Episode 418 of The VentureFizz Podcast features Jeff Glass, Co-Founder & CEO of Hometap.
Jeff’s track record is pretty amazing, yet he is incredibly humble. As both an entrepreneur and an investor, he has…in my opinion… earned a spot as one of the top builders in the Boston tech ecosystem. While success always requires the right market timing and a great team, you also need a leader who truly thrives in the full lifecycle journey of building a startup and that is exactly what Jeff has done throughout his career.
Listen to this track record.
Back in the Internet 1.0 era, he co-founded Transactive Solutions. This tech company included a web property called Zooba which scaled and had very forward looking technology. The company was acquired by a joint venture between Bertelsmann and AOL Time Warner.
Then, in the early days of mobile, he led m-Qube through each company phase from figuring out product market fit to the hypergrowth years and eventually an acquisition by VeriSign. Beyond the exit, m-Qube is legendary for its “alumni network,” having produced a generation of founders and executives who have gone on to build many successful companies in Boston and beyond.
Jeff also spent years as a VC with Bain Capital Ventures, where he sat on the board of LinkedIn for three years leading up to their IPO. He later joined a portfolio company as the CEO of Skyhook Wireless which was acquired by Liberty Media.
Today, Jeff is the CEO and Co-Founder of Hometap which has a very meaningful mission: making homeownership less stressful and more accessible. Hometap allows consumers to access the equity in their homes without taking on a loan or sell their home. Think of it like a startup, where an investor is taking equity as a percentage of ownership in a company for a future return. The same idea applies here for consumers and their home. It’s just one of those ideas that makes a world of sense.
Chapters:
00:00 Introduction
03:40 Building Extraordinary Teams
07:38 Jeff’s Background & Early Career
15:15 Learning How to Sell
23:27 Early Career
28:30 Building Zooba to an Exit
39:49 m-Qube and the early days of mobile
44:33 Powering the Voting System in American Idol and Deal or No Deal
47:15 VeriSign’s Acquisition of m-Qube
50:41 The amazing alumni of m-Qube
54:27 Joining Bain Capital Ventures
58:30 Joining Skyhook Wireless as CEO
01:01:15 The Early Beginnings of Hometap: A New Approach to Home Equity
01:06:28 Building Hometap: Raising Capital and Growing Initial Customer Base
01:12:43 The Scale of Hometap
01:16:08 How Hometap Works
01:20:17 What’s Next for Hometap?
01:22:09 Jeff’s Interests Outside of Work
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Transcript:
Keith Cline (03:13)
Jeff, thanks so much for taking the time.
Jeff Glass (03:16)
It is really fun, glad to be here.
Keith Cline (03:19)
I’m excited to talk to you, because we’re gonna take a nice little trip down memory lane through lots of companies that you’ve been a part of that have all been successful. So we’re gonna talk about, know, legendary companies that are like pillar companies that have just gone on to do extraordinary things. But before we get into your background story and career, I thought it’d be good, because I just know one of the common thread of your companies that you’ve built was building a very successful team, which…
I know that’s probably the mindset of every entrepreneur is to build a great team because it’s the team, not always the idea that executes and builds a long standing company, but I think some entrepreneurs maybe struggle with that. So what has been kind of your thought process around assembling a team that’s able to achieve extraordinary results?
Jeff Glass (04:07)
I think part of having a great team and building a great culture is first recognizing the importance of it and trying to be intentional about it and not just letting it happen by accident. And I do link
in my mind, culture and team, because I think what makes a team work well together is a common set of cultural values that everybody believes in, buys into, and tries to live by. And by having that common set of cultural values and kind of a mission and a set of goals that people are excited about.
You know, that’s, I wouldn’t say that is a guarantee of success, but those are the prerequisites for having a shot at being successful. And I think also part of it is recognizing the fact that it’s never done, right? Because like a team is a set of people and we are all human and we all have flaws and strengths and weaknesses.
And we also have things that are happening in our lives that are outside of work that can have positive or negative impacts on our ability to be able to get done and to participate the way we want to. So I think, like I wish I had a great answer of the magic formula for how good teams are built. I think it’s just, you try to hire people that…
believe in the goals, believe in the mission, have consistent set of values. You echo those values. You try to practice those values and you just be prepared to know that every time you think you’re in a good place, something is going to shift. Someone will move on. Someone has another opportunity. Someone has a personal situation. The market has changed. The competition has changed.
and it’s just a perpetually dynamic, never-ending ⁓ set of activities that you’re trying to do.
Keith Cline (06:07)
there is no secret sauce. But when you did make those hires, how did you think about, yeah, maybe they are aligned with your culture and values, but ⁓ I’ve heard lots of different CEOs, founders talk about their hiring practices. And to have your executive leadership team, that being like your pillar of strength, that can be tricky. So how did you think about like hiring for that, you know, direct report relationship?
Jeff Glass (06:33)
Well, I mean, for starters, anyone who’s worked with me will agree with this, which is I’ve had no hesitation to hire people who are better than I am in many different ways. ⁓ And I think you have to be comfortable with that. ⁓
You know, I’ve been working with the president of my company at Hometap a woman named Sarah Deacon, for eight years, and she’s unbelievably talented in so many ways that I could never achieve. I’ve had similar folks, not just at Hometap, I could go through a list of folks who are all more talented than I, and if I were to talk about folks inside previous companies, the same would be true.
so I think that’s part of it is like, just have to recognize the fact that you can’t be better than everybody at everything. And you should actually be grateful when you have the opportunity to work with people who are better than you. And that of course gives them room to do their thing and to be successful and to hopefully feel satisfied in their roles.
Keith Cline (07:38)
And we’re gonna talk about some of those teams, which I’m really, really excited about. ⁓ Okay, let’s rewind the clock. So let’s talk about your background story. So where’d you grow up and what were you like as a child?
Jeff Glass (07:48)
⁓ I am a proud product of Brooklyn, New York. ⁓ Moved to Brooklyn at, I believe, three or four days old. ⁓ And so, ⁓ yeah, I really spent my whole life in Brooklyn. I’m a product of Brooklyn public education, PS 217, know, Dipmix JH62.
You know, we’re not fancy with names in Brooklyn and the great Midwood High School. And, you know, I grew up in a pretty average household in Brooklyn and my friends, you know, we’re all grew up in relatively blue collar, average working class households. And it was pretty good. You know, it was rough at times.
Keith Cline (08:17)
Right? Like what is that?
Jeff Glass (08:42)
⁓ Like a lot of growing up is rough, ⁓ but it was fun. I played a lot of sports. I worked hard in school. ⁓ My family life was pretty good, not without challenges, but I was very lucky. My dad was actually a high school dropout ⁓ and hadn’t finished 10th grade. ⁓ But super smart man. ⁓
very, very driven personally, and kind of recognized how hard his life had been as a result of his ending his education. And so, you know, in a lot of ways I benefited from that because, you know, he persistently told me that my job was to do well in school. And he, you know, he made me pretty competitive, you know, which has pros and cons.
but he turned me into a very competitive person driven to do well. ⁓ And my mom sort of drove me similarly, but from a different direction. She also had a pretty rough childhood and her dad had passed away when she was five or six and her mom had to work and she was largely raised by her very 10 years older than her sisters and her older family members. And so she was perpetually worried.
And so she grew up in House of Worry. And so, yeah, I got it from both sides. I got my dad’s, ⁓ you gotta go compete and do well. And I got my mom’s, and if you don’t, then things will be horrible. ⁓ So yeah, you’ve got yourself a very neurotic CEO, serial entrepreneur that you’re interviewing here, Keith.
Keith Cline (10:30)
I like to call that a chip, right? That’s a chip on your shoulder, which is a very good thing. think everyone needs to find that competitive spirit somehow, some way. So what are the, you know, in preparation for this podcast, obviously I listened to some other things that you’ve done and in high school, you learn sales going door to door, furniture sales and like, I wish,
I think it should be a requirement maybe in college for every student to do some type of sales, whether it’s cold calling, door to door, because if you can survive doing that, you’re probably going to succeed in lots of other things in life.
Jeff Glass (11:11)
Well, I don’t know if I got more rejection having doors slammed on me trying to sell furniture than I did in trying to ask people out during high school and see if they would go out with me on a prior night. I think I had a pretty good balance of rejection on all sides of my life. So yeah, if that, you know, what doesn’t kill you makes you stronger. So I guess I have that to be grateful for.
Keith Cline (11:25)
You
Jeff Glass (11:35)
And so I applied to a bunch of schools and had gotten into a bunch of good places that were very expensive. I mean, like,
you compare that to now and they look dirt cheap, it’s like, but back then, you know, for what, what we had was super expensive and it was definitely going to be stressful on, my parents and on me and even with financial aid and everything else that schools were trying to do, it was going to be tough. So my goal was to just try to get a job where I could make some money and, put something away so that I would, you know, occasionally be able to, you know, buy a pizza and, and be able to.
have an okay social life in college. And so I actually started working at a trucking company, which was the highest paying job I could get, which was a trucking company that delivered the furniture. And so I was working in the warehouse and I was carrying furniture and I kind of liked it. I was young and I looked at it as an opportunity to get paid. It paid pretty well on an hourly basis and I was like,
getting in shape and getting strong. And so I kind of liked it. ⁓ But basically after a while, was sort of ⁓ clear is they just didn’t really like having high school kid hanging around. And so I went to the owner of the office furniture company who’s
was a, whose furniture this trucking company delivered. And I said, hey, is there something I can do here? And the owner of the company said, look, you we were only looking for salespeople right now and it’s commission only. There’s no draw, there’s no salary. There’s really no formal training. You’re a high school kid. We sell to corporations and companies here in New York. Like the office was in Manhattan. Like you’re like,
And I said, great, I’ll take it. And so that’s how it started. And so I learned a little bit about furniture. I remember specifically I dug deep into the knowledge base of learning about file cabinets, which for those listening, a file cabinet used to be a piece of furniture that people would keep something called paper documents in an office. so I learned a lot.
Keith Cline (13:32)
Hahaha
A lot of metal.
Jeff Glass (13:59)
What’s that? Yeah, they were, yeah.
Keith Cline (14:00)
A lot of metal to make that thing.
Jeff Glass (14:02)
Yeah, there were two drawers, three drawer, five drawers. There were vertical files, lateral files. I mean, that’s still coming back to me here. Anyway, so ⁓ yeah, so I learned a little bit about furniture. I learned a little bit about file cabinets and the office that I was working at, the sales office, was a couple of blocks away from the Empire State Building.
And so I, back then you could do this. You couldn’t do that. Like my entrepreneurial career would never have started today because of building security. But I grabbed some brochures and I went to the Empire State Building and I literally canvassed my way. I knocked on every door from the lowest level to the last, know, to the highest floor saying, hey, this is Jeff Glass. Can I speak to the person who handles your office furniture? And that’s where my kind of business and sales experience began.
I sold a couple of file cabinets over the remainder of that summer. Probably came close to breaking even versus what I might have made if I had gotten paid my hourly rate ⁓ carrying furniture. And then I went back the following summer after my first year in college and actually did pretty well.
Keith Cline (15:15)
So what did you learn tactically that was how to sell, meaning relationships or your approach?
Jeff Glass (15:23)
Um, I mean, the first part, what you hit on is that you just have to be able to emotionally detach yourself from the persistent rejection that you get. Right? So I was walking into people’s offices. I would talk to the receptionist and then the receptionist would mostly tell me to go away. Um, and that was their job.
Keith Cline (15:47)
That was their job. Go
away.
Jeff Glass (15:50)
Yeah, and I was polite and professional and they were mostly polite and professional, not always. But you just, you knew that there were companies out there who needed office furniture and you had to just go find them. And so you had to treat this less that I’m, you know, that I am an imposition on you or that I’m bothering you or that I shouldn’t be here, but more of like, I’m here to figure out if you do need me and if I can be helpful to you.
And if the answer is no, then that’s okay, I will move on. But like that psychological ⁓ learning is really important. I think you definitely develop a little bit of a quick, able to be a little quicker on your feet and to be personable and to handle those situations and try to find some way to build rapport very quickly so that you don’t get kicked out of the office.
Because even if they don’t need furniture at this moment in time, it wouldn’t be bad if I could figure out who does handle it so I can talk to them next time or follow up with them or send them something. So I think there’s some interpersonal skills that you work on there. ⁓ And then once I started having some success, I learned a ton about relationship management and client management and you’re helping them.
You really, the way I thought about this was I thought about like, I’m not providing a sale, I’m providing a service. If in fact you need office furniture, then I am now a service to you. I am no longer like a ⁓ pushy commission office furniture salesman. I’m now providing a service. And so you having that mentality and then treating clients with a service mentality and helping them think about what might be right for them.
and managing the process from the selection to delivery and installation and dealing with problems afterwards. Those were lessons that are true in every business, no matter what product or service you might be delivering. And so it was really good. I also got a little learning on the marketing side because the second year I did this, I had been cold calling, both knocking on doors and making phone calls and…
buying lists of the top law firms, the top advertising agencies, the top whatever, and it was really a low probability hit rate. And then I discovered this publication that was this, it covered, it was a listing of companies that were in transition, that were moving. Yeah.
Keith Cline (18:34)
Nice.
Jeff Glass (18:36)
And so I said to the owner of the office furniture company, I’m like, hey, we should get this. And it was a few thousand bucks. And he’s like, I’m not getting this thing, whatever. And so I said, I’ll tell you what, you I didn’t have the money. Like, please invest in this and I will, you can take it out of my commissions and I will work for you here in the office until I pay you back for this thing. But like, this is going to be way better than just randomly calling companies. And shockingly.
You know, if you’re calling companies that are in transition, you’re going to have a much higher hit rate that they might need furniture than just randomly calling companies. And so that was also, you know, those were early lessons about customer segmentation and targeting and trying to be thoughtful about qualifying leads and opportunities. So, ⁓ yeah, I learned a ton, ⁓ from that experience and, ⁓ and still can tell you a little something about.
supreme five drawer ⁓ lateral file cabinets. They came in three colors and can offer you a good price.
Keith Cline (19:37)
⁓
So, and I am a firm believer of these foundational years, having this overall arching impact of somebody’s trajectory. So that’s why I wanted to focus on that for a bit.
you pursued an entrepreneurial journey of college apparel like being overpriced.
Jeff Glass (19:56)
I did start a company my freshman year and ran it all four years of college. ⁓ But I will say, you know, we’re all, you know, we said before this thing started, I told you, I don’t really do a lot of these things. And the reason for it is because I genuinely feel like a lot of life and business success
is serendipity, it’s luck, it’s happenstance. It’s like being in the right place at the right time. It’s like getting the right person happens to join your company and they’re so amazingly talented that they make this you. So I don’t I’m always a little bit uncomfortable talking about some of these things because I do believe like there’s so much more out there that leads to success and failure than just your own hard work and effort.
And so, I mean, for sure you need to put hard work and effort in, but there’s so much more out there. But, but even something like Amherst, which, you know, I had never really heard of Amherst College. I, know, it was a small liberal arts college in Western Mass. grew up, mean, Amherst was smaller than my high school by a lot, like half as small as my high school. And so, you know, I hadn’t really heard of it. I stumbled into an info session during my
junior or senior year in high school. They happened to come to my high school. And even then I didn’t really think I would. was applying to schools that were more well known. And my mom, you know, last second, she’s like, I thought you liked that college. Why don’t you? Did you send in your application? I’m like, mom. And so, you know, mom again, frickin does right. And it’s always the mom. And so like the night before it’s due, I send in the application. I get in. I still don’t think I’m going to go. I go up to visit.
I just have this amazing time there and felt it just felt comfortable. And so I made this decision to go to a place I didn’t really know that no one had really heard of at the time compared to more well-known places, which again was a good lesson around like do what feels right.
But I remember my dad who had sacrificed so much and who was a high school dropout. And he was like, know, Amherst, what is Amherst? Like where is Massachusetts? You know, I’m kidding. He knew where Massachusetts was. But all that… then, but one of the things that was remarkable about going to this small school was that you could do stuff and try stuff, right? Like if I went to Michigan, I wasn’t going to walk onto the football team.
You know, if I went to some big school and so it just was this amazing place where I was able to try things for the first time, whether it was play football or you or have a radio show or be involved in theater or like a whole bunch of things. And I do think that, you know, when I was thinking about you.
organizing a little bit for this interview, I was like, I think it mattered. I think it was the seeds of entrepreneurship of saying like, you can just try. Like you could give it a shot. Like you might not exactly know how to do it, but.
you’ll figure it out. And I think that is a big part of what allows entrepreneurs to move forward because you never know what you’re going to need to do until you get into the battle. but I think Amherst was a big part of shaping my mind to feel comfortable doing that.
Keith Cline (23:28)
so after college, you go on strategy consulting. ⁓
HBS.
After that world, right, because that’s obviously a great foundational world, HBS amazing, of course, ⁓ what do you do as far as your next journey into industry, more startup world?
Jeff Glass (23:55)
Yeah, so I had been very entrepreneurial, right? We talked about I sold office furniture. We didn’t talk much about it, but I started this company in college, which was a college clothing company that morphed from being a mail order company to an on-campus company to a group clubs and teams and distribution. And so I had this entrepreneurial ⁓ component to me. Now, I will mention, I still thought I was going to go to law school. ⁓
You know, like when you grow up in Brooklyn, New York and you’re smothered by grandparents and great-grandparents and your great-aunts, you know, first of all, like anything south of becoming president of United States is a complete failure. And like, maybe you can get their, their, ⁓ okay. And approval if you at least go to med school, but absent that you’re basically don’t exist. So
You know, so I had thought about med school when I got to college and took a lot of science classes during my freshman year and then decided ⁓ once I looked at what organic chemistry had in store for me that that was, it was time for a career change. And my drop down menu was ⁓ I really wanted to do something for the, in sort of public service. And so I thought I’d go into
and go into public service into the government of some flavor. ⁓ And I stumbled into, again, this is why I don’t think I can take credit for anything because you might have, I’ve realized now I’ve used the word stumbled like at least two or three times in this conversation. Just like I stumbled into an info session to see Amherst College when I was in high school, I stumbled into an info session for a company called Banning Company, which is strategy consulting firm and
And I had never heard of management strategy consulting and that like as a young person, you could be doing analysis and working on presentations to help Fortune 500 companies with their global strategy. Like, wow, like who doesn’t want to do that? And so I ⁓ applied to law school, got into law school, deferred law school, got a job with Bain & Company, figured I’ll do that for a couple of years. Maybe I had financial aid loans to pay back. I had a lot of debt. My parents had debt.
I wanted to take a little bit of break and maybe make a few bucks. And I go there, I got laid off six weeks after I joined the company. I moved to Boston. So that was another back to what forms you as an entrepreneur? Okay, I went to get this really safe job and six weeks later I’m unemployed.
Keith Cline (26:20)
man.
Jeff Glass (26:32)
But frankly, back to better to be lucky than smart, ⁓ I met my now wife.
for over 30 years because she and I got laid off together. so, and once neither one of us had a job, I, know, unlike my unsuccessful ⁓ asking people out in high school, I said, hey, what do want to do something? I knew she didn’t have plans because she had just lost her job. yeah, so in a lot of ways, even though that was a tough experience, like it was an amazing experience. It was literally a life-changing experience, both from a personal standpoint,
Keith Cline (26:44)
No way!
Right?
Jeff Glass (27:09)
at a professional standpoint, which is another takeaway I think about, which is like, you just gotta recognize that even when bad stuff happens, you can, with the right attitude, you can turn that bad thing into something good. ⁓ So.
I spent a couple years, I got laid off. I wound up going to a different strategy consulting firm, the Boston Consulting Group, which was great. I then went to B school. I went back to the Boston Consulting Group, ⁓ who was kind enough to sponsor my education and help me. You’ll be in less debt after business school. And then I said, okay.
I built up a little bit of like the strategy and finance and sort of business skills part that was complimentary to my sort of natural sales and entrepreneurial and.
kind of external part and I felt like, okay, I felt like I had built the right skill sets to go back on a entrepreneurial path. ⁓ And then I went to a small company that had been acquired by Travelers and that was a cool experience. I worked for a woman there who was this amazing mentor to me and I learned a ton from her. ⁓ And then I became a tech entrepreneur in the late 90s and started my, you know, started an internet company.
Keith Cline (28:30)
Okay, we’re gonna talk about this company.
Can you see my screen here?
Jeff Glass (28:36)
my gosh. Holy cow. That is a blast from the past. You went back in the time machine to find that, huh? Wow. I’m feeling.
Keith Cline (28:43)
Yes, I did. The beauty of the Internet
Archive Wayback Machine. Thank you. ⁓ Yeah, so let’s talk about Zooba or properly known as Transactive Solutions.
Jeff Glass (28:48)
my goodness.
my goodness, you really caught me by surprise here, Keith. I haven’t looked at this in…
you know, a long time. Okay, so a friend of mine comes to me, he had been the COO of a media company. I had been the COO of this division of Travelers, which was largely a direct marketing and sales organization. And this was his idea. His idea was, this was late 90s.
Brands are spending absurd amount of money on brand advertising, trying to drive traffic to their website. Their customer acquisition costs are like 10x the lifetime value of the customers. Like none of the math makes any sense. And so he has this idea of can we use content to understand more about consumers?
and then build kind of a dynamic analytical engine to be able to personalize content and merchandising and offerings based on what people’s preferences and interests are. And can we build the technology to do that at scale and really promote like product level and direct marketers mentality. And I had kind of been in the direct marketing space for several years and he had been in the media content space.
He
had this high-level idea. We spent some time brainstorming on it, and we come up with the idea we’re going to create Transactive Solutions. And Transactive Solutions, as the exciting name indicates, was meant to be a technology company. ⁓ It was the combination of this distributed content management system.
this analytical engine that would build demographic and psychographic profile of the user based on their interactions with the content. ⁓ And then this dynamic merchandising capability that would be able to then, based on those profiles, serve up the right ad or the right product ⁓ to the right customer. And so now you think about that and it’s sort of table stakes, but back in the late 90s, that was kind of a cool, innovative idea.
we said okay the first customer will be Zooba
which was meant to be a proof of concept, which was this content site where you could sign up for really well written short, concise emails as you’re showing here on the screen and bringing me back a long way. I literally have not seen these things since the early 2000s. So we’re talking 25 years here. And, um, and it turns out like he was brilliant on the content side. We got this, we built this network
Keith Cline (31:30)
Yep.
Jeff Glass (31:47)
thousands of experts who were so
excited to write about these short, editorially concise things that people wanted to know about.
⁓ it wasn’t meant like at the time email was very spammy and low quality content and it wasn’t controlled. there was, this had a publisher magazine like idea to the content. And we built this dynamic technology so that our thousands of content creators could, could produce stuff. had internal editorial teams. We built this dynamic psychographic profile engine. We built this technology to go from broadcast email to what we called microcast where each one was built
dynamically on the fly based on the profile and so we did all this crazy stuff in super fast time because we were working about 300 hours a week and ⁓ and the business went from nothing to six and a half million subscriptions of Zooba ⁓ really really fast.
And I could give you a whole bunch of like crazy stories of what it was like to do business back in the dot com era. But we were there at the very tail end. The bubble was bursting and we got completely lucky that this joint venture of AOL and Bertelesmann saw value in the content, the technology, the traction, all the user metrics. And we got acquired. And frankly, if we had not been acquired, I suspect we probably wouldn’t have been able to survive
because funding back in early 2000s for anything internet and technology effectively went to zero.
Keith Cline (33:25)
Yeah, but like you said, these are all table stakes now, but back then, this was like homegrown applications at your building. That was really, really difficult to pull off.
Jeff Glass (33:35)
It was cool and it was, you know, I wish that we had either started that a few years later or a bunch of years earlier because I think ⁓ it really had the ideas inside it were intellectually compelling and forward looking at the end. But again, it worked out well, you everybody did well and it was a good acquisition ⁓ for this joint venture and it was a crazy time. I mean, when we first started this business,
we got a term sheet from an investor and the term sheet had a three day exploding offer. So you have three days to take my money or free. Like we were trying to find a law firm and I met this law firm and sat down with this partner and had this nice conversation. And I was like, all right, so like, how do we get started? And she’s like, okay, well, we’ll get back to you and let you know if we want to take you on as a client. And she sent me a rejection letter in the mail. It was like being in college again.
It was like getting like, dear Jeff, thank you very much. Dear Jeff, thank you very much for applying for to be a client at our law firm. Unfortunately, we don’t have any. And look, this is no reflection on you. We’re sure you’re going to be successful. Sincerely, the law firm. ⁓ You know, we met with a tech firm consulting firm to try to ⁓ get jumpstart because we felt the pressure of like
Keith Cline (34:34)
Wait, the law firm rejected you as a client?
Jeff Glass (34:57)
the dot com and everything was moving fast. We wanted to like have an outsourced firm help us build some of our early stuff. And I remember the meeting 10 minutes in, he let me stop you. We’re only taking clients on that will do at least 4 million a year for three year minimum deals. I said, well, I just raised a series a I raised $6 million. You I only have six. You want me to pay you for and guarantee you another four for the next two years of money. I don’t have. If you can’t do that, then we’re just not interested.
Like that’s what we were dealing with back. It was, I mean, I wish we could have a podcast of just like people who built companies back then of just sharing all of the crazy stuff that was going on. It was, it was a lot. It was a lot.
Keith Cline (35:35)
Right.
Yeah,
That would be a fun conversation. We should do something like that.
the next stop in the journey. ⁓ So m-Qube is such a legendary company. ⁓ And we’re talk about what you do and everything, but from my podcast, I’ve had Lars Albright, Mike Troiano, Jennifer Lum, David Chang, all on the podcast in the past. So we’ve talked about the journey, Andy Miller, Eswar,
I mean, Jason St. Pierre is building a company, like there’s so much value that this company had in terms of an ecosystem development company like a pillar. ⁓ So how did m-Qube come together as far as the idea?
Jeff Glass (36:51)
That was a special company and the people you mentioned, every single one of them are special people. I definitely get, even just thinking about that, get a little emotional and sentimental because it was very special. I had this business acquired by this joint venture that I mentioned. There was VCs in Boston, General Catalyst.
who were not investors in my previous, in that previous company, but who had looked at it and decided not to, were incredibly, like beyond over the top, gracious around like, you know, hey, how they even knew about it. Like they sent me a congratulations note before that even, like before I even knew that the deal had closed. And so they were incredibly gracious and invited me to come spend some time with them and explore opportunities and ideas. And there had been this very different,
mobile idea that had been explored that for a bunch of reasons didn’t work and had largely disbanded. But there were a couple of ⁓ people, mostly engineers, who were still kind of hanging out inside General Catalyst’s offices, ⁓ poking around at mobile trying to think about was there a next generation idea around mobile that could work. ⁓
And, ⁓ and you mentioned Eswar Priyadarshan. So Eswar was, was one of those folks and, I got introduced to Eswar and they were working on some stuff and I had, you know, just come from the internet marketing world where I had built Zooba, Transactive Solutions. And before that I had, you know, run this other company that was ⁓ largely a marketing oriented company, sales and marketing oriented company. And so the high level was like, hey, is there something here around the concept of mobile marketing?
And they were kicking it around. And so I, ⁓ got involved in it and we started working on ideas and trying to think about like, is there a next generation business plan here, ⁓ to build a mobile marketing? I don’t even think the term SaaS was used yet at that point. I think it was an ASP. Yeah, it was a, it was an ASP and app. So we were like, we’re going to build a mobile ASP and we’re going to help connect mobile.
Keith Cline (39:04)
Application Service Provider, yeah ASP.
Jeff Glass (39:13)
to CRM and other marketing software and technology so that brands could include mobile into their broad way of communicating and interacting with customers over time. So that was the original idea. It was way ahead of its time. ⁓ 2001, 2002, we did basically no revenue. We were living off of bugs and grasshoppers. ⁓
trying to pitch mobile marketing solutions. As I used to joke around, we were the leaders in a market that didn’t exist.
Keith Cline (39:47)
Well, just let me bring this up for you too. So just for the visual, right? This is…
Jeff Glass (39:51)
Okay. I guess,
you know, just like I look at that and if you were like, so is that your website? like, I guess that had to have been our website, but I have no specific recollection of these of this page. ⁓
Keith Cline (40:07)
It’s like flip
phones, right? This is not, you had to like sell the carriers like Verizon and Cingular. You had to sell the Cingular and Sprint.
Jeff Glass (40:11)
⁓ yeah.
⁓
I mean, it was flip phones. When we first started ⁓ m-Qube, ⁓ there was no interoperability of text messaging. So you could not send a text message from a Verizon phone to an AT&T phone. There were carrier, there were carriers called Cingular and Altel and Nextel and, and, you know, in all sorts of carriers that don’t exist today, it was, it was early.
Keith Cline (40:30)
⁓ yeah, I forgot about that.
Jeff Glass (40:45)
And this is a good thing, something I think a lot about as a serial entrepreneur and I did spend some time after m-Qube as a venture capitalist for a while. ⁓ Market timing is so important, but the problem is that it’s impossible to nail the market timing other than just blind luck. Like every once in a while you could. And so you’re either gonna be too early or too late.
And if you’re too early, the question is, can you survive long enough until the market actually materializes? Because if you don’t, you run out of money and you’re dead. Or you come in too late. And if you come in too late, then the companies that came in early and managed to survive those early periods, they’ve got a massive advantage over you and have leadership in it. And so m-Qube was a bit too early, but it was just like maybe within a few months.
Not too much early that we died, but we were almost dead without question. Again, back to this, like, you know, people take too much credit when things work and think they were so smart. Like this business, just like Zooba, just like my company in college, like all of these businesses are so fragile and the,
Keith Cline (41:53)
Really.
Jeff Glass (42:14)
the edge between success and failure is like one lucky break, one thing going your way, one thing happening just in time, one investor coming in, you know, and giving you enough capital to kind of make it across till you actually can start seeing some real traction in the business. And that for sure is what happened to m-Qube. I mean, we were, it’s a tale of two cities.
We had no revenue in 01, 02, I think in 2003, we did like $400,000 of non-recurring services revenue. And then we changed the business model, the market had been changing, we migrated from mobile marketing management to mobile messaging management to mobile media management. The good news is all of those were…
to the third, so m-Qube So we were able to stay within our logo, which was the key part of the whole. And yeah, and we scooted by and ⁓ we managed to get deals done with the carriers. ⁓ We knew we needed to migrate into mobile content. Another great lesson I learned in that business was it’s in a new technology, a new market, it’s easier to sell a new revenue center than a cost center.
So this mobile media management was about helping brands and media companies and content providers monetize their existing content over a new channel, mobile devices. And so was a direct new revenue stream for them. Mobile marketing was an opportunity for them to further carve up their existing digital budgets into an unproven medium where it was still kludgy and on flip phones and bad handset experiences.
And so in retrospect, it was clear that it was better to lead with this revenue enhancing opportunity than the mobile marketing side. But you got to learn these things through the school of hard knocks. So yeah, we went from being almost dead to then being one of, if not like the fastest, I think certainly in New England and we were one of the fastest growing companies in America. was like 0, 0, 0, 6, 84, 250 million in revenue. mean, it was…
Keith Cline (44:30)
Wow.
Jeff Glass (44:31)
It was insane.
Keith Cline (44:33)
And I’ve heard some legendary stories of Deal or No Deal, the TV show, and American Idol. You guys were the back end of the voting systems, like the Magic Briefcase and then American Idol voting.
Jeff Glass (44:48)
Yeah, because one of the things that we, the chicken, every startup has a chicken and egg problem to crack, right? And if there was not something hard to crack, then somebody would have already been doing it and there’s no longer an entrepreneurial opportunity. So in this business, you didn’t have a value proposition to consumer facing companies unless you could tie together all of the backend wireless operators and provide that as like a complete unified infrastructure for them.
So, but of course if you went to the carriers, you know, they were not super quick and keen to let you into their messaging and billing infrastructure and to give the keys to the kingdom, ⁓ all for the promise of you might someday deliver something new to them. And so you couldn’t have the brands without the carriers, you couldn’t have the carriers without the brands and therefore like every startup, you shouldn’t start it because it can’t be solved and you should just go get a desk job.
⁓ And so we managed to crack it and ⁓ and as a result, like we wound up having all of the carriers on our platform. And so as folks started to, ⁓ you know, vote for your favorite American Idol or pick the suitcase that has, you know, that has the best the dollars and deal or no deal, you know, we were one of a very, very few number of companies that had both the reach across all the carriers
and the technology to be able to handle what at the time was very, very difficult ⁓ spikes in traffic load. So, our operations team and our engineering teams just did such an incredible job of keeping up with that. And it all happened so fast. It was a light switch. was the craziest thing ever. I joke that like,
you know, for multiple years, I could have hand delivered each text message that went through the m-Qube infrastructure because there were so few. I could have just like run over to your house and said like, hey, Keith, you got a text here. And then, you know, and those volumes went from like in the thousands to within six months, they went from in the thousands to the millions to the tens of millions to the hundreds of millions.
Keith Cline (46:53)
got text.
Jeff Glass (47:07)
To that we were moving billions of transactions over our infrastructure. Like it was a crazy time.
Keith Cline (47:15)
So how did the Verisign deal come together?
Jeff Glass (47:19)
So the thing about that business is we were this technology intermediary between brands and the carriers. And so ⁓ if you think about kind of competitive forces and strategy issues, the carriers really had all of the power and the carriers were consolidating. So ⁓
Right. Like there used to be a carrier called Cingular but then that became Cingular and AT&T and there used to be Altell And then that got bought by Verizon. And so there was an anti-mobile like T-Mobile and Sprint and all these, all these carriers were consolidating. And so from a strategic standpoint, we were doing really well. We were growing really fast. It was also really fun because our customers were media companies and entertainment companies. And so we were.
We were providing mobile for Major League Baseball and all the big music companies and brands. And it was a lot of fun, like the kinds of stuff we were delivering. But we kind of felt like the pressure on the business was going to come from the carrier side and that we really thought strategically you needed to be broader in terms of your relationship with the wireless carriers. And so for us, we thought, OK, this should,
this should be offered as part of a technology company who has multiple things that they do with wireless operators and negotiating in multiple ways. ⁓ And Verisign who had been super strong in sort of the underlying infrastructure for the digital economy, which to that point meant internet, you know, was clearly thinking about mobile as the next extension of the digital economy. So from our standpoint, it was sort of helping us strengthen
our ability to be viable relative to the wireless operators. And I think from Verisign standpoint, it was helping them build out this enterprise business that further brought in mobile capabilities and mobile technology. So it was, it was good. We had multiple bidders for m-Qube It was, it was a dramatic and stressful and ⁓ exciting and emotional process. And you know, the, remember the night we, we closed
and when we signed and closed the deal, it was really late and it just been such an emotional both like surviving for the first several years and then drinking from a fire hose of like ridiculous growth and having this very crazy, you know, M&A process. Personally, during that period of time, both of my parents passed away. Like it was a lot and I just remember when it was over like sitting in my office and weeping.
Not weeping of happiness, now like, I just made some money. Just like weeping from the release of all of the emotional pressure and stress that had been on both sides. The stress of not screwing up now that you’re growing and doing so well and the stress of surviving when you’re like thinking that every day, should we keep doing this? Am I being fair to my employees and to my team and to investors by…
Keith Cline (50:18)
Bye.
Jeff Glass (50:41)
keeping the dream alive when we’re not sure if this thing can get to the other side. Like it was, it was a lot, but you you mentioned some of the people there and there’s a lot more you could mention. We started that company, you know, in, in 2000, end of 2001, it was at the backend of the demise of technology and the dot com crash. And so we were able to attract just the most incredible set of people.
Keith Cline (50:53)
Way more.
Jeff Glass (51:11)
And, you know, again, we went through this survival mode where that really bonds you because you’re literally fighting for survival. And then we went into this crazy growth mode. And so I think that the relationships amongst the people who work there for a lot of that are like, they’re so tight. I still speak to so many people from the m-Qube days. I’m still close with so many still work with so many. ⁓
I’m so proud of how many people, like as a result of all of the learning and experience, both from a technology standpoint and market standpoint, you know, there’s like dozens of people, maybe more at this point that like left m-Qube to go on and start other companies and be CEOs or presidents or VPs of different areas. Like it’s, yeah, it’s definitely a highlight in my professional career by a lot.
Keith Cline (52:10)
Yeah, it’s a very important company. It’s m-Qube, WHERE, Endeca, right? Those are where you see just everybody went off to go do extraordinary things to continue to nurture the Boston tech ecosystem. okay, so.
Jeff Glass (52:26)
yeah, lot
of those folks are doing really cool things today in the Boston ecosystem and it’s great.
Keith Cline (52:35)
All right, so what’d you do after that?
Jeff Glass (52:38)
So I was, I told you, I wept in my office for that evening. I then ⁓ worked hard post acquisition to make sure everything went well. ⁓ The Verisign folks decided that they ⁓ would be better off without me post acquisition, which there was no hard feelings in that at all. When you get acquired, it’s tough because
⁓ it’s a little bit like if you were to sell your house to the new family and then they move in and they start changing all the furniture and the carpet and the wallpaper and all the stuff, but you still have to live there. You’re like, no, no, no, that doesn’t go there. No, no, don’t, no, no, no, no, no, no, don’t, don’t do that.
Keith Cline (53:15)
You’re still living there.
Right? That’s a good analogy.
Jeff Glass (53:28)
It’s
kind of like that. And you work really hard to not be that person. You know, it’s like, hey, it’s your company now. You bought it, right? It’s like, but it’s hard. ⁓ It ended amicably. ⁓ And I had done multiple startups in a row at that point. ⁓
And as you’ve heard a little bit from this interview, I was pretty emotionally, I was like, I cannot go start another company. And so I was like, okay, I think I’m only qualified to do one of two things, which is to either start a company or maybe help others who are looking to start companies. And so I made it known to a few of my investors that I was toying around with being a venture capitalist and thankfully,
⁓ a few were kind enough to give me the opportunity and I wound up joining Bain Capital Ventures in 2006.
Keith Cline (54:27)
And you worked with a number of great companies that I certainly recognize. But the one little fun fact that I picked up was, like, I knew Bain was a investor in LinkedIn, but you were a board observer through their high-growth IPO era.
Jeff Glass (54:43)
Yeah, that’s right. So, it was a pretty big check that we wrote, ⁓ at the time it was a pretty large investment for us at Bain Capital Ventures. And yeah, I had the privilege of, sitting on that board, until the IPO, I rolled off at the IPO. And so, I mean, what, ⁓
I’m so grateful for the experience. I aside from the fact that obviously worked out well and the company’s like truly a generational defining company and financially, obviously it worked out great for everybody. But just to have been part of that, you know, in a small way and to, you know, to be amongst the talent that ran LinkedIn and the talent of other investors who are around that board.
I mean, it’s, sort of was the who’s who of Silicon Valley. ⁓ you know, I, I got to watch, you know, was there before and during the recruitment of Jeff Weiner, who was the CEO there for many, many years who, ⁓
like spectacular. I mean to this day, I think about things that I learned while watching him in action and wish I could be more like him in terms of just his enormous capacity to be both big picture and zoom in on detail and his the flexibility of an agility of his mind and ability to create value was extraordinary and like everyone there just it was it was amazing. So that was without question a
a highlight, but I will say it also was the beginning of me thinking I didn’t want to be a venture capitalist forever. And I was at Bain Capital a fairly long time. I was there from 2006 until I was sort of through 2013. And so I was there a fairly long time, but it was actually LinkedIn where I started thinking like, okay,
this is as good as it gets. This is as good as it gets. And it was amazing, but I still didn’t feel the emotional connection and the sense of purpose for me
Keith Cline (56:51)
Yeah, this is the grand slam.
Jeff Glass (57:06)
that I felt when I was ⁓ in the trenches running companies. And so, ⁓ you know, we’re all wired differently. And for me, like the part, the sort of being in the team and, and, and I remember when I, a ⁓ funny story, when I left Bain Capital, I stepped in to, ⁓ to help as the CEO of a company called Skyhook Wireless. And my son was really little. And my son said to me, he said, daddy, ⁓
I told him I had a new job and he said, daddy, are you quitting your job because you’re making to make more money? And I was thinking, yeah, I’m leaving being a managing director at Bain Capital to go work to a relatively early stage startup for the money, for the salary increase. And as I always joke around about entrepreneurship, it’s the
Keith Cline (57:53)
⁓ Right.
Jeff Glass (58:01)
It’s a perfect value proposition, which is you make less, you have a lot more stress and you work much, much harder. But you know, but what, what wouldn’t you want in a job? ⁓ And so ⁓ anyhow, was a great place. I’m, still incredibly close with the Bain Capital team and, you know, Bain Capital is involved in Hometap and, and wouldn’t have traded that experience ⁓ for anything.
Keith Cline (58:30)
Going through your background again. It just brought me down memory lane of Skyhook Wireless which I think I was at like a Mobile Monday event or something and Ted Morgan got up who was the founder of Skyhook and he told this story about getting a phone call from Steve Jobs and he was like Totally like somebody’s you know, just trying to like, you know mess with me here And I think he didn’t take it or someone like that right like wasn’t that the story?
Jeff Glass (58:57)
He thought, I think he
thought it was one of his like college buddies, like Florida Jank. Yeah. Yeah. And I’ve heard the, I, I might even have it somewhere. I’ve heard the phone call. had it record. Fortunately there’s a recording of it. Yeah. I mean, Ted Ted’s amazing. And, ⁓ and what the founders of skyhook wireless, you know, cooked up.
Keith Cline (59:00)
Yeah, one of his buddies or something, totally.
or you have. That’s so awesome.
Jeff Glass (59:19)
⁓ way ahead of its time in terms of recognizing the fact that Wi-Fi could be a way of determining location absent GPS and cell ID ⁓ and in connection with GPS to augment it and to be able to handle dense city areas where tall buildings interfere with GPS or to handle indoor location. And what those guys did as entrepreneurs and technologists was truly nothing short of brilliant. ⁓
And ⁓ it turned out to be a tough space because the big ⁓ wireless, Google and Apple and others, all on this, we’re either going to buy this thing or build this thing ourselves. And so it became so strategically important to mobile devices that it wound up becoming a tricky space for the company.
I mean, I don’t even remember the number, like the number, had hundreds of patents, both domestically and overseas. And the team that built these algorithms, know, our chief scientists, these people were brilliant. was, was, it was extraordinary experience. you know, I was at Bain Capital, Bain Capital had been an investor in Skyhook. Ted had decided that, you know, he was, you know, sort of looking to
sort of step out of as being CEO. He had been in it 10 or 12, like a really long time and just done such a great job. But he was a little bit out of gas at the time. And so one of my partners came to our our partner meeting and said, you hey, we’re going to look around and see Ted wants to bring somebody else in here. Do know anybody? And I was in the early stages of thinking at some point I should go back and and be an operator. And so I
I volunteered.
Keith Cline (1:01:17)
All right, I could go into more of your companies, we gotta talk about Hometap. So, Hometap, how did that idea come to fruition?
Jeff Glass (1:01:26)
So Skyhook wound up doing well. ⁓ We got it growing, we got it profitable. ⁓ We wound up being acquired by Liberty Media. ⁓ I worked there a couple years after the acquisition. I think at some point I became a board member and then I was back to like the same thing that every bunch of years I had to, it like, what do I want to do when I grow up?
And I was ⁓ not convinced that I wanted to go be a startup CEO again. ⁓ And so we started up an entity in partnership with General Catalyst, who had been an investor in previous companies that I was involved with, ⁓ called Starting Five. And the idea around Starting Five is that we would create five companies over five years.
And I and my partner Andy Miller, we would help get these businesses going. We would provide support and strategy. We would be very, very active in the early days. We would help the founding team really get this thing going. We and General Catalyst would put capital into the businesses and we would build these companies. And the first super cool idea that we had, which was Andy’s, was in this area of e-sports. And he loved it so much that he went off to go become the CEO of e-sports.
⁓ and then the next idea, ⁓ which we stumbled into, which was, I had met an entrepreneur in Boston who over lunch was telling me about how he and none of his friends could afford to be able to buy a place in Boston because of the capital required. And two weeks later, a friend of mine over lunch is telling me about how they had just sold their home in Newton because her, the wife’s mom had gotten sick.
⁓ His wife, who is a major breadwinner in their family, had just lost her job. And even though they had all of this equity built up in their home, they couldn’t borrow further against that equity because she had just lost her job. And so in order to fund the care for the mother-in-law, they sold their home completely and rented their place, which it worked out fine. They rented. Turns out the mother-in-law is actually doing well to this day, thank God.
And, they live in a new home now. Like it all worked out fine. But these two real estate stories, you know, hit me in a very short period of time when I was in this sort of mode of trying to think about ideas. And I had said to my wife, Amy, who, by the way, I should give a little shout out to, because like none of this can happen if you don’t have the support of your family. And, you know, we met when we were kids getting laid off of our first job out of college and
Keith Cline (1:04:15)
Yeah.
Jeff Glass (1:04:22)
she has really been the rock. But I said to her, like, if I’m gonna go do this again, I’m not gonna go start another company just because it’s a good business idea. It needs to be more than that. Like, it has to be something really meaningful and purposeful and mission driven. And I started thinking about housing, and then I started researching housing, and I started looking at how bad things have gotten.
You know, people think it all happened during COVID, but it actually, the trend lines that have gone against homeowners have been happening for decades in terms of the cost of homeownership and the pressures against homeowners and the accessibility being more limited. So I started digging in. I was not a real estate expert or a housing expert by any stretch, but I started digging in. I started reaching out to experts. I started trying to understand this world of, you know, residential backed
mortgages and the mortgage world and financing and housing. And what I thought was really interesting is that all of these macro economic conditions have changed over several decades, but yet broadly the approach to helping homeowners hasn’t and the types of products that are available for homeowners is really just minor permutations of existing products. And so we got very, very excited about this idea of like
can’t you democratize more financial options for homeowners? Can homeowners have similar options to what companies have in terms of bringing in an equity partner? Why does everything have to be debt, more debt, or in higher interest? So that was like how it got started. And so we started working on the idea at the end of 2016. By 17, we were really excited about it. And we launched Hometap around this mission to make homeownership
less stressful and more accessible. And we’ve been working really hard since 2017 to fulfill that mission.
Keith Cline (1:06:28)
All right, how do you get it started? Because there’s a lot to this business. One, you need consumers to understand this new type of offering. But you also need the capital to do what is the fundamental foundation of the business.
Jeff Glass (1:06:44)
Yeah, well, every startup’s got its chicken and egg dilemma. ⁓ I would say Hometap’s chicken and egg dilemma was probably ⁓ extra chicken and extra egg. And so, ⁓ yeah, when I started the business, what I originally thought, we thought the hardest part of this was going to be consumer adoption and ⁓ educating consumers on this
because what all that existed prior were loans. And what we’re saying is, no, we’re going to write you a check. And in exchange for this check, we’re going to get a percentage of the future value of the home. And until then, you don’t pay us anything. And so it’s a little bit of like, well, wait a minute. You’re not, what do you mean? I’m not going to pay you anything. And like, what’s the interest rate? Well, there is no interest rate. We don’t charge interest. There’s no accrued interest. It’s all based on, you know,
take the future house value and multiply it by this percentage that we’re telling you it’s gonna be and that’s what it’s gonna be. So we thought the consumer part of this would be the trickiest part. Although we were encouraged because when we started talking to homeowners, what won’t be a surprise to anyone is homeowners desperately want there to be other alternatives to loans
to not having to take on more debt and more interest and having less flexibility and ⁓ less room for error and margin of, so like broadly speaking, homeowners were super positive about the concept, but the concept and putting it in practice are often different. As it turns out, the hardest part of getting this business off the ground was actually the capital side. ⁓ And so particularly in residential real estate where
Investors are used to having the benefit of these mortgages being largely subsidized by the federal government, somewhat insured by the federal government. ⁓ The established capital markets and securitizations existed, rating methodologies, all these things that I couldn’t, back then, didn’t realize how important they were. And of course, in a loan,
you get the as an investor, get the benefit of two big things. One is it’s full recourse, meaning the homeowner has to pay it back. And two is you’re getting interest payments and cash flow along the way. Like those things don’t exist in equity products that. So the capital part was the most difficult part. And it led us to do what isn’t really done ⁓ in the residential financial world, which is we started a fund.
And we started a fund because that’s the only thing I really knew existed, right? I had been a venture capitalist and I had been an entrepreneur who raised money from venture capitalists and they have funds. And so we created a GP LP fund where Hometap was the GP and investors were the LPs. It was small. We put some of our own money in there. And what it led to is it led to this asset manager mentality of really caring about the
quality of our underwriting and our investments and our customer service and our approach to helping homeowners to make sure that they didn’t have problems over time. It led to a, I didn’t know that that was like a differentiating thing. Like, like what else would one do? But it really led to a very different approach that led to a lot of happy homeowners. It led to good performance on the capital side. ⁓
And then over time, like every chicken and egg, you start to figure out how to grow your volume and have more homeowners. And then you get to go back to capital partners and say, hey, we can, we want to take on more capital. And, and slowly you ratchet both sides into something, something very big. The earliest days, aside from a hundred other questions, capital partners would ask us is they say, well, well, we only can write large checks and we’re not…
you and you haven’t proven that that you can deploy a large amount of money. And so we’ll invest once you prove to us that you can deploy a lot of money to which I would say, well, how do I prove to you? I can deploy a lot of capital if I don’t have any capital. And so, you know, that was ⁓ a challenging chicken and egg. And of course, the the biggest both intellectually interesting and biggest challenge of financial products.
Keith Cline (1:11:05)
Alright.
Jeff Glass (1:11:21)
is that you’re like home to have the operating company, right? We’re not the capital investing in the homes. It’s that’s third party capital for the most part. And so the biggest challenge in businesses like ours is like, we’re trying to make sure that a, a fair deal gets cut between capital and homeowner. ⁓ we, we, we tend to be like, our mission is a homeowner driven mission, right? So we want to deliver as much
value as we can to the homeowner. We would like these products to be as competitive as possible relative to their alternatives of loans, both for the mission as well as frankly our business model, but all of that is subject to the constraint of capital, which is if you can’t deliver a sufficient enough return for the capital, then you don’t have it to offer homeowners and then you can’t help them solve their problems or seize their opportunities. And so that is the
perpetual balancing act that that Hometap is, ⁓ is always done. But we’ve gotten to some real scale and we’ve got thousands and thousands of homeowners who’ve given us five star TrustPilot reviews and we’ve helped tens of thousands of homeowners across the US and and we’re making progress, but it’s it’s hard work.
Keith Cline (1:12:43)
And I don’t know if these are current numbers, because I know they are always changing, from whatever press release I saw or something of that magnitude, 24,000 plus homeowners, two billion in home equity investments deployed. So that is scale, so.
Jeff Glass (1:12:58)
Yeah, and I don’t think we’ve released updated numbers post that, but obviously we’re continuing to do more and more every day helping more homeowners. So those numbers are north of that. And it’s very gratifying, right? Like there is, like here’s the problem, Keith. If you think about what it means to be an existing homeowner today, your home.
If you own a home, the good news is your home has likely gone up pretty significantly in value depending on how long you’ve owned it. So that’s the good news, right? You go on to Zillow and you look like a millionaire because your home has gone up in value so much. That’s the good news. Here’s the bad news. The bad news is many, many costs associated with home ownership.
your property taxes, your homeowners insurance, your maintenance, all of these costs go up in connection with your appreciating home value. In some cases, they’ve gone up at a higher rate than your appreciating home value. And those are real out of pocket costs today. The appreciation on Zillow,
is a paper, it’s a digital appreciation. It’s not even paper. You can’t even put it back in the file cabinets that we sold back in the 1980s. so, increasingly, if there was a metric for what it means to be house rich and cash strapped, like every day, the US is hitting a new record of the number of homeowners and households that falls into that bucket.
And so what is needed is a broad suite of financial innovation, ⁓ not just the product we offer. There’s a whole bunch of things that will eventually happen to deal with the realities of homeownership today and help take some of the pressure and the stress off of homeowners, make it easier for people to move from being renters to owners, make it easier for people to own a house and actually have a life at the same time, make it easier for people to seize
opportunities, whether it’s fund small businesses or pay for their kids college or renovate their kitchen or deal with the challenges of like my friend whose mother-in-law was sick or you’re dealing with health emergencies or divorce or credit card stuff that got out of whack. Like we need solutions for that. And then at the other end of the spectrum of lifestyle home, like we need to build solutions that allow people to retire in place. Like what do do when your income’s gone down, but your property taxes keep going up or
your homeowners insurance keeps going up or the maintenance on your house is going up. like loans are a very good, smart, clever solution for many situations and many homeowners. But just like we’ve seen in non-residential real estate, like there’s a place for equity-based solutions ⁓ and combinations of debt and equity-based solutions.
And that’s what needs to happen to help help American homeowners. And frankly, this is a problem that exists beyond the U.S. borders.
Keith Cline (1:16:08)
And how it works, to put it simply, is Hometap will provide an estimate. There’s an application process, there’s a closing, then there’s wiring of funds. That’s kind like your four step process on your website. Now, the terms, it’s like, hey, we’re gonna take a agreed upon percentage of your home sales price or appraised value upon that transaction. So if I agree to Hometap for whatever percentage of equity of my home,
If I sell my house seven years later, it’s already predetermined what percentage that is and then what is ultimately going to be Hometap’s.
Jeff Glass (1:16:43)
That’s right. So
if, if we were getting 10 % of the home value and, uh, you know,
Seven years from now, you sell your home or you refinance us out or you buy us out in however way you want. Right. There’s no restrictions on how you do it or there’s no prepayment penalties or anything like that. So it’s X years out and your house is worth $700,000, which is about where we are on average nationally. So you’re, you so, and we’re entitled to 10%. So you would, you would, we would get $70,000.
at that point in time off of the settlement of the investment. And so you know today what that percentage is. What you don’t know is what the house is going to be worth. But that’s based on the sale price or an appraisal at the time of when you settle with us.
Keith Cline (1:17:37)
But it’s also, there’s like a 10 year term limit of, hey, I’m not gonna sell my home. Well, Hometap just can’t be hanging out for eternity.
Jeff Glass (1:17:47)
Yeah, this is an interesting question because there are 30 year products on the market. There’s 10 year products. There’s actually stuff in between just like the lending market, right? There are a variety of different terms. You can get a 30 year, you can get a 10 year, you get a one year, one year mortgages you could get. So it has some similarities to that. ⁓ For us, we decided, ⁓ even though it’s a little bit of a sacrifice, meaning like if a homeowner comes to us and says, hey,
I think I want capital for more than 10 years. You know, we’re quite overt and saying, well, you know, we can only guarantee you this money for up to 10 years. ⁓ It’s possible at the end of 10 years, you could refinance it or roll into some other stuff, but we can’t make that guarantee today. And so those folks will largely ⁓ not use us. They’ll go to competitors and take alternative products. But we made that decision because by having ⁓ by focusing on people who have
of
short to medium term capital needs. It just allowed us to make the product a little bit less complicated, which is this, what we call this X for Y idea, which is we’re gonna give you X amount of capital and take Y percentage of the value of the home. If you, the longer you make the term, the more…
buckets you would need to have over the course of those 30 years in order to be able to attract capital who would then be taking the risk that somebody takes the capital and doesn’t settle with them for up to 30 years. And as you know, right, like a dollar 30 years from now is worth significantly less than a dollar today. So the math on that just gets more complicated to do that. I would imagine at some point we’ll figure out some
know, way to do that for those homeowners who today they just don’t pick us to try to be able to offer something longer. But for now, we just decided we’ll focus on a segment of homeowners, which is.
frankly most because most of our homeowners have already been living in their home for seven or 10 years. And so, and most people don’t stay in their home more than 20 years. Most don’t stay more than seven or eight years. And so we just decided that this particular product is focused on folks who really are looking for medium to shorter term capital. Not that 10 is short, but medium term capital.
Keith Cline (1:20:19)
Now you did announce back in December a $50 million investment. So what’s next for Hometap?
Jeff Glass (1:20:26)
We have a lot to do. ⁓ We are looking to broaden our product suite. our product is called an HEI, a home equity investment. Our mission isn’t to be the world’s best HEI provider. I think we are, but that’s not our mission. Our mission is to make home ownership less stressful and more accessible. And so we have a broad vision of
of transforming capital into solutions
in order to enable homeowners to solve their challenges and seize opportunities. And so we want to expand our product suite across the life cycle of homeowners. We want to be able to partner with a broad set of players in the space where the right product is offered to the right homeowner independently of whether it’s debt or equity. So we’ve got a lot to expand on in that dimension. We want to expand into
more states in the United States. We continue to make very, very sizable investments in technology to be able to enhance the customer experience, to be able to deliver capital for them faster, to be able to make ⁓ the user experience easier, to try to offload some of the administrative work that they don’t like ⁓ onto us so that we can help take care of that for them. So there’s a lot that we’re investing in on that side as well.
Keith Cline (1:21:57)
Well, it’s an exciting future ahead. this is another ⁓ formation of an anchor tech company in the Boston tech scene. ⁓
Jeff Glass (1:22:06)
We’re
working hard.
Keith Cline (1:22:09)
Outside at work, what do you like to do for fun?
Jeff Glass (1:22:11)
What do I like to do for fun? I mean, I like to work for fun. I’m a pretty avid Peloton rider. So I’m kind of on a little bit of a break, but I have gone through periods of time where I have ridden my bike every day for 365 days. So I can be quite focused on that dimension.
Keith Cline (1:22:35)
Wow.
Jeff Glass (1:22:40)
I, ⁓ I over the last bunch of years have been
doing a lot of reading around mindfulness and kind of the intersection of neuroscience and mindfulness ideas. And so I like it personally, I also like for me personally to help with my mental health. But I also really find it fascinating intellectually about how like neuroscience today is validating through scientific discovery stuff that, you know, folks thousands of years ago that Buddhist monks were preaching.
And so I just find that really, really interesting. And I spend a lot of time reading about that. ⁓ I love playing basketball. I continue to work on my free throws, even though I will likely never play in an officiated basketball game ever again. But you never know. And games are won or lost on the free throw line. I find shooting free throws is a very meditative
thing to do. I really love basketball. That’s probably my favorite thing to do. And I’ve got three adult kids. And one of the things that has been incredibly rewarding for me is figuring out how our relationships evolve as they become adults and build their careers. And so I try to spend as much time as I can with my kids and my wife and be a good dad and good husband.
Keith Cline (1:24:11)
Very cool. Well, Jeff, thanks so much for taking the time to walk us through your background story. Obviously all the great stories behind the companies you’ve been building and obviously all the great work you and your team are up to at hometown.
Jeff Glass (1:24:22)
Well, this was a lot of fun and some of those screenshots from companies of long ago were definitely blast from the past. So thanks, Keith.