What a Mysterious $10 Bill Taught Me About Business and Life

Jessica Jalsevac on May 9th, 2014

This week we’re thrilled to feature a guest post by writer Jeff Goins. Jeff is the author of several books, including ”The Writer’s Manifesto,” “Wrecked,” and “The In-Between." He has also built his blog into a powerhouse with more than 200,0000 monthly readers.

In this post, Jeff talks about an important but underused principle that has driven his business to be so successful. Here’s Jeff. 



My last year in college, I had a couple friends visit me for the weekend. That weekend, I was playing John Proctor in the school play The Crucible, which is a retelling of the Salem Witch Trials.

Since they were driving twelve hours both ways, I wanted to be able to take my friends out for coffee or something, to show my appreciation for their sacrifice. But being a broke college student, I was less than eager to get rid of the extra cash weighing me down (meaning, I didn’t have any).

I had exactly $0 to my name.

The first night that my friends were in town, a student organization invited us out for pizza after the show. Which meant a free meal. Score. One meal down, five more to go.

Later that evening, as I was getting ready to go onstage, someone told me I had a note out on the announcement board out in the hallway. Leaving the dressing room to investigate, I found an envelope marked “Jeff” pinned to the corkboard.

In the envelope, between to blank index cards, was a ten-dollar bill. No note. No explanation. Nothing. It was a miracle.

That evening, I took my visiting friends out for coffee. Another friend picked up the bill, paid it, and left the restaurant before we even realized what had happened. I couldn’t believe it. Yet again, we were taken care of.

So I did the only sane thing I could think of: I left a ten-dollar tip.

Giving Is the Best Strategy for Getting

As we were leaving, I threw my little miracle bill — all the money I had at the time —on the table, remembering something my dad has told me my whole life: what goes around comes around.

It really is true.

The rest of the weekend was filled with moments like that — random invitations to potluck dinners and opportunities to attend organizational lunches along with random acts of kindness scattered throughout the day.

It all happened without having to ask for any of it. The same type of event has repeated itself in my life countless times. Little did I know as a Spanish major in college, how important this lesson would be in my life as an online entrepreneur.

But after starting a business to help other writers and communicators get the attention their message deserves, I’ve come to rely on one single strategy for success.

This simple trick will take you further in your business, in your dream, in whatever venture you’re trying to launch, than anything else. What is it?

Help people.

Okay, okay. You’ve heard this before. It’s a platitude, right? It’s been overstated, I know. But here’s the thing: some platitudes are true. This one certainly is. And for the longest time, I lived my life based on a scarcity mentality, thinking that the pie was smaller than I realized. It’s not.

The opportunities to make a difference and a living are more than you could ever imagine. How do I know this? Because I witnessed it first-hand, seeing it tacked to a corkboard at my college theater so many years ago and continue to see it every day of my life when I open my laptop each morning.

So what does it take to practically get there? And how did I apply this experience to launching an online business that ultimately led to both my wife and I quitting our jobs to chase a dream?

Good question.

How to Build a Generosity Business

Here are the steps to building what I call a generosity business, in which you really do get what comes around:

1. Follow the Golden Rule.

Do unto others as you would have them do unto you. The bottom line: treat people right, and you will make a name for yourself. Show up on time, do what you say, and your brand will grow.

Why does this work? Because, surprisingly and sadly, most people don’t do this. So this is an easy way to get free publicity — do the right thing, no matter the personal cost to you.

It’s not always easy, but it’s right. And in the end, this is a way better investment than any amount of advertising.

2. Give without expectation.

Connect with people, truly care about them, and do everything you can to help them get where they want to be.

Do not ask or expect anything in return for this. Do it for the sheer pleasure of helping people. This, too, works. It’s also a disarming way to network your way to success. When everyone is trying to get people to do things for them, you can be different.

You have heard “it’s not who you know, but who knows you” but that’s not true. It’s not who you know, but who you help. The way to make a name for yourself, to attract more clients or customers than you know what to do with is to be more generous than others. This will get people talking. Trust me.

Remember that ten-dollar bill that changed my life? Well, years after the fact, I shared that story on my blog, and my friend Sarah finally came clean with me, confessing that she was the one who put it there.

I will never stop telling that story and will never stop giving Sarah the credit for how one small action made an impact on me, and therefore, thousands of other people.

3. Share what you know.

How do you get people to pay attention to you, to consider you an expert? Do you go back to school, read a lot of books, attend a lot of conferences? No. You do none of that.

Those are all good things and you’re welcome to do them, btu they will not qualify you to share your story, to build your product, to give your offering to the world. The only person who can give you permission to do that is you.

So how do you get the confidence to start? You have to believe what you have to share is worth people’s money, that you are worth listening to and your product is good enough to charge for.

And how do you get to that point? You begin by being generous, by sharing what you already know, then see what resonates.

This was what Nathan Barry did when he started his blog: he shared what he knew. And what did he, a young designer who had worked for a startup, know? Well, he knew about design. So that’s what he talked about. And when people started to show up to hear what he had to say, he knew he was on to something.

In a way, building the business was the easy part. The hard part was figuring out what to say and who would listen. Once you have people’s attention and are generous enough to get them to trust you, monetizing isn’t difficult.

So before you start thinking about how to charge for your expertise, you need to instead seek out ways to help people now:

  • Call up an old friend and see if you can solve their problems.

  • Write a blog post about your biggest struggle and invite others to do the same. See if you have the solution to some of their problems.

  • Put your stuff out there, see what connects, and go from there.

Then and only then, when you have people showing up, can you start charging. At this point, you have done all the hard work. It’s just a matter of letting them pay you.

And pay you they will. The law of reciprocity will take effect. What goes around will come back around to you, and those who have received from you will be glad to give you money.

This is the paradox of generosity: you always end up getting more when you give.

Jeff Goins is a writer who lives in Nashville. To get his free, three-part series on building an audience, check out Goinswriter.com/gumroad.

The Afterlife with Nathan Barry

Travis Nichols on May 1st, 2014

A wise man once said, “One thing leads to another.”

When thinking about your second, third, or fourth project, you don’t have to start from scratch. What can you build on from your last product? It just might have a life beyond your original intention.

For example, Nathan Barry went from building apps to teaching/writing about designing apps to writing about writing and publishing to teaching about that whole process/marketing in blog posts, speaking engagements, etc.

Nathan spent a couple days with us a while back, and one afternoon we went to our favorite coffee house, Front, to talk about The Afterlife of a product. How something you do can become another thing you do.

It was loud. There were multiple construction sites on the block, the freeway was buzzing, the trucks were roaring by, the auto shop across the street was in full swing, the gossipers were gossiping, and the steam was gushing from the espresso machines. But the coffee was great and the words were flowing, and there was something about all of that commotion that just… made sense.

"I found that I was getting more and more questions about how to sell books, and how to make money from teaching than I was actually getting about design. So my third book, called Authority, was actually on how to write books and sell them and make a living from that. And that’s something I wouldn’t have thought, early on, that I could write about, or was even interested in, but because of the response from the first two books, and because of the things I learned, it just opened up so many new opportunities.”

So what’s it going to be? Remember, when you aren’t starting over with a product, you don’t have to start over with your audience.

Gumroad Trip: Jacob Eiting’s View / The Roundup

Travis Nichols on April 24th, 2014

Jacob Eiting wants you to start flying planes.

He’s one of the youngest airplane owners he knows and is likely the youngest owner at Gnoss Field, where he keeps his 1965 Piper Cherokee. “Something a lot of people don’t realize is that airplanes are expensive but not unattainable. I’m 27 years old and I bought an airplane two years ago. I didn’t win the lottery or anything. This airplane cost $29,500 to buy. That’s about the same price as some of my friends’ cars.”


He went on to explain that the US is one of the best countries to own and fly planes in, but we’re at risk of losing that. “The infrastructure relies on having a lot of people. As the number goes down, it’s more expensive to maintain. More airports shut down, which then degrades the infrastructure, which then makes people not want to fly as much. If we don’t maintain what we have, we’re going to lose it, and it’s never going to come back.”

Jacob is a developer who makes software for pilots and flying enthusiasts. After making iOS and Android apps, he’s found the most success with a Windows application. FSXFlight allows iPad aviation apps like ForeFlight and WingX to be used with Microsoft Flight Simulator. This creates a virtual cockpit and works as a home training tool with added realism to the simulation.


Jacob also sells a cable that allows pilots to record cockpit audio into a smartphone. The best use is when it accompanies his iOS app, Black Box. The audio from the in-flight portion of the following video was recorded via the cable and the voice memo app on my iPhone.

"The thing I love most about flying is the absolute control-slash-freedom you get from flying in the air. If you have the inclination to be I want to go over here today, for the most part you just jump in and go, or I want to fly over this thing, or wouldn’t this be cool from the air? You just can go up there, and once you’re in the air, it’s just total freedom. As long as you end up on a runway at the end of it, it’s usually a good day.”

The explorative soundtrack to this video comes courtesy of Megan D. Harrigan.


And with that, the Gumroad Trip ends. Brooklyn, NY to San Francisco, CA. What can we take from all of it? First, we’ve got an amazing group of creators using Gumroad. Second, I’m ready to hit the road again and meet more of you. Let’s take a look back from the beginning.

Lisa Yen showed us that where there’s a need, it can be filled. In a small, urban environment, she craved a touch of nature. Influenced by her green-thumbed father, she creates tiny forests and jungles that can live in most cramped city apartments.

Brad Guigar plays the long game. He built his comics career from the ground up, and has literally written the book - two, even - on the art and business of webcomics. What can you teach others?

NTHSynth's John Staskevich and Kevin Holland show us the power of collaboration and challenging each other. Sure, we could make a synth with all of the buttons in the world, but what can we do with ONE? They also provide a lesson on teaming up with people whose skills can complement your own. I still have lots of fun with our office’s Luminth.

The Sun Bros. are all about hustling. Hard. They’ve turned a lifelong love of comics, games, and movies into a business. They hit the convention circuit with ferocity and actively seek out speaking and panel opportunities.

Yale Stewart's story is all about getting a toe in the door, then kicking it open. He was able to pivot from something widely appealing that he couldn't sell (a fan comic about the Justice League as 3rd graders) into something personal that he could sell (a creator-owned graphic novel). He’s now working on books for major publishers. He’s also used his powers for good to raise money for disaster relief.

Ben Johnson is all about going for it. As college came to a close, he realized that he needed to give it his all. Now. Album, album, project, book, album. His devotion is inspiring.

Mario DiGiorgio went from highwayman stand-up comedian to t-shirt mogul and writer. After close to nine years on the road, he changed direction slightly and is making audiences laugh in even bigger ways.

Jacob Eiting decided to see the world from a different point of view. He, and all of the creators in this series, refuse to accept assumed barriers.

You can fly a plane. You can run a thriving business out of a corner of a room. You can make weird instruments with your friends. You can write and draw your own books. You can go to Alaska and write songs. You can make a movie. You can create, share, and inspire. How can we help?

See you on the road.

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 https://gumroad.com/l/roadtrip. The cutoff is April 20th! And to receive monthly stock photos, go to join.deathtothestockphoto.com.

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 Femgineer.com 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 Fizzle.co, 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 calebwojcik.com.

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 support@gumroad.com, 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”.

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