Great products often have great people behind them. Few people know that better than Justin Jackson, whose Product People podcast has had guests like DHH, Jason Calacanis and Patrick McKenzie. Additionally, Justin is the Product Manager at Sprint.ly and the author of Amplification and the Hacker News Handbook. In this interview we discuss what it takes to build great products and podcasts.

Today I’m joined by Justin Jackson. Justin, welcome to the show!

Thanks! It’s good to be here Solomon.

That was a good intro. Intros always scared me a little bit, because there’s so much anticipation up to that point. You did really well.

Ha! I’ve done thirty or so interviews, so I think I’ve gained some experience.

You’re an expert now. It just takes thirty times and you, too, can be an expert!

Well, if you would, tell us about yourself. Who are you? What do you say when people ask you what you do?

Lately I’ve been thinking a lot about me as someone who likes to make stuff.

I recently got back from the XOXO Festival in Portland. It’s a conference for people who make stuff. And I’ve always been on the software-digital side of things, but there’s also all these people that were making physical objects.

I saw everything from ice cube makers to different types of software. The more I thought about it, the more I felt that I just really like making things.

I make blog posts on my blog. I make software with Sprint.ly. I make digital products like books and video courses and I make podcasts. So I think lately I’ve just been saying, “I like making stuff.”

People, not products

I’ve been following you on Twitter and your newsletter for a long time now. It seems pretty obvious from those that you like making things.

I’m curious where you think that drive to create comes from. Why do you like making things?

So this is an interesting question, because I have a friend who’s been a bit of a mentor to me for a long time. He thinks that at my core, I’m not a maker first. He thinks I’m a people person first. His theory is that my love of people and relationships, pushes me to make things.

I think there’s some truth to that. If you look at my blog archives and my newsletter, I’m talking about products, but really I’m talking about people. Human beings.

The title of my podcast isn’t Make Products, it’s Product People. I was always interested in the people’s side of it. I think that that’s a little bit different from some makers. Some makers really like creating the thing, and perfectly crafting this object or software. For me, I just like the people part of it—figuring out what people need, and then delivering something of value, getting the response, figuring out how it can help them even more. That part is very interesting to me.

So lately, I think what pushes me is just that I like human beings. I like this idea of connecting with people, whether it’s with a podcast, a blog or something that you’ve made.

“The title of my podcast isn’t Make Products, it’s Product People.”

That’s interesting, because honestly I’ve never thought of it from that standpoint. But the reason that I keep doing Signal Tower, even after two years, is because I like reaching out to interesting people.

After every interview, I’ve got a new friend—a new contact. Even further down the road, there are people whom I’ve gotten to know who could benefit from other people I’ve talked to.

Yeah, I’ve always been interested in who’s behind the screen. To be honest, I didn’t even realize that not everyone felt that way until I started talking to other people who make things.

A lot of my developer friends are only interested in the logical problem. That’s not interesting to me at all. If you gave me a math problem, my answer would probably be I don’t care. I honestly don’t care.

For me it’s more about thinking about something and going, “Wow, I’m really motivated by this piece here.” Not necessarily the logical process of solving a problem.

You’ve built a ton of things. You’ve also got the JFDI, which is now the Product People Club.

What are some of the other projects that you’re working on?

You’re going to see a theme here, because Product People Club started off as this group as Just Fucking Do It.

I’d met all these people that were building things. I’d also met this group of people who subscribed to my newsletter and getting frustrated that they were consuming all this content about building things but they never actually did anything. So I thought, what if we created this community where we encourage each other to build stuff? A place where we could see other people shipping and go, “Wow. John just shipped and Jen just shipped. I’ve got to create something!”

We started in a Campfire chat room with 13 members and I think it’s grown to about 80 or 90 members right now. We’ve sort of kept it at this level. We have a waiting list of people, but are trying to not go much higher than that.

I’ve mentioned this quite a bit, but I’ve worked full-time throughout all these projects that I’ve done. Eventually, I’ll be doing my own things. But one of the things that my wife and I decided to do is that, we have four kids, and we want them to get a bit older before we commit fully to a business.

Getting to do these little things on the side has been really fun, and Product People Club is one of those.

“There are sometimes when I’ll stay up all night because I am inspired.”

I guess that segues nicely into another one of the things I’m curious about. How do you find the time for all this stuff?

You must not watch much television. I just got home from work and now I’m doing an interview. But I’m curious, with four kids, where does the time come from?

Oh man.

So, I used to have this really smart response, which is still a smart response. But it doesn’t fully encapsulate the reality—yeah, I don’t watch television.

I try to have good habits. One habit that I had for a long time was waking up early on a Saturday morning, before everybody else and have a couple of hours to myself. So, I’d have from about 5 a.m. to 7 a.m. and some time late at night to put in time. The other part of it is just that I’m scrambling.

There are sometimes when I’ll stay up all night because I am inspired.

That’s what I always tell people is, if you’re inspired on a project, focus on that because you’ll be one thousand percent more productive.

So when was the last time you were inspired to work on something?

There have been a few blog posts that I’ve worked on that I got inspired late at night and then I just kept going.

Sometimes I’ll get inspired to just focus on a concept, like I’m building a web app with my friend Marty. Sometimes, I’ll get into this flow of having my text editor opening, my terminal window open and just updating things, deploying them, testing them.

I’ve had a few almost all-nighters working on this app. I’m not a developer by trade and getting in those modes of flow that I’m not used to is just really fun and addictive.

But you’re right about inspiration. My favorite quote about it is by Jason Fried and it’s, “Inspiration is perishable.”

Get Shit Done Sign
Motivation for the makers in Sprint.ly's office. Get shit done.

I think habits and processes are good. We do need to have those too—like shipping a newsletter every weekend. But on the other hand, there’s just those all-nighters where you’re on fire and you don’t even know what time it is and you’re just in the zone and you wake up the next day and you can’t even believe what you’ve accomplished. It’s gratifying.

I’ve done it another way too. That’s to take a day off, and while normally on a day off we’d do a bunch of errands or hang out on the beach or whatever, instead, take a day off and do “these” things that I want to focus on for this project.

Taking a day off from work to work on a side project can be really helpful. It puts some fire in your belly and gives you some anticipation about all you’re going to do and accomplish. Getting excited about setting aside this time and cranking through some work—those days can be really helpful, because it’s not a Saturday or something you’re used to relaxing on.

You seem like you might be a list maker? Do you use lists to get organize your ideas?

There are some things I’m working on, personally, and one of them is that I want to become more of a list maker.

I have been one in the past and, you know how you fall into habits and then out of them and build up new ones? I do make lists, and people make fun of me, but I use the Apple Notes app all the time—that’s where I dump brainstorms, ideas and lists.

For example, in January, I said, here’s a bunch of monthly goals I want to hit for my side projects every month. I made that list and I’ve referred back to it every once in a while to check if I’m on track or even just getting close.

I’m also trying to figure out how I could be better at it. Because I think I could be better at making and following lists.

I wish I had a better one, but here’s a list of the features I’m working designing and building for Signal Tower.

I’m a senior interactive producer so most of the agency’s digital projects come through me. I have a ton of little things I need to keep track of.

I organize my lists by clients. There may be three to five things that need to be done be done—each with a little check box next to it.

At the end or beginning of each day, if my diligence has been done, it gets a checkmark. If the item has shipped or my input’s no longer needed, then it gets crossed out. Whatever doesn’t get crossed out—even if it has a checkmark it goes over to the next day.

The joke around the office is that if it’s not on my list, it won’t get done.

So how do you manage those lists? I have a list at work obviously, and then I have a list for each project. So do you just have multiple pieces of paper or what?

I’ve got one note pad like this for work and one for personal projects. My work list has our client’s names. My personal list has Signal Tower or the name of whatever project I'm working on.

One stays in on my desk at work and one stays at my desk at home.

I feel like I’m just going to jump into a system like that before too long here.

Analog is the best system. We tried using Wunderlist and the creative team uses Things.

I don’t think there’s a digital equivalent as good as paper lists. A lot of people at work have started to move back to paper and adopt my to-do list strategy.

It’s a good way to get things organized and it makes things manageable. It also feels good to physically go through things and cross them off.

Yeah, I love that. I’m gonna try it.

Sprintly Quick Left Portland Office
A shot of Sprint.ly's Portland office. Earlier this year Sprint.ly merged with design and development studio Quick Left.

BUILDING A PODCAST

Well, let’s talk about podcasting. Because that’s what I’m most interested in, and what I feel like is most relevant here. I’m curious, why did you decide to start Product People?

Cool. I love this story because it shows, again, the influence of people.

I have this buddy from Edmonton, Alberta named Kyle Fox. He’s a great designer and developer. He’s worked for some cool companies.

Anyways, we’re Twitter buddies and one day he hit me up and said we should go out for beers. So we met up and just kept talking about products and the product people we really admired. We also talked about an onboarding sequence we really admired—we just had this great conversation.

After that, he contacted me and asked me if I’d ever thought about starting a podcast. I actually had, dozens of times, but I never acted on it.

Having him say that we should do one together was enough of a push for me. We started it together and after a while, he got too busy from work, but I enjoyed it so much I decided to keep going.

It’s funny, because when people think about the show, now they just think about me. The reality is, without Kyle it wouldn’t exist.

It felt like there was some momentum behind the idea. So yeah, I’ve kept doing it. I don’t do it as regularly as I’d like. I try to put out a show at least every two weeks.

I had a show last Thursday and I’m gonna have one tomorrow so, I’m back on track for every week right now.

That’s wonderful. But I know that feeling, there aren’t enough hours in the day. How can we find more time?

The funny thing is that anything can throw off that schedule. I was traveling to Portland so I missed a week and before that, I was working on a project.  Anything can throw it off.

I’ve been thinking a lot lately about, what Nathan Berry was talking about in his newsletter—having podcasting seasons. Instead of having a show that happens every Thursday forever and ever, taking a show and doing a block of ten. Then doing another block of ten. I might try that out.

That’s interesting.

Yeah, but the disadvantage of that is the habit of shipping something once every week forces you to do that.

Just knowing that I have to put that out every week or write a newsletter every week really helps me personally. But I think there’s some merit to the concept of working on ten episodes, sending those out and taking a break.

“Failure is the type of thing that you don’t naturally want to share, but people love hearing that because we all struggle as human beings.”

That’s interesting coming from Nathan Berry. He’s the “don’t break the chain guy.” He wrote for one million days straight or something like that.

That’s why that whole post is so interesting.

I’m friends with Nathan, we’ve talked about these things before. It's also great that we have all of these people who are being very transparent about their whole process.

We can hear about Nathan having this unbroken string of writing and then, when he breaks it, he lets us know.

The transparency is authentic.

Everyone wants to appear perfect online. I try to publish once a week—if I could I’d love to actually do that.

In reality it is more like once every month. I have other side projects and things at work that prevent me from doing a ton of interviews.

Nobody’s perfect.

It’s one thing to say writing every single day helped me, because that’s good advice. Hey, it helped him, maybe it’ll help me. But we’re also human.

I’ve had Nathan on my show a couple of times. The best moments are when he, or anybody, admits that they've failed.

Failure is the type of thing that you don’t naturally want to share, but people love hearing that because we all struggle as human beings.

This idea that there’s this person who’s perfect and I’m going to listen to everything he says—I don’t think that’s what people want. I think people want something that’s real.

“A zero-sale product from a guy who runs a show called Product People. Talk about a jab to my reputation.”

Well, I’ve got to ask you now, what were some of your hardships?

There was a project I was working on. I thought it was a great idea.

I decided to take a break from Product People, what I told people was that I was going to sort of shut the show down and maybe never start it again.

I thought, what would be the perfect product to sort of wrap this up? You know those CD box sets you used to get from The Eagles or other bands? I thought it would be cool if I created a Product People box set.

There was a ton of video—you’d get an e-book describing the process and everything that we used to produce the shows.

I thought it was an awesome idea. Product People listeners bought products—they were the primary purchasers of my books. They were the primary members of the Product People Club.

I put this boxed set out. You know how much I made? I got literally nothing—nothing as in zero sales. At least I took preorders for it and didn’t commit to building the whole thing.

Whenever any of us release something, there’s this pressure to succeed. I’ve talked to tons and tons of people and every successful person has a story like that.

I’ve seen people who’ve had successes earlier in their career and then when they follow it up, they just have so much struggle, they’ll have a string of things that just don’t go well.

That’s one for me. A zero-sale product from a guy who runs a show called Product People. Talk about a jab to my reputation.

But you came back! And now the show’s back on air and you’re still meeting cool people.

The lesson is make good stuff, and good stuff that people want.

All of those things that you tell your wife late at night—nobody likes my stuff, my blog is crap, I released this thing and nobody cared, and those sort of depressed moments we have when we’re talking with our significant others.

I felt all those things. The truth is that I think everybody feels those things at some point. Feeling those things is hard. You just have to get back up and do something else.

These days, I feel like I’m just not creating enough. I wish I could put something out every single day. There’s just so much benefit to having an idea and then putting something out. That’s what I like about podcasts is that you have the interview, you edit it and you put it out.

You’ve had some pretty impressive guests, especially in the early days of Product People. You had Patrick Mackenzie and Sasha Grief and Rob Walling.

These guys are pretty big in their respective groups. How’d you get them to be your early guests?

It’s funny for me to think about this now because it’s so easy to connect with people now. Once you know a bunch of people, you can connect with them. Rewind to the beginning and I was just this guy living in Edmonton, Alberta that no one really knew about.

Early on Kyle and I gathered a small audience—maybe a hundred people? I have no idea. As soon as we had those hundred, I sent out a survey asking them who they would like to see on the show.

Patrick Mackenzie was on the top of that list. Maybe ten or twenty people responded. I tweeted him a screenshot of that chart and said, “Patrick, you are the number one person my audience wants to hear from. Would you come on the show?” and he agreed.

That’s a pretty good trick.

Doing that interview was a big deal at the time. If you listen to that episode, I’m nervous as hell.

Let’s see, Rob Walling—I had 37signals offer me a job at one point. I flew to Chicago and interviewed with Jason and David, I ended up turning down the job but I kept in contact with them.

I had booked an interview with Jason but he had to cancel. And so I thought that this would be a great way to invite somebody is to say, “Jason Fried just cancelled on me. Can you do it?” That’s exactly what I emailed Rob Walling.

Jason Calcanis, he’s another funny one. Because he’s probably the biggest name in terms of people I’ve interviewed. I just think I wrote him a really good sales letter. So when you write a sales letter, you always make it about the other person.

It was something about how you’ve always been an inspiration, here’s some things I really appreciate about you and your show, I tried to tap into things he’d find  interesting.

He just emailed me back in five minutes. So I must have caught him at the right time, and he emailed me back and said we’ll record it right after his show. He did it right in his studio.

Justin Jackson Studio Black
Justin Jackson Beard Sky
Justin Jackson Angry Teeth
Justin Jackson Vintage Antique
The many faces of Product People Podcast Producer and Host Justin Jackson.

Going back to those first episodes of Product People, tell us what those interviews were like and how you interview people today.

Some people really like those first episodes, because of the vulnerability, especially between Kyle and me.

We were just very vulnerable and we didn’t have that much confidence.

The early interviews were very thought out, questions written down, we set a flow to the thing. I rushed way too much in those early interviews. When you’re starting, you’re just so nervous, you’re trying to see what question’s next and listen at the same time, and just hearing him start to answer the question is such a relief, but then you’re thinking about the next question.

Now, I actually don’t write anything down before interviews. Sometimes I’ll have a few talking points, but it’s a very sparse outline. One of the things I’ve learned to do is not rush.

And you’ve actually done this a couple of times, when someone answers a question, your natural inclination is to keep the momentum going and go for another one. But slowing it down, backing up to something said earlier, and asking them to go back to that moment and just talk that through—I've gotten some really great answers from that.

I’ve been trying to work that more into my interviews a lot more lately, and I think that that’s one thing people might notice is, that I’ll be like, “OK, let’s just stop and back up a bit.”

With these interviews, I’m curious what your process is.

When I reached out to you, I just cold emailed you and said, “Hey, let’s do this show!” then we emailed back and forth, you came on and did a bit of a brief. Now we’re interviewing.

What is your process for interviews, onboarding guests?

First of all, someone who’s really good at this is Bryan Castle, he’s really good at this. I used to have a better way of doing this, especially when I was kind of really scheduling things out and shipping an episode every week.

Nowadays, especially now that I have more contacts, and maybe I’d like to change this, but now I just try to be real casual. I ask them if they have time in the afternoon. If so, we record.

That’s probably something that I can do more because I have those contacts, but there’s some guests that I definitely schedule out way in advance because I just don’t know them as well.

I just interviewed Nir Eyal, the author of Hooked, which is a book about building habit-forming products. I scheduled him way in advance, and tried to do a better job of letting him know what it’ll be like.

It’s similar to what we just did. The guest gets on, I’ll feel them out. Sometimes they’re in a rush, sometimes they just want to chat for a bit and build rapport. Then I’ll just say, okay. Let’s do this.

Sometimes I say, “Okay. We’re done.” And I just keep it running anyways. The best things come from afterwards, because they’ve got their guard down. If I get something good, I’ll ask them if I can use it in the show.

I try to keep it recording as much as I can. Sometimes we’re so nervous, it’s just good to let it ride a little bit and let people calm down.

Well, of all these people you’ve had on your show, what’s the best piece of advice someone’s given you?

Oh man. There’s been a lot.

Someone that I think is still a little bit underrated is Rob Walling. If you look into his history, he was a guy who a lot of people laughed at for a while.

He had this website called justbeachtowels.com, and that was one of his early products. He had some wedding planning sites. I think people just wrote him off as someone working on things that were not terribly meaningful.

A few things—he’s been able to build a really good life from his products. I appreciate the way he structures his life. Second, he had this building block approach. He was going to start with beach towels, but build something else, then something else. Now he has a full SaaS product called Drip.

The advice he gave me, it’s not his quote, and I don’t know who originally said it, but it is, “The harder I work, the luckier I get.”

I just love that quote. I think it’s a great quote, especially when I’m feeling kind of vindictive or jealous. It makes me feel like, I’m just going to keep moving ahead. And yeah, maybe I don’t have as much time to invest in it as other people do, but, I’m just going to keep pushing this forward every chance I get.

I’ve had people tell me that I’m lucky and I’m like, what are you talking about? I’m small time. But for them, they just feel like I’ve done a ton of stuff.

So yeah, I love that quote of work hard and the luck kind of follows.

Sprintly Artwork
Artwork on the wall at Sprint.ly's office.

Well let me ask you this. Do you think you work too hard or too much?

Yeah. Yeah, I do.

I have this post that tells this really vulnerable story of me. I was working towards my master’s degree. I’m in my early 20s. We were having our second baby, I was working full-time, I’d started these two snowboard shops on the side, and it’s just talking about me juggling all these plates and just being this young twenty-something and just feeling invincible.

The problem is that, if you’re working that hard, you have no buffer. As soon as something happens, it could be anything—someone gets sick. You just have no energy or time to deal with it.

I’ve tried to adopt this principle of kind of leaving some reserves. That means spending only eighty percent of my energy in the day, only eighty percent of my focus, and trying to keep some reserve for myself every day.

I’m not always successful, but when I am, it’s really helpful. But that experience, because the plates really came crashing down. I experienced depression for the first time in my life. I always thought depression was just this weird thing that affected weird people. Things really crashed down.

Now I try to remember that and be more purposeful about leaving some gas in the tank in case maybe one of my kids gets sick, maybe things really get hard at work, I’d like to have something there so that I can use my reserves to get through it.

Instead of going pedal to the metal, North Americans really like to do this, just going right up to the edge, but I think there’s a lot of wisdom in pulling back, and kind of meaningfully pulling back.

I’ve worked hard enough today, I’ve accomplished three big things. Do I really want to work for a fourth or should I be all right with three? Because that’s a great day. And that’s something I’m working on all the time.

Well, that’s something I should probably think about.

I’m curious, selfishly, about podcast sponsorships. Who was your first sponsor and how did you come by them?

My first sponsor was Sprint.ly.

Ah!

Thats right, they’re who I’m now working for.

It’s a rather interesting story. So, when we thought about getting sponsors, Product People had between two and three thousand downloads an episode.

It’s not huge, but not tiny either. Generally, the kind of accepted wisdom is that you need at least ten thousand downloads a week before you're worth sponsoring.

Some people will do a show every day of the week to get ten thousand, some people will increase their number of weekly shows to do it. But ten thousand a week is kind of a good barometer. We had less. Maybe two to three thousand.

Sprint.ly was one of my favorite products, still is, and we were using it at work. I was just passionately already telling people about it and so I just wrote them an email. I told them that I loved the product and would like to be an ambassador—that could include me talking about it with the podcast, include me tweeting about it and just being the guy that people knew was talking about this product.

I also didn’t want to sell sponsorships and have to redo them, so almost all of our sponsorships were recurring every month. We basically said one sponsorship slot is $500 a month. That’s how we sold them.

At our peak we probably had four or five sponsors. That was probably a little bit too much.

And how does that work? One sponsor gets the slot at the very beginning of this show? They move down the next week to the five-minute slot?

Yeah.

So when I had a lot, it was very difficult at that point. But when I had a lot of sponsors, I had to space them out each time.

I think if I were to have sponsors and do it again, I would do the season approach and say, I’m coming up on my 2015 winter season and to sponsor this block is this much money.  I’d probably do it that way instead, because monthly is that it was just so much more pressure to ship an episode no matter what.

So I got the first one by just reaching out to a product that I really loved. It worked out really well for Sprint.ly because they had this passionate ambassador.

It worked out well for us as well, because that sponsor led to other sponsors down the road.

And I guess, getting in the details, did you sign a contract or did you just send them an invoice and say this is it? Did you make a separate company for Product People?

At the beginning.

Kyle transitioned out shortly after we got sponsors, in part because we had this pressure to deliver an episode every week.

We didn’t sign a contract. It was just kind of a handshake, well not even a handshake, just a verbal agreement.

An internet handshake?

An internet handshake.

I just sent them an invoice, and for recurring, told them to go to this website, put in your credit card and it’ll bill you every month.

“Get momentum. Once you feel like you’ve got something that’s a good product, tap into people who have bigger audiences than you.”

That’s interesting. And as far as legal stuff, did you have something set up specifically for Product People, did you have a Product People bank account?

No, we didn’t do that.

Actually, I just recently set up my own business bank account. I’ve had business bank accounts in the past, like with those snowboard shops. But all my side projects have just been the money goes from Stripe into my personal account or Paypal into my personal account. We never had a separate bank account.

Whenever I’ve done partnerships where I split money, we just split the money. It goes into Paypal, you get some and I get some. I think that that arrangement is very helpful at the beginning.

Bank accounts and everything else put so much load on top of a little thing that could not do very well. I think if you’re already consulting or whatever, it makes sense to set up another company and a bank account. For side projects, I think you could even just open up another personal account, which are way cheaper, and just manage it that way. And then on your taxes, you just claim it as additional business income.

You do have to pay tax on that, so be careful. But that’s how I did it and it served me well.

Well, I know these are probably very dry details, but I’m always interested in how that works.

We’ve actually been talking for almost an hour. I guess if you’ve got any advice for someone like me or someone who’s trying to build a podcast or something similar, what would that be?

My advice with everything is start small and ship it.

That’s the first thing. I started Product People with these iPhone headphones and microphone.

It was okay because we started small, we shipped one episode and maybe five people listened. But that’s the key. Get momentum. Once you feel like you’ve got something that’s a good product, tap into people who have bigger audiences than you.

It could be an individual or a website. Figure out who has a big following. Interview shows are great for this because the interviewee is very likely to share the show after they’ve been interviewed. So I would say start small, start putting stuff out, put stuff out when nobody’s listening.

Once you kind of get your game on, then reach out to people and then see if you can offer them something. Figure out what they need, and then in return, it’s very likely that they’ll say, oh yeah I’ll share that show, or I’ll share what you’ve done. That’s my advice when you’re starting.

The other thing is that I just hustled. I put my podcast in every single online directory. I was hustling on the side too, which I think helps. But what really helped was shipping that first episode and then finding influencers who could help kind of spread the message.

Great words. Thank you for joining me. Where can people follow you?

Best places is my website justinjackson.ca.

Justin, thank you for being on the show.

I really enjoyed the conversation. Thank you for having me.