In this episode, Rob and Josef talk about the impending paradigm shift represented by the metaverse, and relate it to past shifts.

They speak with Joe Sriver, the first UX/UI hire at Google, founder of the cellphone flashlight function, and CEO of 4giving. Joe talks about the importance of being data-driven as an early employee at Google, and as a founder at one of the first app store developers, DoApp. 

Who does Joe Sriver see executing? Pipe


Welcome to the execution is King podcast where we talk to successful startup founders, investors and ecosystem builders to cover insights and best practices for the next generation of great global startups. Today, we’re going to be talking with Joe Shriver, CEO of forgiving. So Rob, Facebook recently rebranded as meta, and everybody is talking about the metaverse, and not a lot of people quite know what it is yet. But we kind of sense that something bigs happening like there’s this big paradigm shift, what was your experience, like in previous big shifts like this? So paradigm

shifts are really interesting. And with Joe, on our podcast today, you know, we both went through a couple of these. And you know, one of those was kind of the initial advent of the internet in the 90s and early 2000s. Him at Google, and then his own startup do app for the iPhone. You know, for me, it was kind of publishing my own websites. And then kind of within the business that we had created launching a business on for iPhone and Android in the early 2009 2010. But, you know, it’s interesting, when you’re designing a startup, or you’re thinking about a startups kind of strategy and roadmap, when you have these paradigm shifts with new platforms, you have to think about what’s the killer app going to be for startups that are going to compete with me in my vertical. And there’s all these kind of first mover advantages in terms of network effects or switching costs. So you really want to think that through early, because the that first mover advantage can be can be hard to unseat. And we’re in and I think about that, like, you know, it’s actually been 13 years since the iPhone shipped, I think it was 2008. And here we are in 2021. And we still it still feels very much like for mobile compute. We’re still like in the second or third inning, there’s still people dreaming up, you know, a new mobile app kind of first use cases that are completely dominating verticals. And so and I think we’re still like in the early innings of the mobile compute. But now we’re probably, you know, 234 years out from the, you know, this new Metaverse world. And, you know, imagine what the world is gonna look like, when we have a billion users walking around with smart glasses over their, over their eyes, in leveraging, particularly, I think the augmented reality use cases. So I think that’s, it’s just really interesting to think about. And I think, you know, the real pioneers that jump on these paradigm shifts early, there’s many examples of them who sort of roll that those waves to just multi billion dollar kind of outcome, Joe talks about what it was like going from designing web experience at Google. And the interface is to, you know, simplifying things for a small mobile screen and the importance of simplicity and data, and really both those examples, but especially in a small screen factor. You know, imagine that, for what’s needed for a full three dimensional context to wear glasses experience, I have no doubt that there’s gonna be like a whole different breed of applications that are like things we’ve never even seen before. Joe, for starters, can you tell us a little bit about your background kind of through your career and just introduce yourself for our listeners today?

Sure, yeah. Thanks a lot for giving me this opportunity. Appreciate it, Rob. So I began my career. After college at at IBM before college, I was fortunate to work as an intern at Intel Corporation, that kind of gave me a path for my future career. So I was at IBM for about three and a half years. And in Rochester, Minnesota, it’s down south from the Twin Cities. Then I was fortunate to move on to Google as their first UI UX employee. And that was in I was hired in 2007 2001. It was there for about five years. Then I moved back to the cities and started a company with a couple of guys that I knew from my days back at IBM is called do app. And we were fortunate to be at the forefront of when the mobile technology started taking off with the iPhone and Android devices. We had kind of three companies within do app. And we were fortunate to have three exits through do app. After after do app. Then I met a guy down in Rochester, that was working on a fundraising software platform. And actually during do app, I had some ideas around the fundraising space. So this guy had some stuff going on already. I joined him and that company is called forgiving them at forgiving right now. And we’re having a great time.

You were the first UI UX hire at Google. I mean, I I envisioned you walking into the garage, but I suppose there’s a few more employees than that at that point.

I always think of that. So the group I was at at IBM obviously IBM is a huge company. and still is, the group I was at IBM had about 200 people. And so then at the time, when I joined Google, they were just under 200 people. So I thought, Oh, it’s just, you know, kind of a lateral move, you know, to another group of 200 people. But by the time I left Google, it was, I think, was probably about 10,000 people. And I have no idea what they’re at now. But at the time, I didn’t think it was the early days. But now looking back, it was the early days of Google. And so it was exciting just to be part of that. I know,

we’ve known each other for a few years, Joe, and as an entrepreneur has been building software companies, since I was 15, like, you know, 25 years or whatever, I think maybe a lot of entrepreneurs and feel like myself, where it’s just like you dream of creating a company, you know, to the scale of a Google or an Amazon or an Uber. And you guys, quite frankly, I think it’s really interesting, because so few people will ever get a chance in their lifetime, to have that kind of an experience. I mean, there’s just not that many companies that are the most valuable in the world that are getting started. So would love to learn more about, you know, some of the takeaways,

one of the big takeaways from my experience at Google was just their focus on collecting data and making decisions from from the data that they’re collecting. And that was one thing that I’ll be honest, I didn’t really think about too much before I got to Google, like, for my Intel, or IBM days, but they were beginning to that. And it got that kind of semi course for for future endeavors at do app as well as forgiving. I mean, having data drive, the decisions that we make, one of the projects that Google I was involved with, was just the look and feel of how ads appear on the search results page. And now they’ve kind of gone away from the ad look and feel still somewhat similar these days. But they used to have ads on the side of the page, those were what I was responsible for kind of designing the look and feel. And just, it was just always interesting to see small changes, like you know, bolding text, or putting a line here or horizontal rule there, or just the color of the background or the size of the font, just how much of a massive change that would create as far as revenue coming in, they would do these experiments, they call them 5% experiments where they just took about 5% of their traffic. And they would put them through this kind of experimental UI route, when they’re searching pages. At the time you 5% was still a large number of folks that were going through the pages centrism, to see how just these A B tests that would that we did back in the day, how much of a change, you know, just like I said, little things in bold in text, you know, putting a horizontal rule here or there would change the click through rate. I forget the exact numbers. But then I mean, it was like millions of dollars, you know, more revenue on a daily basis that they’d be getting just with these little changes. So and that kind of, like I said, Said, set the course to look at data and do app as well as forgiving. We may not have the amount of users and people I think those those experiments, and a B testing is still really important. So you

end up going from from Google, in one have known at the time, of course, but went on to become the one of the most valuable companies in the world. And then you leave and you go found your own startup in do app, what was going through your mind at that time when you decided to leave Google? And what was sort of the original idea and plan for

sure. So so after Google, I was kind of in the heart of technology in Silicon Valley. So I came back to Minnesota, I thought maybe I was kind of on my own as far as tech startups and startups in general. But I still kind of like that, that startup feel and entrepreneurship. So in about, I think, to the end of 2006 or so I started a company at the time was called Page Powell. And it was a focus on just widgets like back then with with blogs and stuff, there’s like, you know, little widgets that you put on, like your blog to, you know, tell whether our stock boats, but I was actually working with a group of developers in Hopkins, Minnesota got to the point where I thought maybe I should bring this in, in house, I tap my buddies that I met down in Rochester back in my IBM days, Wade beavers, and Dave worrilow. And said, hey, you know, we talked about different bunch of different ideas when back in the late 90s. And are you at a point in your career to, to jump ship and join me on this startup? Right. And unfortunately, they were they were excited. So waiting, Dave came on board and, and wait, and David had some experience on mobile stuff that they were doing for for IBM, I think on BlackBerry or the mobile technology of the day, then in the late 2000s. And they said, Well, you know, we’ve been experimenting with mobile at IBM. And I think that’s that’s the future and fortunately, around that time, I think it was I think it was in July of oh seven or interval seven word the iPhone came out or debuted. And then in oh eight, spring of all ages when the App Store debuted, or maybe in July of oh eight I’d have to look back Anyway, so we were fortunate at do app, we kind of jumped ship from the widgets. I forget the numbers. But I think the initial developer pool for the App Store was maybe 500 people, or 500. Developers. And we thought, you know, being in Minnesota, we have never had a chance. But fortunately, Apple picked us. And we had exceeded three of the first, either 500, or three of the first 1000 apps so that we were very fortunate. And actually, one of the apps that we had was a flashlight app that because it was my old flip phone that I used to search around with, had my phone on to search around for stuff in the dark. And I thought why it’s good to have a white screen on the iPhone and make it into a flashlight. And so actually, that app during the course of do app was actually probably one of our most popular outfits. Even after they they had that flashlight on the back with the flash on the camera. People were still downloading the the highlight app, as we call it. Actually, at the beginning, we had a slew of apps and a bunch of different verticals. We had some game apps, we had some utility apps, like the highlights and some other random apps. And so Wade had the foresight to kind of start focusing, we had a contact at WCC o in town here. And we’re able to do a news app for them. So we that got us kind to the news and media app. Dave had some experience in real estate. So we start down a real estate vertical. Being that basically half our team was in Rochester, Minnesota, they had some contacts at Mayo. So then we had some medical and vertical. So we were essentially planted in three different verticals, medical, real estate and media. And eventually, we found a way to exit all those verticals. So the first was the medical vertical. That was a deal that we had with the Mayo Clinic, we were kind of 5050 in that and we sold it to axial exchange, I think was the company that we sold it to. We sold the medical in 2012. And then in 2014, we sold their real estate apps that we developed to a company called core logic. And then in 2016, we sold the news app that was sold to a local company in Minneapolis called new cycle and now it’s called naviga. The news news apps and I think the real estate app still exist in some form.

Did I hear in there that you invented the cell phone flashlight,

that it was called the highlight? I think it was basically the first kind of flashlight, which was I mean, it was a flashlight, just that the screen was white and couldn’t find things in the night? Yeah, I think that was the first flashlight in the in the App Store? I’d have to look, I haven’t I haven’t searched the app store recently. But um, I think it’s might still be in there.

Wow, talk about identifying a real need. Right there. Right?

Yeah, I just love this story. Joe, I’ve had the, you know, the fortune, the good fortune of kind of living through a couple of major compute paradigms like, you know, the birth of the Internet in the mid 90s. And as a, you know, teenager launch, you know, publishing websites, you know, right after, like, Netscape browser comes out. And you know, that just excitement, you’re just sort of when you’re that early into life, or like, I know, that’s around the time on the App Store, when you and I met I believe in, you know, we just sort of like use when you see these new kind of particular consumer platforms emerge. You know, there’s just like, so much buzz and excitement to be there early. And part of it is it’s the not knowing, right? It’s not always like this super linear path of like, what are we going to use the iPhone for, you know, from a flashlight to a help app to real estate listings or real estate apps to, you know, that ultimate, I think, was the news app business, kind of the most successful of all that. And then yeah, but like, I see that now. I think a lot entrepreneurs are sometimes, you know, maybe late adopters, and they kind of let the dust settle, but some of the real pioneering work that comes on these compute platforms. And of course, now I see that there’s always, you know, it seems like now we’re talking about Metaverse, and we’re talking about the, you know, things that are happening in VR and AR and Oculus. And it seems like, obviously, the large investments into the hardware with like smart glasses. And like, it seems like a new form factor that may eventually make its way would be the smart glasses, but it creates almost like a completely different product design. You almost had to invent it as you go, right? Because no one really knew how to design a smartphone app. You know, at the time you guys were working, right? How did you figure out even like, what to build, or what kind of UI and UX patterns to kind of use.

We had a strategy session early on, and we had like a list of hundreds of app ideas. But then actually, at the time of before the App Store came out, you could jailbreak your phone and and there’s like some, like, full kind of app stores on on the internet. And we were searching those and we thought you know, all these ideas, hundreds ideas that we had, you know, were unique to themselves. But um, we looked at these Jail Break app stores or whatever they were called. And we saw when everybody has the same fan list of ideas that we have, and the UI stuff. I mean, I personally I think of myself as a UI designer still, but the whole kind of spaces completely expanded with even even within the space, like I mean, just different designs, you have to create for all the different browsers plus the mobile browsers, the more different mobile phones. And it’s just just to kind of a headache. When you start thinking about it. You’ve had

this experience working as a part of a number of teams at Google and then some of your own entrepreneurial endeavors. And you kind of talked about the this importance of in your, in the way you were building your teams, as you’re telling the story about actually having, you know, practical experience working with a lot of the people. Can you talk a little bit about that, and you know, what’s gone into building your teams and some of the lessons that you’ve learned, I think

the strategy that Wade had, that I that I’ve tried to follow with forgiving is just, it’s just kind of finding these these people that you work well with. And one thing I didn’t realize is in Silicon Valley is that like, kind there’s the these groups of engineers that how are they met, maybe they met at school, or maybe they met at a different job, but they, they kind of go around in groups like to different people. So I noticed that after Google, like tiny groups of people, like in those project manager, as well, as engineers, they kind of went as a group down to like Facebook, and, you know, wherever else. And I thought that was kind of interesting concept that once you find a group of people that you work well with, and kind of, you know, their ins and outs, and it’s interesting to kind of follow them to different startups. And so I think that’s kind of what I tried to do. I mean, I knew Pete and Jim Well, and so I asked them to, if they would mind coming to forgiving, and they did. So I work well with them at do app, I’ve been fortunate to find the chi in my group of people. And

that reminds me of Silicon Valley, there’s an episode where they’re at Hooli. And I forget who the CEO of Hooli is, but he’s like, looking out this window in commenting to his assistant that, like the developers always travel in packs. And it’s like, judging them by you know, they he’s judging them by appearance. That’s right. Yes, or No, I remember.

Yeah. Yeah. That episode, yeah, with Gavin Belson. But yeah,

I think you see these. Yeah, it’s interesting to hear your story. And, you know, I see these patterns, you know, as an investor, and then in my own operating experience, or entrepreneurial experience, to see these patterns. And this pattern of sort of, in other worlds, and really short supply of people that know how to build digital products and do it at the highest levels, whether I’m building a product for my own business, or I’m an investor, I always kind of observe, you know, take notice of who I think are really the like the top performers that are working really well. And I sort of, I just sort of take note of that, for the rest of my life, there are people who worked with me 10 or 15 years ago, maybe even for less than a year, who I always make it a point to check in with them, like a couple times a year, because I always want to work with them, again, the kind of people who can blow you away with their execution, it could be on you know, like the software development could be designers, could be even sales or marketing talent, when you have a chance to work with someone like that you like you kind of want to spend the rest of your time figuring out how do you get them back in your orbit, so you can work with them again. So I think this kind of clustering makes a lot of sense. Because, you know, there’s just so few people that have those kind of execution abilities. And then you know, I think once you find them, and then you work, well maybe have a similar like cultural values, there’s, that kind of seems natural that you’d see these clustering. And I guess that’s probably an importance in hiring. Like, if you don’t have that kind of a network, then maybe your first few hires are going to be so important, because they’re going to lead to the next hires. And so if you find people that have been in really high performing teams, they’re going to probably want to bring their friends to come work on interesting projects, right. So you know, that real estate startup, that’s probably, you know, if you’re doing it for the first time, you don’t have that kind of a network, you know, maybe you can try to it’s so important to get those first hires white, right, because it can kind of lead to almost like a domino effect. Right.

Right, right. Yeah. So if we’re given we’re pretty small team, there’s actually just four people that are full time. And but but yeah, at some point, we’ll probably have to hire another developer, and already, you know, has a list of people that he knows that he trusts and knows, you know, similar work ethic and coding ethic that that he does, and so, so yeah, so you’re you’re absolutely right, that you kind of rely on on the kind of, you know, your core network, but then you’ll people know people and kind of expand out from there. So,

yeah, that’s super relevant. Now. i The first thing I saw on LinkedIn today was an article about procuring tech talent and competing for it effectively, because I mean, the job market right now is incredibly competitive. But after all the recruiting and all the LinkedIn posting and everything falls away. That’s kind of what it comes down to. Is these relationships. Joe? Can you kind

of describe for giving you know what was the original idea behind it. And also talk to us a little bit about how this is gonna benefit the philanthropy world going forward. Sure. So

yeah, so the ideas that I had regarding fundraiser when I was back at do app, and we are already in three different verticals, so fundraising didn’t turn out to be one of them. But I’ve been fortunate to be able to go to different galleries and events and fundraising events and kind of looked at the software that they they’d have, and like, you know, this is, you know, it’s gonna be a lot simpler. And so when I joined forgiving, it was about a, approximately about six months or a year old when I joined, I think before giving started in late 2017, I joined in mid to late 2018. And at the time, it was just the founder and he had outsource the development work to, to team that he knew. So then that’s when I brought in Pete, the developer that I said, you know, we need to bring the development in house, we can’t have a outside vendor doing it. So we brought it in house I hired Pete, who was a developer, I met that do app that’s still with us. And we started creating stuff alone, actually, at the time, I was kind of, right, I really thought that I could take on the UI stuff as well, and I did for the first few months, but I thought you know the skin too, too much. And with with other SEO type stuff that I do. So then that’s when I reached out to the gym. So he came on board and has done a great job to take over the UI stuff. So

before giving how many nonprofits are currently using the platform, and the main functionalities are kind of centered around payments and kind of marketing to donors or what some of the core functionality you all designed.

Currently with forgiving, we have approximately about 350 to 400 nonprofits and organizations using the system and, and the kind of goal behind forgiving was just to make it really simple for a nonprofit to get up and running on their fundraiser. I mean, the the nonprofits that we talked to are generally small, they have maybe two to five people on their staff, and most of them are probably part time, or they’re they’re just volunteering, they’re not even part time they’re volunteers, they don’t have time to figure out, you know, a new fundraising software. So that was kind of the point behind before giving is make it ultra simple for persons go in there quickly get a fundraiser up and running, he will share it on social media, by email or whatever,

I see a cultural issue kind of in the middle of the country after spending time in San Francisco with my last company, the lack of perceived value of equity. No, for one, we hired a lot of people here in a few in the bay area as we built up our office. And I always tell this story that, you know, we had, let’s say hello to 350 people in Minnesota. And I think I only had I can only think of a couple of times where any employees we hired really negotiated their equity packages. And then conversely, that this is a sign of the culture like in San Francisco, I think every single employee we we would hire, negotiated their equity, even not even like our administrative staff, like a receptionist or whatever. And I thought this is so different. Like it shows you the negotiation of your equity package, it sort of shows you the value that that is perceived to have.

Right? Well, yeah, that’s one thing after I left Google, that I didn’t know going in there is that, you know, I could have said, hey, I’ll take you know, X dollars less for my yearly salary for you know, more equity. And I obviously looking back, I probably should have done that. I didn’t even know that you could do that. The other thing is that I didn’t really have much money to I mean, yeah, Silicon Valley is an expensive place to live. And I’d rather probably have a place to live than, you know, equity. That may not mean anything I do I have several friends that worked at I forgot what companies this one particular year, I worked at, like three different startups, where the equity eventually went to zero because the company fell or whatever. And then Google was the winner. But I was certainly fortunate to be on that ride for for as long as I have in Vegas. I’m technically still on that ride.

Yeah, I think that’s really interesting. I that’s often advice I often find sharing with my friends that are joining early stage companies is, you know, can you go without maybe without a vacation for your for the next year or two and like maybe maybe you can get, you know, 50% more equity if you just accept 20% lower base. Or if you did that throughout your whole career, like usually the compounding nature of the equity returns is going to be like life changing for you those little decisions. Like I know everyone has different personal financial situations or goals. And we don’t most people I don’t think are really building startups just to make money. They’re building it. You know, I imagine in the case of forgiving like, death three to help simplify the fundraising process for 350 or 400. Nonprofits. It’s gotta be really easy to get out of bed in the morning, right? But I still think like on a on the financial side, it’s just like maybe, maybe, maybe just to think a little differently sometimes like, I don’t know, for whatever reason, I just find that to be a challenge sometimes here like I mean, It’s just like the corporate mindset that kind of dominates. You just don’t have the you don’t have the stories of the equity compensation really becoming kind of life changing. And hopefully that’ll continue to change over time as we have more and more big exits and whatnot.

Right? Yeah. I mean, it’s it’s kind of what stage of life you’re at. I mean, I was single when I moved out to California. I mean, if I knew better, I would have said no, less salary for more equity. But, um, but But yeah, I mean, when do we have a family? You know, obviously, you need to pay for food, housing, whatever. And, you know, the life circumstances change? So,

do you have any advice for new founders, Joe, whether it has to do with like, baking in this data driven approach, or negotiating equity or anything like that.

But as far as future founders or even just even if you’re not in to the entrepreneurial mindset is, this some stuff that we touched on before is just like finding the group of people that that you’ll maybe eventually kind of go as a group to different different companies, I don’t think anybody is probably going to be at the same company, their whole life in the tech industry, at least they’re, you know, you’re gonna probably be at multiple companies, it’s not going to be like, my dad, who was at his company for 40, or however many 45 years, just kind of finding that group of people that you work well with, and you trust and, and there’s integrity among Hmong, everybody. And the other thing is, as far as entrepreneurs, I think finding ways to get yourself out there, it helps you, I think you hone your hone the product and be able to explain the product that you’re working on a lot easier. And being able to communicate with your team as well as outside individuals, whether you’re going to investors for capital, or whatever, it’s to be able to, you know, have those communication skills.

Who do you see that is really executing right now? Are there any founders or a company? Maybe people haven’t even heard of them? Or maybe it’s Google? Who knows? You would have the inside insight on that. But do you see anybody right now that’s really executing?

Everybody I talked to, I think, Oh, I yeah, that that’s really great. I never thought of it that way. Or I never thought of a product like that. And, you know, I want to invest in it. And I can’t I mean, that I have to force myself to go through some other criteria to, to narrow down my list. But one that I keep on going and going going back to my mind is a company called pipe. And they had this product where a company can they work with, like larger companies who have recurring revenue, but like the recurring revenue, if it’s like, I’m not gonna explain this really well. But yeah, if the recurring revenue is like $10,000 a month, so that means like, $120,000 a year, well, this pipe company will match you with an investor that will pay you the you know, the upfront $120,000 for the whole year, so then you can start investing that in different initiatives that you want. And then obviously, the investor gets a little cut from that that idea might have been around for a while. But I just thought that was an interesting way to help help other companies.

That pipe company is so interesting, because I think you’re right, I think that financial model of providing almost like a loan product against future recurring revenue is sort of been around through service providers or financing companies for maybe a while, but he, he productized it in a product to scale, it actually becomes a really disruptive force for like, say, the SAS kind of VCs who, you know, in the past can make these really relatively safe investments, because of the predictability of the cash flow, the effect that would have in diluting the founders equity was pretty, pretty, pretty tremendous for a lot of the breakout SAS companies, and now with Greenwood pacement able to do to bring scale to this type of capital. So we’re seeing has the potential to dramatically increase the the founders ability to maintain equity, and maybe maybe early investors as well,

after you said, so yeah, that makes sense. Yeah. I always intrigued by ideas I like Yeah. Why didn’t I think of that? You know,

it’s kind of the mark of a good idea, isn’t it? Where it’s like, why didn’t I think of that?

Yeah, it’s, it’s like staring right at your face in your life,

like a flashlight on a cell phone. Alright.

Awesome. Well, thanks so much for joining us today. You know, I always enjoy our conversations. And he has such an interesting career that you’re on between, you know, the once in a generation kind of opportunity to work in the early days of Google and then then moving on to your own startups. And it’s just it’s incredible to hear, you know, the different turns that you’ve had in your career and to share some of the wisdom along the way. We appreciate you taking the time.

Right. No, I appreciate you offering this opportunity. I read Outliers book by Malcolm Gladwell, which I’m sure a lot of people have and I kind of see that in me that was as well as everyone in scholars were kind of born at a At the right time to be able to take advantage of these opportunities and that continues for everybody.

In this episode, Rob and Josef talk about of-coast investing, and the strategy behind Revolution’s Rise of the Rest Seed Fund and its founder, Steve Case. 

Anna Mason, Partner at Revolution, joins, and Rob talks about how they met, and about doing deals for the past 5 years. Anna shares how she went from Wall Street, with a front-row seat to the housing crisis and the Great Recession. 

She also speaks to the importance of investing in under-capitalized regions, and in being intentional about inclusivity, especially in the wake of COVID where some metrics reveal a backslide in DEI progress.

“We see opportunity first, through the lens of geography. The drive-it-home statistic that we have long focused on is that while the industry has grown as an asset class from $10B up to north of $150B a year, 75% of the capital invested every year still goes to three places: California, New York, and Massachusetts. “

Anna talks about the bus tours with Steve Case, which is an iconic exercise for the fund, and how people react to their arrival. 

Spoiler alert: Steve does not drive the bus. 

Who does Anna Mason see executing? Founder Rathna Sharad and Flavor Cloud, and recycling startup Recyclops.

Full Transcript Below:


Welcome to the execution is king Podcast, where we talk to successful startup founders, investors and ecosystem builders to uncover insights and best practices for the next generation of great global startups. I’m your host, Joseph Siebert. Joining me today is co host, Rob Weber partner Great North ventures. Our guest is Ana Mason, managing partner at revolutions Rise of the rest Seed Fund, Rise of the rest invest in promising companies at the seed stage. Were outside of Silicon Valley, New York City and Boston.


On a it’s great to have you on today. The first question I wanted to start with was this Have you briefly described your path into venture capital. And also, if you could go a little bit deeper on your thesis with Rise of the rest? Maybe any more specifics as to the focus of your role within Rise of the rest?


Sure. Thanks, Rob. It’s it’s great to connect in this more public forum. I know we spend a lot of time chatting with each other about deals and I’m excited, really excited for you guys in launch this podcast. My name is automation. I’m a proud washington dc transplant. I’ve lived in the district for about six years, I like to say I have my two favorite startups are my little girls who are two and a half and five and a half. They’re fifth generation Washingtonians. And the responsible family life choice that led us to raise our kids in DC is very much so the reason why I’m there. But along the way pretty early and I got connected with Steve and revolution team. And it’s been a real privilege and an honor to just work alongside him and my other partner, a managing partner, David hall to really grow rise the rest. It’s my path into venture I think like many is an interesting one. And part of what I love about our industry, but I also think can be a little bit challenging is that there is no one clear check the box path into the industry. So I like to say that I have a bit of an eclectic portfolio of professional experiences that brought me into venture. I grew up professionally on Wall Street, I was a distressed and high yield bond and bank debt trader and also dabbled in a bit of post retired private equity. Over the years. Long story short, I had a very, very front row seat to the financial crisis in the Great Recession. coming right out of school, I landed in a job that I thought was like the greatest thing since sliced bread working at Lehman Brothers on their distress desk, which has a strong reputation. Little did I know that shortly after, you know, a couple years after I joined, I would be trading our own bonds and bank debt on that desk through one of the largest corporate bankruptcies in history. What I would say briefly just about that experience, and how I think it tracks to my path into venture is that I find myself very frequently thinking and somewhat frequently saying that venture is very much so like the other side of the coin, from distressed from the distressed investing world, you’re making big bets that typically have very binary outcomes. But the fundamental difference, and what I really love about our industry, and about our work, it rides the rest specifically is that in venture, you’re really fundamentally betting on the bright side of the coin. And you’re just, you’re working with partnering with funding and backing entrepreneurs who are really functionally optimists, I think reimagining the future, which is a wildly different universe from working in a subset of the financial markets that are focused on trading in the securities of companies who have missed the mark, they’ve missed the innovation or have some measure of corporate malpractice that is that has taken their securities into a more distressed stage. So I learned a tremendous amount in the earliest days of my career, both from the standpoint of the nature of the work we did and I did on the distressed side, but also in having gone through a major corporate bankruptcy upheaval, and merger thereafter. And that merger experience going from Lehman to Barclays taught me a tremendous amount about corporate culture. And it’s a lot of what I try to apply from an investor lens standpoint, into how we think about team construction and team values. Because at the end of the day, whether you’re a seed stage startup with five employees, or you’re a major conglomerate with 25,000, employees or anything in between, at the end of the day, your organization is the sum of its people. And so really kind of having a feel for the good, the bad and the ugly there from some personal experiences early in my career certainly guided that experience. Wall Street was beloved and have to leave it experience. So just kind of fast tracking here a little bit. My Wall Street recovery program took me to Southern California, and I lived In LA and got involved in the awesome guests years ago, still somewhat nascent startup community, they’re co founded health tech startup called burness. We originally started in the boutique fitness booking space. Like so many we pivoted early in the lifecycle of our company, when we realized we productize the wrong value proposition, happy to talk more about that later. And that pivot led us into an opportunity where we really doubled down on community and the social psychology of fitness. And so it’s been fascinating for me to see sort of the emergence and the 2.0 of a lot of social, like vertically focused social, social commerce company is kind of coming up in the market, because we were very much so playing in that space. Back in 2012 2013, my co founder and I both got pregnant. And we were in a great place with our business, traction wise, but hadn’t fully landed on our business model. So we had an awesome opportunity to soft land, our company into a major, major private company in the space called Beachbody, which was a great home for some of our engineers and the technology and the platform itself. And I moved to DC for my responsible family life choice, which takes me close to present day. So I’ve been a revolution for five years. And it’s been a real privilege to work on scaling rise the rest.


So can you tell us a little bit about the thesis behind Rise of the rest?


Yeah, at its core, I would sum up the thesis of rise the rest by saying we see opportunity, first through the lens of geography. What that means in practice, is that the guiding light and the sort of drive at home statistic that we have long focused on is that while the venture industry as a whole has grown tremendously as an asset class, from, you know, $10 billion invested a year up to now, I think north of $150 billion a year 75% of the capital invested every year still goes to three places, California, New York and Massachusetts. And so we believe very deeply and are delighted to put our money where our mouth is that brilliant entrepreneurs can have and continue to build transformative companies anywhere in the country. But the tip of the spear in activating those opportunities is early stage seed capital. And so our model is what we call a catalytic co investment model where we are high volume early stage investors. And while we do invest across industry, over the years, we’ve sharpened our pencils to increasingly focus on opportunities that sit at the intersection of, of a handful of themes and those four themes for us, our infrastructure, resilience, digital transformation, and sustainability. And so that can take us into FinTech it can take us into healthcare, may can take us into hard infrastructure. I’m pretty sure I have a small child, my little startup who somehow broke the lock and snuck in here. But that’s the thesis for rise the rest in a nutshell.


So I’m a big fan of Rise of the rest. And I know one of the things that it’s known for our it’s bus tours all around America. I know that’s been challenging to pull off during COVID. But I wonder if you could share with us a story or two, in terms of the most unique or interesting startup ecosystems you’ve come across in your travels with Rise of the rest.


Your thanks, Rob, I’m excited to get you back out on the bus with us again, whenever it is safe for us all to convene in that way again. So I’ve actually personally been to 47 cities and counting in the five years since I’ve been at rise the rest. And so these are always the hardest questions, because picking just one or even two is tough. I thought I chat briefly about to startup communities that might surprise people, even as I’m so heartened and pleased to see how much momentum the broader thesis and interest level investing outside the coasts, has become over the last couple of years. And so one, one community that I’m wildly bullish on is Tampa, the Tampa Bay Community in Florida. I think it’s most interesting to me, and I think is worth noting, because Miami, you know, sort of just across the state has been getting so much fanfare and attention and opportunity. And frankly, I think rightfully so I’m long Miami in so far as that debate rages. But I think Tampa long before COVID and in particular through COVID has had the opportunity to really kind of double down on the ecosystem that’s developing there. So some fun facts about the Tampa Bay region, average age. I don’t know if you want to wager a guess, Rob average age in Tampa Bay? What do you think?


I would I would think it’s all I think of Florida as being retirement oriented. So I’m gonna say like you say, 42.


Yeah, it’s like 34. It’s crazy. It’s 34. We learned that when we went there a couple years ago, you actually came in lower that I that I might have thought otherwise. But there’s, you know, when we visited there a couple years ago, pre COVID. We got to see firsthand what Jeff fenech and Lakshmi Shenoy and the team at embark collective or building in the Tampa community. And what’s super interesting about this, I think of it as what what we call the work live play model in our 2019 rise, the rest ecosystem playbook. There’s a major real estate development underway there, called the Water Street project, the Tampa Bay Water Street projects, it’s like multi billion dollar, really like city renovation, if you think about it. And what I love so much about what was developed there with so much thought and intentionality is that as you redevelop different areas of a city, you have to have entrepreneurship, top of mine in front and center. And that’s where you had this really this like gem in this toolbox of embark collective, which was not only startup hub and community space, but it was really a collective to bring together leaders, mentors, investors to support this emerging generation of startups in the Tampa Bay Community. And through that, they really become this like magnet or beacon. That gives people a landing place, not only for startups who are maybe relocating, or maybe are homegrown in the region, but also for so much of the talent that’s moving to Tampa, from the Bay Area and otherwise, and either wants to pay it forward, wants to find that next opportunity wants to mentor wants to invest wants to join a startup. And now there’s a space for it. And I think creating that type of network density and concentration with intention can make all the difference in a startup community. So that’s incredibly exciting to see. And I will also say, I don’t think they’ve all been announced yet. But we have four investments in Tampa, up from zero, like two years ago. So it’s really cool to see what’s happening in that market.


That’s really interesting to hear. I’ve actually been thinking about buying a place in Florida as I as I get older, the Minnesota winters are starting to, you know, catch up to me, but I was thinking more of more like southern Florida, not necessarily Tampa. So before I buy a place in the next couple of years, I will have to spend time in Tampa and see what it’s all about. Yeah, you gotta check it out. As a entrepreneur and investor, you know, so much of success, you see really comes from having a strong team and developing a team and talent. And I know with the rise of the rest, you recently completed a nationwide career fair on clubhouse, targeting all kinds of different local talent markets, such as the Twin Cities which I participated in and others, I saw you this quote that you tweeted from Brian chesky, the Airbnb co founder, who also participated, he said, You’ll never be in one place quite like you used to be, the place to be will be the internet. So see a lot more small and medium cities rising up. I could really relate to that being I’m kind of I’m not super nomadic, but I, you know, I spent a lot of time in the Twin Cities or rural like Lake town in Minnesota, and then also Chicago, you know, but I, I don’t like to be bogged down or tied down. And I think that really resonated with me Brian’s quote, but when you think about advice, you know, as you’re counseling founders through investments that the rise of the west or otherwise, what advice would you give to founders with respect to recruiting top talent? And, you know, what do you think is working best right now? And I guess, what do you think is not working?


So I love this question about place, obviously, in a, you know, in our intro discussion, I highlighted that place really sits at the foundation of our investment thesis or programmatic work, just everything we do, centers around this idea and this philosophy, its mantra, really the only place matters. And so as we moved into this space, where the realities of COVID created, I think, what some people call zoom land, like, you know, you’re sort of in nowhere USA everywhere USA. The question about, like, What does place mean, almost, at the risk of sounding hyperbolic, you know, sort of felt like it was taking on his like existential thread, about how we should all be thinking about place and one of the conclusions I’ve personally reached, in part informed by this intentional work we did through our tech talent Tour, which as you noted, Brian chesky and co headline but it was really intended to be a virtual Career Fair that could bring together active job seekers from all across the country with these startups who are in our portfolio, we had actually over 1000 open jobs across the entire portfolio. So I think a couple things on on this front. One is that I’ve, I’ve personally come to the conclusion that we’re in this moment that I’m calling like, the great unbundling of place, where when you think about it, even from a venture investor standpoint, we’re constantly chomping at the bit and looking for opportunities, like, Oh, is this industry being unbundled? And what does that mean for opportunity? And where does value get unlocked and who can really, you know, go after and chase this opportunity? I think we’re seeing the same thing happened with place where fundamentally the value proposition of place, right, which is usually where you work, and where you live, are inextricably linked, is now unlocking and unbundling. And so just like when we think about industries that are being unbundled and value creation is happening for startups, who are sort of jumping into that moment, with a very specific product offering that really just focuses on sort of like one element of the previous bundle, I think you’re kind of seeing the same thing happen, where cities can really focus on the value prop of why you should live there. And companies can really focus on the value prop of like, why you should work for us. For this to fully work, I think for cities, and for companies, and startups headquartered in Rise of the rest cities, they’re probably actually needs to be some sort of partnership that happens between the city or the economic development authorities, or the Chamber of Commerce, and startups, who often don’t get as much attention as some of the later stage companies. So that’s something I’m actually personally spending a bunch of time thinking about what could come next there that helps not only companies in our portfolios, but helps any startup in any emerging city across the country. And so all that’s to say, while there’s tremendous opportunity, because you’re seeing so many people move for individual startups, and I know all of our companies are feeling this on the front line. It’s actually also challenging, because now you’re not just competing for talent in your own backyard. We heard this from one of our startups headquartered in Nebraska, where he’s like, I used to be the best game in town, for everyone, for all these engineers, but now suddenly, they have remote opportunities in other places, too. And so I think, for companies to really put their best foot forward as they’re trying to attract top talent, and what is becoming very quickly, like an increasingly competitive market. Is that you, I think, you really have to kind of let your personality shine. I think we’re, we’ve certainly entered this age from a consumer standpoint, and I think we’re seeing this from an employee standpoint, to where values really matter a lot. And frankly, I think that culture and values people operations is something that early stage startups may didn’t always have the luxury of thinking about. But I’ve noticed, at least across our portfolio and a new companies we talked to, it’s becoming increasingly important and prominent. So two last quick things that that I think came out of actually this talent toward the first is


we discovered, and it was an exciting discovery, that so many of our portfolio companies, even early stage ones, have heads of people, Chief people, officers, VP of talent, like not just an HR person, but someone who is looking at the whole picture of what’s our culture, what’s our recruiting process, what’s our training methodology? How do we really bring people into the fold. And I love the fact that that is front and center. And so I think that I’m thinking about how you build that function. And frankly, how that becomes not just the CEOs issue to think about, is an incredibly important tactical steps that startups can take at this early stage. And the second is, frankly, just to really transparently reassess your policies for your team. We surveyed our portfolio as part of this talent or effort. And we found that while fewer than 30% of our companies had remote work policies before COVID, more than 75% plan to have a policy, either already do now or plan to just have one for the foreseeable future. And on the flip side of the nearly 2000 active job seekers who RSVP to join us during this virtual career fair 99% of them were interested in or open to remote work. There was like one person that wasn’t interested, and 67% were interested in or open to relocation. And so I just think like flexibility is the name of the game these days. And it’s a tricky terrain, I think, for startups to navigate, because it can be distracting from a focus standpoint. So again, empowering someone on your team early Who’s sort of thinking about the people function most fully, I think is really beneficial.


So along with this unbundling of work from from place, you know, as kind of education from place as well. When you think of the uvp of these different cities, a lot of it has to do at least nowadays, you know, with with education that you can attain there. But you’ve been traveling around to these cities, you’ve been investing in these early stage startups. And obviously, there is this unbundling of education happening. Right now, I don’t know how, how progressed, it’s been put, there’s all these things, I mean, Udemy, Coursera, the ones that immediately popped to mind, but then there’s things like lambda school as well, and all kinds of other opportunities to get the education you need to work specifically in, in like startup type careers that are really proliferating. But as far as like traction, that you’ve seen, you know, like at companies, have you seen people in leadership positions? Are these founders coming out of those kind of educational backgrounds? Have you seen any traction to that unbundling of place and education,


we’ve made some investments in that space in a couple different different directions and are excited to track the progress of those companies. I can’t think of specific examples of founders in our portfolio who have been graduates of those programs. But I know that there’s active hiring that happens out of those programs. And I can say, you know, I think one example of a company in that space is to you, it’s actually DC based, you know, in our backyard in DC, they’re a publicly traded company, which I think in and of itself speaks volumes to the potential of the industry and the potential for success and real traction and efficacy of that business model. Um, but we actually partnered with them as one of our core talent partners on this recent talent tour that we did. And they brought a tremendous number of candidates through the platform. And I think what’s interesting, and what you see in some of the nuances of these models, is you have many people who are actually also leaving their current career, like they’re leaving their jobs, sort of mid cycle, mid career professionals, I guess they there’s the terminology. And they’re inspired to be a part of positive change, which I think is fundamentally what our industry is all about. And while I don’t have the specific stats for you on founders, you know, something that a colleague of mine said a while back, that’s always stuck with me, is that you don’t need to be a founder to be an entrepreneur. And I think this, having this spirit of innovation and opportunity and possibility is something that bleeds through startup cultures, whether you’re the founder, your employee, number five, or number 50. And I think you see a lot of those folks coming out of these programs into job opportunities in the startup space.


Yeah, I think that’s right on, I think one of the values that I always tried to push really hard when I as an entrepreneur was just shared around accountability. And I think that’s one of the real benefits. So you know, most startups provide employee stock appreciation plans or stock options. And I think that really kind of aligns it, you really want your team to act as if they’re owners and to take accountability when you’re building a startup. And I think that really can support that kind of a culture where every, every employee is a founder, and I think it’s really important. I was gonna maybe to change gears a little bit I wanted to ask, so your partner is Steve Kay’s. He’s one of the true pioneers of the internet. I know when I was starting out in the late 90s, as a teenager hacking away at my first websites and ecommerce projects, AOL was just a force of really kind of bringing the internet to the masses across the country. What is it been like working with someone like Steve that, you know, is really one of the true pioneers of the internet? Really? How does that impact your day to day,


it’s incredibly inspiring to work with Steve and it always has been from from day one, you know, it’s, it’s funny part of my role over the years it rise, the rest and in addition to the, you know, investment per view, and has been overseeing sort of strategy and execution, for our Rise of the rest, road trips, these bus tours that we do and that I think we’ve become pretty well known for. And it’s funny, I usually get three questions, and they’ve sort of followed me and us all through the years and through all the tours coming up on our ninth one. And, you know, the first two questions are is Steve really on the bus? And the second question is, like, is Steve running for president? You know, sort of learned, you know, my quick one two punch is like Steve is really on the bus. And and he’s no, he’s to the best of my knowledge. He’s not running for president. But I think there’s, you know, that first point It’s really like literal, like when I say like Steve’s on the bus and sort of both literal and figurative. He is, you know, front and center and present in all the work that we do. And I think his dedication has been a constant source of inspiration to our partnership to our team, to the cities that we visit, it’s always been fun in a delight to see the way that people react to and interact with him and to have the opportunity and the privilege to sort of be on the inside track of that has always been a lot of fun. And there’s also a tremendous amount of learning. You know, I think most people are not strangers to sort of the brilliant marketing behind the rise of AOL. And, you know, the CDs, everyone always talks about, but I think I’ve seen and I’ve learned a lot of that kind of shine through in the way that he’s, you know, conceived of and, and, you know, we’ve expanded Rise of the rest over the years, there’s a very specific, very deliberate, high level message that I’ve always found so impressive and inspiring in terms of how Steve always delivers it. Most people who know of our work in the space know that 75% of venture capital goes to three places. And all of the work that we do all of the investment, all the partnership, all of the focus on economic development, is inspired by that one single fact. And it’s been just tremendous learning, I think around that. The final quick thing I’ll say is, the Steve is also a great storyteller. And I think one of the first times I heard him, you know, when we were out on the road on a tour, tell the story about you know, one person, you know, when he started AOL in the early days, I don’t know if I’ll get this exactly right. But I think the story goes, like only 1% of the US was online, and it was only for like three hours a day or a week I forget exactly what that last part is. But I remember the first time I heard him talk about that, and link in his mind, the connection between sort of leaning into and creating the future with AOL, and, and drawing parallels for himself and the work that he and we are trying to do with rise. The rest was just, you know, kind of one of those that gave me chills moments, and it continues to be a source of inspiration, I think, in all the work that we do.


Here’s what I want to know, though, does Steve ever drive the bus? Like maybe it goes and sits up there he hangs a couple AOL CDs from the rearview mirror. So they’re spinning,


we do have a professional bus drivers. It’s a pretty big tour bus. We’re, he is on it. I have never seen him actually drive.


So I was gonna skip to my last question. I think the tech industry at large, but especially the venture capital market, has really struggled with diversity, equity and inclusion over the years, and I no Rise Of The rest is really at the forefront of kind of embracing diversity, equity and inclusion, from a VC point of view. So I just wanted to ask, how is the progress been? The last? I guess you’ve been with revolution for five years? How do you think the VC industry is doing in terms of embracing? You know, Dei,


my sense, in my experience, is that we’re making progress. I see it in the now much more regular announcements of you know, many of our colleagues who are women or, you know, GPS of color, or launching funds for the first time raising second or third funds with, you know, much larger numbers and a un behind them. It looks like we’re as an industry starting to do a better job. I think you see some of that too. On the, you know, the funder side in terms of what the composition of founders who are getting funded. But those anecdotes like those anecdotal insights aside, I think when we still see the headline data come through year after year, the numbers are just still so incredibly sobering. You know, from a female founder standpoint, we went backwards during COVID pretty dramatically. And the numbers were not all that impressive to begin with. And so I think we are living in an age more broadly, of increased intentionality and focus, frankly, because we all sort of live and operate in the public eye in some capacity. And I think there’s a more there’s the potential for a more virtuous circle between what your customers and what your investors and what your team sort of demands that can hopefully create more momentum and more positive change on this front. You know, one of the things I’ve been reflecting on, both with respect to geography and with an end diversity more broadly, is that I think we’re in maybe in a moment where it’s helpful to dig deeper Behind the headline numbers, because we do also have a tremendous amount of momentum in the asset class. And there are, you know, an increasing number of later stage funds. And I say this with all the warmth in my heart who are like weaponizing capital, and, you know, doing these very quick, later stage rounds that sort of inflates the overall numbers, I think of invested capital in the space, both in the fund world and in the startup world. So, you know, coming back to geography just for a minute, as we close, the headline numbers haven’t changed from the standpoint of 75% of venture capital still go into three places, but svv put out a report a couple weeks ago, where there were some really exciting data, I think, from our standpoint, it rise the rest, which is that the percentage of early stage funding, early stage specifically funding going to Bay Area startups, has actually declined 15% in the last 10 years. And what’s even more interesting to me, and I think to us, is that half of that decline has come in the last 15 months. So when you think about everything that COVID is accelerating, I think in certain ways, I think some of these shifts, you’re starting to see more acceleration and more momentum. And so that even that, just that one fact, that made me really want to double click on that, and understand, like, Where is that capital going? And what does that look like? And so there’s a lot more work to do. That’s like really the short answer behind my longer winded answer. But I’m encouraged to see more people around the table. And I’m also encouraged by the seriousness and the size of check increasingly being committed in the public forum by institutional LPs, and by the corporate community. I think, in particular, like the corporate LP community can start to make a pretty big difference when it comes to funding both startups and fund managers from a founder of color or female founder perspective.


So one last question, before you go on, we try to ask this of all our guests, sticking with the theme of the podcast, nice book into it, who is someone, or maybe it’s a team or a startup that is really executing. Or maybe it’s flying under the radar that nobody hasn’t heard of, that we should be paying attention to.


I have two companies in our portfolio. just picking up on that last thread one is led by an extraordinary female founder, the company is based in Seattle. It’s called flavor cloud. And the business is a cross border. Ecommerce enablement tool that really helps to empower every retailer to go global rathna recently closed a $6 million dollar series a round, and she’s just flying. And she’s one of the most capital efficient, sort of nose to the grindstone execution oriented founders I’ve ever met in our portfolio, and the numbers don’t lie. And so she’s already I think, come close to doubling monthly revenue, since she closed that a. So I’m really excited for the prospects of that business and think she’s writing a real wave of momentum in the e commerce enablement, and sort of supply chain resilience sectors. And the second is a newer company in our portfolio out of Salt Lake City, it’s called recite clops. And the company started as a consumer oriented like recycling as a service business that focused on rural and smaller MSA communities that didn’t have recycling services provided by their municipalities, in large part due to some changes from the International sort of regulatory landscape. And what I what I love so much about what’s happened. And they’re also just heads down executing so so efficiently is that their business has, I think, very quickly evolved not only into that consumer facing recycling as a service play, but actually now they’re sort of leaning into this reverse logistics company that singularly focuses on sustainability and the opportunities that come from that. And that’s created some really explosive b2b opportunities for them that I think are already and will continue to prove to be a short cut from a market based expansion standpoint, that helped to take them from a regional to a national player pretty quickly. So super excited about them. And they also the founder, there’s actually the younger brother of another founder in our portfolio who’s who was one of our first investments back when we launched rise the rest a couple years ago. So I love love seeing that connection come through for so many reasons.


Second generation of investees That’s great. Yeah, so listeners check out flavor cloud and recite clops. And if you google recyclates, and see a picture of Dwight schrute in a samurai outfit, that is the wrong recite claps.


It is not thank you guys so much for having me on congrats on the new podcast and I can’t wait to see Tune in to all your future episodes. Thanks, Ana.


Thanks so much on it’s been great to have you on today and looking forward to keeping the conversations going in the years to come. We’re really proud of all the good work. You’re doing it rise of the rest. Thanks, Rob.

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