Founders Talk – Episode #72

Slow and steady wins

with Jeff Sheldon, Founder of Ugmonk


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Jeff Sheldon is the founder and creator of Ugmonk. Jeff is a designer by trade, and an entrepreneur by accident. I been following Jeff’s journey for the better part of Ugmonk’s existence. I’m also a customer. Jeff and I hold several similar values near and dear to our hearts. In addition to my appreciation for Jeff’s product design abilities, and how he leads his business, I also appreciate Jeff’s awareness and focus on the long hard path.



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Jeff Sheldon is the founder and creator of Ugmonk. Jeff is a designer by trade and an entrepreneur by accident. I’ve been following Jeff’s journey for the better part of Ugmonk’s existence, and I’m also a customer. Jeff and I hold several similar values near and dear to our hearts, and in addition to my appreciation for Jeff’s product design abilities, I also look forward to his monthly email of the finer things he’s digging… So that’s where we’re getting started.

Jeff, one of the things I love about you is this aspect of sharing. You’ve got this simple email - that thing has become like a cornerstone of your personal brand, “Five things I’m digging.” I bought stuff from what you’ve done, and I’ve checked out different houses around the world, because you have this aesthetic, this style you’re into… How did that email originate for you? What made you start shipping that thing?

Yeah, it’s a funny story… Most of the things like that that happen are not on purpose, and it was not some master plan to start sending out this email every month… It literally was I didn’t have anything else to talk about; it was an in-between time. I think some of our product got delayed, manufacturing got delayed, and I was like “You know what - I haven’t sent out anything, but I’ve got a lot of interesting things that I’ve seen and come across online…” and I was like “Here’s five things I’m digging.”

[04:04] It was nothing to do with Ugmonk, nothing to do with me; it was just fun to spotlight some other things, whether it was architecture, or an album I’m listening to… And then from that, I got all these replies, like “Dude, thanks for sending this. This is cool. I didn’t know about this band. I’ve never seen this new typeface…” And it was like “Okay, maybe I should do this again.”

That was 2-3 years ago maybe at this point. I don’t know how many I’ve sent, but now it’s like the monthly most-clicked email that I send out.

I just did a search for “five things I’m digging” in my email, because I can search by subject, and - I mean, it goes back a while. I think I have like a hundred in my initial view, first search… No, 50. And there’s several pages of this. Like, lots. You’ve sent a lot.

Yeah… It’s different, because for me it’s truly things that I’m into, things that I enjoy, and part of the Ugmonk brand and what I’m doing is looking at the world through my lens… And it attracts other people that like similar things, or are exposed to certain things that have a similar mindset, a similar design sense… And that’s really what I think has kept Ugmonk Ugmonk - it’s because it’s me, and all of the products are going through that same lens, all the emails are written by me… And people are attracted to it; they either get it or they don’t get it. And I’m totally fine if somebody’s like “I don’t understand what you do and why designers geek out on this.” I’m never gonna sell them on it. But then the people that love it are like “Dude, this is the only email I open every month. The only one I look forward to opening.”

I like that it happened by accident, like a downtime, which – I don’t know, I guess you seem to leverage the spaces, I suppose; the margin of life. And not too often do people really appreciate margin; as a designer, you totally appreciate space. Even the initial start of your business, which from my understanding - please give me the full story, but - is like you wanted to see your designs on shirts, and things like that…But you understand how to use space, and all too often we don’t know how to capitalize, or even create necessary margin in our lives.

Yeah. I mean, Ugmonk from day one was this side project that was to keep me busy, because I wanted to make sure it’s what I thought looked cool, everything has been a layer on top of that, year after year after year, still with that same mentality. I think when we create things that we’re passionate about, and you’re doing something that you love, there’s a different authenticity. And I know that word is overused, but there’s a different authenticity and passion behind that thing than if you’re starting in business and truly putting a business hat on, “How do we get X number of users? How do we get this monthly revenue?”, because you’re driven by totally different forces. And while money is definitely important and revenue sustains our business, and we need those things, for me it has to start with “Am I even passionate about this? Do I care enough to invest time in this idea, this concept, this product?” And then I think what happens on the other side is people see some of that passion come out through my emails, and photos, and Instagrams, and videos; hopefully, they’re getting a sense of like “Man, Jeff is really into this thing. It must be worth looking at.”

There’s a reason for it, yeah. There’s a reason he likes it. And then you have a pretty particular style, that I think others appreciate as well. That’s why you became successful. It might be helpful though – I know you pretty well, or at least I think I do. I’m not a Jeff stalker by any means, but I’ve known you for a while, and I’ve been a fan of yours… I’m kind of bummed that I don’t have your shirt on today; I’ve got at least a couple… So I felt like an idiot not wearing one of your shirts, but that’s how it is… But give us a framework, give the listeners a framework of - not so much when you began, but kind of give me some timelines, the fact that you’re a dad… Give me and them some sort of framework to understand Jeff.

Yeah, so I’ll start way, way back - when I was a kid, I’ve always been into art, making things, creating things, designing things… I didn’t really know that that was uncommon; I thought everybody just wanted to do that. I’d have friends over and be like “Do you wanna draw? Do you wanna color?” and they were like “No, I wanna do something else.”

[laughs] Play G.I. Joe and get dirty.

[08:08] Yeah. And I did that stuff, too. But I would sit there with my Lego set, or like Knex or any type of thing, and spend hours and hours obsessing over creating things from that. Not just following the instructions, but trying to make things. And I think that is in my DNA, because I’ve always looked at the world through that lens, and I always love looking at something, building things, making something out of nothing… And that’s what’s carried through, all the way to Ugmonk, even to this day. We’re talking about products that I’m making today are still – it’s things that I see in the world, and things I wanna solve for myself, and I’m able to assemble and bring in all these parts to make something out of that. So I eventually studied design, and then launched Ugmonk in 2008, which is crazy, because that was a long time ago…

11 years ago.

The internet was a different place back then.

Yeah, it was. Way different.

E-commerce was just getting started, there was no social media… I think maybe YouTube was around, but I don’t think Twitter was launched… Facebook was in its infancy… It was just completely different. You could name the five independent T-shirt brands on one hand. That existed at that time. And I happened to start around that, where the playing field was so empty; there was nobody really doing it, and I was able to carve out this niche for Ugmonk, and for the style, the minimalistic style that I’m doing now.

I think timing plays a lot of the key part of why I’m still doing it… Because starting a brand today, starting a T-shirt brand, a lifestyle brand, a design brand - it’s hard, man. There’s thousands and thousands of people just showing up on Instagram, launching companies and then closing down a couple months later because it’s just so crowded.

What’s the hardest part? And how long is that list?

So many, yeah… We could be here for another two hours. For me, the hardest part – well, two things. Before I had kids, I would say the hardest part was just focus and deciding what I should be working on, and what I should be delegating, what I should say no to, because I have a tendency to just dive in head-first to anything, and then realize a couple months in “Maybe this project wasn’t the best use of my time” or I’m getting distracted with all different ideas… I have no shortage of ideas, I guess is the thing.

Some people say it’s hard to come up with ideas… I’m more of the opposite. I’ve got so many ideas, I’ve gotta figure out “How am I gonna figure out which ones to work on?” But then after having kids, the hardest part is certainly juggling being a business owner and being a dad, and being a business owner and being a dad, juggling all of that stuff… Because it’s completely different parts of your brain, and there’s obviously time constraints when you have kids, and all the things that come along with that, that have changed the dynamic of Jeff just running his business however he wants. I have to be more intentional with my time. It’s also been (I think) a healthy change being able to have those guidelines in place, so I’m not just working sun up to sun down every day.

And I imagine you work from home, right?

Your studio’s at home…

For now, yeah.

For now, right.

Yeah, the kids are in the background, and there’s pros and cons to it. I mean, everyone’s working from home right now, but I’ve been doing this for my entire career pretty much…

Yeah. I’m with you on that front.

Same. In a lot of ways, we could probably commiserate on stories, because – let me try this one out then… I call them micro-moments. Some people might think “Gosh, you work from home. That must suck, to go get coffee and get bombarded by your kids.” Nope. Love it. Those are my micro-moments. I get to spend infinitely more time with my kids throughout the day, because I take a break. We do dance parties; I’ll invite my sons into the room, and we’ll turn off the lights, we’ve got a little disco ball, chilling over there, kind of thing… Boom, it turns into a dance party. I love those micro-moments. What do you think about that?

Yeah, definitely. I mean, I love the moments that I get to have, and the fact that we eat three meals a day together practically every day, because we’re home, and we’re cooking… That’s why quarantine didn’t feel that much different for me. We’re just always home, never going out and meeting people for lunch… But I love those moments, and I think there are a lot of things that I get to see that I’m not even realizing how grateful I should be, because it’s always been this way.

[12:11] If I was traveling and never home, I would have missed so many of these little moments with my kids, with them crashing into my office and taking all the stuff out of my cabinets, and dumping it on the floor, and pretending to work… They both say they have to come in and do emails, and they get up on my computer and they’re trying to pretend to work. They’re two and four, by the way…

So yeah, I love that aspect of it, and then I think there’s other times where I can switch out of the business owner hat, the designer hat, and I get to the point where I’m so side-tracked with them that there’s this tension of like “Oh, I’d love to just keep playing with them, but I’ve got limited hours in the day, and they’re gonna need dinner on the table”, and they’re gonna need the whole bedtime routine, and all that stuff is coming… So there’s this tension back and forth, of like letting myself just relax, enjoy those moments a little bit longer than just a couple minutes, or just say “Sorry, kids. I’ve gotta go back so that I can spend the rest of the night with you after I’m done with work.” There’s no delineation. So it goes back and forth.

How do you structure your day then? Do you do 9 to 5, or has it got to be more sporadic because you’re just naturally more sporadic in needs?

It’s fairly standard, probably anywhere between – well, they get up super-early, so it could be 7 to 5, it could be 9 to 5, it could be 6 to 4… It kind of just varies, because they’re always up at like 5 or 6 AM…

Which is the unfortunate thing…

Which is not necessarily my favorite thing, because I’m not a morning person.

Well, nobody likes to get up at 5 or 6 unless they are getting up to work out, or take a run… And even then, it’s still a slog. It’s tough.

Well, I think that you’ve got this aspect - what you’re keying on though is while you and I may be on the fortunate side and we get to 1) work from home, and I think with quarantine you have a lot of people doing that, some enjoying it and some not… But we’ve had this luxury and blessing to be able to do that with our families… And same - breakfast, lunch, dinner with my family, every day. Now, sometimes I’m more busy through the afternoon and I might swing by for lunch or grab something quickly, or I eat in my office or something like that, but most times I’m trying to balance things.

What I’m getting at is this – you hear this, even the word “authenticity”, you hear “balance”. “You need to balance.” I’ve heard this idea of work/life harmony, versus work/life blending, or work/life balance. How do you try to frame your balance?

Yeah, I think it’s an impossible balance. There is no right balance that we’re all seeking or striving for, because you’re never gonna get to a place where things are perfectly harmonious and you’re like “I’m working the exact right number of hours a day, and I feel like I’m with my family the exact number of hours I should be… Because the reality is work ebbs and flows, and there’s times where I have to work straight through lunch, or I have to put the kids in the bed and I have to work that night to get something done… But then there’s other times where it’s like “You know what - it’s Wednesday, and there’s nothing going on…” This was pre-Covid, and we’d be able to say “Let’s go to the zoo”, and we would just take a day off.


No one’s at the zoo in the middle of the week, because we would just go take the kids there. So I think it’s more of a give and take and ebb and flow for what it looks like work and life… I’m very grateful and very thankful that my work is something I’m passionate about and I enjoy, so it doesn’t necessarily feel like work = hate, life = enjoyment. So it’s not just working for the weekend, it’s certainly like “I enjoy this, I enjoy being with my kids, there’s times where I don’t wanna be with my kids, and there’s times I don’t wanna be working.”

But yeah, I think that question comes up a lot. We’re all seeking this utopian state where we just figure out how to work-life balance everything.

It’s always changing, right? It’s never static, it’s always changing to some degree. There’s some similarity in the change, but even the change is different and unique… So you can’t say (like you said) “It’s this way every single day, and my life is like this, and it’s boring, and it’s the same…” No, it’s dynamic, and always in some sort of rhythm of change.

[16:12] Something that you and I align on when it comes to, I would say, life and something that we’ve adopted in our business is “Slow and steady wins.” Now, we add on “Wins the race”, but life is a race of some sort, I don’t know… Maybe the race is not necessary, but slow and steady wins nonetheless. For me, that’s my North Star. If we’re moving too fast, slow down and check yourself. Now, I added that one on, so I hope you don’t mind… So in addition to “Slow and steady wins”, it’s like “If you’re moving too fast, slow down and check yourself.”

How has slow and steady been something for you?

Yeah, totally… That’s been a key differentiator, I think, of how I’ve built my business and how you build your business. I have never tried to build it to get this rocket ship growth where I can just turn it, get huge, get noticed, flip it, sell it to somebody else and cash out… Because for one, I can’t really do that the way I build my business, because it’s me; it’s so closely tied to my identity; I guess I could sell myself to someone. But the actual idea of just putting one foot in front of the other and showing up every day, and doing things consistently - that is the thing that I think sets me apart from a lot of other designers that have started their little lifestyle brand or T-shirt brand. At some point they gave up… And I’m just here, like – I’m not making huge, giant releases and crazy things all the time. I’m just putting one foot in front of the other. And for 12 years I’ve been doing that, to the point now when we launch something I have these passionate fans and friends and community around me that do help us have big product launches… But I call it the 12-year overnight success.

Yeah. I have to admit I haven’t bought Analog yet, or got on the Kickstarter, but I plan to.


I’m not an early adopter, but I’m an adopter for sure. And you’ve got like 30 days in a Kickstarter, so no matter what, you’re early. So I’m late early…

…but I do plan. Now, before we go into Analog, I do wanna mention Gather. So you’ve launched shirts, you’ve launched new things, you’ve got other people’s products in the Ugmonk store, you’ve got coffee - different interests; we’re both fans of Fellow, I love Fellow brand stuff. You’ve got a couple coffee things that are way out of my price range, so I’m not gonna buy those… But we at least appreciate the design and style of things.

Now, you’ve launched other things before. Gather, in particular, was one of your most recent larger, singular products, that was sort of tangentially, mostly in the design space, not so much laser-fit into Ugmonk… But you sell things that are useful, to people who care about aesthetics, simplicity, minimalism, essentialism, whatever it might be, however you frame it. How would you compare the launches, the state currently? I know we’re still in the launch, but the inertia of them. There’s some sort of velocity you can at least recognize.

Yeah, up until 2017 - that’s when I launched Gather, and that’s the modular desk organizer that’s all customizable… That Kickstarter blew up way beyond our biggest expectations. We tried to plan for worst-case scenario, best-case scenario, and it just blew the best-case scenario out of the water. Ended up raising $430,000 in 60 days on Kickstarter. And that was awesome, and then also really hard, because what that meant was we had this product that we had to ship to thousands of people, we had to manufacture… We were going through manufacturing overseas, and learning about all the things, and doing things at scale - handling customer service, handling lost shipments… All of that growth, which was amazing on the frontend, and people see the numbers on there and they’re like “Oh, cool. So you get to pocket half a million?”

Like, “Jeff, you’re rich. You’re loaded, Jeff.”

“What are you gonna do with all that money?”

“You’re going on vacation now.” [laughs]

[19:51] But it was a really big learning experience. The product has been really successful, people love it, we’re still selling them to this day… And it really just brought a lot of things back full-circle in that learning experience. Doing things at scale, and launching a product, and going big set us up to get on shows like Shark Tank, and things like that, where we’re just gonna be this big brand, we’re gonna try and get into West Elm, and Target, and all this… Because the Kickstarter did so well, it sent us down that thought experiment of “Oh, what if we could just cash out, and do this thing huge, and sell it off?” and none of that really happened. So it was really successful direct to consumer, direct to our customers it’s still very successful, but I realized in that moment “I don’t really wanna be the guy at a trade show selling one product for the rest of my life, trying to get into all of these big stores, and strike up retail deals.”

So after that whole process of going through that, realizing my eyes got big, wanting to go huge with that, and then coming back full-circle to like “I just wanna make more things. I wanna make more products, I have more ideas I wanna put out there… How do I get things done? How do I bring the manufacturing local? How do I have everything under one roof?” and that’s where we are today… I launched a second Kickstarter called Analog, and I’m approaching it completely differently. So it’s still going huge as far as the number of backers - over 3,000 backers at the time we’re recording right now - raised over $300,000, and we’re gonna have a lot of work to do to ship all these out… But I think the approach that we’re doing with this is very laser-focused on like “This is a product for a specific need, for a specific group of people, and we’re gonna sell it directly through our site”, and really that’s it.

We’re not gonna try and push this into other retail outlets, we’re really trying to make a product, make it here in the U.S, and make it really well, even if our margins aren’t as big, and ship it directly to the people by our own team. We’re gonna ship out thousands of these. We’re not gonna outsource that; we truly wanna bring this all under our roof. So we’re doing things the long, hard way, is what I say.

There’s a lesson there, the long, hard way. It’s interesting that kind of choice though, because Shark Tank has this inertia… Right? Millions of dollars, big success. Even whenever you watch it, they have internal commercials of other entrepreneurs and founders who’ve come on Shark Tank, and “They started out here, and this is where they’re at now”, and it’s painting this life - which I’m sure is great for some, if that’s your choice… But what I like about someone like you, and what I think is important to key on, is that that path isn’t the path for you, and you know that… But you took the time to think through it, and not just go down that path because everybody says “Well, Jeff, you’ve been successful. You should go this route. This is the default.”

That’s what I like about you - you’re alternative, but still not non-mainstream. You’re still influential, and thoughtful, and that kind of thing… And so too often do people just go down the path they think they should go down, because everyone else is going down that path, and it’s the default path… Or that the allure is truly the millions, or being on Barbara’s team, or Mark’s team… I would love to have Mark as a business partner, because he’s probably crazy, man; he’s probably amazing. But, gosh, what kind of weight would that put on me? Would that make me change my business to suit Mark’s psyche, or my psyche? …in terms of like “How do we think about business?” And I think that’s what I like most about your approach, because you’ve taken the time to analyze “What does Jeff really want from this business?”

Yeah. I mean, you probably wouldn’t be eating lunch with your kids every day had you taken on investment, right?

My gosh, no. I’d be eating lunch with them.

Yeah, exactly. And it’s not “Slow and steady wins” anymore, it’s “How do we get to the next ABC point as fast as we can?” or “How do we double that as quick as we can?” Because the reality is they wanna double their money, they wanna triple their money. That’s why investors are investing in things. So not having that external pressure to please anyone, and just going at our own pace, and doing things knowing that we’ll never have – I can’t burn $100,000 on Facebook ads and just be like “Oh, that didn’t work”, because I don’t have money to play with. I’ve gotta be really conscious of how I’m spending the money in the business, and how we’re taking steps to launch new products, versus just “Let’s see if we can do it” and “Oh well, it didn’t work. We lost the investors’ money.”

[24:24] It puts the pressure on your own back, to be more conscious of that… And just to know that there’s probably a ceiling. Like, I’m never gonna be a multi-billion-dollar company. Even multi-million. I don’t see myself growing to a huge company, because what I like to do is make things, tell stories, and sell things. That’s the thing that I really wanna hone in on; that’s what I wanna be doing for a long time.

Break: [24:52]

[28:19] Well, it’s one thing to say “Slow and steady wins”, it’s another thing to live it… But I’d say more so to keep living it. Because you can do it one time, and it’s like “Okay, great. This one time, slow and steady wins.” But how do you come back to that every single time? Do you feel the pressure to go faster, go a different direction? How do you keep remembering “Slow and steady wins”? Because that’s not easy.

Yeah, definitely not. And if I talk to any other e-commerce friends, or different circles of business owners, and Twitter, and all this stuff where you hear - everything is usually focused around growth, or celebrating acquisitions, or celebrating these big things, and you almost feel left out, like “Well, yeah, I’m never really gonna make a giant splash in the world, because I’m not gonna get written up on any site for how much money we’ve raised, how our fancy, new team and all the crazy stuff that comes along with how they spend the money, and advertising, and have a billboard in Times Square, or whatever it is - we’re not gonna ever be that”, and you just really at the end of the day have to be okay with it… Like, “This is not who we’re trying to be.”

I’m not trying to be another direct-to-consumer brand that has done amazing things; I think that’s a whole separate path, and it’s not wrong, but I just know it’s not me. I don’t wanna be the next Warby Parker, and Harry’s, and Allbirds, growing these huge companies, because that’s just not what I like to do. I don’t like to build and scale companies; I like to make things. So if I’m chasing people that are doing something like that, and doing it very successfully, at the end of that I wouldn’t actually be fulfilled or enjoy the process of getting there, because that’s not what my skillset is even designed for.

It’s about knowing what you want, and that’s too easy to say. It’s about knowing what you wanna optimize for. You have a particular style, a particular way you wanna live your life, particular things you value… And I think a lot of the journey for an entrepreneur is “What do I personally value?” Because once you understand that, and you have those things – if not written down, at least etched in your mind somewhere, on your hard, in your soul, it’s a little easier to take that first next step.

And like you had said before, it’s one foot after the other, not the other way around. It seems kind of logical, but maybe that’s because we’ve been doing this a while individually, and then – you know, this is your story more than mine, but I feel like that’s the same for me… But I’ve been living it, so it’s easy for me to say that, because it’s second nature… But for some out there, it’s like - they need representation. They need to know it’s possible. It’s okay to not wanna go down that route, because you value eating three meals a day with your family. Or when the pandemic is not in the state it is and it’s easy to go to the zoo - “Hey, Thursday was kind of a suck; I wanna take the afternoon off, or the morning off, or whatever. Let’s go do something fun. What do we wanna do? We have a zoo membership; let’s go to the zoo. Great! Or let’s just go on a walk, or a hike, or whatever.” Not everybody understands that that’s possible, I suppose, and I think it comes down to understanding your values.

Yeah, that stuff doesn’t show up on your balance sheet, and when you’re pitching someone to raise money. There’s all these intangible things about designing a business the way you wanna design it, and I don’t think it’s a one-size-fits-all. I think some people are good at managers, and good at scaling businesses, and good at sales full-time, and that’s what they should be doing, but I don’t think everybody should follow that path and feel like bigger is better… Or like “Why are we sprinting to the end, to cross the finish line” and then you get to the finish line and you’re like “Oh, I guess I’ll just do this again”? Why not just pause and enjoy the journey, enjoy the process, learn from those things… It’s the same thing that I’ve been doing - just learning. The entire 12 years I’ve been doing this has been one giant learning process, and I think that’s – you can’t put that on paper. You can’t go to college for that, you can’t do anything to get that, except for truly experience it.

[32:12] Yeah… Learn by doing, for real, basically.

Let’s talk about – maybe it’s too deep, or maybe it’s just deep enough, but… Actually trying to ship what you’ve gotta ship. So it’s one thing to make it, it’s one thing to design it, it’s one thing to even find the unique way to create a video that markets it the way that Kickstarter allows you to do, but it’s another thing to fulfill it all. You mentioned this idea of local, in-house… What makes you feel that way, versus outsourcing? I think it’s kind of obvious, to some degree, but why do you care about local? That kind of aspect. Bring it home.

Yeah, it’s a little bit counter-cultural in the way of Tim Ferriss’ 4-Hour Workweek - outsource everything, outsource your life… And I think there’s actually valuable things in that book, and valuable things that Tim would talk about… But this idea of “If I outsource everything, I can basically just sit in my chair on a beach and vedge, and all of those parts of the business work for me…” The reality is that doesn’t work. There has to be hands, and people, and processes in place, because things don’t go right all the time… And outsourcing things, in theory, should be the best way of doing it, because you outsource to someone who’s better at that specific skill, whether it’s shipping a physical product, coding a website, writing copy… But the reality is when you outsource, it doesn’t just magically happen and come back finished, perfect, done, every single time. And there is a cost of actually doing those things.

For us, outsourcing our shipping, outsourcing anything else that we try to do - the cost of losing customers’ trust, or losing that brand recognition and brand value that we built is everything… Because I’m in this for the long game, and I’m not in it just to sell a product and then turn around and start up something else. The Ugmonk brand is what I’ve invested in, and when it comes to shipping a physical product, I think those relationships - whether it’s customer service for something that went wrong with the product, or a shipment, all the way down to just physically inspecting the products, going through our hands, not trusting some fulfillment service or Amazon to say “Yeah, your product looks good…”

So it’s closing all of those gaps and really making an airtight business to bring it all in-house, have everything here - it’s expensive; again, it’s the long, hard way of doing it… But I do think at the end of the day the customers get the best experience, and it builds that lifetime value for us.

You had said something there too about - and this is where we align, too - this idea of… Did you say customers’ trust? Is that what you said?

I’m trying to phrase it properly… And for us, the similarity to that is listeners’ trust. We obviously are a podcast – podcasts; we have six active podcasts on… We’ve been doing it for a long time, shipped lots of shows… We have great brand name sponsors, that we love, that help us build our business, and they’re great, amazing partners… But sometimes we get the odd question where – not that they intentionally want to, but somehow, someway we objectify or get asked to objectify our audience, which basically erodes listener trust.

So similar to you, if that’s our line, we never break that line. If we break that listeners’ trust, it’s for nothing. If you’re listening to this show and you don’t trust that this show is authentic, that I’m literally talking to Jeff, and Jeff is a cool dude, and I’ve known him for years and love his story, and finally he’s on this show - if that is broken, what’s the point? If I make choices in my business that make me objectify that or break that rule, it goes against everything.

So customers’ trust for you - when I read what you’re digging, or I know you’re launching Analog and for some reason it’s applicable to you (or maybe it’s applicable to me), but because I trust you, I can think your next thing you launch is probably because you’ve put a lot of thought into it. That’s the brand I think of when I think of Jeff, and Ugmonk, and what you’re doing - you’re very thoughtful, you’re meticulous, you’re minimal, you have certain aesthetic qualities you like, and I’m gonna trust that when you do something, because of the choices you’ve made, that’s still true.

[36:21] Yeah, that’s the thing that you can’t buy or just pull out of thin air. You can’t spin up a new brand tomorrow and have instant trust with people. That’s why people have celebrity endorsements and all these things. They’re trying to show “No, we’re legit, we’re legit!” But the better way of doing it is just to show up, be authentic, show that you care, deliver on what you say… A lot of people are really jaded about Kickstarter because they’ve never shipped the products that they backed, and “I don’t know if I wanna back anything again, because these creators screwed us over…”

Now it’s like, for 12 years we’ve delivered products. We’ve built this trust that people don’t have to wonder if we’re gonna ship their product, if it’s gonna arrive, what condition it’s gonna be in, if we’re gonna take care of them if there’s a problem. Our repeat customer rate is through the roof. I don’t know what the industry standards are, and stuff like that, but I can tell you for sure that ours is way, way above that.

Now, our top-line revenue number might be way below some of our competitors or some of the people running similar brands, but our loyalty is so strong, and I feel like that’s more important to me. I’d rather have the 1,000 true fans, the Kevin Kelly article that’s been around for years and years… 1,000 true fans who will show up and buy and trust and support me for whatever I do, because they actually care, not because I have half a million people following me on social media.

You act differently when it’s the long road… Like you said, the long, hard road. When it’s the long-term, the long play, the long tail. All too often in business do we hear advice, seek advice even potentially, from those who are short-term players. And it’s not that they’re wrong, it’s just they have different goals. They fit them, for whatever reason; they’re optimizing for short-term versus long-term, and you just make different choices.

I can’t help but notice you’ve got this aspect of longevity and very high personal touch in all the aspects of business, and then obviously you have scale problems, as businesses eventually scale, whether you want them to or not… You can control it as best you can, but still, businesses are little animals and they grow; it’s just how it works, and sometimes you just have to make hard choices.

How do you follow that line of CEO/business decision-maker/designer? How do you structure your week, your day? How do you even mentally create the frameworks to “Today I’m CEO Jeff, tomorrow I’m designer Jeff. Today I’m packing boxes Jeff’, I don’t know… How do you juggle all these different facets?

Yeah, some of that I’ve figured out over the years; that is truly worth delegating and bringing on other people. I’m obviously not the one shipping out every single product we sell, or I would never have time to make things… And what I’ve really tried to do is bring in people that complement the things that I either shouldn’t be doing, or the things that I’m not good at. So I have my sister-in-law who runs all of our operations, customer service, and is really taking that over in these last two years… And she’s been able to off-load a lot of this stuff from my plate that I was just doing, like admin work, and invoicing… I just did it, because that’s what I just always did, but what that meant is as this stuff grew, there was less and less time to create new products and less and less time to do anything, to record podcasts. I just didn’t have time to do those things.

So finding specific people that you can trust to take those things off my plate - that’s what’s been the key for figuring out “How do I create this space and time?” And just being self-aware of what I wanna be doing… Like, “Do I wanna be designing all day? Do I wanna be scaling a business all day? Do I wanna be speaking at conferences?” Going through that thought experiment to figure out too exactly what I wanna do, and then how do I get there, how do I get rid of – okay, I don’t need to be the person ordering inventory right now. I should have someone else do that. Or “How do I figure out someone else to source packaging for us? I don’t need to be the person sourcing it, I just wanna design it.” And going through these little things of like figuring out the exact lane I wanna be in day to day.

[40:19] Yeah. How do you do that though and not lose touch? Because that’s what I find hard. Delegation - I’m not saying that’s not a good answer, but at some point you’re like “Now I’ve lost touch, because I’ve delegated.” How do you keep a heartbeat with the process, in touch with the tangibles that you’ve let go? How do you maintain the things that are extensions of you, since a lot of Ugmonk is very much like an extension of your personal likes and dislikes? How do you keep in touch?

Yeah, I mean - we’re still at such a small scale that I don’t have like… You know, an all-staff meeting is three of us; it’s not like 50 of us.

Right… Okay. And it’s usually at breakfast.

I don’t have to be like the Undercover Boss TV show where I sneak back into my company and nobody even knows that I’m their boss.

That’s a cool show, by the way. I still love that show.

Yeah… I mean, I’m still very high touch on a lot of things, and the processes or the ways that we do things is not like “I don’t know what’s going on over there.” I think I’m very much involved, but maybe the action that it takes to ship a product, or the action it takes to reply to customer emails - I’m still aware of those things, but I’m not the one doing the physical work when it comes to that. So I don’t know, I don’t think we have it dialed in perfectly, and there’s still things I’m doing that I really shouldn’t be doing, and things that I wanna be doing more of… So I think it’s a learning process too, but it’s an interesting way, because we have a family dynamic; it’s a family-run business. We’re all here locally, so we can actually be in-person, we can see our products, rather than this 50-person team scattered across the globe and nobody really knows what’s going on, except for what’s in Slack.

Yeah. Does that make the family dynamic difficult, by any means? Is Thanksgiving easier or harder because of - I don’t know, somebody’s slacking, or… Just hypotheticals, of course, but at some point there’s relationship tension, family or not. Is there some sort of unspoken, or maybe spoken bonds, like “Hey listen, we’re family, we’re doing this, but the thing that matters most is family, so first and foremost if you’ve got an issue, we’re family”? Do you foresee any future issues? Are you curbing against those? What are your thoughts on that dynamic in business?

When people find out that I work with my family, there’s two reactions. Either “Dude, that’s awesome! You employ your mom and she does all your shipping?” Or “How the heck do you work with your family? I would kill my brother/ I would kill my sister.” So I always preface it by saying “For our family, the chemistry or whatever it is seems to work well.” Not that we don’t have our differences, not that there’s tension involved, but it just seems to work well, and there’s a lot of trust, and a lot of closeness in our family… But I don’t recommend it to everyone. If you knew you would bite off your brother’s head as soon as you started working with him, probably not a good idea to go into business with him.

So there’s not really a definite line between “Okay, this is family time. We’re not talking about business.” I think it blends, because it’s all…

Already blended.

…one thing, and we’re getting together… And I don’t think that’s really been a problem. I mean, there’s times where work probably takes too much precedent, and inventory has physically overrun my parents’ house, because that’s where all the things are still stored, up until – a couple of months from now we’ll be moving it all out, but… Yeah, I have a very supportive family behind me, and that’s something also that I can’t just take for granted, because not everybody has that support system.

[43:42] Yeah, that’s true. For my wife and I there’s times where I tell her about my day, and she’s involved in things, too; maybe not in all the details, but she’s emotionally and mentally involved, and helps me behind the scenes discuss things and weigh options, and opportunities, and reminds me slow and steady wins, and “Slow down and check yourself if you’re going too fast…” She helps me be my rudder to like “Don’t go too far into the deep end.” There’s times when we’re having our time, and it ends up becoming – or I end up bringing up stuff from work, and next thing you know it’s 20 minutes later and I’ve just talked about a bunch of work stuff.

But she loves me and she’s supportive of me; it’s a unique process that you have to be aware that “Don’t go too far. There’s still a relationship there, there’s still a marriage there”, in my case. In your case it’s your sister-in-law. I don’t know what your wife has done for the business or where she operates at, but it’s gotta be a challenge and you don’t want work to overrule and the relationship to suffer as a result… And that’s what I was hoping to get some wisdom from you - this idea that in the end it’s family; it’s not business first, it’s family first.

Yeah, keeping those things in check is hard. It’s not always the natural thing, where I’m ready to jump in and play with the kids if I’ve just had something crazy happen during the day with work. I wanna tell my wife, I wanna go into all this detail about these things, and she’s like – you know, they’re ready to eat dinner; they wanna come play with you…

They wanna do Legos.

…and climb all over you and turn you into a playground, and all that stuff… But trying to just get those reality checks. It’s more of a self-awareness thing than it is anything, just to be like “Okay, I’m doing it again. I need to stop. I’ve gotta put work aside, and we’ll come back to it later, or when the kids are in bed we’ll talk about this.”

It’s hard, because – you know, if I hated my job, maybe it’d be different, because I’d be like “Fine, I get to leave the office early and I don’t have to deal with that person.” But when you enjoy it, it can have the opposite effect, where it can still overrun your life, but in like a bad way, where the tension becomes “Can you just let work go for a minute? Can you stop talking about work?”

Right. What are your thoughts on how you work is perceived by your children? And I’ll frame it like this - my wife and I were talking about this recently, and she’s like “Babe, it’s kind of weird, because your son…” Sure, it’s pandemic, let’s preface it with the fact that we’re all in quarantine anyways, but as we said before, prior to that - we both already work from home anyway, so this is life; how we do things is life. It’s not different because of Covid or the quarantine. She’s like “You walk across the house and you go to work, and then you come out… Other kids don’t have that perception. So how do you take what you’ve done as a father, but impress them how work is different, or how work can be different?” And I think it’s also important to see your passion for what you do.

My son had to do this thing for school – he’s in pre-school, he’s four years old… And he had to explain what his dad did, and it was comical. I loved it… Because apparently, I listen to music all day.

You’ve got headphones on and you’re just jamming out…

I’ve got headphones, we talk into mics, we have music on our podcast, I edit, there’s music involved… You know, there’s definitely music involved, but his perception of what I do is uniquely different than most other kids… And how does that shape him? What I mean by that is how do you let what you do for work, impress your kids in who dad is, and your passions in life, and the things you value? …from that perspective, from a work perspective.

Yeah, that’s a good question… My kids are two and a half and four, and they’re just now to the point of questioning things, deeper questions… What did my son say the other day…? “Where do strawberries come from?” He was just genuinely curious, like “Do they come from animals? Do they come from a tree?” Just like things where you don’t think about… And they’re starting to pick up on different things about work… I have all these damaged pieces from the [unintelligible 00:47:48.12] around, and they play with them, and they’re putting stuff in, and they pretend like “Hey, I’m sending [unintelligible 00:47:53.13] to someone.”

They’re kind of starting to get the concept, like “Hey, we make and sell physical products”, and then they’re trying to reenact it… But I don’t think they understand that most of the time, most kids don’t get to see their dad all the time, or walk in on him in the middle of a call, and all that… Now it’s becoming more normal, because everyone’s at home… But there’s things where, as they’re growing up, I wanna make sure that I’m being intentional with showing them what I do, how I do it, how it’s different, and also for them to be grateful for the time and the perks that they receive, even though they didn’t have a choice… But for them to see, like “Hey, not everybody gets to see their parents this much. There’s a lot of things where it feels normal to you guys…”

[48:34] And I’d love to get them involved in the business in some way. Not like they have to inherit Ugmonk and have to carry on the family name, but just to show them what it looks like to pack 100 orders, and get all sweaty carrying boxes up the stairs. That’s part of it too, and I think that’s gonna be fun, just to bring them into the whole idea of what we do.

Yeah. That’s such a cool thing, I think… And I feel so fortunate, because we do podcasts with my son that we have, The Eli Show. My son’s name is Eli… We haven’t done one in a bit, but we do a podcast together every once in a while. It’s usually about trainings, or certain colors, or questions like “Where do strawberries come from, for example?” We’ll just talk on this thing, and like – I want him to see that it’s uniquely different than what other dads he sees out there in the world might do… But it’s not that it’s different or better, it’s just unique. It’s different. I want him to even feel welcome. I don’t know how you are with your office or your workspace at all at home, but I don’t want my kids to feel like “You can’t come in here.” I want them to come in here. “Be careful of what you touch, but you can come in here. You’re not not welcome. I want you to be able to come in. Obviously, there’s times and places where it’s more or less better, but for the most part I want you to feel like this isn’t dad’s world; you’re welcome in here.”

Yeah, I have this one cabinet back here that’s their cabinet, and it’s just got all the extra hardware, and pieces of stuff in it, and they come in and take it all out and make a big mess… But they know that’s their one cabinet that they get to play with, and pretend to do work, and deliver me my coffee, and all these things.

So yeah, trying to keep them incorporated… And big-picture, what I desire is that they’d be able to see how many options there are to do what you wanna do in life. You don’t have to follow a certain path, and I think so many people are just assuming, like “You have to do this. You have to go to school, you have to go to college, you have to be this, you have to work your way up the ladder”, and a lot of people just don’t fit that mold, and there’s so many other things that you can do with your life. As we’re seeing college and things kind of fall apart, and the whole virtual thing right now, where people are like “Wait, why am I paying $100,000 a year for this virtual Zoom college?” There’s just a lot of different opportunities out there, and different ways, that are not better or worse; to go to a trade school, to become a podcast editor, to design, to do any of those things. There’s just a lot of opportunity, and I hope that they see Ugmonk being such a different thing that it gives them ideas to do what they wanna do.

Absolutely. Let’s laser in on Analog, because I’m really curious about the inception. It’s literally a physical list that you handwrite, it’s a unique system… From what I can understand, you’ve been doing it for years… What’s been the process of creation, and what does it mean to you?

Yeah, so Analog is what I’m calling “The simplest productivity system.” When I describe it, one of the key things is this paper to-do list - it’s 3x5 index cards that I’ve designed - does not replace your digital system. It’s not like “Oh, instead of writing emails, now I use a typewriter and a carrier pigeon. Ah, that’s better, because there’s no distraction.” No, this actually helps me work better digitally, because I’m able to pull my tasks out, put up the ten things on this card, write them down, and have it stare at me all day, every day, or right next to my monitor, and that’s what keeps me focused.

There’s something about that, and the tangible crossing things off, having it there, not having to swipe up and look at it, or switch tabs to look at it. That has worked really well for me, and that’s why I created a product out of it.

[52:14] What is this system? Is it simply a daily thing, or is it like a long-term, “Here’s a week goal”? Is there more to it than just simply every single day?

I use it daily. So there’s three cards; it divides everything into Today, Next or Someday. The Today card is what I start with every single day. If I don’t start with that card, I’m usually in my inbox, or scrolling YouTube or something, and before I know it, half the day is gone.

The Today card I fill out every single day, and then anything that doesn’t get crossed off automatically goes on the next day’s card as I start that day. And what happens is you start carrying over these tasks that you’re not doing or not getting to, and by the fifth or sixth time you’re like “Either I don’t need to do this, or I just need to get it done first, and finally pick up the phone, make that call, and do all the things.”

It’s beyond just being an index card, and being a well-designed index card with this wooden holder. It’s really a way of thinking, and it’s about prioritizing, it’s about constraints… It’s about really saying what is enough, like “How much did I do today?” If I have a digital list of 53 things and I only get to five, I feel guilty; there’s this productivity guilt. I didn’t get to enough things. The Analog card constrains things to up to ten things; sometimes I only put two or three things on there that I have to get done that day, cross them off, and I’m done. There’s a sense of completion.

What about the design process to this? How did you get to this framework where you just literally – you know, somebody else’s 3x5 cards, turning them vertically, writing things down… Or was it a blank sheet? How did you get to this system to think “I should design this and make this a thing” and get to where you’re at now. How did that play out?

Yeah, years and years of using regular index cards, and saying “This keeps working for me. Maybe I should design a custom one, print out some ones just on my own printer…” The card itself is really simple, but what I did was pull in other ideas and concepts that have already been established as ways to be productive, getting things done… You know, things that other people have shown me. Bullet journaling… A lot of these concepts – I’m not taking the credit that I created them, but I brought them all into a format that seemed to work for me, in this card format, rather than like a big journal or something else. So I brought all these concepts in, and then the card is just very simple, but it’s effective enough and it’s open enough that you can use it however you want. You might not use it the same way that I do, and I color in half the circle if something is progress, and fill it in if it’s all the way complete, put in an arrow if it’s delegated… But the card itself can be used in so many different ways, and it can be used for other things.

Just simply, yeah.

People are even telling me – some of the friends I had testing it was “I bring this to meetings with me. I bring one 3x5 card to a meeting, and that’s all the notes that I can take, and then I leave, and I don’t bring my laptop.” The difference is made in the clarity of discussing things without having browsers showing up, and you get distracted, “Let me show you this, let me show you this.” So just like – I don’t know, I think it’s really a shift of mindset more than it is just a physical invention, because people already write things down. I don’t have to convince anybody to say “You should write this down.” “I already use post-it notes, I already use a journal, I already use this…” or “I lose it. I can’t find this. I put it on the back of an envelope.”

So I’m really just pulling in all of these concepts, both physically and mentally, and making Analog what it is.

And if you’re listening and you’re thinking “I wanna see this thing”, I’m sure you can just google “Analog Kickstarter.” A-N-A-L-O-G, like Ana, Log. Kind of like ChangeLog. Just kidding… But there’ s a video at the top there, a well-done video. Jeff, there’s nothing that you do – gosh, sometimes I hate you, but sometimes I love you… You’re so good at presenting things so well, man. I’m very impressed with how you show off your shirts, how you show off your products, the way you approach creating videos like this… It’s just so good. So good.

[56:04] Thanks, man. Yeah, I actually shot the video and edited the video myself, because I was planning on going down to shoot with a whole film crew, and editing, and all that stuff - it was gonna be like a whole production. But then Covid happened, and I was like “Oh, what am I supposed to do now? Do I just wait till this is over?” and here we are, months and months later. So a friend challenged me, and he’s like “Come on, you can do video. You’ve done some other stuff before” and I’m like “Ah, I don’t know if i can make it good enough. I really want this video to be awesome.”

So I spent like a month just planning it, working on it, diving into Final Cut, trying to learn all of the things… I had my brother over for a couple times to hold the camera. People were asking me how I was holding the camera with me at the desk… The two of us just worked together, and then I just edited it, I hired an animator to do some of the animations, and spent way, way too many hours working on that final video.

Scrutinizing the details, man… Yeah.

Yeah, I love obsessing over that stuff. That’s maybe one of my strengths and my weaknesses. I could spend all day, just weeks and weeks working on a single thing.

Is there a future “Sweat the details” shirt coming soon?

Say it again?

That was tongue-in-cheek, meaning you sweat the details…

Oh, sweat the details… Yeah, I did have a shirt that says “All in the details.”

All in the details.

And that’s definitely it. If you’re not obsessing over or sweating the details - those are the two ways you can kind of frame that. That’s what we tend to tell ourselves. But then it’s also “Perfection is the enemy.” Sometimes when you’re sweating the details, you’re sweating perfection; and are you serving perfection, or are you serving done? And you can sort of ebb and flow and flying it from there… But you’ve got such a good delivery, and kudos to you for making it work, and still delivering the Ugmonk style that I’m used to seeing. It’s well done. It’s really well done.

Thanks, man.

I’m very impressed.

I think it goes back to, again, that process. I actually had a ton of fun in that process. I had the story in my head, worked through so many different revisions of scripting it out and storyboarding it out, trying to get a concrete – like, “How do I get this idea communicated? How do we shoot the BeeRoll, and how do we get this concept across to people in a three-minute video?” And even though that’s a challenge, and it can be hard, and I don’t feel like I’m a professional filmmaker, I do enjoy trying to figure that out, dissecting other people’s work, studying other film and understanding that stuff to a point where I’m like “I’m gonna try this.” And not to claim that I’m gonna win some film festival award ever, but to get something to the level where people would be like “Wait, you shot that yourself?” and I’m like “That’s the best compliment you could get.”

Ha-ha! Well, you did go to – what was it? Iceland? Or was it Greenland?

Yeah, that was a point-and-shoot camera in Iceland, and that video blew up. That was probably the most watched video I ever made.

That’s impressive though… We’ll link it in the show notes for the listeners. That video was amazing. To me, one aspect that I like about what we’ve been able to do here at Changelog is that it started out as just a podcast. Just. That keyword “just”. But then it got into all these other tentacles of things I love to do - photography, film… We haven’t done all these things all the time, but we have done some of them over the years… But it’s like this playground of “Okay, here’s the core interesting brand, but here’s all these other tangential interesting sub-things I like to be involved in”, and this gets to be a place that I can make my long-term play, and an interesting playground to do not just podcasts, or JUST podcasts, but to do so much more than just simply that. That’s what that is for you. It’s like, I’m impressed, but I’m not surprised, let’s say it like that. I’m totally impressed, but not surprised… Because I saw that video that you did, and sure, it was just point-and-click, but you’ve got a certain style, and if you can study somebody else enough, or people that impressed you, then… Mimicry is – I don’t wanna say it’s easy, but if you’re good at what you do already and you already have this designer aspect to you, with a little effort, the surprising thing is that most people can do a lot of things they don’t think they can do, like this, for you. I’m not surprised, but I definitely am impressed.

[01:00:20.27] For me it’s more about training my eye to see things in just that natural understanding of the way that I can see the world, or just understand why I like something… I think a lot of people will say “I like that”, but they don’t really know why they like a certain thing.

For me, it’s a tricky balance. I think we all face this, but it’s not about having the latest gear; I didn’t rent some $20,000 RED camera. I have this camera that’s a Micro Four Thirds that’s probably 5-6 years old, decent lends… It’s a decent enough setup, but really what it comes down to is nobody is going to like or dislike that video based on what camera I had; it was more about how I communicated, how it was shot, what was the story behind it. Did that story connecting with people, or did it not? And getting past some of that gear, and tech, and tutorial stuff - that’s where a lot of people seem to stop. It’s like, “I can use this camera really well”, but you can’t tell a story with it. It’s gotta be more than the gear.

And again, I’m not trying to put myself on a pedestal, like everything I do is perfect, but I do know there’s forums and forums of people debating audio and video gear, and what did you actually make with it? What did you create? What story are you trying to tell with it? And a lot of times what it comes back to is just talking about gear, just talking about code, and all of these techniques, and not actually building something. I like to see people that build things, regardless of if it’s an iPhone video, or if it’s a full-on produced video.

Yeah. Well, all too often do we get kind of gear-crazy, like “I’ve gotta know what Jeff’s setup is. What does he have on his desk? I can be Jeff if I’d just know what kind of machine he uses, or camera he’s used.” And then that’s a part of the story. The other part is the passion, and showing up, and fine-tuning the craft, and getting through the suck, and saying no to a thousand things, caring about those thousand true fans… Slow and steady, sweating the details. That’s the stuff that I think is the value, not just simply like “Oh, I use this camera, or this lens, and this light, and with this angle, with this aperture or whatever, and so you can go and do, too.” Sure, you can, but it’s not just simply the specs.

Yeah. Taking time to hone your craft is different than learning a new skill. Somebody could teach me how to play the trumpet in probably a couple of days. I’d be terrible at it though. It takes a lot of time to keep working and keep perfecting one thing, and in a world where there’s a million options to do everything, and we can pick up any type of skill… I can be a coder, I can be a photographer, I can be an actor… People don’t stick with something long enough to really perfect it, and then when you see people that have, and you see professional athletes, professional musicians - you’re like, “Man, they’re amazing”, but you don’t see the 22 years that they’ve been just sweating it out, literally sweating it out to get to that place to finally be recognized for it. Because people don’t wanna spend that much time doing anything.

Well, if it was easy, everyone would do it.


Ain’t that right?


Let’s put some urgency on the audience then… For those who are like “Man, I’m sold. Take my money, Jeff.” How can you take their money? I’m just kidding…

Lots of ways.

Well, how can they get involved with Analog? What’s the next step? I know it’s in Kickstarter right now. Listeners might be listening to this after the fact, I don’t know… Let’s say they’re listening to it pre-Kickstarter being over, and then post-Kickstarter being over. What is the process, tiers…? What do you say?

[01:03:55.19] Yeah, we’ll make it easy. That will forward you to the Kickstarter if you’re listening to it now. And then after Kickstarter, that will forward you to a page on our site where we’re gonna continue selling Analog. But the Kickstarter will be the best price, the best option to get in. We’re offering special deals and perks to the people that get in early, while the campaign is running… But we do plan on turning this into a long-term thing, where we’re gonna be selling these cards - the cardholders - on our site. I’m even thinking about doing a subscription, and things like that, where you get automatic refills on a monthly basis, those kind of things. You can check out the whole campaign if you just go to that URL.

Interesting. Refills, I like that. I didn’t think to ask you about that, how do people get refilled. Well, we’ll definitely put those links in the show notes, so that those listening can follow along. And you’ve reminded me of one question I didn’t actually get to ask you about Analog… And I can’t stop there, because I’ve gotta have this question answered. You mentioned before about what to focus on, the biggest challenges that you faced, one of the biggest ones was like “I’ve got lots of ideas, but which one should I do? Which one should I do next?” We kind of know the story of Analog, but more particularly, how did you know you should have done it, and how did you know other people would appreciate it? What were those things that you did? Did you have a committee/cohort of people who were like “I’m trying this, Jeff. I love it”? Did you refine it with other people, or was it simply in isolation?

It was a little bit of both. So because I’ve been using index cards for so long, I thought – originally, it was too simple of an idea to even launch, because people can pick up index cards and basically replicate what I’m doing with Analog right now. And if they wanna do that, that’s totally fine, but we’re using nicer paper, it comes with a stand, it has the bullets already ready for you… It’s this framework and structure to get you thinking about it. It serves one purpose, whereas an index card - we all have stacks of them, but they can serve any purpose.

So I knew that there was something there, because I kept going back to it, and it kept helping me. I’d try a new to-do app, and then a week later I’d wanna switch. I’d try a new task manager, then I’d switch… And the index card kept being a thing for me, so I started sending out samples to friends. Once I printed up a short run and been like “Hey, do you wanna try this thing out? This is what it’s doing for me. Tell me what you think”, and just had a small group of friends testing it. 9 out of 10 of them were like “Hey, when do I get more cards?” and I’m like “Okay, I’m on to something.” Like, “I’m using these cards this way, and this is how it’s helping me.”

And these aren’t just random people, they’re people in high-performing roles, that have a lot of responsibilities, and things like that… And that really validated it past just me saying “This helps me.” And beyond that, it was like “Well, let’s go for it. I think this is gonna help a lot of people.”

On that note, did you anticipate the idea of refills, or was that sort of discovered as a part of that process?

[01:06:46.12] I mean, because you’re writing on a physical card and it’s not erasable and reusable, we knew that there was an option to do something like a subscription. So part of the business that’s different is that it’s gonna be a very low price point compared to Gather and compared to a lot of other things we sell on our site, but the idea is to bring people back through our doors and say “Hey, are you ready for more Analog cards?” If you’ve found it useful, it’s basically gonna be a no-brainer to keep using it. We haven’t decided on the price, but for somewhere around $10/month, if this is actually helping you get work done, it should be a no-brainer.

Boast about some of the numbers too, real quick. I’ve been following you on Instagram, I check your Instagram stories… By no means am I even on Instagram every day; I check in maybe like three times a week. I don’t post anymore, I’m weird. I’ve sort of backed away from social media in that regard, but I still lurk, which means I still pay attention to certain people, and you’re one of them, at least as of recent, with Analog and your frequency going up, and stuff like that… But I’ve seen smaller numbers, and then this excitement of bigger numbers, and now a much bigger number, which is just huge… Those are your numbers, you share them.

Yeah, so we’re a 3,448 backers as the time of the recording, so hopefully that’s even higher by the time people are listening… And $305,284 raised for this campaign. We still have two weeks left, and honestly, it’s gone as good as it could possibly go, and I’m super-stoked on how people are responding to the campaign.

Are these numbers you expected? Are you blown away? Are you just happy? All the above.

I’m blown away. Again, I’m trying not to be over-confident, but we knew that there would be some level of success with Analog, because we had run Gather and had done one other Kickstarter… But this is way beyond – this is the top of the top scenarios that we played out and calculated and figured out. And you kind of have to be ready for it to not hit that, but then for it to blow past it… And just to see how many people are really wanting to buy in as a system; they really want Analog to be here for the long-term, and the questions we’re getting asked are “Well, I live in the U.K.” Well, you have refills available over there. “I wanna make sure I’m getting enough cards for a whole year.” All of these questions of like – people see the value in this before they’ve even had it, and 90% of the pledges involve more than just the cards; they’re buying the cardholder with it. So that was the big surprise - how many people see this as “I want this on my desk. I wanna buy the cards and I want refills long-term”, and that’s where I’m like “This is exactly what we would love to see.”

That’s so cool, man. Alright, Jeff, I have two final questions for you. The first question is my super-secret question… It goes like this - what’s on the horizon for you that no one knows about, or not many people know about, that you can share here today? And the second question is “My biggest lesson learned” question. When you give advice from your journey, Jeff, what’s the one thing you hold on to? That one lesson that’s near and dear to your heart? We’ll get those answers from you in just a second, Jeff… But hey, audience, if you want to hear Jeff’s answers, you have to be a Changelog++ subscriber. Join Changelog++ and make the ads disappear, plus get extended content like this, and so much more. Head to to become a subscriber.

Jeff, thanks so much for your time today, man. It’s been many years… I’m glad to finally get you on Founders Talk, I’m glad to dig through a lot of this stuff. I’m sure we could have covered so much more, so hopefully one day you’ll say yes to coming back again, and we’ll have more to discover and more to talk about. Maybe the next Analog, the next big thing… But seriously, thank you so much for your time today; it’s been great to have this conversation with you.

Yeah, for sure. Thanks for having me on.


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