Danielle Messler



  • In the season one finale, we talk about what’s next for Thunk— and where we hope to be when we come back.
  • Andrew and Danielle talk about the difference between experimenting and failing (hint: it’s what you do next).
  • Danielle talks about when you have to ‘kill your darlings’ when it comes to marketing and content, and why it’s important to view them as longer term investments.
  • Andrew talks about his experience with other startups, and the tipping point between failure and success.

Episode Transcript

Andrew: Welcome to another episode of Finding The Net. I'm Andrew, product designer, CEO, and creator of Thunk, a journaling app that lets you find patterns in your thinking.

Danielle: And I'm Danielle, a self-conscious creator and content strategist building Thunk's audience alongside Andrew.

Andrew: This podcast is an inside view of what it's like to build, launch, iterate on, and grow a consumer application from the ground up.

Danielle: We're on a mission to get 1000 people using and loving Thunk, and we want to bring you along for the ride.

Andrew: As you listen to Finding The Net, you'll learn from our mistakes and our wins, and you'll find new ways to approach your own creative journey. Let's get into the episode.

Danielle: Let's get into the episode. We do have some news that this is the last episode of season one.

Andrew: It's true.

Danielle: [crosstalk] episodes. Andrew, do you want to talk a little bit about where we're going from here and what's next?

Andrew: Yeah. We are at a, what do we call this? An inflection point where we're looking at all of our efforts and trying to figure out where we should be focusing them. And we're going to take a pause from the podcast and focus down on a few things that I think really need our attention for the next month or so. And we're going to start back up in about a month with where we're at, at that point, and some of the progress that we've made. So some of those things are, making sure that all of our communications are stellar, amazing, and awesome so that we have an automated system that when somebody gets in touch with us we really manage that relationship without us having to send a million emails.

Danielle: We're going to have the best emails.

Andrew: Yes. The other big thing is to just focus much more directly on what's working for acquiring people, and really try to target that. And then the third thing is getting our product to where we want it to be. And in the middle of this podcast, a couple episodes ago, we shifted pretty dramatically from a dedicated journaling tool to something that's much more focused around connecting your ideas and generating new ones. And that's something that we really need to focus on, honing our messaging, and getting the product itself to support that portion of the vision. So there's quite a bit of work and energy that needs to be focused in that area, and that's the third thing. So those are the things we're really going to be digging into over the next month or so. And when we come back, we're going to have all sorts of stuff to report.

Danielle: A billion dollar startup crushing it.

Andrew: Yes, we're going to be crushing it.

Danielle: One of the things I've been thinking about this week going off of that is just this importance of experimenting and trying different things out, especially in marketing and in content, because you don't ever really know what's going to resonate until it resonates. It's a much less linear thing than I think a lot of other professions where you're like, "Okay, I know if I invest in this stock at, blah, blah, blah, blah," and you can track the results. Marketing is a little softer in that sense and the way you find what works for different groups of people is just really being able to experiment. And I think one of the hardest things, and at least this has been hard for me in the past, is this idea of kill your darlings when you're attached to a good idea or something that you've put a lot of work into and it's not working and sometimes you just have to let it go or reassess or pivot.

And there's been a lot of times where I've thought of that as a failure instead of, oh, okay, this is information, and this is working this, isn't working. Not to say that the podcast isn't working or it's not been awesome to do, but that's just been something I've been thinking about this week.

Andrew: I actually think we should own that the podcast is not working in so far as the explicit purpose of the podcast is to drive folks to sign up for the beta program. And I think that is a very real part of why we're saying, "Well, let's take a minute to step away from this and to focus on some things that are doing that." I think in the interest of our own honesty with ourselves, we should own that, right? I don't know. Do you see that differently?

Danielle: I do, in a way. I think it's a longer term investment, and we've been talking a lot about, "Okay, we need short-term and long term." I think long term something like a podcast or a content series is a lot of work, but it takes a lot longer for results to show up, but can have a pretty dramatic effect. We're also going to be using a lot of this content that we've talked about to generate other content.

Andrew: Wave two, if you will.

Danielle: Yeah, exactly. So I think it's more, okay, where does our energy need to be right now? And I'm going to put a pause on this and reassess rather than, "Ugh, this thing isn't working. Fuck it." Not that I was saying that's what you were saying. I just wanted to make that voice for some reason.

Andrew: Well, it's interesting what you're saying about killing your darlings and things feeling like a failure, because I think that's something that there's a lot of talk of failure and fail fast and all that good stuff in the startup world, and I think it's also real that it's no less painful when you're like, "Well, this, whatever we're doing right now, just isn't working." And that is what happens until things start to work. And I think it's certainly true in marketing, but it's probably true of the entire everything we're doing, the product, the marketing, the entire business itself is not a functioning business right now. If we were to just play out on the exact same path that we're on now we would expect, if the numbers every month look like the numbers they'd have every other month since we've started, the thing would die.

So there is a strange thing that you go through, I think, and I've worked at a lot of pre-product market fit companies you're just always failing until you're not. And it's really hard to know at what moment does it start to work, and little things do happen, you know what I mean? And so to brighten the mood a little bit, we did get our first piece of public congratulations or, "Hey, I really like this product. I'm using it and I'm getting something out of it."

Danielle: Yeah, it's a big milestone.

Andrew: Yeah. Look, that's not insignificant. That's real. It's a very unusual thing in the early stages of a product to have someone go out and say publicly, "I'm using this and enjoying it and getting something out of it." So that's a funny thing where there's a little win is tempered in amongst a bunch of stuff that's a real struggle. And I think it'd be funny if you were there the day that that happened, because I think Courtney was looking over at me and I was beaming for a full hour just because I was like, "Oh God." Because the truth is, since October or September of last year, I haven't thought about much else than this and I haven't done much else than try to advance it. And so it's an incredibly relieving moment when you just have one person that goes, "Oh yeah, you're not insane."

This is such a difficult period of the work, honestly, because it gets to a point where you're like, "God, I just need something to work." And that can help a lot when you just have one person go publicly, "I like this. There's something here. There's some value." And those little moments are really powerful, and I'm very confident we're going to have more of them, to be honest. This will probably sound a little doom and dd gloomy, but I'm very confident we're going to have more of those moments. And I think the refocus that we're doing right now is the type of thing that will allow us to have more of those moments. It' the exact thing that's needed, which is a really powerful and positive thing even though it feels, I don't know about you, but a little funky to be like, "Okay, we're going to focus down on a different area."

Danielle: It's like when you're throwing an event or a party or something and you just have no idea how many people are actually going to show up. And then it's like, "All right, it started 10 minutes ago, and two people are here and no one's eating the cheese." And then all of a sudden, an hour later, people start to show up and you're like, "Oh, okay, why did I worry about this?" But that 20 minutes where you're just like, "Shit, no one is coming to my party," it's very emotional.

Andrew: I really like this analogy, because it's exactly like that except it's a two year stint. So that 20 minutes lasts for six months to three years.

Danielle: Yeah, until you find people to come to the party. But you know what we've never done on the podcast, is actually explain what the name is, Finding The Net. And I think I had this in my notes and I think it ties really well to what we're talking about right now, is so the saying is "Leap and the net will appear." So we are trying to find the net and that is a string that will build the net together. And I think I have this in my notes from when I wrote it down, and I might've said this in the last recording, so stop me if I did. I just genuinely can't remember. I was watching The Martian with Matt Damon and there's this scene at the end of the movie and he's back down on earth and he survived that whole ordeal, and he's pretending to be 20 years older or whatever and teaching at NASA.

And he's saying, "You just have to focus on the biggest piece of the problem and solve that and then move on and solve that and move on, and you can't bring your head up and focus on the enormity of, oh shit, this is going to go wrong. This is going to go wrong. This is going to go wrong." And obviously, it's a cheesy Hollywood movie, but I still think that's a good point of, okay, just focus on the next step. What's the next thing you can do? What's the next thing? And then after that?

Andrew: I love that, because it feels like yesterday to me, where I'm just looking at all of this stuff that we want to do and the product, and we're just on the next step in development, "Okay, we're just doing this step." And the design is much farther along, but it just takes time. And even in the process of developing it, you find stuff, you find things that you need to change. And you need to focus on that next step and keep focusing on it. But it is difficult because every once in a while, I think this definitely happened to me today or yesterday, I just looked at all this stuff that we're trying to get in and to build and what we want to do and it's difficult not to feel discouraged because you're like, "Gosh, this is taking so long." But that's how long products take to build.

Ian, the other day, I was expressing my impatience with, "Come on, how do we get this done faster?" Maybe Danielle needs these features so we could market this stuff. And what do we do? How do we do it fast?" And he said something like, it was some particular piece of the work we were trying to do, he was estimating it a month, and he's like, "Man, dude, if we can get this done in a month, that's awesome." He was like, "Products take forever. It just takes a really, really long time, a lot of effort, and a ton of skill to get it there." But it's difficult. Like The Martian example, it's like when you write a long to do list for a project, which is a very common piece of advice. Write out all the steps, and then what happens? I bet doesn't happen to you, it definitely happens to me, you write out all these steps and you're like, "Oh my God, this is so scary. I'm just going to go watch some TV or play a video game, because how am I going to do all that stuff?"

Danielle: Yeah. And then it just becomes so overwhelming that you're just like, "Maybe tomorrow." But if you're like, "Okay, I've just got to open a Squarespace account, get a landing page up, it'll take an hour, maybe less," and break it down into those little pieces, it definitely becomes much easier. But I think another challenge too that I've had at least, I mean, obviously, you haven't had the same one is that this is something that I do very much part-time and have another job. And just balancing that time is super hard. And that's definitely interesting because you were technically the only person on the team that's full time.

Andrew: Yeah.

Danielle: And I just wonder, how do you think about that in regards to, "Okay, we got to go faster, and blah, blah, blah, blah, blah"?

Andrew: Yeah. We're set up in a way structurally where, as you point out, I'm the full time founder, and then we have a group of, there's four different people who are involved on a part-time basis. I often ask myself the question, is this the right structure? Am I structured poorly? Am I structured in a way that's not good for the people who are working on it? Well, I do think about that, but my first concern, honestly, to be very honest, is this the right thing for the project? What's going to make this thing work? Because if the project doesn't work, it doesn't matter that it's not structured well for the people who are working on the project because there won't be anything to work if it's not structured well for the project.

So that's a thing, and then to expose what it's like from my end, there are challenging moments because all I do is think about this and there are moments when I am speaking into the void of the company, meaning everyone has other shit that they have to do, and that's how we're structured so it's a reasonable thing for people to be doing stuff. But every once in a while it's like, okay, we're halfway through the day. I've posted things on every channel. I'm very much wanting to drive this thing forward and advance this thing. There's only so many things that I can do to do that, and the team is off doing other things. And so sometimes I do ask myself the question, is this the optimal thing for the company, or should we be structured differently?

So yeah, that's a really different thing than what you were talking about, but that's some semblance of how it is on my mind. I don't think I've ever said that to you before. I'm curious if you have more questions about it, and then I would love to dig in on your end of this situation and what that's like.

Danielle: It's interesting because in my head I'm just comparing the two things of, oh, if we get this done in a month, that'll be awesome, because products take forever to build. And then we do only have a very small part time team. And I think taking a step back, we've done a lot in just a couple of months when you look at it as a whole. But that's a side tangent. Yeah, it's definitely tough because, especially just the nature of Slack too, which is where we communicate, I am in my full-time job Slack all day, because there's things going on and that's where my time is pledged and I can pop into Thunk and it's not really until later in the night. And I just also know myself with distraction problems, so I could get in there and get into a conversation, and then it's an hour or two hours where I was supposed to be doing something else.

But I think that's more the nature of collaborating via Slack where the expectation is instantaneous communication almost, like a Messenger or something. Whereas if you have something like the old fashioned email, it's like, okay, this is in my inbox and the understanding is that, okay, I will get to this in two days or so. I think the biggest thing with that for me that reduces that friction is expectation and setting those expectations. Hey, I can't respond to seven messages in Slack until a little later today because I'm working this morning, and those are that all comes down to also team management too and expectations of like, "Hey, this thing will be built by end of day," or, "I have a question. Please answer it by X." And I mean, that's something I do on Slack in general. I very much do it at my full time job where I'm just like, "Okay, what is the expectation and the timeline?"

Because it helps me reduce that stress barrier of, ah, it's on Slack, "I have to do it immediately," and get on the same page, which is I think super helpful in especially any remote work environment that we are all now in perpetuity living in.

Andrew: Yeah. In my humble opinion, this is a funny aspect of this, but we have the other challenge maybe of being like, "Okay, I'm going to have a part-time workforce," is that there's culture clash. So your company has a culture around Slack and Thunk has a different culture around Slack, and so those expectations are different in the two places.

Danielle: Mm-hmm (affirmative).

Andrew: And I think it can be probably confusing for the individual to be like, "Wait, what Slack am I on?" And, "What's the culture like here?" And that can definitely, well, I don't know, I don't know if that's something that you're experiencing. But I've found overall the thing that has been helpful and I'm like, "Okay, I feel like I'm misaligned with someone," is just saying it, just getting on a call and being like, "Hey, I don't think our expectations or something are aligned," and just hashing it out until we get there. It's not unlike a relationship where you're like, "Okay, we have to have a hard conversation here. Let's just keep talking until we get through it." And usually that does work eventually if you just calm down and say, "Well, here's what I'm seeing. What are you seeing?" and you get there.

But yeah, I think that is definitely a challenge of, I'm sure we could go deep on this, probably we need to have a longer conversation about this, because I actually think there's probably more learning I could do about your perspective and that you could do about mine that would maybe bring us closer together on how we achieve greatness together.

Danielle: Yeah, absolutely. And on that note about getting aligned, something that I actually loved earlier this week was when you had written that vision statement after we had given you our proposal of, "Here's the next month of work, here's what it looks like," and then you wrote back your vision statement of what it would look like at the end of the month. And there is just so much that gets lost in translation between what I think I said or wrote and what you think I said or wrote. And that's not anyone's fault,, it's just communication differences. And everyone listening, anyone in the world has had this issue. And for these big important things to be aligned on, that was something that I thought really helped close that gap and increase the clarity around, "Okay, these are the important things, blah, blah, blah, and we're very much aligned." Obviously, you can't do that for every Slack message, like, "My vision statement, once you read the Slack message will be."

Andrew: Yeah. I do think that that's someone's fault, and in this scenario, that would be my fault. So I feel pretty strongly that the person who is on the end of managing the project and bringing people in, it's their job to create clarity. It's that person's job to set expectations. It's that person's job to make it clear to the other person, "Here's what I'm asking of you." And I think that is lost a lot, really often, that, that is how that cookie should crumble. That's how I think of it. And very many times that I've been in situations, I spent most of my early career in the other end of that situation, and now I'm in a different side of it, and I think many times I had been in situations where the person did not make clear the situation that we were in right at the beginning, and that became very problematic, because I didn't know what reality was when I was, "Okay. I've been hired by this person and I'm supposed to do this thing."

And I can think of one particular time in my career, I had been working at a company, I was the first employee there, and they brought in somebody to manage the product and I had been doing that up until that point. And the CEO brought this person in and I asked the CEO, I said, "Is this person my manager? Do I report to them?" And they said, "Well, I think we're always going to be a really flat organization and they gave me this whole spiel."

Danielle: That flat organization thing, it kills me.

Andrew: Yeah, so I was like, "I don't really understand what my relationship with this person is." And then they started telling me what to do. And then I got even more frustrated and confused. And then I started scheduling one-on-ones with the CEO being like, "Hey, what's going on here?" And probably the third or fourth one of those, he was like, "Well yeah, of course, he's your manager. What do you mean?" And I'm like, "Well, maybe you should have told me that the first time I asked you." So yeah, I believe pretty strongly in that responsibility has to fall with the person who is bringing the other person in. You cannot hold somebody accountable to a clarity that you never created and the other party is not able to create that clarity. So, yeah, anyways, sorry I went on a, let me just step off my pulpit for a minute here, but I do feel really strongly about that.

Danielle: No, but it's true.

Andrew: And that thing that you mentioned, writing a vision statement, so that's a trick that immediately looked like it would work and I'm trying it for the first time. So we'll see if it does help us here. But I think that a lot of times, a founder or a manager will have this dream in their mind, they hire someone and they do have a vision. Even if they don't write it down, they're imagining what it's going to be like. Okay, "I'm going to hire this person and this is what it's going to be like." And they have a really pretty well formed vision because they're motivated enough to go hire somebody to fulfill this vision that's in their brain, but they oftentimes don't share that with the other party. And that's a trick I'm trying. We'll see if it's helpful. We'll see if it sounds like at least first reaction to it was positive.

But I can't tell you the number of situations where I realized I had hired somebody and they were really not living the vision that I wanted them to live and we had to have a conversation where I was like, "I'm sorry. Today's going to be your last day." And they were sometimes like, "What?" And I think that's a huge failure on me on so many levels. First, I didn't set good expectations and clarity around what I expected from you. And second, when you weren't living up to them, I didn't communicate that to you. And then finally, now we're at the end point and it's the third failure. There's so many layers of failure there. And I think that's something that I really believe has to be on whoever the leader in the situation is and they've got to make it clear. And you can't look to your people to say, "Why aren't you living up to the vision that I never told you I had in my brain?"

Danielle: Yeah, that definitely causes a lot of friction. I've been in that situation in work places before and it's hard, because you're just on the other end too. It's hard on both ends I think. It's hard to realize that, oh, I was not clear and I thought I was. This is on me. And then it's also very hard on the other end where it's like, "What? We had a meeting about this. We talked about it. We said we were going to do X, Y, Z. We've gone and done X, Y, Z and now you're saying they need to look like ABC. Where did that happen? Where did that come from?" I also believe a lot in writing and clarifying just because I think it is very helpful to have that record to reference back to. Not as any gotcha moment like, "I said this and you agreed."

But it is helpful when you're working on things to go back and be like, "Okay, so we did say this." And it is helpful in those times of clarity when you're like, "Wait, no, no, no. This is not what we agreed on," and then you can go back and be like, "Oh, I was wrong," or, "I was right."

Andrew: Well yeah, and that's obviously a very negative thing, if one of the parties starts using it as a gotcha moment, right?

Danielle: Yeah. Not the intention, ever.

Andrew: But I'm glad that you brought up this idea of the value of writing it down, because that is such a powerful step. And honestly doing it in this vision statement type format I think is really effective, because I can say I've certainly been involved in situations with contracts where we were in dispute about what was the nature of this thing and what was going on. And the funny thing is, here's why I think the vision statement is interesting, contracts, if you've ever been in a contractual dispute, you'll realize how useless a fucking contract is. By the time you're pulling out the contract. So much trust is broken at that point and so much bad communication has happened that we're just in a battle. And the things that are in the contract are oftentimes, it's also very, unless there's some legal enforcement behind it, even if there is legal enforcement behind it, it's difficult to get that right.

I think what's so powerful about a vision statement is it talks to the spirit of the relationship. It talks to the dream of the relationship, which sounds corny, but it's really what gets out of whack. It starts there. By the time somebody is pulling out a contract and pointing to clauses and reading terminology you're very far from the dream and the spirit of what originally attracted you to each other in the first place, right?

Danielle: Mm-hmm (affirmative).

Andrew: Because both parties are here for something that is a value to them, and it's not necessarily just a monetary exchange, but there can be a lot of complexity to why somebody would want to be involved with something. But yeah, I think that speaking to the spirit of how you want it to be, I don't know, I just think that's important and powerful and I hope to learn to do more of it and to do it better. And I'm probably on the newer side of leadership. I've probably been at management for a few years, but there's some people who've done it for 20. I sure as shit don't have as much experience as those people.

Danielle: Yeah.

Andrew: And this is the thing though, I think this is the thing that you're always working on, at least it seems to be to me so far, is you're always working on, how do I communicate clearly? How do I set good expectations? How do I address issues that are coming up? How do I speak in a way that allows for safety, but also gets us where we need to go. And part of it is also it's totally my responsibility to make sure the project does it die. And yeah, okay, right now, people lose a contract that's not the end of the world. It's not great, but it gets a lot more serious when it changes to somebody's health insurance and whole livelihood is riding on my ability to make sure that we're doing the things we need to do to make this company a success.

And that's something that I think, I don't know, I take very seriously and it means that I have to learn to be good at doing uncomfortable shit like saying to somebody, "Hey, we're not aligned. You're not doing what I need you to do to make this whole thing work." The truth is it should always really start from the places like, this is what has to happen for the project to go well, because the leader is truly responsible in my mind for the health of the organization, and secondarily to the health of every individual there, and then thirdly to see themselves and their own bullshit and interests. It's like first, the org has to be healthy. Secondly, everyone else has to be healthy. And what's the Simon Sinek book, Leaders Eat Last? That's my view.

Danielle: No, it's really hard. Leadership is the hardest thing in the world. And I also think that there's this gap of sometimes people get into situations in leadership where they think that hiring people is the answer and that it's going to reduce their stress and work, and it's actually so much more work to hire people. I'm not talking about this situation, just in general and other places I've worked at where it's like, "Oh, we need this person to come in and we need to hire them and blah, blah, blah, blah, blah," and they have all these expectations in their mind, but they don't share that. And then it gets to that point where you're just like, "Okay, they thought that this person was going to come in and fix everything that was going wrong in this one specific area," and they never shared that with them and then it isn't living up to the vision that they never shared and it ends up being so much more work and then you get into this cycle of micromanagement.

And all of that is just to say that it is very hard to be a leader, and it's also not something that is really trained. And it's one of the most important things in the workforce, is being a manager and being a leader. And it's really just something you have to learn ad hoc through someone or through books, which, I mean, I guess is a lot of how we learn now. But yeah, it's something that's very hard. No one trains it for you. And it's not something everyone's meant for. So this is our last episode of season one, and I am making a vision statement for our first episode of season two, that we're going to come back.

Andrew: Oh.

Danielle: And we are going to have a shit ton of users and really cool features and we're going to be on a roll. That's my vision statement.

Andrew: I didn't know you were making a vision statement. I'm very excited to read this. This should be very fun.

Danielle: No, that was my vision statement that I just made.

Andrew: Oh, that's it? You just made it just now?

Danielle: Yep. Yep. That was it. So that is my vision statement for episode one, season two when we come back.

Andrew: Love it. All right, well, thank you for listening to the final episode of season one of Finding The Net. We will be off hard at work making content, product, and marketing dreams come true. And we look forward to catching you in a month when we resume with season two. Bye-bye.