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Michael Mignano: How I Founded Anchor; Why TikTok could be a $2 TRILLION Company | 20VC #923

Mike Mignano is a Partner @ Lightspeed, one of the most successful venture firms of the last decade with a portfolio including the likes of Snap, Affirm, Epic Games, Mulesoft and more. As for Mike, prior to venture, he was Head of Talk for Spotify where he led the podcast, live, and video businesses for the world’s leading audio streaming platform. Michael came to Spotify through their acquisition of Anchor, a company he co-founded and is credited for democratizing podcasting globally. Mike has also been a prolific angel investor with a portfolio including Cameo, Pipe, Sandbox VR and Stir. -------------------------------------------- YouTube Timestamps 00:00 Intro 00:37 Big announcement 01:10 Why Lightspeed? 03:15 What are you nervous about? 4:32 What can be done better in venture? 7:99 How to tell a founder you don’t believe in them 10:32 What matters more, markets or founders? 11:32 Advice on what it takes to be a VC 14:29 How many checks do you want to write a year? 15:50 What was it like at the height of Anchor? 18:50 Will we see another next gen consumer social company? 20:30 Copy cat approach from incumbents 23:21 Why did Clubhouse not work out? 28:08 Why are incumbents moving away from the social graphs? 30:48 How should content be moderated? 32:05 Will TikTok be a $2 Trillion company? 34:00 Do the best social platforms start with creator tools? 35:48 Are you bullish on the creator economy? 40:52 Adobe’s future 41:48 Twitter’s super follow fiasco 43:15 Did Spotify miss out on social? 45:50 Biggest takeaways from Angel Investing 48:20 Biggest investment mistake 50:25 How to determine mission oriented founders 51:26 Biggest miss 52:30 NFT social graphs 55:50 Opensea’s future 58:05 Favorite book and why 58:52 Secret to a successful marriage 59:53 Most underrated angel 1:00:33 Biggest strength and weakness 1:01:19 What would you most like to change about startups 1:01:55 Most recent angel investment -------------------------------------------- In Today’s Episode with Mike Mignano We Discuss: 1.) Exclusive News: What exclusive news does Mike have to share today? What would Mike most like to change about the way founders experience the product of venture capital? How can VCs be better? What is Mike most nervous about in the new role? 2.) The World of Social is Changing Forever: Why does Mike believe there has never been a better time for the next social media giant to be born? Why are the largest social giants leaving behind the social graph? What is recommendation media? Why is it a better business model? How does the shift from social graph to recommendation media change the way large social giants operate and interact today? 3.) Startups: Risers, Fallers and Is There Room For Another Giant? What does Mike believe Clubhouse did well? What was their undoing? Does Mike believe BeReal is defensible? What features make it both sticky and defensible? Will TikTok be a $2 trillion dollar company? Will Meta catch TikTok or have they gone too far ahead? Will OpenSea be able to sustain and make the market for NFTs, despite crypto crashing? Should startups be concerned about large social giants “copying” their features? What does true defensibility look like in consumer social today? 4.) Angel Investing: Hits, Misses and Lessons: From writing over 50 angel checks, what are the single biggest lessons Mike has learned? What has been his biggest hit? How did that change the way he thinks about investing? What has been his biggest miss? In what way did that change how he invests? What advice does Mike give to all angel investors looking to invest today? -------------------------------------------- #MikeMignano #HarryStebbings #20VC #Clubhouse #BeReal #Anchor #Tiktokvsmeta #tiktokvsreels #venturecapital

Harry StebbingshostMichael (Mike) Mignanoguest
Sep 7, 20221h 5mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:37

    Intro

    1. HS

      Mike, this is such a joy to do. I've been looking forward to this one for a long time. It's been a long time since our last episode, but thank you so much for joining me today.

    2. MM

      Thank you for having me, Harry. Yes, I remember that first interview we did. It was probably, it was probably about seven years ago, six years ago.

    3. HS

      I-

    4. MM

      I don't even know. (laughs)

    5. HS

      I, I, I know. I feel like Dorian Gray. I was young and good-looking-

    6. MM

      (laughs)

    7. HS

      ... back in those days. But I, I wanna start, and we have some very exciting news today, so I'm just gonna hand over to you, uh, and say tell

  2. 0:37 – 1:10

    Big announcement

    1. HS

      me, what is this wonderful and exciting news that you have for me today?

    2. MM

      Yes, thank you. So today we're announcing that I'm actually joining Lightspeed as a partner on the consumer team, and I will be based here in New York City. And also as a fund, uh, my partner Justin Overdorf announced today that Lightspeed is gonna be planting a flag here in New York City and opening a brand new office. So that's the news, and thank you for letting me share it on 20VC.

    3. HS

      Not at all. I find it so much nicer to have like a podcast episode. It really brings stories to life. But tell me, you know, you've had an amazing career so far with Anchor and with Spotify. You could've chosen

  3. 1:10 – 3:15

    Why Lightspeed?

    1. HS

      many funds to go and work at. Why did you choose Lightspeed?

    2. MM

      So I've been angel investing for about three years now, and while I've really enjoyed angel investing, it's been a blast, I definitely wanted to kind of take my investing to the next level and join one of the world's best and most storied venture platforms. And you know, in talking to a lot of them and, you know, partners that I knew at different funds and talking to a number of different funds throughout this process, I really felt like Lightspeed was unique in that we are, number one, truly global, and we have been for more than 15 years. You know, the past decade has obviously been, uh, in a big way, uh, about the US and the companies coming out of the US, but I really believe that the future is global, so it was really important to me to join a global platform. Uh, I wanted to join a, a fund that had really deep domain expertise across a number of different, uh, areas. Uh, I'll tell you that when I was building Anchor, I always appreciated investors (laughs) who actually had real-world experience and they weren't just check writers, so that was very important to me. I also wanted, um, a fund that was really strong on partnerships and not egos. Uh, a thing that we did in Anchor was we were really focused on building a culture around a mission, uh, not about individuals. We had this thing, missionaries not mercenaries, and it was very clear to me that Lightspeed was similar. And then lastly, you know, sort of as we were, as we were going into... uh, as I was going into this new role and looking at the landscape and the market, um, and obviously, you know, we're in a, we're in a period of uncertainty in the market right here, I felt it was really important to join a fund, uh, that could support teams at every single stage, full stack support. Uh, Lightspeed invests in every stage, and so that was really important. So between all those things and, you know, the, the amazing conversations, uh, I've had with everyone at the fund and the relationships I've built there with Alex and Nicole and, and Paul Murphy, who, who actually hired me at Aviary at my first startup job, you know, uh, 10 years ago, who's now at Lightspeed as well, it just made, it just made so much sense for a number of reasons. So yeah, I'm really excited.

  4. 3:15 – 4:32

    What are you nervous about?

    1. MM

    2. HS

      Paul is fantastic. I totally get you.

    3. MM

      Yes, he is.

    4. HS

      I, I do wanna ask, like, new things are always nerve-wracking. When you think to like the next few years and becoming a VC now, having been an angel and an operator, what are you most nervous about?

    5. MM

      So I think it's really easy to be pretty loose with angel checks if I'm being honest, right? It's your money. You're answering to nobody else. The checks are relatively small, so it feels less risky. But obviously with venture, and you know this way better than I do, you've been doing it for a while, you're investing other people's money. And now you're not just investing for yourself, you're investing for others who are trusting you to make really smart (laughs) decisions. So you know, a- and not only that but if you're joining or leading venture rounds I should say, you're obviously joining boards, so you're signing up for a very meaningful and long-term partnership. So I think what I'm trying to say is the stakes are much higher.

    6. HS

      Mm-hmm.

    7. MM

      And so all this will be new to me, and like anything I think there, there's always gonna be a certain level of anticipation. So tha- tha- that's probably what I'm, um, I'm, I'm anticipating most, but um, but yeah, uh, I, you know, I think, I think a lot of it is gonna be new.

    8. HS

      So you mentioned boards there. I've sat on many boards. Um-

    9. MM

      Yep.

    10. HS

      ... I've only sat on one that has actually provided any value at all, um-

    11. MM

      (laughs)

    12. HS

      ... out of about 15. Um, I, so I think boards can be done better in venture along with most of the actual

  5. 4:32 – 8:39

    What can be done better in venture?

    1. HS

      product itself. What do you think can be done better in venture having really dog tested it, if that's a word, as a product?

    2. MM

      Yeah. So thinking back to my experience being on the other side, right, as a founder of Anchor, um, one of the things that I think we did really well at Anchor was we built this culture of very direct communication built on mutual respect, um, kind of like a deep understanding of everyone's personal priorities and goals, and I think venture could use a little more of that personally. I think it could use more directness between founders and investors. I think, I think if founders had a better understanding about what investors' goals were, it would probably enable investors to be more transparent. Um, I, I didn't like the culture of investors sort of milking relationships with founders when they never had any intention of investing. Um, I, I also never liked how investors were so opaque about, you know, reasons they're passing. Uh, my, my sense is like we're all adults in this industry, yet I find people are so afraid to hurt each other's feelings that they avoid directness of communication. So I'm really hoping to bring more of that and, um, you know, I think, I think investors don't often realize that it's really hard for founders, um, when you don't know where you stand. And, you know, having been in that situation many times, I can tell you it creates-... lots of tension, lots of additional pressure, and so, you know, I want to bring the types of candor and directness, uh, to venture that we really had when building Anchor, which I think was a big part of why we were successful.

    3. HS

      Where do you think are a couple of situations where founders don't know where they stand, where it's critical that they should know where they stand?

    4. MM

      I th- well, I think the pitching process, obviously. Like, you know, that- that's a process that I think could use way more efficiency. Um, I think working with existing-

    5. HS

      How is that? Sorry, sorry, I'm- I'm- I'm- I've got better at interviewing I think, I hope. Maybe I'm more annoying. Um, how could that be better? What would you like to change there?

    6. MM

      I think in general, the- the pitching process could be faster and more- more efficient, and, uh, investors could be more transparent with the reasons they're passing. I think that would help founders improve and actually probably result in a better outcome between the investors and the- and the founders in a future round, right? If a founder knows the real reason why an investor is passing, they can work towards achieving certain goals that might make it a better fit in the next round, right? Another example I would say is, um, I think founders sometimes don't know where they stand with their existing investors and whether or not investors are gonna be excited to- to back the next round or if it's off strategy for them, so I think there should be more, um, discussion and conversation about what the future relationship might look like between a founder and investor. And so-

    7. HS

      So hang on-

    8. MM

      ... I think there are a number of situations like that.

    9. HS

      No, I'm jumping in here. Um-

    10. MM

      Yeah, go for it. You're an-

    11. HS

      Wait, wait, wait.

    12. MM

      ... you're an investor. Tell me that this is realistic.

    13. HS

      Well, I mean, so like first off, like the reason the investors aren't as direct as they should be most often in terms of the feedback is 'cause they want to retain the optionality. If you're a multi-stage fund, you don't want to say, "Mike, I'm turning you down at the seed because I really don't believe that actually you have what it takes." 'Cause they don't want that founder to not come back to them at the A or the B in case they turn into something great, so they wanna have a bland, vanilla reason that is not enough for you to be dissuaded.

    14. MM

      Of course.

    15. HS

      But that's reason one, um, I think. Um, what were your other ones?

    16. MM

      But you should just say that then. You should just say, "I don't believe in this company yet. I actually don't think (laughs) ... What I'm-

    17. HS

      Or-

    18. MM

      ... seeing now, I don't think you have what it takes, but I'm hoping you can prove me wrong."

    19. HS

      What if it's "I don't believe..." Heh. The- the hard one, and that I do struggle with, what if it's "I don't believe in you"?

    20. MM

      I think you should say that.

    21. HS

      Pfff.

    22. MM

      (laughs)

    23. HS

      (laughs) Ooh. That is deep. I-

    24. MM

      It's the truth. It's the truth.

    25. HS

      It- it- it absolutely is the truth, but, I mean, that's- that's tough to digest. And you also get more-

    26. MM

      I think you- I think you'd be respected more from the founder if you told them that directly.

    27. HS

      Okay. I get that. Um-

    28. MM

      (laughs)

    29. HS

      ... I like it. What about... You know, the hard thing about being in a partnership is, you can wanna do a deal, but your partner-

    30. MM

      Yeah.

  6. 8:39 – 10:32

    How to tell a founder you don’t believe in them

    1. MM

      think a founder doesn't often know that. They actually don't know the dynamics, and this is what I meant earlier about like the found- the investor's goals. I think the investors should explain to founders, like, what the dynamic is, how deals get done, what their incentives are, what kind of ownership structure they want. These are all hidden variables that make it very hard for the founder to know what to deliver to the venture capitalists to get the investment.

    2. HS

      Can I be blunt? Should founders not-

    3. MM

      Of course.

    4. HS

      ... should founders not know this? And you say, "No, no, their job is to create product, not to fundraise," well, kind of not. Like, that is a core part of business building. And with the transparency of data that we have today, podcasts like this, they can hear very easily before meeting you exactly what type of deal you like, your ownership levels, the partnership dynamics. It's not like it was. Should they not know already?

    5. MM

      Yeah, I mean, I think there's a lot more information out there today than maybe when I was building a few years ago, and maybe that's a great reason for us to be talking about this right now on this podcast. Hopefully somebody will use this podcast to- to be better informed when they go into a pitch meeting.

    6. HS

      Man, I- I love that in terms of the directness of communication, and when someone comes round to my house and, you know, uh, shouts at me for being so direct, I will blame you. Um... (laughs)

    7. MM

      Pl- please do. Please do.

    8. HS

      (laughs) I-

    9. MM

      Look, there's a way to be direct and respectful at the same time. And in fact, I believe directness is more respectful, because you're giving somebody the truth, right? And- and- and I just really believe in the truth.

    10. HS

      Mike, I'm a founder and it's me that you don't believe in. You're a VC.

    11. MM

      (laughs)

    12. HS

      It's your first pitch at LightSpeed. How do you tell me that you don't believe in me?

    13. MM

      Oh. So, okay, so, I think I would say, "Listen, Harry, I think that this is a really interesting business. I think there's a ton of opportunity here. Um, I'm f- I don't believe that you're the person to do it. Now, you can change my mind through this next stage to the next round, um, but right now, I- I just don't think you have what it takes, and, uh, I wish

  7. 10:32 – 11:32

    What matters more, markets or founders?

    1. MM

      you all the best of luck."

    2. HS

      What matters more, market or founders?

    3. MM

      Um, oof. You know, I think, um, I think people often underestimate the potential of a market to develop and evolve.

    4. HS

      Mm-hmm.

    5. MM

      You know, obviously, a- a- a reason we heard often with Anchor was, "This is not an interesting market. Podcasts have been done before." But I think that ignores what podcasts can be, right? I think, "This isn't a big enough TAM" is like a very easy excuse to give to a founder, but the reality is, all of the biggest markets were never as big as they were until the defining companies made them that way. And so, um, I guess it's probably the founders, if that makes sense.

    6. HS

      I think a huge market can cover a lot of sins on the founder's side. That said, whenever an investor says, "I think you're amazing, amazing, but the market's not big enough," a truly amazing founder would expand the market, would find the agility-

    7. MM

      Exactly.

    8. HS

      ... within it, would do something to make it bigger. You've worked

  8. 11:32 – 14:29

    Advice on what it takes to be a VC

    1. HS

      with some of the greats on the investing side. Did you get advice before you entered and before you joined LightSpeed in terms of what it takes to enter venture and be a VC?

    2. MM

      Yeah, a- absolutely. I, you know, I have a number of people I really trust who have been doing this a really long time, and, you know, I made this decision very carefully over the course of many months, and one topic that I find, uh, is often discussed, um, when I'm talking to investors about this is...... sort of the pace at which an investor should make their first deal. I, I've heard a wide (laughs) range of suggestions on this one. Some have told me, "You should wait a whole year before doing your first deal." Uh, on the other hand, another investor, one- in my mind, one of the all-time greats, told me recently that, "You should, assuming you see a great deal and a great company, you should write your first check in the first 60 days." And, uh, and his reasoning was that if you wait too long, you create this pressure cooker scenario where you start to overthink your strategies and your motivations and your filters and your decision-making. And so, by making that investment early, you're sort of ripping the Band-Aid and releasing that pressure before it builds. (laughs)

    3. HS

      That's fascinating. Where do you-

    4. MM

      Yeah.

    5. HS

      ... la- where do you land on that, how fast to write the first check?

    6. MM

      Um, well, I, uh, today's my first day, so, you know, let's see if this, if this holds true. But, you know, I, I'm, I'm open for business, you know what I mean? Like I, I'm, I'm a person that likes to move. I, I'm, I, uh, I like to execute, and so I think I err more towards the side of moving quickly, rather than waiting a year. Especially because I feel like I've gotten to practi- I know angel's not the same thing as venture, but I've gotten to practice investing a, a bit over the past couple of years. It's not like I'm starting completely fresh.

    7. HS

      I have so many thoughts on this one, because like that's often cited that actually your first check's always gonna be actually not a very good one. It's a bit like V1 of your product. You're gonna look back on it in five years and go, "I probably wouldn't have done that."

    8. MM

      (laughs)

    9. HS

      In which case, just do it fast, kind of get it out the way, um-

    10. MM

      Exactly.

    11. HS

      ... and move on. But then I've also had it in the past, Mike, when my first institutional check-

    12. MM

      Mm-hmm.

    13. HS

      ... was not very good, and it actually damaged my confidence for quite a while, and I was hesitant to deploy more 'cause I was nervous. It was a bad first one, and I was very nervous, and it was obvious. And so I, and then you have the alternate school of thought, which is, "Actually, Mike, just do a series C that's pretty humming, alongside other great people, and get a B+ under your belt." I don't have an answer for you, but there is your multiple choice. (laughs)

    14. MM

      I, I appreciate that. Yeah, I'm, I mean, look, when I was building products for, uh, you know, for, for 15 years or whatever it was, I naturally gravitated more towards the iterative approach, right? Like, don't overthink it, ship the product, get it out in market. You're gonna learn, you're gonna know your mistakes, you're gonna, you're gonna adjust based on that. And so I think my inclination is to take a similar approach to invest, to investing, where it's like, get, get your licks in, get your reps in, you're gonna learn. It's, it's, it's a journey, right? It's a marathon, (laughs) not a sprint. And,

  9. 14:29 – 15:50

    How many checks do you want to write a year?

    1. MM

      uh, and go from there.

    2. HS

      How many checks do you wanna write a year, Mike?

    3. MM

      I think, you know, I, I, I think, again, it's my first day on the job. (laughs) I gotta see how it goes. But I, I, uh, you know, I think I'll probably write, uh, a handful of maybe early stage, uh, uh, let's call it seed checks, and then a handful, a small handful of, call it As and Bs, uh, as well per year.

    4. HS

      And we're focused explicitly on consumer?

    5. MM

      I think mostly on consumer. Look, it's, it's a, it's a partnership. It's a very collaborative team, and I think, you know, I think everyone on the Lightspeed team has an opportunity to invest, you know, cross-sector, cross-geo. Um, but I think where I'll spend most of my time is consumer. And, you know, based on my experience, I think where I can be really, really strong as an investor is helping the companies that really need to go from zero to one. That's where I've sort of perfected my experience in terms of building products. Um, you know, taking products that literally have no audience and building them up to, you know, products that have hundreds of millions of users. And so, um, I think those are the types of companies, the types of consumer companies, where I'll focus. Um, but I think there's an opportunity, like I said, to invest cross-sector, cross-geo, cross-category, et cetera.

    6. HS

      You s- you said about your experience going from zero to one there. I'm not sure if you know this, but when I was like 18, 19 I was in SF, and this was when Anchor was so hot. This was like-

    7. MM

      Mm-hmm.

    8. HS

      ... V1 of Anchor. Consumer, like

  10. 15:50 – 18:50

    What was it like at the height of Anchor?

    1. HS

      very heavily consumer-focused, pre-, you know, the second shift. Um-

    2. MM

      Yep.

    3. HS

      ... it was every VC wanted to talk to you. Everyone loved you. And I wanted to ask you, when you have the venture and the tech world praising you in those hype moments, what do you and what did you tell yourself?

    4. MM

      I think it's important to acknowledge up front that when we found ourselves in that situation that you're talking about, I remember it very, very vividly, um, we had never been in that situation before. I had never, uh, started a c- it was my first time building a company, first time, you know, um, building my own product from scratch and launching it to the world. And like you said, there was tons of hype pretty much overnight, like the day we launched it. And so, if you've never been in this situation before, it's really easy to get ahead of your skis and think you've won. Um, you know, we wanted to be the social network for audio, right? So there was already a social network for, for photos. That was Instagram. You know, video had YouTube, etcetera. We wanted to be, we wanted audio to have Anchor. And I will admit, in those first few weeks, we had thought we had won because all of the biggest and most respected luminaries in, in tech, people I'd only ever seen on, on Twitter, never met in real life, were telling us that we had won, right? They were telling us that we were the biggest (laughs) company in the world.

    5. HS

      Wow.

    6. MM

      And they were, you know, flying across the world to bump into my co-founder and me at random events to try to get us to take their money. And so it's very easy to hear all of these super respected people tell you that you had figured it out. But the reality is, which we didn't know at the time, is that they are sp- they're actually speculating, and they are betting that you will win, not that you had already won. And, uh, and of course what happens is, you know, once the hype dies down, you know, all the noise drops and you're able to see the real metrics and like what's actually happening. And, and we hadn't. And so, um, you have to sort of swallow your pride and reorient yourself and re-anchor yourself, no pun intended, and, uh, and remember that this is a marathon, not a sprint. You gotta swallow your pride, and you gotta get back to work. Um, because these things, success comes over time. It is never an overnight thing, even though sometimes it looks that way.

    7. HS

      How long was that hype cycle?

    8. MM

      So, I think when we first launched, it probably la- lasted two months. Um, and then I think we spent, you know, a good six to eight months constantly trying to recreate it and bring it back and do these little things to get that spark back. And it never did, and, and you know, at a certain point, you look at your runway and you look at, you know, you're gonna, you're gonna run out of money. You're gonna let down not only your investors, but your employees who are counting on, you know, counting on this company to provide for their families. And you realize that you have to do, you have to do something dramatically different. You're, you're in this existential moment and you have to address it. And that can be a very, very powerful forcing function for turning the company around and doing the right thing.

    9. HS

      Can I ask, we, we've seen quite a few consumer social

  11. 18:50 – 20:30

    Will we see another next gen consumer social company?

    1. HS

      companies gain very, very, uh, mass adoption, huge popularity and hype, whether it's your Anchor, you know, obviously a while ago, and then there was like, I think Pop Shop or Pop Show, I can't remember what it's called, the, the benchmark company that kind of was very hot, and then there's obviously Clubhouse which was very hot. You know, th- there's been many. I'm just kind of regaling from my past memory. But none have broken out into Facebook, Instagram, Snap. Is there room for another, given their ability to copy so effectively as they're trying to with BeReal now? Is there room for another, and will we see a next gen social giant, or actually not?

    2. MM

      I, I think we will, and if you had asked me this question about a year ago, I, I may have said the opposite. I may have said no. I think there's this thing happening right now, I recently wrote about this trend called recommendation media, where the biggest social platforms in the world are actually pivoting more to be recommendation engines, and, and really more like entertainment platforms. And I think as a result, there's going to be sort of this vacuum, um, of social experiences, true social experiences. And so I think if ever there was a time for a new startup to emerge to create a great new groundbreaking social network or social experience, now is the time. I mean, literally the most iconic social media company of the past 15 years, Facebook, literally just walked away from s- their social graph, right? They're, they're pivoting to recommendation media. They've been very, very public about this. And so if there was ever a time to place a contrarian bet and lean into being the next big social platform, this is probably that time.

    3. HS

      I, I, I get you. My concern is that, like, fundamentally,

  12. 20:30 – 23:21

    Copy cat approach from incumbents

    1. HS

      you know, I tweeted about BeReal the other day.

    2. MM

      Mm-hmm.

    3. HS

      It's, the numbers are insane, and I got actually a wave of criticism. And everyone said, "Well, all of the incumbents are actually trying to copy them as we speak, and they tend to do it very, very well." How do you think about the copycat approach from incumbents, and is that a worry or a legitimate worry for the, you know, uh, up and comers?

    4. MM

      I, yes. 100%. I think it is a worry. And admittedly, I think it is a worry for BeReal. I think BeReal's a great product. Um, the reality is, I don't think their format is, is, is something that Instagram can't copy easily, right? It i- it is a photo at a specific time of the day. I think in order for a, a, a platform, a new social platform, uh, to win, is really to have a defensible format. And the reality is, I can't tell you what that defensible format is because it doesn't exist yet. Um-

    5. HS

      I, I, on BeReal I can. I think the defensible format-

    6. MM

      Okay.

    7. HS

      ... is the albums that they allow you to create, which is a newer feature. So you can look back on all your previous BeReals and see the album across a longer period of time.

    8. MM

      That's really cool.

    9. HS

      And so, in a similar way that Airbnb had reviews which you don't want to lose when you, you wouldn't switch away from Airbnb 'cause you'd lose all your reviews, you'd lose your ratings, your rankings. With BeReal you'd lose all of your past historical BeReals over a three-month period. And actually I think Instagram, it's not natural for them to integrate a separate BeReal Mike Mignano page in a separate profile. It would be very awkward. You'd almost have-

    10. MM

      Right.

    11. HS

      ... two profiles, a daily profile and then your long-standing. It doesn't make sense in, in my eyes. That would be-

    12. MM

      Yeah, and-

    13. HS

      ... ... no sense to me.

    14. MM

      And that's a, and that's by the way, that's a great example of, of building a defensible format where it's hard for another platform to go. You know, a lot of people like to talk about Clubhouse now and how it, you know, whatever, it didn't work out, there was this hype cycle, it's over. But to give Clubhouse a lot of credit, I actually think their format was pretty unique and pretty defensible in that it would've been very hard for Twitter and Facebook or Meta, uh, and, uh, and Instagram to easily replicate that format in a way that made a lot of sense with those platforms. Now obviously it didn't necessarily work out the way everyone thought, but I think that's actually (laughs) for completely different reasons, not for the lack of defensibility of the format. And so I think the key for a new social network to break out is it has to do something different that is hard for another platform to travel to. And arguably no platform did this better than TikTok, right? They built a new tool set, uh, which ended up creating a new type of format that obviously was and is copyable. It's all just software. Software can be copied. But as we've seen, it's taken Meta a l- uh, a little bit to get there. (laughs) It's taken them a couple years and it's given TikTok the e- you know, the time to grow into one of the most defining platforms in the world right now.

    15. HS

      I have to ask, why do you think, and you know, you, you obviously have this unique

  13. 23:21 – 28:08

    Why did Clubhouse not work out?

    1. HS

      purview from the Anchor days. Why do you think Clubhouse didn't work out? It's where we reconnected after many years.

    2. MM

      Sure. That's true. (laughs) It, it was. So, um, I think that live content is extremely challenging, and I don't, I, this is not unique to, uh, to audio. I think live in general is, on the internet I think is kind of a flawed format. Um, if it's just live, only live, and not, and there's no asynchronous component, um, I think it just becomes a really challenging math problem. Right? You're basically saying, "Hey, in order for this thing to get scale and to achieve va- achieve, uh, a large amount of value," and I'm talking about this thing being the content, you know, a lot of people need to be available to consume this thing at this exact moment. And really, what the internet has showed us is that there's way more value that gets generated in asynchronous content, because it can be consumed kind of on somebody's own schedule.

    3. HS

      Mm.

    4. MM

      Um-... arguably, this is why Spotify (laughs) has been so massively successful, or YouTube, right? It's because you can fit into any calendar and any schedule now. You don't have to have somebody, uh, be available at any given time. And so, I see a lot of criticism on, o- of Clubhouse o- online that I don't fundamentally agree with, which is, "Oh, they didn't focu- focus enough on the community. They didn't, they didn't nurture the community enough." I actually don't think that's the case. I think the format was flawed from the beginning. Um, totally cool of them to try it, and I think that, I think, I think it was amazing. But I think in order for it to have maybe worked a little bit better out of the gate, they probably needed to go to, um, on-demand asynchronous, uh, playbacks, or whatever they call them, replays, from day one. Um-

    5. HS

      Is, is that, is that not quite an easy feature? You could essentially record every room and have a repository, a library where you could go into tech, you could go into art, sport, and look at the historical for the last week.

    6. MM

      So there's two things I'll say about that. Technically, yeah, it's kind of easy. On the other hand, you know, I can tell you that when we were a three-person startup, there's only so much you can do on a given day, right? You really have to focus. And they were getting so much traction, and so m- and I, I have to imagine that it was hard even just to keep the servers up. So, I can empathize with the fact that they have to focus. Secondly, I can also tell you from the Anchor days, replays of audio is, is also a tricky place for them to be. Again, I said that the live Clubhouse format was unique, and I agree. That's, that's somewhat defensible in terms of uniqueness. But what is not unique is on-demand consumption of a long-form audio file, which feels and sounds kinda like a podcast. The thing that we saw in the early days of Anchor and still saw, you know, up until when I recently left Spotify was listening habits of podcasts are very, very hard to break. If you are an Apple Podcast listener, you're almost definitely never going to switch away from that. If you are a Spotify listener, you're almost never going to switch away from that. Now you've got this other app, Clubhouse, which is putting out all of these on-demand asynchronous audio files, which kinda sound like podcasts. Are you really gonna leave Spotify to go listen to this one audio file when Spotify has all the audio files? So, i- it's... it, it was a bit of a paradox, I think, for them, in my opinion.

    7. HS

      I think, I think fundamentally it goes down to the question of quality of content, and the truth is, if you are doing live content in the way that Clubhouse was, it is not as high-quality as researched, as edited. I have a core metric which is word-to-value ratio. Every sentence you say has to deliver value, and if it doesn't, it gets edited out. These aren't-

    8. MM

      Yup.

    9. HS

      ... edited shows. But, in Clubhouse, uh, y- "That's a brilliant question, Mike. I've been thinking about it for a long time, and across the many months I've been thinking about it." For fuck's sake, just answer the fucking question. Like-

    10. MM

      (laughs)

    11. HS

      ... seriously. (laughs) Um, that, and then also, I think we're forgetting this was like a freakish like social change in how we behave.

    12. MM

      Hundred percent, yeah.

    13. HS

      We were all trapped with COVID at home. Like, we were lonely as mince, like, as anything. And so, I totally think that's a problem.

    14. MM

      Yeah, I mean, you know, you'll remember this thing that was going on in the early days of Clubhouse where the only thing people did, not the only thing, I'm, I'm not giving it enough credit, a thing that a lot of people did in Clubhouse was talk about Clubhouse.

    15. HS

      (laughs)

    16. MM

      I think there's actually a fundamental reason, I think, but I think there's a reason for this, and I think it goes to your point, in that producing high-quality audio content is hard. It's hard to come up with content to talk about. So if you're sitting on this stage in this live room in front of a thousand people and you're not sure what to talk about, it's easy to go to, "Hey, this platform's pretty interesting, huh?" It's just like an easy topic to reach for. Um, so yeah, I think, I think, I totally agree with you, like producing high-quality audio content is really hard. And, and obviously we learned that, uh, in, in the Anchor journey.

    17. HS

      Sorry, I'm, I'm not nearly as deep as you in this, but you said about kind of the incumbents moving away from the social graph towards the recommendation engine.

    18. MM

      Sure.

    19. HS

      We saw,

  14. 28:08 – 30:48

    Why are incumbents moving away from the social graphs?

    1. HS

      you know, last week, um, Snap, uh, actually announce shutting down Zenly, a completely bizarre decision in my mind. Um, 40 million users, incredible team, no idea what's going on there. Sorry, I know that's a Lightspeed company, forgive me. (laughs) Um, but l- my question to you is, why are these incumbents moving away from the social graph when it served them so well and it's the core of their very good business?

    2. MM

      Because I think it's, it is not defensible anymore. It's actually very easily commoditized, right? So, um, there, there are a number of reasons here. So, it used to be that the way that content got distributed on these platforms was through your social graph, right? You would join, let's just use Facebook as an example, you would join Facebook, you would get 100 friends, and you would post a piece of content, and it could instantly distribute that content to those 100 friends. And arguably, that distribution was guaranteed. Gave you a lot of power in terms of distribution and programming. But in reality, it's actually not that efficient a means of content distribution. Just because you can distribute a piece of content to me doesn't mean that it's going to resonate with me. In fact, it might not resonate with me at all. And in fact, it might be problematic. It might be a piece of content that has hate speech in it, or something that needs to be moderated. And so what these platforms were doing was they were effectively giving away free distribution that, um, that was more or less guaranteed, potentially very expensive for them in terms of, uh, content moderation, and maybe not really that ef- efficient in terms of engagement and, uh, in terms of driving ROI for the business. Well then TikTok comes along and they say, "Hey, forget the social graph. This thing is not that efficient. We're gonna, we're gonna determine the efficiency. We're gonna, we're gonna program every single piece of content so that it, uh, has the lowest cost for us in terms of content moderation or whatever, and the highest engagement in terms of ROI, and we're gonna basically instrument maximum revenue for the, for the, for the platform, right?" And, uh, and so, I think what platforms are realizing is that this is actually just like a much more efficient business model for them. And not only that, the social graph, as I said, is completely commoditized. Now every social product that comes out can instantly have a social graph just by ingesting your contacts list, right? So you and I meet on the street somewhere. You say, "Hey, Mike, what's your phone number?" I give you a text. Now I'm in your contacts. You sign up for BeReal or some other new social, social platform. And boom, they have your social graph already. So the thing that Facebook built 15 years ago that was so defensible and so unique at the time is just not that unique anymore, and it's a bad means of content distribution.

  15. 30:48 – 32:05

    How should content be moderated?

    1. HS

      I have to- you- uh, there's many things I want to unpack. I'm loving this chat.

    2. MM

      Yeah, sure. Yeah. (laughs)

    3. HS

      You talked about the- the content being posted. It is a complete fallacy that with 500 hours of YouTube videos submitted every minute, YouTube, Google, anyone is able to moderate the content efficiently at that scale. Am I not wrong? And is it just completely unfair to expect them to?

    4. MM

      No, you're- you're right. Here's the difference though. So when- when the platform has control over the distribution, they don't owe the distribution to anyone. Yes, there may be a problematic piece of content, but if it's problematic and they're getting take down requests, just bury the distribution. Right? Just, like- just- just bury it and nobody will ever see it. Whereas if somebody puts out a piece of content that's doing really well and it's not getting take downs, dial it up. Increase the distribution, increase the ROI. The- the difference is in social media they can't make that decision because they're on the hook to distribute the content to those 100 friends regardless of whether or not it's expensive in terms of moderation or it's not engaging in terms of value and ROI. So the moderation still exists, but- but they're not on the hook to deliver it anymore. They can just bury it. And they can use machine learning to pattern match and know which types of content

  16. 32:05 – 34:00

    Will TikTok be a $2 Trillion company?

    1. MM

      to boost and which to bury. Does that make sense?

    2. HS

      It totally does. On TikTok, I don't think I've ever been as bullish on a company as I am on TikTok. I am addicted.

    3. MM

      (laughs)

    4. HS

      My assistant is addicted-

    5. MM

      Yeah. It's- it's amazing.

    6. HS

      ... my mother is addicted. It's fucking amazing.

    7. MM

      (laughs)

    8. HS

      And- and- and so my question... And do you know they're a compound startup as well in that, like, Rippling style? Like, they have all in-built tools. Like, they rebuilt Slack for themselves. They re- uh-

    9. MM

      Oh, I did not know that actually. That's interesting.

    10. HS

      Yeah, they rebuilt every single tool completely vertically integrated. I mean, it's insane.

    11. MM

      (laughs) That's really cool.

    12. HS

      Do you think TikTok will be a $2 billion company?

    13. MM

      A $2 billion company? It- it-

    14. HS

      One of the biggest companies in the world.

    15. MM

      I'm assuming it's more- it's worth more than $2 billion at this point, no? Did you mean $2 trillion?

    16. HS

      I'm sorry, $2 trillion. (laughs)

    17. MM

      Oh, okay. (laughs)

    18. HS

      That's pretty... Do you think it'll be a $2 billion company? I- I think you're behind that. (laughs)

    19. MM

      (laughs) You know- you know what's cooler than $2 billion? No.

    20. HS

      (laughs)

    21. MM

      Um, so here's the thing. I think the next couple of years are the battleground.

    22. HS

      Mm-hmm.

    23. MM

      Right? So Facebook, Meta is now saying, "We're coming into this space." I think right now TikTok has the advantage because they've sort of, um, invented this format. They've popularized the format. But, uh, the reality is, the thi- the- the elements that will end up being critical on this battleground are, um, ocean of content from which to do matching and recommendations and best in class machine learning and computing power. And, uh, there's no doubt that Meta, one of the most valuable companies in the world, can definitely have both of those things. So I think right now if TikTok can sort of fend off Meta for the next couple of years, they do have a shot at being one of the most valuable companies. But I'll be honest, I think Meta has just as good a chance as them or anyone else to displace them over the next couple of years, so I think this battle sort of will be won over the next, let's call it, 24 months.

    24. HS

      I- I totally agree with you. Can I

  17. 34:00 – 35:48

    Do the best social platforms start with creator tools?

    1. HS

      ask, you know, when we think about, um, the starting point for a lot of these social tools, I- I remember once-

    2. MM

      Yeah.

    3. HS

      I- I don't remember if it was, um, Kevin Systrom or, you know, Mikey who- who said it, but they said that all great social platforms start with a tool that enables creators to create. So for them it was filters on pictures, for others it's, you know, the ability to be a medium, it's the ability to write freely in beautiful editors, you name it. Um, do you agree with that idea that the best social platforms start with creator tools?

    4. MM

      I do agree. Um, and I learned this. I mean, not that, you know, Anker ended up being a social platform, but, um, in the early days of Anker we just gave people a microphone and we sort of cut them off at two minutes. We didn't give them any tools. And we found that people did want to create, a lot of people created. I mean, you were- you were part of that early community. (laughs) Lots of people were creating. But admittedly, uh, the content was not that good, and so it didn't- it didn't drive an audience at all. It was- it was, like, you couldn't listen to it, to be honest. And where we really saw gains and started to see the potential for something really big was when we gave people creative tools, when we gave them the superpowers to do things that they couldn't previously do. We gave them effects to change their voices, we gave them sound effects, we gave them music, we gave them lightweight editing tools. And the moment we did that, they sounded like professionals. They sounded really cool. And it motivated them to want to create more and it motivated people to want to come and listen. Right? And so if you can do that successfully, you can build a really, really big business. The key is, as we talked about a little while ago, can you build a defensible format that Meta can't just copy with the flip of a switch? Because if they can, then yeah, you're- you're- you know, you're dead before you really have even gotten anywhere. But if you create something defensible, yeah, I agree. I- I think that is the recipe for- for building a really, uh, sustaining and- and long,

  18. 35:48 – 40:52

    Are you bullish on the creator economy?

    1. MM

      uh, long living platform.

    2. HS

      Speaking of those creator tools, I have to ask you again-

    3. MM

      Sure.

    4. HS

      ... despite being a creator myself, I'm not bullish on the creator economy. And I'm not bullish on the creator economy for the simple reason that I think it follows the most extreme version of Pareto's principle where 99% of revenues accrue to 1% of creators. I'm very grateful to be in the 1%. (laughs)

    5. MM

      (laughs)

    6. HS

      But my point-

    7. MM

      You've done a great job.

    8. HS

      No, but my point being, like, you know, I turned down Riverside, the platform we're on now, 'cause it's like $30, $40 to- to use every month. For- for a creator that makes $100, $200 a month, it's just too much.

    9. MM

      Yeah.

    10. HS

      And so are the majority of creator tools. And so you're tailoring yourself to the 1%, which is not a large enough market. And actually, there's very niche verticalized products for each, so there's little expansion opportunity. Why am I wrong and why should I be excited?

    11. MM

      I- I agree with you completely, um, a- about some of the challenges you just- you just mentioned with sort of creator tools. You know, I- uh, I- I recently had a conversation, uh, with Ben Thompson and we were talking a bit about this. And, you know, if you think about recommendation media and the shift to algorithms away from follower counts, right? Follower counts was where a lot of the value were- was accrued over the past, let's say, decade.... now you have all these creators, or let's call them influencers, on Instagram and, and platforms like these that effectively don't have control over their business model anymore, right? It used to be just, "Let's increase the follower count." Now they're kind of stranded. And so I think what this necessitates are tools and services that enable these creators, these influencers to build new types of business models. And so I think, um, having a direct relationship with the, the fan or the inf- or the, the customer ends up being much, much more valuable. And so I'm excited about platforms that enable influencers or creators to take control over their entire, uh, their entire business and not be reliant on algorithms and advertising that comes out of those algorithms to get paid because as we've seen now, Meta can just change their mind with a fl- with the flip of a switch and your followers don't mean anything anymore. Um, so I'm really bullish on tools like that. Um, the other thing I'll say is, and I think to your point, you know, there's a lot of talk about how Web3 will, uh, enable creators to increase their take rate because the platforms are, you know, the platforms are taking too much. I will be honest, I think this is the complete wrong problem to be solving right now. Um, I, I think to your point, we don't need to worry about the 1%. The 1%, like god bless them, they're able to make money. There are actually millions or tens of millions and maybe hundreds of millions of people that haven't e- yet even earned a dime. And so if we want to create a creator economy, right, economy implies like a very (laughs) large sustaining ecosystem of, of, um, of commerce and transaction and monetization. We need to worry about the millions or tens of millions, not the tiny 1% who are already making lots of money. So that's what I like to think about. I like to think about the tools to, to, to enable those creators.

    12. HS

      I, I totally agree with you in terms of the long tail and allowing that monetization they don't have. I think one interesting one is-

    13. MM

      And distribution. Sorry, and distribution.

    14. HS

      Well, so I, I either say, so whenever-

    15. MM

      Mm-hmm.

    16. HS

      ... I meet, like creator tools or anything in the creator economy, I say, "Hey, unless it does one of two things, I'm not interested." It either needs to make creators money or it needs to bring creators distribution. If it's not one or two-

    17. MM

      Totally.

    18. HS

      ... peace out, goodbye. Um-

    19. MM

      Yep.

    20. HS

      But w- but no, but I'm totally fucking wrong. I turned down Riverside. This, this company is fantastic, the product is amazing, what a mistake. I also turned down Descript, the editing tool which Andreessen did. Fire product. Now are either of these multi-billion dollar companies? I don't know. I use them daily-

    21. MM

      Well-

    22. HS

      ... and they're amazing.

    23. MM

      Well, the thing that I'll say about both of those companies, and I like them both, uh, a lot as well, I really like the products, I've used Riverside a bunch, I really like Descript, um, great teams, great founders, um, is they're different business models, right? So we're talking about, um, you know, w- we're talking about tools to enable like the long tail of creators. I think what these products are trying to do is, and this is my perspective, they're trying to be Adobe, right? And if you look at Adobe, Adobe's a really valuable business, right? If you can create really, really great tools and charge like a SaaS style, uh, subscription, you could have a pretty valuable business. (laughs) Now I think you need to do more than just like remote video recording and that's it, and I'm, in the case of Descript, you probably need to do more than just like text-based, um, audio editing, and I know they are doing a lot more. Um, but best-in-class tools for creators can be, it can be a pretty valuable business.

    24. HS

      I, I get you. My question is, so loving this. This like-

    25. MM

      Yeah, this is fun.

    26. HS

      ... uh, u- unbundling of Adobe is a fascinating one-

    27. MM

      Yeah.

    28. HS

      ... because you have absolutely right, like Riverside in one way, Descript's in another, you've got Canva now coming into a lot of that space. You have Figma obviously-

    29. MM

      Kapwing, Kapwing, Figma.

    30. HS

      Kapwing which-

  19. 40:52 – 41:48

    Adobe’s future

    1. HS

      like in different verticals. Uh, how do you think about the unbundling of Adobe, and is kind of their size and scale enough to keep the ship running?

    2. MM

      So I think it, I think it has to get unbundled and then rebundled again. Like I think one of these companies will successfully take a strong position in say video or audio editing, and they will, they will inev- inevitably need to ladder up into a new, you know, leverage that strength to ladder into a new, a new vertical, right, and take a step over in a new direction, and then hopefully establish a, a leadership position there, and then ladder into the new. I mean, that's how all of the best companies grow. They start as like one single... Amazon started as books, right? Then they take a step over (laughs) into, uh, AWS, right? And then they take a st- and then they take a step over into, you know, whatever, media, and before you know it, it, it looks nothing like it did in the early days of the product. And so I think the best companies in this, in this vector will need to do the same thing.

    3. HS

      I, I totally

  20. 41:48 – 43:15

    Twitter’s super follow fiasco

    1. HS

      agree with you. Can I ask, in terms of-

    2. MM

      Sure.

    3. HS

      ... uh, we, we said about, you know, building new relationships and having different business models, Twitter tried to do this with Super Follows and allowing-

    4. MM

      Yeah.

    5. HS

      ... you, your monetization of your Twitter followers. I saw Chris Messina, you know, kind of the famous Twitter, um-

    6. MM

      Yeah, of course.

    7. HS

      ... hashtag creator, and he said he was supposed to earn about $100,000 a year from his Twitter audience, and he ended up earning $36, um (laughs) which I thought was mildly entertaining, in, not in a nasty way but just like the inefficiency. Like how do you analyze that as a new channel and why it's broken down in many ways?

    8. MM

      I wonder if, and this is me just sort of like thinking in real time, um, but I wonder if maybe there's not enough differentiation in terms of the format or the content that gets delivered for the Super Followers versus just the regular followers.

    9. HS

      Mm-hmm.

    10. MM

      Um, we're talking about a 280 character piece of text. Um, I don't think there's a lot of precedent to suggest that that should be worth a subscription, right?

    11. HS

      Yeah.

    12. MM

      Um, I think there has been precedent to establish that, you know, maybe like a long form essay or a newsletter is valuable, but I don't know that...... Twitter has yet proven to consumers that tweets should be worth that. So, for me, just like, you know, thinking about this ... Again, thinking about this question in real time, I wonder if it has to do with the format.

    13. HS

      Can I ask you a question? It's that I

  21. 43:15 – 45:50

    Did Spotify miss out on social?

    1. HS

      think-

    2. MM

      Sure.

    3. HS

      ... Spotify is one of the best product, uh, companies in the world. I think it's got the best leadership team in the world. I'm so bullish on Spotify.

    4. MM

      Love Spotify. (laughs)

    5. HS

      Did they miss a-

    6. MM

      Obviously.

    7. HS

      Did they miss a trick on social? And just, I'm fascinated from the discussion we've just had, how would you apply that to Spotify and your lessons from being there for, you know, three or four years?

    8. MM

      Well, we just said that social is in some way commoditized, and so, you know, I think if Spotify were to have done this a couple of years ago, it maybe would have been the wrong bet. I- I think it would have been the wrong bet. However, if you think about where the future is headed, I think Spotify is in a great position to benefit from the shift to recommendation media, as we've been talking about. Spotify, you know, has been doing ML, machine learning-based content distribution and discovery, for a really long time. They did this very, very successfully with music. They arguably reinvented how all of us discover and listen to music through machine learning, and now they're doing something really interesting on the podcast side, in that they're making it really easy for anyone to create. And we talked about e- earlier how the best recommendation media platforms need an ocean of content to be able to program.

    9. HS

      Yep.

    10. MM

      And Spotify is effectively doing that. They bought Anchor, which, you know, obviously I'm biased. It's the company that I founded. But, um, Anchor enables many, many millions of people to create podcasts that never would have been able to create podcasts before, and so there's this huge long tail of- of podcasts emerging that didn't exist before. And, you know, they're- they're trying other things like, uh, I don't know if you saw- saw the test that they launched a few months ago, but they put a Podcast Create button in the actual Spotify app, removing yet another layer of friction to create a podcast. So you can imagine a world in which Spotify is enabling anyone to create, and they end up with a huge, huge, huge ocean of content through which they can program to their listeners based on trends in machine learning and their listening habits and things like that. And so I think Spotify is w- sort of ahead of the curve of this recommendation media thing. They're- they've sort of been doing it for a really long time, and I'm excited to see where they take it.

    11. HS

      Do you know what I- I think is the most underrated feature in Spotify? It's the Go To Radio when I'm on a song that I love.

    12. MM

      It's great. Great.

    13. HS

      I saw it on Twitter once, and I was like, "I've never done that before," and I fucking love it. It's brilliant.

    14. MM

      It's great. Yep.

    15. HS

      Um, but it's a product mistake that it's buried so deep.

    16. MM

      (laughs)

    17. HS

      I should speak to Gustav and Alex about this. (laughs)

    18. MM

      Yeah, you- I think you know those guys.

    19. HS

      Yeah, I know them really well.

    20. MM

      You should- you should reach out. (laughs)

    21. HS

      I- I- I've actually got both of them coming on the show soon, so I- I will ask-

    22. MM

      Oh, nice.

    23. HS

      ... directly. Um, I-

  22. 45:50 – 48:20

    Biggest takeaways from Angel Investing

    1. HS

      I do want to touch on your angel investing, 'cause I could talk to you all day.

    2. MM

      Sure.

    3. HS

      You- you made ... How many checks did you write as an angel?

    4. MM

      I've done about 50 so far, between-

    5. HS

      (laughs)

    6. MM

      ... uh, all the companies I've invested in and advised. It's- it's about 50 companies that I'm working with.

    7. HS

      Okay, so 50 investments as an angel. What have been your biggest takeaways from those 50, and how did it impact your mindset moving towards being a venture investor?

    8. MM

      So, I mean, I think ... (sighs) I wanted to build a portfolio. I- I learned from my days fundraising for Anchor about the power law dynamics of venture investing, and so it was really important to me from day one to actually build a portfolio and not just go, like, super, super deep a select few in just one area. And so if you look at my investments, you can see there- there are some common themes, but they're pretty well spread out. The other thing that I wanted to do was I wanted to be really consistent with how much I invested. Um, so- so I- so I wrote the same check size every single time, and the reason that I did this was, you know, I think you can get into a trap of altering the check size based on your conviction, but the reality is, like, at this stage, the angel stage, they're all super risky. (laughs) Like, regardless of your conviction, like, any of them could go to zero, and any of them could potentially blow up. And so I think ... Uh, what I felt was it was better to sort of, like, equal out the check sizes to give you more bullets in the chamber rather than try to predict which one has a higher success rate and doubling down. Um, that's kind of what- what my approach has been. And of course, like, you know, I- I've learned things over time, like, you know, there are certain categories that I'm- that I've become less interested in and other ones that I've become more interested in. But I think like anything else, it's just something you have to do a lot of to learn about it.

    9. HS

      I so- I'm so with you on the consistency of check size. It's one of the biggest mistakes that I see angels make. Did you ... When you started, did you set aside a certain amount that you wanted to invest?

    10. MM

      Sorry, amount in terms of check size or the number of?

    11. HS

      In- in terms of, like, you set aside, "Hey, I'm gonna put 500-"

    12. MM

      Oh, oh, did I set aside?

    13. HS

      "... dollars here."

    14. MM

      Sorry, did I set aside? Uh, no. Uh, I- I s- I- I- I left it pretty open-ended, uh, I will be honest, which, um, you know, uh, which, you know, my- my wife- my wife doesn't come from the world of technology and investing, so, uh, having that open-ended, uh, pool of capital to angel invest I think made her a little nervous at first, uh, which I totally understand. Um, but no, I didn't set aside an amount. I just- I just keep writing them.

    15. HS

      So

  23. 48:20 – 50:25

    Biggest investment mistake

    1. HS

      when you look back, um ... Everyone makes mistakes. It's nature of a portfolio. I look back at, uh, fund one in particular, 20VC fund one. Biggest mistake I made was one specific check went terribly wrong, um, very quickly, and it went terribly wrong, and I blame myself. I relied so heavily on someone else who knew the market so well and just said, "Harry, come in with me. This is a great, great opportunity," and I said, "Hey, man, let's do it." Um, I should have done my own work. (laughs) Um, what would you say your mistake was, and what did you learn from it?

    2. MM

      So I'll give you two. One is almost the exact thing you mentioned. Um, I, I'm somebody... You know, having been a founder, I really like to back founders that are super mission-driven, you know, they've experienced the problem personally, they wanna, like, be the change they, they wanna see in the world, you know, that whole thing. And, and those are the types of founders I like to back. Somebody who I really trust, and I still trust to this day, I don't hold this against this person-

    3. HS

      (laughs) .

    4. MM

      ... came to me and said, "Hey, there's this company, they're starting this, there's, they, they, they've modeled this out, you know, these guys have done this before." It's, it's basically what I like to think of as, like, a spreadsheet startup. Like, somebody, like, figured out the model for a startup and they gave the spreadsheet to a team that, you know, wasn't necessarily passionate about the problem and said, "Go build this." And, uh, and yeah, it, it was one of my early checks and it, it didn't work out, and, um, like I said, I don't, I don't hold the person... hold it against the person. But that was a mistake I made. Like, I, I think it taught me that I need to s-... I, I think I should stick to the mission-oriented founders. And then maybe another sort of, like, small, tactical, annoying, uh, thing, a mistake I made early on was that (laughs) I w-... a- in the early days of writing checks, I wasted my time and money on reviewing the legal docs. Like, I would hire lawyers and get them to review it, and then I, I pretty quickly learned that, like, these are all pretty standard docs and as a tiny check writer, I can't influence them anyway. And so (laughs) you just have to trust. If you're working with a lead that's, like, a major f-... a major fund or, like, a major law firm, like, you just trust them and you sign them. Don't waste tens of thousands of dollars on legal fees.

    5. HS

      Oh,

  24. 50:25 – 51:26

    How to determine mission oriented founders

    1. HS

      for sure. I, I totally agree.

    2. MM

      (laughs) .

    3. HS

      That was a terrible idea. Can I ask, you said mission-oriented there.

    4. MM

      Sure.

    5. HS

      Eve- everyone sells a great game, "I, I've got this, I've felt the pain in my old job, I've felt the pain in my pro-... I'm th-... I... this is my mission." It's not most of the time. How do you truly determine mission-oriented founders, do you think?

    6. MM

      I think you have to talk to them. Like, I think you really have to, like, know them. And, you know, maybe this is obvious, you have to do your reference checks, you have to do off-book reference checks. Like, you need to really get to, like, the heart and soul of the person. Um, yeah, you're right, it's really easy to just sell something, right? If you're a great storyteller you can just roll into a room and just, "This is my mission." Um, I like to really get to know the person, I like to spend a lot of time with them, I don't like to just quickly make decisions. Um, and yeah, the, the truth is sometimes you can get it wrong. You could find out that the person is f- full of shit.

    7. HS

      (laughs) .

    8. MM

      Um, but I think if you spend enough time with a person and you really try to know them on a personal level, you can really, you can, you

  25. 51:26 – 52:30

    Biggest miss

    1. MM

      can tease out whether or not it's genuine.

    2. HS

      I, th-... I agree. Final one.

    3. MM

      Sure.

    4. HS

      What was your biggest miss as an angel, and did it change how you think about it?

    5. MM

      My biggest miss. You're looking for the name of a company?

    6. HS

      Yeah.

    7. MM

      I really wanted to invest in OpenSea early on. Um, you know, this, this was, this was sort of, like, right, right up my wheelhouse, you know? I, I naturally am, you know, founding anchor, I'm a, I'm a big believer in, in platforms that lower the friction to enable people to create and distribute and monetize and things like that. And it was pretty clear, I think, at the beginning of this NFT craze that, like, OpenSea could be that sort of winner takes all that will, that would, that would do that for a new type of creator, a visual creator that could now monetize their work through NFTs. And so that was, that was one I didn't get to invest in and, uh, I, you know, I was bummed about that. I really liked the team as well. Um, but, you know, you li-... you live and you learn, right?

    8. HS

      Can I ask, s-... sorry, I'm just too into... We said about, kind of, the movement away from the social graph and the changing nature-

    9. MM

      Sure.

    10. HS

      ... of the social landscape. When we look at NFTs today, largely the dominant use cases around social capital, of having a CryptoPunk, you

  26. 52:30 – 55:50

    NFT social graphs

    1. HS

      name whatever, b-... ChainRun or whatever we wanna have, um, how does that kind of social capital associated to NFTs tie into a changing world of social and moving away from social graphs?

    2. MM

      So I actually... The reason I like, uh, OpenSea and NFTs is not because of what you just said.

    3. HS

      Mm-mm.

    4. MM

      I am not long-term bullish on the social capital aspect of the NFTs. Um, I'm more bullish on sort of the, uh, the creator-based use case of it. The reason I liked NFTs was because of, you know, you look at, you look at art. I'm just using art as one use case, but you could apply NFTs to a number of different use cases. You look at art and you see that there are naturally tons of people in the world who are making art, but it's really hard to monetize, right? If you're not a great artist or you don't, you know, you're not great at, uh, rubbing elbows with people in your local art community and getting in with galleries and things like that, it's really, really hard to monetize your art. And you couldn't monetize your art on the internet before NFTs came along, you couldn't just, you know, take one of your paintings or your drawings or your digital art and put it up on the internet and monetize it. NFTs, um, maybe as a bri-... byproduct, 'cause maybe it is more about what you're saying, enabled artists who had never been able to monetize their work to all of a sudden have a very willing, uh, potential customer base that might be willing to pay them a lots of, lots of money for their, for their work. You know, I have this friend John, John Januzzi, and, uh, you know, he's been an artist his whole life. I, I didn't... actually didn't even know this about him. He went to school for fine art, you know, he got a job at, um, in, uh, fashion and, and he actually worked at Twitter for a while. But on the side, he's always been a passionate artist and just never did anything with it. When NFTs comes along, he creates this collection of art, um, and he puts it up and, like, overnight he's, you know, he's generating hundreds of thousands of dollars, he's giving half of it away to charity, and all of a sudden he's motivated to create. And so that's the aspect of NFTs I really like. I like the, the, the ability to empower creators. I'm personally less bullish on the social capital, you know, "Look at my Bored Ape, I'm so special," uh, uh, component.

    5. HS

      Wh- why-

    6. MM

      'Cause I think that's not truly scalable.

    7. HS

      W- why do people buy his art?

    8. MM

      Um, 'cause, uh, well, I think some of them bought it 'cause they like him, some of them bought it, yeah, because of the social capital. Um, some of them wanted to get in early and speculate, which is also something I...I guess that does go hand in hand with art in some way. But it's not the reason... It's not the thing that excites me about NFTs, I guess is what I'm saying. I think the thing that excites me is the democratization for the creator side.

    9. HS

      I get you. Um...

    10. MM

      Yeah.

    11. HS

      Yeah, I'm not so bullish. Web3?

    12. MM

      (laughs)

    13. HS

      Web3, no, no. Web2's fine, I like Web2, you know? But-

    14. MM

      I like Web2 as well. I, you know, I built a, I built a platform-

    15. HS

      (laughs)

    16. MM

      You know, I worked at Spotify for many years. Um-

    17. HS

      Right.

    18. MM

      I think Web3 can make sense for certain use cases, but I don't view it as a panacea for everything.

    19. HS

      Finally.

    20. MM

      That said, you know, I, I believe in infrastructure and, and, and that's another thing that Lightspeed's doing that I'm excited about. You know, they, they've been investing in crypto and Web3 for a while, and I do think it'll be an important component of the internet. And so... But I don't know that anyone can predict the specific use cases today. And so I think the better bets on, are on things like

  27. 55:50 – 58:05

    Opensea’s future

    1. MM

      infrastructure.

    2. HS

      I totally agree with you on the infrastructure play and kind of betting there. A final one. OpenSea obviously facilitates buying and selling NFTs, um, I think they reported $5 million in transactions over a certain time period, and it was $485 million in the peak of the boom. Wha- what happens to OpenSea in such volatile markets, both in terms of crypto and NFT obviously, 'cause the price of Ethereum dictates a lot of the transactions? What happens to OpenSea when seemingly, I mean, hype cycles, it is not immortal from?

    3. MM

      So, like we talked about at the beginning of the conversation, they, you know, they were throwing off crazy revenue a year ago or whatever it was. But like I learned with Anchor, like these moments can be fleeting and this is a marathon, not a sprint. The game's not over. I think, as I'm sure they're doing 'cause they're, you know, smart teams, smart founders, I'm sure they're, they're, they're, they're back at work, you know, trying to think about the next five years of the product, not what happened last year and I think the best teams, um, will recognize that it's a long-term game and maybe the worst teams will fizzle out and try to grasp onto the thing that worked a year ago but maybe isn't working today.

    4. HS

      It goes back to our question on market versus founder and actually, you know, OpenSea as a company cannot will a market into existence, I don't think.

    5. MM

      Yeah.

    6. HS

      Do you know what I mean?

    7. MM

      I do. I do. I think, um, you know, we, um, with Anchor, you know, you, you, you acknowledged that we sort of pivoted. I think it was a really important lesson to learn and I, and I talk about this with teams sometimes that I work with, that at a certain point you have to stop trying to get the world to want what you want it to want-

    8. HS

      Mm-hmm.

    9. MM

      And you need to give it what it, what it needs and what you're uniquely positioned to give it. Now fortunately with Anchor, we found ourselves in a position where we recognized that people just really wanted to make podcasts and they wanted it to be easier, and the stuff we had built could be retrofitted to do that, like perfectly. So that's great. Um, but you can't really, you can't really force the world to sort of buy what you're selling, I guess if, if, if, if, uh, maybe that's another way to put it.

    10. HS

      I totally agree. It's like venture, you can't force the founder to take your money, sadly.

  28. 58:05 – 58:52

    Favorite book and why

    1. HS

      Um-

    2. MM

      (laughs)

    3. HS

      (laughs) Uh, listen Mike, I love this. I want to move into a quick fire round, so I say a short question.

    4. MM

      Sure, let's do it.

    5. HS

      So what's your favorite book and why?

    6. MM

      Ooh, I have lots, but maybe I'll just say that, um, right now I'm reading the first Harry Potter to my six year old daughter and we are loving it. And I had never read Harry Potter before, uh, and I'm having a blast right now with all like the character development and stuff. It's, uh, I'm like 20 years late on this.

    7. HS

      How did becoming a father change you?

    8. MM

      So when you become a parent, um, you, you think, especially as a founder, you think it's actually gonna make your job way harder, but it's actually the opposite. It helps you to focus. It really snaps into focus what's important in life and helps you prioritize your time just way, way better. Um, so I think, uh, it

  29. 58:52 – 59:53

    Secret to a successful marriage

    1. MM

      teaches you about the priorities that you should be, uh, valuing in your life.

    2. HS

      What is the secret to a successful marriage?

    3. MM

      Mm, good one. So, I think this could apply to marriage but also lots of other important relationships like, you know, great friends or maybe a co-founder or a partner, and that is, um, listening, not just always trying to fix, right? I think... I'm a builder, um, and so naturally like I always want to fix everything, but I think what I've learned as I've gotten older and, you know, I've been with my wife now for, you know, 15, 17 years er- since we first started dating, whatever it is, and I've learned a lot over time, relationships are built on listening and actually like empathizing, not on action. I mean, obviously action is important as well but I think like sometimes people just want to be heard, and you really need to listen and stop trying to make everything about you and about what you can do to fix a situation, and you really just need to listen and hear people. And so I, I think that's the key.

    4. HS

      I totally agree actually. Harley, um, president of Shopify

  30. 59:53 – 1:00:33

    Most underrated angel

    1. HS

      said exactly the same, so-

    2. MM

      Oh, really? (laughs)

    3. HS

      Yeah, exactly the same.

    4. MM

      Whoops.

    5. HS

      Um, what's the most-

    6. MM

      (laughs)

    7. HS

      Who's the most underrated agent in the ecosystem and why?

    8. MM

      Uh, Maya Prohovnik, she was the first employee at Anchor, she now runs Talk at Spotify. Um, she's amazing because I think she is probably the most empathetic product leader I know. She knows better than anyone else I've ever met in my life what will resonate with users and what won't. And so, you know, if, um... I, I, I told you earlier on I really like to be this like zero to one type investor. She's also really, really great at that. She, she just knows what will resonate with people. She has a great ability to put herself in their shoes.

  31. 1:00:33 – 1:01:19

    Biggest strength and weakness

    1. MM

    2. HS

      I would love an intro to her, she sounds fantastic.

    3. MM

      You got it. You got it.

    4. HS

      Um, uh, tell me, what's your biggest strength and your biggest weakness?

    5. MM

      It's probably the same answer to both. (laughs)

    6. HS

      (laughs)

    7. MM

      Uh, I have a tendency to become extremely passionate about things, like a- about what I'm working on, what I'm interested in, I really pour my whole self and my heart and soul into things, and it becomes my mission. Now that's obviously a strength because then I get, I s- I can get like really good at that thing, and I can become like the expert at the thing.But it's also a weakness because other aspects of my life can then suffer as a result, right? I just, I, I go all in on something and then everything else has a tendency to get blocked out.

    8. HS

      Someone told me-

    9. MM

      And uh, you know, look ... What's that?

    10. HS

      Someone told me once, a wise, wise elder, that when you're winning at work, you're losing at home. And when you're winning at home-

    11. MM

      It's totally

  32. 1:01:19 – 1:01:55

    What would you most like to change about startups

    1. MM

      true. (laughs)

    2. HS

      ... you lose at home. I, yeah, I do-

    3. MM

      Yeah.

    4. HS

      ... feel that one too. Um.

    5. MM

      Yeah.

    6. HS

      Tell me, what would you most like to change about the world of startups?

    7. MM

      So, we talked about a lot in this conversation how I really like products that lower the friction for people to create things. Um, I, I think that I'm always excited about things that make it easier for people to start companies, right? Like I, I want, I want the friction to drop even lower. Um, it was such, for me, an absolutely life-changing experience to be able to start a company and build a product, and, and so I really love products and, and tools and services that help founders, uh, lower the barriers even more. And I'm, I've

  33. 1:01:55 – 1:05:15

    Most recent angel investment

    1. MM

      made a couple of investments in this space.

    2. HS

      Listen, final one. What's the most recent angel investment, and why did you say yes and get so excited?

    3. MM

      Hmm. Um, I recently invested in a company called Stardust. It's a women's, uh, women's health product, uh, first focused on period tracking, secure, end-to-end encrypted, privacy-centric. Um, amazing founder, amazing female founder, mission-driven, and you know, I think a couple of things. First of all, like I said early, I'm just really drawn to really strong, mission-driven leaders, um, and people that really know what they wanna build. And, and, uh, and so for that reason, I was really drawn to this company. But you know, I think it matched a theme that, that I see happening, which is, I think encryption is becoming a really important consumer-centric feature. Unfortunately, it's happening for somewhat cynical reasons, right? I mean, I think there's a, it's clear that mistrust of institutions is, is only going up.

    4. HS

      Mm-hmm.

    5. MM

      And I think this is going to force people and users to seek much, much more control over their data and their privacy, and I think the founder, uh, of, of Stardust had this insight as well. And, um, and you know, shortly after I committed, sure enough, she, I mean, she was right. I mean, again, sin- this is, this is not necessarily for a good reason. This is actually for a very, very bad reason. Roe v. Wade was overturned shortly after. Um, horrible thing, and you know, something, uh, that I think is a real, uh, a real travesty here in the United States. And uh, and almost immediately, you know, she saw that tons of people were sort of flocking to these new women's health apps that were really, uh, privacy-centric and encrypted and end-to-end, because they now were worried that their privacy and their data may be taken advantage of, um, by these big platforms, uh, for reasons that the users weren't comfortable with. So, uh, that's an example of a recent investment.

    6. HS

      Why has no one built a big business in this market? Everyone's been going after period tracking for years. Clue in Germany been doing it for years. I, I'm sorry. I'm being ... Uh, pretend we're in a partnership. Why-

    7. MM

      Yeah.

    8. HS

      Why has no one gone, why has no one gone big? It's a strategic acquisition for any big European healthcare buy insurance provider. There's not a $10 billion company here.

    9. MM

      So, I think that, um, we talked earlier about how there's sort of like this bundling and unbundling that happens. I think, you know, you t- you asked about why hasn't there been a big period tracking app. I actually view it more as, uh, a health product and a health service, and I think period tracking is one potential vertical for a company, uh, to really establish a great product. But in order to build, you know, a $10 or $20 billion business, that business then needs to ladder into new categories and new verticals, establish strength in that vertical, and then again, ladder up into the new strength and, uh, or the new vertical and establish strength there. And so, I, I view it more as, um, one offering in a suite of, um, of health products and services, and obviously there have been countless massive, massive health businesses.

    10. HS

      Mike, I've loved this. Uh, it's been such a natural discussion. It's not followed our schedule at all. (laughs)

    11. MM

      No.

    12. HS

      But uh, it's been a joy to have you back on the show. I'm so excited for your time ahead with Lightspeed, and thank you for joining me.

    13. MM

      Thank you for having me, Harry. It's been a blast, as always.

    14. HS

      Man, you are a hero.

Episode duration: 1:05:20

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