# Question & Answer: Rob Walling (Co-Founder of Drip, MicroConf, and TinySeed)

Channel: Rob Walling
Video: https://www.youtube.com/watch?v=AgQ0FhuTro8
Duration: 18 min
Language: English
Words: 3955
Transcript page: https://viewrankai.com/tools/youtube-transcript/AgQ0FhuTro8

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[0:00] [Music] [Music] so my first question is if you could snap your fingers and just make these people do something and just have that happen what would you have them do that you think would have the most impact on their success I like that question I think well so I think a big mistake that early stage founders make is not trying enough things and and almost you know maybe maybe thinking too hard and doing not thinking too much doing too little right so I think that there you're gonna have a big list of to dues or ideas coming out for this and I think that the two things is I'd say try to ship

[0:50] something something a sales page a cold email a LinkedIn outreach something that actually starts touching customers you know in the first six days five days after you leave microcon the other thing is start to try to try to start a streak like you pick up the calendar I don't think it was was a Jerry Seinfeld who did the calendar and he would write an X on a day that he wrote jokes doesn't matter if the Dukes were good or bad road necks pretty soon he had twenty thirty forty days of writing and he's like I don't want to break that so break out your calendar write an ex I mean

[1:23] similar you know Mike and I have been podcasting for like 300 years and their only reason that we've continued to do that is because we have a streak now that we don't want to break I thought a lot I was talking to Ted Pitts last night and he says I just like to make sure that every day I'm working on the most important thing and I make a little progress every day and if those two things are true you're golden yeah so what mistakes do you think people make consistently in the early days besides let's say not shipping you're not being consistent I think that I

[1:54] think these days there's a lot of advice coming at you and a lot of ideas and I think that going off the beaten path and potentially trying something that that you think is almost a flier or that no one else is talking about can be I think it can be scary but I think not enough people try it I mean as an example like how many people in this room maybe in the next month we'll go out and like try to buy an app instead of building it because the conventional wisdom or everyone's talking about building building but like going off that beaten path it can often get you

[2:23] there faster yeah I think being willing to not just take the prescribed route and again I run micro Kampf right so it's like we do have a lot of advice and prescription and I do think that that's good but I also think that as founders we have to make decisions with incomplete information and being able to take well you know at least a risk here and there I think is uh it's a good thing yeah what was your first thing a thing you bought was it the towels it wasn't the beach towels that was like the third or fourth I launched a bunch of things that failed that I built and

[2:58] then eventually I had to the point where I was consulting I was making a good chunk of money and I realized I had just a bit more money than time and so that's where I bought don''t invoice for like all the money out of my bank account it was like eleven thousand bucks it was a huge amount of money and that was in it was still an alpha it was really buggy and it was a bad purchase until I had my back to the wall because I'd written an eleven thousand dollar check you know kind of turned it around you you went over it really fast but I think it's

[3:23] important to call out for people is that you launched a bunch of things that failed yeah that was your start that's right yeah and it was five years of that you know nights and weekends on and off this was 2002 2005 there was no Joel Spolsky it was literally the only person blogging about this this is before I had started talking about it was pretty Patrick McKenzie was pretty everybody so I was just you know fishing around in the dark in essence so if you want to do what Rob walling did and you spend the first five years not being successful that doesn't mean you're not on the path

[3:51] like you can probably do better now there's more information now there's a better support network yeah so maybe it's three years maybe it's two years but starting with failure is not does not predict your future absolutely yeah I would hope it would be shorter for everyone in this room though just because we've all learned from the mistakes that we've all made you know and so hopefully you're standing on the shoulders of others to do that can make brand new mistakes which of your comic books do you value the most oh geez so little-known fact so one of my first businesses was selling comic books like in junior high

[4:24] in grammar school I would mark them up you know 25 percent or something and I always want and then I started a little comic book store and and then it was not cool to do that as late 80s Early 90s I could never afford the comics I actually wanted which were the classic Silver Age stuff first appearance of spider-man you know it's amazing fantasy 15 right amazing spider-man number one if it has two for number one x-men number one like all that the super hears that are huge on the screen today their first appearances are where you know low thousands of dollars back then well now there are

[4:50] tens of thousands of dollars and after I sold drip it was the first time in my life I had enough money that I could take little flyers with a small you know the two percent of my net worth in Bitcoin or whatever right and so it's 2016 and I bought yeah about some comic so I think my favorite one is it's you know it's it's slabbed so it's encased in this like you know plastic and it's it's grated and it's verified that it's you know authentic and everything but it's a first-person Spider Man yes amazing fantasy 15 is that in the the safety deposit box it it is it's worth

[5:23] well now so it was a few I wish I'd have bought it in the 80s because it's like tens of thousands of dollars now so yeah let's go I totally go there and like seriously just look at it and like you know can you smell it or is it in the box no it's in the box I have I have bought some other old comics for much less that are not in the you know in the case just to that old that old paper smells cool I remember after you sold drip I was talking to you and sherry and saying like you I talked to you about it

[5:49] and you're like that's the what do you think will be next like I'm definitely not doing a start-up again and I talked to Sherry I was like that's garbage right it's just like well I think he'll probably do he'll start something like you can't just hang out like what was did you know after drip had a sense of what would be next for you did you have an idea of your next step I didn't I wanted to take time off I'm I was a little burned out and it's just yeah it's a long road to go through you know it's like five and a half years from

[6:16] from when Derek and I started until I left trip so three ish year was right yeah three and a half years till a sale something like that and five and a half years for me is a long time like I've been working my professional career has been 19 years that's like a third almost a third in my career and I don't tend to I mean the longest job I had prior to that was like two years right I think a lot of us in here just get bored with stuff so I had no idea what was next but I did take six weeks off and then started

[6:44] thinking about tiny seed or just sort of think about what was next and looking at trends and it just became kind of obvious there was a another gap in the market so tiny seed is kind of a start-up but it's starting to feel more like that now that we're dealing with this it you know what finding product market fit and you know customer development and even like all the legal stuff that goes along with it it feels similar what you said when you when you said you didn't want to do a start-up again it sounded like because you like you didn't like it I couldn't you didn't

[7:11] want to stress again yeah you don't want the intensity to be quite that high do you feel like you've achieved that like it does tiny seed feel as stressful as Tripp did in the early days no yeah it's different like starting a sacis it's just for me at least in my head it's it's a lot different and and I feel like I don't know I feel like if I was starting no matter what I start like look at David cancel he's on his fifth start up he's exited four of them successfully not aqua hires but like sold them for quite a bit of money and it took him two years until drift and he

[7:41] raised I think 15 million dollars like on day one because he's David canceled and everybody wrote him a check and it took him two years to get to where drift was even like starting to get traction it doesn't get easier you know or I should say maybe it gets easier with more resources but it doesn't you don't compress that time and I think that's what I got tired of it was like you do one and then you do one and every time you're starting over and it's still a long journey and with tiny seed it's not it's not like that right it's like much more quick to get there so if people are

[8:09] thinking about starting sasses maybe they should instead raise a fund and invest in companies don't do that no I think if they're thinking about starting SAS they should a you know it's a guy mean you know I were just looking at compounding em are are like it is the golden ticket man it's what it's what I wif I were not where I am today I would go start a SAS but I I've done it now and I've kind of you know I want that next challenge in all honesty it's not just because I burned out it's because because I'm all healed from that now but it's it's because I've done it a bunch

[8:38] of times right you don't wanna do the same thing three four or five times it does get start to get repetitive and learning new things I think is what a lot of us are here for what did it take to get healed from that burnout time off yeah just distance from things I mean that's I bet most people in this room have burned out on something or other read on your work on whatever and it often takes a lot of self-reflection it might take going on a retreat taking three days and and burn it depends on how far into that you are you know but distance time off that kind of stuff

[9:07] probably helps to have a spouse who's like a therapist for founder's in particular does indeed slash coach now where would you say are you familiar with the term zone of genius yeah where would you say yours is that's hard that's hard because like when I was working on drip it was like with Derek it was like our ability to build a product that people wanted and go where to make the right call to go not just listen to every customer but go where we felt like the market was going and to kind of look ahead twelve months and be like marketing automation is going to be

[9:41] a thing and ended bad on that maybe that's it I don't know because I think of like micro coms like we started it when SAS wasn't a thing as 2011 we started it when there really weren't many startup conferences it was BOS and you know a bunch of venture funded stuff and yet here we are you know what zona genius might just be showing up for a long time honestly you know just I mean again the podcast 438 episodes the conference the 18th one you know most conferences don't last more than three or four trip was a slog for two year you know maybe that's it maybe

[10:16] it's just like that value hard work that you learn as a kid you know playing sports or working on on on things I don't know I don't know that's a zone a genius as much as just an ethic or you know it's like I'm gonna pound my head against this thing until it's until it works I like that a lot people I've had I have built up a bit of an audience over the years and people like how do you how do you start building an audience I'm like just get going and do it for a long time yeah and if you want to get where Rob is it's kind of like

[10:42] show up again and again and do these things really and some of them don't work as we've talked about I mean even things that I did in the late you know 2008-2009 flopped pretty pretty baggage I wrote some ebooks and tried to sell them and that was dinner you know I mean you still have these failures but you don't need to be right every time I mean you can be right you know half the time and do quite well yeah and it sounds like you for your first answer to that zone genius question was kind of like spotting the next trend mhm and I wonder how much of that is the fact that you

[11:09] showed up so much and you were so plugged in because you did the conference so much you did the podcast and you saw was resonating yeah yeah that's right it's exposure right it's like how do you get exposed to intelligent people doing interesting things and and have a lot of conversations well you do it by running a conference or having a podcast where you answer a hundred and twenty seven questions in a year you know you're just constant we're just constantly thinking about what's going on in the space and eventually you do start to see patterns hopefully they're not just in your head you know they're actually actually real

[11:37] what are your investment criteria for tiny seed yeah that's an interesting question I mean I don't I don't so we do have a doc that like you know it looks like mr orange urn and all these things how do they look and then founders do they have this this that you know what's their zone of genius I mean we kind of have that in the doc look what are what are those things I mean it's it looks really at it's like founder founder founder and then it's traction and then the is the market big enough to at least get into the seven or eight figures right cuz there's some markets that are

[12:09] just too small and then what was the last one oh the product itself right those are kind of the five it's like I I think we I think it's maybe techstars who says it's like founder founder founder market product that's there that's a thing and it's like real estate right the three rules of real estate location location location they're basically saying founder is you know two or three times more important than the other things what attributes of the founder I think there are a lot of different ways to be successful as a founder this is thing I've learned you know a running running this community and working in the community and also

[12:41] I've done angel investments right for the past couple years eight years I guess now and I've learned that that there are certain founders who get through because they're successful because they're like they're just they're pushing it and you know they're gonna kill it and they're aggressive and dadada but it not aggressive in a bad way but aggressive in I'm gonna be successful and then there are other very soft-spoken chill founders who just show up every day and get it done there's there's people with like ass a skill set that's super cool there's people with marketing skill set there's people with design development like each of these

[13:13] something has to relate or there's even subject matter experts we're talking to a founder who has a PhD food science and and that and the SAS is in like the food you know the food ish kitchen space or whatever so I guess that was yeah that there's some type of expertise and I think that some I think the whole idea of Silicon Valley pattern-matching where they're like it's Mark Zuckerberg but I could say you know 24 year-old college dropout or whatever like I don't I don't believe that I think a big part of it is because of the founders in this community who have seen who don't look like him

[13:44] you know in so many ways not just physically but I didn't get here that way you know and and I think a lot of people here come through other avenues and so I think almost having an open mind to different experience levels I think is important how do you fight the probably very natural kind of bias to choose people that kind of remind you of you I don't think I'm the best founder like I don't I think that I should have gotten where I got much faster and if I was a better founder yeah I do and that's how I fight it cuz it's easy I

[14:17] actually want people who are who are different than me who have more design chops or more development jobs or more you know whatever it is there's there's just ways to be better than I am for sure when you say that you feel like you should have gotten there faster what do you think kept you from getting there faster fear yeah I was I was too scared I mean this is this is Rob circa 2005 too scared to send cold emails I was too scared to get in face-to-face conversations at conferences I was too scared to get up on a stage and speak I was the first 10 podcast episodes we

[14:49] recorded they are awful and we were terrified and we almost scripted out the entire thing almost verbatim and the terror of first I wrote a blog post called that and it's like the first time you do anything you're really scared of it and then the tenth time you do it you're just not so like being a parent stage right now zero fear but the first time we were in micro calm like we were super jittery and all like you know that's what we started telling the bad jokes was almost alike we didn't know what else to do you know it's like how do I not just sit up here and kind of

[15:19] like shake like this and have a wee you know in it and that's that's what I wish that I wished I had yeah I wished I'd had more confidence I think that it took me a long time to build alright I'm gonna switch segments here so this is the underrated overrated segment homeboy stole this from Tyler Cowen so I'm just gonna throw out a couple things and you tell me if they are underrated or overrated you're not gonna mention reality TV stars are you nope alright good alright chatbots overrated but in the short term overrated in the long term underrated welcome because I think they're gonna be

[15:53] a thing but I think there's a bunch of much like cryptocurrency where it's like I think in the long term cryptocurrency is a thing just a personal opinion but in the short term everyone thinks it's a thing so it's really overrated Las Vegas overrated every year we try not to do it here but hopefully next year won't be in Vegas okay we do it for her yeah I know we do it here for cost reasons we would tent we would probably have to add $200 to each ticket price in order to like move it to yeah would you pay that show of hands would anyone pay 200 more it's

[16:23] not very many people actually so paid ads that's good I would say underrated insert it depends on the circle but I think that not enough people take advantage of paid ads because if you can get that engine going it's it's not like pouring in a dollar getting three dollars out super cool did you make that work for drip so-so I made it work really well for hit tale I made it work really well for a bunch of smaller apps before that Donita voice was one of them drip it we had positive ROI but it wasn't like a major growth engine like integrations and other things were you know the kind

[17:04] of community and getting that many brand up were I'd say more powerful word of mouth but paid ads paid ads is good Twitter overrated I have wanted to quit Twitter for like three years but I keep getting pulled back to it how come why am i pulled back to it or what yeah I don't know I mean I obviously I enjoy conversations you know with folks in the community but I feel like there's there's no nuance there and if you actually have a conversation you should probably just do it on a podcast so I'm gonna ask a question on Twitter and I will start replying and it's like this

[17:36] is gonna take me a thousand words or five minutes on a podcast to actually answer it well with nuance and not just say one sentence like one sentence typically doesn't capture yet so I struggle I struggle with that Batman underrated Lego Batman is super cool I'm not sure if you've seen it thanks Rob Thanks [Applause] you

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