Jaimee Newberry Founder of Picture This Clothing

Episode № 22

Jaimee Newberry is the founder of Picture This Clothing where you can print a coloring sheet and design a one-of-a-kind ready-to-wear creation that they send to you. In this epsode we talk about making hard decisions and creating space in your life for ideas to take hold and give you time to work on them.

Garrett Dimon: We’re here today with Jaimee Newberry of Picture This Clothing. How are you doing today, Jaimee?

Jaimee Newberry: I’m doing great today, Garrett. How are you?

Garrett: I’m fantastic. Can you start off, give us a little bit of background, tell us about Picture This Clothing and your history and how you got where you are today?

Jaimee: Boy, a long story. I’ll give you the quick. Picture This is, it’s the opportunity to wear your imagination, very simply. You print a coloring sheet. Kid designs it any way they want. We do adults too. Design it any way you want, and we make it real.

I’m wearing an example today. It’s this magical experience. It’s not just a shirt or a dress. Anyway, how we got there is quite, I think, an amazing story. There’s the short version that we share online with everyone, but sometimes when the story gets shared, a lot of the history gets lost.

Over the course of about eight months I burned out. I hit this crazy burnout. I ended up leaving my job. My partner was working on his own stuff.

I think that there’s so much important stuff in what happened before. When people see Picture This Clothing, they learn the story, “Oh, they went viral.” We went viral on the day we launched, which is a weird thing, but I’ll get there. There was so much that happened before that.

It’s not like instant success. I think to get started, if you go way back to around 2012, 2011, 2010, in those years, my partner in this company, I have a couple partners, but my co-founder, Ken Finney, and I, we’re partners in business, partners in life.

He was having his own set of challenges back in that time window with physical stuff, joints. His joints stopped moving. He was in a wheelchair for a while. He couldn’t walk. We didn’t know why.

We were going to doctors trying to get diagnoses and nobody could give him an answer. It seemed to be getting worse and worse and worse. In around the same time period, I lost my dad in 2012. I was working in a job that I quite liked, but it caused me to disconnect with the work.

I had a background as a designer. When you can’t connect with your work as a designer, you probably shouldn’t be doing it anymore. Design is an emotional and engaging thing.

That was what my work was all about, was helping companies create engaging and emotional experiences, not just products. When I felt that disconnect in my own life, I felt like I couldn’t do it anymore.

Over the course of about eight months I burned out. I hit this crazy burnout. I ended up leaving my job. My partner was working on his own stuff. I’ll let him tell his story another day, but through all the physical stuff. Meanwhile, I was trying to figure out not so much what’s next for me.

That was an important question but what’s important to me was where I placed all my energy. It was not what’s next. It’s what’s important. When I put my focus into that, it was all about my family. It was all about, “Yes, I want to be able to support my family and stuff but…” Take my earrings off. They’re clinking.

Garrett: Don’t worry.

I was like, “What if I design my life the way that I design products? I think I can use the same process.”

Jaimee: That’s the thing. It was all about trying to figure out, how do I prioritize what’s important to me and make all of those decisions? All the decisions that affect everything I do every day as a career, as a mom, as a girlfriend and align these things toward what’s important. Once I started doing that, and I don’t want to oversimplify it, I started designing my life as a product designer.

I was like, “What if I design my life the way that I design products? I think I can use the same process.” It turns out you can. I started using that process. Anything I would do to a product working with a client to help them build something, I pointed that at myself and said, “What are my values?” If it’s a product, it’s design principles. For a life, it’s core values.

Once I started doing that, these things just started happening. I ended up sharing my story, “Through Burnout and Back Again.” I got invited to speak all over the world, sharing the story, Through Burnout and Back Again.

It evolved. It evolved into something called, “No Excuses.” I started telling that story out in the public circuit. It was a chapter two. If you’re, at all, into digital products or technology, the first was get your minimum viable product out. That was my Through Burnout and Back Again. Then it’s iteration and features.

My “No Excuses” was how I started practicing iterating through what was working, what wasn’t working in my own life. What unfolded is I became a coach instead of a designer. I was coaching people who were going through burnout how to work through it and how to overcome it and come out on the other side. Whether that’s a career change or whatever. Different for everyone.

I was helping people. That meant a lot to me. I was helping them through the experiences that I had gone through. Because I’d created more space in my life, I created this opportunity.

That parlayed into going back to my roots as a designer but in a different role where I was now advising companies. I would come in and help companies with their teams, team engagement, and parlaying that into…I believe that human beings are the connective tissue between products and human beings. There are products that are the connective tissue between humans. You’ve got humans on both sides.

I made that my life’s work. One of my…what’s importance was to build more space in my life. That meant I want to have more time to spend with my family. I want to do work that I love. Don’t we all? We can’t always do everything we love all the time. I realize that but I started shaping things. I was doing stuff that I loved.

I was helping people work through problems, create more engaging products, emotionally engaging products in a new way that I hadn’t done before, just as a designer, not that there’s anything wrong with being just a designer.

I was helping people. That meant a lot to me. I was helping them through the experiences that I had gone through. Because I’d created more space in my life, I created this opportunity. I was hanging out with my kids.

My daughter, one Christmas break she’s home from school, as kids are on Christmas break. She draws this picture of a dress. She brings it to me. She’s six, almost seven. Just about to turn seven at the time. She brings this drawing and I look at it.

I say, “Oh my gosh, I could make this.” I’m working from home. I’ve got a little bit of time. I can do this. I can arrange my time the way that I want to because I work from home. I was like, “I can make this dress. I have just enough sewing skills to make this happen.”

We went to the fabric store, spent about a hundred bucks, which is a lot. About a hundred bucks on supplies and materials to make this dress happen. About 12 hours over the next three days, I was able to cobble this little dress together. I put in on her when it was all done.

She says, “I’m wearing my imagination,” which was this magical moment in parenthood. She wears it. She wears it for the next three months. I have to peel it off her to wash it. Everywhere we go, people are like, “Where did you get this dress?” It’s this bright, rainbow, crazy dress. “Where did you get it?”

She’s like, “I designed it with my mind.” It was magical. The response from people was so cool. My boyfriend, Ken, he’s like, “You have something here. There’s something here. You have to do something with this.”

I was like, “No, I am not going to sew these. I’m not going to do that. I don’t want to be a seamstress. Not what I want to do. I’m a tech person.” We shelved it. We did a little business plan around it, though. “What if we did? What would that look like? We could outsource the sewing if you don’t want to do it. What would it look like?”

It didn’t make sense so we shelved it. After it ruminated, I think with Ken, for a few months he came back a couple months later and he goes, “I think I’ve got it.” He’s like, “What if they just wore the drawing? Instead of trying to recreate it we print the drawing. We use sublimation printing. We create a special pattern that looks just like a coloring sheet.

“Something super simple that a kid can understand and we turn that into their drawing. It’s exactly what they drew. We don’t modify it. We don’t filter it with our adult minds in any way. It’s what they drew. It’s pure.” That is what resonated.

That was like, “Yes, let’s do that. That I can get behind.” That was probably six months or so after she first wore that dress. We invited a friend of ours, Stefan, to help get logistics and figure out what we would need to do to get this done. We called our friend Iggy, who is a great designer, owned his own agency.

In exchange for equity, as long as he could do it in his free time, he did our website. We worked with Iggy. We worked with Stefan, Ken and I. We started working on prototypes and making it all come together. About 10 months later we had a website that Iggy says, “OK, I think it’s ready to go. Let’s test it.”

We tested it with about five people, got a little feedback. After we made those adjustments we were just at a place where we were like, “Well, I guess we just need to let the world know we have it, that there’s this thing that exists that we made.” It was intended to be a proof of concept.

We did it in our free time. We didn’t pour a lot of money into it. We put some money into doing prototypes and developing a template. We did just dresses to start. We did just dresses because, again, proof of concept. We learned, along the way, as we were doing the pattern development and stuff that T-shirts were a lot more time consuming and a lot more expensive.

We thought, “Let’s just see if people will even do this process of going to our website, printing out a paper, going away, coloring it, and then taking a picture and coming back to the website to place an order.” We didn’t even know if that was logical.

It was one thing after another. We didn’t actually see sales for the first five days.

It made sense to us but would people really do it? I posted a tweet. It was 6:22 AM. I will never forget this because this tweet changed my life. It was 6:22 AM. It was August 17th, 2016. I posted a tweet that just said, “Hey, check out this thing some friends and I made,” and the link to picturethisclothing.com.

It automatically popped in the little picture from our Home page, which was my daughter and her best friend holding dresses that they had drawn and they’re wearing them. By the end of the same day, we got a write-up in TechCrunch. It was funny because they didn’t tell us they were doing the write-up.

We got an email from TechCrunch, from a writer from TechCrunch. It asked a few questions. I answered them thoughtfully, thinking, “Maybe they’ll want to do a story on us.” Within 30 minutes of me responding we noticed a lot of traffic. We noticed our website crashed. We saw that somebody had written about us. TechCrunch did a story.

The next day, and then the next day…It was one thing after another. It was TechCrunch, and then Product Hunt, and then Disney’s babble.com, which is a parenting blog, reached out to do an interview.

Another company reached out to do a Skype interview. They made a video. It was one thing after another. We didn’t actually see sales for the first five days. That was interesting and something that not a lot of people know.

Garrett: Scary, probably, too.

Jaimee: It was one of those things where, like, “Aha! I’m glad we didn’t put a lot of money into this up front because maybe it is a great idea and it’s getting a lot of buzz but why is nobody actually doing it?”

What we learned, though, is it takes a minute for people to come up with their designs. Once that Disney babble.com article went live, which was one full week after we launched, that’s when we started seeing sales. We had a few friends who were like…They’d placed orders for us. Super cool friends, thank you.

It was one of those things where we saw maybe three or four sales a day there for the first few days. We were like, “Cool. This is something we can sustain.” We all had day jobs anyway, owning our own companies, doing our own things. We were not really looking for a new full-time gig, per se. We just had this idea and we knew we had to get it out into the world so we made it. We did it.

We realized our sizing was a little bit funky. We had things to tweak really fast. Then we started shipping. Man, it just never stopped after that.

Then it went viral. Another two weeks after, one of the interviews I had done, they had posted their video. It was the day before Labor Day. This is where we saw sales. It was like, “OK, concept proven.”

Their video went viral on Facebook. It got three million views in less than 24 hours. Three million. I was like, “Oh my gosh.” The next day we did $10,000 in sales in one day. That was going from 0 to 100. It was awesome. We were like, “Oh my gosh, we haven’t even shipped a single product yet.”

We were ready. We were getting stuff going but things had been…We had a few kinks to work out. We realized our sizing was a little bit funky. We had things to tweak really fast. Then we started shipping. Man, it just never stopped after that. It kept going and going. We were right at the start of the holiday season, too.

That viral video, from there we were invited to HLN…HLN, it’s a news channel. They have a show called Michaela Morning Show. They invited us out to LA, put us on their morning show, got to talk about it. That was super cool.

Then Harry Connick Jr. has a show called Harry. They invited us. Flew us out to New York. Did some interviews. We got to be on Harry. One was in October. One was in November. Stuff like Ashton Kutcher had posted about us. He had seen it. He retweeted, “Here’s a cool idea.” George Takei posted, “Wow, I wonder if I could wear this,” about the dress, which was super hilarious and awesome.

More videos started getting made. This was a funny thing, too. We started getting reamed for only having dresses. People were like, “Oh, you’re sexist.”

We were like, “We didn’t know we were going to go viral. We didn’t make these videos.” The videos were awesome but it pushed the focus on the dresses. We worked really hard to get our T-shirts out. It was one of those things where we were, with three people, trying to manage all of these orders and all of this craziness while also trying to develop a new product in parallel.

That was a big challenge. Ken really nailed that down. We couldn’t have done it…I can’t imagine having trying to work through that with anybody else. Boy, it puts a lot of stress on your relationship, too. That’s something.

I’ve talked about all this amazing, incredible stuff but there were a lot of difficult challenges that came out of that. You have to learn a lot really fast. None of us have clothing background.

We understand these things but it was our first time actually running our own e-commerce company. The stress that happened with that volume, I can’t even capture. I don’t know how to communicate it. It was so stressful.

We’ve done e-commerce stuff from the technology side before. We worked at Zappos. Ken and I were both a part of the very first mobile apps at Zappos. We were a part of that team. It did super well. It was great.

We understand these things but it was our first time actually running our own e-commerce company. The stress that happened with that volume, I can’t even capture. I don’t know how to communicate it. It was so stressful. It started taking over our house, for one.

We had a local manufacturer that was 15 minutes away. We did that because, again, proof of concept. We didn’t want to invest in huge machines and stuff to get started. We found somebody who could print, cut, and sew locally 15 minutes from our house, great job, and manage the volume.

Once we got into a groove, we were in good shape that way, but I would run down and pick up these massive boxes of 400 items, take them back to my house, photograph every single one because it’s one of a kind articles. We had three different systems. There wasn’t one system that was built to manage one of a kind articles. That was a software learning curve there.

Every order that we were processing has the image processing side, which was all Ken, and then the packing and shipping which was all me and then Iggy trying to keep everything up and running. The website crashed that one day. It crashed again a few days later.

Trying to get that stable because we had built it…It’s a well-built website but we used a lot of plugins and stuff to get it customized the way we wanted. You learn a lot really fast that way.

It seemed like every problem we would overcome, two more would crop up. It was that scenario of trying to plug holes on a leaky boat.

With all these orders and things, stuff taking over our house, I’d reached a point of being so stressed out I actually told Ken at one point, “You’ve got to move out.” I was serious. We were like this a little bit. So much stress in trying to solve all the problems that cropped up.

It seemed like every problem we would overcome, two more would crop up. It was that scenario of trying to plug holes on a leaky boat. You’d plug one and then four new ones sprang. It was like that for six months, without stopping. Then it finally started to slow down. We were grateful for the slowdown. I feel like I haven’t let you lead.

Garrett: I’ve been taking notes to make sure. I’ve got a whole bunch here. There’s so much interesting layers of this to unpack. Leading into it, one of the things that I’ve noticed over the last couple years, we just moved. We’ve been going through a bunch, too.

So much of it seems like it’s about making deliberate choices either to open up space or all of that. In this case, those choices are what led you and gave you the space to come up with this idea. Going viral, that’s everybody’s dream, right?

Jaimee: It’s everybody’s dream until…

Garrett: If you build it, they will come. I spend all my time telling people that doesn’t happen. It generally doesn’t but…

Jaimee: It usually doesn’t but I believe we had something special and we executed it well.

Garrett: I think everybody thinks going viral, in terms of…It’s a good problem to have, growth, but there’s a lot of baggage that comes with that in that you have to scale fast, quick. Any problems you have are amplified. The pain of dealing with those issues.

Like you said, plugging a leaky boat. It can overwhelm you, whereas even though that’s what everybody wishes for, it’s be careful what you wish for.

Then, all of a sudden, this great idea that we made, our idea baby, comes into the world and it was like a wrecking ball, just knocking me right out of my game, basically.

Jaimee: It happens. It’s funny, because with that whole…The thing that led up, I had reached this space when I made that dress, that very first dress for Zia, my daughter. I had created this really comfortable, delightful life. I was actually working remotely as a COO for a company called MartianCraft. It was a tech company. They were a coaching client and it rolled into something more.

In February of 2016 I had accepted their offer to become their COO. Again, it was a remote position but I was full time. I had accepted a full-time job for the first time in four years. I had been doing my own independent thing and creating my time. I’d created this perfect little situation where I owned my time. I had a nice, great position at a great company I love, still, today.

Then, all of a sudden, this great idea that we made, our idea baby, comes into the world and it was like a wrecking ball, just knocking me right out of my game, basically. Off my chair, through the wall.

I’m not complaining. It’s not a complaint in any way. It’s a reality of, “Oh my gosh, you think you’ve got a lot of plates spinning and then throw a viral idea into the mix.” A viral thing comes with a lot more than just great sales. It comes with 200, and I’m not exaggerating, I was getting 200 emails a day for at least four or five weeks.

That was the first thing that we did was hire somebody to come in and help me manage emails. I needed somebody that had the right voice and that had the right care. In customer service they don’t take lightly. It’s a very serious thing.

With this company and with our brand, it had to be the right person. Amy, we brought in, somebody we knew and had worked with before. Amy came in and helped be that voice and extend that beyond me so I could then focus on packing and shipping.

I was able to actually bring my sister in to help with packing and shipping and relieve some of that stress so I could help focus on the growing and not kicking the love of my life out of my house. It’s crazy, the stress that it brings. I ended up….I had to quit my job, actually. I couldn’t manage two full-time jobs and be a mom and all of these things.

I had to make a choice. I chose…This is, I think I said, my idea baby. This is the baby that I created. I’m going to go with this, ride it ‘til the wheels fall off. I hated to leave MartianCraft. I love MartianCraft. I have so much respect and love for those guys and women, boys and girls.

While it’s slow and while we’re trying to figure out now, what do you do? The viral is gone. The viral may not ever happen again. Don’t ever expect lightning to strike twice.

For that team, it was hard to leave but I knew it was what I had to do. When you leave, you’re leaving a reliable income. You’re cutting that cord. Yes, we’re making a lot of money but you’ve got to put a lot back into the company to make it grow. People were like, “How much have you made?”

We passed a million dollars in sales earlier this year. In less than two years we did $1,045,000. We’re coming up on two years here in August. Excited. Sales have definitely slowed down, but this time of year we had equally slow this time last year and we still came out awesome at the end of December.

While it’s slow and while we’re trying to figure out now, what do you do? The viral is gone. The viral may not ever happen again. Don’t ever expect lightning to strike twice.

You’ve got to figure out how to leverage that because if you don’t, it will just fizzle out.

Garrett: I imagine that’s almost a challenge unto itself in that you grow so fast and then, all of a sudden, that source dries up a little bit and you have to figure out, “How do I do this under normal circumstances?” and operate under those scenarios. That’s a whole new challenge. You’ve got to learn all over again.

Jaimee: I think something we did well and I feel good about is that we had money. We were making money. We had set the company up to be profitable from sale one because we were outsourcing that manufacturing. People place the order. They’re paying for it in full. Then we pay for the work to be done.

It’s basically building some capital, but then, also, we didn’t pay ourselves until tax time. When we paid ourselves, because you just earned a bunch of extra money, somebody’s got to pay taxes on that. Don’t forget about taxes.

I think that’s where a lot of people get into trouble, is they want to pay themselves. They want to reward themselves for all the hard work. There’s money in the bank account but you’ve got to look at, “We owe taxes on this. We’re going to want to plan for what happens if it gets slow.” Make sure we’ve got six months of runway.

We did do that. We did that. I feel like I knew enough about finances. I’ve never had debt in my life and I don’t want to start now. That was important to me and to our team. I think that’s one of those things that if we had done wrong, it could have squashed us.

Another thing that we did right, despite the angry hate mails about being sexist, if we had launched with T-shirts, the order volume would have killed us. I think it would have doubled our order volume right out of the get go. We would have squashed ourselves.

You hear about those stories, too, where you can’t keep up with the demand and you run yourself out of business that way. I think a lot of people are like, “Oh, they’re crazy. They didn’t do it right the first time,” but I believe we did it right the first time. I believe launching with one single product, nailing it, and then expanding was the right way to go.

Garrett: It’s so easy to be an armchair quarterback, right?

Jaimee: Isn’t it?

Garrett: It’s almost an easy, favorite pastime for everybody to sit back and say what you should have done.

Jaimee: Exactly, and that’s really…When I was talking about all the things that come with going viral, there’s the email volume. There’s the social media aspects. Making sure that you’re answering those questions that are out there and fielding the comments, not being defensive, knowing which ones to answer and which ones to just let go of.

The ones that you answer, you answer heartfully. You don’t answer them defensively or angrily because it represents your brand in every way, every touch point. I think we took a lot of care in those actions. It’s hard sometimes. You care about your thing that you made. You love it. It’s hurtful but you gain a thick skin.

Garrett: You have to. You really do. We’ve accidentally covered most of the things that we wanted to touch on. From a software operations logistics standpoint, are there any kind of recurring problems that you currently have or have recently had that you either neglected when you should…Not recurring problems, necessarily, but recurring tasks.

Things where, looking at it in hindsight, you’re like, “Man, we should have sat down a month ago and spent a week fixing that problem because now we’ve spent so much more time just duct taping it together.” Are there things like that that you wish you had just invested more time in doing right up front?

Jaimee: There are. If you can go back, there are always things you could change. I think there are things that we constantly learn along the way. I guess if we could go back and do something different, we probably would have built the website a little differently.

We used WordPress templates. We used a lot of plugins. When one plugin does an update, it breaks everything else. That was a challenge. At the same time, we have a pretty good website. It’s pretty solid. At least we did the best we could working on a pretty lean budget and that sort of thing.

I feel like most of the stuff that comes up…we did a few things the wrong way. We went back and did it again. I would love to remove those wrong ways out of all of the equations but I can’t. We learned a lot from doing it wrong, a few things.

There are a lot of tasks that we have automated and have been able to operate things really leanly, again. We spent a little more trying to fix things certain ways where if we had just approached it in a different way…I don’t get too specific because we have a lot of trade secret stuff in our process that I can’t share. A lot of it has to do with that.

The trade secret stuff that has been developed is amazing. I feel like our team has risen to the occasion of when there’s a problem let’s see what exists out in the world. Is there something that we can use and bring in or is it something we need to create from scratch?

There have been some instances where we just have to do it from scratch ourselves. I don’t always recommend that but sometimes it’s the right way to go.

Garrett: One of the things I try to talk about with people a lot is automation. Everybody has processes or problems in their business they hate. It drives them nuts. That first thought is, “Let’s just fix this forever,” as opposed to, “Here’s where I’m doing everything by hand. Here’s perfect automation.” It’s a spectrum.

You can inch towards that perfect automation but if you try to jump to it, like with software, you’re going to build the wrong thing. You’re going to automate it incorrectly. You almost need that pain. You need things to be crumby and miserable so you learn how to do it correctly when you do automate it.

Jaimee: I think that’s so on target. I couldn’t have said that better myself.

Garrett: Like WordPress. That was probably a good decision, right? That’s what got you live to validate the idea. Now, you may want to circle back but it got you here. You may not love it but it worked.

Jaimee: I don’t hate it, either.

Garrett: Too often we get this idea. “Oh, no. This isn’t good enough to launch.” The reality is you don’t know if it’s good enough to launch until you launch. If the launch goes bad, you can launch again. It’s not fun but the reality is you can.

We could have waited another six months until we were ready with T-shirts or we could just get the idea out and see if it was worth spending the time, another six months on T-shirts.

Jaimee: That’s so true. I think, going back to that, why did we only launch with dresses? It was, why not just add T-shirts? T-shirts were a lot more expensive and a lot more time consuming because we cut and sew everything. Colors have to be aligned and the artwork, the sleeves.

If we were just stamping on pre-made stuff, you’d get missing patches where it wrinkles and folds. It’s just not good quality. We wanted the quality to be there, because kids, when they design something, they care. They care that it looks like what they created on purpose. We care about that. We want to give them that.

Those things, we started with something that we knew we could do and just test. If we had done it in any other way, we would have regretted that. I think starting small and starting focused is exactly the right…the more focused you can be…

We could have waited another six months until we were ready with T-shirts or we could just get the idea out and see if it was worth spending the time, another six months on T-shirts.

I feel like those are lessons that we’d learned through experience with our other jobs and other work history that we had. We knew that this is enough to get this idea out the door and see if it works. I think that you brought up a great point with that.

Garrett: I think it’s important for people to see just how messy it is, getting something off the ground like that. You’re not just going to launch and then everything’s going to be perfect and you’re going to cash checks. You’re going to launch and everything’s going to be really painful. You’re going to fix that and then something else will come up.

Jaimee: It’s a lot of work.

Make sure that you know what your lifespan is, I guess, if you’re going to make that commitment to jump.

Garrett: It’s a constant game of optimization and making decisions. There’s always something else to improve. To me, being messy like that in a good way. Not messy like bad, but messy scrappy is the word we use a lot. It’s the way to do it. It’s uncomfortable. I think that scares people away, but it’s the way to do it. Sometimes it’s not going to work.

Jaimee: I think you always have to have a reality check every once in a while. Sales are slow right now. If we hadn’t seen…let’s go back a year. Last year, sales started to plummet after the whole viral thing went. Sales just went whoomp. While it was paying for itself, we weren’t paying ourselves.

We thought, “We paid ourselves enough to cover taxes.” We were good there but still not bringing in a salary or anything. We quit our jobs and stuff, some of us. It was like, “What do we do here?”

Make sure that you know what your lifespan is, I guess, if you’re going to make that commitment to jump. I made that jump. I had built a pretty good safety net for myself just from my prior stuff. I knew I wanted to always allow myself the freedom to say no to anything I didn’t want to do. I’d worked really hard to build up a nice savings nest egg.

Yes, I’m chipping away at that right now because we’re not paying ourselves but I think that everything we’re working toward in this company, I will believe in it until it gives me a reason not to believe in it.

These slow sales that are happening right now, exact repeat of last year. If we can at least do as well as we did last holiday, I know we’re good for another year. I’m going to keep riding with that. If I’m really smart and I scale my needs back to just enough. I don’t need anything fancy, I can ride this wave. I can ride the downs. I can be prepared for that.

The downsides happen. I think that sometimes when thing are going really, really great you’re like, “Oh, yeah. We don’t need PR. We don’t need advertising. This thing sells itself.” Don’t get overconfident because the buzz will die down. I think that’s been one of the coolest lessons for us.

It’s been one of the coolest lessons because we have something that people…People send us their content all the time. That’s awesome, another really cool feature of this thing that we have. That’s not the same for everybody’s product. You have to look at what you have and understand where it’s going to go up and down, and try to learn it, and learn from it, and then grow, and keep moving.

Every idea, finish it. Don’t just leave it hanging three quarters of the way.

Garrett: There’s peaks and valleys. The perpetual growth thing is not always there. To wrap this up, there’s one of my favorite questions. Obviously, we can’t go back in time.

If you could go back in time to any point directly related to Picture This or not and give yourself one piece of advice and know that you would actually listen…You don’t have to worry about a younger you ignoring you and blowing you off, saying, “Whatever. You don’t know what you’re taking about.” You know you would actually listen. What would you go back and tell yourself?

Jaimee: I would tell myself to put the idea out there. I think I’d say that specifically to myself because I used to not blog, not speak, not be out there socially because I was too afraid that I didn’t have anything of value to say, that I didn’t have anything neat, or important, or worth sharing.

I finally got over that little bump around 2010. I started doing public speaking stuff. Once I started, and it’s scary. It’s still scary. I’ve been doing it for eight years now and it’s still scary every time. I do it because it challenges me to grow in a way that’s scary that I think helps.

Every idea, finish it. Don’t just leave it hanging three quarters of the way. I guess that’s a big answer but put myself out there and finish. Don’t just start but finish the idea, whatever it is. Finish it. Bring it to closure and get it out there. Don’t be afraid to share it.

Maybe it is dumb. Who cares? At least you finished it and you put it out there. If you finish it, you’re going to be ahead of 80 percent of the other people out there who just have the idea and get it three quarters of the way and then move on to something else.

Garrett: The experience of launching and promoting something, to me and probably most creators is the most uncomfortable phase where you get the wind knocked out of you. All of a sudden you doubt. You can be confident for a year while you create something and then it comes time to share it. You’re like, “Oh, man. This is crap. I can’t share this.”

You lose that confidence but, on the other hand, releasing it into the real world with real feedback, who aren’t your parents or friends and family and say, “Oh, this is great.” You’re going to hear real things. That’s where you learn the lessons that you can then apply to whatever that next thing is. It’s that kind of crucible, which often isn’t fun.

That’s what helps you get to whatever that next thing is, if there is a next thing. It helps you realize, “Oh, here’s where I messed up here.” To me, I still hate that feeling every time I launch.

I just relaunched my book and I hated it. I was the most nervous I’ve ever been about a launch. It doesn’t change but you learn. You’re like, “I did that wrong. I’m going to do it better next time. Let’s do it.”

Jaimee: Yeah, you learn and you get better and stronger. You can look back at all the things that you did because you have a tangible point at which it was put out there. I don’t know. To me, it’s like little footprints or whatever.

I love that. I love looking back and going, “I did a thing. I did a thing. I did a thing and here I am. It’s leading somewhere. I don’t know where. I don’t know that this is my end point. I think that there’s still so much more in my future. This is just a really cool thing that happened. We’re going to run with it as long as we can.”

Yes, put stuff out there. Don’t be afraid. Learn from it. Grow. Keep going. Man, that confidence thing is really…I get my confidence shaken every three months. I’m like, “Ugh!”

Garrett: It’s constant, no matter how successful you are.

Oh, man. Parting words of advice. It’s finish the idea. If I had to give anybody, just do the thing. Whatever it is that’s stopping you, look at it and start chipping away at it.

Jaimee: Yep, it really is. I don’t know. I embrace that and I love it. It’s humbling. I don’t know what else I’d be doing, I guess, if not this. I just keep finding things that I love doing.

Garrett: Right on. We’ve covered a lot of ground. This is great. I’m really excited about this. I feel like it’s a different angle on a lot of things that we don’t usually get to cover. Thanks so much for being on here. Do you have any parting words, any last words of advice to somebody else who’s on the fence, thinking about changing?

Jaimee: Oh, man. Parting words of advice. It’s finish the idea. If I had to give anybody, just do the thing. Whatever it is that’s stopping you, look at it and start chipping away at it. Then keep moving forward because you will get over that obstacle eventually. You have to identify it and then chip away at it and keep moving.

That’s the stuff that changed my life. I had to break it down super small. One sip of water at a time. It was so small. Break it down, tackle it, keep moving.

Garrett: Right on. Thanks again so much. This was great. I really appreciate it.

Jaimee: Thank you. It was a lot of fun, Garrett. Thank you.

Garrett: Sure thing.

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