which is helping organizations engage and retain their diverse talent. We have a company called Espartudo, which is a media company, specifically looking at the sports market in Latin American, non English speaking countries. Bringing the power of that huge fan base to a media approach. And Safe Point, this is an interesting, small startup, that’s looking at conference attendance and the high cost of getting a hotel room if you go to a conference or a convention, so it helps people pair up and share a room together at an event. Started, some young founders who were into the kind of Comic-Con and that scene and they found it hard to find people that they could share the expense with, so they built this themselves and are going out and starting to make great partnership with an organization.

Help the young folks, who might not have as much money to stay at expensive, awesome hotels, so those are some of the current cohort and again, over the years we’ve had dozens of others. Melissa in the Tech Connection is a great success. We had a company called Scholar Jet. In the last year’s cohort and they’ve been tremendously successful. They have invented what they call action based scholarships to help pay for college funding, so instead of just writing an essay that says, Why you should give me my money for a scholarship. The student pledges to perform some activity. Maybe they say they are going to train for a marathon and by achieving that accomplishment, then that qualifies them for the scholarship, so it could be a social activity, or it could be a physical activity or it could be a work experience.

It’s tying scholarships to activities and doing things instead of just kind of being stuck in your head and asking for money. Beauty Link was another recent company cohort before last, which is a great example of looking at the community and so there’s lots of independent beauty professionals, hair and nails and that sort of thing, but the system for renting chairs in salons is pretty disadvantageous to the beauty professional, so Beauty Link was looking to disrupt that by allowing the professionals to bring that service to people’s homes or to hotel rooms or to events or that sort of thing. It was a way to open up more economic opportunity for those folks who are depending on that as their livelihood. That to me was a great example of an entrepreneur who was gonna build a great, viable business, but also solving a real problem for the folks that are in that community. And now I know if I went to most meet up sessions in Kendall Square on a given night, understanding the dynamics of that chair leasing and kind of system that they have, most people wouldn’t have heard about that.

You really need to understand that to solve that problem.

Heath: It seems like a lot of these companies and cohorts, almost out of the box, come with a real problem that’s been identified, versus in the other direction, so many times you find yourself sifting through the proverbial elevator pitch, trying to determine, Okay, what’s the problem? I get it, cool, neat, what’s the … Is it a product in search of a problem?

Tim: Exactly-

Heath: Versus, Ah that’s a problem, what’s the product or the service?

Tim: Yeah and I find that so much when we have technical founders, right? Often in the, I’ll call it the traditional entrepreneurial scene or kind of start up world, you often have technical founders and they invent something that’s really clever and it’s a smart piece of technology. Then they go out and try to find the problem that it solves. Or they have some sort of vague understanding of the space, whereas the entrepreneurs that we tend to deal with, they are often less technical. Although we certainly do have some technical co-founders, but they’re really coming from experiencing a problem. Either in their community or in their own lives, so they have that domain experience. They have that domain expertise. They viscerally understand the problem and they just need that encouragement to build a business to solve it, because they haven’t necessarily been told in the same way that many other folks have, Well, if you see a problem, go solve it. If, you see a problem go solve it. We have that hammered into our heads in many areas, but a lot of the folks, the entrepreneurs that we deal with hadn’t had that.

They need the encouragement and the mentorship, but they really get the problem and they can solve it in a much more exciting way.

Heath: And are these annual cohorts?

Tim: We tend to go about six months. Five or six months, although we have had a couple of companies who have gone through the structured program and then have stayed on to further incubate the business and keep it going. We do have a kind of a fixed structure to the program, where we start with ideation and validation, then we go through building MVPs and then we go to pitching and fundraising, these sorts of things that are organized around events and it culminates with a pitch competition that we have cash prizes for those companies as well. That usual program is five or six months, but if the companies are doing well and they need a little bit more help and a little bit longer to incubate, we certainly have the flexibility to do that, too.

Heath: How many participants, companies, entrepreneurs per cohort? It just depends on?

Tim: Yeah, the average has been five or six. Some years it’s been a little bit more, some years it’s been a little bit fewer. We’re really fortunate now that the word about the program has started to get out, so the quality of the startups has gone up and up and up every application period, so that’s good and bad. It means that there’s more great entrepreneurs that we can service, but we are limited, not just by resources, how many we can support, so we are exploring other ways that we can partner with Roxbury Innovation Center and other organizations that are trying to serve similar kinds of missions, how we can partner together to amplify or impact beyond just the few that we can do.

Heath: Obviously you have a website they can go to, but give me a sense of how does one even begin to get started with Smarter In The City?

Tim: Sure, for Smarter In The City, visit the website and there’s a form that you can fill out there if you’re interested in becoming a mentor or folks can always shoot me an email or Tweet I’m sure you can post that with the Podcast here.

Heath: Yeah.

Tim: We’re open to lots of people joining at any given time, but don’t forget Smarter In The City, while it’s a personal passion of mine, we’re only one of the many great organizations in the city, so if this is something that anyone listening is interested in and I hope you all are, just go out and go to a meet up, go to a pitch night, go to a competition and find some of the organizations that are doing this kind of work and we’re always looking for people that have an interest in doing that and would always welcome people help.

Heath: Well, great. Thanks a lot for coming.

Tim: Great, thanks for having me.

Heath: Alright.

Tim: It’s been a fun conversation.

Author Heath Umbach

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