Lee: [00:00:03] Welcome to episode 73 of the Stairway to CEO podcast. I'm your host, Lee Greene, and today I spoke with Michael Mayer, the Co-Founder and CEO of Bottomless. Bottomless is the first smart coffee subscription. They help you build a custom coffee subscription, ship you a simple Wi-Fi scale to store your coffee on, and then send you your next bag of coffee in perfect time, never arriving too soon or too late. In this episode, Michael shares with us his entrepreneurial journey from growing up in Oregon as a triplet with dreams of becoming an inventor like his uncle, to studying engineering and economics in college, to landing a job at Nike and experiencing challenges as a consumer with his wife around restocking their home, which led to the idea for Bottomless. He talks with us about how they applied to YCombinator three times until finally being accepted, how his anonymous Twitter account helped him build relationships with investors and raise over $6.8 million, and how he's grown the business to over two million in revenue. If you like what you're hearing on the Stairway to CEO podcast, don't forget to click Subscribe to get updates on our new episode releases happening every Tuesday morning. Until then, we hope you enjoy this episode.

Lee: [00:02:07] Hi Michael, thank you so much for being on the show today. I'm really excited to hear your story in building Bottomless. Thanks for joining us.

Michael: [00:02:15] Yeah, I'm really excited to be here. Thanks for having me.

Lee: [00:02:18] Michael Mayer. You know, my husband's last name is Mayer. I'm actually technically a Mayer. I just didn't change my name. But good last name. Nice to meet you. Family. So where are you from originally? Where did you grow up? What was childhood like?

Michael: [00:02:33] I grew up in Portland, Oregon, so sort of like Native West Coaster, probably from the weirdest West Coast city, I guess. My parents were both writers growing up, newspaper reporters, to be more specific. They just had normal professional jobs as far as I could tell. But, you know, just grew up sort of a normal American life. You know, I had some of the Portland kids stereotypes, like we had chickens growing up for sure, which people always find hilarious after watching Portlandia. And you know, I noticed we had too many chickens for our household, and I would go selling them around the neighborhood, which is sort of like portends what I ended up doing with my life, I guess.

Lee: [00:03:24] Selling chickens from an early age. Very entrepreneurial of you.

Michael: [00:03:27] Selling the eggs. I remember, you know, people would ask me the price and I realized if I didn't tell them the price, they would give me more money for the eggs. And so the eggs were unpriced. I would say, "Whatever you want to give me," and that worked out pretty well.

Lee: [00:03:44] They're like, "Oh, how cute kid. Alright fine. Ten dollars an egg."

Michael: [00:03:48] {laughter} Yeah, yeah, that's exactly right. I didn't have too many customers, but whenever I had extra, whenever the family had extra, I would wash them off and go walking up and down the street we lived on, so I would sell maybe a dozen a week. So it's not some sort of great enterprise or anything. But for I think it was five or six years old at the time, it was quite a lot of money. I could buy myself anything a five year old would want.

Lee: [00:04:15] It's always a good margin as a kid. There's like no cost.

Michael: [00:04:18] Yeah, my parents paid for the feed, but I actually did feed them every morning, which, you know, in the winter in Portland, it's raining and dewey and I had to cross... So probably the actual wage was fairly low, a dollar an hour. So it's not quite that impressive in that context.

Lee: [00:04:39] So did you have any siblings growing up?

Michael: [00:04:42] I actually am a triplet.

Lee: [00:04:44] What? You are a triplet? I think you're the first triplet I've ever met in my life.

Michael: [00:04:48] Most people don't know that.

Lee: [00:04:50] Wow.

Michael: [00:04:51] I think it's one out of a thousand births or something. So it's a little more common than people realize. But yes, yes, I was. I was a triplet, fraternal triplet. We are all very different. In fact, like if you met one of my siblings, you would not even guess that we are related.

Lee: [00:05:12] Yeah, because you always think like, you know, twins and triplets, you're like, Yeah, they all look alike.

Michael: [00:05:19] We definitely do not.

Lee: [00:05:20] So you don't have any stories. I was hoping to get some stories about how you guys like, you know, traded classrooms or girlfriends or whatever. You know, no stories, I guess of that.

Michael: [00:05:29] No, not really. We had different friend groups, very different interests. So the only thing I could share about it is that you always have company when you're a kid your age. And my parents always say that it was sort of like a batch process. So it was a little bit intense for them to do all three at once. But they sort of like they were able to batch all of their sort of like child rearing. And they also had to do like the zero to one thing like times three, which is pretty funny. They would always say, Hey, we didn't have the chance to screw up with the first kid, and now we have to do three at once. But yeah, it was very efficient, I guess.

Lee: [00:06:18] Well, I do not know how they did that. I mean, I just became a mom about three months ago, and it's like with one kid, I can't even imagine having two more at the same exact time. Like you said, going from zero to one, that's pretty insane. Well, and what's it like sharing a birthday with two other people all the time, like every year? You know, it's kind of funny, huh?

Michael: [00:06:36] Really no difference between birthdays and Christmas. That's the best way I describe it. You know, it's like another Christmas. Everybody gets gifts. {laughter}

Lee: [00:06:47] {laughter} Doesn't that happen with everybody's birthday? Everybody gets a gift?

Michael: [00:06:51] Yeah, exactly. It would be almost the same thing. A bunch of family, friends come over. It's like, you know, a group party. I mean, I guess people don't always do that for Christmas, but it was a very similar sort of feel as a kid. But I don't know. I'm not really shedding any tears.

Lee: [00:07:07] So what did you want to be when you grow up? When you were selling these chicken eggs where you like, you know, this is what I want to do? Or what was your dream back then?

Michael: [00:07:15] It's funny. Nobody's asked me that question. I actually wanted to be an inventor.

Lee: [00:07:19] An inventor. That's so specific. What did you want to invent?

Michael: [00:07:21] Which is really funny. Well, my uncle actually invented, you would never expect anybody invented this, but he actually invented the grocery store misting system. You know, when you go to the grocery store?

Lee: [00:07:34] Like in the vegetables?

Michael: [00:07:35] Yeah. And there's like the misters. When he was a teenager, he had a job at a grocery store like hosing down the fruits and vegetables. They used to do it with a hose, I guess. And he thought, you know, there has to be a better way, right? He invented that and sort of ended up having a whole career out of it. And so I was exposed to people being inventors from an early age. But I guess I always thought that that was sort of not plausible. And so I would tell people that and people would laugh. And then I'd say, OK, well, I guess I'll be like a doctor, not a doctor, a lawyer, you know? So that's what I would tell people. But I specifically remember, especially when I was younger, a younger kid telling people I wanted to be an inventor and I had all kinds of crazy inventions schemes when I was a kid. I would build some sort of like half assed like prototype in the garage So that was funny.

Lee: [00:08:32] That's cool. Yeah, I know those misters on the veggie shelves. I think now they even have like thunderstorm sounds. It's like, is that necessary, guys? You know, it always kind of freaks me out like, what's happening? Is there a storm outside? So you thought for a second you would want to be an inventor? What were some of the first jobs that you had, you know, going into college or in high school?

Michael: [00:08:58] Well I started working as early as I possibly could, actually as a teenager, and it's something I'm always proud of and I always look for in people's resumes. I think it's underrated, but yeah, the first job would have to be like, you know, I was a referee at kids soccer games. You know, they would pay like 12 year olds. You could actually work as a 12 year old for that because you were technically a volunteer. So there are some legal loophole. So I would umpire like younger.... I was like a kid, a 12 year old umpiring like five year old baseball games. And then, yeah, as soon as I could get a real job, I got a job as a lifeguard swim instructor.

Lee: [00:09:39] I went that route too. Because you know why? I was like, what's the highest paying gig I can get for my age. And I'm like 14 getting working papers and I'm like, Aha, I can get CPR certified and make like 14 bucks an hour. And all these other kids can babysit for $10. I'm doing this. And I was a swim instructor as well. So how did that go? How long were you doing that and what kind of swim lessons did you do?

Michael: [00:10:02] Oh, I did. Oh man. So yeah, I did that for like five summers almost. By the end, I was sort of like, you know, in three summers, a senior year of high school, I was like the assistant manager of the pool. And then I managed to grab like the coolest job I thought in the whole sort of like parks department available for teenagers, which is something called Lifeguard Auditor. I don't know if you experienced that in wherever you were a lifeguard, but the city of Portland had like five hundred lifeguards in many, many pools. And so they hired a guy or gal to go around and audit all of the lifeguard performance randomly to keep people on their toes. And so that was a great job for a teenager because I was essentially unsupervised and I spent the whole summer driving around in my car, just like popping into pools and scaring people.

Lee: [00:10:54] The Monitor's here. Yeah. {laughter}

Michael: [00:10:55] Well, the funniest part about that actually was you had to record people, like you would record the lifeguards, so you have it on tape and play it back to them and give them a rating, essentially. And that was a very sketchy job because you're essentially hiding around swimming pools with a camera, which would freak out parents. So I had the cops called on me a couple of times and had to explain to them the position, and eventually I had to actually go to this sort of like Park Ranger monthly meeting or something and introduce myself because like a couple of times they came, they didn't believe me at first.

Lee: [00:11:30] The parents thought you were literally... The parents, were like, "There's this guy here who's recording our kids swimming."

Michael: [00:11:35] Yeah, I was just doing my job and like, you know, suddenly there would be like police, like converging from all angles.

Lee: [00:11:42] The creeper at 90 degrees.

Michael: [00:11:44] It's like, "Hey, this is what I do," and I would have to come down and take them down to the pool and the pool people would explain that they knew me. And so that was, yeah, that was like my high school job or like my college summer job. I also did the swim instructor from like the really little kids, like five year olds, all the way up to like the people swimming laps. So that was good. Good sort of first experience with customer service actually too, dealing with the parents of the swimming pool. I'm sure you have some experience with that, but you sort of learn the high variance of people's attitudes in the public service customer service setting, I guess.

Lee: [00:12:29] Yeah. Absolutely. Especially trying to teach the kids how to swim. So what happened after that? So what college did you go to? What did you study?

Michael: [00:12:42] So I went to Oregon State University just sort of just like the normal sort of public university. There's two public universities and two main public universities in Oregon: Oregon and Oregon State. And Oregon State is the more engineering focused one. And I went and studied mechanical engineering for a few years. I actually, in general, I was a terrible student,

Lee: [00:13:09] Really? I feel like you can't be a terrible student if you're in mechanical engineering, right?

Michael: [00:13:15] Yeah, so yeah, that didn't work out. And I ended up transferring to Portland State and getting an economics degree, which was another interest of mine. I really loved the mechanical engineering courses, but they got to be very sort of, I don't know how to put it, like esoteric. So it was sort of got to be wearing on me because it wasn't sort of theoretical. It was more about like, OK, cranking out these detailed problems in exactly the way you're supposed to do it. So I remember I failed some course that was a requirement because it had a very specific like question, and I had been taking a math class that was totally unrelated, and I recognized that the question could be solved with the tactic from the other math class. And so I totally solve this problem in a different way than you're supposed to solve it, and in a way that like I guess if you express this problem with a certain type of formula, you could solve it in one step and that's what I did, and I got the right answer. And basically that was a third of the whole test, and I was given a zero because I didn't show my work, supposedly, and I went in to the professor and explained to them and they said, "No, I don't believe you." That for me was kind of the nail in the coffin. I was like, "Well, I'm not going to take this course again. I'm going to go study economics instead." So got my degree in economics, which I'm happy I did because there were statistical programing courses in economics, which sort of got me into coding to begin with.

Lee: [00:15:01] Hmm. Is that whole situation that happened? Is that why you switch schools?

Michael: [00:15:09] Oregon State is a bit of a party school. I felt it wasn't conducive to my academic success, I guess you can say. And so I transferred to have a bit of a clear start. So yeah, I was not a great student in my late high school and early college time and turned it around by transferring. So that was a tactic that worked.

Lee: [00:15:33] Yeah, changing the environment. That always helps. So you graduated with a degree in economics. It looks like you worked at Nike. What was it like working at Nike?

Michael: [00:15:45] Oh, yeah, so what can I say about that? It was very instructive. It was very interesting to see a large company in the way it worked. I would say that I always wondered how a company could have like thirty thousand employees. That was one mystery to me as like a college student. And so it was interesting to actually see why that is the way it is. And that also sort of it's one of the reasons I left and started a company instead of working there is because the reason they have 30,000 employees is that like they need to have everybody have such a narrow scope of what they're doing in order to make the whole thing function. Because if you're doing something at such scale, you can't screw it up, you need to do it really, really well. And there's so much coordination between so many departments and so many people that it needs to be very clear what your role is specifically. And so I worked there... When I started, I was working in the analytics tagging team, and when I ended, I was working as an A/B testing like JavaScript developer. And it's crazy. My only job was to take the exact specs and implement them into it code for the test. I didn't even know what the results of the test were. I had no say in what we actually did or even what the tests looked like because there is a separate style guide. And it was like perfectly scoped. And so, you know, now I am involved with the A/B testing at Bottomless, and I know what the results are. I can prioritize tickets. I can code out a ticket. The level of scope at a smaller company that you can be involved in is a hundred times wider or something like that. And so I found the sort of more generalist approach of starting a company to be a lot more personally gratifying than the really sort of narrow specialization involved in working at a big company.

Lee: [00:17:55] Yeah. And so how did you get the idea for Bottomless what was that kind of aha moment? How did you go from Nike to building the idea for Bottomless?

Michael: [00:18:04] Yeah. You know, people sometimes assume that my Co-Founder and I are experts in hardware and machine learning and stuff like that. It's definitely not the case. You know, the eCommerce aspect of what I was working on at Nike is somewhat incidental to Bottomless. I can't take full credit for the idea. It was something that my Co-Founder, Liana and I sort of came up with together. It's kind of there were a lot of threads going on at the same time that we sort of tied into Bottomless. But really, the way we came up with the idea was really focusing in on this very specific problem, which was getting stuff restocked in the home. And I had also worked in restaurants in college, and I knew very well how they did the restocking in the restaurants, which is somebody walks around with the clipboard every single day and writes exactly the inventory level. And then they sort of like do the linear math, but the restaurant was always running out of stuff. So it was a poor system because the par levels were not set in any way other than arbitrarily. But anyway, so I sort of had in the back of my mind, OK, well, you know, the way to do restocking properly is actually to know how much you have in a very fine level because I had seen that in restaurants. So I sort of knew that theory. And so we were dealing with this problem of always being out of stuff at home. And there were multiple items that we wanted, not just coffee and we were just thinking, OK, well, how do you actually solve it? It must just be that we don't know how much we have, and there's no system to figure out how much we have all the time. And so that's why these providers can't just ship it to us. We had signed up for a Soylent subscription. And, you know, we had gotten so much Soylent. We canceled, like we had so much Soylent in our tiny, tiny apartment, like four hundred square foot apartment. We had so much Soylent we could have survived an apocalypse. And so we canceled. And then like way later, we ran out. And so [00:20:11] we knew that subscriptions were the best way to solve it and they didn't work. So sort of eventually thought about doing an inventory management system for the home where you're sort of tracking. We thought, no, nobody wants to do that. That kind of sucks. And one day we just thought, OK, well, how do you actually find out how much people have all the time? Just had this epiphany that weight is like a source of truth for how much people have. And if you could just record that in a regular interval, you could actually solve the reordering problem for people. So we decided to make these little smart scale reordering subscriptions and worked our way backwards to coffee specifically because we had a problem with it, honestly. And we knew that coffee was way better if it's sent straight from the roaster than the grocery store. And so it was a bigger like delta, I guess. You know, you could improve people's lives a lot more than just solving the re-ordering problem. You're also providing a higher quality product at the same time. So we thought, OK, well, that's something that could be like ten times better for people. [00:21:18] So long winded answer. But the truth is, that's really it was really sort of a thought experiment. We sat there dwelling on this problem for many months, honestly, just talking about it over and over and over again and going through tons of terrible solutions before eventually landing on this. And we thought maybe it could work.

Lee: [00:21:38] So what were some of the first steps you took to creating this kind of weight inventory management idea that you kind of came up with? What was, OK, we have this idea, now what? Would did you do?

Michael: [00:21:51] Oh boy, I mean, just quit my job and jumped in to do it.

Lee: [00:21:57] Did you really? Just like on a whim? Just quit?

Michael: [00:22:00] Yeah, yeah. I mean, I'd been there for over a year, so I had sort of like accrued the time required for my resume. And I thought, why don't I just give this a shot? I was a self-taught like JavaScript developer, and so I knew I could just figure out technical things by just sort of like looking up examples and stuff. And so I kind of had done a little bit of research beforehand to see some examples on similar things, and I had a sense that it was possible to be done. At the same time, my Co-Founder, Liana, she is the daughter of two sort of entrepreneurs from Peru. And both of her parents were sort of like had multiple businesses throughout her life and like engineering related businesses and stuff. Her dad had done a company where he built busses from scratch, which is insane.

Lee: [00:22:56] Wow.

Michael: [00:22:57] And he's like a PhD engineer. So it's not that far fetched, but still sort of a crazy, crazy thing to take on yourself in the physical world. So she also kind of had... It wasn't beyond the realm of possibility that somebody could just do this sort of crazy quixotic thing and make it happen, right? So she really encouraged it. And I sort of had some youthful hubris because I had made a couple like tiny little products like Chrome extensions and stuff.

Lee: [00:23:29] But what was your plan? I'm sure you had some kind of like idea as to I need to quit so that I can be full time on this because I know if I'm full time in one month, I'll achieve X. In two months, I can achieve Y. What was your kind of game plan?

Michael: [00:23:46] The game plan was to build out the minimum sort of viable product, build out everything required to make it work at a minimal level, like just the total proof of concept and then test if the user retention was significantly better than a consumer subscription, essentially.

Lee: [00:24:04] How did you test that and what was the MVP?

Michael: [00:24:08] Yeah, the MVP was these sort of like development boards that I could buy, like almost like student hardware boards soldered together with like a crazy mess of wires. And then inside a 3D printed plastic that, like now looking back, was like totally a terrible design. They would break pretty regularly. I actually started delivering them myself around Seattle instead of shipping them because they would break in the mail. {laughter}.

Lee: [00:24:42] White glove delivery.

Michael: [00:24:44] Yeah, all kinds of crazy stuff. But honestly, it was this bird's nest of wires in like this big, clunky plastic box. And then like a server that got the data and a little graph where I could see the data myself. And like, [00:24:59] I basically built a prototype eCommerce platform from scratch, like the back end for me to look at it, a front end for the customers to look at, a shop. It was like an insane amount of work, especially for somebody who didn't have experience building hardware servers, really much of any of this stuff, but just really sort of quit my job and got after it. [00:25:23] I think it took something like nine months to get customers on board.

Lee: [00:25:29] Just to build the product out in the way that you would want to build it for real customers? Tell me about actually that phase of when you're sending or driving around to these customers with this like bulky wiring nest of wires. Were you ever afraid that someone's going to steal your idea?

Michael: [00:25:47] Yeah, I mean, I sort of... OK, well, no. Yes and no.

Lee: [00:25:55] And how many people did you drive to like how many people are we talking?

Michael: [00:25:58] So I can say when I quit my job, my boss, who was a very nice guy, I don't want to talk crap about him publicly. He was very great to me when I worked for him and very encouraging of my technical development and let me do all kinds of crazy stuff. Like we built an A/B testing platform from scratch and Nike was great. But at the time when I quit, he sort of said, "OK, well, that sounds good. Why don't you join my friends company that's doing this other thing?" That's how unpromising the idea sounded.

Lee: [00:26:29] {laughter} And so he's like, "Yeah, yeah, sounds cool. When you need a job, let me know. I can hook you up with my other friend."

Michael: [00:26:35] Yeah, or like, "Hey, instead of doing that, why don't you do this?" And, you know, several people suggested that I should just go get another job. So I wasn't really that worried because I didn't think that anybody thought this would be very promising. I only became worried about people copying us once we sort of started getting some press releases and some funding and stuff, because then people have some sort of validation. Because it's such a crazy off-the-wall idea. And over time, I've actually become a little bit less worried about copycats because we've had so many people reach out and say that they tried to do it, but couldn't figure it out. And so I sort of like have shifted my mentality from being not paranoid to very paranoid to not paranoid again. But anyways, like you're asking about the driving around to 10 people, it was like 16 customers that we gave that very, very original prototype to. Actually eventually, it was 60, but we started shipping them after the first, I believe 16. Nothing really to say about it. At the time, we were advertising as a closed beta test. And so we only would allow people to put in their emails because we hadn't built an onboarding flow properly. And so then we would email them and say, "Hey, are you ready to sign up?" And if they said yes, then I would sort of like, create their account and give them a form for them to put in their credit card. They had emailed and then I said, "OK, I'm going to deliver you the scale," and I would just tell them what time I was going to show up and sort of hand it off to them.

Lee: [00:28:09] Were you giving coffee then, as well as part of the deal? Or was it just the scale at the time?

Michael: [00:28:16] Oh no. We always made people pay for the coffee and actually in the beginning, we made people pay more than we even do now because we were very worried about building something that people were only going to use because the coffee was cheaper. In the beginning, we always sort of saw this as a proof of concept for investors, because it's obviously not an idea that you can totally bootstrap yourself to an exit or even to a reasonably sized business because it's very complicated. You're obviously going to need multiple engineers. You're not going to be able to just hack together some prototype and really scale. So we always saw as proof of concept and just sort of like we're trying to get enough of a group of customers to prove that it works better than a subscription. And so that's actually an interesting part of the story is we got these 16 customers on. We sort of like worked to build everything required because we built it, we got them on and then we realized, oh holy crap, we need this thing, we need this thing, and we need this thing. And so sort of just sort of scramble to build this stuff that we needed to just do even the minimal product with them. And then after about maybe six months had passed or something, we finally had the data that these people were ordering way more coffee than they would have on a coffee subscription. And I got some sort of comparison data on what that looked like, what a normal subscription looked like...

Lee: [00:29:39] What is the data? Can you share with the data is?

Michael: [00:29:44] I don't know if I can. I just think we've shared this publicly.

Lee: [00:29:48] Or in general, I guess, like even just subscription and maybe like the difference. You don't have to give exact numbers, but just to give us an idea.

Michael: [00:29:56] So one thing I can say is that subscriptions continually churn people. If you're down to like, maybe I think the best subscriptions might retain 30 to 40 percent of their revenue like a year, but then they continue to lose forever. And what we've been able to do is not only beat that like 30 percent quite a bit, but we also essentially just stay flat basically through year one, year two, year three. So that's sort of like the primary value prop, at least to investors specifically, is that we found out a way to just sort of satisfy people's demand in the long run. And the thesis is basically subscriptions are great, people like getting things through the mail, but after the second, third, fourth, fifth time of managing the timing, people are just going to cancel because it's just not worth the hassle. And even if you do drink coffee weekly or every two weeks or every four weeks, you're going to drift off eventually. And I've run simulations that show basically like the minimal amount of time that you're going to have to manage your subscription is like three times a year or something like that. So there's just a constant opportunity to churn. And for us, all people need to do is recharge the scale once a year, and we have to do a minimally good job of sending them coffee. So maybe there's like a couple adjustments in the beginning to make sure the scale is set up right to sort of like maybe adjust their coffee selections, rate a few coffees, but then once you're sort of used to the system and it's all going smooth, there's really no reason to churn.

Lee: [00:31:35] The timing really is inaccurate. It's not accurate at all for subscriptions. I mean, we deal with that all the time here with my husband and I with protein powder. It's just like we'll have like four cans of it or containers of it. And then sometimes we just don't have any and we're like, "Wait a minute, where'd it go? I thought we had a subscription. No, we canceled it because we had four. But where they'll go?"

Michael: [00:31:55] Exactly.

Lee: [00:31:55] You know, it's like this constant thing of on and off, on and off, with subscriptions. So that's super interesting. And obviously, you sent me a scale which has been really cool and actually really easy to set up. It's like, you know, you just plug it in and you charge it, you push the little button, it turns green and then you go through this kind of like really easy setup process over Wi-Fi. It's so interesting. Now I can see the data on my phone of when I can expect to get some more coffee as I'm kind of drinking it every day. Or even it's uneven. Sometimes I'll make two cups, sometimes only one. So I'm one of those, you know, chaotic drinkers of coffee. So it's cool to have something that's kind of tracking that chaos and keeping me on my feet of when to... I don't even have to do anything. I'm just going to get a text message right of like, "OK, you need to order your coffee now. What do you want?"

Michael: [00:32:49] Yeah, and it's dynamic. So [00:32:51] we actually are looking at your patterns and sort of dynamically figuring out essentially when should we order, so the likelihood of you running out is fairly low, [00:33:00] but not too low, because then we'll be ordering crazy early, right? And we're constantly sort of like modeling... We actually model. This is a crazy thing that we do, but we actually look at how long it would take if we ordered from basically any of our like 70 roasters to get to you. And we look at that like every day and try to decide like, OK, what's the best roaster to send to you? And then for this person for that roaster, what's the timeline look like? And then, OK, do we need an order based off that? So there's a lot of magic.

Lee: [00:33:31] Yeah. And how do you choose or match me to the next coffee? Because here I'm, you know, I got this really great Brazilian coffee that was really good. It's kind of chocolaty and nutty, whatever. But how do I know or how do you know what to send me next?

Michael: [00:33:46] So we allow people when they sign up to basically specify what types of coffee that they like, so we have like a custom rotation filter. We eventually landed on that over time contact with customers. In the beginning, we just had people sign up for one type of coffee and then they would just get that over and over. And we just found... So like the way that the ordering system works is exactly what we thought and anticipated going into doing this company. But [00:34:12] the way that the actual coffee product works has evolved with contact with customers over the years, [00:34:17] which is kind of another interesting thing. But now what we've landed on is when you sign up, you tell us if like dark roast, medium roast, light roast, espresso? Do you want to pay like a premium price? Do you want premium coffee or sort of basic coffee? Do you want ground coffee? And then how much do you drink? So we match you to like a size that's going to be appropriate? And then we just sort of like, build it. We have like this filter for your account, and then we do a bunch of essentially math every day to figure out, OK, you know, what does somebody with this profile tend to like? And then we combine that with the arrival timeline data and decide what we should order for you. So if you're in Florida, we may consider the rosters that we have in Georgia, Arkansas a little bit more strongly than our roasters in California. And so we do like this really, we combine like a ton of different data points to figure out what to send to you.

Lee: [00:35:24] Nice.

Michael: [00:35:24] And then it goes even deeper. You can sort of pick more complicated filters so you can say, "I want nutty type of coffee," or fruity types with fruity tasting notes. You can pick like the roaster, specifically, the origin. So we have like a super advanced filtering system. You can build basically any type of rotation that you want. I don't think we do a great job of marketing that, to be honest, but it's definitely...

Lee: [00:35:45] Yeah. I actually didn't even know it goes that deep. That's pretty cool. So tell us about YCombinator. How did that come about and when did you guys apply?

Michael: [00:35:55] Well, the interesting thing is we applied three times.

Lee: [00:35:59] Really?

Michael: [00:35:59] Yeah. And we put a ton of effort in the first time and just didn't hear anything. The second time, we put a decent amount of effort and we heard back, but then were sort of rejected. We didn't get an interview. And the third time we just like realized the day of the application deadline that it had to be done after it had expired, I think. And I sat down for half an hour and just banged out an application just sort of like stream of consciousness, and we got an interview.

Lee: [00:36:31] {laughter} Of course.

Michael: [00:36:33] I think the reason was YC sees lot of people that are just trying to... They do something... And I talked to a lot of people who say, "Hey, we quit our jobs. We worked for four months. We applied to YC, we didn't get in, so we quit. And now we're looking for something else to do." I've heard that story a dozen times, and [00:36:51] what they've noticed correlates really well with success is people that have a very specific thing they're working on and they make progress every time and they're still working at it. And so when we first applied, we had like 16 customers, and by the time we applied the third time we had like 150. And so they saw that we were still just grinding away on this and they saw our sort of traction. And so trying to impress them with a bunch of clever writing is not as impressive as sticking to something and just sort of making progress on it over the long run because then they know you really, really are serious about building a company around this. [00:37:31]

Lee: [00:37:31] Right. It's consistency, and they're like, "Oh, this person's not giving up. Maybe we should really take a closer look at this."

Michael: [00:37:38] Yeah. And we really believed in what we were doing because we saw the early data, and we sort of knew... We believed in a way earlier than investors did. With that first cohort of 16 we saw that the reorders were just coming, and we knew that the hardware we were using was really janky. It would break and we'd have to replace it all the time. And so like, we knew that it worked and we really believed in it. So we really stuck with it for a long period of time. And yeah, we got into YC, we flew down to San Francisco. We did the whole program and that was a pretty good boost to the company. It gives you a pretty good amount of credential, to be perfectly honest, and I definitely subscribe to a lot of the YC wisdom as well. I remember when I went down there, I was somewhat skeptical. After leaving...

Lee: [00:38:31] Really?

Michael: [00:38:32] Yeah, that's just my personality. I was like, yeah, sure, whatever. But by the end...

Lee: [00:38:37] Whatever. You're just the top accelerator in the US. It's fine. It's not a big deal. Might be a scam.

Michael: [00:38:46] Well, there's a sort of certain aspect of the rich get richer. If you only accept two percent of companies, it almost doesn't matter. You're going to get these great companies as long as you don't do a terrible job of picking. But after going through the program, I became sort of convinced that they really know what they're doing in terms of their sort of mentalities that they've learned after working with a lot of companies. For example, you asked me, "Did you guys have a plan for like month one, month two, month three, month six?" And I kind of dodged it because to be perfectly honest, I didn't really have a plan. The plan was, I'm going to build this thing. When it's ready, I'm going to get customers, and then I'm going to try to get more customers. And you know, the funny thing is in YC we saw these hyper credentialed people really sort of like straight edge 4.0 from Stanford and Harvard and MIT type of people. And they in the beginning of the program, all had plans for like four month plan, exactly what they were going to do. Week one, week two, all the way through week 15 or whatever. And you know, the partners at YC sort of, I don't want to say beat it out of them because that sounds too negative. But they would just ask, "OK, did you grow last week, right?" They would go around the circle of our little groups and say, "OK, how much did you grow last week?" And they would say, "Oh, well, this week we're doing market research," and the partners would say, "Yeah, no market research. Try to grow. What do you have to do to grow?" "Well, our products is not finished." "Ok. Finish your product. What's the fastest you can finish something that's valuable for customers." "Ok, we can do this. We can hack this in two weeks." "Ok, come back in two weeks." It's done. Ok. "How are we going to get customers?" "Oh, well, we're going to go do this and that..." "No, OK, just try to get customers like this week. How many customers can you get this week?" And [00:40:33] it was always just focusing on the problem in front of you and just trying to continually grow. And so that was a very valuable thing, and I saw people sort of transform their way of doing things from sort of a very sort of business plan, sort of what I might call pseudo entrepreneurial mindset to a very sort of like hustle oriented mindset. [00:40:58] So that was pretty cool, and I saw a lot of people make a lot of progress with that mentality.

Lee: [00:41:04] That's really interesting. Yeah, I mean, I think a lot of Founders, first time Founders, you just don't know what to do first. You know, you're just like, "Where do I start? Oh, we'll do market research now. We'll do this and we'll do the pitch deck," and you're like, "No, actually, you just get to work. You actually just need to get customers in revenue like asap." So what's the quickest route to that?

Michael: [00:41:22]  [00:41:22]Make something, try to get people on it. If they don't want it, ask why and make something else. And then once you have people, try to grow it. If you can't grow, it solves a problem. I [00:41:31]t's just so simple.

Lee: [00:41:34] And it really just takes some hyper focus on that, on that one important thing, you know, versus all the other distractions. Like, maybe we should do a podcast. Maybe we should do this over here. Or like, yes, it can be very distracting because there's so many things, especially as an entrepreneur, that you want to do and tackle But yeah, especially in the super early, early days, in order to move super fast, you've got to have a lot of focus on the right things. So you just raised a Series A 4.5 million dollars round. In total, you've raised 6.5 Million dollars. What was that like? What were some of the challenges that you faced in fundraising?

Michael: [00:42:21] So the first time I tried to raise money, I completely failed.

Lee: [00:42:25] How and why?

Michael: [00:42:26] Total failure. So I alluded to it earlier that I believed, and we believed, Liana and I, in the concept way earlier than investors did. And so we sort of like we worked like crazy and really ground. We were bootstrapping and we got these 16 customers on board and we had acquired them using like simple online ads. They weren't our friends, and we saw people actually using it. And so we really believed in it at that point. And so I just went out and tried to raise money, and it was a complete, abject, abject failure. Like no investors were even close to interested.

Lee: [00:43:05] They weren't interested in your 16 customers?

Michael: [00:43:08] {laughter} Yeah, it's so funny in retrospect. But at the time, like, I really felt like we had proved something minimally and we weren't trying to raise a lot of money. We were trying to raise like a hundred grand or some tiny little pre seed just to, like, continue to acquire some more customers. It just was not compelling, and that was something that I really learned. For other people that are interested in raising money, you have to prove it. Really, it's almost like it's cliche, but you have to prove it beyond a reasonable doubt. You have to actually have something that people are... Because naturally, they're going to doubt you. You're just like some random person trying to ask them for money. And unless you have like an incredible track record, people get blown off course because they read TechCrunch too much or whatever. And they just assume, "Oh, all these people are coming out and raising five million." And it's like, no, you have to look at either what they've accomplished so far or who they are. [00:44:08] If you're an early employee at a company that has gone nuts and IPOd, or  you're a previous Founder that has found some success, like, yeah, sure, you can start something and just get funding right off the bat. But generally, the other people have really done a lot of work to prove what they're doing to get that sort of fundraising, even today in this fundraising environment. [00:44:29] And so I actually had not internalized that. Perhaps I had read too much startup news. {laughter} And, you know, I thought it was just a done deal. You know, we were doing this sort of innovative thing, and it could obviously be the future. It's obviously generalizable. We had proven it. We had proven that we could do it ourselves, and I was really bullish and it was a complete, abject failure at the time. And I remember Liana and I sort of like went on a long walk and we talked about it and we almost shut the company down and we just said, You know what? We really believe in this. We're just going to keep going. And so we actually just kept working at it and kept growing and kept getting more customers. And eventually that proved to like an early pre seed investors that, hey, these people are legit because we had grown considerably from the 16 customers by the time we raised money. So yeah, what I learned is you really have to prove it. You have to prove it beyond what you would need to prove to yourself. And I don't know what else. I mean, that was to get the pre seed.

Lee: [00:45:36] What's the difference between the KPIs that you need for your seed round versus a Series A? What do you think is the biggest difference there in those types of investors? What are they looking for in those two different rounds?

Michael: [00:45:48] The pre seed, a lot of it is really just betting on you, even though you have numbers, but the resume is what you've done. And so 16 customers could just be fake, basically. You know, it wasn't, but that's what's going through their minds. But in the beginning, you really have to just show that you can do something impressive and that what you're working on is good in theory to get like a pre seed round. To get a series A, you have to actually show real traction, real numbers. You're going to have to dump all of your data and send it to investors, and they're going to actually do their own independent analysis. They need to see like a critical mass. And again, this may not be true. There's multiple things that they're winning at the same time. Like who you are. I had no track record. So for me, I really had to prove to a very considerable degree what we were doing in order to raise it.

Lee: [00:46:44] And what were some of the questions that you would ask investors to see if they were the right fit for you? Or how did you go about vetting investors?

Michael: [00:46:56] You know, to a certain extent, investors really self-selected themselves for us. I would have investor meetings where people would be like, "Oh, where did you go to school and what's your background?" As their first question. And I would tell them, and then they would immediately lose interest.

Lee: [00:47:10] They're like, "Did you say Stanford? No. Oh, OK."

Michael: [00:47:13] Portland State. I've never heard of Portland State. And so there wasn't really too much, to be perfectly honest, that I needed to do to screen out investors because the people who were the type of people that I wouldn't want to work with generally screened themselves out very early on, and the people that would sort of give you the benefit of the doubt talk through things with you and sort of really independently analyze whether you are a determined person and an independent thinker or whatever is necessary. They sort of selected themselves. And so there wasn't a lot of screening. I would say, like most of our investors have come through sort of like... I mean, another part of the fundraising story is that I had an anonymous Twitter account that became very popular within Silicon Valley. And so a lot of the very pre seed investors were people that I approached through that account or like introductions through that account.

Lee: [00:48:08] Like, what do you mean? You were like pretending to be someone else because it's an anonymous Twitter account. I wish you could tell us what it is, but you can't.

Michael: [00:48:16] I can't. I can't say the account. Although people some people know at this point. But if you're involved in sort of like Silicon Valley Twitter, you'll see that maybe a third of the accounts are not directly tied to anyone's public identity. And so I sort of had started doing that for years and not really purposefully, but just as a way to get out thoughts that I had. I found it very almost productive because I felt like I had done something with my thoughts.

Lee: [00:48:45] What kind of thoughts were you sharing? What was the purpose? What was the purpose of this anonymous Twitter?

Michael: [00:48:50] There was no purpose. There was no purpose.

Lee: [00:48:52] You just wanted to have a voice.

Michael: [00:48:53] Life philosophies. Business tech. Just like you name it. But I just happen to be interested in tech and startups, obviously. And so the sort of audience that I built and the network, the friends that I ended up making on the app ended up sort of aligning with what I was trying to do. And so that's sort of, you know, I make it sound like...

Lee: [00:49:18] What did you say? Were you like, "Hey, so I actually have a startup company and my name is actually such and such..." And you know, like, how did you approach these people you had built this kind of like virtual relationship with online on Twitter and then bring them into like, "Oh, actually, I'm a real person and I have this company. Do you want to invest?"

Michael: [00:49:39] Yeah. Well, I mean, what people don't appreciate is that if you are regularly posting and people are regular users of an app you are like as important as like, you know, CNN or like, I don't know, Elon Musk or whatever like. Not quite Elon Musk, because he's very famous, but like you as a source of information, you as an entity to these very specific group of people is somebody with a lot of credibility. If they see things that they think are insightful over and over and over again, they really, really know you and they really know your thought process.

Lee: [00:50:17] And you're following on Twitter? You're like a Twitter influencer. How big did the following get?

Michael: [00:50:22] Oh man, let's just say between 10 and 100 thousand. I think that's a wide enough range.

Lee: [00:50:29] {laughter} Yeah, thanks. That's really wide. {laughter}

Michael: [00:50:32] I mean, it was not very hard to just say... What I did honestly was I found people and I said, "Hey, I'm going to be going to San Francisco. Can I meet you?" And it was just friends that weren't necessarily investors, and I told them what I was doing. And they would introduce me to people. And so I went three times, I think, where I would go and meet a bunch of people. And then I would say, "I'll be back in like three weeks," and then I would handle all sort of like the follow up intros and follow up meetings and stuff and line them up for another trip and then go again later, and then by the third time it was done.

Lee: [00:51:12] How many people converted? Did you find investors that way?

Michael: [00:51:17] Yeah.

Lee: [00:51:17] So what was the conversion rate on investors? I feel like people are going to start anonymous Twitter accounts right now and like, try to, like, create a following and get into the Silicon Valley and then try to fundraise this way. It's really interesting.

Michael: [00:51:29] What I can say is I didn't do it on purpose. So I very much was doing it authentically as just a creative outlet. And I think that if I would have done it on purpose... I now have like a real name Twitter account and it only has like, I mean, I want to say only, but there's like I have like 3000 followers. And I try to make it like an interesting Silicon Valley person Twitter account and mostly just fail at it. So there's something interesting about doing it as an authentic sort of creative pursuit, rather than with any sort of aims. But yeah, I mean... Yeah, I don't recommend... I mean, I do recommend doing it, actually, and you just have to make sure you're tweeting about things that you legitimately think are interesting and trying to build like authentic relationships with people. Because I would say the people that I originally connected with online when I had like one hundred, a thousand followers were not the same as the people who eventually invested. So it's not like I was going to like the best known investors and trying to make friends with them, because that happens all the time for these people.

Lee: [00:52:31] Tell us about one of the most challenging moments you've had in building the business and how did you overcome it?

Michael: [00:52:37] Well, definitely that first attempt to fundraise, that was a total failure. I think that was extremely hard because I had put a lot of work into the business and so had my partner. We had really poured a lot into it and we were bootstrapping it, and it took a very long time to actually build out the first version. As you can imagine, I mean, it's a fairly complicated thing and and we just didn't believe you could do it with anything less than a full prototype everything. And yeah, that was really just heart wrenching, almost just gave up because it just seems like the ROI was very low. I had gotten a job as a software developer and I could have gotten another job and really build my career, and that was a much more sort of like obviously lucrative thing at the time to be doing with my time. And also, it's not very status enhancing to be bootstrapping a company with no funding for over a year at the time. People generally just see you as an unemployed person and don't really believe what you're doing. So I would have to say, that was definitely the hardest moment. And we just stuck with our guns. We just stuck with our guns. We just kept working at it because we just believed in it based off the results. And honestly, eventually tapped into my network because before I had stubbornly refused to do that because I wanted to remain anonymous. So sort of like, giving up on some of your ideals, I guess. Selling yourself out a little bit.

Lee: [00:54:14] So I was reading an article, I think it was from GeekWire or something like that, and it said that you guys are a husband and wife team. What's it like working with your spouse and how do you guys find balance?

Michael: [00:54:26] We don't. We don't find balance. I would say, we really just are all in on what we're doing. And to be perfectly honest, it's a great advantage. Doing startups is a lot harder than people think, unless you do something where you just strike gold and it just explodes, which is the case for some successes. But for many others, it really is a grind. And [00:54:50] in particular with the type of company that we're doing that's really sort of building something novel from scratch and having to do a lot of new things, it just requires a lot of focus. We have to be three times smarter and also work three times harder. And I think having your Co-Founder also be your spouse is a massive advantage [00:55:14] because we don't have to... What can I say? You know, in a typical work environment like you have to squeeze out all of your like your brainstorming before, like Friday at 7pm or whenever you might end. But for us, like we really have a lot of time to sort of brainstorm and to sort of think through what we're doing. And we both are very passionate about what we're doing. So there's really no conflict about not talking about the company during certain times. It's very much a passion for both of us. So it's honestly great. I would recommend it. I would recommend it to anyone if they are actually sincerely interested in doing something wholeheartedly, which is not the case for certain types of occupations, but for entrepreneurship, it's great.

Lee: [00:56:07] Yes. Yeah, and so what do you think is the biggest thing you've learned about becoming a Founder/CEO? Or even just being a leader, leading a team. What are some of the things that you've learned?

Michael: [00:56:20] That's an interesting question. There's a lot of threads to pull on. In terms of leading a team or leading a company, one thing that we've discovered is the value of processes. And so we're almost reinventing the wheel. But when you're a young startup and you start hiring people to help you, it's not very natural to put processes in place.

Lee: [00:56:40] Right.

Michael: [00:56:41] And so for our operating rhythm of the company, we have a very specific process that's essentially a checklist where we just go through a checklist every day to make sure all of the core essential functions have been done and sort of flag any problems with those core essential functions. And so that is actually an incredibly useful thing. And likewise, for hiring, we used to just sort of like put out a wreck and just sort of chaotically run through the people and eventually say, OK, we like this person and hire them. To be perfectly honest, we made a lot of hiring mistakes in the beginning of the company after we had initially raised money and were trying to build out our initial team. And, you know, now we seem to be doing a much better job at that, and it's because we have a very specific process and a series of filters that we run people through that we think about deeply beforehand, and then we just execute it, so it works.

Lee: [00:57:39] What does your hiring process kind of look like? You know, what is your framework for that? Because I do agree. I think a lot of early stage companies they just put up a job post and meet with a bunch of people. And hey, you sound great. Let's go. So what's your process?

Speaker3: [00:57:54] I mean, the hidden secret about a lot of startups is kind of a shit show. And that's one way to create a shit show is to do that. What can I say about our process? I mean, we have a series of filters sort of like screeners. And it's different for every role, and we sort of tune the screener based off the results. So, you know, if we think, oh, this person was a great hire, we might look back and see what they did on certain screener things. And they're more automatic for us in the beginning, and they become more and more manual to the point where it's actually an interview in the end. But we have like a system of actually rating interviews as well. Yeah, I would just say a series, you know, if you have like a hundred applicants, maybe you find a screener that's going to cut out half of them and then half of them and then half of them. And you can do three of those and you just have to consider what that screener looks like at every step to sort of most efficiently and with high fidelity screen people out. Or I guess, screen people in is a more positive way of saying it.

Lee: [00:59:08] Right. And with ratings, what are you rating people on? How does that work?

Michael: [00:59:16] Well, what you want to do is you want to avoid rating people on whether you like them. I mean, you do want to. You do want to like the people that you're working with ultimately. But if you're doing a screener, and you're trying to screen quite a few people and qualified people, the easiest thing is just to rate people on whether you sort of like personally enjoy them. And I don't think that's the best way to find people to hire. So you want to have like a system like a rubric or you're trying to rate them on specific job related skills. Or like another thing that I do is I'll have a standard set of questions that I'll ask people in an interview that I will sort of like I have asked like 50 engineers the same question. And so now I know very well what is a competent answer and what it's not and what is sort of like a mind blowing answer. And what it looks like when people are sort of BS-ing. And so it helps. That's another sort of systematic approach. It's just you have two or three questions that you ask every time. And outside of that, you can have sort of a free flowing conversation, but make sure you get to those and you rate people specifically on their answers to those questions instead of just rating them at the end, which is always just going to be a proxy for whether you like them, whether you sort of are honest with yourself or not. That's just what it's going to be.

Lee: [01:00:38] Yeah. And you know, before we wrap up here, what is next for Bottomless? What do you guys kind of... What's the big grand vision?

Michael: [01:00:48] You know, the way I described how we came up with the idea originally sort of can sort of predict the answer that I'm going to give now, which is we came up with this very independently of coffee subscription specifically. We really conceived this originally as a solution to the restocking problem broadly. We see ourselves really starting with coffee subscriptions and then finding ways to service our customers with other types of products. And there are several. And so right now, our sort of North Star is eventually to build out an eCommerce marketplace of sort of like direct to consumer type products that you want to get shipped straight from the producer. Obviously, that's sort of far off from coffee. And right now we're just trying to make the best coffee subscription in the world. But you can imagine there's many other types of subscriptions that we can move into. And then more broadly, in the far future, I feel like [01:01:49] our real goal is to figure out how to automatically replenish everything intelligently using sort of like sensors rather than people having to do it manually and try to store this information in their head. It's just the way that restocking is done broadly is broken and it's broken in commercial settings, it's broken households, and it's even broken into some industrial settings. It's just a matter of whether you can perfectly count in some external way that doesn't involve like sensors or of some sort, which is generally not the case. [01:02:28] So we really have a crazy broad vision for what we want to do in the long run. And you know, that's another challenge with the business, honestly, since you asked. Staying focused on making the best coffee subscription and putting one foot in front of us at a time.

Lee: [01:02:46] Yeah, absolutely. And you know, I guess along those lines, what's some final advice you have for aspiring entrepreneurs tuning in or business operators? What would you say to them? Quit your job right now?

Michael: [01:03:00] Well. Hmm. You have to be honest with yourself. One of the experiences of doing what I see was just seeing that it's not for everyone. And so it really depends on do you like operating in extreme uncertainty and trying to deliver on something that you have absolutely no experience? And, you know, also having the right partner to do it with. Sometimes people succeed as a solo entrepreneur, but I certainly wouldn't have. I'm kind of the sort of like head in the clouds, I guess, back to what I wanted to do when I grow up adventure type. And my Co-Founder is a very focused, sort of results oriented business woman, I would say. But if you have the right team and you are interested in this lifestyle, which is also insane, you know, basically all I do is Bottomless. I eat, breathe and sleep Bottomless. Then sure, quit your job. If you want to go down that path, I would say I very much enjoy it. I love my life like this, and [01:04:11] I find it immensely gratifying to work very hard on something that I think is ultimately going to be very impactful for the world. It may sound crazy, but I legitimately think we're going to inspire a whole new type of technology. [01:04:24] You know, whether it's us making it or not, people are going to eventually get so used to getting things restocked automatically like this that it'll just be a natural to apply it and everything.

Lee: [01:04:36] That's really cool.

Michael: [01:04:39] Yeah. My advice would be to go for it if you want it. Don't expect it to be status enhancing in the short run. You have to be prepared for a long slog through the wilderness before people actually want to interview you or whatever.

Lee: [01:05:02] Well, thank you so much, Michael, for sharing your vision and advice you have around entrepreneurship. It was really fun hearing your story. Thanks so much for being on the show today.

Michael: [01:05:12] Yeah, thanks for having me. This was really fun.

Lee: [01:05:17] Thank you so much for listening to the Stairway to CEO podcast. Once again, I'm your host, Lee Greene, and if you have any burning business questions, please feel free to reach us at StairwaytoCEO.com. We'd love to hear from you. And if you like what you hear be sure to subscribe to the show, tell your friends, leave us a review, and follow us on Instagram @StairwaytoCEO. Until next time, guys, keep on climbing.

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