Pies, Ideas & Insecurities

Pies, Ideas & Insecurities

My first business was a gourmet dessert catering company in New York. We hand crafted miniature pies from scratch for weddings and events.

We went on to get featured on TheKnot, and even supplied mini-pies for the wrap party of the IFC cult tv series Whisker Wars.

Note from Chase: I know what you’re thinking, “pies!?” Just give it a bit. Dan’s about to tell the story of how he made his thing recently. It’s a great story (and a tool you need to know about).

Though I don’t make pies anymore, I still moonlight as a private chef sometimes. Last summer I wanted customers to be able to book me online using a credit card, so I signed up for a Gumroad account (it’s free).

I immediately fell in love. Every time I booked a gig my customers commented on how beautiful and easy to use my payment system was.

Selling with Gumroad inspired me. It made me want to create a product of some kind. The problem was, I wasn’t in the mood to come up with the next best internet thing. I didn’t have an idea.

Finding An Idea

I had learned a lot of marketing and web-design skills after quitting the pie business to co-found a social media management company. We had clients like PsychCentral and PBS, and managed over sixty blogs with combined traffic of 600,000+ uniques/month.

It’s always smarter, cheaper, and faster to use the skills you already have to create a product. So, instead of racking my brain for business ideas, I made a list of people I knew who were already creating interesting and meaningful things. On the list were people I respected, admired, and would enjoy helping, even if it was for free.

Over the course of several days and a bunch of emails, I connected with a talented software developer named Fred Bliss. The conversation began with zero expectation on my part; I simply wanted to help him in any way I could.

Two hours in, serendipity struck.

Fred mentioned offhand that he’d sold over three-hundred copies of a WordPress plugin prototype he’d built earlier in the year, but for various reasons he had to put the project on hold, and was hoping to revive it somehow.

When Fred told me what he’d designed the plugin to do, I literally choked on my coffee. Through a fascinating twist of fate, Fred’s prototype was a sales tool that integrated Gumroad with WordPress.

Gumroad is already easy to use; this plugin just made it even easier for WordPress users to sell stuff directly on their websites, and even integrated Gumroad with popular email marketing services like AWeber and MailChimp.

Fred asked me if I’d help him re-launch and market the plugin for a share in the profits. After my emphatic ‘yes’, it occurred to me that by simply listening and trying to be helpful, an online product had all but fallen into my lap.

That conversation was four months ago.

Today, I’m thrilled and honored to be revealing GumPress to the world for the first time here on The Sparkline.

I’m also going to break down how we built it, why we decided to market it the way we did, how we priced it, and why Fred ended up having to redesign a critical part of the plugin from the bottom up.

And since this is my first online product, I’m also going to reveal some very personal fears and insecurities I’ve had along the way.

Fred took the lead on engineering the plugin, so I took the lead on positioning and marketing the product. Before I made even one website mockup or designed the logo, I started writing copy.

The Message & The Theme

I’ve learned that the most important part of marketing anything is the messaging. Even if you build the most useful thing ever created, nobody will care unless you’ve crafted a message that resonates with the right people. Chase speaks about the power of good messaging in his Fizzle course: Essentials of Website Design for Business Builders (alone worth the price of entry).

The first step to finding a message that resonates with the right people is to clearly define the problem that your product solves.

The problem we’re solving is as follows:

Building and selling things on a website is way too complicated. You shouldn’t have to hack code together or be forced to use a bloated & complicated piece of software to make sales happen on your website.

Technical barriers force creatives like us to spend countless hours & many hundreds — if not thousands of dollars figuring out how to get our digital products and services for sale so we can grow our businesses.

After writing about this problem in my journal at great lengths I found a messaging theme that became the foundation of our entire marketing strategy.

A messaging theme should be a statement that represents the fundamental usefulness of your product. It’s a starting point upon which you can build out a variety of benefit-driven selling points.

Our messaging theme became:

“Spend more time getting customers and less time messing with technical stuff that doesn’t matter.”

Now that I’d constructed a messaging theme, I was able to write a bunch of headlines & subheadlines that stuck to the theme. These headlines and subheads became the building blocks of the marketing copy you see on our website today.

It was important for me to check in with Fred at this point to make sure that the tool we’d be selling solved the problems I’d outlined in a way that was consistent with our messaging.

As I’d predicted, the tool fit the bill spot on – except for one hiccup. To use our plugin on your website, you had to first go through an authorization process that was a pain in the ass and took too long.

Fred made the call right away to put in a bunch of extra work to make the authorization process as simple and easy for you as possible. After all, spending time authorizing an app is way less important than making your first sale on your website. We wanted to provide a tool that would get you selling on your site in less than 5 minutes.

With Fred busy on the re-engineering, I dove into creating the website that we’d be using to sell GumPress.

Predictably, the first iteration of my site design sucked; the color scheme was seizure inducing. Thanks to a friendly slap in the ego from Fred, I swallowed my pride and started again from scratch.

Since the messaging was crystal clear, the redesign was relatively painless and the second iteration became the landing page you see today.

Now that we had a landing page, our pricing was the final marketing decision we had to tackle.


Back in my pie making days, we tested many different flavors and sizes. I learned early on that when we offered three different sizes at different price points we’d sell out twice as fast and earn at least twice as much money than when we just offered one size at one price.

I didn’t realize it at the time, but I’d discovered the power of tiered pricing.

Nathan Barry, who is a power seller on Gumroad and a frequent contributor to Fizzle has amazing results with applying tiered pricing to his digital products.

As such, we knew right away that we needed to offer three distinct packages at different value-based price points that would appeal to different types of users.

We first decided the three tiers would be differentiated from one another based on their functionality.

Our base tier, which we named the “bootstrapper” package, empowers anybody with a WordPress website to start selling their Gumroad products, services, and subscriptions on their site with a custom ‘buy now’ button — all within five minutes and without having to write a single line of code.

Our middle tier, the “business builder” package, is modeled after the original prototype that sold over three-hundred copies; as such, we wanted it to be our flagship tier, so we packed it with value. It has all the functionality of the “bootstrapper” package, but additionally, it integrates your Gumroad account with one of your favorite email marketing services like AWeber, MailChimp, or GetResponse, so you can grow your business and market to your customers like a pro.

Our advanced tier, the “power user” pack, gives consultants, developers, and power users access to all email marketing service integration modules, a membership site add-on that integrates Gumroad with WishList Member, advanced integration with InfusionSoft, and lifetime plugin updates.

Once we were settled on the package configurations, we needed to finalize our pricing.

We used a combination of ‘value-based’ pricing and what I call ‘comp-pricing’.

Value-based pricing is a way of determining your product’s price based on the value it adds to your customer’s life. It’s a pricing method that results in fair and equitable exchange of value for both the seller and the purchaser.

Some questions we used to influence our value-based analysis were as follows:

  1. How much would somebody have to pay for a custom solution that does the same thing?
  2. How many hours would it take for somebody to learn all the skills necessary to hack together their own solution?
  3. How many sales, customers, and opportunities is somebody giving up by not having access to a tool like this?
  4. On the spectrum of business priorities, how important is it to somebody to be able to sell stuff on their website?

The answers to these questions helped reinforce the immense value we were hoping to add to our customers’ lives.

We then compared our value-based pricing with the prices of comparable products already on the market. I call this method of pricing ‘comp-pricing’. Value-based pricing gives you a ballpark figure, but comp-pricing can help you determine whether or not your value-based pricing is realistic in the marketplace.

After doing some comp research and consulting with some startup friends of mine, I was shocked to find that we’d undervalued our product by almost fifty-percent. In retrospect, this was directly related to the fact that Fred and I both have chronically undervalued our work for most of our careers. This was a monumental learning experience for us.

If you undervalue the work you do, you will undervalue the products you create.

With a renewed sense of self-worth, we decided to double the prices we’d initially come up with. As I write about this now, I realize how painful it would have been to learn that we were only earning half the value we’d created.

Reaching Out

Once we settled on pricing, it was time for me to start reaching out to people I knew who led communities of business builders.

I reached out to Chase, who is a very talented designer and human that I’ve admired for some time. I ended up at a Fizzle cocktail hour a couple weeks later meeting all the guys face to face for the first time in San Francisco.

We spoke about the plugin over tasty cocktails. Chase expressed how much he loved Gumroad and was already planning on doing Gumroad related things on the newly launched Sparkline in the coming months.

I was thrilled when he asked me if I’d be willing to contribute something to the blog. Once again, by simply listening and trying to be helpful, an amazing new relationship all but fell in my lap.

Note from Chase: To be fair, you were wearing a very good smelling cologne and drinking in a cilantro infused gin. I was smitten, Dan.

This experience, and countless others reinforce that the fastest way to make a lasting impression on somebody is to genuinely care about who they are, what they do every day, and who they care about. It’s how I ended up writing to you today, and its how I’ve made a bunch of new and exciting relationships with other communities of business builders as well.

So far I’ve taken you through how I stumbled upon the product idea, specced it out with my talented co-founder Fred, iterated on the design, developed a marketing message, crafted a three-tier pricing structure, and made our first connections.

As promised, I’ll now share the things I wake up thinking about every single day, including the deepest fears and insecurities I’ve had throughout this project.

Fear, Resistance & Insecurity

Building and launching a product is like voluntarily signing up for manic depression. Chances are you’re emotionally attached to the work, and you may find yourself tap-dancing on a roller-coaster of fear as launch day approaches.

The fear of failure becomes increasingly intense the more you have on the line.

Early on, my co-founder Fred imparted to me that his ten year old son had been recently diagnosed with Cystic Fibrosis. CF is a heartbreaking diagnosis, and Fred had been struggling with the longstanding guilt of knowing he’d probably outlive his first little boy.

He also felt stuck in the grind of trading hours for dollars as a freelance developer, and as healthcare-related expenses and challenges piled up he became increasingly overwhelmed.

We embarked on this speculative journey with the singular hope that we could revive a product that proved itself in the marketplace less than a year ago.

We’ve had no money to pay ourselves, but even though together we’ve put over 1,000 man-hours into the project, we’ve actually spent less than $50 total so far.

We pulled out all the stops, wrung every last drop of skill out of our minds, and battled countless nights of depression and fear together on Skype to build this thing.

Still, I wake up every day knowing that there’s no guarantee people will find, try and buy GumPress, and that Fred may never recoup all the time he put into building GumPress instead of finding new freelance gigs to feed his family. What if I led him astray with my Internet dreams?

I have other, more selfish insecurities as well, like:

  • What if I botched the pricing and it’s too high or low?
  • What if I completely misjudged the usefulness of this tool?
  • What if people hate my web design, does that mean I’m a hack?
  • What if GumPress flops? Will all the people I respect write me off as a phony?
  • What if GumPress explodes? Will I be able to handle it or will I totally blow it?

Although these fears are intense for me sometimes, I’ve found great strength, courage, and resilience in myself through many adversities in my life. I’m not as attached to my fears anymore, which is why I can be vulnerable about them with you.

To conclude, I sincerely hope the stories, insights, and tips I’ve just shared with you will help you in some way — perhaps if only to give you a dose of courage in your pursuit of creative freedom and a self-sustaining business.

If we could get to today with almost no resources, some heavy emotional obstacles, and nothing to sustain us but the dream of having something of our own to share with the world, then so can you.

We’ve even built a tool that can help you get there. You can find it here:

GumPress, the easiest way to sell on WordPress »

It’s always smarter, cheaper, and faster to use the skills you already have to create a product.
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Photo via Sue Langford
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  • Dan Gamito

    Thrilled to have been able to contribute this!

  • Faith Watson

    That was a fantastic story, Dan! I love reading a blog post in an honest-to-goodness narrative format with authentic human condition included. Thank you! In our arena, many of us are stuck too long alone in front of our screens, want for the smell of a good cologne or a mini-pie. It was also a great way for me to learn a lot, and so I’ll be checking out your Gumpress since I’m long overdue for that sort of thing and I hate messing with technical stuff. I am for you 100%!

    • Dan Gamito

      Faith, you made me blush. So happy this was useful to you :-)

  • Bree Brouwer

    Dan, thanks for this honest story. It’s making me want to try Gumroad and GumPress at some point in the future. You know, when I actually have a product up to sell. :)

    Also, I don’t blame Chase.

    • http://getgumpress.com Dan Gamito

      Haha you don’t blame Chase for being smitten? :-)

      Email me any time at dan AT getgumpress.com , maybe we can get you started sooner than later!

      • Bree Brouwer

        Yeah, I mean, who can refuse a guy with a cilantro-infused gin.

        I might do that here, if only to say hi and learn more about the product!

  • http://jackiejohnstone.com/ Jackie Johnstone

    LOVED this piece Dan! Thank you so much for your complete transparency and honesty, it’s so refreshing :) I’m in love with Gumroad and had just been linking off to it from my site because I couldn’t be bothered to try and figure out all the tech stuff to get the overlay pop-up. Totally buying Gumpress! (And thanks Chase et al for bringing this great story & product to light!)

    • Dan Gamito

      Thank you so much Jackie! Excited that it’s a good fit for you.

  • Jamie Logie

    Thank you for the article. I’ve just got up and running and used gumroad for my first product. Im interested to see how much else I can create using it

    • Dan Gamito

      Gumroad is an amazing service run by an even more amazing team. We are thrilled to be working on their platform.

  • Dina Lynch Eisenberg

    Dan, I’m a real toolhead so first, thanks for GumPress. It’ll make a world of difference to my clients who have content to sell but aren’t all that techy. Thanks as well for sharing your story. You know, there’s be less misery, I think, if people did more research. I find the more research, the better aligned with needs, the more my confidence gets rock solid about whatever I’m offering. I know, not sexy, but the results sure are.

    • Dan Gamito

      I love it Dina! You’re right, research is key (and sexy :-) Shoot me an email at dan AT getgumpress.com , I’d love to support you and your clients in any way I can. Thanks for reading!

  • http://restartyourstyle.com/ Robert van Tongeren

    Nice story Dan. Clearly illustrates the importance of building relationships.

    One question though, at the start of your article, you mentioned you sold your chef services is through Gumroad… But I thought Gumroad was only for selling products. How did you set that up?

    • Dan Gamito

      Thanks Robert! I set up private parties and cooking demos as Gumroad products (for example, “Cooking demo for 12″, then sent my clients the links to book up front. Same model would work great for coaching services etc, make sense?

      • http://restartyourstyle.com/ Robert van Tongeren

        Not really :p I’m a bit of a newb when it comes to selling stuff.

        Could you be slightly more detailed, and explain how you would translate it to a coaching service?

        I’d be quite grateful, because I’ve been trying to think of a good system for this. And when i read how much your clients loved it, you instantly piqued my interest.

        • Dan Gamito

          No problem. Let’s just say you’re selling monthly hour-long coaching calls. You could set up a Gumroad subscription called “Monthly Coaching Call With Robert”, price it at $xxx, and then put that Gumroad link on a sales page or email it to your subscribers, and voila you’ve got a way for clients to book your services on a monthly recurring basis. Email me at dan AT getgumpress dot com to see if we can’t find a solution for your specific needs!

          • http://restartyourstyle.com/ Robert van Tongeren

            Ok, makes sense, but what if I just want to sell a single coaching call at a time?

            I assume when someone booked you for a private party, they only booked you for one evening, right? Not on a monthly basis.

            Do I then choose “Add a product”? Because then I’m asked to upload a file.

            I guess my question is, what file do you send them through Gumroad, and how would you proceed to set up a meeting?

            (I don’t have any specific needs quite yet, but I want to set something like this up in the future. I’m keeping this in the comments for now, because I think other readers might want to know. Thanks so much for helping though.)

          • Dan Gamito

            Exactly-for my cooking gigs I created a Gumroad product & uploaded a custom PDF with menu items they could choose from, etc. I also would upload a PDF they could use as an event ticket, etc. You could send them a PDF with a link to an intake form on it. If you are worried about overbooking, you can limit sales to a certain number (for example, if you can only handle 5 coaching calls per week, then limit the Gumroad product quantity to 5, and reset it as your availability increases.)

          • http://restartyourstyle.com/ Robert van Tongeren

            Thanks, man That really helps a lot.

  • http://www.IncombyNumbers.com Julia

    Incredible story Dan! Thanks for sharing your experience. Now if you’ll excuse me, I am going to go copy your pricing research strategy! :)

    • Dan Gamito

      Love it Julia, hope you uncover some hidden pricing gems! Maybe it’s something we can discuss on the 30th at your mastermind :-)

  • Teresa Capaldo

    Hey Dan,

    Great post! Wonderful story with lots of valuable take-a-ways~

    I’m in process of redoing my site, maybe switching domains. I have a few questions:

    1. If I purchase today, can I hold off on use of plugin till my site is situated? (might be a few weeks tops) I assume the plugin cannot be transferred when a site is redone.

    2. I’m confused as to where the money goes. Does the ‘buy now’ button link to our designated bank acct. or ?

    3. Are there any other service fees paid to gum road with each purchase transaction?

    Last and just FYI, I subscribed twice and never received the Free guide. I even checked spam.

    I’m excited to get going with this!

    Thanks much and best to you! :)

    • Dan Gamito

      Hey T, thanks so much for reading. 1. get it today, get 12 months of updates and multiple site usage so you’ll totally be good to go! 2. money goes to Gumroad, gets paid out from Gumroad to whatever account you set up via direct deposit (SUPER convenient) 3. Gumroad is free to set up and they serve all your files for you, they take a very reasonable 5%+25 cents/transaction (no setup fees, no monthly fees). 4. I’ll email you your free guide! Check the forum for an exclusive Fizzle-only discount, only 12 hours left, won’t be discounted again :-)

      • Teresa Capaldo

        Wonderful! You are thorough ;)

        Thanks, Dan.

  • http://www.i7marketing.com Sean Gallahar

    Great post Dan. Thanks for sharing the story of your new product, which sounds awesome by the way.

    • Dan Gamito

      Thanks Sean! Appreciate the shoutout on Twitter.

  • http://kimanziconstable.com/ kimanzi constable

    Congrats Dan and great post. We all experience that fear but the why keeps us pushing forward anyways :)

    • Dan Gamito

      Thanks Kimanzi!

  • http://getgumpress.com Dan Gamito

    Thanks for reading Beatrix :-) We haven’t strayed too far from our base functionality, though we do have plans to make Gumroad as accessible to as many platforms as possible.

Up Next:

Are You Making the Most Common Pricing Mistake?

In my hurry to launch my first product, an eBook called The App Design Handbook, I almost made a mistake that would have cost me over $10,000, a mistake that I see being made with products all around the web. Luckily for me, a few people were kind enough to lead by example and show how important it was to fix this.

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