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Abstract

ing in my stomach. I didn’t want to build something that people wouldn’t need. We’d never be able to get anyone to pay for it. I wanted to build a tool people would rely upon. I decided it was a better idea to focus on professional authors.I drove to Chicago that weekend to stay with some friends that I knew would help me figure out what to do next. We took a lot of long walks, and sat around on their porch late at night, working through different scenarios. At some point, we started brainstorming another startup idea. It was a service that would let authors test their the shelf-appeal of their books. Users would sign up for a weekly email of upcoming books in the categories they’re interested in, and authors would pay to have their books be included in that list. You could see the first chapter of the book, and give the author feedback. Authors would get analytics, even the ability to A/B test their titles and openings.Christine (one of my Chicago friends) and I stayed up until 3am researching and writing down our hypotheses. I went from the lowest despair to the highest confidence in just a weekend. I was sure this was a million dollar idea. Since this idea was just as much Christine’s as it was mine, and we had complementary skill sets, I knew I wanted to work on this idea with her. I would have to call it quits with Brighten.<h2 id="2642">Startup 2: Pencrafted</h2>Christine and I decided to name our new venture Pencrafted. We talked to authors, all of whom assured us that they would not only use but pay for this service, assuming we could deliver on our promise of actionable feedback and metrics on their books. Everything seemed perfect with this idea, all we were missing was a programmer to join the founding team. I was reluctant to go with the guy I worked with on Brighten because, although he was a great programmer, he wasn’t excited about applying to TechStars or Y-Combinator and moving across the country.Turns out, it’s incredibly difficult to find a tech-cofounder. You need to know the person before you start a startup together. Since you don’t have experience together, it’s impossible for them to fully trust your idea and your ability to build a company. It might look interesting, and it might be fun to work on for a bit, but to start a company you have to sacrifice a lot, and it’s a big risk. I don’t blame anyone for not wanting to take those risks. It’s definitely not for everyone.Even though we couldn’t go any further without a programmer, we needed to feel like we were making progress, so we did fake work. We let our minds wander. We had doubts about whether readers would actually want to get a weekly email of upcoming books. We also knew we had a chicken-and-egg problem. Why would authors pay to reach no readers? Why would readers sign up if there were no books? These problems could have been solved, we could have tested our hypotheses, but ins

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tead we let ourselves get distracted by other, seemingly more straightforward ideas.We decided to become a tool that let authors write books. It would organize your work into chapters, and export to ePub, PDF, and you could even order print prototypes. The business model was straightforward. You’d pay to use the software on a per-book basis, and also pay if you wanted to order printed copies. We started talking to on-demand printing companies, and talked to authors who again said they would use it and pay, assuming it was well-designed.Then we realized something that we should have realized from the beginning: there’s not very many authors in the world, and they’re not very rich. Our total addressable market was just not very big. So we thought of different markets we could bring our technology to. One idea was to let schools use our software, and sell the books to kids parents. It seemed funny at first, then we realized how cool of a class assignment that would be for middle and high-school kids: write a novel. I would have loved the opportunity to do that! We started dreaming up a whole curriculum around this idea. It was a huge market (lots of kids in America), and the prices of printing a book seemed to be really low. Blurb sells paperbacks for as low as 4 $a pop. We talked to some principals and teachers, and they were all very enthusiastic about the idea. We talked to some parents and they said they’d definitely want to buy a book their kid wrote.Then we started talking to quick-printers. They couldn’t believe Blurb’s prices (and I still have no idea how they keep it so low. Loss leader?). The best offer we could get was$ 11 a book, which doesn’t include any of the shipping and logistics costs. The margin we thought we could make was shrinking a lot. The more I researched, the more I realized that this startup idea did not have very much to do with creating a writing app. I am a web designer, and I just couldn’t get myself passionate about doing what it takes to start a bricks and mortar book printing company. The deal was sealed for me when we discovered that there were a couple other companies that did the same thing. Their branding made me want to throw up. I don’t know if this is an insecurity of mine, or what, but I just can’t picture myself being the founder of some “Kidz Bookz / Teen Lit” company. I was inspired by the idea of making a tool that professional authors would rely on.Christine had the opposite reaction as I did. She wanted to make it into a non-profit, and was inspired by the idea of innovating educational curriculum. She wants to give kids in need the opportunity to create books, which is very admirable. But I just couldn’t get passionate about it. So we found ourselves with divergent visions. Now, Christine is going to think seriously about starting Pencrafted as a non-profit.I’m not sure what comes next for me.</article></body>

Advice I’d give my younger self

Today I discovered an blog post I wrote about four years ago. It was my senior year at Michigan State, and I had just lost hope in another one of my startup ideas.

It was a sad time for me. In the writing I try to sound optimistic and confident, but deep down I was worried I’d never get it right. In some ways, it’s a cry for help.

I know there are a lot of people who feel like they’re not sure how to level up as a founder / maker. By no means do I have all the answers, but I’ve come a long way. I’d like to help, if I can.

So here is my post — exactly as I wrote it four years ago. I’ve used Medium’s notes feature to mark up my post with advice and comments. If you have any advice, join me and write a couple comments. It might help!

UPDATE 2/13/16 — Medium changed the way that annotations work, and now they’re all private, with no way to make them public. You can still read the post here, exactly as it was written back in 2011, but you can’t see my notes :(

How My Startups Died (R.I.P. Brighten & Pencrafted)

“Our doubts are traitors, and make us lose the good we oft might win, by fearing to attempt” — Shakespeare

Lots of founders kill their startups by failing to pivot. I killed mine by pivoting too much.

This isn’t an easy post for me to write, because it makes me look pretty dumb, and it’s very personal, but it’s a story that needs to be told. I am a senior in college, and in the past year I’ve tried to start two companies. Both of them are now dead. I didn’t take the time to sit back and reflect after I left the first one. I’m telling my story for two reasons. I hope you can learn from it, but I’m also hoping you can teach me something. If you read this, and think of something I could have done better, please leave a comment and help me learn from my experience. I’m just getting started with startups. I am positive that I will build something big one day. First I got to learn from this. I’m hoping you might be able to help me out.

Startup 1: Brighten

I’m an avid reader, and the world of publishing seems ripe for disruption, so I’ve wanted to do a startup related to books since my junior year of college (I’m a senior now). My first attempt was called Brighten. It was a platform that let anyone make an online multimedia book. An older, more experienced entrepreneur fell in love with the idea, and wanted to help me make it happen. We found a developer that was willing to work with us, so we built a version 1 and showed it to our friends. The feedback was unequivocal: it was nice to have, but not necessary for anything. The user interface needed a lot of improvement.

After hearing that feedback, I got incredibly discouraged. I had a sick, sinking feeling in my stomach. I didn’t want to build something that people wouldn’t need. We’d never be able to get anyone to pay for it. I wanted to build a tool people would rely upon. I decided it was a better idea to focus on professional authors.

I drove to Chicago that weekend to stay with some friends that I knew would help me figure out what to do next. We took a lot of long walks, and sat around on their porch late at night, working through different scenarios. At some point, we started brainstorming another startup idea. It was a service that would let authors test their the shelf-appeal of their books. Users would sign up for a weekly email of upcoming books in the categories they’re interested in, and authors would pay to have their books be included in that list. You could see the first chapter of the book, and give the author feedback. Authors would get analytics, even the ability to A/B test their titles and openings.

Christine (one of my Chicago friends) and I stayed up until 3am researching and writing down our hypotheses. I went from the lowest despair to the highest confidence in just a weekend. I was sure this was a million dollar idea. Since this idea was just as much Christine’s as it was mine, and we had complementary skill sets, I knew I wanted to work on this idea with her. I would have to call it quits with Brighten.

Startup 2: Pencrafted

Christine and I decided to name our new venture Pencrafted. We talked to authors, all of whom assured us that they would not only use but pay for this service, assuming we could deliver on our promise of actionable feedback and metrics on their books. Everything seemed perfect with this idea, all we were missing was a programmer to join the founding team. I was reluctant to go with the guy I worked with on Brighten because, although he was a great programmer, he wasn’t excited about applying to TechStars or Y-Combinator and moving across the country.

Turns out, it’s incredibly difficult to find a tech-cofounder. You need to know the person before you start a startup together. Since you don’t have experience together, it’s impossible for them to fully trust your idea and your ability to build a company. It might look interesting, and it might be fun to work on for a bit, but to start a company you have to sacrifice a lot, and it’s a big risk. I don’t blame anyone for not wanting to take those risks. It’s definitely not for everyone.

Even though we couldn’t go any further without a programmer, we needed to feel like we were making progress, so we did fake work. We let our minds wander. We had doubts about whether readers would actually want to get a weekly email of upcoming books. We also knew we had a chicken-and-egg problem. Why would authors pay to reach no readers? Why would readers sign up if there were no books? These problems could have been solved, we could have tested our hypotheses, but instead we let ourselves get distracted by other, seemingly more straightforward ideas.

We decided to become a tool that let authors write books. It would organize your work into chapters, and export to ePub, PDF, and you could even order print prototypes. The business model was straightforward. You’d pay to use the software on a per-book basis, and also pay if you wanted to order printed copies. We started talking to on-demand printing companies, and talked to authors who again said they would use it and pay, assuming it was well-designed.

Then we realized something that we should have realized from the beginning: there’s not very many authors in the world, and they’re not very rich. Our total addressable market was just not very big. So we thought of different markets we could bring our technology to. One idea was to let schools use our software, and sell the books to kids parents. It seemed funny at first, then we realized how cool of a class assignment that would be for middle and high-school kids: write a novel. I would have loved the opportunity to do that! We started dreaming up a whole curriculum around this idea. It was a huge market (lots of kids in America), and the prices of printing a book seemed to be really low. Blurb sells paperbacks for as low as 4$ a pop. We talked to some principals and teachers, and they were all very enthusiastic about the idea. We talked to some parents and they said they’d definitely want to buy a book their kid wrote.

Then we started talking to quick-printers. They couldn’t believe Blurb’s prices (and I still have no idea how they keep it so low. Loss leader?). The best offer we could get was $11 a book, which doesn’t include any of the shipping and logistics costs. The margin we thought we could make was shrinking a lot. The more I researched, the more I realized that this startup idea did not have very much to do with creating a writing app. I am a web designer, and I just couldn’t get myself passionate about doing what it takes to start a bricks and mortar book printing company. The deal was sealed for me when we discovered that there were a couple other companies that did the same thing. Their branding made me want to throw up. I don’t know if this is an insecurity of mine, or what, but I just can’t picture myself being the founder of some “Kidz Bookz / Teen Lit” company. I was inspired by the idea of making a tool that professional authors would rely on.

Christine had the opposite reaction as I did. She wanted to make it into a non-profit, and was inspired by the idea of innovating educational curriculum. She wants to give kids in need the opportunity to create books, which is very admirable. But I just couldn’t get passionate about it. So we found ourselves with divergent visions. Now, Christine is going to think seriously about starting Pencrafted as a non-profit.

I’m not sure what comes next for me.