Michael Mignano on selling Anchor to Spotify, investing in xAI, and co-founding OBO — an AI learning platform

we don't have you up on hit it a little harder hit the gong little harder a little harder all right there we go that works can you guys hear me right every time broke it that was that's what I was going for I was hoping we would break it welcome to the show uh what's going on uh you made it to Boston he uh Michael messaged me like maybe two hours ago and says I might uh be in the air but you made it and you're at uh where are you right now so this is Theo Studio cool very cool um this is where I guess they have like artists roll through and stuff when they're in town nice yeah is Boston a major is Boston a major music Market or is it more so they're bringing in musicians that are helping improve the models that they're making and the app in general I I think it is market right it is a it is a major Market but no it's not like in LA or in New York but this is where sun was founded right uh the founders came out of MIT Harvard there's obviously as you guys know there's a lot of machine learning research going on in Boston and Cambridge so that's where the company got started but you know I think what they had a really smart idea which was when our artists start going through Boston which you know most major artists do that can use this studio it's a place to Qui can you introduce yourself stre yeah yeah yeah and give us back your man the man who needs no introduction but you may as well do it but you're not at that level yet of course of course no I mean I I appreciate you guys bringing me out sorry I introducing myself yes yes yes introduce yourself tell us what you do now and then I I have a bunch of questions about your career we we'll dive into all right let's do it uh what's up everyone uh my name is Michael mcnano I'm a partner at light speed uh I was the co-founder of anchor podcasting platform now Spotify I also recently co-founded a company called OBO which is an AI education platform awesome yeah big big fan of the Pod happy to be uh one of the early guests thanks for I'm a huge fan of anchor I we we I used it for some podcast test I did like must have been right when it came out and I just remember thinking like man this is this takes so much of the headache out of podcasting you just you could upload it on your phone I I don't think was the original Vision uh you wanted people to be producing and and producing podcasts on their phone and uploading because that was a button you could just kind of hit record and then boom it goes out to the RSS feed but it seemed like it almost became like a prosumer tool pretty quickly because the podcasting Market it's pretty bifurcated between like people start taking it seriously once they get any sort of traction right yeah no the the original vision for anchor actually was not to be a podcast platform it was it was very very idealistic we wanted to be a social media platform like audio social media yep like think Clubhouse but a couple years earlier sure and what we what we learned is that social audio is really really freaking hard yeah um you know we we we took a crack at a certain format uh take on it that we had which did like fairly well I mean there was like you know there were spikes of growth here and there but overall wasn't working after a year we like completely pivoted to another iteration of social audio gave that a year didn't work and then what we were hearing from all of our users is hey we just want to use these tools to publish podcasts to Apple and Spotify yeah and when we did that it was just like instant pmf from that moment so yeah take us through the story of the of the company how big did you get you raised money I'm sure eventually exit I want to hear that yeah yeah and for for a little little bit of lore uh when I was this was 2018 I just maybe I was still in college I hit up Michael and he did a call with me uh didn't need to had no real re I mean it was much more beneficial for me I was doing I was and you know doing a bunch of podcast advertising stuff at the time but uh thank you thank you to Michael you always remember the people that like give you you know 30 minutes of their day uh however long it takes but uh but yeah I would love to hear the the the story again yeah I so so so my co-founder and I uh near zerman we we built product at this company called Aviary and this was around the time that um like Instagram was taking off and people were realizing that you could take and edit photos on your phone and actually look good obviously you know now that's that's just a given like the camera is the phone and you know we sold that that business to Adobe and while we were there we got really into podcasts yeah and we we were sort of like sitting around asking ourselves like how come nobody has done for photos uh how come nobody's done for podcast what has just been done for photos and so that was like the original idea like and of course at this time it was like 2016 everything was a social network back then like Snap was exploding and we're like oh of course this should be a social network right we should have a feed we should have a button right at the bottom of the app in the middle and and and so that was the original Vision we raised a couple million bucks for folks like uh beta works and SV Angel and eniac and all these all these guys and um and yeah like I said we you know we we we had to go through a couple of different pivots we raised I think to answer your question John we ended up raising just under 15 million total sure uh we were about 25 people when we exited we sold to Spotify in 2019 actually two Acquisitions on the same day anchor and gimlet I remember that yeah I remember that which is like the cardinal sin of of launches is like if you have two very interesting launches you should just do them like space them out like you know get the full benefit of each but uh I think I I I mean you can probably speak to it more than I can but it seemed like Spotify really wanted to plant the flag and be like we are in podcasting now so not just one acquisition we're taking this seriously uh wait quick question did you ever run into Archie archibong at Avary yeah of course I hope he's listening this clip that's awesome yeah yeah he was out in Japan a bunch uh yeah good guy big in Japan huge in Japan honestly uh I wanted to ask you about uh where you know as somebody who sold your company to Spotify worked there for a while and then now you have a much more sort of uh now you're venture capitalist um I'm C but but still you know I'm sure very opinionated on the Spotify product how do you you know where where do you think Spotify is going you know we we we had talked about this a little bit offline I'd said uh and I had even posted about this of spotify and YouTube have sort of always been on a Collision Course Long Ultra long form became very important to YouTube and then they became the biggest podcast platform uh and in many ways like podcasts aren't just replacing radio they're replacing TV yeah right which is so it's super important to YouTube uh and it it feels like a sort of critical Battleground for Spotify but I'd be curious to get kind of your point of view on the on the overall uh battle between these you know tech tech Giants right Spotify feels like a small company but it's $140 billion market cap it's a big business probably would be well beyond that if Apple music uh wasn't you know rammed down everybody's throat but uh yeah love would love to get like a kind of General market perspective on on that yeah so taking a step back and I should caveat all this by saying that I haven't been at the company in like three years so this is this is a pure Outsider perspective um but you know I think the big thing that Spotify has always done well and they've always believed in is this notion of bundling right like taking taking these products and these business lines that they have strengths in and then bundling them with other new new products product lines and product and business lines and that's honestly why podcasts were so successful for Spotify you know if you think back back in the day when it was like Spotify head-to-head with apple apple had two separate apps for these things right they had music and they had podcast two separate apps and that was a that was a total gift to Spotify yeah because Spotify could take the podcasts and put them right next to the music so you never had to leave the experience and that's really what kickstarted the whole thing it's like they had a built-in audience of hundreds of millions of people that were One Tap Away from podcasts and I think you know maybe to start getting to the the question you're asking I think that's that's how they've probably thought about video as well it's like hey we have people listening to music now we have them listening to podcasts what if we bundle in video now and that opens up a whole new market for us so the obvious place for them to start was with podcasts right like they have every podcast in the world already now let's get these people to add videos to these podcasts but you know again as an outsider you have to imagine the next step is you start to see other types video content on the platform and even if they can start chipping away a few market share percentage points here in there YouTube's catalog that's a big deal for Spotify so um I think it's I think it's a pretty smart how do you think about the Relentless March of the algorithmically curated feeds uh in the podcasting world I think a lot of podcasters are super super happy that they're in the RSS feeds and they feel like it's almost as strong as having someone's email address there's a very high open rate if you have that RSS feed you're a weekly show you're dropping a weekly thing right at the top of their apple podcast app but and Spotify has a similar feel right now but you could imagine them going to something that that's more algorithmically generated more variance in the in the total views you see this on YouTube where uh you know Mr Beast can be can be reliable but for most other creators it's like a banger and then a flop and then a banger and then a flop and we all feel this on X when we post um you know it's very high variance but you can go really really big because it's an algorithmic feed uh you know your your podcaster who's built on RSS pretty hard to all of a sudden have one episode go 10x bigger but the downside is very protected uh do you think my my question is basically like if I'm an RSS podcaster and I'm thinking hey I want to go to Spotify this a little dangerous because I could see them going more algo feed in the future and then that introduces more volatility to my business maybe that's good maybe that's bad what's your read on that yeah yeah I mean I think the RSS feed is a very very controversial thing in podcast land you have the podcast purists yep that will live and die by the RSS feed I mean they will fight you to the death if you tell them that RSS is going to go away y um but but on flip side like it has lots of limitations the RSS feed like it's there it's not like a two-way channel right it's like very limited in terms of the functionality it can ultimately provide and you know I think there's probably no coincidence two biggest platforms now for podcast Spotify and YouTube are not really RSS based anymore right they're they're all doing things that layer on top of the format that have nothing to do with RSS and so again I know like the RSS purists are you know probably want to want to murder me right now but I just don't I I don't know if the the format uh is is viable long term as a solution I think because like you said you can you can get massive massive Distribution on YouTube that you can't get through just like a plain old rssp totally yeah the the two things as a Creator now uh the analytics on the RSS feed are just obviously a joke you basically get no analytics and then with Spotify is a lot better but then the the distribution which we're already seeing this with Spotify um you know we're we're we're growing our audience just by nature of being on Spotify versus like that's not really happening on Apple it's sort of us driving uh other sort of top of funnel um growth um but anyways it's the classic centralization versus decentralization argument right like yeah and in most cases I I know people don't want to hear this but centralization often wins yeah yeah uh what's your take on the the pivot video for most podcasters we saw a big one today invest like the best now have video uh i' I started on video with YouTube basically I never really had a pure audio product uh I think the first episode we did was video uh we very much enjoy video but uh is there is there any hope for a creator that just wants to stay audio only for the future I I don't think so because again we're talking about Spotify and YouTube being the predominant platforms right now and we know that those alos they need the video they they crave the video crave I think users got got got wise to this actually it was during Co people don't realize it was during Co when before Co people were recording podcasts in studios in Boots right similar to how you guys are now y um but they weren't video boots right it was just like a microphone on a table and then Co everyone went home and the the way that these shows kept going was through zoom in Riverside so you get video for fre so all these podcasters got video for free and they were like oh [ __ ] if I upload this video to YouTube I get all this distribution yeah and now you can't go back the algo craves craves the video craves the video the AI guys um talk to us about uh I'm going to butcher the name O OBO I've only read OBO OBO uh so this is a company you basically incubated you're a co-founder but obviously you're you're still a full-time investor maybe talk about that Dynamic and then what what you guys are working on yeah recently co-founded this new company with my former anchor co-founder near stickerman he's the CEO he's you know he's running it full-time uh I am not full-time on as you mentioned I'm a full-time partner at light speed um basically the the premise behind OBO is very very simple um we we the humans you guys me everyone we have invested many many billions of dollars over the past couple of years in making machines uh very very smart right through through Ai and we believe with OBO that it's time for the machines to make the humans smarter and so this is a company the premise of AI making humans smarter you guys have all heard a lot of the talk about you know a hyped up use case of chat gbt has been oh it's going to be a personalized tutor it's going to help people learn chat gbt is not really built for that yes yes it's helpful for like oneoff asks hey tell me about this thing tell me about this thing but John it doesn't know everything you've ever learned and it doesn't know what your interests are and it doesn't know what your goals are and you know maybe learning a new language or learning about I don't know some theory around Finance or something and so that's the basic premise of what what OBO is solving um we have a a beta coming very soon if people want to be the first to check it out just go to our I guess our ex OBO Labs at OBO Labs um but I'm very very excited for it and uh yeah I think I think people are going to really like this product awesome yeah and you uh you dropped by the pmf for die cage to support the players recently and they're working on a problem that's that's sort of adjacent um uh but but yeah maybe you know and funny enough we we just before this we had the founder of synthesis which is an AI tutor and so feels like it feels like we're maybe I'm sure maybe people have already done it but sort of a broader Market map around you know Ai and learning maybe they we're in the App Store moment where there's a bunch of we need to build products around this stuff we have the new technology but you know what is the dominant product Factor product form factor for each of these uh use cases and so it's a knockout drag out fight good luck out there yeah yeah what I mean that's it's usually a good sign right couple things going consumers benefit I mean everyone benefits like you know you you you pace of iterations very fast you get to test a bunch of things you get try new stuff all the time everyone and then you know at the end a bunch of people make money which is great exactly how do you exactly how do you think about the pressure so you're sitting on both sides of the table right you're an investor at light speed getting an opportunity to look at and invest in some of the fastest growing most exciting companies in the world you're on the founder side now uh meanwhile the average founder is being inundated with content around companies going from0 to 10 or Z to100 million in this super short period of time meanwhile you at Anor you know pivoted multiple times and iterated towards this idea and eventually had a fantastic outcome but it wasn't this sort of straight shot linear as a Founder now and from the founders that you talked to is there just sort of this extreme pressure around I need to deliver faster results than ever and do you think that could have a negative impact on outcomes because when I think of OBO I think okay massive Tam massive opportunity this be A1 billion plus company if you look at you know companies like dualingo and things like that in the public markets but I could imagine that you're going to have to sort of iterate in the same way so what does success look like for you and what advice do you give Founders that are kind of facing that pressure to you know put up ridiculous numbers in a in a really short period of time or be um you know relegated to the like you know a sort of not top tier uh company yeah we we actually talked about this in the in the pmf for die cage in the cage the cage with the guys cage as one does there there are a lot of startups right now that are experiencing explosive Revenue growth right it seems like every week there that chart has a new line on it like you know zero to what you know the chart I'm talking 100 million ARR yeah six months two months one day Zero days yeah uh something we talk a lot about at light speed is is like high calorie ARR and low calorie ARR right there's a lot of like cheap ARR growth out there and I a lot of it has to do with the fact that AI is very magical people see these products they're kind of like Blown Away by them and they're like uh here take my credit card like I'm happy to pay um yeah but that doesn't necessarily say something about how sticky these products are or how good they are or whether or not these users will actually retain and so you know with a lot of these explosive High ARR companies uh that we've seen over the past couple of years with with AI it's not really a secret you guys have probably heard of this as well many of them are very very churny right they they they they turn very quickly a lot of trialing a lot of like who I want to experience This Magic Moment take my credit card but then I'm never coming back and so you know the advice I gave to the um the page was I think we got to remember to continue to pay attention to like the metrics that have always mattered right things like consistent user growth and retention and making sure like the retention corts flatten out they don't just like Drop to zero because I think people are getting like very very hung up on this AR metric which is great I mean it's a business that can go from Z to 100 in six months phenomenal but you can't ignore the traditional metrics that tell you whether or not a product is good and I think I think that's gonna be really yeah so on your side are you are you ready to uh you obviously started this with your former co-founder are you guys ready for uh you know I think you have like good instincts here but you you must be sort of ready to you know do as many uh hopefully it's a one shot you just nail it out the gates but I it sounds like you guys are ready to uh pivot as as many times or or sort of adjust the strategy as many times as as necessary because it is such a big problem space there has to be a there's definitely a billion dollar business in here somewhere but you know still takes work to um yeah find that spot absolutely I think I think you got to be willing to Pivot and by the way that's what we see like you know in places like YC these companies pivot sometimes like five times over the course of two weeks the pivot is so and um you know the other thing I would say is not only do you have to Pivot but you have to move faster than ever I mean the thing that I felt when I went in the cage with the guys was I've never seen people move this fast these guys have been in there two weeks they showed me what they're working on and I'm not going to reveal it they told me not to reveal it but the the amount of progress they've made in two weeks I've never seen anything like it yeah like they literally went from not having a line of code to having a very fully featured app IOS app that they're about to ship to the the App Store yeah there's just never been competition like this before yeah it's insane uh I interviewed this this guy Josh Mo on my podcast he he started this app um called wave you guys seen this app wave I it's kind of like kind of like Rola it's like a note-taking thing with a it cool it's doing like five million ARR he built it by himself just like he had never coded before in his life that's amazing and he us his AI to not only teach him how to code but to write the code and to generate marketing and it's just the level of intensity in competition right now is unlike anything we've ever seen that's fantastic uh switching over to uh putting on your your investor hat uh wanted to give you an opportunity you know light speeds big investor in xai um uh you know and has been just one of the most active investors across the foundation model landscape I'd love to uh you know besides the obvious you know you just sort of invest in Elon companies and you know you tend to do well what was like sort of more of um you know without going into you know go into however much detail you want but like break break down kind of the memo on um on the xai thesis yeah I mean a lot of a lot of what has been reported publicly you know aligns with with our our thinking and our thes uh thesis and that yes betting on Elon is a pretty smart thing but but more than that it's it's the level of intens I mean to again bring up back the speed and intensity that that he and the people that he hires uh brings to the team and so you know the first time we talked to that team and they were telling us about the data center that that they were going to build and again it's been very publicized at this point yeah um we were like wow like if if you could actually do this you would you would go from basically the starting gun to you know being at the same level or possibly exceeding open AI in in a matter of months in terms of model performance and and then they went and did it like they literally did it in like three or four months um and I think that type of intensity and speed and scale that that that you know only Elon and El Elon like companies can actually do combined with the fact that they've got obviously this incredible distribution channel right out of the gate through X um and not just a distribution Channel but a really unique content set to feed off of the model right this model unlike most other models it it has realtime information that they don't really have and and that realtime information also serves as a surface to trigger you know usage of the product Analyze This post tell me more about this um so I think those are some of the factors that that got us excited and the team has has far beyond delivered uh on what they said they would so it's been really exciting that's yeah what um uh you know obviously you can't share any details here but uh should the should the broader Market expect more Foundation models or is it kind of getting to the point you remember in crypto it was like okay we don't need another like Foundation level we don't need another L1 like like and then you'd see one and you'd be like really you know like this one this one built different um or or or do you think that uh you know the five or six major players thinking machines xai open AI SSI are those like the labs that you know you know we're sort of betting on uh or do you think there's room for for more teams The Way We Were framing this was like if it is commoditizing well ities are valuable oil is a commodity and everyone wants to drill for a well and more Wells you have the better get a bunch Wells yeah it's Capital intensive but if you put together a really great team you can just start a new oil company and being worth something you know but yeah what are you thinking about it yeah I mean I think you know I think a few weeks ago a lot of people wanted to have the debate about whether or not you know deep seek meant that models were Commodities and nobody should ever train Foundation models again I actually feel like that was the wrong conversation to be having you know the way we think about it at light speed is these these companies are not just models they are companies they have distribution they have customers they have data right they have security safety like things that enterprises actually care about and so you know I think should there be more models trained maybe but I don't think a model by itself is necessarily interesting I think there needs to be a product um and a team behind it and so I think if you were starting a model you know if you're starting a company today that was training a foundation model I think you need to either bring something very very unique to the table in terms of what that model can do or you you better have some other advantage in terms of distribution or uh or some sort of data that other players don't have access to uh that lets you jump up ahead and and I think like that's an example of something Elon and the xai team were able to do they were able to to build this data center in a way that no no one else was willing to do yeah to jump ahead right yeah so um yeah that that's a little bit of the way that that we think about it talk about it yeah that's fantastic you have any other questions uh I think we covered everything it's been great having you uh we'd love to have you on you know when you have news with OBO uh new Investments things like that come on uh we're all about you know conflict right so we want people coming on that have have positions in the companies discussed on this show highly conflicted yeah so it's uh no conflict no interest right exactly that's uh that's our we'll have you come on pump your bags then we'll have your direct competitor come on pump yeah yeah why not why not have you both on shout out to the guys in the cage by the way yeah yeah yeah um than thank you for uh thank you for coming on thank you for supporting the players and uh we'll have you back on here soon have fun are you gonna go play some music right now I I don't know maybe why notate around with that that Gibson in the background yeah generate some music honestly skip the skip the Gibson you're in Boston are you staying through St Patty's Day no unfortunately oh you got to go to S get get hammered on guinnesses and throw up in the street like you're a Boston College student yell about your stripe second yeah exactly yeah be fun in in in in another another timeline maybe in another life yeah yeah I don't know if the my my wife hey I decided to stay five day's B there's gonna be green beer there's gonna be green beer I have to drink it I have to do a keg stand in southeast I'm sorry exactly anyway understand she'll understand she'll understand great hanging out with you have a great rest of your day great to see you Michael we'll talk to you soon later guys talk soon cool Michael's a man we're we're like informally doing a full like deep dive on AI education today yeah we we got that we got OBO now I want to go to Conor Wick over at speak this is for language learning kind of a we already did a siis Gong whole segment on this by the way we did so I think we should skip this one yeah let's skip it but we but I do want to have want to have him on at some point um but yeah little little historical size gong you know you got to do it you got to do it any any excuse to hit the g really take well let's go over to Sager and Jetty uh good friend of the show uh he's reporting he's getting a little political but it's fashion based politics and so we'll cover it here on the show uh denied entrance to the chamber to the Senate chamber for Senator Jim Banks for wearing cloudrunner running shoes with a full suit and tie he wasn't wearing proper footw Footwear and Sager says the way I feel reading this must be what it's like to get high on heroin because Sager has been beating the drum on we need our politicians to be well-dressed they need to be wearing suits no more sweatpants no more hey dress is at least as nice as we do this show yes which John sometimes gets upset yes because I'm not wearing a jacket but I just like to wear a college shirt sometimes do a little business casual it's it's too casual for too casual unless it's casual Friday in which case we should be in Jeff Lewis tank tops anyway uh love love Sager highlighting that speaking of Jeff Lewis he's the next Post in here there we go uh he says uh Jeff Lewis over at Bedrock says things that go up only over 10year time Horizons uh select individual companies led by Transcendent entrepreneurs private and public tasteful ultr luxury real estate I like where he's going with this land in select locations select cryptocurrencies select precious metals and select artwork he says that is all I love it ominous what a great Post Yeah so if you're in the mag seven y rotate to select precious metals well if your mag s company isn't led by a Transcendent entrepreneur because if you are led by a Transcendent entrepreneur it doesn't matter if you're public or private you can still go up a 10 time Horizon but otherwise get out and get into some Ultra Luxury real estate some cryptocurrency some precious metals and some artwork I I I think we're we're getting up to speed with the Ultra Luxury real estate we're getting up to speed with the crypto and the precious metals uh I think we're behind on the artwork so we should have them on to talk about that where's where's the bull market there's always a bull market somewhere what artart great you can find an artist that you like buy up all of their available you know works and then just start uh you know putting them up in auction buying them yourself you know sort of Market chandelier bidding are you familiar with chandelier bidding uh think so it's a phrase for when you are essentially bidding on your own yeah Ju Just to like kind of raise the reserve on a on a piece of on something that you're you're auctioning off and of course if you win your own win your own auction then you have to uh then you have to pay the fee but the fee for the risk of pumping up the price demand I think that's just called Market manipulation sh chandelier bidding I just looked it up oh yeah is that where the auction the auction house tends to see a non-existent to see a bid from a non-existent part of the room so you go oh okay and and we're going up the auction house trying to their you're talking about is even more real where you know I I know people that let's say you own 30 pieces of an artist work and one of their pieces that's comparable to yours goes up for auction if it doesn't sell well then your entire collection just get sure so you might as well just buy might as buy Mark yeah mark it up Mark it up VCS do this yeah they're like they're like all of the all of the foundation model companies are worth so much because every time one comes to Market it's worth billions and so you know the the first one I invested in certainly has to be worth a trillion yeah who knows uh anyway uh speaking of a company that sorely needs to acquire one of these Foundation model companies D Apple uh plans one of the biggest software overhauls in its history for iOS 19 iPad iio iPad os9 and Mac OS 16 FKS if you love the photos app you're going to love this looking to revamp its operating systems for new generation of users and Raj Vier says I don't trust 2025 Apple to pull this off they might just incinerate the greatest business ever created uh and Chris Oren says yeah I'm taking the under on this I don't know I don't know if they can incinerate the greatest business ever created but uh they definitely need to try something new they definitely need to get some fresh blood in there take some risks they could really make the software much worse and it would still take a lot to actually compete with them on the hardware people don't like green bubbles and yeah the hardware is hard to make it's a very reliable product it connects to the wireless network reliably people forget that like you know a lot of the beauty of the Apple ecosystem is just yeah like it finds the 5G Tower or the LTE tower or it doesn't drop drop phone calls that often like that those are considered table Stakes but they could go away if you if you get lost in something else anyway um Jared Rosner says huge opportunities for AI startups that no one is talking about AI native Brokers when broker transactions can be fully automated those markets for context Jared hey really quickly we got Delan on the show oh bring in hey how