Episode 423 of The VentureFizz Podcast features Sasha Hoffman, Partner at Remus Capital.
I first met Sasha over ten years ago, when she was the Chief Operating Officer at Piaggio Fast Forward. VentureFizz helped cover the launch of Gita, the cargo carrying robot named Gita,
Thus, this interview was long overdue and I was excited to interview Sasha as her career has been so prolific.
We cover a lot of ground including:
Sasha’s playbook for creating high impact, curated events from getting sponsors, programming, planning activities, and getting people to show up!
Sasha’s background story as a competitive dancer and getting her career started in investment banking during the birth of social media and SaaS, then transitioning into various operating roles at startups and at scale at Uber, where she ran their loyalty program, so she had lots of advice to share on that topic.
Transitioning into venture capital and all the details on Remus Capital and what she is targeting for investments and what “Say, Seed, Do” means.
Lots of advice on Angel Investing.
And a deep dive on traveling and her hacks on finding the best deals.
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Transcript
Keith Cline (02:00)
Sasha, thanks so much for joining us.
Sasha Hoffman (02:02)
Thanks for having me.
Keith Cline (02:04)
I’m excited to talk to you. This is long overdue. was somehow saw maybe a post of yours on LinkedIn. I’m like, how is Sasha not been on my podcast yet? I’m 400 episodes in. This is far too long to be doing this. ⁓ But thank you so much for taking the time. I appreciate it. And I was trying to remember where do we first meet? was like, I was like, was it Plastiq or was it Piaggio? It might’ve been Piaggio. I just couldn’t connect the dots on the two, but we go way back now.
Sasha Hoffman (02:31)
One of the peas and at least 10 years ago. So a while is the point. ⁓
Keith Cline (02:36)
Exactly. So, all right, to kick things off before we talk about your background story, ⁓ VentureFizz you know, we’re deep into the Boston tech ecosystem.
We build community, we run events, which I learned that’s something that is part of your identity too, that you actually started a events and luxury travel business after college and you still run these events that I see you post about on LinkedIn. So, so talk more about what goes into planning a well curated, productive event, especially for someone, know, so for founders and investors that are doing this like weekend or however many day retreat type of format.
Sasha Hoffman (03:16)
Yeah, absolutely. just by way of background, in college, I had started planning trips for group organizations at school because I realized there’s power in numbers. So we could get way better deals whether we doing retreats to Mexico or it didn’t matter what it is. And I was like, oh, this is really interesting. And I happened to be very good at logistics and bringing community together. So I started it that way. And then even after college, I was doing a lot of more luxury trips for friends. So it’d be, oh, let’s do a safari. We’ll bring 20 people. Let’s rent a villa in the Caribbean.
Keith Cline (03:45)
What?
Sasha Hoffman (03:46)
20 interesting people.
Keith Cline (03:47)
Why didn’t I meet you after college? It sounds amazing.
Sasha Hoffman (03:51)
And so that’s like kind of how it started. It actually really started in the travel space was how do you get more bang for your buck? Go to interesting and possibly more expensive places and just bring a bigger group of interesting people to go with you and get better deals. And then I realized, know what, the margin on that isn’t great, but I loved it because it was a way to just see friends who I didn’t charge more for, or I would only run a few of these types of trips, but you just don’t make as much. It’s like, this doesn’t make as much sense. Longterm at the time I was working a full-time job, still am. And so I switched over to the corporate side.
I said, okay, instead of doing so many of these, why don’t I just do like three or four events per year where I get to choose who I work with and we’ll curate and create ⁓ unique experiences. So whether that’s a two-day retreat for portfolio founders of a VC or it’s, you know, an LPGP summit or…
founder partner retreat for investors and founders to meet and so it just started to grow and Organically because my own network as I was working in tech and finance crossed over those areas I started just working a lot with venture funds high-net-worth individuals ⁓ Bank service providers to sort of make those things happen so that’s kind of context on what we actually do and how it got there and I just sort of pick who I enjoy working with that can act as a flywheel for me and I think we’ve all been to a hundred, you
plus conferences, right? And so for me, it’s always been when I work with various folks, how do you just create an environment where one, people want to open up and have an opportunity to properly network? I’ve always struggled with those big, you 3000 person conferences because it’s just tough to meet all the right people. If you go in, you’ve already set up your meetings and it’s just a convenient location. That’s wonderful. But if you’re going with just the intentionality of how do we just meet interesting curated people? It’s very tough to do that in that environment. And so I often focused on the things that were less than 200 people or even less than a hundred people where you do high curation on the front end to make sure these types of people are looking to want to meet each other. They have the capacity to do business together. And then two, how do you create environments for them to actually do that? So I think about it a lot as summer camp for adults. If you create experiences where they can bond over, that’s a great way to remember people, right? So we do this annual Finger Lake Summit that I do with Impellent Ventures and Fidelity.
Maybe in a bunch of others and you know every day we have unique experiences so sometimes there are theme parties and everybody gets dressed up and it gives you something to talk about. We do trivia where you work in groups we’ve done you know ⁓ wine tasting, hiking, biking so just you begin to really develop a friendship with somebody when you meet in that type of environment. so between curation and just creating good opportunities to meet and bond with people while you’re at something, I think that goes a long way as well as just making it smaller.
Keith Cline (06:42)
So one of the things, so anytime I see these posts from you or David Brown from the Finger Lakes Retreat, I have FOMO. Cause I’m like, man, I wish I was there. It looks like lot of fun. But I see the curation of founders, right? So you have a hundred, don’t know, 120, 130, 140 founders.
How do you actually get that on their schedule to commit to something like that? Like how far in advance are you like planning this so that they know that this is part of my… July or whenever you host it.
Sasha Hoffman (07:13)
So usually five to six months notice, some people will give even more. I mean, we begin the planning almost 10 months in advance, usually have locked in a date actually. And then we have a venue locked in, because a lot of these venues, if you buy out hotels, and this isn’t true just for Finger Lakes, but for a lot of what I do, when you’re buying out a full property of 100 plus rooms, usually they’re selling out a year in advance because you’re often competing with wedding venues as well. And so we use a lot of those types of same spaces, or I have historically. ⁓ And then we’re getting on those founder calendars, you know, four or five months in advance. In our case specifically, that summit, although not all of them, you know, has an opportunity to be all expenses paid because we want to really incentivize the right people to come and we want to be able to choose who we select and say no to people as well but even ones where it’s paid you still want to be able to tell people you know most of these big conferences give people four to six months notice at minimum.
Keith Cline (08:09)
And then the actual curation of the payment to afford this, right? So that the founders are not paying. ⁓ That’s a lot of work too, right? Like, cause we, run the half day summits and I have sponsors and that’s a lot of work to get companies to participate and sign up to do that and obviously contribute financially. So how do you take care of that piece too?
Sasha Hoffman (08:30)
Yeah, I mean, I think this is true for everyone running events that need sponsors. You want sponsors who can get value from the types of people you’re inviting. So at the very beginning of all of this summit planning, we’ve been so lucky that we pretty much had the same sponsors at this whole time and we’ve added more as well because they got value from it. But we start by asking, what is it that you actually need? How do we drive value? We said no to sponsors as well, where we just knew they weren’t going to extract any value. So there’s no chance that they come back. And the amount of effort that it takes to get a sponsor is high. And so they don’t get a positive experience at real measurable ROI, they’re not going to come back and you kind of wasted all your effort. And so I think we’ve made a pointed effort both on this as well as I have for other summits where we need sponsors to ask in advance what does good look like, what does success look like, and then actually ensuring that we can deliver that. And in fairness, a lot of our sponsors do the invites as well. We work together to make sure we’re all inviting interesting people. You know, they obviously have huge and great networks. And so it’s everyone coming together actually to build the invite list.
Keith Cline (09:30)
And then how do you think about the programming? Because that’s a heavy lift to have a multi-day summit.
Sasha Hoffman (09:35)
Yeah, you know, I think some of these summits, obviously they’ve already got a full set of themes in advance of even having the guest list. As it happens with Finger Lakes, we’ve historically, we’ve made the content around the guests. So we actually ask people when they’re registering and then, you know, within call it 60 days of the event, what are the most pressing issues for your business right now? What is actually keeping you up at night? You know, what is it that you want to talk about? And our programming is structured as a bunch of keynotes, it’s actually structured as facilitated group discussions.
So if people want to talk extensively about fundraising, going to have a, we had like a three hour workshop one day on fundraising. so, or it’s how do you build your brand on LinkedIn? Whatever the things people may want to talk about B2B sales partnerships will create these in-depth dialogue. So it’s almost like a group, smaller group discussion talking about that. And we break off into different rooms. I do find that the only way to build programming around your guests is if you know the full guest list. I think it is extremely impactful if you can do that and you know what
what people actually want to talk about. And then you give them the opportunity in the setting to do that. And the right person is facilitating or giving their advice on what’s happened. It’s hard to otherwise do that. But I do think it’s valuable, frankly, for any summit, whatever the topic may be, whether you’re talking about cybersecurity, it doesn’t really matter, asking people what they’re interested in and collating that and then using that to build programming. How often have we all just gone to stuff and we just leave the room for the programming because it’s so boring. We’re like, we’d rather just talk to somebody in the hallway. I mean this happens all the time, right? so.
Keith Cline (11:06)
All the time.
Sasha Hoffman (11:09)
And then we always have, so for us,
Keith Cline (11:10)
Yeah.
Sasha Hoffman (11:10)
Most of it is closed door and no posting about it. And so we’ve had people also just talk very honestly and candidly about here’s where we’ve screwed up. Here’s really bad things that have happened in our business. Here’s how we grow. And I often find the stuff that you can’t Google is truly the best conversations. And so getting folks to come and be willing to, you know, give real case studies of how they grew their business, what they’ve done. ⁓ you know, we’ve had viral social media stars come and talk about how they build all these videos, how they grow virality and that sort of science-based approach really helps people in the audience take back a nugget and actually do something with it. Not just, I heard an interesting story, here’s a playbook, here’s case studies, here’s things I can then go replicate for my business. That sort of active learning I think is very different. It makes people leave a summit and feel like, I actually got something out of this.
Keith Cline (12:00)
What about after the event? So you brought, you know, hundred plus founders and great speakers and VCs together. What do you hope, you cause you’re trying to build community, right? So what do you do post-event to make those connections still stay engaged?
Sasha Hoffman (12:16)
So we leave most of that to the people. I will say there’s plenty of organizations that do this because people pay into an organization. So whether it’s YPO, which I think is really wonderful, or some of the others, they have consistency in that programming. As it happens, this event is only once a year. Um and we leave it to all of these individuals. Like we provide guest list information and we leave it to them to do business. As it happens, we do go back to check what people have done. And most years, almost 80 % of people report they’ve done some sort of business with people there.
As though it’s self-selecting in a way of like, I met somebody that’s interesting, I’m now gonna go do that. So whether you raised funds, you invested in a company, you became a board member, they introduced you to corporates, there’s something that got done that the conversation began at the event and then it naturally ended up going somewhere afterwards. And so I think we’ve been lucky in that a lot of people naturally did that. There’s been some small meetups and I think what’s actually amazing is I often get texts from people with a not a screenshot, a selfie, and they’re like, hey, I’m with this person that I met at your event.
And this happens to all the time,
Keith Cline (13:16)
That’s so awesome.
Sasha Hoffman (13:17)
Like at least once a week, I get a selfie of somebody, I met this person three years ago because of you, here we are, which is great, right? I mean, that’s what you want. It’s this permanent sense of I built a friendship, I built a work relationship, that is community by definition.
Keith Cline (13:32)
Yeah, it is so satisfying. I love doing that too. And I agree like with the audience curation, that’s something that I do with VentureFizz too. I think it’s so important to have the right people in the room together. And then I don’t record my in-person events because I want people to speak freely and not worry about, is this going to be posted out there? So, all right, well, thanks for all the great tips.
But one more question before I talk about your background. Like not every event is perfect. So what’s your big, hey, if you’re planning an event, this is something you need to do to make sure you avoid any catastrophes.
Sasha Hoffman (14:06)
I guess a couple of things you can expect that year one of anything is never its best year. If year one is your best year, something is wrong. So, you know, it’s a learning experience. I always say when you try something for the first time, just make it smaller because it is more contained. You can do better in a way if you just start everything smaller. I know it’s hard to do that. Sometimes you want to go big or go home. But the truth is, it’s just more in control if you can just start with a smaller and better experience. So that’s kind of one thing. ⁓ Two, you know, I tend to find the more communicative you are with guests in an easy format, the better it is. So if you have a website that has like 40 FAQ questions and is easy to find things and very descriptive, nobody wants to be left guessing, right? So like, what is it that I need when I come? What am I actually gonna be doing? Is there time for me to go take work calls? It seems trivial, but the truth is, if you’re a busy business person, you gotta leave somewhere, even for a full 24 hours for something, it’s just helpful to have kind of all that information. The other thing is like, don’t over-program.
A lot of the events that I’ve done, they’re programmed. Like you’re here at this dinner from six to eight, six to nine, but outside of, know, cocktail hour, it’s somewhat more open for you to just meet people. Or we had a casino night. So it’s like, I’m not telling you what games to go to. You’ve got two hours to play on a casino and meet people at all the games tables. I think sometimes people just over-program each minute. And actually the best things come from honestly just meeting people in between and being able to have a moment to have a conversation. I also think the mistake that a lot gets made, we corrected this kind of year two, as we didn’t do it as much year one, was it’s best to know who everybody is when you get there. So I don’t want to call it speed dating, but it kind of is. You want to know some tidbit about everyone. And historically we made little profiles, we let people see it in advance. But if you can even organize little groups and people can rotate, know, there’s other conferences that do this too. How amazing is it if you can get through a hundred people in an hour and a half and know one little tidbit about everybody to remember what they need. It makes a really big difference for how you spot people over the rest of the conference. And maybe you can’t get through 100, but if you can even get through 30, even if there’s four people in that, they’re like, okay, I need to meet those people. That just gives you somewhere to go. And I do think people mess that up a lot and they just leave it to the audience to just go find people or expect that they did all this research in advance, which thanks to AI now is a little bit easier, but it just takes time. And I don’t want to make the assumption that everyone’s done it because nine times out of 10, they haven’t. They’re probably my best ones.
Keith Cline (16:34)
That’s great tips.
Yeah, that’s great feedback and definitely some things hitting home with me. ⁓ I’m gonna switch gears because I could talk to you about events all day. ⁓ the one pet peeve that I’m just gonna tell people, if you’re planning an event, not a retreat, this is different. That’s a multiple day thing. ⁓ But if you’re doing an event, like a half day event or even like a couple hour event at night, have name tags, even if you don’t have time to print out name tags for everybody, but have name tags with a little Sharpie pen, the worst thing that I experienced going to an event and if there’s no name tags is you see someone you know and you’re like, ⁓ what’s that person’s name? It’s gonna bother me. And then you have that awkward moment and you’re like, I should know this person’s name. And then the person that you don’t know, it would be helpful to know what company they work for. Be like, do you know so-and-so? Or right away you’ve got an instant connection to talk about something. you work so, I just saw they raised capital.
Have name tags. All right, that’s my rant. Let’s talk about, okay, let’s talk about your background. So where’d you grow up? What were you like as a child?
Sasha Hoffman (17:29)
Yeah, I agree.
Well, I think there’s what I would say and then there’s what my mother would say. So let me maybe quote her instead. I grew up half in New York, half in California. And California was in Marin and outside of San Francisco, if you cross the Golden Gate Bridge. And then in New York between the city and Staten Island. And so as a child, I think I was quite mischievous. I would watch things on television and then I would immediately go do them. So I watched Tom and Jerry and then I saw that they like lit the cat’s tail on fire. So I attempted to go light my cat’s tail on fire.
Keith Cline (18:07)
No way. That’s phenomenal.
Sasha Hoffman (18:07)
I was not going.
I just was like, anything I’d see, would just say, like, I should try that. I had no fear of anything. And then ⁓ I also was a mini entrepreneur. my parents worked a lot and they were gone a lot during the day. And so my grandmother was often home and she really had no clue what I was doing. I used to get back in the day, they would ship you gift wrapping samples. So it was like before you would, you would have to actually, I feel like I’m dating myself so much, but you would have to order the gift wrapping paper that you wanted. So they would send little, little snippets of like what they looked like. So, I would take those and then I would go sell the small samples to kids on the street for 25 cents. And then I would make a ton of money and go, use this little gift wrapping paper. And then I would bring home all the money and then the parents would come and complain to my mom that I hustled their kid. And I would like, don’t want to
Keith Cline (18:46)
Nice!
Sasha Hoffman (18:56)
Like, you can’t do this. And on the other hand, my dad’s like, but it’s also very entrepreneurial. So I can’t say that you shouldn’t do this. So I was a bit of a fighting entrepreneur. was also, I was a competitive dancer. And so I, yes, I did. all growing up, I did hip hop, Indian dance, belly dancing, all kinds of things. I was constantly touring, competing, performing. And so I was gone a lot, but.
Keith Cline (19:05)
Absolutely.
You are?
Sasha Hoffman (19:22)
I didn’t have a ton of sports. had dance, but it got me. It got me a lot of discipline, which I think is good. And it’s a great sport to keep people happy.
Keith Cline (19:32)
Did that carry over to UCLA too?
Sasha Hoffman (19:35)
Yeah, I’ve danced my whole life. That’s always been my activity. I choreograph for our school’s dance teams at UCLA. My dream actually when I was in high school and even in college was to go be a Bollywood movie star. My parents were like, no, you’re going to do math. So I ended up doing math. It turns out if you come from parents that are Indian and Jewish, they’re really into math. And so they were like, this is a better and a safer path. I couldn’t become a doctor because I can’t handle the sight of blood. I thought about becoming an engineer. So they were like, these are the good paths.
Sasha Hoffman (20:05)
So it disappeared, but I still do a lot of dance to this day.
Keith Cline (20:10)
Well, you did go to UCLA, which I’m just gonna side note. That’s my dream school. So I have a cousin who lives in LA and I visited her years and years ago when I was a little kid and I saw the campus and I’m like, I need to go to school here. And then I realized it was hard to get into. So I didn’t have a chance.
Sasha Hoffman (20:29)
What’s funny is like it’s so popular in Asian countries that sometimes I go to them and I see people with UCLA branding. They’re like wearing our sweatshirt just because it’s cool and I’m like this is very interesting. I feel like a marketed brand. Yeah it was fun. I stayed too short. I finished college really early. I finished in like two and a half years and so I worked soon. It turns out I should have stayed for five. Someone should have told me that but they gave me credit for a lot of my APs and I was just good at school so there I went but I did love it.
Keith Cline (20:40)
Yeah.
wow.
All right, what did you do after college?
Sasha Hoffman (20:59)
I went into, I did math. So I went into finding out. So I went to Lehman Brothers, which we all know what happened there. And I joked with my parents, look, I just want to a firm that went bankrupt, if I was going to not have a job, I could have been a Bollywood actress where I also might’ve been out of a job. So it could have been that. But no, so after Lehman, the bank got bought by Barclays. I got lucky, actually never got laid off. And then I went over to Goldman as, as when we kind of after, after the acquisition and I covered tech companies. So I did.
Keith Cline (21:02)
Hahaha
Sasha Hoffman (21:29)
investment banking at both firms and I was in our technology groups and I covered social media, software and semiconductors and it was just very interesting time. It was honestly back in 2008 plus it was the birth of SaaS, it was the birth of social media so I got lucky. I was at the beginning of truly frontier tech of that generation and I got to see the whole wave and grow with it and to be part of that gets you excited to be at the beginning of a lot of these huge trends right at the start and you also just learn to see things and what’s their potential is. I ended up doing at the time was called Facebook, but Facebook’s IPO Yelp, like a lot of big names that we now know today, but back then seemed smaller. So it’s very cool to work on them.
Keith Cline (22:10)
How’d you make the transition to more, you know, startups and tech companies?
Sasha Hoffman (22:14)
Yeah, so was a banker for five years and then sort of, you know, I hit a point, actually, I kind of need to like thank some of the female bankers that were there because at the time, you know, was closer to my VP promotion and I realized, you know, if I stayed there, I probably wouldn’t leave. It was just, you know, the golden handcuffs are real. And to be honest, they had great jobs. They worked with such interesting companies, but they did work hard. And I just remember at some point someone being like, you know, as a female, it’s definitely harder to do this job. Like just imagine yourself in six years, a managing director, you will work a ton. And it’s a choice, but just as a heads up, she’s talking about her own relationship and she’s like, I don’t see my husband that much. It’s something you just might want to think about. And so at the time I was like, okay, I also think I enjoy really building products. I’ve been talking to all these CEOs and their teams about how do they actually go to market and how are they thinking about adding on new features and…quite a few were like, might have a future actually on the other side of this. And so I figured I was still young at the time, I was in my mid 20s. I was like, I have nothing to lose by going to the other side. I can always come back to finance if this is a disaster in 12 months. And so I left Goldman and I was looking at a few things at the time and I realized I kind of wanted to go to something really, really small so I could just sponge and learn everything. And at the time actually someone was like, you should join Uber. was maybe 12 people at the time. And we were talking about Uber.
Keith Cline (23:40)
No, really?
Sasha Hoffman (23:43)
I been introduced through one of the VC partners in California and Silicon Valley to Plastic, which is in Boston. And at the time, you know, it was like barely pre-seat. And I had met Elliot, our CEO, honestly, in an airport we were like transitioning through and we were sitting there on napkins and he was trying to explain his business on napkins. And we both ended up just meeting in the airport for several hours. And that was our first meeting and it just carried on. he was like, and I kind of looked at it, was like, it’s probably either gonna be a huge company or a bust. I’m not sure which, but let’s take a chance. And I can be there as this company raises money and I can see every department and learn honestly on somebody else’s dime how to grow. And so that’s what I did. I moved from California at the time I was in San Francisco to Boston. I had been to Boston once in my life. And when I moved, I was like, I’m not gonna buy a winter coat. I’m not gonna buy boots. I’m not gonna be here long. Like, let me just test this out and to note that I went to Boston in 2012, I’m still in Boston. And it took me eight years to a winter coat, because the logic stayed the same. But yeah, so that’s what kind of got me originally into startups and to Boston and to Plastiq
Keith Cline (24:44)
Right, right.
HA!
Well, then, and Plastiq did end up moving to San Francisco, but you stayed and then landed at Piaggio Fast Forward.
Sasha Hoffman (25:05)
Yes, it did. at the time, so about two plus years and they got an investment from the West Coast, Khosla and a few other funds and the funds were like, hey, you need to come out West. And so they moved out West. And to be honest, a lot of the teams stayed behind or just didn’t stay with the company because they just didn’t want to move. And at the time I had like really started to enjoy Boston. It was an interesting time. A lot of great entrepreneurs back then. It just different generation of people, many of whom are gone now, but were wonderful. And I just built a community and I was like, hey, I actually really like the startup universe.
I don’t want to go back to San Francisco. I had had a life in Boston and so I stayed You know, I’m obviously so in touch with folks there And if I’m being honest like several of my best friends in life now came out of Plastiq. They were the people who sat next to me I’ve now been in their wedding and so, you know I never take it back because truly I think I met like some of my closest friends in life is sitting in that office for two and a half years and so now that’s yeah, I ended up staying behind
Keith Cline (26:03)
So I remember ⁓ working with you with the launch of Gita, which was the personalized robot from Piaggio Fast Forward. So I guess for context, if people don’t know Piaggio, this is like the scooter moped company in Italy, right, Piaggio?
Sasha Hoffman (26:19)
Yep.
So Piaggio is a publicly traded company.
They own a variety of scooter motorcycle brands. Their most famous is Vespa, if you’ve heard of that, but they also have Moto Guzzi and a bunch of other brands. They’re quite iconic in the land of motorcycles and scooters, especially if you’re in Europe. But the family that took it over, bought it and they sort of rolled up several brands. So it wasn’t Piaggio Group before. They put them together and then made that brand. They honestly turned around the company. It was like a huge turnaround because at the time when they took it over, all the manufacturing was still in Italy.
They outsourced a lot of that to Vietnam and they really improved a lot of the profit margins of the company. in the US, they had had a division that was selling, you know, their products. They also had a design center in California for a lot of, for, for Aprilia, which is another one of their racing motorcycles. And they had just wanted to do more in semi-autonomous, autonomous tech and just what is the future of mobility? They had moved people for a long time on two, two and three wheels and they felt like the future was also going to look like that, possibly autonomous or not, but they wanted to be in the middle of that. And so we set up a new enterprise in Boston called Piaggio Fast Forward
Keith Cline (27:31)
And Gita, like it did still exist today and it’s only expanded into its use case and functionality. But this is, you know, 10 years ago, right? Like, or around that timeframe. So this was early, yeah, early days of robotics. Like what we see of robotics now, it’s amazing. But I mean, that was amazing back then and it still is. So.
Sasha Hoffman (27:41)
Yeah, it was.
Yeah, so, you know, when we originally were building the product, the original thought process was actually just what can we build on two or three wheels that can help move people better so that we can stop using our hands? And yes, the Gita application that you saw is the sort of consumer type version, but a lot of it was actually B2B applications. It was how do you use, whether it looked like that, you don’t see a lot of the other versions that existed that didn’t look like that, but they operate in warehouses and other environments where you can map the spaces and then they follow workers to help carry goods around. So really the premise was how do you free up a human’s hands so that they can do more intelligent tasks and let this thing carry things and use computer vision to follow you. And so we were early in that trend, right? I mean, I’ve always liked being early in trends and I was working on computer vision and semi-autonomous technology in 2015. And so that was also the time a lot of these autonomous cars were coming out. You remember Cruise. That was the time of all of them as well. ⁓ And so, yeah. The technology still exists today, most of it is actually B2B applications, but we’ve all seen, you remember Kiva Systems, but like Kiva was obviously automated warehouse robots. This from a similar presence, but with humans in the loop and semi-autonomous was sort of the thesis that’s still there.
Keith Cline (29:09)
So you did land at Uber afterwards during a very unique point of time in our whole world’s history during COVID, right?
Sasha Hoffman (29:17)
Yes, there’s some stints in between, but yes, let’s go to Uber.
Keith Cline (29:21)
Yeah,
so what did you, like, so talk about that experience there.
Sasha Hoffman (29:24)
Yeah, so when I went over to Uber, know, my timing couldn’t have been worse, not their fault, just the world. So I had joined right around the start of COVID. So I had left Boston at the end of 2019 and me and my partner had moved to San Francisco or had moved California at the time. And I got this job at Uber and I was really excited about it, but.
Keith Cline (29:31)
Right.
Sasha Hoffman (29:46)
Not even three months later, the world had just completely changed. And so at the time I was, I had actually switched from my original job into the role that I became into over the course of this and the first kind of two months or so, but I was running a lot of their loyalty programs. So we had a subscription program, which is now called Uber One, which was the relaunch of something that I did. And then we had a rewards program. And then we had all of these partnerships with different brands. could get loyalty points connected. And so I, loved the act of this. One, I loved mobility. I’d come from working in transportation. I was really bullish on it a whole. I was an Uber consumer. I also loved loyalty. I loved points hacking. was like, okay, this is the intersection of all of my favorite things in one job. It’s like all the loyalty stuff plus mobility, it’s consumer tech. And I was just so excited about this job to start. And then the world just changed and no fault of theirs, know, lot of the rides business just went to zero. But you know, that didn’t stop. I was on something called a P zero, which is like a top priority for the company was how do you get subscribers? How do you get people to start going from being a rider with the business to being an eater and starting to use us for grocery? And if you remember this time, it was like a war between DoorDash, Instacart, ourselves, anybody who’s in this market doing food and grocery delivery just wanted to win the customer at all costs. And so we’re dumping incentives and I was running all sorts of loyalty initiatives and incentives to try and get those people who are riders to become, become eaters. So the beginning days were, it was just, it was kind of crazy. mean, attrition rates were really high across the valley for anybody who was affected by COVID heavily.
So I think there was an HR thing that was just, it was a crazy time to be somewhere. I had like had a lot of bosses in a very short span of time at a very high at like, you know, the sort of C-suite comparatively. And so it was just a busy time period. And I don’t know that I’m alone in feeling like COVID was a crazy time for a lot of people’s jobs. I think I was just a company that was highly affected by it and needed to start making really quick decisions to try and win. Cause they were a publicly traded company.
So they had no choice. They were actually in very different position than DoorDash and Instacart because they weren’t private. So what they did was scrutinized. And I think, you know, to to empathize, frankly, it’s it’s hard to be a public company in times of economic distress in a way because you still have to produce quarterly earnings. And when people are breathing down your throat, mainly investors, your decision making changes a lot because you can’t think a year and a half out and be like, just trust me, just trust me. That’s not how the street works. And so I think it was it was tough for the business to need to take a long term approach and act the same way DoorDash or Instacart was, they literally didn’t have the luxury to do that.
Keith Cline (33:05)
So what did you learn? What were your takeaways from? I mean, this is one of the largest loyalty programs in the world, like Uber, right? That scale, right? So what did you learn there around loyalty subscription programs and retaining users, things like that?
Sasha Hoffman (33:18)
Yeah, a couple of things. So one, I did a full overhaul of the program. So when I came in, I felt like the loyalty program was not understood well. Truthfully, we went and we surveyed our users. They couldn’t tell you what the benefits of the program were. They were confused. ⁓ And so the first thing I’d say is, you know, don’t, whether it’s a subscription or a loyalty program, most people just focus on one thing that they remember as to why they attribute value to anything. And this is true of like all frankly, loyalty programs. If I were to ask you to name your favorites and why you usually just come up with one max two things that that delivers as value and that’s actually all that’s needed and so for any program the more you confuse it and dump benefits actually the worse it is and when I think about this I think a lot about credit card loyalty programs as well like I have a Robinhood card and I love it because it’s just 3 % back it’s so easy to understand I actually need no other benefit that they have it’s straightforward it’s understood I love it’s a very high cash back number then I think about chase and my reserve card and the other cards or like my Amex Platinum card and honestly, it’s a headache to remember all the benefits to go through and they do it on purpose, but for paid subscription programs or paid in credit card programs, I often feel like having one or two hero benefits is all that is needed to truly get a customer to understand what you’re doing. The second thing is reinforcement. So one of the big changes we made across the program, and you’ll notice this now, if you’re a user, then, you know, pre 2020, frankly, was we started telling you all of the money savings in the app. So when you book a ride, how much did you save because you’re a loyal to your subscription user at the end of the month, how much did you save at the end of the year? How much did you save? Reinforcement of savings is one of the biggest drivers of people continuing to use a program subscription rewards, whatever any paid program when I get an, and you know, my, one of my rewards cards, when I get a note at the end of the year, that’s like, you saved $2,000 this year because of this program, but it only cost you a hundred dollars. You just feel great, right? You’re like, yes, money saved. So truthfully anybody’s loyalty program, you must create
Keith Cline (35:13)
Yeah.
Sasha Hoffman (35:17)
Reinforcement at every step of the journey. So while you’re looking at the product, while you’re going to check out, after you’ve checked out in the receipt, and so I did a loyalty, I can’t say who, but I did a loyalty product for a very, large celebrity brand. And one of the biggest things was when you go to the product pages, seeing a different set of pricing for a loyalty member.
Costco is another example where you could get a different set of pricing because you’re a Costco member. And I’m a really big believer in this because it makes people feel better about that spending or moving into like a different tier of if I move up from gold to platinum to whatever, I unlock these other benefits. So that unlock key and showing differentiated pricing makes a huge difference for consumer behavior and change in behavior. The other thing I’d say about loyalty programs is you want to focus on making sure the customer understands ⁓ what value, not just what value they’re getting, so they’re getting these one or two things, but in order to consistently get them to stay there, if you can change how they purchase, so let’s say it’s an annual, let’s say you normally do monthly plans, but you’ll give an annual plan for, you know.
30 % of the price, lock people in for longer, because then they just forget about it. And so we made huge pushes, whether it was on ⁓ Black Friday or Christmas or whatever it is, holidays, how do you get people to buy an annual plan? Because once they’ve done that, you’ve truly locked them in. And then a lot of your marketing just needs to come at the end of that year to make sure that they’re actually going to re-up and that they know all of the value that they got. Those are like probably some of the big ones. I also tend to think if you can find ways to use a partner network to get you more users or to get them to get more value. Like when I was at Uber, we signed the Marriott deal to get your Marriott points on Uber. You see this a lot with credit cards. People actually love it. Like, you you sign up for credit cards sometimes just to get status on an airline or a hotel or whatever it is. And that cross promotion can make a huge difference for some users. Not when you’re talking about like tens of millions, but it can make enough of a difference.
Keith Cline (37:27)
Yeah, that’s great points. All right, so you’re a partner now at Remus Capital. So how’d you get involved in the investing side of the world?
Sasha Hoffman (37:35)
Yeah, so after my stay in San Francisco, I thought about, okay, I was traveling, truthfully, all of COVID, I was mostly remote. The business, obviously, we were all out of the office. And so I used that as an opportunity for kind of us to be everywhere. And I loved it. I’ll never get that chance back. I have never gotten so many cheap deals as those first two years of COVID. And then after that, it skyrocketed. But one of the best decisions I ever made was to do all the expensive trips I’ve ever thought about those first two years.
Keith Cline (38:05)
So what was your top trip out of those two years?
Sasha Hoffman (38:08)
I was in Africa for months and I loved it. mean, I did, we were literally on a private plane going around Africa, around like Namibia and Botswana and everywhere. And I got it at no joke, a 10th of the cost of what it should have costed. And there was like a group of us that went, I will never be able to replicate that trip. I just, I was like alone on the Sossusvlei dunes in Namibia.
Keith Cline (38:11)
That’s so cool.
Sasha Hoffman (38:28)
I was is never going to happen again. I mean, it was just unbelievable. And you have to take advantage of situations like that when they happen. It was also a great time to buy in the market, but hindsight’s 20-20. But truly, I was like, I’m not going to get COVID when I’m sitting with lions in the middle of Botswana. There’s no COVID happening here. I’m not worried. And so the more remote I went, the more kind of like the higher end the trip, actually the cheaper it was because nobody was going. And so I use this as an opportunity to just go ⁓ and now be like, where’d you
Keith Cline (38:46)
Right? Right?
Sasha Hoffman (38:58)
You go, what’d you do? And I tell them the trip and I send them the itinerary and they go get it priced and it’s genuinely 10X what it was. So I feel better about my purchasing decisions. yeah, I thought at the time, like where do I want to go back to? I had been in San Francisco, I’d been traveling and then I was like, okay, I’ve done enough out of my suitcase. I just need my home back. And honestly, I’ve always had a love affair with Boston. It has its issues, but.
It’s like a big place I call home, truthfully. My parents, none of my family lives there, not a single person lives there. And I still always though, to this day, I’ve met some of my closest friends there that felt like my chosen family. And so when it was time, I was like, I think I’ll go back. And I had looked at like, Head of Product roles at some consumer companies. But as you know, like Boston has a limited consumer ecosystem and also at the beginning of 23 was just bad timing and It was just not the most ideal time to also go into some of those companies a lot weren’t doing well and I had missed being in office, know, I had just I feed off of people I liked being there and I just I was like I kind of I want to be back in office and so I had looked at different opportunities there and I had known the Remus team for over 10 years and they were like why don’t you try out the VC side? Like you’ve you know what it’s like to invest raise tons of capital from being at high growth startups. I had advised a ton of companies.
I had invested in startups. And so was like, okay, like I think this could be really interesting and I can spend part of my time operating and helping our companies and part of the time investing. And so that’s what happened. I came over to the VC side since, and I probably spent a split amount of time between helping our companies with expansion and go to market, the LP and the fundraising side and opening up relationships, which I had never done prior to that on the LP side. And then the actual investing side and looking at companies.
Keith Cline (40:42)
Obviously we’re in this moment of platform shift to AI and Remus is kind of like the thesis from what I gathered is vertical AI. So what are you finding interesting these days in that world? There’s so much going on.
Sasha Hoffman (40:56)
There’s so much going on, and honestly, two and a half years ago when I had started, it was very different than where we are today. So as a fund, just to bring you up to speed, we invest in vertical AI. We do all B2B. We do pre-seed to series A, mostly seed in series A. And we look at businesses that honestly fuel America. We do a lot in construction, industrials, agriculture, health tech. So we are big believers in voice AI. So this fourth fund, which we’ve just deployed out of for the last two years, that fund is heavy on voice.
This thesis because voice is the most native thing that we all do. And I have a thesis personally where I felt like even several years ago as AI was starting to come up, I thought to myself, I’m not gonna use a device in the same way I use it today. In fact, a couple of years from now, and maybe at this point, it’s within two years, it’ll be good enough. I will just talk to my personal assistant, whether it’s through Gemini or through OpenAI or through another platform. And I will just talk about my whole day. I will ask it questions. It will then go interact with other AI agents that are vertical specific and get my answers and it’s very natural. It’s, just want to talk and it will eventually be good enough that you were holding a full conversation and it’s doing what’s needed to be done. And so the beginning stages of that was us investing a lot in vertical AI. We did not do any horizontal. So as a fund, didn’t do, you know, the OpenAI’s of the world, but we did go invest in some of the first voice AI companies even 10 years ago out of earlier funds that now, you know, have gone public and are fine, but.
This fund was really focused on that. And we have some of the top voice AI companies across different verticals and home services and front office healthcare and back office healthcare, scribes for various clinical work. And so we really just took a broad approach of saying, how does voice AI affect all of these different industries? And how do you get a specialized business who really can build a deep moat and won’t be displaced because they own the customer. They have that verticalized information and moat and they, you know, and so we felt like it was actually vertical in the end that was going to win a lot of these sectors.
Keith Cline (42:58)
Yeah, I do think voice is absolutely having its moment. I am seeing consumers and how they’re using voice way more than the past because I think the technology is better. And I think we’re on that short timeframe where if you’re trying to interact with your bank or something, getting a live person is going to be like, ⁓ like versus like now you’re like, just, you know, I want to get a person that I can talk to. I think the AI is going to actually get better where that’s going to be, you know, what you prefer.
Sasha Hoffman (43:25)
Yeah, and the truth is the AIs that are working also on, let’s say finance, right? It’s very binary. It’s a known answer. It’s math. And so I think some of those verticalized ones, especially when you’re talking about like, need to call my bank or I need to call my brokerage institution and ask questions. It should know answers. If I’m not calling about HR related stuff, I’m calling to ask it things about markets and other stuff. Eventually that stuff is all understood tax. These are all the things that are all too expensive for a lot of the average person.
So how do you get this to a price point that they can all afford? I think AI helps democratize a lot of that.
Keith Cline (44:02)
And like I saw, I don’t know if it was on the Remus website or maybe one of your posts, but it was like, say, see, do. So it was like say, meaning voice, see, vision AI, and then do robotics. So is that the threads that you’re mainly focused on that are good? Yeah. Right.
Sasha Hoffman (44:15)
Yep.
The entire thesis that was all a fund four was how do we, and sometimes those become interconnected systems. But yes, the idea of say is all the voice AI, which is the primary part of the fund seeing is all of the vision and computer vision and then doing as robotics. But in this case, let’s imagine a restaurant for instance, as a use case, if you’re going through the drive-through, we have an investment in a company called Presto. They were voice AI at the drive-through. Then you get up to the drive-through. ⁓ It’s using computer vision on the backend to look at how all of the staff is working and optimizing their workflows and then it’s potentially using robotics as machinery to actually make part of the order. So we think some of these systems eventually get completely interconnected and they’re owned by the same owner or company, and then in other cases they’re disparate systems that work together, or they don’t, but that they’re utilized by any given business to maximize efficiency. And so we’ve had this thesis for a while and it’s panned out quite well, so I think it’s doing good.
Keith Cline (45:14)
What do you see ahead, like the next two years? Like what are you really excited about?
Sasha Hoffman (45:19)
I don’t know if you’ve used OpenClaw yet, but I love this idea of you gotta get on there, it’s gonna change your life. It’s like change everybody’s life in two weeks, my own included. And so I do think that.
Keith Cline (45:22)
I haven’t, but I read about it all the time.
So tell me about it. So what has your experience been with OpenClaw?
Sasha Hoffman (45:37)
So I’m newer too, because I just literally started in the last week, but I’ve been watching a lot of my friends do it. And for their businesses, it’s been amazing. mean, it’ll connect whatever Linux system you end up using through your… ⁓
PC or your Mac, it’ll connect and then you can set up so many things from it. I mean, it’s really incredible all of the sort of plugins of your own life that you can make it do. And for me, I’ve been trying to figure out just, you know, I have an assistant, but how do you, how do I just get more things done more efficiently? And so I just talk to it the whole time and let it through telegram or through WhatsApp, whatever you want to use, you can connect things and then have it actually talk to it and say, okay, I need you to remember all of these things and so I’m using it in that way. But I also, my friend has done so much on it in the last two weeks for their business. It went through their entire website, combed through everything, told it every mistake. It made like a full plan for how they can do sales better. It like changed writings of things. I mean, it’s unbelievable just how quickly it went through everything. And you know, it doesn’t sleep. It’s your 24 hour receptionist EA. So that’s just an amazing, powerful tool to have. I think if you, know, anybody truthfully, even if you don’t have programming skills,
You can hire someone for a few hours to help connect it to your ecosystems and it can do a lot for you. I think truthfully from like a sales perspective, from an EA type perspective, research, has actually like, it has opened up my mind in about one month. I might have said like my entire life has been automated and I will get back to you if it has for a follow-up post on how to do it.
Keith Cline (47:11)
Yeah, I’m going to need you to do a demo for my product management community because we’re doing all these demos of all these different products, which is so interesting for me, especially because I’m just like, what is so I was listening to a recent episode of Lenny’s podcast and he had the head of engineering for Claude. And the comment that stuck with me from that interview was he doesn’t write code for Claude anymore. It’s writing its own code for its own product. I’m just like.
Sasha Hoffman (47:29)
Yeah.
Keith Cline (47:40)
This is like, this is so much faster than like, like it’s, it’s a crazy how fast this is moving.
Sasha Hoffman (47:41)
That’s where we’re at.
Yeah, I mean, asked the question you asked around it. I mean, one from a voice AI perspective, I think that’s the direction we’re going is the phone isn’t obsolete. The phone is still an object that we’re using. But I do think we moved to a model where like most of us are just honestly talking to our phone. We’re not typing as much anymore for anything. I also think displays. So like I’m a huge believer in glasses and whether it’s Meta’s or somebody else’s a lot of people investing in that. I just think that’s the next framework that we moved from. Right. I mean, phone, now glass, I just, do think there will be manifestations of it that look good, are easy to understand, connect into your, connect into an earpiece. And so I think that’s kind of the next wave too. And then look, I think the biggest question is around what happens to all the jobs, right? I mean, look, for every industrial revolution that happened, better things happen on the end of it, it does create progression. I’m not worried about that. I just think that the AI wave moves so fast that the gap here is a little like, okay, do you upskill and train people on AI? Do you need to actually give them completely new jobs, what do you need to do? To me that’s actually the more interesting macroeconomic thing to be thinking about because…
We’re seeing very quickly just how AI is good at its job. It still needs correcting. I don’t expect it to be perfect, but it’s clearly doing enough. And it is in fact able to either accelerate a human in what they can do or just replace what they were doing. then what do you actually, how do we help move everyone up and upskill them or give them new jobs such that we still have everybody working? Cause I think that is the goal.
Keith Cline (49:19)
All right, well, the markets, ⁓ we’re waiting for the public markets to hopefully open up and we see some big splashes like the Stripe’s or OpenAI’s go public or the SpaceX combo with Elon and Tesla and all that. But you had an exit, one of your portfolio companies, ⁓ Equipment Share. So yeah, so talk about that IPO.
Sasha Hoffman (49:32)
Thanks
Yeah, we had a great exit.
Yeah, so we had a company called Equipment Sharego Public at the end of January. That was a Fund 3 position for us that we’ve held for over 10 years. So whenever people talk about, all these things are exiting immediately, I would like to just send a reminder that most of these actually do take about 10 years. And so that just went for over $7 billion. So was a very good outcome for the fund. It’ll net Fund 3 at about a 10x DPI, which is a very, high number for a fund puts you in a very, very top position as a VC fund in the country. So great news for the fund. That was not my investment because it was long before me but kudos to the fund itself who obviously benefits from this. But yeah, mean look we’re also lucky that a lot of our positions from Fund 4 as well are doing very well. Many of them have hit unicorn status. Hopefully a couple become deca-corns but you know I think people, the markets are opening truthfully. Obviously we’ve just seen a huge sell-off in software but I think it’s a little bit of an overcorrection if I’m being honest. Some of these have really strong fundamentals underlying especially some of the cybersecurity stocks that just sold off. I don’t necessarily know the Claude’s new product is going to just completely wipe them, decimate these products. And so I think there’s actually probably a little bit of a buying opportunity in all of this dip. And look, there will be some companies that just disappear. This is 100 % accurate. But I think there’s been a bit of panic selling that’s happening at this current moment in time. ⁓ But yeah.
Keith Cline (51:00)
And outside of Remus, you’re also an active investor through other funds or angel investing. So talk more about that and how you get access, right? Like just me being involved in the tech ecosystem, I just wonder like, wow, how did you get involved in doing that?
Sasha Hoffman (51:19)
Yeah, so access as a whole just comes from the fact that one, mean, I’m in the VC space. I’ve been a tech entrepreneur. ⁓
I’ve been working for 17 years, so I just met people around the block. So a lot of the access just comes through network and keeping in touch with your networks. And thankfully, my events actually do act as a huge flywheel. I only do for a year, but the truth is they open up huge networks for me every time I do them, because on average, there are 100 to 200 people. So suddenly I just opened up 400 new connections for me. And so that’s how a lot of the access has come. But yes, we invest through there’s another later stage fund where we do deals called Starbridge, we’re a consortium of several hundred C-suite execs and execs at mostly fortune 1000 companies and our value add when we get on cap tables is that we can then open up true enterprise relationships at the C-suite and The most of the folks are in the US but they’re they’re also some global and we’ve done deals. We did OpenAI, Perplexity, Cochlear, Databricks, some other things as well. Sometimes we’re directly on the cap table sometimes there’s a secondary position sometimes we’re going in with another fund and we’re taking a piece of that block. But we’ve been very fortunate that like truthfully we had access to some of the best deals possible over the last two years. And so we got into some of them quite early too. So we’ve seen that balloon valuation. Of course, all of these companies need to exit. I would like to send a reminder that all of this is on paper right now. And if you’re selling secondary, you are exiting and you are making your money. But if you don’t and you’re currently still holding all these positions, they do need to exit. So we’ll see what happens. Maybe that’s this year, maybe not, but there’s a lot of also just amazingly valuable private companies, Stripe, Databricks, there’s so many that, truthfully, I work worth more than many public companies and their shares are quite liquid, frankly, if you wanna sell a block in secondary. And so you can get out if you are an investor and hold those positions as well.
Keith Cline (53:14)
How does one get started as an angel investor? What advice would you have there?
Sasha Hoffman (53:18)
My actual advice is don’t, my advice is just invest in a fund and let them do their job. I like love it whenever I need to do it. I’m just, I’m going to be honest, unless of your, unless of you know a sector super well and you’re like, I am truly qualified to invest in this because I understand it. And I’m now seeing technology that I think is going to have outsized returns. You’re basically gambling. It’s no different than going to Vegas and spending $10,000 on slot machines.
Keith Cline (53:25)
That’s good advice, yes.
Sasha Hoffman (53:45)
The probable fire at the MGM. And so I think right now everyone’s so enamored by the AI wave, right? But the truth is like…
Keith Cline (53:45)
It is, you’re so true.
Sasha Hoffman (53:55)
These opportunities only come around so often. But funds are actually paid to do this for a living. And sure, maybe you don’t get 100X return, but maybe you invest in a pre-seed, early-stage seed stage fund with people that you know that you’ve met that you trust. And if you trust their judgment, maybe they return you five to 15X. Maybe you get lucky. Those are great returns. It’s much more than you’re doing in the market. And the reality is lot of those funds on first and second funds actually
Keith Cline (54:19)
Great.
Sasha Hoffman (54:25)
if not everybody, but you invest with somebody good, they actually do have really, really high returns. They’re much higher than later stage funds because those funds are much more beta. So like much closer to two or three, the later you go, they’re obviously de-risked. But those first and second early stage funds and those that invest in pre-seed and seed, those usually have the highest multiples. And so my advice is, look, if you just want to throw X amount of money at some friends because you’re excited about what they’re they’re doing you believe in them or you’re like I think I’m at game-changing technology and I know this sector by all means invest in it. But otherwise, this is actually not a very good strategy for having long-term sustainable returns your better option is to go invest in a couple funds whether you put in a 100k 500k However much you’re planning to invest as an aggregate in angels go deploy that separately into several funds that gamut that go along the spectrum of the stage deployment, so early stage to mid to late, and just sit there and wait 10 years. And if you’ve turned around that money, your IRR is still better than honestly you probably would have done on your own or in the markets. The only people who don’t have this response are like, ⁓ I was one of the first investors in Coupang or whatever. And the truth is you were probably business school buddies with a friend and that’s how you got in. And that goes back to my thesis of if you really like someone and they are your friend, go invest in them. But most people’s random obscure, like the average person, isn’t going to generate those types of returns.
Keith Cline (55:49)
I can attest to that. I am the average person that has made a few angel investments that I think one’s still active, but it’s just, it’s there, you know, maybe, I don’t know, maybe, but yeah, it would have been much better to go to the pros that are actually in the fund building a portfolio.
So, all right, let’s talk about travel. So you’ve talked about different pieces throughout this conversation of traveling a lot. think you, in an email exchange, you said you’ve been to 106 countries, which is extraordinary.
So how do you balance work, remote work, hacking travel? all, mean, there’s a lot to that between having a job, responsibility. So how do you manage to do all that while having just that fulfilled travel lifestyle?
Sasha Hoffman (56:37)
Yeah, so the first thing I should say is a lot of the travel I’ve done when I was younger, probably the last couple years I’ve traveled less. But when I was young, when I was in high school, someone asked me this really pivotal question. They were like, what do you want written on your tombstone? And I just thought it was like a really good way and perspective to put what is it that you actually wanna focus on in life in one sentence. And my response essentially was I want something written that I travel the whole world and help people also travel the world with me. And so that kind of speaks to a lot of the luxury travel I did,
So my love of travel and just traveling with my loved ones and so forth. so ⁓ I used to just make it a big priority. Frankly, I always took my vacation days in every country. ⁓ When I did travel, it was like, I just did as much as I possibly could travel. And I have a whole family that loves to travel. So all growing up, we love to travel. And then any time for work, I mean, when I was in finance, we traveled all the time. I would just add an extra day and I’d be like, okay, I have meetings Thursday, Friday. I’m staying the weekend. I’ll come back. It didn’t matter if it was a red eye, if I had to travel, two in the morning, no matter when it was, I just got on a plane to go. So I think this was very innate to me was to say I wanted to see the world before I died. It was like the number one priority that I had. So very few people get to 106 countries. It’s very much done as a purposeful thing. You can consider it another job. But now that I’ve done it, I could take a step back. So remote work is honestly pretty difficult while traveling. The only time I’ve done it is truthfully when I did it over COVID.
And I did notice if you’re gonna do it, it is better to stay in a place for like a month to a quarter. So like right now, for instance, I’m in Dubai and I’m here for the quarter. It’s really hard to just make a home for yourself and work responsibly if you’re just on the go every day. You can’t be switching hotels. Like that is not a thing. And last summer I was in Europe working for like two months and it was tough because I did need to switch more than I liked. And it was very draining. So the first thing is if you’re gonna remote work, try and stay in a place for at least two months and get an apartment.
Make the rest of your life the same as it was back home. So if I went to the gym in the morning, I did breakfast in the morning, do all that same routine to reduce the amount of variability in your schedule. Because if you just toss up, okay, I’m gonna spend half my day traveling and then, or exploring and then half my day working, you’re not, you’re just gonna be tired. It’s easier to say I’m spending Monday to Friday doing my work week and then I’m spending the weekend exploring wherever I am, which is traditionally what I’ve tended to do. I just happen to be wherever I am as I’m doing that. ⁓ So that’s kind of my first tip on remote work. The second is there’s a lot of deals you can find. Travel’s so expensive right now, and I’m saying that as someone who loves finding deals. Even if I’m buying luxury stuff, I like to do it at a discount. My nickname is The Hinjew because my mom is Indian and my dad’s Russian, Polish, and German, and so I love getting a good deal. So ⁓ I love looking for that. I think now if you’re willing to go, so like last summer when I was in Europe, I was in Budapest, which has amazing pricing, and you can get like, I got a like, like a residence suite in a hotel – amazing and super central. And so try and look for places where you can also just go more bang for your buck. If you go to Paris in the height of their peak season, you’re spending a lot of money and then you will feel bad. You’re like, I’m not out exploring. If you’re not paying as much and you’re somewhere where it’s nice, like you can get great deals in Mexico city and in Cabo. I I tend to just look for places where you’re excited to go out, but you’re not jealous or having FOMO of yourself and the life you could be living if you’re spending all this money, like going out potentially every day.
Invest in a good VPN because I still need to be able to invest in any VPN because a lot of what you still need to access back home, you should do it through VPN. ⁓ I have got every single international, I’ve got so many eSims and all kinds of other things that I use as well. And then I love Rakuten. I mean, it’s amazing. Every year I at least get two vacations fully for free just because I’ve done cash back on so many things or like points accumulation and so I’ll double dip and everything. So if it’s, you know,
I’ll check Rakuten to be like, okay, who has 10 % back on hotels right now? And if it’s like Hilton or Go to our Priceline, I’ll go there and then I’ll use whatever I already have with them. Plus I’m getting an additional 10 % back. You can double dip into lots of things. Plus I’ll get extra points on credit cards and other stuff. And so, you if you spend a little bit of time upfront mapping out some of this, it’s actually amazing how much you can get back on your trips.
Keith Cline (1:01:01)
And are there like websites that you go to that have a lot of these deals? Like, or are you just randomly because you consume so much information because it’s such an interest of yours?
Sasha Hoffman (1:01:10)
So cash back, mean, if you don’t have Rakuten, everybody should have Rakuten. You can just get the browser extension and anytime you’re on any website, it’ll tell you if there’s cash back. And what I’ll do is if I’m going to like a trip and I know I need to book X hotel, I’ll just go to Rakuten and like also type that in and see, okay, it’s 10 % or I’ll just write hotels and I’ll see 10 % back on Priceline, 3 % on Agoda and then I’ll just go book it on Priceline because 10 % back on Priceline. So from a comparative tooling perspective, just on cash back, I use that. Actually now, thanks to AI, I use it all the time to ask me deals. I mean, I’ll be like, I’m, you know, I was going up to Saudi for something and there were like four hotels I was considering and I’m telling the Gemini bot instead, can you go check pricing on all these sites? And then can you go check like all the third party travel sites and see if anybody has it cheaper? Where are you seeing it? And it’ll check Metasearch and I’ll come back with results. And so I’ll get, I’ll be able to see what it’s doing. The one thing it can’t do is it can’t log in what you can tell it to and write a script.
But as of now, it’s not like logging into Amex rewards, Chase Ultimate rewards to be able to check like what’s going on. But that OpenClaw can do that for you. You can now get other things that do that for you to check. But yeah, I mean, it’s actually, and there’s also just, so the truth is luxury travel right now is not suffering because the gap between the rich and the poor just got massive. But if you actually want to do budget travel, things are looking great for you. And so it’s amazing how many new deals are coming because the market is starting to get softer, right? That’s the reason why consumer discount sites like Ross Dress for Less and others are doing better in Walmart and Costco. Like it’s times like these where you start to see the softening economy and people are feeling price pressure. So actually budget hotels are mid-range, are starting to see massive discounts right now. And so can get great deals on that if you were interested in that as well.
Keith Cline (1:03:04)
You should just do a podcast on this.
Sasha Hoffman (1:03:06)
Love to. All day long. That’s all I think I need to do. Just tell everybody how cool it is to go see the world.
Keith Cline (1:03:09)
Travel with Sasha. Yeah, exactly. I need to do more of that. Well, Sasha, thanks so much for taking the time to walk through your experience. Obviously, all the great advice and all the work that you do as an investor and obviously all the great tips.
Sasha Hoffman (1:03:24)
This was awesome. Thank you so much, Keith. I’m glad we finally did this 10, 13 years later, better late than ever. Thank you so much.
Keith Cline (1:03:30)
Thousand percent!