
Raising from Friends: Sam Sterling the Serial Founder
Chris (00:01.459)
What's up founders. Welcome back to the show. I am your host Chris. We have very special guest, Sam Sterling here today. I'm super excited. I saw her on Tik Tok and I was like, I got to have you on my show, Sam. Welcome to the show.
Sam (00:02.158)
Thank you so much for having me.
Chris (00:17.385)
So to get started, tell me about the moment you decided to start your company. Like when did you have that, that just idea just pop into your head? For me, my ideas can come when I'm in the shower or driving or sometimes falling asleep. Like, what was that like for you?
Sam (00:33.798)
I really wish that I had this beautiful kind of aha moment and I was like, I absolutely have to pursue that thing. But essentially what happened is that I was working on another startup. So just to back up a few years, I was working a full-time job in kind of a consulting role and I had this like idea that I was really passionate about and I was working on it with a friend of mine.
like on the side, a, you know, the classic side hustle type thing. And it was never, it wasn't something that either of us were like particularly prioritizing, but it was something that we were working on and we were both quite excited about it. And then I pretty spectacularly lost my job in a round of redundancies as the company was downsizing and
Chris (01:07.891)
Yeah, yeah.
Sam (01:30.227)
Then my friend that was working on it with he actually quit his job. And so I was like, Hey, maybe this is the time we do this full time. But he was like, unfortunately I have bills to pay. I can't go full time. And so I was like, okay, like maybe we can do it more than we were though. And so I took on some consulting roles. He ended up taking on consulting roles that turned into a full time role and we were both working on this on the side.
And then another friend that I've known for a long time came on as a, like in like a, like a late, I don't know how you want to put it, like a late stage co-founder for one of a better word. And so we started working on it more and more and then he was going to relocate. And I like realized that I, someone couldn't be relocating to work on this project and maybe still treating it like a side hustle.
Chris (02:10.782)
That makes sense.
Sam (02:25.151)
So I dropped all my consulting roles and went full-time on this thing. I had a teaching role because I'm an adjunct at NYU and I sit on some boards. But other than that, this was like my full-time job and I was throwing 60 plus hours a week into it. And it was like all consuming and I was like, it was all I would think about, you know, like the whole, the whole routine.
And then in a very unpleasant series of events, we ended up with some co-founder issues, which is very, very classic. But this was someone who had known a long time and I just didn't think it was going to happen to us. And at the same time, some advances were made in AI that was going to, that were going to put the business in a challenging position, mostly in terms of
Chris (03:09.374)
All right.
Sam (03:23.489)
consumer perception rather than in terms of actual capability. And all of this came to this spectacular head. And I just realized that this, like the amount of money and the amount of time that was going to be required to get this to kind of launch speed, like that real moment where it wasn't just like tipping along, but it was actually going to get to that inflection point.
was something that I didn't have necessarily have the capacity for from a funding perspective, from a skills perspective and everything else. And so I had to make the really difficult decision to shut it all down. And at that point, we had 1200 people, more than 1200 actually, people paying to be on the wait list for this concept that we were building and we had a prototype for and all these sorts of things, like an MVP in play.
And then like overnight I was in this position where I had been pouring everything into this business. I had my teaching job, I had my board roles and that sort of thing which kind of kept lights on in terms of paying bills and that sort of thing. But this was everything for me. And I then went through this time, you know, spoke to my husband, we kind of workshopped it a bit and I was like, look,
I could go and try and find a corporate role or I could give this another go. And I decided that my background is in like innovation and growth kind of strategy and roles. I'd done a lot of venture building for other companies in my previous roles. And I was like, I really think I can make a go of this. The problem was I didn't have a specific idea. And yeah.
Chris (05:17.726)
And that was, that was my next question is about the problem. Like what is the problem that was so painful that you had to like double back and say, I gotta keep going. Like what was that issue you're focusing on?
Sam (05:30.795)
so two things with the new version of the company. Now, now what I'm doing is I'm actually working on more than one business at a time. and that's for, that sounds crazy to a lot of founders and it's definitely not like the norm, but to go from yet, but to go from that moment where I had been pouring everything into this and then had shut it all down.
I was like, I don't want to be in that position again where I am pouring everything into one thing and then I get to a point where I have to shelve it and start again. Like that doesn't feel smart. But also the thing that I've discovered is that unless you are full time, sorry, unless you are the one that is actually building the product, there's a lot of waiting.
So that gave me the ability to be able to do two things. So to back up and answer your question then, the two things that I'm working on now, and I started out with lot of ideas and I kind of validated and iterated my way down to these two. Now, one of them is in laundry and the other is in skincare. And the laundry concept basically stems from the observation that I have spent almost my entire career
making people want stuff they fundamentally don't need. I have a background working with some incredibly prestigious and very famous brands, Nike, Netflix, Lego, L'Oreal, Four Seasons, Lululemon, Apple. Like I've worked with all of these brands. And the thing is we spend so much time creating these brands and experiences around these things. And I fundamentally believe that the
boring parts of life deserve as much attention. And so now I'm looking to create a brand that isn't designed to be acceptable. It's actually designed to be enjoyed. And
Chris (07:28.286)
Mm.
Chris (07:38.897)
I like that. That's good. It's designed to be enjoyed. I like that. And specifically in this phase of AI, because I think a lot of the companies are designed to make money. It's the same thing. And some of them even make money. It's just to get more investment. So what stage were you in when you decided to raise? Like where were you in this idea phase? Cause you said you had a bunch of them and then you like whittled it down. So where were you in that process?
Sam (07:40.874)
You
Sam (07:53.491)
Mmm.
Sam (08:02.43)
Mmm.
So just for complete clarity, I said that I'm working on the two things, the laundry and the skincare. I raised for the laundry. I haven't raised for skincare yet. So with the laundry, I didn't intend to raise because I didn't think the way that I've designed the business and the business model that I'm going about, I didn't think it made sense to raise. I've had, I had people offer me funding, but the amount
that they wanted, that the amount of equity they wanted for the check that they were willing to write didn't add up. And so I actually had originally planned to finance it using seller financing by buying up laundromat of all things. And then I realized quickly that that wasn't achievable. That wasn't going to work with the business model I'd designed. So then I looked into getting a loan and the challenge that I had is that I'm
not an American citizen. I'm not a green card holder, so I'm not an immigrant. I'm here legally, obviously, but I think a lot of people don't appreciate that you can be a legal non-immigrant, and I'm a legal non-immigrant. And that means that almost all funding options weren't available to me. So I'm now in this very difficult position where I couldn't get a loan.
I what none of the standard avenues of like SBA loans, like government backed small business loans are available. it didn't, VC money didn't make sense for me. And I was like, do I, do I pull my life savings into this? Like, how do I make this work? And then a riot. And then a friend of mine said to me, like, why don't you do.
Chris (09:47.464)
Ooh, that's a tough question to ask yourself right there.
Sam (09:54.408)
like a friends and family round, but like actually just raise a loan through friends and family, not equity through friends and family. And I was like, maybe that could work. And because of my background, have a very comprehensive financial model, very comprehensive business model. I've de-risked it. I've validated like a lot of parts of it. So I put together a pack and sent it to like eight friends who are
knowledgeable about various aspects of this, either from a brand perspective or from a funding perspective or a finance perspective or whatever it is. And I just asked them for their input. And then amazingly, of those eight, I think six, five or six actually came back to me and said, hey, I'd go in for this.
And then even more astonishingly, two of them came back and said, the amount that you need isn't that much. Like I'll go in for the whole lot. And so then I, then I went from, had honestly, Chris, I had spent probably three months trying to figure out all the loans, chasing down every avenue, like for financing, all these things. And then in like 10 days I had solved.
Chris (10:48.573)
Wow.
Chris (11:00.049)
Wow.
Sam (11:18.022)
the problem by going through that down that route.
Chris (11:20.956)
I think there are two things right there that I think founders got to take note of is number one is a network. Being able to send it off to a friends is like that's super valuable having the right people you're connected to. And I think the second one is the skill because I got to ask you this. What did you put in that pack to make your friends be like, well, this looks good. I want to I want to be a part of this because I think a lot of founders could take this as their route to the funding their companies.
Sam (11:27.337)
I
Sam (11:49.65)
So a couple of things. One, the financial model is critical. And for me, when I built a financial model, every single number in that model, I have validated with three points of validation. So every single number in there, I can say that I believe that number is accurate to the best of my knowledge because I have at least three points of validation, like three sources.
And I've stress tested it. So those, those, those can be external sources of data, like reports and things like that. They can be data I've got from like businesses. They can be actual experiments that I've run myself to validate demand or whatever it might be, or I've actually done the research to know that's how much supplies will cost or whatever it is. So every single figure has at least three points of validation and every assumption in there has three points of validation.
Then the actual pack itself tells a story. And that's something that I really learned in previous roles was the ability to tell a compelling story about what I'm doing and the classic stuff, what it is that I'm doing. And some people say what problem you're solving, but let's look at laundry for instance. A lot of people would say laundry isn't fundamentally broken, but
So when then when you say the problem you're solving, the problem is that it is, can I swear on this podcast?
Chris (13:26.812)
Yes. Yeah.
Sam (13:28.731)
The problem is it's boring as shit. there is, there is nothing like fundamentally though, laundry sucks. And unlike many other categories, AI is not coming to save us. It just sucks. And we have to do it at least once, if not multiple times a week. And even when we send it out, we come back with, you get your clothes back that are shrunk, faded, sometimes have holes in them a bunch of the time it goes missing. And it's like, it just.
Chris (13:31.825)
Yeah.
Chris (13:57.052)
Yes.
Sam (13:58.713)
Everything about it is shit. And so a lot of people would say it's not broken, but in a way to me, what is broken about it is that so many people have spent so much of their time making all of this other stuff like activewear and running gear and soda and everything else beautiful and desirable and fun and everything else and we forgot about laundry. And taking people on that journey?
but then backing it up with hard data is a really compelling combination.
Chris (14:33.244)
Yeah, I agree. Because I, that goes back to your quote earlier about it being enjoyable. Now I get it. I get it even more now how you would make laundry enjoyable. And it's something that everybody is impacted by. Like everybody has to do laundry at some point. Very few people can live a life where they don't ever wash clothes. Like everybody has to do it. So it's something that your market is pretty wide there as well.
Sam (14:58.555)
The irony is that even if you send your laundry out, like let's say you have a like a housekeeper or you are in the inner position where someone else does your laundry, you still have to wear the finished product. And so you still don't want it to be irritating. You don't want it to be faded. You don't want it to be all of these things. So it doesn't kind of doesn't matter. Everyone has to deal with it, right?
Chris (15:23.518)
You
Yeah, exactly, exactly. So it sounds like your fundraising process was extremely unconventional compared to what other founders are usually doing with the process that you experienced. Is there anything you would like change about it?
Sam (15:37.017)
Mmm.
Sam (15:41.071)
Thank
Sam (15:46.711)
I probably would have found the courage to do it sooner.
Because I think I... I don't know if I didn't believe in myself enough or I didn't want to ask that of people or whatever it is but I think I would have found the courage to do it sooner. The other thing is that I've found so many times in my career that you can't steer a stationary car. Like if you don't have momentum
You can't change course. You can't do anything with that. You fundamentally need data to be able to refine literally anything. And so at least if I had tried sooner, I would have got data about that and I would have been able to iterate. But as it was, I was so stuck in the idea that I was going to go down the funding path.
that I was going to do it on a lone path. Sorry. I never tried. And the other thing is like for me in my head, the only way to raise was through like angels or VCs. And realistically, I am a, for the better part, first time founder. have built businesses in the past in a corporate environment and I have built my own business and sold it before, but it was in a very different world and a very different type of business. So for the best, for the sake of argument, I'm a first time founder and female.
I'm not in my twenties and I'm a non-immigrant. I'm about as unattractive as it gets. And I was like, I don't know that I feel like just going out and meeting with like hundreds of angels that are going to come up with all these reasons or like VCs that are going come up with all these reasons that this isn't the thing. Like it just seemed like it was going to be a lot of waste of time. And I was like, I can get alone.
Chris (17:23.271)
Yeah.
Sam (17:49.51)
to that kind, but I can get away. So that would be my thing. Start sooner and get more data.
Chris (17:56.944)
And so if you met another founder in your place, in your position with all of those criteria you just mentioned, what other advice would you have for them? Cause I think there are a lot of unique founders out there right now in that position. When you look at like Y Combinator, they're snatching up the same type of founder. have like a formula that they're looking for. So if you don't fit their format, they don't pay attention to you. You know, it's a lot of firms that are like that where they have a specific type of person they're looking for. And if you don't fit that,
get out the door. So I think your path was very unique. So what advice would you give to somebody that was in your position?
Sam (18:34.66)
I'll answer that in just a second but while I'm thinking about it I think a lot of companies like Y Combinator do do that. recruit a specific sort of person and it's easy to be critical of that because you're like they should have more diversity, they should think bigger, they should do all these sorts of things but fundamentally they have a product and they need specific ingredients and they're just baking that product with these ingredients. I don't think you would tell anyone that was like a baker.
for instance, that they needed to start using sardines just because sardines are, you know what I mean? Like, like, like you just find it like they just have a product. I, in terms of the advice that I would give, I think it would be to go as wide as possible. So like shake out every tree and I'm guilty of not even doing that myself, but like shake out every single tree. Like make sure you've at least
validated your assumptions. And the stupid part is, for all my own advice on that, I didn't even validate my own assumptions. But validate your assumptions. If you were convinced that you cannot raise through angels or VCs, go check. Check with like just 10 angels and VCs. Like go check. Check with your friends and family.
Chris (19:44.829)
You
Sam (19:59.298)
I didn't even get to my family, I was just going to France and I got this result. So that would be my advice, literally just go check.
Chris (20:10.053)
Yeah, I think get over that fear of asking or being turned down. I read a recent essay on preempting where some founders are like not raising, but kind of raising, just having conversations. I don't think that's a bad idea. They're saying it's bad, but I think if you're founder trying to test the water, it's genius. Go for it. Like that. think that's a good way to kind of set yourself up to see what you can actually get without fully going all in just yet. Kind of test the water a little bit for a week or two.
Sam (20:31.032)
Mm-hmm.
Mm.
Chris (20:39.323)
have a list of five investors you'll talk to and you can get some feedback a lot sooner versus trying to wait six months or a year. Your time can kind of pass you up really quickly.
Sam (20:50.135)
Yeah, I think a good way to reframe that, like getting over your fear of rejection or failure is to not treat it like a question that is going to have rejection or you're going to fail at, but instead look at it as data collection. Because if you can just be like, I'm just collecting data about what works and what doesn't and what triggers and what levers I can pull. And you just need to build that data.
then it really doesn't matter what people say because you'll still get the data. I think that kind of helps the mindset, I think, a little.
Chris (21:22.717)
Very true. Very, very good point.
Chris (21:28.509)
So where are you taking the company now that you've raised?
Sam (21:32.515)
So I said before I have a really quirky business model. Essentially, I ultimately want to build a consumer product, like a consumer goods product. But to get to that, I actually need a lot of data about what works and what doesn't. And it occurred to me the best way to do that, I live in New York, is to have a laundromat and use the volume of people and the volume of laundry.
to actually be able to act as a test kitchen, both in terms of what consumers respond to, but also in terms of effectiveness. So it helps that laundromats also have pretty decent profit margins and pretty decent cash flow. So I can actually use that to then snowball into product development. So it kind of works both ways. I have cash and I have the actual like test kitchen.
customers being able to provide very real feedback to be able to get their input. So what I'm doing at the moment. Yeah.
Chris (22:33.841)
I just want to say before you continue, that is genius. I love that. Cause if you can set up one business to, and it's cash flowing, you make money from it. And it's also preparing you for the other bigger kind of journey. I love that. I think a lot of founders want to focus on this one small thing for 10 years. And the way you're doing is just really creative. like.
Sam (22:57.219)
Thank you, but let's talk in a year and see if I'm successful. So what I am originally, I was going to buy a laundromat, but then I realized in order to be able to do what I want, I would have to pay more than it's like more than the value of its parts because I'm buying the business. And then I would have to shut the business and gut it and then build what I wanted to build in the same space. And that just
Chris (23:00.92)
Yeah.
Sam (23:25.515)
wasn't financially very smart. So what I've ended up doing is I'm actually looking to build one from scratch, which takes a little bit longer, but it has the benefit of having it exactly the way I need it to be. So at the moment I am looking for physical spaces and shopping for commercial real estate in New York is a vibe. my gosh.
Chris (23:50.954)
I know that sounds it sounds horrifying
Sam (23:54.498)
So that's that's been a process. We're working through that at the moment And I'm also working through the creative and things like that But the hope is that within the next kind of month or so I will have something locked down with regards to space and then we'll be able to work through the Permitting and all those sorts of things that's the stuff There's obviously a lot more to do behind the scenes but it also gives me the opportunity to really build a brand and I'm hoping that the brand
And then I have the opportunity to be able to build brand that one will build momentum around the physical, like the laundry service that I can then like slingshot into consumer product. So while we're doing permitting, because I'm obviously not a general contractor, I can like while they're working on that, I can be working on brand and we can go from.
Chris (24:41.373)
Hmm.
Chris (24:51.793)
love that setup. I love what you're doing. I got one more question. What do you want founders to learn from your personal journey? Cause yours is one of the most unique I've ever heard. So like, I'm very interested to hear what you want other founders to learn from what you've gone through so far.
Sam (25:09.729)
A few things. One, it's never too late. I'm in my forties. I have lived in seven cities and five countries. I have run multi-million dollar companies in some of the most difficult markets in the world, like China during COVID, Japan during COVID. I ended, I have a doctorate that literally no one cares about.
I worked my ass off to speak a language, a second language that no one cares about. I, it doesn't really matter. Like what your backstory is. You can always do this. There is always a way to like fear it out. If you are committed to trying and running, running experiments and trying stuff, setting your assumptions aside, like I was saying, and keep going.
But the other thing is, just start. You know that whole one day or day one? Like, just start.
Chris (26:22.522)
I like it. Just start, just get started. I talked to a lot of founders who have the idea, the insight, some of them domain authority. They've been in the industry for 10 years already, but they're just a little, I won't say fearful. It's more like worry. They're worried that it won't work out and what the embarrassment will look like if their company fails. And I'm like, most people aren't paying attention to your company failures. Like most people had their own stuff going on to where they aren't paying attention to your little company.
If it doesn't work, like if you do a launch and nobody pays attention, you can keep doing launches until somebody pays attention. That's the fun thing about being a founder is never too late. You can always keep going, try it again over and over again. There's really no barriers into this.
Sam (26:53.289)
I think it's.
Thank
Sam (27:00.896)
Thank
Alright, look, I really agree. I will say two things though. A lot of people worry that it's going to fail. It probably will. Like, the stats are not in your favour. It probably will. So if you can't make peace with that, let it go. Like, it probably will. But would you prefer to wake up one day in your 90s and have failed because you tried or have failed to try? I personally would have failed
Because I tried, I don't want to wake up in my nineties and be like, I never gave it a shot.
Chris (27:41.853)
You try. That's my biggest fear. Biggest fear right there. You gotta try. You gotta put yourself out there. man, this was really good, Sam. Thank you for being on the show. This was really interesting. Your story is just, I know from looking at your page that it was gonna be a lot, honestly. In a good way, in a very good way, because it's an interesting journey. let the people know if you want founders to support you. We have a lot of investors listening to the show.
Sam (27:51.284)
Thank you!
Sam (27:59.213)
Thank you. Thank you.
Chris (28:10.618)
Are you open to working with investors at this point or are you kind of like leave me alone?
Sam (28:15.008)
I will be taking on investment for the skincare brand, which we didn't talk about, but that is something that I will be doing. I will probably look to be raising a really small round next year. So definitely for that. My handle on basically everything is the serial founder, spelt like you think it is.
And yeah, I'm definitely open to conversations, but really importantly, I'm also very open to just other founders reaching out because I do really believe in network and something that I've found as I've moved as much as my, I have is that you're like, your network is everything and it's amazing who you can meet online these days.
Chris (29:06.525)
100 % man. This was really good. I'll make sure I put all your links down in the description box. Founders, thank you for tuning in. Make sure you follow the show. Connect with me on Twitter as well. That's where I'm at mostly. And TikTok. I'm getting more active on there. Let's connect. I will see you guys next time.
Sam (29:20.275)
Yes!