Natalie Nagele CEO of Wildbit

Episode № 7

Natalie and I talk about bootstrapping, learning that marketing is a necessary part of growing a software company, and the transitions that led Wildbit to be a family-focused company. We touched on the benefits and challenges of running a multi-product company, the inspiration for the various products, and the difficulties of hanging in there as a business gets older and the responsibilities grow and change.

Garrett Dimon: All right. We’re here today with Natalie Nagele and this is our second take because the recording stopped five seconds in. Natalie is the co-founder and CEO of Wildbit, makers of Beanstalk, DeployBot and Postmark. This is a little unusual because I actually work at Wildbit, and the team is so great.

Sifter intergrated with Beanstalk, used Postmark, loved working with the team whenever I encountered them for any reason. Once I decided to sell Sifter, I started talking to them. It was very, very natural for me to move over. I basically loved the product so much I came over.

That’s just a disclaimer, but we’re going to stay agnostic. Natalie, can you give a quick overview of how Wildbit came up? When the first products were launched, and the transition of where we are now.

Natalie Nagele: Sure. Wildbit, we just celebrated our 16th anniversary. We just threw a big sweet 16. It was started by Chris, who was 20 years old. Chris is my husband, and we run the business together. We started doing brochure sites, really small stuff locally in Philadelphia and then slowly grew it out of there.

Somewhere around 2004, 2005 we launched our first product, which is an email marketing product called NewsBerry that is no longer in existence. Then about nine years ago we launched Beanstalk, which became our largest product, version control system. Since then, Postmark and DeployBot, and that’s how we began.

Garrett: The biggest thing with Wildbit, at least to me from an outside perspective, is juggling multiple products. Many companies, obviously Basecamp, doubling down and focusing, and there’s a lot of teams doing that. What would you say are the advantages and disadvantages of running multiple products?

Natalie: I think Wildbit is a little unique in that we were not born out of a product. We didn’t have a product idea and then assemble a team to make it a reality. We had a team that was doing a lot of client work for us that then all transitioned to products work for those at Beanstalk. For Chris and I, we always say, “Wildbit is product agnostic. We exist for the team first.”

What that means to us is diversifying our risk a little bit and making sure that our priority is to be a company that is around, with jobs for all of us, for the next 10, 20, 30 years. For us, it’s a little scary to just say one product all in because anything can happen. This allows us to have our eggs in a few baskets and make sure that, no matter what happens, the team has a place to call home.

Garrett: It’s not just all upsides. Right? There’s juggling it. How do we manage that? What’s the hard decisions that have to get made and how does all that unfold?

Natalie: I think that’s one of the biggest challenges that Chris and I encountered. We’re still a small team. We’re 26 people. With three products, you end up really having to figure out how to focus our efforts. We’re still flat.

While we do roadmap planning and all of that stuff together, there is this, kind of just Chris and I, who are in a more strategic level for the products, see the bigger picture. It was easy with just Beanstalk and it got more complicated with Postmark, and even more complicated with the DeployBot, and we’re building a fourth product.

The way we’ve always managed it is that all of them are in different stages of their lives and have different needs technically. It’s like children. You can set one into a path and then you can turn your attention to another and then, hopefully, they all stagger that way where we can separate our attention to where it’s needed most.

The way we’ve always managed it is that all of them are in different stages of their lives and have different needs technically. It’s like children. You can set one into a path and then you can turn your attention to another and then, hopefully, they all stagger that way where we can separate our attention to where it’s needed most.

As Beanstalk has a solid roadmap and when we started working on Postmark, we delegated some of that strategic responsibility to some of the lead developers on that team. We didn’t abdicate, but we just allowed ourselves some free time to focus on Postmark.

We did that. Postmark took off. Now it has a dedicated product manager in Rian who’s now doing some of those strategic planning, organizing, all of that stuff, allowed us some time for the DeployBot and the new fourth product. It’s a work in progress. It’s not perfect and the flat part is probably making it the most challenging.

We’re thinking about that and thinking about where we spend our time and our resources ourselves as the team grows, and their responsibilities grow, too.

Garrett: One of the interesting things, too, with multiple products is how they come about, the genesis of the products. Is it a big plan? Is it not spontaneous but more natural and organic? How have the existing products led into the future products for existing from the beginning.

Natalie: To a fault a little bit, we like to build things. That’s how we got into this in the first place. We’re not sales people, we’re not marketers. We’re trying to get better at that, but not good at it yet. I think we like to build things.

NewsBerry was born out of a client need. Beanstalk was born out of a personal need, which was we were doing client project versus managing SVN repos. It was a pain in the ass, and that was history.

Then, we were running Beanstalk for a couple years. Chris and I, back then, were doing support. We would get support requests that were, “I invited my clients to Beanstalk. They never got the email. What’s going on?” Commit notifications, “I didn’t get my commit in an email and my digest.”

We quickly realized that, for applications, those transactional emails were blind. You operate totally blind on those. That was the birth of Postmark. For us, it’s a lot to do with wanting to build things and having a team that likes to build things. Also, just making sure that working on things that are fun.

We belong to this team, and we want to make sure that the things that they get to do every day are things that are exciting for them. We’re building a fourth product because we want to make sure the team’s excited and solving problems that they believe in and that they’re really passionate about.

Garrett: The other thing about Postmark, too, is that it didn’t just come up purely out of the need. It was, “We need this,” and, “Well, we have email experience from NewsBerry.” Even though NewsBerry wasn’t necessarily at the forefront, that experience helped lead into another product. They feed off of each other in a way and provide experience to create and solve those problems.

Natalie: Our problem with NewsBerry was Newberry’s audience was marketers, and we are not marketers. Especially back then, we didn’t even understand. That was like a bad word. We just didn’t understand the market. We totally lost it. We didn’t understand our customer. We completely misjudged it.

What was nice about Postmark was we took that email stuff that we knew really well, but built something for us, for developers, for teams building web apps. That, we know. That part, we get. That’s why I think it’s been such a success.

Garrett: One of the other challenges is this isn’t just simple little products. Sifter was fairly simple. If it went down, it inconvenienced people, but we bring it back up, and everybody gets back to work.

Something like Postmark for infrastructure, and then even Beanstalk, which isn’t quite up on the same level from an infrastructure standpoint, is still just absolutely critical to people’s day-to-day work. How do you do that when you can’t afford downtime?

People have to get up in the middle of the night. They have to drop everything and fix these things. It’s absolutely critical. But, at the same time, Wildbit’s culture is very much, “Work can wait. Take time. Go home, take care of yourself.” How do you juggle those two competing aspects, because it’s not easy running an infrastructure business?

The start for us has always been we have to build extremely quality products. There’s no compromising there. We’ve had QA from day one.

Natalie: Well, it’s terrible. Every time I say I want a new product or somebody brings up a new product idea, I beg them, I want to do a to-do list app. I just don’t want to be in the line of fire anymore. It’s tricky. The start for us has always been we have to build extremely quality products. There’s no compromising there. We’ve had QA from day one.

We don’t test in production. We don’t have our customers testing in production. We don’t release stuff and then figure it out later. We rigorously test every release. Obviously, things happen, but for the most part we rigorously test every release.

That has been extremely important because that sets us up for success. That sets us up for a calm working environment, instead of putting out fires, because code you’re releasing. You’re, at least, protecting yourself from there. Obviously, our thing has always been, “Let’s protect ourselves from things we can control because there’s always going to be things that are going to happen to us that we can’t control.”

In those scenarios, hopefully, we go through a long period of peace where, when we do have to put out fires, there’s a lot of reserves of stability and calm that happens, where the team rallies and we make it happen. We take the responsibility very seriously is what we do. If Beanstalk is down, people can’t work. That means they’re not making money. If Postmark is down, same thing.

For us, it’s all hands on deck when there’s issues. What we’ve been going through recently has been unusual for us in that Postmark is this fire hose of… We just were on the receiving end of this fire hose, and we can’t really control it.

What we have experienced over the last several months is this insane amount of growth that we… Again, it’s an infrastructure product. Growth, to us, is not like lots of sign ups. It’s capacity planning for physical hardware and all kinds… It’s intense. We were starting to feel a lot of anxiety as a team because we were putting out a lot of fires all the time.

What that translated to was pausing feature developments, so like, “All hands. Let’s get ourselves back to stability. Let’s get ourselves back to a place where we’re relaxed, and we’re in a peaceful environment, and we’re working proactively instead of reactively.”

We just redirected the roadmap and said, “Features can wait. Right now, the most important thing is to get ourselves back to a calm, peaceful place.”

That’s what we did. We just redirected the roadmap and said, “Features can wait. Right now, the most important thing is to get ourselves back to a calm, peaceful place.” You go through the forest a little bit, but that’s the only way for us to do it.

Garrett: It’s so easy to say, but then it’s so easy to put by the wayside once it gets difficult. When you think about it and you look at it all in the big picture, the healthier and happier the team is, the better they’re going to do on the product, the happier the customers are going to be. It’s this virtuous cycle of just good health all around.

I think it’s easy in hindsight to say, “Oh, we’ll just put the features on hold,” but there’s a lot of companies that simply wouldn’t do that. They would just keep trucking along, trucking along, trucking along, and building on top of the wrong foundation and then you’re going to have those problems. Everybody is going to be up in the middle of the night. It turns into a vicious cycle there.

Natalie: We’ve been doing this a long time. I’m sure there’s people out there who would argue with me, and they’re probably just much better at this than we are, but, for us, no feature is directly going to tie to some hockey stick revenue event.

If it takes an extra week or an extra month, it’s going to be OK. If you really think that this thing that you’re going to launch, if somebody launches it before you, it will destroy your business, then you’re not launching something innovative enough or important enough.

To us, we don’t make money on features, but we make money on customer experience. We make money on the promise that we make to our customers. Most of all, we do it because our team is brilliant.

They’re brilliant and they want to be here because they get to work in an environment where things are slower, peaceful. They get to work on things where they can really think and use their minds. That’s our responsibility. I can’t build a great product if my team is stressed out all the time. You build mediocre shit. I don’t want to build mediocre stuff.

Garrett: Moving on from technology, Wildbit is entirely bootstrapped and has been, and so going from zero dollars to millions of dollars in revenue certainly has inflection points and turning points where you’ve got to step back and be like, “What have we gotten ourselves into? What’s going on?” In hindsight, what were those key points for you? What caused them? How did you all get through them?

Natalie: There are a lot. Look at multiple… There’s two facets of this. One is understanding how to grow products. I personally think it’s easier to build than it is grow. Growing is one of those things that we’re learning as we go.

The one area is figuring out how to grow a product. That came a few years ago, where we built Beanstalk early on. The industry was very different back then. You did not have ProductHunt. You were not launching an app every minute, or every time a baby’s born, or whatever the crazy statistic is today.

We were very lucky that way. We didn’t have to focus on marketing. We focused on word of mouth, and building a really spectacular product, and integrations, and things like that. We grew it really successfully, but I think we got lucky and, a few years ago, realized that, “Oh, no, you do have to pay attention to competition. You do have to market. You do have to tell people about the stuff that you build because they don’t just see it.” It’s noisy out there. It’s really hard to just do that. I understand what go-to-marketstrategies mean now. Those ideas used to be something we would laugh about that now we realize is extremely important, and we’re just it figuring out. That’s why Garrett’s here. Right?

Garrett: Hopefully.

Natalie: We have to figure out, and that’s not in our DNA. That’s been our huge inflection point for Chris and I, and for the whole company, to understand that Postmark is, for some customers, a really large-ticket item.

Those customers want to talk to people on the phone. They want sales. Sales is not a bad word. Coming through to that and really growing, that’s been a huge growth pain, learning experience, inflection point, whatever you want to call it.

I think the second one comes on the team side, which you go from 7 people, 8 people, 10 people, 15 to 26, 28. It comes with a tremendous amount of new challenges and a lot of learning that Chris and I had to do on our own, but internally.

I think in the last year or year-and-a-half I understand when friends of mine or other companies that I know get bought or get investment and then the CEO gets replaced. I realized that it’s a very different skillset required from building something to growing something.

Chris and I had to go through a lot of personal reflection to understand. Like, “What is it that we want? What is it that we’re good at? What is it that the team needs from us now at this point?” Communication challenges, and working on multiple products, and making sure the team is happy and feels involved, but we’re not wasting time keeping everybody involved all the time.

That’s been really rewarding and extremely fun, but also super different than before. I think that’s what’s keeping us really engaged, is those new skills that we have to really learn and hone.

Garrett: If you could go back, knowing what you would be facing with those points, what would you have done differently?

Natalie: On the first challenge, I would have opened my eyes sooner, I think, and been a little bit more… Listened to people around me. I had lots of advisers who came from more traditional businesses who were like, “You need to sell. You need to market.” I’m like, “No, no, no, no. This is an Internet business. We don’t need to do that.”

I think there was a lot of comfort in what we had in growth and it was pretty safe and good. I wish I could go back to myself, my 2012 self, and be like, “What the hell were you thinking? You can’t just sit around. You’ve got to out innovate yourself.” We know that. We all read the books. We all see the stories out there, but somehow it just didn’t click. That would be a big one.

The other one, on the team side, I truly don’t know. Chris and I, about a year ago, we went through a whole process of understanding what we wanted to do with our lives. That was really important. Forever, we’ve done everything together. Every meeting, we were in together, every planning, every design conversation, every interview, everything together.

Now it’s obvious that was ridiculous. I wish maybe a few years ago we had had those conversations with ourselves. They were helped along with it — an adviser and all that. That’s what helped us grow up, but understanding those strengths and weaknesses.

It’s an evolving process, but understanding those and separating our responsibilities had a tremendous impact on the capacity of what we’re able to accomplish, how happy the team is and all of that. I wish it happened sooner.

Garrett: Yeah, absolutely. One of the things, it’s not just work and wait, but so much of Wildbit is just about a true work-life balance. It’s the kind of stuff that a lot of companies talk about, but don’t follow through on.

Now, especially having been at Wildbit a year, it’s very clear that it’s not just talk. But, there are times where living these values it’s easy to say, “Oh man, maybe we can just cut a corner here, let it slide.”

How hard has it been to hold yourself accountable for those values, and the rest of the team, and really stay true to building more of a family than just a pure profit generating business?

Natalie: I think in a lot of ways that’s a symptom of our own personal lives. We have two children. A lot of our team, we worked together for a long time and we all went through some of those life changes together, got married together, kids together and you realize very quickly what those priorities are. I think that’s really important.

That empathy is hard and I don’t judge people who don’t have it, because it’s hard to have until you have those experiences. To me, that personal feeling of like, “I want to go home and see my kids,” or like, “I want to be present at dinner. I want to be present on the weekends. I want to go on vacation, and be present, and spend the time.”

That, I think, really drives how we address everything, and experience, too. Somebody come and prove to me that rushing and getting it through on a deadline and releasing on Tuesday instead of Thursday is going to make a huge difference to my company. Until somebody proves that to me, I just don’t buy it.

For me it’s not worth it. It’s much more important for nobody to burn out, for people to feel value in the work that they do, because it allows them and empowers them to have the life that they want.

Work should be this thing that complements and provides you personal fulfillment, but also enables the bigger you — the you that writes books, the you that plays with your kids, the you that coaches soccer, whatever that you is — work has to enable that, not hinder that.

I think that’s a really important part and I’m honored in some way to be able to enable that for my team. I don’t know if that answered your question.

Garrett: It definitely does. Do you feel like it gets easier as time goes on to stick to those, or is it just case by case, every now and then there’s something that’s going to pop up and challenge something?

Natalie: I think now is a big challenge because there’s this middle ground or there’s this balancing act between… We’re all really trying to hustle. We’re on a verge of something at Wildbit, between Postmark, and the new product, and where things are going. I feel, sometimes, like we’re standing on a cliff and we got to take a huge leap.

That’s exciting but it’s challenging, because I’m thinking about work a lot more often than I did think two years ago. It’s personally challenging and I imagine the same for the team where they’re trying not to work on weekends or excited about stuff and there’s a lot going on, and we’re having capacity issues with Postmark, and that kind of thing.

I think it’s challenging because the core we all believe in. We all believe and we know it’s not just lip service. We know it’s true but, at the same time, we know that, in order to enable that environment, we sometimes really have to hustle.

I think that our values are so aligned on this team that I never hear complaints. I’m always the one like, “Stop working, stop working,” but I want to do this. I’m enjoying it. I want to enable the future of Wildbit. I know that this is what we have to do. I’m excited about it. I’m going to put in a couple extra hours or whatever that comes out to.

That part’s been really challenging to me to accept that and say, “You’re adult, and I trust you. We have the same values and I know that you know that I’m very supportive of you not working or not, whatever you need to do,” but, at the same time, allowing my team to be adults. If they want to work a little bit longer or really push something through, that’s OK.

I think right now it’s just a hard spot because we are in like a fighting mode right now, really trying to build something fantastic, really trying to grow, and really trying to do some awesome things. It’s not simple to do it in a 9 to 5.

Garrett: Yes.

Natalie: How much work did you do this weekend, Garrett?

Garrett: On my own stuff? Too much.

Too many questions in my head. I don’t know which way to go.

Another thing about Wildbit being bootstrapped and, obviously, you know lots of teams in similar places, similar sizes that have now raised money, had conversations with them. Do you feel like bootstrapping enables Wildbit to continue to be more different or do you feel like, at this point, it’s just simply, “We don’t need money to do what we do, and that would be just distraction?”

How has your thinking on all of that evolved as the company’s grown and matured and you’ve seen other teams as they decided to take that leap and raise money?

Chris and I have never raised money because we’ve never figured out a way to spend it.

Natalie: I don’t wear a badge about bootstrap. To me, it’s just never been something that defines the company, I think. It’s multifaceted question or, maybe, answer. I think, to some degree, Chris and I have never raised money because we’ve never figured out a way to spend it.

We have, obviously, had offers. It’s a long time to be in business, but every once in a while we sit down and we say, “If I had an extra million dollars in extra cash,” or, “If I had an extra five million dollars, what would we spend it on?” We do this exercise independently. We try to write things down. We don’t come up with anything worth more than a few hundred grand and then we’re like, “OK, done, not necessary.”

At the same time, I understand raising money comes in different stages in life. At the stage that you’re talking about — the friends that I have, at that stage — I really understand, and respect, and appreciate the desire to compete in bigger spaces, to want to just cash out a little bit.

People who have multiple founders… Chris and I are really lucky. It’s one founder, technically. All the money goes to us. All the relaxation, all those stress, it all goes in one. We have the same goals.

When you have a team that has three founders with three different places in their lives, with different goals, sometimes kids, I understand the desire to want to take some of it off the table. Take some of risk off the table, to cash out. I look at it on a case-by-case basis, I guess.

For us, it’s enabled us to move slower and to go for a pace that feels good to us. I don’t need a half-a-billion dollar company. I’m not being silly about that. I clearly want to make money, but I just don’t need to get to that point, and I think that’s fine.

Until I get into a market where the competition is so stiff that I feel like I can’t compete anymore, or I feel like we’re risking something, or Chris and I are just exhausted and need to get out, until then I don’t need it. It’s nice to be able to be in control and the only ones who…

Some people that I know have gotten some of the best investors ever. They’re awesome, and they’re kind, and their patient, and all that, but they are investors. They’re not grandma giving you money. They expect a return and that changes the trajectory dramatically, which is OK. It’s just I’m not there yet. I don’t need that.

Garrett: Absolutely. Bootstrapping or raising money, I think a lot of us — and at times myself included — get too dogmatic about it, when really it’s raising money and bootstrapping. Both of them are just strategies to achieve goals and, in the right context, they’re both powerful.

Natalie: To me, that conversation was always unfair because you’re judging people’s goals in that scenario. If you want to grow a billion-dollar business, you’re probably going… We’re not all MailChimp and Basecamp… We need to get out of that mindset, especially in a lot of industries you’ve got to…You need it.

That’s a goal — and that’s not a bad goal to have if that’s the goal your whole team can rally — then you need it. I think it’s not fair to say, “They’re assholes for raising money.” It’s like, “Well, you’re an asshole for not trying to grow big enough.” It goes both ways. To me, it’s your personal choice.

Garrett: I think the best analogy, Natalie, it’s just a tool. It’s a tool in a tool belt. You reach for it if it’s useful, otherwise… I think a lot of people probably, though — and it works both ways — they just get sucked into believing one way is the way.

People raise money when they’re probably should have bootstraped and people bootstrap when they actually probably could have raised money or should have raised money. Obviously, if you start out bootstrapping and get to a point where you have some leverage, then raising money is a lot easier about terms…

Natalie: I will caveat that, but I’m talking about growth stage. Where I get cranky is when people consider success is raising money pre-anything. That’s when like, “OK, that’s not really a success. That’s you’re really good at selling your idea and really putting together a nice PowerPoint deck.”

Again, that depends. If I was in biotech and wanted to… Yes, I have to think we’re very…There’s a term that I picked up from somebody that I love. Like, “SaaS businesses are capital efficient, extremely capital efficient businesses. You can scale it at a nice profit margin without having to spend a ton of money and that’s why you go into it. You’re selling widgets you need money.”

We’ve gotten loans, bank loans. I just go to traditional route where I’m like, “We manage all of our own hardware for our system.” You’re going to spend $200,000 on hardware? I don’t have $200,000 in the business five years ago just sitting there. You spend it on stuff. I got a line of credit. Spend it on that. That kind of stuff is OK, but that’s not what raising money is for.

That’s four percent. I own the entire company, and I paid it off in six months, and that was the end of the conversation. I think that’s an interesting business model actually. There needs to be a better financing for SaaS products because traditional banks…

Garrett: They don’t get it.

Natalie: No, they really struggle with it. They base financing on accounts receivable and I’m like, “People pay me up front,” and they’re like, “No compute.” Come on guys.

Garrett: Absolutely. No, it’s tough.

Natalie: Yep.

Garrett: Now I want to wind down with a couple simpler, softer questions. Looking back over all this time, what’s the single most difficult, stressful moment — it can be a week, a day — that happened that you could smile about now but, at the time, you really just were like, “How are we going to get through this?”

Natalie: How recent?

Garrett: As far back as you want to go.

Natalie: Forever?

Garrett: Growing the business, any phase of it.

Natalie: There’s outages. There’s been times when things have gotten really scary. It’s a long time running a business. Somebody got into our GoDaddy account and once held us hostage for our domain, so that was fun. I don’t think that was very scary, that was just fun. Well, it was scary, but not that scary.

We had an issue where Beanstalk, there was this RAID controller that just kept dying and Beanstalk would be down for hours. I remember staying up all night, literally for 30 hours, just trying to do support. That was a little scary.

You see your whole business there and you’re like, “Are people going to stand by you?” Especially a young business like that. You’re like, “Are people going to stand by us? They’re all going to jump ship. Everything we’ve built is gone in one second.”

I think the hardest, I will say, is we’ve been doing this a long time and there’s definitely a point where you get tired. The scariest, hardest part is thinking that through. Having those conversations with yourself, with Chris, like, he’s been doing this for 16 years. I’ve only been doing it for like 13.

There’s definitely times over the last couple of years where he was just tired. It was like, “Can’t do this alone, I need you to…” or the other way around. I think those are the moments that I think are really intense, because you feel internal pressure. I can’t just walk away. I have a whole team, and I feel like we have unfinished business.

Understanding that it’s in our control, and that we can figure it out, and let’s figure out what we want to do, what we love to do, and that we get to do it because that’s the whole point of doing this in the first place. Those conversations get really hard for a while and really dark and then you come out of them, I think, in a much better place.

Garrett: On that note, what is it that you love about the business? What is it that pulls you through those moments that get you out of bed in the morning, excited to work on the next thing?

Natalie: I love the people I work with and I love the challenges that it brings. That’s definitely the first priority, but I know that sounds really cheesy. Honestly, personally, I’m being challenged in a way. I’m being challenged for the first time in a long time to push myself personally, to get past some of the stuff that I was really comfortable doing.

I think that personal challenge to get pushed enough to where I think they can get it, create this incredible environment where people are just doing it our way and we’re able to have a great business, it’s profitable, but people are happy and calm.

Just proving that to myself that we can do it, that we can do it in a way that makes sense to us, that can be sustainable for a long time feels really good. That kind of intrinsic motivation is really what I get up in the morning and do.

This is going to sound really silly, but when we came up with titles and it was officially like, “You’re CEO,” which means you got to get shit done. It didn’t change my… well, it changed my responsibility, but it didn’t change the way my team looked at me, but it was personal like, “Oh, I’m really responsible for this stuff.”

It’s like, “Chris is waking up,” and like, “I gotta run this product. The systems, the operations that has to be brilliant.” Waking up that next morning, I realized and like, “Oh, that’s my challenge,” versus like, “The whole world is my challenge. That feels really overwhelming,” and all of that.

I get up in the morning and I get really excited about what else can I do today to get us where I think we can get, where I can prove to myself that we can do this.

Garrett: Fortunately, it’s a challenge that never ends, it just changes.

Natalie: Dramatically.

Garrett: Yes. I think that was the biggest lesson is. You mentioned earlier about being on a cliff and having to jump, but I feel like that’s just constant. As soon as you jump, you just realize, “Oh. Well, there’s another cliff.”

My struggle, early years with Sifter, was I always thought, “Oh, we’re there. I’m gonna be able to relax. As soon as I ship this, I’m gonna be able to relax. Things will be in good shape.” There’s always something else that you can improve, and it’s hard.

I think it was Amy. She had a sketch that she had somebody do and it was basically, you have to enjoy living with everything being 80 percent done all of the time, because there’s always more you can do. It’s tough to do that and be at peace. There’s always more to do in that challenge. I think that’s a good way to stay motivated. At least you’re more responsive.

Natalie: My whole team feels like that. That’s the curse of the knowledge worker, is that you don’t turn the machine off at the end of the night and go home. There’s always a little bit more. You can write a little bit better. You can write a little bit more. You can edit better. More tests you can run. All that stuff.

I think our responsibility to ourselves is to create those starts and stops. You know my whole feeling on all of that. I obsess over time management, and finding time for deep work, and to truly understand and direct yourself in where you’re going and what you want to do, so that you can have that peace of mind at the end.

Garrett: Awesome. That wraps up all of my questions. Is there any parting wisdom you’ve got for anybody else coming up, about launching an app, wanting to launch an app? Don’t do it or…?

Natalie: [sighs] I was at a conference — this is going to sound so sad — I was at a technology conference that will not be named, and I turned to somebody from our team, and I was like, “If I had to start today I would second guess it.” Then I realized very quickly it’s a very busy, it’s a noisy place, and it is filled with a lot of crap right now.

I think, if you truly want to build something that’s amazing and sustainable, take the time, figure out what it is, and just do it the right way. Don’t do it because somebody wrote about it. Don’t do it because whatever. Do it the right way so that we don’t fill our industry with a bunch of crap. I left that conference really disappointed with the garbage that people are building out there.

There’s not a software industry any more, everything is a software business. I just want to make sure that we’re filling space with the things that matter. That doesn’t mean we have to save the world, but just thoughtful, caring, and you get to build your business you’re way. I think that’s the important thing.

Garrett: Right on. All right, thanks for taking the time to do this. I appreciate it.

Natalie: Thanks, Garrett. Bye.

Garrett: Yeah, of course.

Natalie: Bye, everyone.

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