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Breaking the Mold: Your Career, Your Way

Travis Nichols on April 17th, 2014

The group of coworkers huddled around a laptop. The laughing, salad-eating woman. The suited man yelling into a megaphone. The eager post-grad with an outstretched, fill-in-the-blank business card.

These are exactly the kinds of stock photos that Death to the Stock Photo pushes back against. Instead, Allison Lehman and David Sherry release sets of themed photos without the flat, white backgrounds and plastic expressions that the go-to stock photo companies pump out like combo meals.

Most photographers work on an hourly rate for events and contract gigs, and there’s not much of a way to break through that paywall without hiking rates or trying to sell prints. But… prints?

(altered photo from the ‘Lake” series)

We talked to David of DttSP about their new model of photography and an upcoming 5-city trip that will fulfill a longtime dream.

How did the idea for Death to the Stock Photo come about? What were you and Allie doing before this?

Allie and I were both freelancing full time, and it started out as us just sending our designer/blogger/creative friends photos to use in their projects. I was just out of school (last May) and Allie was running The Wonder Jam, which she still does today.

We had a common pain where you work really hard creating something beautiful for a client, only for them to send you a pixelated, generic photo to use alongside your design or website. It just felt inauthentic. We’d actually preferred they hire someone for it but sometimes it’s too costly for newer businesses. Being that we both were photographers on the side, we decided to just open up our library to our friends to use however they wanted. After getting a great response on that we started shooting once a month for the email package we’d send out. We shoot in themes like coffee shop, city, park—anything we thought would really serve and inspire our communities’ projects.

(altered photo from the ‘Brick & Mortar Pack”)

One interesting piece of my story is that right out of school I had this dream that I could get a brand to sponsor me to go on a road trip. I pitched multiple companies on a campaign to drive around the country creating photo and video content for them in exchange for funding the adventure. In the end I got all NOs, so it’s kind of cool/ironic that I’m doing a similar trip a year later with an audience of my own. Something I believe in now is that you can’t wait for anyone to “pick” you. You’ve got to pick yourself.

What’s your favorite cringe-worthy trope of traditional stock photography?

For me it’s all about the lighting and the staging, I guess. Lighting is such an important piece of photography, and many of the common cringe-worthy stock photos just have this weird superficial flat lighting that I honestly don’t even know how they create. I think they might have a filter that they put on it. Someone should create a “stock lighting filter” for Instagram.

Your upcoming project is an invitation. “Let’s adventure, together.” Tell me about the 5-city trip you’re taking.

With the support of our community we’re heading across the U.S. to take the most authentic imagery we can and tell the stories behind them. We’ll be hitting Big Sur, Seattle, Nashville, Chicago, and NYC. While some of it will be structured, we’re trying to make the content as authentic as possible, so we’re hoping for as much serendipity and real adventure as we can. Our brand is really about death to “stock” with stock meaning the average and generic. So we really want people to push beyond the “stock” lifestyle to pursue their dreams and push to create their own path versus one that’s standardized.

What place are you most excited about?

I’m most excited about checking out Big Sur. I’ve heard so many good things about it and I think I’m camping around there for part of it. Plus there’s a marathon going on there which will be awesome to see. Marathon people are usually awesome, so I’m hoping to meet some fellow travelers and hear their stories. Other than that, I’m in love with the energy NYC has so that will be special for me as well.

Do you have any specific notions of the sorts of things you’re looking to shoot?

We have some general outlines of what we want to shoot, but it’s funny because there’s this tough paradox. The more you plan, the more that planning comes through in the photo, which isn’t always bad, but the type of photography that I love is real and in the moment. There’s a delicate balance here, so we plan on having a loose structure on themes (similar to our monthly emails) alongside giving ourselves time to really get to know the city through our lens. 

What will buyers receive?

Our buyers (any amount they can afford) will receive a pack of 20+ photos every few days from each location. With that pack comes stories from the road; photos they can use in their own projects as they’d like, and hopefully a view of the city that they could apply to their own travels. We’d love for people to visit a city after and feel like they know some of the cool locations and cafes from this, kind of like a city guide.

What sorts of cool uses have you seen for your stock photos so far?

The best thing we see on a monthly basis is this dynamic between ourselves and our community. We create a pack, send it out, and then see all of these people just make something beautiful with it, be it a blog post, design, or website. Something in particular that was pretty cool was that we put out a local band-themed photo pack, and this guy emailed us after saying, “I finally mocked up this music app I’ve been thinking about because of this photo pack.” I loved hearing that.


There are still a few days to sign up to receive photos from the Death to the Stock Photo cross-country trip. Go to The cutoff is April 20th! And to receive monthly stock photos, go to

If you’re a photographer, designer, writer, musician, developer, filmmaker, or any other type of creator, what can you do that would break the established mold of your craft?  We’d love to hear about what you’re working on.

How About Recommended Products?

Travis Nichols on April 14th, 2014

You just bought an issue of a digital fashion magazine. Very nice. Say, how about The Ultimate Guide to Cufflinks?

Recommendations from Gumroad is a new opt-in feature that will allow related products to show up after purchases are made. If you enable recommendations, your products will be recommended to buyers of other products, and likewise, after the purchase of your products, related projects will be shown.


You can turn recommendations on in your settings.


Once activated, up to three recommendations will appear after a purchase of one of your products is made (once we’re able to recommend related products). Note: a product must have a cover to be included. But of course your products have covers.

How does this work? To find and recommend related products, we look at the intersection of buyers of a seller’s products with buyers of other people’s products. If that “signal” is strong enough, and we deem a product recommendable, we’re show it to the buyer. Recommendations can come from other sellers’ products and/or your own products depending on purchasing habits.

As your sales increase, and as more Gumroad sellers opt in, this feature will become more and more robust.

When a product of yours is purchased via a recommendation, it will show up in your analytics as “Recommended by Gumroad”.

We’d love to hear your feedback on this feature. Please let us know what you think. And if someone out there is working on an Ultimate Guide to Cufflinks, we’re extremely interested.

Your Gumroad Gallery

Travis Nichols on April 9th, 2014

Your profile page is now a customizable gallery. Reorder and scale your covers to showcase your products. Descriptions and buy buttons appear when you hover over covers.

When logged in and on your Gumroad URL, you’ll be able to stretch and reorder your covers in many different ways. Tall columns, multi-tiered rows, large squares flanked by smaller squares. It’s up to you.

You might need to rethink your cover images depending on how you lay out your page. In the video above, you’ll see how images crop when adjusted. Here’s a list of recommended cover sizes in pixels. These are ideal especially if you sometimes share single product pages.

Square: 700 x 700 (single or double)
Tall rectangle: 333 x 700
Wide rectangle: 700 x 333
Wider rectangle: 1066 x 333

Note: A wide rectangle will also serve to keep your purchase button “above the fold” when viewed on an individual product page.

What hasn’t changed is your ability to change highlight and background colors, add a background image, and hide/show projects on your page. This can all be done in the left settings panel.

So if you’re looking for more of a shop feel (with bundle buy), the new gallery view is a great solution.

We love hearing your feedback. Tell us what you think of this updated feature.

How to Showcase Your Expertise through Content Creation

Travis Nichols on April 4th, 2014

For the second edition of The Gumroad Creators Studio, Poornima Vijayashanker of Femgineer gave a talk on content creation as a launching point for entrepreneurship.

Poornima started as a blog to combine her interests in engineering and writing. After, much to her surprise, people starting reading it, she pivoted Femgineer into an educational business. Now Femgineer is speaking engagements, workshops, mentorships, online courses, and more.

We were happy to host Poornima at Gumroad HQ, and we’re glad to share her talk below. If you’re interested in leveraging your expertise in anything from coding to screen printing, from design to pet grooming, from technical writing to urban gardening, this is for you.

Making Great Videos with Caleb Wojcik

Travis Nichols on March 28th, 2014

Caleb Wojcik, co-founder of, The Fizzle Show, and The Sparkline Blog, created a definitive crash course guide to making better videos. The DIY Video Guide takes you from gear (and the gear you don’t need) to audio to shooting to editing (with a trove of tricks to save on editing time), and everything on the software side. In addition to the book, higher packages include video tutorials, interviews, case studies and more. I talked to Caleb about the guide and video-making in general, and how I could have saved countless hours of my life if his book had come along just a little bit sooner.


Starting from absolute scratch, what’s it going to cost someone to make good-looking, good-sounding, engaging videos?

Assuming you have a smart phone made in the last few years, you can start making good-looking and good-sounding videos for about $100. The three pieces of gear I recommend for making great-looking iPhone or Android videos are a RodeSmartLav ($60), the Glif Phone Tripod Mount ($30), and a small Gorillapod ($18).

Engaging videos, on the other hand, don’t cost anything but time. Time spent planning and scripting a compelling video, time recording take after take until you land that joke correctly, and time during editing making sure the video is as concise and clear as possible.

What are some of the biggest DON’Ts you see in videos out there in the cultural milieu?

One of the biggest mistakes I see is publishing videos that are way too long. The French mathematician Blaise Pascal once said, “I would have written a shorter letter, but I did not have the time.” A video that is too long is one that didn’t have enough time spent making it. The creator didn’t plan it out well enough or edit out enough fluff. 

Think of a director’s cut of a movie. Even in Hollywood, at some point you can’t just leave everything in. Videos that take too long to accomplish what they set out to do are a waste of time for the viewers and ultimately show a lack of polish by the creator.

What are the least-used and most-used pieces of video equipment that you own?

My least-used piece of video equipment has to be an LED light that just sits on top of my DSLR. I always bring it just in case I need it but I always default to natural light or setting up a three point lighting kit.

The piece of gear I use the most would have to be my tripod or monopod. I can’t stand shaky camera footage. I don’t mind it in a movie or show that is using it stylistically (see: Bourne movies), but if a video is shaky when I go to edit it I almost always throw it out.

We’ve got some more content coming out soon on improving conversion rates. One of the things we looked at was conversion rates for products with different types of covers (product previews) - image vs. video vs. audio. However, the vast majority of creators on Gumroad who use videos for covers are filmmakers. What sagely thoughts do you have about using video previews for other types of projects?

Don’t be afraid to show your face. In my experience, people buy from people easier than they do from mysterious brands. Hop on camera and explain to the viewer what it is you’re selling, in your own voice, with your own quirks and mannerisms.

Also, show the inside of your product, service, or company. Buyers want to see behind the scenes. Show them the inside of the book, the membership site, the factory where you make the shirts, or kitchen where the sausage is made. Think of it like special features on a DVD.

Caleb, the three-snaps-to-signal-a-mistake technique (see the book, readers) is fantastic. I’m currently digging through stacks of raw footage for some upcoming videos, and that would have saved hours of work if I had known about it before. I’m absolutely going to start snapping my mess-ups. Do you have another other quick video hack that you didn’t mention in the book or accompanying materials?

Always do two takes when possible. Even when I think I nailed the line the first time I always say it again. More often than not I will have made a funny face, said a word incorrectly, or had some other audio hiccup that I didn’t expect. Hard drive space is cheap. Taking the time to set up all your equipment again just to say one line is not.

It’s been around a month since the release of the DIY Video Guide. You talk about hitting the record button every day. That’s a month of work for you. Have you leveled up in that time (streamlined a process or two, picked up some new skills, etc.)? Or, Caleb, have you peaked? Oh no. Did you peak?

I actually worry about this. After you do something for a while, in my case making videos, it is easy to stop learning new things all the time. So what I’ve been spending some time learning lately is color correction. I always make sure that the image of the footage I shoot into the camera is publish-ready, but being able to stylize and adjust the colors of a shot just a little bit can go a long way towards upping the production value of your videos.

What part of video-making do you still find the most challenging?

Being myself on camera is something I still have an issue with when I’m working off a script. When I am just ad libbing or doing more of a tutorial where I can talk naturally it isn’t really a problem, but when I have to deliver a specific line or joke that I’ve written, it still takes me too many tries to not sound like a robot.

You offer the DIY Video Guide in three packages. What are some of the benefits of the packages that include more than the book alone?

What you get in the other packages are threefold. First, there are video tutorials from me on all of the more technical parts of making videos like the software you’ll use to edit and syncing audio with video recordings. Second, I have case studies of different kinds of videos I’ve made including book trailers and sales videos. Lastly, I have video interviews with online entrepreneurs that heavily use video day-to-day in their business, but do the majority of it themselves. These all add a more detailed and step-by-step look at how DIY videos are made.

The Gumroad team are big fans of Fizzle. (Readers, Fizzle creates products and content for indie entrepreneurs.) Anything exciting in the pipeline you can share?

We have some great “guest” courses that either just launched or are coming soon to Fizzle. One of which is an official course from Michael Port’s team called Book Yourself Solid. We’re also putting the finishing touches on an Advanced Podcasting course with John Lee Dumas of Entrepreneur On Fire. And that’s not even to mention the great things our Fizzle members are accomplishing and sharing in the forum. I love all the Fizzlers. They rock.


Find Caleb Wojcik’s blog, podcast, and book at

Feature Update: Import Customers into Gumroad

Jessica Jalsevac on March 26th, 2014

With no setup fees or contracts, its always been easy to switch to Gumroad. Recently we made it even easier with our new customer import feature. Now you can bring your entire customer list from all other platforms into your Gumroad dashboard with just a couple clicks.

This makes it easy to quickly deliver updated versions of your product and keep customers informed of product announcements all from one place.

Or perhaps you have a digital reward, such as a film or album, that you want to send to your Kickstarter backers. Simply import your backer list and send away. Bonus: Gumroad doesn’t charge for delivering free content!

Here’s how its done:

From your Customers Tab, click “Import” below your buyer list.


We provide you with a handy template to organize your data for import. Download the template and add in your customers email address (and purchase date if you’d like). Be sure to keep the headers and format as is for smooth importing.

Then just select the appropriate product, and upload your CSV.


You even have the option to send an update containing all your product’s files to your imported customers, so they’re immediately caught up with one click.

Voila! We hope this helps simplify your life and deliver an even better experience to your customers. As always, we welcome your feedback - let us know what you think at, or @GumroadHelp.


Your Meeting with a Room Full of Experts

Travis Nichols on March 18th, 2014

You’re an entrepreneur with a great idea. You and your team are huddled around your kitchen table 16-20 hours a day building an awesome product. You get an email from Dropbox. You’re out of storage space. Halfway through reading the message, your computer dies.

Alright. It’s time to raise money to get you out of the apartment and into the world.

We talked to Michael Simpson, DJZ co-founder, about the book he co-authored with Seth Goldstein, The Secret of Raising Money. This comprehensive collection of knowledge from top venture capitalists in Silicon Valley and beyond promises to help you spend less time raising, get your foot in the doors of top investors, and know what to say once you get inside.


Sahil, our founder and CEO, said, “If you can’t get an hour with Seth, read The Secret of Raising Money”. That’s what I find most striking. This is productized consulting. When you and Seth were working on this project, did you have that in mind? That this essentially puts the reader/viewer in a room of experts that they, frankly, likely couldn’t get meetings with otherwise?

Definitely. Raising money is very difficult, especially if you don’t have access to mentors to guide you. So we took the best knowledge on fundraising from Silicon Valley - from people like Fred Wilson, Naval Ravikant, Josh Kopelman and others -  and included their wisdom in the book. Seth has also raised $100m across a dozen companies over the last twenty years, and I got to learn from him at DJZ.

We also wanted to give entrepreneurs actual tools that they could use immediately. So we created cap table and financial model templates, a legal document explanation pack and a whole host of other items to go along with the book.

Fundraising is a game with very specific rules. The rules can be broken, but if you walk into the process unaware of what the rules are then you are at a huge disadvantage. The Secret of Raising Money changes that.

There’s a huge potential for productized consulting with ebooks, especially when bundled with templates, videos, etc., as you and Seth have done in The Secret of Raising Money. What should other consultants and would-be consultants think about if they’re considering packaging up their knowledge as a product?

Yes - there is huge potential in productizing consulting with information products. It’s never been easier to turn your consulting skillset into a product. In terms of advice - there is so much I don’t know where to begin! 

I’ll focus on one point: Remember that email is the best marketing channel. When it comes time to sell your product (and for many months before), email should be your top priority. There is a huge misconception that getting influencers to tweet  about your product (or post to Facebook) is a sure-fire way to get traffic. There are occasions where it works, but over the past few weeks we’ve learned that conversion rates from Twitter are very hit or miss, and depend on a lot of factors beyond your control. With email, you can communicate with your list repeatedly, and warm them to the idea of your product over a period of time, so when launch arrives, they are more than ready to make the purchase.

What’s the biggest mistake that people make when trying to raise money?

Failure to seek out multiple competing offers. There is a concept in negotiation theory called ‘BATNA’ - Best Alternative to a Negotiated Agreement. The basic gist is that your leverage in any negotiation is a function of the viable alternatives you have available. This applies heavily to fundraising.  The leverage you have with any investor is very much defined by how much other investor interest you have. As a result, you must seek out multiple term sheets, not just one. And the way to do this is to condense your fundraising into a short time window, and approach many investors, all at the same time.

There’s a learning/cumulative part of writing. What’s something that you and Seth learned while writing the book?

The hardest part of writing is finding your flow. Often I would write a sentence, then rewrite it, rewrite it again, etc. This is the wrong way to go about it. The way around this is to  “Lower your standards and keep going.” (credit Sandra Tsing Loh). In other words: just write, even if the stuff that comes out is subpar. Suddenly you’ll find you’ve written a few pages. And only then do you go back and revise it. Much like product development, writing is very much an iterative process. The first version sucks. The way you get to something great is by going back over your work again and again.

The Secret of Raising Money is available in multiple tiers. Could you explain the different options?

There are three bundles - The Elite Bundle, The Bootstrapping Bundle and the book.

The Elite Bundle has everything you need for a successful fundraise: 

  • The book (The Secret of Raising Money)
  • 7 exclusive new video interviews with world- leading VC’s and entrepreneurs
  • 7 video transcripts
  • 6 exclusive written interviews
  • Cap table template
  • Cap table explanation pack
  • Four financial model templates (Saas, mobile, media, transaction revenue -  but fully customizable for any business)
  • Budget template
  • 16 beautiful pitch deck templates (keynote and powerpoint)
  • Legal document explanation pack
  • Fundraising cheat sheet for team

The Bootstrapping Bundle has the book plus a few other resources:

  • The book (The Secret of Raising Money)
  • 1 exclusive video interview with Josh Kopleman, Founder of first round capital
  • 6 exclusive written interviews
  • Cap table template
  • Cap table explanation pack
  • Budget template
  • 16 beautiful pitch deck templates (keynote and powerpoint)

And then if you just want the book, you can get that too (+ a little extra):

  • The book (The Secret of Raising Money)
  • 6 exclusive written interviews

Now that this collected wisdom is available, are you going to have to develop new money raising tactics in the future, or is there a benefit to widely sharing trade secrets?

No - we we won’t have to develop new tactics. Much of what we teach in the book are fundamental principles. For example - social proof. Social proof is the idea that investors are more likely to invest in a company if others are already invested, or at least showing interest. It’s the herd instinct. But this phenomenon isn’t just limited to investors, it’s an inescapable part of human psychology. People are more compelled to do something if others are already doing it. And what’s more, all investors are profoundly aware of this phenomenon. But they still can’t avoid being compelled by it.

Are you offering any sort of launch discount?

Yes! You guys at Gumroad (especially Ryan, Sahil, Jessica, Travis and Tuhin) have been so incredible in helping us through every step of this process. We are constantly blown away by how helpful you are. So we wanted to do a special Gumroad discount.

Get 20% off all bundles of The Secret of Raising Money on Wednesday, March 19th. Use the code “Gumroad”.

Gumroad Trip: Mirthful Cynicism and Mario DiGiorgio

Travis Nichols on March 13th, 2014

I first met Mario DiGiorgio briefly several years ago when we were both selling shirts at a boutique in Austin. I had one design that was moderately interesting, and he had what could have been a whole store’s worth of clever, hilarious stuff. I also saw him do stand-up a couple times. So when I was perusing the hallowed halls of Gumroad’s archives while planning the cross-country Gumroad Trip, I was excited to find Mario’s book, A Cynic’s Guide to a Rich and Full Life, for sale via Last Gasp's Gumroad account.


Mario was only vaguely aware that an ebook version of his Chicken Soup for the Soul / Life’s Little Instruction Book-esque parodic tome was being sold online (how’s that for passive income?). He agreed to meet up and shoot a video in exchange for a ride to the airport. Good trade.

So what you’ll see here is a glimpse of some of the dry, twisted stuff you’ll find in Mario’s book. Mario also reads some of the book’s introduction, which includes a great line that kind of sums it all up:

"Anyone can hold a door open for a stranger. However, it takes a rare and special breed to trip them in the process."

Find The Cynic’s Guide and other books from Last Gasp at

Find Mario at


Previous stops on the Trip:

Ben Johnson, musician - Austin, TX
Yale Stewart, comic book artist - St. Louis, MO
The Sun Bros., comics duo - Chicago, IL
John Staskevich and Kevin Holland of NTHSynth - Columbus, OH
Brad Guigar, artist and illustrator - Philadelphia, PA
Lisa Yen, designer - Queens, NY

Quick Tip: Sell More by Giving More.

Jessica Jalsevac on March 7th, 2014

It may seem counter-intuitive, but sometimes the best way to sell your products is to give them away.

I recently took a closer look at Kyle T Webster’s stats for an in-depth case study (more on that soon!). Kyle has done a phenomenal number of sales of his custom photoshop brushes over the past several months.

A major pillar of his sales strategy is to give away some of his products. He does this in two ways:

Pay-what-you-want products:

Kyle has three small pay what you want products that give potential customers a sampling of his brushes. These products have generated tons of views and downloads since he started doing them in October. Here are the stats to date:

  • 57,000+ product views
  • 12,000+ downloads
  • 39% conversion

Not only did tens of thousands of people view and download the products, but many also decided to pay him for it, resulting in over $3200 in revenue! 

To download the free files, each of the 12,000+ customers entered their email address, allowing Kyle to add them to his mailing list and contact them about future product releases, pre-orders, sales, etc.

 Limited giveaways of regular products:

 Kyle also periodically offers a download of one of his regular products to three random Tumblr users if they reblog certain posts about his brush sets. He notes, “when the timing is right, these posts can lead to thousands of reblogs in a span of only a few hours.” This is a great way to get exposure to other people’s audiences.


Won’t this hurt my profits?

Consider all the famous chefs who post their recipes - their trade secrets - online, or the bands that release several singles before their album launches, or how you can practically eat a meal from all the samples at Costco.

Its all the same idea. Allow the world to experience your work and it will thrive.

The Harvard Business Review recently did a blog post on generosity as a growth strategy. In it the author talks about how “giving [customers] a little taste of something great will have [them] coming back for a lot more - at full price.”

There are three important outcomes of sharing your work freely:

  • You build trust and credibility with your audience by showing them what you’re about and the quality of your work.
  • You make your fans feel great and generate lots of goodwill. This, in turn, makes people want to talk about you and your work.
  • You cultivate long-term relationships with your customers. If you build trust and make your fans feel great, they’ll be more likely to support your future project

A few weeks ago we talked about using some sort of bait, or an “ethical bribe" to entice people to sign up for your mailing list. I hope this has expanded on that concept and got you thinking about other ways you can get your products out into the world.

Building Profitable Audiences with Nathan Barry

Travis Nichols on February 26th, 2014

We’re not afraid to say that our first Gumroad Creators Studio event was a success. Nathan Barry spoke on building profitable audiences and what he’s learned along the way. His presentation was followed by a chat with our own Ryan Delk and questions from the audience. There was delicious food provided by Chef Luis Estrada and a headshot studio courtesy of our new friends at 8:45a. The PARISOMA team was fantastic, and we look forward to our events with them in the future.

We’re also not afraid to say that we filmed the HECK out of the event. Caleb Wojcik would have nodded in silent approval at the sight of it all. Then… the unthinkable happened. The cameras and memory cards were stolen. Footage LOST.

However, a couple of the audio sources evaded the thief’s nefarious grasp, so they’ve been put together with the slides that Nathan used in his presentation. So please enjoy! Also, we’d like to think that somewhere, the perp is watching and re-watching the stolen footage and turning his life around. When you’re ready, friend, we’ll be happy to welcome you and your multi-tiered redemption memoir to Gumroad.

Shouts out to our friends at PARISOMA, 8:45a, and Chef Luis Estrada.

Nathan’s Photoshop for Interface Design is available now. Cut the fluff and learn skills you’ll use every day.

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