Danielle Messler



  • This week we’re diving into what happens when things don’t go exactly according to plan (so, always!).
  • Andrew & Danielle talk about the curse of perfectionism and how it impacts creative work.
  • Andrew discusses how he decides what is a launch dealbreaker and what gets cut to get things out the door.
  • We also dig into the importance of realizing you don’t have to do everything yourself.
  • Get priority early access to Thunk:
  • Follow us on Twitter @nalband and @danielleismessy


Isn't it crazy? This is our third episode.


I know flying by I can't believe it.


Last week we chatted a little bit about launching the beta. And kind of how perfectionism can stop you from making meaningful progress.

Which I think is really funny, because we had a couple...I don't know, I'm gonna call them setbacks this week and...


...perfectionism problems...



Yeah!...perfectionism problems. And so, you know, this week we can, or today we can really dive into what caused it and how you move through it and how we plan to avoid it moving forward.

But first, drumroll, please [drumroll sound effect]. What is our user count for the beta?


Yeah, so we started with 45 people on this waiting list ready to join, and about 73% of them asked for invitations. So that's really cool.

So about 33 people requested invitations, and we've got about 24 of them in the app journaling right now. So about half.


That's super exciting.



Yeah, I'm thrilled. Those are higher conversion rates than I think we'll ever have going forward. But it's nice to have such a high conversion right now.


Hey, take the wins where you can, right?

So you know, kind of speaking of the beta a little bit, we thought we would launch last Thursday when we were recording, but we ended up being a little delayed by 72 hours. We launched on Monday, so not that bad.

And for me -- I thought we were gonna have this podcast out, I was gonna have this amazing landing page with all these cool things and like a whole blog going. And even today I actually had a whole other idea for the topic of the episode based on those things.

But again, those little perfectionism things got in the way. So I guess going back to the launch, what was really the key reasons you decided to push from Thursday to Monday?


Yeah, so there's really kind of two pieces of it, one of them I would call psychological. And the other one, I would call something to do with the way we just went about it.

So the psychological stuff is, you know, you get down to the wire, you've had a few months to build this thing. And all of that work is kind of behind you. And you're anticipating the moment of dropping this thing live.

And you're thinking, "Man, this is really terrifying. Like, have I crossed all the t's have I dotted all the i's?" Finally, the day, right before we're about to launch it, I actually had the sort of danger moment of like, "Okay, let me write down every single thing on the list of things we could possibly do that we might need to do to get this thing out the door."

And I think that functions a little bit as like, "Oh, man, this list is too big, it's gonna take us a little time." And so we push back a couple of days, it's kind of like the inevitable crunch, except we were like, we're not going to go crazy crunch, I'm not going to make everyone stay up until 5am to get this thing out the door. And we're just going to take a couple extra days to get it done. 

Then there's the other side of it, which I would just call maybe a tactical thing or the way we went about it. And I think a lot of that has to do with this idea of a launch in general. So now that I'm looking at it, in retrospect, it's, we probably could have gotten this beta thing out the door a lot earlier and a lot dirtier, and a lot more of a broken format.

And I think that would have made the idea of a launch seem less of a big deal. Sort of easier to to get over the hurdle. Because it's like the more months in you are, the more sort of invested you are into the moment of like, we're pushing the button, and it's going live.

So in retrospect, looking back, I'm like, man, I wish that we opened this up in a very small way, you know, a month or two ago to even some friends or, you know, pushed a little bit harder in that sense to get people into it.

Because having a series of smaller steps I think just would be much easier to get out the door versus the launch moment where you sort of build all this pressure up to it. And once we finally pressed the button really it was kind of fun.

And I'm like okay, now we've got a few people in and we can start to work from here and it lays that foundation. So maybe that's one of my big takeaways from launching is we should have done this earlier and smaller and you know, just kept building and growing.


Yeah, and I feel like that's pretty common for a lot of product launches. That, you know, you kind of have these multiple launches for the same product, it's like this is "the first one." And then this is "the friends and family one." And then like you roll out a new feature, it changes the branding. And then it's another launch.

And I mean, once you get down the line, it's only really like the big launch that that matters. You know, we kind of made dinner for people who are a little bit more forgiving before opening the catering company and ruining someone's wedding.

The worst food they've ever tasted. 


Absolutely. How about you, Danielle?

Is there any roadblocks that you encountered, or anything that came up for you?


Yeah, I really wanted to get this podcast off the ground. And not just this podcast, just all of the other content that's going around this.

And I know, we'll speak to this in a future episode about the larger kind of content and podcast strategy, but the first step is really just having a place to publish it. 

And we tried, you know, setting up Webflow, and it was a little funky, for some reason, I could not get the links to all be on the same line, which apparently is like a common problem with Webflow. And then it just wouldn't stop kicking me out.

And it just kept taking a few days, and you know, I have a full time job, so not a lot of time to troubleshoot. And I just realized I was going down these rabbit holes of trying to fix this thing.

You know, I feel like we're in a lot better place to start going, moving towards that goal next week.

Going back to the beta a little bit, and on Monday, we knew things weren't perfect. We still had all these comms we wanted to work out. Yeah, we probably could have pushed it a whole other week. To just get all those little things right, and have all the right emails and the text messages and blah, blah.

How did you kind of weigh the decision to just do it live or push another week or another day?


I really just went through the list, and I looked at the list and I said, "How many of these are like project ending mistakes if we don't get them done?" You know?

So if we launch, we don't have this thing, like how likely is it that this like ruins the product, the product and the company?

So I went through the list and that was really helpful. And I eventually...when it came down to the actual day, I took everything that didn't you know, when I looked through the list, anything where the answer was not "Yes, this will end the company or the product or whatever we're trying to do," I just pushed it off, I said, "I'm going to look at this after we launch, I'm going to open it up and we're going to get started. And we'll come back to these things on this list. And we'll see how they feel then."


I think that's a really good point. It's definitely something I've done to myself over and over. And when I was making my website for Boston Brunch Guide, and being like, "I want this to be so beautiful and perfect." And I spent hours just trying to arrange the columns right in Squarespace and all this stuff and do tutorials.

And I wasn't actually doing the thing that I was good at, because I had this chip on my shoulder that I had to do it all myself.

And then I ended up seeing a friend that was doing, you know, just like pretty simple Squarespace design and formatting and all of those little things like connecting the blog post so that they're like nice collections and setting those things up.

And I was like, I'm gonna save myself a lot of time, a lot of yelling at my computer and being really frustrated, and just pay him to do it. And I mean, yes, it cost money. But it wasn't an insane amount of money.

It wasn't like I was asking for the most ridiculous website in the world, it was just kind of like an enhanced Squarespace template.

But the time saved actually was worth so much more than the money I spent. Which I think is a really hard lesson to learn because a lot of the times you want to do everything.


Yeah, I mean, you're reminding me a lot of this book called "The E Myth," which is very much about this idea that often people who are subject matter experts in something are wanting to go out and start a business in that thing.

When they go out and start the business because they love whatever it is -- baking pies, making apps, you know, whatever. And they engage in it and they start trying to do everything and they find that over time, the business has become like a burden.

It's like a you know, it's like something they're carrying around because the example in the book is the pie shop where the person is running it and she's running a cash register and she's doing the books and she's baking the pies and she's cleaning the oven out at the end of the night and she's sweeping the floor and she's just exhausted, you know, the business has become this huge thing that you have to manage.

I think it's really easy to forget that you know, going and finding people, I don't know, maybe the struggle is just asking for help and admitting that you kind of need some help.

But that's such a better, you know, way ultimately, to get to the goal line and to sort of accomplish what you want to do. And it's not meant to be this impossible struggle.

And if it's possible to do you know, I think, really going out and getting help where you can is powerful.


Do you think that that's also a perfectionism piece? Like wanting to do it all yourself?


Yeah, I mean, the book would say that you have a bit of a superhero complex if you're starting a business anyways. Yeah.


Oh, God. Yeah.



And so I think that that is definitely a perfectionism thing. In some sense it's a little bit of an ego thing where you're like, "I can do it all." And it's also a little bit of a like, "Well, I just want to make sure everything's right."

And that's a tricky thing to get correct. I don't pretend to have that all figured out. Because certainly, I care deeply about all of the details of what we're creating, and the experiences that people have.

And I want those things to be really, really world class. And yet, sometimes I just had to get something out the door. And it's very difficult to let go. And it's very difficult to know, you know, I think there is a real benefit to pushing hard and trying to figure out like, "How good can I make this thing?"

And how can I maximize the quality of it, there is a real value to that. And then there's this other very real value of "I shipped it, it's out, it's in the world," you know, and it's not perfect, but it's there, and somebody's interacting with it. And I'm learning something.

And I just, I don't know that there's a perfect answer to that. But that's a balance that I'm always trying to strike and do better.


Yeah, and that's, like, kind of a moving target, right, is finding that balance between good enough to ship and not a piece of shit? 



Yeah, you know, I think that what's really hard to see, sometimes it's really hard to realize is that often what's more interesting to learn to watch and to engage with is something that's a little bit frayed around the edges that, you know, isn't quite polished perfectly.

And, and oftentimes, that is much more engaging for people to see. You know, I mean, stories are, are one of the core elements of stories are that there are stakes. And so it's much more interesting to see the true human being trying to figure this thing out.

And I think, in some ways, maybe we want to protect ourselves, or we don't want to really be vulnerable. And so we present this sort of polished version. I mean, this is what the Instagram world, right, you know, where you're sort of presenting this very polished version of reality.

And oftentimes, I think, maybe we've gotten so much of that now that we're just hungry for somebody that it looks a little more like, you don't quite have it all figured out.

And that we could relate to, you know, and so, that's, that's a difficult thing, honestly, when you're, you know, when you hold that belief that really striving to make it as good and polished as possible has its benefits, but then still sort of thinking, "How do I let this out the door and feel kind of authentic?" And, and, you know, I think that's a very real thing that I'm learning more is, sometimes it's better if it's not totally polished, it's a little rough around the edges. 


You mean, you didn't sneeze and end up on the Forbes "30 Under 30"?


As an old geezer? No, I haven't made it on that list. I don't think I'll be there.


It's um, it's interesting, because I was watching this masterclass, and I forget which author it is. But it was on storytelling.

And one of the key elements that this person was talking about was this idea of conflict for like, your hero of the story, and how low the tolerances that the audience will have if the obstacles the hero faces aren't big enough, or they're way too easy to overcome, and you get so bored, and as someone listening or reading the story, you're just like, "Oh, it's too easy."

Like, I'm going to give up and not that you want this to be like super difficult, like don't really want building things to be like the Hunger Games or facing Voldemort or anything.

It's just nice to see that like, actual people and entrepreneurs go through these things. And they're actually like, real problems, because I feel like a lot of the narratives out there now are like, "Oh, they raised $20 million from Google.

And then, you know, we're self made into this blah, blah, blah." And it just seems like so easy. And I mean, obviously, it's not that easy behind the scenes, we never have full context.

But not a lot of the time is that story told, while it's happening. It's only told in retrospect, when you've already made it over the hill.


Yeah, I mean, there's obviously survivorship bias in those stories. But there's kind of, you're reminding me of this cliche in the startup world, which is just the answer to "How's your startup going?" It's always "Oh, we're crushing it! Like we are just crushing it, everything is going so good."

And that's, that's basically never true. It's almost never true. But it's always the answer that founders give, you know, and the tricky thing there is I think we forget sometimes that people who are founding companies are selling this thing to a lot of different people, they're trying to make it look good for employees that work there, they're trying to make it look good for venture partners that maybe are going to give them some money.

And, you know, I think it's a character from like, "American Beauty" who's like to be successful one must always present an image of success. And that's kind of what's going on. Right? Is this sort of...


Fake it till you make it 


Yeah, the story is being told, then. I don't know, I think we've got so much of that story, that maybe, certainly in the early days, it's like, why not just tell it tell a story that's more real and honest, and, you know, shows how messy these things are, you know, having been around many, many early stage companies when I was involved with TechStars.

One thing that was very true was, the struggle is real. I mean, companies are struggling, you know, and I think it's really, there's a, there's a public perception that starting a tech company, you have an idea and it's just like cake, and you go raise money, but it's really so much more difficult than that. 

And there's a lot of luck involved. And I think we are very used to seeing those success stories or everything seems to work and we never really get to hear the moments where the founders are sleeping on air mattresses in their parents basement, and eating ramen, and like, "Why did I do this? This is the worst decision that I ever made," and almost stopped like that day. You know, those stories we rarely hear.


Yeah, and if we do that, I feel like they're very Hollywood special of the week. 


I mean they're told from the standpoint from the arc right of, "I had nothing, and I almost gave up. But I believed in myself, I pushed through, and I conquered! And here I am successful startup man, conquered the world!" You know, and so that's definitely how that story is told.


I felt this in, like the...oh God, I hate the word "influencer." But with you know, other food bloggers I've met through doing Boston Brunch Guide and Instagram at events, and, you know, seeing the people that were doing this full time were kind of putting on this persona that, you know, they were making it work, and they were crushing it as, as you said, and getting all these brand deals and all these trips across the country and blah, blah, blah.

And then you know, you'd like get to know them a little more and you're like, oh, so lovely person, but, you know it helps to come from a millionaire family that can help you live out these dreams.

And I think that that was a big thing for me to realize, too, that, you know, it's okay to be where I am and to work on these things when I can and not put myself in the paradigm of other people.

But I think you know even though we had some setbacks this week, and it still kind of feels like a little bit like we're treading water and, you know, moving along.

What was the most exciting part of the week for you? What's the best part been? 


I mean definitely having people in there just using the thing and seeing that, you know, some number of people journaled more than once and getting some actual, like, feedback from folks.

You know, I've had a couple people reach out and say, "Hey, you know, I'm enjoying it. I'm really excited about the project. You know...this is cool. Thank you for inviting me." And that's a really surreal thing.

You know, it's, it never ceases to amaze me when I get to this moment from something that was really just a concept that I was dreaming about alone in my head. And now we're talking on a podcast about it, and there's a thing and it exists, and I can go to it and there's folks who are helping make it come to reality.

And there's real humans who are in there like experiencing it. And that's a really, that is a very addicting thing, you know, when you get to that moment of thinking, you know, "Oh, I want to see this thing in the world," and then eventually, it becomes real, that is really, it's really, there aren't a lot of feelings like that in the world where you're sort of like, it just was like nothing, and now it exists.

And that, for sure, has been the best part of this week for me.


And it's also, I think, the ultimate proof for getting it out as early as possible because you start to get those responses and people using it, and you're seeing them be excited and getting that feedback.

And it just makes you want to go in more. And I actually had something similar this week, when I was, you know, couldn't get the Webflow to work and then I was looking at our content and going through our first podcast that we recorded. And it was just, you know, listening to it and reading it. And it probably had been like a week or so since we got the final and reading the transcript.

And I was just pulling out, like so many content ideas, and just getting like really inspired again. So that was a really exciting, exciting moment. 



You know, honestly, it's been the same way for me with seeing people get in there and starting to get feedback and hearing, you know, actually having conversations with people who, you know, up until now the conversations that I've had with people are very brief, you know, hour long conversation, and you're just trying the product very briefly, and I'm watching you work on it. 

And so it's really not a real experience that you're having with it. I'm sitting there watching you. And so I'm having a different kind of conversation now with somebody who's actively using it for the intended purpose. And that's different, and that's awesome.

I've found that that is really energizing, you know, like I'm waking up, I'm like having a really hard time not going into my email to like talk to people who are using the thing to understand what they want. And I'm also really feeling reengaged about kind of everything, like the content that we're trying to create the way that we're trying to run this program.

And also, I've been spending a lot of time just in the design tools, trying to improve the product and think about what's next.

And where are we going to go next and getting really excited about what are we going to be able to show these people, you know, that are talking to us now and how are we going to be able to allow them and impress them as we go forward?


I'm excited. So much to do by next week! 


Yeah, I can't wait.

As usual if you want to get involved in Thunk, you can send us an email at

We'd love to add you to our waitlist and to bring you into the app and start to benefit from getting feedback from you. So thank you so much for listening, and we'll talk to you next week. Bye bye.


And you can find us on Twitter at @danielleismessy and @Nalband ...exactly how it sounds.