Josh Pigford on Shipping, Hiring Smart People, and Not Being Epically Wrong

My guest today is a self-proclaimed maker — but I would call him an entrepreneur, writer, designer, developer, and master marketer.

My guest has been developing and shipping products online for over 10 years now and has seen his share of successes and not-so-successful ventures.

He is currently the founder of Baremetrics, software analytics and reporting for Stripe. Baremetrics seemingly came out of nowhere with an awesome content marketing strategy, lead by my guest, on the Baremetrics blog — one of the best software business blogs on the Internet today.

Now, let’s hack …

Josh Pigford.

In this 26-minute episode Josh Pigford and I discuss:

  • How shipping is always better than perfect
  • Why Josh cannot work for someone else
  • Josh’s steps to hiring awesome people
  • The long list of things that Josh is not good at
  • The number one way Josh has built Baremetrics into a successful startup

The Show Notes

Josh Pigford on Shipping, Hiring Smart People, and Not Being Epically Wrong

Jonny Nastor: This is Rainmaker.FM, the digital marketing podcast network. It’s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at

Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big name entrepreneurs and those on their way to joining them. Now here is your host Jon Nastor.

Jonny Nastor: Hey, hey, welcome back to Hack the Entrepreneur. I am so glad you decided to join me today. I’m your host, Jon Nastor, but you can call me Jonny.

My guest today is a self-proclaimed maker, but I would call him an entrepreneur, writer, designer, developer, and master marketer — although he may cringe at that last part.

My guest has been developing and shipping products online for over 10 years and has seen his share of successes and not so successful ventures. He’s currently the founder of Baremetrics, software analytics and reporting for Stripe.

Baremetrics seemingly came out of nowhere with an awesome content strategy led by my guest on Baremetrics blog, which is one of the best blogs about the software business on the Internet today.

Now, let’s hack Josh Pigford.

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Welcome back to Hack the Entrepreneur. Today’s guest is somebody I’ve been wanting on the show for quite a few months.

Josh, thank you so much for joining me today.

Josh Pigford: Thanks for having me, Jon.

Jonny Nastor: My pleasure, my pleasure. Alright, Josh, let’s jump straight into it. Josh, as an entrepreneur, can you tell me what is the one thing that you do that you feel is been the biggest contributor to your successes so far?

How Shipping Is Always Better Than Perfect

Josh Pigford: I think the main thing is the shipping, not getting caught up on this idea of ‘perfect.’ The saying’s like, “Shipped is better than done or perfect.” I’ve totally just botched that. “Shipped is better than perfect” — I think that’s the saying, but that’s like the general idea there. That getting something out the door is much better than getting something perfect out the door because, in reality, especially in software, perfect doesn’t really exist.

Jonny Nastor: Yeah. You’ve been shipping for over 10 years now?

Josh Pigford: Yeah, I’ve probably built my first real thing at least 10 years ago.

Jonny Nastor: Wow, nice. It seems, from the outside, I didn’t know who Josh Pigford was until I believe last June maybe, or was it June or July. Somehow you ended up on my Twitter. Then you were doing those lunch hour Q&A things.

Josh Pigford: Yeah.

Jonny Nastor: Those were awesome. Then all the sudden, it was just Josh Pigford from then on, but you were at it for a long time before that. There seems to be this time in every entrepreneur’s life, they realize one of two things — either they have this calling to make something big in the world or they simply cannot work for somebody else. Josh, which side of this fence do you fall on?

Why Josh Cannot Work for Someone Else

Josh Pigford: I’m pretty firmly on the I can’t work for anybody else. I’m not like a we’ll-get-in-lots-of arguments and we’ll-hate-each-other kind of bad employee. I just get zero fulfillment from building somebody else’s thing. For the longest time, I was splitting my time between building my own stuff and also doing consulting work. I enjoyed the winning a contract side of things, and I enjoy just building things because it’s fun. But at the end of the day, you’d ship something for a client, and then that was sort of it. I just didn’t care about it.

I’ve always been the kind of, I’m just going to build my own thing. I probably should clarify there. I don’t build stuff for the web because I don’t want to work for somebody else. I build stuff for the web because I like building stuff. That’s probably the main driver. It’s just fun to build a thing.

Now, whether that’s from the design side or the development side or the management, like “Let’s get the team on board, and we’ll all build the thing,” I’m kind of indifferent on that. But the idea of just building a thing as a solution to a problem is pretty motivating for me. I just need to have a lot of skin in the game for it to really be fulfilling.

Jonny Nastor: Fair enough, fair enough. So zero fulfillment building somebody’s else’s thing, and maybe you’re not the worst employee. You think you just don’t get the fulfillment. I’m wondering, just with the growth of Baremetrics over the last year, is there things that you, when you ever were an employee, that you didn’t like about bosses that you’ve consciously decided not to do?

Josh Pigford: No. In reality, I’ve had one ‘real,’ I’m-just-a-cog-in-the-machine job, and that was 10 years ago. It lasted for seven weeks.

Jonny Nastor: You really can’t work for somebody else.

Josh Pigford: I don’t know. Yeah. I was fresh out of college. I went to go work at an interactive design firm, and that’s slave work. It was the salary. In hindsight, I didn’t know any better. I was just right out of college. I took this job offer, and then after seven weeks of commuting and realizing this isn’t fun, I quit and haven’t looked back. I’m probably the wrong person to ask there. It’s been awhile since I’ve had a real job.

Jonny Nastor: Nice.

Josh Pigford: And I never really had a real job.

Jonny Nastor: Fair enough, fair enough. It seems from the outside that you spent 10 years where maybe not as many people, obviously, knew about who you were. It seems like that whole 10 years to an overnight success type story. How do you deal with the idea that you really didn’t know how to be a boss? Maybe you didn’t know how to get funding.

How do you deal with the fact that you don’t probably know the things that you have to do this week in your business. You’ve probably never had to do lots of them before, and there’s always going to be first times for all these things.

How do you deal with the fact that like, “Whoa, I’m in this position now that I have to act like I know what I’m doing?”

Why Josh Thrives on Being Clueless

Josh Pigford: Sure. For me, I actively go seek out those things. If I find myself super comfortable in some position, then I feel like I’m doing something wrong. I firmly believe that the things that are the hardest to do are, most of the time, the thing that you should be going after because, chances are, nobody else is — or at least very few are. For me, I’m comfortable or even thrive when I don’t have a fat clue what I’m doing.

How do I sort of manage that? I just kind of do it. There’s a bit of ‘fake it ’til you make it,’ but in reality, I think most — and when I say most, I mean 99 percent of people who are making anything, building any kind of business — nobody actually knows what they’re doing. They’re just throwing stuff out there. You might be making some educated guesses, but nobody actually knows how everything will play out. There’s always some step that they haven’t done before. For me, I’m comfortable there. Some people aren’t, but that’s what works for me.

Jonny Nastor: Yeah, and it’s funny because that was exactly how I was going to phrase it, was nobody knows what they’re doing, nobody. There’s always that, “How do you do this?” You just figure it out the first time, and then it’s like, “Oh, OK. Got it.” That’s how you do it, and you move on.

Josh Pigford: Yep.

Jonny Nastor: Did this come naturally to you, though?

Josh Pigford: Sure. I’m naturally a problem solver, so things that I don’t know how to do don’t stress me out. In reality, it kind of gets me pumped up. There’s some big thing that I don’t know how to do, “OK, well let’s pull it apart and see how we make that happen, and then kind of go from there.”

Jonny Nastor: Wow, that’s cool. We talked about you shipping stuff is your one thing that has been your biggest contributor. Now every expert out there tells us the whole 80/20 — do 20 percent, get 80 percent of the result — and then this whole ‘do what you’re good at, and then delegate the rest.’ Josh, in your business, what is something you are absolutely not good at?

The Long List of Things That Josh Is Not Good At

Josh Pigford: There’s a lot of stuff. I would say I’m not really a good developer, which is kind of interesting because I built the first version of Baremetrics. I was the only guy developing anything for the first six months. I would say most things I can kind of hack my way through.

I’m not good at being the best guy, like the absolute best, top-of-the-line designer or the absolute best, top-of-the-line developer or customer support guy or marketing guy. But to me, that’s where hiring people who are really great at that — like the people on our team, they’re all amazing at their jobs.

For me, my strength is combining all these things together to make something happen. Putting all the pieces together and taking all these resources and making something happen. But I’m bad at being extremely specialized.

Jonny Nastor: That’s pretty cool. I actually wouldn’t have expected you to say that you’re not a good developer because I know you built the first version yourself.

Josh Pigford: Right, but it was a means to an end. I taught myself to code a decade ago because I needed to have something built. I needed an end product. I don’t code because I enjoy coding.

Josh’s Steps to Hiring Awesome People

Jonny Nastor: Then, who’s the first person you hired in Baremetrics?

Josh Pigford: A backup, an engineer.

Jonny Nastor: An engineer, really?

Josh Pigford: Yeah.

Jonny Nastor: Nice. You were just like, “I needed help”?

Josh Pigford: I was way over my head. I had built the first version. Then it’s like, “I don’t know how to deal with data sets this large.” The house was burning down, so I had to hire that out quick.

Jonny Nastor: Was it another developer after that? How strategic were you?

Josh Pigford: ‘Strategic’ would be a generous word. Back-end engineer, front-end engineer, and designer, those were actually hired at the same time. I hired another back-end engineer and a customer support guy pretty much exactly the same time.

Jonny Nastor: Nice. During all this, you were marketing? You were the content guy from the start.

Josh on What Drives the Success of Baremetrics

Josh Pigford: Yes.

Jonny Nastor: And you still are.

Josh Pigford: Yep.

Jonny Nastor: That’s awesome. Would you say that that’s a massive part of the success of the company?

Josh Pigford: Sure, the content part, but I think it’s content and then we’ve got this public dashboard, open startup thing.

Jonny Nastor: Just last week?

Josh Pigford: Well, announced it in sort of this official capacity, but actually a year ago today is when we partnered with Buffer for them to make their dashboard public. For us, that’s marketing. That kind of stuff is what I’ve been super focused on and has worked really well for us is that sort of content, but also startup, insight kind of information stuff.

Jonny Nastor: What pushed you that way? Why’d you think that, that was what would work?

Josh Pigford: It’s sort of a natural outpouring of what we do. Baremetrics is a tool built specifically for entrepreneurs, so it’s not a survey platform that might be for more of a research position, a marketing director, or something like that, or a tool, a help desk that’s more for the customer support people. Our tool is built specifically for the people running the business. As me running Baremetrics, the easiest route was for me to write about that. It just happens to be that that’s specifically for our audience, so it works out well.

Jonny Nastor: Nice. OK, let’s move into what we’ll loosely call projects. Whether new features or this new open dashboard that went public last week, do you have a process to decide on what is a new project that you should take on? Either personally or within Baremetrics?

Josh Pigford: Within Baremetrics, a lot of it comes from a mixture of customer feedback, then features that I think long term make a lot of sense for us as a business. Maybe customers haven’t been specifically asking for it, but it’s something that either expands our market share or maybe provides a new source of revenue or something like that. Then there’s this gut instinct element that’s just me taking a stab in the dark and thinking, “This may be good for us.”

That’s kind of how I decide on the business side. Then on the personal side, I don’t really have a ton of side projects any more. I have hobbies that are completely not tech related at all.

Jonny Nastor: Like cool hobbies?

Josh Pigford: They’re all geeky, or not even geeky. I would say they’re dorky — woodworking and gardening — like old man kind of stuff.

Jonny Nastor: Fair enough, fair enough. Side projects, I guess, is something that you will probably get less and less into the bigger your company grows, right? The busier you get.

Josh Pigford: For me, they’re basically non-existent. Side projects are all analog things. It’s stuff not related to business, not related to technology. It’s completely out of that realm.

Jonny Nastor: Nice. I guess this isn’t projects, but I want to know the process of determining that you figured Baremetrics needed funding — that you got, I believe, last August it was the announcement went out. What made you decide to not just bootstrap it as you were already and as you had, I think, done in the previous 10 years on projects?

The Funding Josh Couldn’t Turn Down

Josh Pigford: The funding thing, we didn’t actively go out and look for funding. You get to a point where, especially because we were so public with our numbers, anybody could see what our growth rates were and how much money we were making and all that kind of stuff.

Jonny Nastor: You wrote posts about it all the time.

Josh Pigford: Exactly. It was a pretty common thing to have investors reaching out. Now, for the most part, most of those, the terms of those deals were never great. They weren’t necessarily bad, but they weren’t anything I was interested in.

The deal that we made last, I think we closed on it like September, yeah August or September, the terms of that deal were kind of too good to pass up, so it was sort of a no brainer. We didn’t give up any immediate shares in the company, no board seats. It wasn’t like a form of debt, so it kind of was, “Well of course we will.” If we could have gotten a million dollars at that same rate, then I would have taken that, too. The deals were too good to pass up.

Jonny Nastor: Wow. Did it you surprise you, or no?

Josh Pigford: Sure. I wasn’t looking for it. It kind of fell in my lap in July, and then within 30 to 45 days later, it was done.

Jonny Nastor: Did it make you take anything more serious? Like, “Wow, this is something real that I’m building.”

Josh Pigford: I maybe take it more serious. It probably made me look at what are the bigger possibilities for Baremetrics or that there is a bigger opportunity here because it was a scratch my own itch thing initially. For a long time, that had always been the foundation of it. I was like, “I’m just building this for myself, and let’s see what happens.” Then, over time, that has shifted as I’ve realized how big the need is. Yeah, it solidified that.

Jonny Nastor: Yeah, very cool. OK, so from all the good stuff, the quick business growth now, the funding, let’s move into say struggles and failures, if you’ve had them. Let’s see.

As entrepreneurs, as humans in general, one of our greatest struggles is the fear of being wrong, making a mistake, especially when you are the one in charge and you’re following your gut. You think, “We need to now do this,” and it turns out to be completely wrong. Josh, could you tell me how to be wrong within your business?

The Number One Way Josh Has Built Baremetrics into a Successful Startup

Josh Pigford: I think a lot of times that’s a relative thing. Certainly, I am wrong a lot, but most of the time, it’s on such a small scale. That’s a strategic move on my part — is to not be epically wrong on things, or at least not be so wrong on something. I’m answering with a sideways way of answering your question here. The key to doing wrong correctly is to not put yourself in a position to just completely blow it. When we ship stuff, we break it into smaller pieces. We just don’t hack away at something for six months, throw it out in the wild, and hope that we were right.

We did a lot of tiny little releases along the way to stick our toe in the water. Then it would adjust as we were going. I think that’s the key. This shipping fast and frequently kind of mindset prevents you from just completely screwing up in a major way.

Jonny Nastor: Yeah, avoiding being epically wrong. I like that. Well said. Alright, Josh, I’m going to end off on something I’m calling the ‘entrepreneurial gap.’ You’ve been building stuff for 10 years. You’ve been probably, often times, looking forward. I feel that, as entrepreneurs, we set goals for ourselves and things we want to do one month, three months, six months, a year, five years, 10 years down the road. Before we even get to some of these goals, we’ve already set five loftier ones in advance, but we never stop and look at where we’ve come from and the crazy stuff that we’ve gone through and accomplished.

So, Josh, could you please stop right now, turn around for me, and look at where you’ve come in the last 10 years and just tell me how you feel about that?

Josh on Building His Success Over the Past 10 Years

Josh Pigford: Sure. If you look at where I was a decade ago, obviously, I’ve come a long way. I think it’s a super gradual thing, though. A lot of times, people look at other people and think where they’re at now was where that person was a decade ago and think, “OK, I have to do this, have to become whatever they’re at now.”

Our generation or just anybody alive today that’s not older than 50, there’s this mentality — we try to have the things that took our parents 30 years to get, and we want that now. It’s like, “Well, no, your parents may have worked 30 years to get to where they’re at now.” That’s not necessarily always the case for everybody now.

I think there’s the case in business, too, where you look at people now and think, “Oh, I want to be in that position now,” but not put in the work to get it done and know that it takes a long time. It can take a really long time and, most of the time, does take a long time. When I look back, it’s exciting, but it’s not necessarily surprising to me at least. I feel like I’ve put in the work.

Jonny Nastor: And that’s good, and I think it’s true. People would look at you now and be like, “Whoa, look at him in the last two years!” But well, no, there’s eight years prior to that. To you it’s, “No, I’ve been working and working and working.” That’s cool. I appreciate the answer. So, Josh, we’ve got to talk about you and your business in passing. Can you specifically tell the audience where to find out more about both?

Josh Pigford: You can find out about Baremetrics at, read the blog, You can find me on Twitter @Shpigford, or shoot me an email,

Jonny Nastor: I forgot you have

Josh Pigford: Oh, yes.

Jonny Nastor: That’s awesome. I still have it as .io on my machine.

Josh Pigford: No, not any more.

Jonny Nastor: Very cool. I will link to your Twitter and to Baremetrics in the show notes for everyone. Josh, please keep doing what you’re doing, man, because it’s awesome to watch. Thank you so much for taking the time to join me today.

Josh Pigford: Yeah, thanks for having me on, Jon.

Jonny Nastor: Mr. Josh Pigford everybody. Josh, that was fun. I thank you so much. I’ve wanted you on the show since I launched, and I finally got you. I’m so happy.

Baremetrics blog, even if you don’t need Baremetrics right now in your business, as content marketers, you need to see what Josh is doing because Josh is doing amazing things. He’s building a business based on growing an audience first through his content. He’s just really, really nailing it. He’s working his ass off, and he’s doing a really, really good job.

So check out Baremetrics blog. I will link to it in the show notes if that makes it easier for you. Otherwise, just look up, and there’s a blog.

Josh, you didn’t let me down, man. It was a great conversation. You said a lot of smart things. There’s a lot of things that he said, but there was one thing, wasn’t there? There was. There was one thing he said. Did you get it? Did you hear it? Let’s do it. Let’s find the hack.

Josh Pigford: The things that are the hardest to do are, most of the time, the thing that you should actually be going after because, chances are, nobody else is — or at least very few are. For me, I’m comfortable or even thrive when I don’t have a fat clue what I’m doing.

Jonny Nastor: And that’s the hack.

Josh, Josh, Josh. Thank you. You are so right. The things that are the hardest to do, are usually totally the things that we should be doing and that are worth doing. Then to finish it off, I love how Josh is comfortable. He loves to be putting himself into positions where he doesn’t have a fat clue what he’s doing.

We need to do this. This is just an exercise. This is just a muscle. Getting used to this uncomfortable feeling of not knowing what you’re doing, it just takes practice. It’s really, really hard to do at the beginning. Josh has been doing this for over 10 years now online alone. He’s gotten used to it, and his success is proof of it. This is something that we really, really need to do.

To go back to that, the things that are hardest to do, that’s like this concept that I talk about all the time, Seth Godin’s idea of ‘the dip’ — the bigger and longer that that dip is, the harder those stretches are to get through, the bigger the rewards are on the other side, because 90 percent or 99.999 percent of the people, if that dip and that thing is really, really hard to get through, they don’t make to the other side.

In this business, with podcasting, most people don’t make it through those dips. They just don’t. They start. They get all excited, and they go as hard as they can. Then audience starts to fade a bit, and they just give up because it’s hard. There’s no direct reward. The reward is massive, but it’s through these hard, hard places. Absolutely the harder that place is to get through, the more you know that you have to get through it because the reward on the other side is huge. Josh, thank you so much.

All right, this has been a lot of fun, as always.

This is coming out and I’m on a road trip with my family across your beautiful country of the USA, if that’s where you live. I’m from Canada, but we’re going through the northern parts of the States, from Ontario, or Minnesota I guess it would be down there, across to Washington State. Then we’re going up and going to spend the summer in Vancouver, BC, Canada.

If you happen to be around any of those spots in between or in Vancouver this summer, hit me up. I would love to hear from you. I’d love to take you out for a coffee and chat if we could.

It’s going to be a lot of fun. Thank you so much for stopping by. You have no idea how much I appreciate it. I really, really, really do. I think it’s really cool that you’ve decided to take the time with me.

So, please, have yourself a great day. Until next time, please keep hacking the entrepreneur.