How to launch and grow your product | Ryan Hoover of Product Hunt and Weekend Fund

0:00

don't know how to articulate that feeling but that flutter in your stomach that you wake up with in the morning of just anxiety and stress and and worry being a ceo or founder makes it slightly harder in some ways because you still have to put on this mask you have to put on the space of

0:15

confidence externally and internally as well where people need to trust you you also don't want to subject them to the same anxiety that you're feeling and be 100 transparent ryan hoover is the founder of product hunt which you already know he's also a former product manager which i did not know

0:37

currently he's a full-time investor with his fund the weekend fund he's also an author of a bunch of great blog posts and an actual book all hooked he's also really good on twitter and in my opinion a very special human being brian hoover welcome to the podcast hey lenny thanks for having me i've been

0:54

reading a lot of your blog posts over i don't know past two or three years now and i'm glad to see you do the podcast now it's cool thank you man that compliment will go straight to my heart and i will think about it often i appreciate that and put it on twitter there you go yeah that's the

1:09

clip we're done this episode is brought to you by revenue cap revenue cap makes it easy to build analyze and grow in-app subscriptions on ios android and the web their platform lets you focus on growth rather than getting bogged down in subscription infrastructure revenue cap

1:30

provides a back-end and wrapper around apple store kit and google play billing to handle the implementation and upkeep of in-app purchases revenue cad is your source of truth for customer status across platforms and provides out-of-the-box analytics for key subscription metrics like monthly

1:46

recurring revenue lifetime value retention and more with revenuecat you also get pre-built integrations with best-in-class tools like amplitude apps flyer and firebase that means reliable consistent data sync to your entire product and growth stack in minutes cy companies like notion vsco

2:05

and life360 use revenue cap to power in-app subscriptions learn more at revenuecat.com hey ashley head of marketing at flat file how many b2b sas companies would you estimate need to import csv files from their customers at least forty percent and how many of them screw that up and what happens when

2:25

they do well based on our data about a third of people will consider switching to another company after just one bad experience during onboarding so if your csv importer doesn't work right which is super common considering customer files are chock full of unexpected data and formatting

2:43

they'll leave i am zero percent surprised to hear that i've consistently seen that improving onboarding is one of the highest leverage opportunities for both sign up conversion and increasing long-term retention getting people to your aha moment more quickly and reliably is so incredibly important

3:00

totally it's incredible to see how our customers like square spotify and zora are able to grow their businesses on top of flat file it's because flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster if you'd like to learn more or get

3:18

started check out flat file and flat file dot com slash lenny you're such a tech celebrity everybody knows product hunt everybody knows ryan hoover at least in tech and i'm curious how often are you recognized walking down the street in life and has there ever been like a super awkward or super

3:35

hilarious moment of that yeah so product ten started in late 2013 and quickly got a lot of traction in the tech tech sphere so yeah people in tech might recognize me people ask and attack doubt doubt they recognize me um i actually do wonder subconsciously if i grew my hair out to avoid being recognized i'm not

3:53

sure if that's true or not but anyway it's been a couple years or so growing my hair out and like i just kind of want to like disappear sometimes but you know in san francisco where everybody's in tech there's a lot of that and probably the the the moment where i was like oh this is

4:09

this is like a thing um it was probably early product on and i was at do you remember i don't know if you know this do you know a club um called dna lounge and they did something called booty every saturday it was like a matchup dance party yeah super well known in the bay area

4:24

really fun fun uh kind of experience anyway i remember being with friends and drinking like like one does and somebody turns around and says is that the product guy that was the first time that sort of happened in that setting where i was like oh gosh now i have to like think about my actions and i can't just

4:41

like be entirely like loose and you know relax in my friends and um so anyway there's always pros and cons and those types of things um but you know it it definitely is makes you more aware of i'm already very like sometimes anxious and like self-aware person in terms of like my surroundings

4:58

and so when you combine that with these strangers might be watching me is not the best thing in the world but it's okay i've actually gotten a little bit through that same experience recently in like a much smaller sense where with this newsletter and the growth of this thing there's meetups happening all over

5:12

the world and so i've been going to the sf meetups here and there and it feels very strange to be like known and people get they're like taking pictures of like what the hell is going on because i started this thing as the covet hit and it was like everyone's at home i was just typing on

5:26

my computer they have to go anywhere and as the world has emerged it's becoming new and you think i'm dealing with on a much smaller scale yeah yeah events are events are fun um we threw a bunch of them at product and uh yeah you do a lot of selfies and a lot of like handshakes and it's there's

5:44

there's some energy there i'm an introvert though so by hour like three or four i'm just like uh i need to use the restroom because i haven't been able to escape and i'm socially exhausted so but they are fun i know uh exactly what you mean i am also an introvert and i

5:59

get so drained doing things like that i was gonna ask you about that so yeah um along the same lines you're you're very public person you tweet a lot you share a lot you do a lot of podcasts and things like that what's something that people don't know about you yeah um you're right i probably should

6:15

maybe overshare uh on twitter and other things no that is not there is a list of there's also a whole series of things that i don't talk about um some of them well anyway i won't i won't talk about the things i can't talk about uh but one thing that um one thing that most people

6:31

don't know about i know there's certain juicy things like everybody has in their life um i recently moved to well i guess been a year i moved to miami about a year ago and i haven't been talking about it publicly primarily because i just didn't want to be lumped into oh another person moving to miami like i

6:49

don't know i just there's no benefit or like reason for me to do so i want my friends there in miami to know i'm there but otherwise i don't need the world to know i guess now they will um that said in miami you know we're we're there about two-thirds of the year so i'm actually in california right now um as

7:05

you know the summer humidity come comes through miami and hurricane season we're planning to do more of um i wouldn't call it nomadic and i wouldn't call it by coastal per se but something like that where two thirds of the year were miami and then maybe a third were in new york or la or

7:21

someplace else and i love that um fortunately we have the flexibility when i say we my girlfriend susie and i to just carry our laptops and work anywhere so it's been it's been a nice lifestyle kind of shift i did not know that that is very interesting why did you get pulled into miami what pulls you there

7:40

yeah you know um so the way i describe city cities are kind of like a product so if you're in a supermarket or a supermarket i sound like an old old person uh if you're at a store you're looking at different products if you're online you're evaluating different products and they each have like a cost

7:55

and they have some benefits or values or whatever you want to use to describe it and for me each city is kind of like that and so you know in terms of cost there's cost of living in terms of housing uh food taxes a bunch of things that go into the cost of living in the city and the city provides a lot of

8:11

benefits and and things like that so in l.a so i was in bay area for 10 years la for two miami for one now they each have their own pros and cons they each cost respectively different prices and so we visited miami a year and a half ago and we just fell in love with a lot lots of

8:29

it um we also it's just cheaper it's cheaper than the bay area it's cheaper than la um when you kind of counter counting all in costs um we had a bunch of friends moved there so we enjoyed the city we're like this is good strong roi uh this is a good product let's let's move there um but at the same time as i

8:47

mentioned like we are traveling and exploring other cities so it's kind of the best of both worlds for us very cool um curious how long you last there and how you like it over time i love miami i always have a good time when i go there and i have many friends living there

9:02

changing topics a little bit something that i've noticed you do recently which is super cool is you offer people the chance to dm you questions that they have about their startup or their journey as a founder and you just offer to give them free advice and then sometimes you tweet the

9:17

dms to share that with more folks i'm curious just how many people have dmd because this is such a cool offer and what have you learned going through this and kind of hearing people's questions i first opened up my dms i had them close which is like traditionally the default on twitter for a long time because i was

9:31

like oh if i open them up i'll just get a bunch of spam and i don't need another inbox to cull through i opened it up quietly and i actually didn't get a lot of spam uh surprisingly yeah people would chill something or promote something but it wasn't too bad sorry i

9:45

left it open and then i forget one day i was maybe i was like on the elliptical bike or the recumbent bike or something and i was just like i tend to get on the bike and just hold my phone up and just do emails and work and so um i just said hey dm me if you have the question any founders and i'll try and

10:01

like answer as many as i can and um part of my motivation for that was i don't know i was just killing time and the other was i used to blog a lot i used to write a lot um i've written hundreds of blog posts but not so much anymore i really write anymore and part of it's because it just takes

10:17

so long to write and sometimes i don't feel like inspired by any topic it's sort of like a writer's block and so i found this also kind of as a means to like do micro almost like micro blog posts in a way where the prompt is the question from somebody else i don't have to think about the prompt

10:34

and then the answer is is in some ways a way for me to actually think about that that topic almost like refine my own thinking in some sense and so i started doing that and i realized well maybe other people have similar questions and maybe other people have other answers and other ideas too so

10:51

i would just take a screenshot of my answer and kind of summarize their answer of course keeping anonymous not sharing anything that would be sensitive um i just put it on twitter and you know it's been fun i do that maybe once every three or four days i share a new question and answer and sort of like

11:07

a it's like micro blogging in a way i guess that's what twitter is but like it's kind of like a real micro blogging kind of like uh um activity for me is there anything that's kind of surprised you or that you've learned from founders but they ask you about like wow i didn't expect this was gonna

11:22

be such a common problem or question i would say anything like super surprising however a lot of people so you can do the same thing on twitter and say hey ama ask me anything in public the thing is people are not going to ask certain things for a lot of reasons and maybe

11:35

the biggest surprise was a lot of people pretty vulnerable these are strangers founders who dm me saying hey i'm we have three months runway left we're running out of money here's the situation what advice do you have or just things that you know everyone has to wear this unfortunate mask is kind of

11:50

the way i what i use to describe it this mask in life and business where everything is going great and you know you're super confident they're no problems you got it all under control and so the reality is that's not the case like if you appeared inside of almost every single company it

12:05

probably looks chaotic in different ways and so i guess i guess maybe the biggest surprise or thing that i value the most is the authenticity of people willing to share some of these vulnerable moments and questions awesome what's interesting about your format is as you were talking i kind of

12:20

realized it's very similar to my newsletter format which i which i think is part of the reason it worked is it's based on people asking me a question and then i answer the question yeah that's true and that ends up forcing you to have like concrete actionable advice so you've kind of developed an even more

12:34

interesting way of doing it on twitter where it's more focused so very smart i've always liked your format by the way in that you're um you're a curator in many sense like yeah you have a lot of experience and good ideas but you're not trying to answer all the questions and

12:49

that you're really pulling in experts in their domain expertise to like find answers or inspiration and i've always liked that format because one it i think leads to better better results better content better answers but also it's arguably easier um like imagine if if you tried to like write well

13:09

you're shaking your head almost like if i had the answers i'd be like oh here you go i'm done you know the research takes a lot of work and time but but i do agree it ends up being a lot more useful and and valuable and the reason i did that just to kind of explain that briefly is when i left airbnb people

13:24

kept coming to me and asking me like hey how did airbnb do this thing how'd they do that thing and i was just like like they don't know what they're doing they just did this thing and who knows if that was the thing that helped them or if that was the right way of approaching

13:35

it so i wanted to do this like what does everyone do and what seems to be the pattern of the thing that works and that kind of led to this approach and it takes a lot of time especially this new series that we're going to chat a bit about that i worked on where it's just like endless interviews and chats and

13:50

researches and watching interviews but yeah it works out yeah yeah you you and how many hours actually you put into like a typical essay oh a reverse question uh i would say the media asking questions but i'm curious band no it's cool i say i'd say the uh median post is about 10 hours so it's

14:11

like maybe i kind of work out through the week so maybe like a few days through the week but the most epic posts take hundreds and hundreds of hours that i kind of work on behind the scenes as i work on the weekly posts so there's a wide range some posts take like three hours and sometimes those do

14:28

very well much better than i expected yeah yeah that's exactly going back to my my point about like it takes a long time to write content that you're proud of i'm also just very particular about words for better or worse and so i the first draft actually is maybe like

14:43

20 or 30 percent of the time and then the rest is refining and getting feedback and everything else that's exactly how i find it question i want to ask is startups are so freaking hard they almost always fail it's always just like oh my god this is why am i doing this to myself my general

14:59

advice to founders is like don't start a company unless you just like can't not start a company because it's so hard what's your take there what do you think what do you advise founders for when they're thinking about should i start a company should i not start a company which how should i approach this

15:15

yeah i do i do spend time ironically like challenging founders sometimes when they're thinking about raising or thinking about an idea to to not raise i think people who are in tech especially are certain bubbles of tech that's the default it's like the first thing i do i

15:30

have an idea now let's go raise money and we've gone through some like pretty massive bull cycles where that that was possible for a lot of people but it's a huge decision so with products and it was a side project in the beginning it wasn't actually intended to be a startup at all but in the beginning

15:47

you know it was a newsletter and it was a website and it was about four to five months before we even incorporated and we got a lot of traction so it was during that time i was really just thoughtful around like should we raise um do i want to work on this for many many years what's the opportunity is this

16:04

even a venture-backable like idea like all those questions were circulating in my mind for a while and this was also in a time when the market was pretty was similarly bullish this is uh end of 2013 early 2014 and investors were were using products and to reach out to me they was recording courting me and

16:23

um kind of doing that little song and dance to invest but i i just wasn't sure if i wanted to and so i don't know i think a lot of those decisions are very personal and contextual however i think it's super important that founders see a line of sight to work on this for

16:39

i think my rule of thumb is a decade just do you see yourself working on this for a decade and maybe it's not a decade that you actually work on it it probably won't it it'll probably fail before then as most startups do but i think it's a good litmus test for yourself to be like do i actually care

16:52

about this enough and am i really stoked to work on this for many many years but then you know the other thing is i think a lot of people also think i need to start a company i need to start a startup and they skip to that step without just tinkering and building and you know products that we called it not

17:09

even a side project we call it an experiment and that framing i think is for me has always been helpful because it's an experiment is really not about success of course you want it to be successful but the goal is not success i put that in quotes it's really to learn and you know see if people want

17:25

this thing and then kind of adapt and so like an experimental mindset is helpful and i think a valuable way to start it even goes back to like why writing the fun weekend fun it's like what are you tinkering with on the weekends you know and how can you be more curious and

17:40

experimental and kind of your exploration of new startup ideas i didn't know that's why it was called the weekend fun i thought it's because you worked on it on the weekends or is it both it had like multiple meetings yeah it was three meetings one was was that i started weekend fun when i was building

17:56

product hunt so took a lot of pitch pitches and calls with founders on the weekends um two i think a lot of great ideas start by like metaphorically speaking nights and weekends um kind of side projects or ideation and then the third reason was it was like more friendly i don't know i didn't

18:11

want to name it hoover capital or something like sterile wanted to be wait that's an awesome name hoover capital wow we were capital all right i don't know i if you well yeah it's not on brand oh but yeah yeah as you know asked people on twitter what questions they would want to ask you and

18:32

so i'm gonna inter-splice these questions as we go through this and you just touched on product hunt and fundraising and i'm curious if you were to go back and and do it again would you raise money for product hunt or would you not great question so at the time this is also the thing i asked founders

18:49

is why do you need to raise money like what is it for and surprisingly some people like i don't know like they don't have a clear answer for me it was pretty obvious like we needed we needed to hire we needed people like i didn't have personal capital to to pay people there was an alternative uh

19:06

reality where we actually built it open source i was thinking like is that possible like we're building something for the tech community i'm sure a lot of people would love to work on this could we build it in an open source way but that like that's really hard to do and when

19:21

you're building a company you probably don't want to innovate on too many things um including like essentially how to build a product and build a team so anyway to answer your question if i i don't i don't know at the right at the time raising money was the right decision because i i wanted to hire and

19:38

i didn't have personal capital there really weren't any other realistic options i don't think today i could get further with my own i'm not super wealthy and i'm super illiquid but i have at least enough money where i could have funded you know maybe a year of development with this very small team

19:52

so today it might be a little bit different in which i might not raise venture capital because production isn't the type of company that needs to raise a ton of money it's also one which is not um doesn't have like direct competitors in the sense of like an uber and lyft situation where raising is actually like

20:08

kind of mandatory and you sort of have to build a massive war chest to compete so there is a scenario where if i had more money then maybe i went to raise venture capital but yeah there's a lot of other like decisions and other things that probably uh bigger mistakes i think i made um

20:25

not that raising the money was a mistake by any means i was living the right decision that but there's a lot of learnings in hindsight's 2020. the point you made about like you just needed money to like run the thing i think that's so overlooked when people bash the idea of fundraising for a

20:39

startup that maybe didn't need to like you just need money like you don't have just money to burn and go into debt that makes sense to raise some money and see where this thing goes without really knowing where it's going to go yeah especially if it's i mean i think it's very important to raise

20:56

raise from people who are aligned with you too meaning like why does this person want to whether it's an angel or fun invest in your fund sorry not fun your company when you go down a certain path when you raise a series a b c like you have different expectations when you raise your precede or seed

21:14

round so i think also understanding like you know what you're signing up for is super important what kind of treadmill you're you're getting on yes yeah because you can't get off i mean you can but it's not like a company i always say like when you're at a company you put in two weeks notice

21:28

one month notice you can move on as a founder or ceo you can't like you really can't um now you technically can but you can't it's really hard to exit yeah i look at the airbnb founders who've been doing this for 15 years and like you know they're doing well in life but they also it's very

21:48

hard to leave yeah coming back to product hunt people launch their products on product hunt that's the thing and i'm curious founders are always so obsessed with launching and the power of a launch and we gotta launch do you think launches are worth it for a company is that something founders

22:05

should be spending time on or is it often better just to not even spend time on that and just build slowly yeah i i always kind of whenever i share like my perspective on stuff i i unfortunately always always like it kind of depends which is kind of like sounds like a cop-out answer so it's more my

22:19

answers are usually more new lost and the thing about launching is is going back to why are you raising money what's the goal same thing why are you launching and a lot of people default to things like customer acquisition oh i want to acquire customers but sometimes that's actually not it's not

22:35

useful launch sometimes doesn't help with that but there are many other reasons why you might want to launch so customer acquisition is one to get the word out now there can be recruiting so by you know sharing your story getting people excited it might make it easier to recruit and get people excited about

22:50

you know what you're building another is fundraising sometimes it can create momentum you know as other investors they do read the news and they know that you know when this company is more public there might be more heat around a particular deal feedback is one um feedback from users feedback just

23:07

serendipitously and and sort of another one is partnership so as you launch you might also encounter more partnerships more opportunities i think there's a serendipitous effect of watching so i think understanding like what are the priorities in the business like if you

23:21

it might not be customer acquisition at all it might be we need to recruit and hire let's launch so we can get the word out hopefully that will help land you know our next you know engineers designers or whoever and then i also say there's like these little side benefits too of launching um

23:35

that we see a lot through product hunt one of them is team morale and this this might i think this is overlooked and i i would also encourage founders not to get their team to um i would say you shouldn't be motivated to launch a product just to get like the likes on twitter and the votes and prototype but

23:54

there is a like a powerful team morale and kind of building moment there where you can all celebrate what you've accomplished and what you built and put it out to the world and you know somebody on the team could share you know the the the products at launch or you know some techcrunch article with

24:09

their their mom and you know like that seems like a trivial kind of meaningless thing but actually matters for a lot of people and then the other thing is seo so seo is like a part of your strategy having articles positive articles having a positive product at launch things like that can also be helpful

24:25

that's awesome i love that last point about morale i hadn't thought about that you've seen probably more launches than any person out there how many launches of startups would you estimate you've kind of like seen or been i don't know an observer of if that makes any sense

24:42

i should look at our database on product and see how many launches we've had because it's going to be a subset of that i mean by seeing uh some of it's very high level with tens of thousands over the years okay so when you think about that do you have any sense of what correlates with a great launch

24:59

versus just like an okay launch would it what if founders miss with how they launch yeah i mean this goes back to college and the you know i won't go on my own rant about education but you know english class and writing class a lot of teachers teach people to write with big words and fill pages of content

25:18

and basically not speak like a human and so one one thing i've noticed among founders and just people in general is they tend to write like a pr person and not like a human and not like you know the the way that i kind of describe kind of a frame of writing maybe your tagline

25:34

for product time um or for your launch in general is like how do your customers or your users describe your product to other people or another frame is how do you describe it to your friends like when you're just you know hanging out like how do you describe what you do what you built what it's for

25:49

and that language i think resonates with people because it feels way more authentic and the people that use buzzwords and and vague language it just doesn't click people see right people are sick of the pr speech and so i think the language and the microcopy copywriting matters so much

26:06

and then there's a lot of other things around like we should go more to the product and less about the launch like do you really understand who you're building for and do you understand how to communicate the value prop like where does fit in the mind of the user there's sort of a lot of um i guess more

26:22

strategic kind of like decisions that go into to that uh before the launch imagine each of those uh points can be its own podcast and blog post one of the questions that people asked me on twitter was the classic how do i get to number one on prodcunt so my question to you is i

26:39

know that's like there's not gonna be a silver bullet is there like a guide that you point people to that's like here just follow this advice and or i don't know two or three keep things that you just gotta get right yeah yeah so we um in the post mode there's actually a link links to a bunch

26:54

of guides and faqs and things like that so it's really easy to find like sort of the best practices there the team also has like this checklist so once you launch there's like a checklist of things recommendations or tips and i'm actually forgetting like what each of them are specifically right now but some of the

27:10

things that i've noticed that make a big difference is we've already talked about the tagline copy that goes to not only the post but also the maker usually people tend to add like some introduction some contacts uh generally a lot of people will they manufacture pr speak there too and

27:28

so speaking more like a human i think is important also keeping it a little brief some people write essays which might be interesting but the reality is most consumers especially people on product you know they're slipping through a bunch of ideas they're looking for things that spark their curiosity and

27:41

interest and they're probably not particularly interested in reading like an essay you know from from the maker so keeping that short i think is helpful and then another big one is the gallery is is often the first thing that someone is going to see once they land on the page and so just naturally our eyes

27:58

gravitate towards visuals and some of the most interesting presentations i've seen is people use the gallery almost like a slideshow like telling a story where each slide is is communicating like a different well a story of some sort it could be like here's the before and after with

28:14

our product or here's the evolution of what this product can do there's many different ways to approach it but like a very clean you know visually interesting story um can also be a great way to like capture people's interest in what you built awesome that was very tactical and

28:29

helpful if you were to launch something on product hunt yourself and it wasn't like hunted by ryan hoover do you think you would get to the top yeah i mean i don't know it's it's funny because if you we should do some like historical analysis on prototype because i'd be curious to know the actual numbers but

28:46

it varies all over the board so some people they ask me hey like i don't know is production like do b2b companies do well there and i'm like yeah like probably more b2b companies than b2c companies actually and so you see you know seemingly boring companies that tap into something that that that uh

29:06

people find useful or resonance resonates with them um can go to the top and then you also see the weird wacky stuff you know the silly apps also hit the top so i don't know it really varies and sometimes it's also driven by like the almost like the zeitgeist like what do

29:22

people find interesting right now like what's sparking people's interest because product on on one side you are potentially attracting people who might be future users and customers partners and so on but it's also just a general kind of like side guise of the early adopter tech community like what are

29:37

they interested in what do they find compelling in general got it okay so i have a bunch of questions from twitter that people wanted to ask you and so let me ask you a few those and they're kind of a little bit all over the place but we'll see we'll see where this goes jessica toy who's uh she's a p.m at

29:56

angelis she's actually a friend we work together at airbnb she asked a great question yeah jess jess is awesome she shout out to jess she's like been super helpful on the angels side so she's also amazing okay she's the best she asked what you learned as a pm that has helped you

30:10

in your venture career yeah so my background is marketing and then product management pretty quickly i used to work in the gaming industry which is like i think an awesome industry really hard to make it in that industry but like amazing place to learn and um i think product i don't know i i have so

30:26

many biases so i have to like be cautious of that but having a product background i think is one of the most important aspects of early stage startup investing meaning often times when you're building a new company there are a lot of risks and there's a lot of important things to to nail but it all

30:42

ultimately comes down to the product that you're building and so i think having a product management or product background is helpful in one having more i guess perspective and evaluating different ideas and and arguably more important how the founder thinks about things so it might be

31:00

less about me evaluating the the the market need for this particular idea but it's what's the thought process process and how this founder come to these product ideas and these insights and so i think having a product management background is helpful for that and i don't know i also just find it really

31:15

fun to jam on product with founders and when it's early early days there there's more opportunity to create some sort of impact or you know help shape the product in in a slight way awesome basically if you're a pm you've got a lot of the skills that you need to be a founder founder and and arguably

31:32

investor um as well that's right okay so uh leo of sousa ventures who's also an awesome dude uh yes if you could go back i saw leo in uh miami oh uh oh oh yeah he moved to miami too oh my god everyone's over there okay so uh he asked if he could go back and build product hunt again what would you do

31:53

differently we talked a bit about this but anything else yeah um i've been thinking a lot about this actually lately and um yeah i mean there's a few things one product in the very beginning and still today is very much focused on tech and there was at one point in ambition to

32:11

expand beyond tech into all different types of you know categories of products so you know we experimented with podcasts actually podcast discovery we experimented with video game discovery we experimented with book discovery um and the thesis there was okay this could

32:25

be actually discovery platform for all of these communities to discover all these different products and i think there was a lot of good ideas in that however i severely underestimated how difficult it would be to do two things one the product experience and product is very different than how you would want

32:42

to discover video games or maybe the future fashion and a bunch of other types of products out there and two it's really difficult to translate a community and expand into other communities like some some have done it like reddit is maybe a great example where reddit has this massive long tail

32:59

of you know every kind of community you can imagine but very few companies and platforms can actually do that so that's one one regret is we should not have tried to expand horizontally we should have just focused entirely vertically and served the tech community you know better and with more things which is

33:16

effectively what we're doing now another regret another thing i would have changed i would have i would have actually tried to monetize and generate revenue sooner we we raised a seed in the series a we had capital to grow and we didn't actually try to make money until after we were acquired by

33:32

angellist and my thinking at the time was and to some extent there's some truth to this is like everything you prioritize is at the cost of something else you know you're essentially taking focus from one thing to direct it to something else and what mattered most was growth and to grow the

33:48

community but what i really should have done is dedicated maybe 10 of our focus on revenue generation because you know it was once we started generating revenue we we did so very quickly and we got to cash flow break even i want to say a year maybe 12 months after we started generate revenue so if

34:05

we would have started in 2014 to make some money we could have been cash flow break even you know maybe 2015 2016 which would have just given us a lot of flexibility and kind of owning our own destiny and proving out some of the business model itself and then like the last thing because

34:20

i've been thinking about this lately is delegation is is a classic founder challenge um you know i i'm just generally a controlling person it's something i'm working on and it's really hard sometimes when i have such strong opinions and i'm very particular about certain things

34:37

to fully delegate and fully trust everybody that that said like an amazing team like i worked with some amazing people still people that are at product today like six seven years later it wasn't anything about the skills of the team it was just my own trust in my own delegation and what i should have done

34:53

is you know up until shortly before i left i was editing the newsletter every morning for example like every morning i was waking up you know 5 a.m 5 30 a.m editing the newsletter and that's just kind of silly you know to be doing that so many years later after starting i totally get that drive to just make

35:12

sure everything you're putting out and then your company's putting out is top notch i have the same feeling and it is hard to let go just like that's not perfect but i'm gonna i'm gonna be okay with that i'll do other things yeah it's it's really hard and i think it's a tendency that is um

35:28

in some ways it's good in that you care so much about the product as a founder you care so much about what you're building you care so much about the details and you need that kind of like almost ocd like uh behavior however you also just can't scale yourself nor are you the best person at everything so

35:46

i don't know with hindsight i'm like all right i should have delegated more i should have trusted people more and yeah there will be mistakes i make mistakes all the time but at the end it's going to be way net positive because you kind of have to do this to seal your company anyway

36:00

it's a good segue to a question harry stubbings asked that he finds interesting always what's the most painful lesson that you've learned and but that you're also happy about to have gone through yeah yeah there's actually i recently in the past couple weeks wrote a blog post

36:16

that i'm not really able to publish because it's it's basically when you there's certain things i want to share that it can make things challenging and complicated for others so i don't want to put uh anyone else in in a pickle so someday maybe i'll publish this post but to speak more vaguely about it like

36:30

there are some hard really hard times and product like you know we we have all faced in in different ways as founders or not even just as founders just as people but yeah there are some times where i felt physically ill many different moments in product hunt and um it was just really tough and you know

36:46

you i don't know if i don't know how to articulate that feeling but that flutter in your stomach that you wake up with in the morning of just anxiety and stress and and worry being a ceo or founder makes it slightly harder in some ways because you still have to put on this

36:59

mask you have to put on the space of confidence externally and and internally as well where people need to trust you you you also don't want to subject them to the same anxiety that you're feeling and be 100 transparent so it's it's a struggle because i think i i

37:15

don't know i value authenticity so much and i i kind of like thrive around people who are authentic however there is this like tension with with being a founder ceo he can't necessarily share everything so anyway everyone's gone through hardship building a company and the positive aspect of that is like

37:32

i think hopefully grown some empathy for founders who are going through hard situations i think it's made me a little bit stronger maybe thicker skin for certain things and just provided more perspective you know into the company kind of like building journey okay listen to this if you can take 15

37:51

seconds to leave this podcast a rating on apple podcast or spotify or any of your favorite podcasting apps you can enter to win 1 000 in cash plus other fabulous prizes including a one-hour coaching call with me a box of custom swag that i've just created that's full of really good stuff like an

38:09

awesome water bottle a hat and socks and a few other things and you also get a one-year free subscription to my newsletter and even a goodie box for athletic greens it's a giveaway bonanza and all you have to do is go to lennyspodcast.com bonanza to learn more and enter the contest just make sure you apply by

38:29

august 14th 2022 again the url is lennyspodcast.com bonanza and we talked about how hard startups are and how many people should not start a company but at the same time part of this question which i think you would agree with is you're probably very happy you went through all that and and

38:46

wouldn't change wouldn't like undo that right yeah yeah it's kind of like a lot of things you know what doesn't break you makes you stronger to some extent so it didn't break me it just scarred me a little bit but didn't break me and turn you into the ryan hoover that we that we have today yeah for better or

39:02

worse maybe one last question from from twitter and twitterroddies from sundeep you just wanted to know what what have you found matters most to you or mattered most to you in life and in business versus what you thought would matter most yeah um still figuring it out and i'm still

39:20

asking the old stereotypical questions like what what the heck is the media of life like what am i here for like all there's let me know when you figure it out yeah and maybe maybe there is no answer maybe the question is is actually um it doesn't matter so i mean if i'm

39:34

honest i'm still figuring all those things out i mean i think in in life some of the things that i've reflected on is so damn cliche but sometimes the cliches are true is like friends and authentic relationships have been i don't know they just matter so much i think and the older i get to it's less about

39:50

i don't know i care less about having a lot of friends and more about a few deep close relationships and i don't know i feel like that's very different than like middle school ryan or like you know when you're on the playground metaphorically speaking where everyone's trying to be popular and

40:06

you know meet a lot of people and even even joining and being in san francisco and the tech community you want to meet a lot of people and network and all those do all those things that's less interesting to me and less important and then more on the business side the thing i've been thinking about

40:20

is like again i think this is obvious to a lot of people but i think there's some nuances to it which is momentum matters so much and momentum is reflexive in that you know high momentum leads to more high momentum low momentum leads to more low momentum because there's this energy that that kind of

40:36

goes through companies where when there is momentum when people are shipping when things are going well other people feel that energy and they want to do the same but in the reverse someone who might be slowing things down not shipping not really performing very well that

40:48

actually does the reverse too it might lead other people to to feel less motivated or care less and so i don't know momentum is is this weird thing that you know arguably is one of the most important things in early stage startups and of course it's in an input to a lot of things but it's

41:05

just so important to nail mark andreessen talks about that that last point that there's like a word for it that i forget that a company is either becoming a gravity and pulling in all resources and funding and attention or losing it and it's really important as a company to know which one of those

41:21

are you and as an investor you often want to bet on the company that's just like they're just becoming the center of gravity here and there's not a lot you can do to change that once they reach a certain point yeah yeah that's a really good point i mean it also mirrors with like the power

41:35

law of the nest thing where it's it's in most people's situation it's one company is returning you could invest in 100 companies one of those companies is probably going to return 3 to five x and the returns of all the others may be combined in some cases so it's it's wild on the first point that you made earlier

41:54

about cliches and platitudes reminds me michael pollan has this point that he makes that like cliches and platitudes are cliches and platitudes because we've heard them so many times but that because they're true people just say them because they're so true and as much as we don't want to hear them

42:09

like there's a reason that we hear them again and again uh i had a similar recognition when i was on a little psychedelic journey where i'm just like man love is all you need love is always happy man yes okay now i figured that out but i was like feel that feel that right

42:26

now but it's true that's why people that's why we're like okay shut up i heard that that's in a song yeah i was listening to to a podcast about someone who was um basically describing like psychedelics as a gateway into like meditation and everything and how it could be one of those things that makes people

42:43

a lot of people who take psychedelics come across as another hippie cliche like person who repeats like the same things we've all heard many many times but there's a reason why there's a pattern there and you know he describes like you know psychedelics is one way to feel that and learn that that feeling

42:59

that you can't achieve with with meditation you know with experience yeah i think sam harris talks about this where you could either meditate for five ten years to work your way up the mountain towards you know enlightenment or you could just take some psychedelics visit it for a

43:13

little moment see what it's like and then be motivated to to work on getting there more naturally yeah this is a good time to play a little game that i invented just for you okay so you're the founder of product hunt okay and on product hunt people upvote ideas that they like best and so what i'm

43:32

going to do is i'm going to give you two options and you tell me which you'd rather which you don't vote and it'll make sense once we get going that sounds good okay cool okay let's do it okay tick-tock or instagram reels and it is context setting are these within the context of products i i like and

43:49

know or products you would choose to use that you like better yeah not like which will do okay business better business yeah okay okay i got it to talk for me it's funny reels i kind of joke with with susie my girlfriend i joke that it's like reals is like tick tock but like two weeks late uh

44:08

that's not entirely true but i feel like i see a lot of tick tock videos on instagram reels like after you know weeks after they've been published we'll see i have some friends that work on reels and i'm excited to see where they go okay next lacroix or toppo oh this is a tough one because i'm

44:24

generally a lacroix kind of person but toppo chico i like the bottle so when topo chico is available i'll go topo chico i'm sorry corey i i totally get that my wife's a huge toppa chico fan we have many many bottles they're beautiful they've kind of changed a bit they're like super

44:39

clear now they used to have a little a little tint very important yeah okay next next up bay area or los angeles uh los angeles although depends on the the tip is my goals if if i was you know a new college grad or someone young and new in kind of tech industry definitely san francisco you'll create a

45:02

lot of serendipity you'll you'll meet a lot of people but from a lifestyle perspective la la i just find more enjoyable weather's better there's hiking housing is cheaper so la today san francisco 10 years ago very nuanced dancer i knew you were going to say it late and so next is east

45:20

side la or west side la i don't know we we lived in hollywood up in the hills for a while so i don't know if that's east or west but wherever that is big fan i guess that's west right it's not near the water that's a really good question hollywood hills all right that'll be a third option

45:37

okay electric bike or regular bike nothing against electric bikes but i feel like if your goal is to get exercise then just get a regular bike but i don't have either i have a recumbent bike at home that i use for exercise and uh the reason why it's recumbent and not like a peloton where you sit up is because i

45:55

can do nails and work basically while i'm exercising wow very productive okay next dark mode or light mode light mode i've never used dark mode like ever actually i take that back tweed deck is the only dark mode kind of app that i use but i don't know if a founder is prioritizing dark mode before they have

46:18

product market fit too it's like a big red flag for me it's a little bit of a hot take uh some people are going to hate me for that but i don't i don't think dark mode matters for like 99 of people wow big big hot take what if they just go straight to dark and there's no light

46:33

mode does that count against them yeah that's fine as long as just one mode um the teams that prioritize all these like small things that don't matter before the product is actually is like useful for people or that that's this is where like my product manager hat comes in and i'm like is this like the highest on your

46:49

priority list i don't know no big asterisks it's all contextual sometimes like the audience you're building for really cares about dark mode like if you're really for developers maybe you need dark mode or some version of it but but yeah i'm light mode awesome okay did not expect that i love

47:06

it okay two more wash the dish right away or let it soak in the sink i'm looking at the sink over here right now um there might be dishes in there so that'll be my answer yeah bad habit no i think there's there's power in letting it soak i get i respect that let's all tell susie next time there's

47:25

power lenny said there's power in soap dishes there's physics it's soaking yeah okay last one web 3 or web 5 i don't know what happened to web 4. so i don't know maybe i'm going to look at the difference i'm gonna go one four okay we did it that was the inaugural yeah edition of which would you rather

47:43

up vote amazing i like this all right it's kind of fun this could be a fun little segment i think for a lot of things yeah it'll plug product hunt it'll be great we'll see where this goes this replacement lightning round which i experiment with okay but actually i have other questions

48:00

i want to get through before we before i let you go if that's cool cool there's kind of two topics one is around consumer startups and just a few things that i've been learning there and then angel investing and then and then we rap so around consumer by the time this post comes out i'll

48:15

have released some portions of this series that i'm working on on kickstarting and scaling and consumer business and there's a few things i've learned there that i just wanted to get your take on one is that what and we talked a bit about this just like 99 of consumer apps

48:30

seem to just like not work especially if they're venture scale if they raise money just like just a reminder of how hard consumer is like when is the last consumer app that really took off and so i just wanted to get your thoughts as what's your take there what should founders do that are starting a consumer

48:46

company yeah yeah it's tough i mean there's obviously consumers pretty broad so there's like different levels of difficulty i think um like consumer social or gaming like games building games is probably like the the hardest and the one filled with the most failures and i think a lot of that is because

49:04

a few things i think one monetization is generally harder than like a b2b company historically a lot of it's been like advertising driven and to do that you have to first get to massive scale for advertisers to really care and then you have to you know double it and double it and

49:19

double it again so monstation is super tough versus a b2b company it's like people have a problem they have a need they are willing to give you money you know on day one the other thing about consumer that's tough is you're you're always fighting different essentially you're fighting for attention and so

49:34

you might be some consumer social company but you're you're kind of like competing with netflix too which isn't in your direct domain but like people could be watching netflix or they could be using your product or your social app let's say so now you're competing with so many different things many of those

49:49

are incumbents where the consumer also has like built-in habits routines like this is a big big part about consumers too is eventually you want to be like an internal trigger in someone's mind where they they just without even thinking they go and use your product or services

50:03

for some reason usually you don't start that way you need like external triggers to like pull people in but eventually you have to get to that point so how do you overcome those internal triggers they have for other services other products it's really really hard and and then i think a lot of it is um

50:18

like b2b companies usually you have a clear like problem that you're solving and you can talk to customers you can understand what are their current behaviors what what solutions are they using now what do they like about them what do they not like about them whereas consumer there's a little bit of

50:33

that but it's it's fuzzier you know if you take like twitter and you kind of even ask someone like why do you use twitter and like people will have different answers that are all kind of like fuzzy and they ultimately tend to come down to some sort of like innate human desire like it

50:47

could be for twitter it could be about like i want to be informed with what's happening in the world or it could be i want to feel less lonely or connected to more people or something like that whereas if you go to let's say docusign i think it's a great example the b2b company it's like super simple it's like

51:03

a way to get legal docs signed online that's what it does it's a thing that people have to do it's very clear like what it solves and so b2b is like easier just to navigate that like idea maze um and so with consumer your your first blog post on this topic touches a lot on

51:19

the idea side and i i a lot of it resonated with me especially the the insight piece like what is what is the insight that you as a founder have to build this thing because i think it's really hard to build a consumer company without some sort of unique insight maybe impossible

51:37

and you can get that in many different ways it could be through your own experiences i used to write like a problem journal like just when things annoyed me or when things were like less efficient i would write it down as like a note and i didn't try to solve it i didn't didn't say oh here's the solution i was just

51:51

like this is annoying like in san francisco one example is a lot of people don't have laundry like in their unit so i'm like that's kind of annoying like that's a problem maybe there's a solution out there so things like that i don't know there's there's a bunch of different ways like

52:06

your blog post does a better summary i think of like the different ways different companies like ideated and came up with their ideas but uh we have many different ways to navigate it but needs an insight of some sort awesome i hadn't heard that uh that problem journal idea i was going to ask

52:20

you if you have any suggestions for how to come up with a startup idea and that's a really interesting one so i guess i'd be cool to hear where that came from and what that led to or if there's anything else you found to be useful around that yeah yeah the problem journal is one and

52:32

again like i think it's helpful not to try to come up with a solution but just right just simply write down like the problem you you observed or experienced another one i think is interesting is just to like immerse yourself in different communities ideally like maybe like seemingly niche or weird long tail

52:48

communities it doesn't have to be that necessarily but that might be where you'll see more unique insights or gather more unique insights and you could do that through i don't know participating in subreddits meeting a lot of people who are like really excited about some other thing it

53:02

could be like some weird robotics like niche hobbyist community for example and a lot of that i think will will hone or just like create serendipity for ideas you might see patterns or you might see problem statements emerge from many people in that community that are facing similar things

53:19

and then there's like the other other component too which is really about like observing trends and changes whether it's like a consumer behavior shift let's take um an obvious one today is is like distributed working so five five years ago when the weekend fun started that

53:34

was one of our themes i was like i think distributed working will be on the rise for a number of reasons one you know it's harder and harder to recruit two there's a subset of people who really value that flexibility and autonomy and then fast forward we had covay that accelerated remote working and and now

53:50

that's a huge consumer behavior shift not just in how people work but also like going to your airbnb like world like everybody has shifted their entire product to support more of this remote working kind of lifestyle just the way that the home page is now more of a catalog of places that you

54:06

could explore at different times of the year versus their maybe before was more like i have a very specific vacation trip that i want to take during these days in these areas it's like a very different like browsing kind of experience so that's just one example consumer behavior shifts is one thing to observe

54:24

the other is technology shifts so what what new thing can you build today that could be built yesterday and so there's there's a bunch of categories around there like web 3 a.i you know the biggest ship that we've seen is mobile and like early 2010s that unlocked a whole whole bunch of things so

54:43

so yeah i think it's observing those shifts and those changes last thing i'll say on that is like i think startups since there are more people building companies and technology there there's essentially more efficiency it's certainly not an efficient super efficient market but there is more

54:58

efficiency in problem discovery and solution exploration and so for that reason you need even more reasons for things to sort of answers to the why now like what's changed what insight do you have why doesn't this exist already because a bunch of people are trying to build

55:14

something in this space most likely so that's a lot of what we think about especially on the investing side when we talk to founders wow there's way too much good advice there have you written this down anywhere is there a tweet thread people can find like your kind of approach to coming up with an idea

55:29

i am not i don't think so yeah all right now we have a yeah or this is the uh this is the the content for people to save and use thanks for sharing all that that was really helpful one other question i wanted to ask you along these lines is around the target audience and uh an insight that we both share is that

55:51

it's really important to get it's really narrow with who you focus on initially as a startup for founders it's often so counterintuitive they're you know it's like oh my god why should i focus on a thousand people or 10 000 type people versus the millions that might want to use this

56:05

thing what's your sense and where have you kind of seen that become important just the idea of getting very narrow on how you're going after yeah it's effectively the the more narrow your your idea generally and this is where i throw in the big asterisks like not for everything there's always

56:21

contextual differences but generally the easier it is to build a great solution for those people because now you can actually hone in the product experience the messaging and everything to serve exactly those people and it can help with the product side it can help with the marketing and go to market

56:37

as well where you're messaging when people land on your homepage you don't need to create kind of a broader kind of like value prop to everybody but really you can focus on like what is the the problem this particular audience or community is facing and so generally just easier now

56:52

there is always that challenge of like well is this too small is it too too much of a niche if my goal is to build like a massive company my bias is not to worry too much about that because what you probably find is over time opportunities to expand beyond that you'll see parallels maybe to other

57:09

communities or other problems and a lot of companies you know eventually expand well beyond that like go back to airbaby you know the story way better than i do but you know initially it was like just you know basically couches and extra rooms and houses and like a lot of people most people in the

57:26

us would not do that like my parents not not in a million years even me like i don't want to like stay in some stranger's like room i want my own space my own house so like that that probably at the time seemed really niche and like small but obviously they extended extended well beyond that now

57:42

now have you airbnb is like housing and generally speaking like their tam is housing in my mind which they haven't expanded into like real estate sales or like long-term rentals per se but like that that's a possibility this is a good segue to the last topic i wanted to touch on investing which i

58:03

believe you do full time would you say that it's your full-time gig now yeah yeah it is yeah spending all my time there and yeah cool so from what i can tell the weekend fun is killing it i'm not an lp but it feels like it's kind of this underrated juggernaut that's just doing very well and so i wanted to ask

58:19

you a couple questions along these lines one is what have you learned about investing angel investing especially what's most surprised you i mean i feel like there's a lot well we've learned so there's there's things on the operational side so the whole category of of um

58:33

like running a fund there's a bunch of things that go into it from lp communications lp fundraising there's also like vatica who works with me on the fun side she um she describes like hygiene there's also good hygiene when it comes to running a fund for example you know when you meet a founder you

58:50

should get back to them like if it's a pass you should let them know and then there's a lot of different ways that you can do that some people you know might just say like pass and that's not very like encouraging to a founder if it gives you no context no details there's also an element of hygiene which

59:03

is we always follow up with the person that introduced us to that company and we just feel it's kind of like that's what we appreciate like we like to kind of know what happened like have them close the loop and it's just like good hygiene operational things that we've learned and kind of

59:16

honed over over the years i mean the biggest surprise the biggest surprise has probably been i got to be careful of how this is interpreted in some ways but it's there are cases when i didn't think the company would make it i either the product wasn't working and you know many months had passed and it

59:35

was very clear that they well to me i thought it was clear that okay this probably isn't gonna work out in my head i kind of wrote it off and then that company either pivoted or or some like massive partnership or m a kind of event came through out of nowhere and so i guess the learning is

59:52

like never count a portfolio company out until it's over and you know that relies on of course backing founders that are very resilient and creative and and you know driven to to create momentum you know out of nothing but but that's been surprising to me and it makes me kind of excited because you

1:00:09

know we've invested in over 110 companies now and uh it's it's fun to be able to kind of see behind the scenes a little bit how all these things kind of play out both the good and the bad that's such an inspiring takeaway does that change how you invest like to me that's like all right i guess i should

1:00:26

just take more bets on founders that are awesome although i find just founder bets it's like a very expensive hobby slash approach because there's so there's so many great founders how is that informed how you invest seeing that happen i would say we don't we don't have like um

1:00:42

it's again my cop out it's contextual kind of answer like you know some people are like we are team first only some are we're market first some are we're product first and we we look at everything kind of holistically and i think the evaluation of the product is sort of a reflection on the team so

1:00:59

our assessment of the thinking behind the product that they built today and maybe some of the traction is a reflection on like the team's abilities and like the thought processes so we try to look at it holistically and um i mean yeah i mean every investor would say like yeah we want to back you know

1:01:14

resilient founders that are very driven insightful and all those things of course but it's also sometimes hard to like fully evaluate that unless you really know that person so so we try to take as much data around like how the product is working how they made those decisions

1:01:29

leading up to this to to evaluate the team sort of indirectly that's kind of what i've started to do is i i try not to invest as a founder bet unless i just know them because it's just so hard otherwise yeah yeah there's a few founder bets that we've made one going back to consumer social kind of thing he's

1:01:48

somebody i've known for uh many many years one of the most talented like designers engineers product builders um and i've just been waiting for him to start a company and so that was that was one of those i'm going to bet on you because i believe in you i'm not sure about this first idea uh

1:02:04

you know who am i to judge but i don't know if that's going to be it but he's probably going to launch 10 apps and the 11th is going to be a massive success and so that's sort of the way i think about those consumer social founder first bets i love that last question along these lines for

1:02:20

someone that's hoping to get into investing or angel investing in the near future do you have any advice for folks around that yeah i actually um wrote a tweet storm and like converted it to a blog post on this because we've gotten a lot of you probably as well get

1:02:34

a lot of emails or people saying hey i'm thinking about raising a fund like how should i do that or i want to get into venture i want to start investing like what advice do you have so yeah wrote a blog post on this and there's many different ways to invest there's you know angel investing is one

1:02:49

so great thing about that is if you have the capital angel unless you do it today tomorrow like there's no no sign-offs required we have maximum flexibility but of course you need to have disposable income you need to be able to be willing to lose all of it and then hopefully you know you'll make

1:03:05

you'll be on the other side of that and make some money in 10 years it takes a long time they're scouting that's another opportunity they're more and more scout funds probably than ever before right now in different flavors some of them are like dedicated kind of scout programs where you have

1:03:17

capital to deploy on your own some are more like uh you still need approval but you send the deals and you get carry on those deals in many cases those have pros and cons too like they're easier to start and get into than raising a fund typically for most people but you also are sort of relying on that

1:03:35

that program or that fund um you might have less autonomy and what you can't invest in and what you can't and then there's a few others there's spvs is is one angle which works really well for a lot of people so um for those that maybe don't know i'm listening to this right now sdvs are

1:03:50

essentially like a single vehicle investment into one company so you raise money from lps from other investors to invest in this specific company and there are a few great things about that like one you get deal by deal carry meaning like the the outcome of that company is is you get paid when they

1:04:06

exit essentially assuming there's a positive outcome versus a fund you have to like return the entire fund first two it allows you to also bring in maybe very strategic helpful people into that particular round for that company which can actually be a strong value add for that founder

1:04:21

the biggest trade-off is it's a lot of work sometimes you have to basically do a fundraiser for every company you invest in and that's super time consuming for a lot of people and then the last thing is like raising a fund so that that's the decision that i decided back in 2017 is i want to raise a fund

1:04:39

it's a lot more work to raise the capital and there's a lot more responsibility in managing funds and so on and so forth but it provided me with the most flexibility and in a way to deploy many checks into many companies especially when i didn't and still don't have like a ton of money to angel invest

1:04:57

so um so those are like different options like i think my blog post goes into more like pros and cons for each of those things but the last thing i'll say actually is let's say none of those are really an option you you don't want to start a fun you don't have enough relationships to do svvs

1:05:14

for whatever reason you can't do a scout you don't have any money to annual less one thing you can also do is just like pretend angel invested and that doesn't mean you're meeting the founder and like writing a check but you can write memos or you can like almost create a fantasy portfolio and this is

1:05:30

what vetica before she joined join me was doing to some extent she was writing memos about companies she was excited about and in some ways she was like doing the job before getting the job and anyone can do that today and that can be helpful too if you're applying or trying

1:05:45

to prove your your your abilities you can say hey here are the memos here are the companies that i would have invested in you know if i had the opportunity and you know here's my thought process behind that i love that i'm curious about the logistics of knowing the prices of all

1:05:59

these startups but anyway we don't have to get into all that that's an awesome idea i've seen people on twitter do that too what's where do you think this all goes for you are you thinking of increasing the fun that's basically the last question just yeah what's what's the future of ryan ryan hoover at this point

1:06:13

as far as you know yeah still figure out the meaning of life as we established earlier i thought we cracked that one yeah yeah i'll let you know when i figure it out um um yeah we're on a third fund right now we're actually about 30 35 deployed so we have plenty of capital we're not

1:06:30

going to be raising anytime soon and yeah we're just investing in early stage companies right now but yeah when i fast forward like longer term i don't know um i i will always be investing i'm also more of a fan of maintaining a smaller fund our latest fund is 21 million and that might

1:06:47

i might change my mind on this but that might be the biggest fun we ever raised i might keep it around that same size for the next one because it really allows us to be like really collaborative we can write smaller checks we can fit into competitive deals i think it's a better product for

1:07:00

founders like we're not trying to take the entire round we can you know try to bring on the lennies of the world as co-investors things like that and so investing will always be a part of my future but i also love building building is is the most fun so creating something is whether it's a company i don't know i

1:07:16

don't know what it is i'm not going to even call it a company but building something is hopefully in my future i just got to figure out the right idea and maybe maybe reflect on your blog post too uh on the idea generation stuff that you shared because that that is helpful

1:07:29

as long as you let me invest all is good yeah well i don't know i don't know if part of me is like do i ever want to raise from venture now it depends on the idea if if i need it if it's required strategically then yes but to be quite honest maybe i shouldn't say this like i'm kind of really interested

1:07:49

in like just owning something 100 and you can always raise venture later like it's a one-way door so i kind of want to delay that door you know for whatever i build next if i can i 100 get that that's how life is with this newsletter operation and i highly recommend it yeah if you can pull it off yeah

1:08:08

okay i'm that's it just a couple just where can people find you online it's kind of a dumb question because you're very easy to find but where do people go to learn more if they want to reach out and then and then how can listeners be useful to you yeah i'm just uh easy to find r or hoover on twitter

1:08:24

ryanhoover.me's uh simple website um a bunch of old blog posts on there probably with a bunch of broken links and broken images but isn't there the contents there i don't know i'm we're investing we're investing early stage companies b2b btc building something weird i don't know dm me email me

1:08:42

amazing ryan thank you so much for being here it's kind of a surreal experience interviewing you and i'm really honored that you came and i can't wait for people to hear this i'm really happy about all the nuggets that i was able to extract out of your head and thank you for sharing them

1:08:57

thanks for being here yeah thanks lenny yeah these these conversations are helpful in like reflecting them on what do i actually believe anyway so it's it's just like writing it's helpful and it's just as helpful to everybody else so thank you again cool thank you so much for listening if you

1:09:14

found this valuable you can subscribe to the show on apple podcast spotify or your favorite podcast app also please consider giving us a rating or leaving a review as that really helps other listeners find the podcast you can find all past episodes or learn more about the show at lennyspodcast.com see you in the next episode