Episode 421 of The VentureFizz Podcast features Harris Stolzenberg, Partner at Pear VC.
I spend a lot of time on LinkedIn and in my travels, I love discovering individuals who are local to the Boston area but are perhaps working for a meaningful company that is headquartered elsewhere.
This is what happened when I stumbled on Harris’ profile – I stopped and thought to myself… wait, Pear has an investor in Boston who is leading the firm’s expansion to the East Coast? No way – game on and off I went to connect with Harris and ultimately bring you this interview!
Pear is a west coast pre-seed / seed stage VC firm which has invested in over 200 companies like Doordash, Gusto, Vanta, Dropbox, and many more. The firm also offers an exclusive, small batch accelerator program for pre-seed companies called PearX.
In this episode of our podcast, we cover:
- Harris’s best networking advice plus tactical tips.
- His background playing lacrosse at MIT, and the incredible story of how he raised money for the Boston Marathon bombing victims which even led to a personal donation from Oprah.
- Getting his start in investment banking before moving into the startup world at Pando and eventually landing his first role at Pear.
- The story of Flock, the company retreat platform he co-founded, its eventual acquisition, and the hard-won lessons he took from that experience.
- His transition back to the East Coast and his time serving as Chief of Staff at Pillar VC.
- His current role at Pear as a Partner, the firm’s approach to investing, and all the details on how the PearX program works.
- Harris’ thoughts on the Boston tech ecosystem.
- Plus, so much more!
Transcript
Keith Cline (00:01.286)
Harris, thanks so much for joining us.
Harris Stolzenberg (00:03.17)
Thanks for having me, I appreciate it.
Keith Cline (00:05.32)
Likewise, yeah, just in my LinkedIn travels, I always just discover things and I was like, Pear has a partner in Boston. So I had no idea. Yeah. So I was just like, wait, this is good. Because I like it when I see West Coast VCs having someone local to Boston. And then when I was going through your LinkedIn profile, was like, oh, I see all the connections here. So I was excited to talk to you about your background, what you’re up to at Pear. But before we get into that,
Harris Stolzenberg (00:16.322)
Meh.
Keith Cline (00:34.77)
You know, we’re recording this in February, so there’s a lot of college students that are, you know, maybe looking for a job or maybe they’re founders raising capital. So the advice I wanted to kind of just pick your brain a little bit on is networking and the importance of networking and building relationships. So being that you interact with a lot of students, like what advice would you pass along to those individuals around building and networking and building those relationships?
Harris Stolzenberg (01:02.722)
Yeah, it’s a great question. It’s timely because I was actually just at the HBS VCPE conference two weekends ago and I was on a panel and this was kind of the topic of how do you break into VC and how important is networking and all of that. I think it’s very important but I think you gotta do it in the right way. If you look at my inbox or my LinkedIn, you
10 times a day, I’m getting someone in my inbox asking, hey, can I grab a quick coffee? Can I pick your brain for 15 minutes? And look, I’d love to say yes to everyone, but I’ve learned in this job, like a huge part of it is gatekeeping my time just because I need to be meeting founders and I’m evaluated from my boss and I need to save time to do my job. So the best way to kind of get someone to say yes is…
to give first before you ask for something. So I’m much more likely to say yes when you’re doing these kind of networking out bounds. If you say, I was on MIT’s campus and I’ve talked to 10 founders and I think these are the two best ones and do you want an intro? I’m much more likely to engage with something like that than like, hey, let’s get in a call for 30 minutes. That’s tough for me to say yes to. So breaking into VC, breaking into any job is so difficult these days.
Keith Cline (02:09.372)
Right. Yeah.
Harris Stolzenberg (02:20.558)
You need to put yourself out there to maximize your chances of getting lucky. But a lot of times a lot of networking goes kind of unnoticed until years down the line there’s kind of this magic moment when somebody you talked to a while ago has an opening and they remember you and you never know. So I think it’s important to do. But sometimes it takes a long time to pay off.
Keith Cline (02:44.456)
Yeah, and get out there, right? There’s all these events on campus. And if you plan ahead and you see someone like Harris speaking at an event, there’s gonna be an opportunity at the end of the panel to go up and just shake your hand for a quick second. And then just politely ask, hey, do you mind if I send you an email? And at that point, the person’s probably gonna respond, because they met you, right? Just the cold outreach, it’s really hard to break through that.
That’s how I got started in my career when I started my own company. was like, I went to all the events and, but I would, you know, have a good elevator pitch to gravitate the person towards like saying, okay, yes, I will respond to your email. So you gotta work on that too. And then just the point of being respectful of others people’s time is so I think critical too. A pet peeve of mine is the warm intro.
If the person’s making the warm intro and they don’t give me the courtesy heads up ahead of time, that is the worst. I’m like, man, really? And I always take the call because it’s just the polite thing to do. But I’m like, just always ask the people. Once you make that connection, it should be already both parties know that, hey, we’re going to talk. anyways, that’s my pet peeve for today.
Harris Stolzenberg (04:00.93)
Totally. think there’s some like rare like exceptions where like if some of my best friends or best founders I work with intro me to someone, I’ll say yes. But for the most part, I totally agree. Like a double opt-in is always nice.
Keith Cline (04:08.421)
Yeah, of course. Right.
Keith Cline (04:14.299)
Yeah, all right, so let’s talk about your background story. So where’d you grow up? What were you like as a child?
Harris Stolzenberg (04:20.278)
Yeah. So I grew up in South Florida. I always say Fort Lauderdale because a lot of people, you know, know Fort Lauderdale. They probably went on spring break or something there, but it’s a small town called Weston is actually where I grew up. Like 45 minutes west, right near the Everglades. Very, you know, small town. Not that small, but like very like quaint. Like, you know, there’s like sports and school and suburb basically is what it was.
I was the oldest of three boys, played sports growing up, school was always important. But yeah, that was kind of me. to high school, same thing kind of held true. Played football in lacrosse and took school seriously and then somehow got lucky to get into MIT and went from South Florida up to Boston.
Keith Cline (05:13.297)
So I always wonder, how does one get into MIT? Did athletics help you? Obviously, you’re a good student. That goes without saying. But there’s lots of good students applying to MIT. So what do you think was the?
Harris Stolzenberg (05:24.748)
Yeah, yeah. So like when I was going through the whole recruiting process, know, all the IVs, the way it worked is like, as long as you hit a minimum bar, like, they wanted you, you kind of get to skip admissions and you get in. So I think that’s where there’s like that stereotype. If you play a sport, you know, an IV, like maybe you had a little bit of an easier path. At MIT, it’s not like that. Like if they say they want you, it’s kind of like they want you to apply to MIT and you have to get in like everybody else. I think there is kind of like a…
You know, it helps to have an athletic letter of recommendation, but it’s not like any way in the same thing as some of these other schools. So I didn’t know if I was going to get in or not. You know, frankly, when I went up and visited and it was freezing coming from South Florida, I was like, you know, I don’t know if I’m to be able to handle this. But yeah, once I got in, it was kind of a no brainer to go.
Keith Cline (06:15.686)
and then you continue the athletics. So you played lacrosse, which I was going through some of your stats, very impressive, New Mac Athlete of the Year for lacrosse.
Harris Stolzenberg (06:25.216)
Yeah, I was definitely a much better lacrosse player than I was football. Growing up in South Florida, like football was like the biggest thing. Like I grew up like down the road from this high school called St. Thomas. It’s just like always the best, you know, football high school in the nation. They’ve got a ton of NFL players and I grew up going to Dolphins games. I love playing football, but genetics caught up to me eventually. And, you know, being my size as a slot receiver, you know, I could only do so much. So
Yeah, took lacrosse seriously and had a blast playing at MIT.
Keith Cline (06:57.234)
Yeah, I can relate. Played football in lacrosse in college for Nichols College, a Division III school too. And after my sophomore year of football, I’m like, I’m not built for college football. Like, I’m never gonna see the field here, but this was a long time ago before lacrosse is what it is now where so many kids play it. It was all walk-ons. We’re all football and hockey players. They were like, wait, we can whack each other with sticks? This is cool. So I did four years of lacrosse just as a…
It’s fun. I wouldn’t say we were the most talented team, but we had lot of passion.
Harris Stolzenberg (07:30.828)
Yeah, we weren’t the most talented either. I wish we were at MIT, but I think school always came first. And it was funny, like, going to the games, everyone’s like doing homework, the whole bus ride there and back. And I’m like, guys, like, let’s focus on the game. And everyone’s like, well, we got all these PSETs to do. So anyway, it was a unique experience, but I want to change it for the world.
Keith Cline (07:52.969)
All right, and then you raised a lot of money for the victims of the Boston Marathon bombing. So how did that come together?
Harris Stolzenberg (07:59.649)
Yeah. Yeah, when I was a senior in high school, I had gone into MIT. Like, I got my acceptance letter. I knew I was going to be going up to Boston. And that was the year that the bombings happened. And, you know, I want
to do something to support the new city I was going to be going to. because of the bombings, a lot of people lost limbs. And my brother happens to be a quadruple amputee. He got sick when he was younger and had to have both his hands and both his feet amputated. Anyways, like, you know, he played sports in high school. He drives. He’s 100 % self-sufficient. He’s like the coolest person I know. And he’s been like that, you know, his whole life. So we just wanted to show those folks that, you know, they are going to get prosthetics.
Keith Cline (08:35.112)
That’s awesome.
Harris Stolzenberg (08:42.032)
and learn to figure things out just like he did. So we started with like, we’re gonna set up a bake sale at school and raise a couple hundred dollars. And that was really the plan. And then the local newspaper got ahold of it. And eventually we were on like CNN, CNBC, and it just kind of spiraled from there and ended up raising a bunch of money, including Oprah called us and donated $100,000, which is pretty cool. Yeah.
I didn’t know who it was. I didn’t know who it was. My mom was like on the phone. She’s like, oh, it’s Oprah. And I was like, who’s that? And she starts laughing and Oprah is laughing. And it was pretty funny. Yeah.
Keith Cline (09:15.656)
What?
That is amazing. Yeah, you got on the media outlets. That’s amazing too. And then you’re like, getting calls from Oprah. That’s okay. That story was even better than what I imagined.
Harris Stolzenberg (09:30.254)
Yeah, it was great. Well, the thing I was promising is that like, you know, for the fundraiser, I said I was going to run the Boston Marathon, like going to this new city. I was going to be a freshman in college. We had already raised like a hundred grand at this point. And someone was like, asked me, well, how are you going to qualify? I was like, oh, I didn’t even know I had to qualify for the Boston Marathon. I thought you could just like sign up and show up. eventually you had raised enough money that like there’s like a couple of charity exemptions you can get. And one of the teams was nice enough to let me run with them. So I spent my
Keith Cline (09:48.42)
Right.
Harris Stolzenberg (10:00.181)
whole freshman year waking up at 5 a.m. running around the Charles River, going to class, going to practice. It was a grind, but I finished and it was definitely my proudest accomplishment, I would say.
Keith Cline (10:12.616)
Wow. Hearing that story alone, I would hire you for anything. Speaking of hiring, how did you get your career started?
Harris Stolzenberg (10:17.678)
There’s a lot of things I wouldn’t hire myself for, so I appreciate that though.
Harris Stolzenberg (10:26.988)
Yeah, so I started off doing tech investment banking. So I knew I always wanted to do something entrepreneurial.
But, you know, coming out of college, I wasn’t a software engineer. Almost all of my friends were going to work at, you know, Google, Apple, and that wasn’t for me. But I knew I wanted to be around tech, and I kind of had like a finance background. So I started off doing tech investment banking. Loved learning about all the tech companies we were covering, but like did not love the whole kind of banking culture, and I didn’t really think I was learning that much either. So yeah, started off doing that. I definitely learned how to work hard. But after about a year and a half,
I was like I need to get to San Francisco where the action was so I actually like transferred divisions from Boston to SF was there for a little bit longer and then was like you know what you know work in a hundred-hour weeks I’m not gonna find like what I my calling so I kind of quit cold turkey when I was in San Francisco and was lucky enough to end up at a five-person Startup and I can talk more about that, but that’s kind of how my Yep, this is Pando exactly
Keith Cline (11:28.444)
Yeah, so this is Pando. What was Pando, or is?
Harris Stolzenberg (11:33.655)
Yeah. I was, look, I was, I had quit my investment banking job. I was like with some friends in San Diego on a beach, like saying I’m going to take, you know, a couple of months off and just like detox from that whole investment banking experience. And I was happened to be on LinkedIn and saw a really cool post. It was sports related. was like, Hey, we help minor league baseball players kind of hedge their future because, know, most minor leaguers never make it to the majors. They never make any money, but a couple do. And you don’t really know who those are going to
be at the start. So why not all form this pool where, you know, 10 minor leaguers all agree we’re going to contribute some percentage of our future income to this pool and then everyone gets it. And I was like, wow, that’s so cool. It’s like an insurance product with sports. And I was like, hmm, like, does this extend outside of sports? Maybe to founders like, you know, I have a bunch of friends who are going to be founders and some get lucky and make a lot and others are just too smart. They just don’t, you know, get lucky. And maybe I could see myself doing this potentially. So like, this is a really cool idea. So I applied.
Keith Cline (12:15.816)
That’s interesting.
Harris Stolzenberg (12:33.489)
Heard back from the founder, his name’s Charlie Olson. He went to Stanford GSB, really great guy. And I was like, I could learn a lot from this, and I think the idea’s super cool. So I was lucky enough to get the job. I was the fifth employee. Turned out their office was right outside of Stanford at a local VC shop called Pear. So that’s how I got to know Pear for the first time. I had no idea what really early stage venture was or who Pear was. But yeah, I started off in like
finance role, which is funny because like you know most startups you don’t really need you know finance role so everyone was kind of learning on the fly and eventually my title switched to chief of staff where I was doing everything from recruiting, product, sales, know really whatever they they needed me to do and I just kind of caught the startup bug from there.
Keith Cline (13:23.378)
The emergence of the chief of staff role has been interesting to watch over the past few years. It’s become like a major thing. And I think it’s such a phenomenal opportunity for people that want that broad exposure. Maybe they’re thinking about starting a company. I mean, that’s a great segue of learning what it’s all about.
Harris Stolzenberg (13:39.929)
Totally, I think it’s a great role under like…
I think sometimes companies hire that role too soon. I think if there is product market fit and you can get the job as like chief of staff, you should absolutely get it. Like you’re gonna learn so many different things. They kind of just throw you at whatever kind of the biggest problem is at the time, you know, in the organization and you’re gonna learn and you’re gonna figure things out. So yeah, if you can like get a chief of staff role at a fast growing startup or, you know, even at a venture fund, some have them now. Highly, highly recommend doing it.
Keith Cline (14:15.528)
All right, so what’d you do after your startup experience there?
Harris Stolzenberg (14:18.755)
Yeah, so I was there for a little bit over a year and I was like, you know what? I’ve learned a lot. It’s time for me to try to start my own company. So I left. I was playing around with a few ideas. I was emailing Mar, who is a GP at Pear.
And I had gotten to know her because I worked out of the same office and, know, through lunch and just like introductions from, from Charlie that the CEO of Pando, I just formed a relationship. So I was like, Hey, what do you think about X, Y or Z idea? And eventually we ended up meeting and she’s like, Hey, I don’t really think you’re onto anything right now, but like, I do think you could be a great founder in the future. We had this role at Pear open up for an associate. Like, why don’t you try the venture thing first? And you know, when you’re ready, you can go start a company. So I was like, it makes a lot of sense. Like, I feel like I could learn a lot seeing how.
VCs think about startups from the other side. You mentioned networking and getting jobs. We talked about that at beginning. I kind of networked the old fast. I didn’t even realize I was networking. I never wanted to get into venture. That was never the goal. Just because I had formed a natural relationship with her and she’d gotten to know me over a year, she felt comfortable basically offering me a job without me having to apply. So yeah, that’s how I got into Pear.
Keith Cline (15:34.492)
That’s the best way for it to happen organically. And yeah, those relationships just, it’s such an important thing. That’s why I just try to hammer that home to, like have two girls in college and I just tell them networking, networking, networking, relationships, relationships, relationships. So, all right, so you’re an associate, so you’re actively looking for deals, like companies to invest in.
Harris Stolzenberg (15:54.714)
Yep.
Yep. Spent a lot of time at Stanford and Berkeley. Like at the time that was their bread and butter. mean, a couple of years prior, they had done the DoorDash deal out of Stanford, which kind of put Pear on the map. So they, you know, doubled down on what they called like their dorm strategy. And I was helping kind of run that playbook. And it was awesome. I just got to talk to just like smart, ambitious people all day that, you know, we’re trying to start big companies. So I learned a lot. I learned a little bit about how early stage venture worked. you know, eventually though, when you talk to enough founders,
and you’re young and ambitious, you start to catch the founder bug yourself. So after a little bit over a year, Pear, that’s kind of what happened. So I decided to start my own company from there.
Keith Cline (16:38.633)
All right, so let’s talk about your entrepreneurial journey. So this is Flock.
Harris Stolzenberg (16:42.903)
Yeah, this is flock. So it wasn’t always flock. So actually before we started the company, I wasn’t, I was very happy at Pear. was planning on staying for, for a little bit longer than, you know, just over, just over a year. But two of my best friends from, from MIT, one was a software engineer at Apple. The other was a PM at Uber. They called me one night and they’re like, Hey, we’ve got this, you know, YC interview tomorrow. We don’t know what we’re going to pitch. Do you want to be CEO and come pitch something? I’m like, guys, this is the weirdest conversation. What do you mean? Like, you don’t know what you’re.
pitching, like you want me to be CEO, like I was like, all right, like I’ll, I’ll, we’ll show up tomorrow and we’ll come up with something. we like stayed up all night, put together this idea for like a, you know, software procurement platform. I don’t know. It sounded good. Basically, you know, every, every company has hundreds of different softwares they buy. Like maybe we can figure out a way to, you know, help them, you know, buy at a discount or something like that. Yeah. So it, it existed. I didn’t really exist at the
Keith Cline (17:35.869)
Yeah, that exists. Vendor, Vendor’s a company that does that and there’s a handful.
Harris Stolzenberg (17:40.815)
So we were, think, we pitched that idea before, right around when Vendor was getting started. anyways, we get in, we work on that idea for a couple weeks and realize we’re not having fun doing it. We want to do something else. So the advice we got at the time was go talk to a bunch of…
companies figure out what their problems are and go solve that. So this is like as COVID was ending, we were doing these customer discovery interviews and we realized like everyone had given up their office space. They were like remote or hybrid. They needed like a way to bring their teams together in person for like these off sites or retreats. So we heard it over and over and having just worked for a year in venture, I told my two friends, I’m like, Hey, I know we’re hearing this as a problem, but the market for this is really small. It’s like venture backed startups. Like there’s not that many of them. And like
I don’t know if you can really solve this problem like with a hundred percent software like there may need to be some human in the loop and that’s not really like a great venture company, but Problem with having you know two other co-founders three founders total is there’s a vote and I lost the vote So we went down that direction and the worst thing happened we like grew like a million dollars in revenue very quickly So I was never gonna convince them to change the idea because in their mind it was working But in the back of my mind I knew like look we’re throwing a lot of humans at this problem
and we’re eventually gonna run into the wall of the market just not that big. when people saw us be successful, like six months later, we had four other venture-backed competitors raise money when there should have probably never been any venture-backed companies in the space. So it was a cool learning experience. Like, look, we got some real revenue, we were profitable, we built a team, we built some software and we sold the company, but it was more of, I’d say, like a starter business than a true VC rocket ship. Yeah.
Keith Cline (19:19.785)
Totally. Yeah.
Keith Cline (19:33.386)
So I look at these company retreats and I’m like, that’s a lot of planning. know, because you just look at the pictures, like everything was so beautiful and these excursions and the meals and the, you know, the talks and the sales kickoff things. I’m just like, these things cost a fortune. Like, the logistics and I’m just like, that’s a heavy services business right there. That’s like, even though, hey, we’re automating something with software. It’s like still.
Harris Stolzenberg (19:38.916)
Yep.
Harris Stolzenberg (19:50.071)
Yeah, they do.
Keith Cline (20:01.225)
caring and feeding your customer constantly. And then you’ll get those customers that probably weren’t really happy. those one occupy. Right.
Harris Stolzenberg (20:08.099)
Those are the words. And I, the CEO, I’m the one that gets to deal with them and they want refunds. I, know, it gets very complicated, but I’d say for the most part, you know, 90 % of our customers were very happy, but you always remember the 10 % that weren’t. And yeah, very human, you know, relationship. You mentioned relationships, how important they are. Like, you know, people really just wanted to work with us for our people and the planners they had worked with in the past. you know, that’s a great…
Keith Cline (20:21.565)
Yeah. Right?
Harris Stolzenberg (20:38.765)
That’s one type of business, but it’s not kind of that business that’s going to grow with high margins. So yeah, we put together a solution that people wanted, and we made some money. But there is kind of a finite limit you could hit with doing that.
Keith Cline (20:53.907)
So what was your most memorable event during that stretch?
Harris Stolzenberg (20:58.255)
That’s such a good question.
I went to one in Austin, Texas for a client. It wasn’t actually even like a tech company. It was like a political group actually, you know, hired us and it was just very extravagant. I remember like going and I went with one of the planners who planned it just to like be a fly on the wall and, you know, see everything kind of that went into it. And, you know, there was a little bit of everything like, you know, barbecue from one of the best barbecue spots in Austin, like, you know, some, big parties, mechanical.
bowl, a little bit of everything. So yeah, it was just a really fun time. We did events in like 30 countries, so like there was a lot of people on our team traveling, you know, everywhere. But yeah, that life feels like a long time ago now.
Keith Cline (21:50.98)
but the company did sell.
Harris Stolzenberg (21:52.983)
Yeah, so we basically when we realized like,
You know, we were only growing so quickly and things were kind of stalling. I think the rate of learning for me, my co-founders, you know, was going down. But we had a profitable business that, you know, some people, you we thought would be interested in. So we reached out to all of our competitors, a lot of which had raised venture dollars. They didn’t have the money that, like, we wanted to be able to acquire us. But through kind of a stroke of luck, one of their investors happened to be like have their own like little
family office that bought a lot of different travel companies. So we kind of went into diligence with them and it was my first time ever really like selling a company and it worked out. So they bought it and it’s still operating to this day.
Keith Cline (22:42.537)
So, biggest takeaways from that experience overall.
Harris Stolzenberg (22:47.528)
Ooh.
if you’re trying to build a $10 billion company, the market size really matters. So like, think about that. but also like, look, I don’t know how much of it I would change. Like I learned so much. think there’s a lesson in just like, get started, do something like you’re going to learn things along the way. And that was definitely the case of what we did with Flock. And then also I’d say start a company with someone or people that you like trust immensely, but also like view as, an equal. So one of my co-founder Jared,
You know, we talked every day on the phone and I think starting a company by yourself is incredibly lonely and difficult. So I think having a co-founder made it a lot easier.
Keith Cline (23:30.281)
Alright, so what’d you do next?
Harris Stolzenberg (23:33.135)
Yeah, so I wanted to start another company. My other co-founders were a little bit burned out. So I was like, all right, I got to go find a job.
I had moved back to Boston at the time. I had spent some time in San Francisco, a little bit of time in New York, but I just miss Boston. feel like I could do my best work in Boston during the week. Boston’s great for just focusing, and then you can also have some fun on the weekends. And I just felt at home. And the place I went to college, I saw a lot of friends around. Anyways, I knew I was going to stay in Boston. So I called Mar, my old boss, my old now, and she invested in our company, Flock.
hey, I’d love to come back to Pear. She said, that’s great, but you’d have to move back to San Francisco. And I said, that’s not on the table. So I was lucky enough to find a job at Pillar VC. And they were amazing. It was a little bit outside of what I was used to. They do a lot of deep tech, biotech, some software as well.
But I hadn’t done much in deep tech or biotech, so was very cool to learn about that. They gave me a shot, and I absolutely loved my time there. And as a result of being there, learned a lot about the Boston tech ecosystem, both MIT, Harvard, and the rest of it. So yeah, I was very grateful for my time at Pillar.
Keith Cline (24:56.746)
Yeah, is a great firm. I interviewed Jamie when he was just starting. He was in a shared space, just starting Pillar. Well, you know what? Sadly, it was before I started podcasting. I did a written article, kind of profiled his background. We needed to do an audio version because this was, I don’t know, they’ve been around for like 10 years now or so. So was a long time ago. But yeah, amazing firm. Just a…
Harris Stolzenberg (25:06.905)
No way. I gotta watch that. You gotta send me that interview. I love that.
Harris Stolzenberg (25:15.477)
No way. Okay.
Harris Stolzenberg (25:21.549)
Yeah. Yeah.
Keith Cline (25:25.418)
Great anchor VC for Boston. Okay, then you ended up back at Pear. So how did that come to fruition?
Harris Stolzenberg (25:32.173)
Yeah, so I was happy at Pillar. I wasn’t planning on leaving. And then, you know, out of the blue, Mark called and was like,
Hey, I think I got it wrong. think like we do want someone in Boston and we’ve known you for so long. Like you’d be the perfect person to run it. And I think the reasoning is just like, you know, there’s been Cursor, there’s been McCore, Mock, I mean, there’s so many big companies coming out of Boston. And if you’re a tier one kind of VC fund, you should probably have some boots on the ground. And yeah, for me, it was just kind of a no brainer to go back to Pear
them.
You know, I’d worked at a Pear portfolio company. I had worked at Pear. They were investors in my startup. So it was really like a full circle moment. you know, Mar is really like a force of nature. I mean, I start maybe my day at like 8 a.m. and I already have five emails from her from 4.45 a.m. in San Francisco. She’s an absolute, you know, machine and just a joy to work with. And I learned so much from her. So, yeah, it’s been a great decision. I think I’m like seven or eight months in now.
and just having like the time of my life, yeah.
Keith Cline (26:44.842)
Now you’ve given a couple elements of the firm, but I think it would be helpful just to kind give more of that broader, here’s who we are, what we do, fun size and check size, know, like just the basics.
Harris Stolzenberg (26:54.275)
Yeah, yeah.
Yeah, so Pear has been around for 13 years. A lot of people know Pear as one of the first investors in DoorDash. I think that’s what put us on the map. Now we’re on our fourth fund. It’s 432 million. So pretty big for like a pre-seed and seed stage firm. That’s kind of where we focus. We’re generalist investors. So whether founders are building in, you know, AI, B2B SaaS, consumer, fintech, healthcare, biotech, deep tech, robotics, it doesn’t really matter. All we care about is you’re trying to build like
category defining massive company and in every one of those verticals I mentioned almost all of our team are former founders that have started and sold companies in those spaces. So I think that’s something you know unique is the amount of operator and founder experience that we have and then we can write checks anywhere from like a hundred K to six million so kind of across the board but I try to focus on we have this program called Pear X it’s like our YC competitor it’s a little bit different or it’s like you know I
I like to say apples and oranges. We’re only 25 companies twice a year versus 150 companies four times a year. So if there’s 12 partners, every partner works with one to three companies. So we go really, really deep. And it’s not just like when the program ends and you go to demo day and you raise your seed, we forget about you. We’re a smaller fund, at least comparatively to the other ones. So you’re a para portfolio company for life. We work with you. We’re a true early stage fund.
in that regard. So I’d say those are kind of the key differences.
Keith Cline (28:30.238)
Yeah, cause like, Y Combinator Like what? Is it four cohorts a year now?
Harris Stolzenberg (28:34.253)
Yeah, now it’s four cohorts a year. It’s like 150 people, companies per cohort, 600 companies a year. So they’re definitely going with the, you know, spray and pray approach. And look, I think there are some merits to it. I think their returns speak for themselves. I think it’s a great brand. Look, I was a YC founder, but not everyone wants to be kind of in those massive cohorts where they’re, you know, a little fish in a big pond. I think the nice thing about Pear is we really go deep.
Keith Cline (28:39.743)
Wow.
Harris Stolzenberg (29:04.297)
with like the smaller amount of teams that we take. So yeah, it works for us and I think their model works for them.
Keith Cline (29:13.706)
All right, not that we’re gonna talk a lot about Y Combenator but I just wanna test your Boston Tech knowledge. Do you know where their first cohort was started?
Harris Stolzenberg (29:18.073)
Yeah.
Harris Stolzenberg (29:22.177)
Yeah, yeah, Cambridge, Mass, I’m pretty sure. I’m pretty sure Paul Graham and Jessica Livingston. Yeah, yeah. Near MIT, I want to say. I could be wrong.
Keith Cline (29:24.148)
Do you, you, it’s correct. Yes, so.
Yeah, was, think, in that general area. So he had a company that sold in Boston. Vioweb, I think is the name. Do you know who was in that cohort?
Harris Stolzenberg (29:34.178)
End of.
Harris Stolzenberg (29:39.247)
I think that’s right.
Harris Stolzenberg (29:43.971)
Ooh, I don’t know, but I do know some of the earlier cohorts were like, think Sam Altman was in them. Maybe like Brian Chesky. I don’t know if Brian Chesky was in that one. They might have been in the later one. Coinbase was early, but yeah, Reddit. Okay, cool. And now 776. Yeah, very cool. Yep, Twitch. Yep, nice.
Keith Cline (29:51.167)
Yes, he was in the first one in Cambridge. No, yeah, no, yep. Alexis Ohanian.
Reddit was, yep. And Justin Khan.
So, I mean, was others obviously, but just like those three people somehow were in Cambridge working on startups. the first, yeah, like Reddit was started and I think they were physically located, like they were living in Charleston or something like that, like Charlestown, some of it, like, I don’t know. But anyways, fun fact, fun fact. Back to Pear So, you’re spending a lot of time going to all the academic institutions, obviously MIT, Harvard, but also
Harris Stolzenberg (30:15.277)
And we let them go. And now there’s that stuff.
Keith Cline (30:37.853)
Up and down, like Penn, Brown, Princeton, Duke, right? Like all the top schools.
Harris Stolzenberg (30:43.213)
Yeah, CMU, Waterloo, it’s funny. in the fall, I called it like the PairX World Tour, basically telling everyone about this accelerator. Obviously, I spend time at MIT and Harvard, but we do the rest of the IVs. CMU is big with robotics and AI. Waterloo has got a great engineering program, Duke as well. yeah, 12 schools in like three weeks, basically campus to campus, doing office hours during the day and spreading the good word of Pear at night for info sessions.
So it’s been a lot of fun, a lot of travel. I definitely live out of a suitcase a bunch and I do a fair amount of travel to SF as well. But I love it. Look, my job is just to talk to smart, ambitious people all day long and yeah, I don’t get tired of it, so it’s fun.
Keith Cline (31:30.271)
Yeah, so how do you decide? mean, because students, it’s not like they have a proven track record. I already started a company or I failed at this company, but now I’m ready to do my next thing. It’s like they’re cutting their teeth. But they also have that blind ambition of greatness, right? So how do you figure out which students to spend time to? Yeah.
Harris Stolzenberg (31:41.102)
Yeah.
Harris Stolzenberg (31:47.482)
Yeah.
Who do we invest in? Yeah, that’s the million dollar question. That’s the question that we get asked that, you know, every panel we’re on. And I wish there was like a great scientific answer. You know, the truth is there’s not, think every VC has a little bit of a different taste. But one thing I will say is, you know, when you meet a hundred founders or now, you know, I’m at like thousand founders, just by meeting that many people, it becomes apparent. Like if you’re like a top 1 % founder, just, it just feels different. And I know that’s not,
a great kind of answer, it’s the truth. I think, look, you’re looking for certain qualities, but every great founder, I think, is an outlier in some way and exception to some rule. But yes, certain things that I look for are moving incredibly quickly, right? Like, you know, it’s a bad sign if you’ve been working on a startup for a couple months and you haven’t shipped a product, you’ve only talked to a couple potential customers. Like, I love the founders, or it’s like, last week I got off
100 customer calls back to back and here’s what I learned and here’s the three features I shipped and then I talked to those customers again and then I iterated and I shipped again. Now we’ve got our first paying user. Like that just feels different than like, hey, I’ve been in development for the last six months and we’re gonna ship eventually. And then another thing is like, I like to think of like, this person is gonna need to hire, they’re gonna need to fundraise and they’re gonna need to sell. So I try to think to myself, like, would I go work for this person? Would I feel comfortable putting them in front of, know, marketing?
Andreessen to pitch for money. You know, would I feel comfortable putting them in front of a customer and being confident that they could close them. So there’s just some things you’re looking for, but it’s very much an imperfect science.
Keith Cline (33:33.279)
Now is your goal to ultimately get the best companies to apply for this cohort and be one of those 25 per program, twice a year type of companies? Or are you actually looking to write checks in these companies?
Harris Stolzenberg (33:45.551)
Yeah, yeah, so through that program we write checks. So that program, Parax, we’re writing checks anywhere from 500K to $2 million. So that’s definitely like our bread and butter. YC only goes to 500K. So for us, for this program, because we take less companies, we can invest more. So we can invest up to to 2 million. But some founders don’t want like an accelerator. And I think you’re seeing that more and more these days. look, we don’t make people, if people don’t want it, like you don’t have to go. We could just give you a normal $2 million.
and investment and kind of help you outside of the context of the accelerator. We’re also a seed fund as well. So like I mentioned earlier, we write checks up to six million. So we’ve written a couple of checks kind of between two and six. And it’s definitely less common for us, but every now and again, you meet someone great and we write those bigger checks as well.
Keith Cline (34:37.995)
Do a lot of the VC firms have like, cause like I remember those, the dorm room fund, there was rough draft ventures from general catalysts. are there like a lot of the VCs still have this presence on campus with students kind of being like an investor, fellow, whatever their title is at this.
Harris Stolzenberg (34:55.727)
Yeah, I don’t see a rough draft very much. Dorm room fonds little bit, but I think once they separated from first round, they’ve kind of become less visible. I’d say that the folks I run into the most, it’s just like why everyone, like most university founders have heard of YC. So like that’s the, that’s the brand I’m seeing a bunch. There’s this thing called Z Fellows, which, comes up now and again. Neo. I don’t know if you’ve heard of Neo, but I’d say, and then South Park Commons.
a little bit as well, but that’s less for college and more for a little bit older founder. So those are the ones I’d say I bump into the most now on campus.
Keith Cline (35:38.015)
And it’s also not just undergrads, it’s MBA, PhDs, even professors too, right?
Harris Stolzenberg (35:44.771)
Yep. Yep. Yeah, we invested in a CMU professor last batch. PhDs as well. We really are trying to back more PhDs to spend a lot of time at HBS. My colleagues spend a lot of time at Sanford GSB, their business school. So yeah, we don’t discriminate. If you’re a great founder, doesn’t matter what program you’re in. We want to talk to you.
Keith Cline (36:10.827)
Yeah, okay. Yeah, because I just, when I think about the schools you’re targeting, obviously you’re focused on density of talent, right? These are people are very bright, very probably driven. They just have all the nuances. But then what about the other schools, right? That the Northeastern’s, the Worcester Polytech, know, like the BU, right? Like there’s great, great Tufts, right? The Nescahx, right? Like, so like, do you ever think about those or is it like, know what?
talent density, we only have so much time and we are, you know.
Harris Stolzenberg (36:41.976)
Yeah.
Look, I think there’s plenty of examples of great founders that didn’t go to one of the schools I cover. Like Brian Chesky, I think I mentioned him earlier. He went to Rhode Island School of Design. Yeah, RISD, like all the schools you mentioned, all great schools. If it was up to me, like I wish I could spend, you know, time at all of them. I think the thing I’ve learned very quickly in this job is like, you’ve only got certain number of time blocks every day and you got to pick and choose where you’re going to focus. you know, a lot of VCs or folks come up to me and we’ll
Keith Cline (36:51.337)
Yeah, RISD.
Harris Stolzenberg (37:13.785)
kind of say like, well, look, you’re going to miss out on someone great at one of these other schools. And I think that’s just a choice we made as a firm. Like, you hopefully those people hear about us and hear about our brands and apply and we kind of get to see them, you know, through that way. But yeah, it’s imperfect. And I wish we could spend more time at some of those other schools because there’s a lot of great talent there as well. But just given kind of the amount of time I have and the amount of time people at our fund had have, we kind of pick a couple.
schools to focus on.
Keith Cline (37:45.909)
What’s a good example or two of companies that you’ve been involved in so far?
Harris Stolzenberg (37:50.765)
Yeah, there’s two, I don’t know, that come to mind that are doing really well. One is this company called Build AI. It was a Columbia dropout. They are making, they’re doing egocentric data collection for robotics. So what that means is they’re putting glasses on basically factory workers and watching them do their job. And then the plan is eventually either to sell that data to humanoid robotic companies or use the data themselves to train on it and build models.
or even hardware in the future. they just raised quite a big round recently. So they’re doing really, really well. And it’s crazy, like the founder, Eddie, he’s, I want to say 19 now. So, and he’s raised tens of millions of dollars and they’re moving very quickly, like executing at a pace I’ve never seen. So that’s one. So like humanoid robotic data collection. And then another was just like this vertical software company where they help right now pavers. So if you’re a paver, you want to get like more jobs.
you want to bring in more business, you have to submit bids to do rework or submit a bid to pave something. To do that, you basically, you have to hire someone to estimate how much input cost and time it’s going to take to do a certain, let’s say, property size. And right now, it’s all done by hand. So we met these two computer vids.
Keith Cline (39:00.479)
Bye.
Harris Stolzenberg (39:20.749)
PhDs and then someone that comes from like the paving and roofing world and they created a way where you can just take an image and do it in three seconds and like you you watch them you watch them do these demos and these people can’t believe it they’re like this isn’t real like this is magic and they’re taking off and doing really really well so it’s it’s it’s cool to see and yeah there’s a bunch of other companies that we’ve invested in as well but those are two that come to mind
Keith Cline (39:30.57)
Wow.
Keith Cline (39:48.065)
Yeah, great use case for machine learning and computer vision. So you’ve been in the startup VC ecosystem for long enough where you saw a pre-AI platform shift era to now. And as you were talking, the pace of growing companies is so… So what have you noticed, just kind of like your lens of like one check sizes used to be like so small, now it’s like a seat is like a hundred million dollars.
Harris Stolzenberg (40:16.611)
Yeah. Yeah.
Keith Cline (40:17.1)
Look, obviously, it does happen, but very few. But anyways, I’m just being exaggerating a little bit. But the round of funding and the pace of building companies, it just seems like everyone’s seeing this as this is the window. We got to build this now before we miss out.
Harris Stolzenberg (40:33.327)
Who knows? Yeah, I guess no one knows the future, but it is crazy to see. think like back in the day, you know, these rounds were smaller, but also the funny part is they were smaller.
And like the money couldn’t go as far. Like you needed to pay, you know, for a bunch of things to get a company off the ground. The funny part now is like you can start a company with no money and like, you know, you don’t, it’s like the tools available to you are crazy yet we’re seeing these rounds that are, that are massive. And look, I think there’s going to be a ton of winners in AI, but also a ton of losers. Like the even Maher, my boss was saying this, like the amount of founders she’s seen has like quadruple
over the last 10 years, but the number of category-defining companies that are started every year stays the same. So your job as a VC just became four times harder. There’s also way more competition in venture. look, I do think there’s definitely a little bit of luck involved too. You gotta make sure you’re in one of those or a couple of those 20 companies every year. And the hard part is you never know which one those are until afterwards.
Keith Cline (41:44.813)
I’m going to sound like the old Comunjian now, because I kind of am getting old. So I started in the tech industry in 98, and that was when the dot com boom happened, right? And you’ve seen different cycles, the mobile to cloud to now AI. And you’re like, OK, this is the new cycle. The one with this one, though, because the mobile and the cloud, was platform shifts. This one, watching the Super Bowl last night, I’m like, oh, we’re back at that moment.
where it was all dot com commercials for the Super Bowl. I’m like, they’re all having their, like everything was something AI or cloud or cloud or open AI, Microsoft, like everybody was pushing and even some startups. I’m like, how are they having a startup Super Bowl commercial already?
Harris Stolzenberg (42:30.489)
We’ll see what happens. Look, there was a dot com crash, it came back eventually. Like there was real substance to it and maybe that’s what happens with AI and maybe, maybe AI keeps going this way. think we’re going to find out and who knows? I don’t think anyone.
Keith Cline (42:35.498)
Yeah, amazing substance. Yep.
Keith Cline (42:45.696)
No, no. But we’re definitely in the early innings. still, and I’m hopeful that this is going to be a long runway where there’s, the use cases is very different than just setting up a website and going public as whatever.com. So it’s very different. Now, how do you use AI for your job?
Harris Stolzenberg (43:05.635)
Yeah, the real answer is I should be using it more and we have…
three engineers on our team and we’re definitely in the process of putting together different things that we’re doing. The easy one is we use granola. So every one of my conversations is we take notes automatically and the nice thing is you can search across those notes, which as a VC is huge. We use a CRM system called Atio, which ingests all your granola, ingests all your emails across the
organization and they just released like a big feature called Ask Atia recently where now you can query a natural language, know, different things across the organization. I’ve been playing with it, you know, like every AI tool, like there’s a hundred things they need to fix, but like there’s definitely some potential there. And then, now when we get pitches, like we kind of can score them, you know, using AI and…
The scoring has a long way to go too. So like everything in AI, like we’re starting to use it and play with it, but I think there’s a long way for different tools to come before we’re automating some of the workflows that I would like to see automated.
Keith Cline (44:21.247)
Now you’ve been in the Bay Area, you’ve been in different ecosystems to know kind of like you’re in New York and to these different schools throughout up and down the East Coast or wherever. So what’s your thoughts on the Boston ecosystem, just broadly speaking?
Harris Stolzenberg (44:37.709)
Yeah, I think, look.
The talent here, you you mentioned all those schools like the Nez Cacks and all of those, and those are great, and like those bring in talent, but like MIT and Harvard are some of the best institutions in the world, and they’re not going anywhere. So like you’re always gonna have this influx of amazing, amazing talent. I think the pro, I don’t know if it’s a problem or not, but what we see is people come here and then they go take jobs in SF or New York and they leave, and I think there’s, you know, this new push to keep some people around.
and as someone who loves Boston and wants to see the city flourish, I would absolutely love to see that. But look, let’s call a spade a spade. In terms of tech, it’s not close to what SF or New York is. And I do think a lot of changes need to be made if the goal is to have some of those companies being built here. Look, the cool thing is we have that unique access to those institutions that the only other place in the world that really has that is San Francisco with Sanford.
in Berkeley. So like the ingredients are here. We just need to figure out how to keep the talent.
Keith Cline (45:47.946)
Yeah, agreed. And I do love how there’s a new rallying cry of let’s go again. Because I think Boston did get a little sleepy. And I don’t know if it was just because of post-pandemic where people weren’t gathering and doing the events. Because I definitely saw that as a missing void. And with Venture Fizz, we started hosting our own events again to try to foster that. And with the Mass AI Coalition, there’s definitely some good things that. Like the last time this rallying cry happened, it
I mean, think that was kind of the early days of companies like Toast. So, it does create some waves that hopefully make an impact. But I mean, I never position Boston against San Francisco because it’s just not fair. It’s like so not even remotely close. What I like to position Boston is, so I live outside of Philadelphia. The Philadelphia ecosystem is starving. There’s no capital here.
First round capital here is just because Josh Copeland had half.com here and lives here, but they’re not writing checks in lots of Pennsylvania companies. And you’ve got Penn, Wharton, Drexel, Temple, Villanova, Lehigh, Penn State’s a few hours away, Princeton’s not far away. There’s no ecosystem. So Boston thrives, if you compare it to that type of city.
Harris Stolzenberg (47:05.231)
Totally. Yeah, look, think, no, that makes sense. And look, I think Boston is a unique ecosystem and there is a lot going for it, but there’s just something different about SF. Like if you’re in a coffee shop and you’re talking to someone and they like you and they think you’re smart, it turns out, you know, they were employee number four at Uber or whatever it is, and they write you a hundred thousand dollar angel check in 10 minutes. Like that just doesn’t happen in Boston.
Keith Cline (47:29.329)
Alright? True.
Harris Stolzenberg (47:32.875)
It would be nice to, I think Boston VCs get a reputation of slow and low valuations and sometimes in SF now you can meet with the founder for 30 minutes and you have to make a multi-million dollar investment decision and whether that’s good or bad, there’s arguments to both but it’s just a totally different ecosystem when it comes to funding and I think a lot of founders are getting advice like, hey, if you’re trying to raise money like,
and your base in Boston, go fly out to SF and raise there and then come back. And it’s probably the right advice. Like, you the nice thing about Pear is we’re here and we’re there. So it doesn’t bother me if you do that. But selfishly as someone who loves Boston, like if we do want to see the talent stay, I think that mindset has to shift a little bit.
Keith Cline (48:20.758)
Well, that’s why I was excited to see someone from Pear is in Boston. This is good for Boston. So, all right, three apps you can’t live without, can’t be Slack, email or your calendar.
Harris Stolzenberg (48:30.487)
Ooh, three apps I can’t live without. Okay. I’ve been playing a lot of chess, chess.com like at night. I’ll go chess.com. can I, can I say Twitter? I won’t call it X. I just call it Twitter. I love Twitter. get all my news and either sports or tech on Twitter. And then, I feel like I call a lot of Ubers Boston. Everyone says we have good public transportation, but I don’t, I don’t buy it. It’s, it’s, it’s, I don’t love the public transportation here. So I take a lot of Ubers. Yeah.
Keith Cline (48:40.8)
Yeah. Right.
Keith Cline (48:57.74)
Alright, podcast or book recommendation for entrepreneurs.
Harris Stolzenberg (49:01.997)
I haven’t listened in a while, but when I was doing investment banking, I’m at to and from work every day. I would listen to the 20 VC podcast by Harry Stebbings, his own fund. And I’d like to say I’m an OG listener because I listened like way, way back in the day when he was getting started. So that’s, that’s my podcast recommendation. Although I haven’t listened in a long time. And then book. I like shoe dog.
Keith Cline (49:11.011)
yeah, Harry Stabbings, amazing.
Harris Stolzenberg (49:28.223)
story of Nike and then also on the topic of shoes delivering happiness about Zappos was a good one as well. good books.
Keith Cline (49:34.988)
Yeah. Zappos’ primary competition back in the internet 1.0 era was ShoeBuy.com. So I just had the founder of ShoeBuy, Scott Savitz, who’s data point capital. Yeah.
Harris Stolzenberg (49:46.893)
No way. I my Metz guy. I did not know he was the founder of that company. Okay.
Keith Cline (49:51.853)
That’s why I would see them at events. I’m like, we need to tell the story of ShoeBuy. And actually, if you listen to the episode, it was very transformative as far as how they thought about the business model, because no inventory, the distribution, their customer acquisition, very different than Zappos, but they were both rooting for each other because they were trying to pull together an industry, a mindset of consumers, good customer service. So it was really interesting episode that you should check out. What do you like to do for fun outside of work?
Harris Stolzenberg (50:18.553)
Nice.
Harris Stolzenberg (50:22.423)
I’m a big foodie, so I’ve got my list of Boston restaurants and I’m trying to check them all off the list. So definitely restaurants, go to the gym a bunch and big Miami Dolphins fans. So I think we were talking earlier about the Super Bowl and all my friends and fans and I couldn’t have been happier to watch them suffer, but it’s okay because they’ve won quite enough in their lifetime and they can always tell me that I’ve never watched the Dolphins even win a playoff game as long as I’ve been alive. So it’ll be okay.
Keith Cline (50:36.544)
Yeah.
Keith Cline (50:40.14)
You
Keith Cline (50:51.062)
Ooh, I didn’t think of it that way. Ouch, that’s… Yeah, like I entered. It makes me stronger. like I was, you know, I expected a different game, but I didn’t know if we would beat the Seahawks just because their defense is so good. But yeah, I went into the game with no stress because I’m like, you know what?
Harris Stolzenberg (50:53.965)
Yeah. Tough. Makes me stronger though. Yeah.
Keith Cline (51:14.54)
This is how it’s money. I can’t believe we’re actually in this game because entering into the season being 3-14 the year before, was like, to be in the Super Bowl, this is amazing. So anyways, I’m very long on Drake May and Mike Vable. They’ll be good. So, there you go. Cool. Well, Harris, thanks so much for taking the time to walk us through your background story, obviously all the great work you’re doing with you and your colleagues at Pear, and obviously all the great advice.
Harris Stolzenberg (51:26.575)
He’ll be good. Well, they’ll ruin my life for many years to come.
Harris Stolzenberg (51:40.151)
Awesome, appreciate it. And yeah, if there’s any founders listening, definitely shoot me a note. I’m Harris at Pear.VC and yeah, just love meeting folks at the earliest stages and thanks so much for having me on, Keith. Appreciate it.
Keith Cline (51:54.103)
Cool. All
