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Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (2 of 3)

This is the second in a series of three blog posts that are going to detail the events of the 24 hour, $100 challenge that two members of my mastermind group and I embarked on, from each of our perspectives.

  • In the first post, Josh Earl, Derick Bailey and myself talked about what we thought about prior to the contest, how we felt and prepared mentally, and what we planned to do.
  • In this post, we’ll each talk about what actually happened when the clock ticked midnight on Dec 17th, 2013. And how we survived the 24 hour ordeal.
  • Finally, in the last post, you’ll hear the final outcome of the competition as we each discuss our results, break down what exactly we think we did right and what we did wrong, and how we would have done things differently.

My story

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It begins!

The night before the contest I went to bed at 7:00 PM sharp. I had decided that I was going to wake up no later than 4:00 AM, but wasn’t going to try and wake up at exactly 12:00 AM. My thinking was that if I tried to wake up at 12:00 AM and was still really tired, I would actually be less productive and get less done. I wanted to try to get as much sleep as possible, but still not waste any time. I really just needed to get my landing page up before other developers got up and went to work–at least here in the US.

I ended up waking up about 2:00 AM, but I immediately felt like I did not want to work on this project for 24 hours. As I walked from my bedroom to my office, I started to have some serious doubts about whether I could actually pull this off–this was going to be a long 24 hours.

I decided the first thing I should do would be to plan out my day in detail. I opened up Trello and created a new board called “$100 in a day.” I started making cards in the “To Do” column. The first card I came up with was “Pick and register a domain.” I’d need some kind of a domain to launch my new site on since I couldn’t use my existing blog. After that, I added a card for “Set up a landing page on the domain.” I figured I could just setup a virtual private server at Digital Ocean and stand up a WordPress install on it. Then, came a card for “Plan what will go into the package.” I needed to decide exactly what I was going to sell. After that, was “Plan a pricing strategy.” Followed by, “Plan a giveaway for preordering” and “Make it possible to buy the package.” Finally came “Come up with the actual advertising plan.”

Setting up the landing page

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I started out by looking for an expired domain that had a high Google page rank, since I figured this might help me to give the site a bit of a boost in search engine traffic, but I quickly realized that I would have to bid on domains and that process would probably take several days. Then, I remembered that I already had a domain called “devcareerboost.com” that I was planning on using as a sign-up page for my future course, so I might as well use it for the landing page for the preorder as well.

I quickly threw up a new WordPress install on a virtual private server I already had on Digital Ocean and I was ready to create my landing page. The only problem was, I didn’t actually know how to create a landing page and I couldn’t spend all day figuring it out. What I needed was a proven landing page format that already existed, which I could just fill in the text. I remembered hearing about Leadpages and decided to give it a shot. I signed up for an account and in a few minutes I was looking at the landing page templates Leadpages made available to me. I decided on one that allowed me to have a video at the top of the page and looked pretty good for selling a preorder.

My next problem was that I wasn’t a copy editor. I really had no idea how to write good marketing copy for a landing page. I had written plenty of blog posts in the past, but writing marketing copy is a whole different beast. I decided my best course of action would be to try and modify the existing copy on the landing page template to suit my purpose. I also did a search online for some other long form sales pages that looked somewhat similar to mine. I tried to copy the tone of the examples I had and make mine look at least somewhat similar to theirs. I briefly considered hiring someone to do this part for me, but I realized that not only would I put myself in the hole money-wise if I did that, but I would also probably have to wait at least half of the day before I’d get the actual copy. I tried to not sound like a cheesy salesman, but I am pretty sure it still came out pretty cheesy. Oh well, at least I had something that might work. I could always modify it later.

I was starting to feel like I just might be able to pull this off, but I still had some big reservations about whether someone would actually click the buy button with all the cheesy copy I had just written.

Pricing the product

Next, I had to figure out exactly what was going to go into the package. I had figured that I would try and make the price-point be about $75, so I would only have to get two sales to make my goal. But, what could I produce that would be worth $75–on a presale that wouldn’t ship for 3 months? I decided to take a look at other similar packages to get an idea of what people were including and what price they were charging for the content. I knew I would have to discount my price a bit, because I was doing a preorder and my landing page was not exactly “optimized.” I decided to check out Nathan Barry’s site, since he had launched “The App Design Handbook” as a package and he had a similar audience to mine. I figured if I could provide at least as much content as the package that Nathan was successfully selling, then I could definitely ask a $75 price for it–at least while it was preorder, I could always raise the price later.

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It turned out that Nathan had a complete package which included his flagship App Design Handbook, 9 video tutorials, 9 video interviews and 5 additional resources for $249. I decided to try and match that content by having a flagship book, “Why Marketing Yourself Is Important,” and including a couple of complete video courses, some smaller eBooks and a bunch of video interviews as well. I wanted to err on the side of including too much content rather than not enough. (I wasn’t really thinking about how much would it would be later down the road to try and produce all this stuff in 3 months.)

By this time it was probably about 5:00 AM, but I was off to a good start. I filled in the details about the package on the landing page and put in the pricing information. Now, I just needed a way to actually take payments and deliver the product. I had already decided that I would probably use Gumroad for this, since they offer a really easy way to sell a product online. With Gumroad I could basically just put a link on my page that took customers to a checkout page and everything else was handled for me. I did need something to deliver to anyone who made a purchase, so I quickly created a Word document that simply said “This is a placeholder for the eBook you will receive within 24 hours. Thanks for your purchase!” (When you only have 24 hours, you do some pretty crazy things.)

Time to start marketing

I was finally ready to start seriously thinking about marketing. Now that I had a product that could be purchased, I needed to get the word out to as many potential customers as possible. I decided that I needed to work on the highest potential items with the least amount of effort first. My plan was to write up an epic blog post that would detail out a problem that my target audience faced. I decided that a large percentage of developers probably had faced the same kind of problem that I had faced in my career–a glass ceiling, where they couldn’t really rise any higher or make more money. I wrote a blog post titled “Why You Are Stuck In Your Career” and I talked about how you have to be able to break away from the pack in order to advance past the glass ceiling. I talked about how famous chefs and rock-stars were talented, but were no more so than hundreds of others who were relatively unknown. I specifically called out the reasons why top chefs and top musicians were able to make more money than equally skilled, but unknown counterparts–they had built a name for themselves. I then pointed the reader to my solution to this problem–my course on how to market yourself as a software developer. I figured if I could get traction on that blog post, then I could get enough readers to my landing page to make at least a couple of sales. This would be my main marketing strategy–I needed this thing to go viral.

I decided the best approach would be to start by emailing as many influential developers as possible, explaining the contest and my blog posts to them, and asking them to help me spread the word by tweeting the post out to their followers and sharing it on their networks. I was comfortable asking this, because I had created a quality post that offered real value to anyone reading it. I didn’t just ask them to tweet out my landing page, which would have been equivalent to just asking for handouts. It turned out this was quite successful and I immediately received back a few responses from some prominent developers willing to help me out.

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Now that I had some eyes on the post, I figured there was a good chance the post would do well on Hacker News, so I submitted it there, opened up my real-time tracking in Google Analytics and waited. It didn’t take long before the simultaneous viewers jumped from 2 to 30–the post was gaining traction. I checked and saw that it had been upvoted a couple of times, so even if it fizzled out, I should at least get some decent traffic. But, traffic is one thing and purchasing my $75 package is another. Would anyone actually click “buy?”

My first sale

My answer came pretty quickly. ** Within a few minutes I had my first sale.** I had to double check to make sure I was correct. But, it was true, someone had actually bought my product. A few minutes later another sale rolled in–I had already hit my target. Wow. I did not expect to succeed this quickly.

It was time to close down Google Analytics and figure out how far I could take this. Could I break $500 in a single day? $1000? I wasn’t sure, but I was determined to find out.

My next idea was to start hitting popular developer forums and posting about the product. Unfortunately, I didn’t really know many developer forums. I tried a few Google searches and didn’t come up with much. I thought perhaps I could submit my post to Code Project and see if that got any traction, but the post got rejected, because it contained advertising for my product. I registered for forums and posted some information about my product and a link to my blog post, but I didn’t really get much traction, since I was basically looking like a spammer. ** You really need to build a reputation in most communities before you can promote something of yours there.** I hadn’t really thought about this when I was planning out my strategy.

I decided that I should check to see if I could get an email list of developers that I could mass mail a message about my package to. I knew that I should be able to buy targeted email lists, but I wasn’t sure exactly where or how to do it. I figured my best bet was to try looking for someone on oDesk who could send an email to 1000 developers. I put up a job request and explained what I wanted done. Then, I moved onto other activities, since it would take awhile for someone to get back to me.

Slowing down

I was at a loss for what else I could do. It was only about 12:00 and I was pretty much out of marketing ideas. Other than directly contacting people one-by-one on Facebook or Twitter, I couldn’t think of another way to spread the message. Everything else I came up with involved reaching out to people individually and that kind of thing would not scale. I knew that I needed about 100 to 200 people to hit my landing page for every sale that I was going to make. By this time, I had gotten a few sales and I started to figure out an estimated conversion rate.

I decided that I would try the thing that had worked the best so far and write another blog post framing a problem and then offering a solution. I wrote up another blog post titled “Why You Aren’t Paid As Much As You Are Worth.” This one talked more about the idea of most software developers being a commodity and how you could differentiate yourself through marketing to become more than a commodity. I pointed out the solution to this problem is knowing how to market yourself and I included a link to my landing page where I offered to sell the solution for just $75. I felt like the post was pretty good, but it sort of fell flat. It didn’t get much traction from Hacker News or Reddit. (Possibly due to the fact that I had just written about that topic earlier that day.)

I had one last idea before I would give up and start writing the book that I needed to ship in under 24 hours–Google+ communities. I figured I might be able to find software developer communities on Google+ that I could join and drop a link to the first blog post I had written that had done well that morning. I joined about 30 communities and put my post out there. It turned out to be a pretty good idea, because I did start seeing traffic from Google+–not as much as Hacker News had generated, but it was something.

Writing the book

I decided the best use of my time at this point would be to write that book, because if I didn’t get a first draft out by the next day, I’d be issuing lots of refunds. I started writing like a madman, but of course it was pretty easy to write about the subject, because I had spent all day thinking about it and had already given several talks about marketing yourself as a software developer. I stopped to eat dinner, but then went right on back to writing.

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I took a break in the evening to check up on oDesk. It turned out that I got several responses from freelancers that could get me a list and send the emails out, but it didn’t look like anyone could meet my time line. I was a bit hesitant about this approach anyway. I didn’t feel like this was the same as “cheap discount Viagra,” but it still felt a little spammy. Not an approach that I would have done normally, but I figured for competition sake, if I could pull it off, I might as well try. I ended up talking with the most hopeful prospect, but it turned out to be a bust.

I pretty much spent the rest of the night frantically writing my eBook. I finished the last chapter of the first draft at about 10 minutes till midnight with a total word count of around 12,000 words. Between the book and the two blog posts, I had written about 15,000 words that day. I didn’t have any trouble falling asleep that night. (Mind you, this was only the first draft of the book. I spent much more time adding content and revising this draft over the next few weeks.)

Derick’s Story

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I did not sleep well, the night before the challenge. Sure, I went to bed at 9pm – but what does that matter when you don’t get to sleep until 10:30, and that sleep is more like tossing and turning all night? The fear, the anxiety, the doubts all raced through my mind. I eventually did get to sleep, but my plan of waking up at midnight to get started was already looking like a bad idea.

Today’s Tasks

When the alarm finally did wake me up, it was 4am instead of midnight: first fail of the day. I was four hours late getting started. But I crawled out of bed, got some food and sat down at my desk to get rolling. I had two things to do this morning:

  1. build a website to shamelessly ask for money
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And right here, right now, I have failure #2: I bailed on the website to shamelessly ask for money. I just couldn’t bring my self to do it. My stomach was twisting and turning as I was about to click the buy button on a domain name.The fear of being called out, told I’m a scamming fraud and marketing sleezebag got to me. Combine that with only a few hours of sleep, and I bailed on the first thing that could have made me some money. Of course I justified it to myself. I told myself it was ok to bail because of waking up 4 hours late. It’s easy to justify things like this. There’s always an excuse. What isn’t easy is admitting that you bailed for fear and self-loathing – but that’s exactly what I did. I regret not doing this, not having tried and seen what it may have brought.

Getting Started On The eBook

I pushed that website aside and got cracking on my eBook for podcasting. I’ve been using LeanPub.com for ebooks already, so it was a simple thing for me to get another one started. I created an empty shell of the project, gave the book a name, waited for my dropbox folder to update and started cranking out the book by designing the cover, first. It was important for me to have the cover because Leanpub will show the book cover on your page, after you generate your first preview of the ebook. Having a good cover can make or break the first impression when someone hits your leanpub page. I’ve dealt with bad covers in the past, so I wanted to make sure I had one that would stand up to that first impression this time.

A few weeks prior, I had bought a bunch of credits on depositphotos.com and it was paying off now. A few quick searches later and I had a great image for a book cover, that didn’t need too much added to it. All together, I think I spent an hour getting the cover put together. Combine that with the 30 minutes to get Leanpub set up and another 30 minutes to put together a very rough chapter outline, and I had my first ebook preview generated in a couple of hours. With the preview generated, and the book cover showing on the Leanpub page, I set a suggested price of $10 and got started on the real content.

Cranking Out Content

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The next few hours were a mix of cranking out content, combined with combing DepositPhotos for the perfect images to illustrate what I was saying. It was a caffeine fueled joy-ride, and what a caffeine rush it was! At this point, I had been off caffeine for nearly a month. So the one 12oz can of Diet Mountain dew that I had around 7am gave me a massive buzz and really helped me push through the long day. I wrote a total of 4 chapters for the book that morning, added a number of images to the chapters, and previewed the ebook through leanpub multiple times.

About halfway through the morning, though, I had to step back and re-formulate the name and chapter outlines. I realized that my book had gone too far down in to the weeds of recording and editing, but didn’t cover enough of the planning or publishing side of things. It took about an hour for me to redo the leanpub setup and the book cover. This was an hour that I should have spent on content, but it was a necessary chunk of work so that the book would make more sense. In the end, I’m glad I made the change.

By the time 12 noon rolled around, I had 4 chapters and a book that would at least get people to record a first podcast episode. I was read to stop writing and start working on the marketing side of things.

The Marketing Effort

All that fear, all the anxiety… everything that I hated about this challenge came right back up front and center when I hit publish on the book for the first time. Now, suddenly, I don’t have a concrete thing to build – something to distract me from the work that I was dreading. Now I have to face my fears and anxiety, and try to actually sell this thing? What the crap am I supposed to do, here? How am I supposed to sell this? Well, ok. I’ve done this before with my screencasts. I’ve engaged an audience and convinced them that what I have is worth some money, through twitter and blogs. So I’ll start there. I’ll blog about the book. I’ll setup a web page at http://blog.signalleaf.com/how-to-podcast, and I’ll use that as the landing page and marketing copy. The blog post will follow, and will be an announcement / introduction style, while the landing page itself will be the real marketing copy.

It took me nearly an hour to get the landing page built, get the book image added to the sidebar of the blog, add the menu link at the top of the site and build that big green “buy now” button for the page. I think 20 minutes was spent on that button alone. I had such a hard time getting it to look and behave the way I wanted. But in the end, I had the page and I had a blog post to announce the book. Now how do I get it in front of people?

I turned to twitter, my old friend. I’ve done this before so why not do it again? Only this time, I can’t use my @derickbailey account. I can only use my @signalleaf account. For the next few hours, then, I was combing through twitter searches, looking for people that were asking about how to start a podcast. It’s actually quite surprising how many people are asking about this, on a daily basis! I had no shortage of tweets to which I could respond. What I had a shortage of, however, was courage. My stomach was again turning in circles. So I did what any other marketing n00b would do: I went and got lunch instead of doing the marketing. I had to eat, right? Let’s do that instead of doing the hard work.

The Sales Pipeline

When I got back from lunch, I had no more excuses. I had to actually reply to people on twitter and start engaging them. So that’s what I did. I started by tweeting my blog post about the book, of course. But I had so few followers that it wouldn’t matter. So I went back to my twitter searches and started trying to find ways to talk people in to buying the book.

I’ve never believed in “sales”. I’ve always believed that if I’m truly passionate about something, and that I have something valuable, people will see it and want it. It’s natural for me to talk about the things I love, and people will gravitate toward that. I do this all the time in blogging and in software development. But I quickly found out that this wouldn’t make a meaningful dent in my goal of earning $100 in one day. Sure, my engagement of the twitter crowd did produce some great conversations. I found some good podcasts, found a lot of great people who wanted to get started, and answered some questions. I used twitter as a method of engaging the people who would benefit from buying this book. But I never once tried to sell the book, and so I never actually sold any that day.  The closest I came to selling a book was when I gave a free copy to a podcaster. I was hoping that she would like the material I was producing, since she was also producing “getting started” material in her podcast. That never panned out, though. Even after conversations on twitter went well, she did not download the book until a few days later – long after the contest had ended.

Closing My Day: $0 Earned.

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Throughout the afternoon, I continued to work on the book. I looked for blog posts that I could comment on, to link back to me. I engaged twitter. I did a lot of things that would build long term credibility, basically. And halfway through chapter 5, I also realized that I needed better info on MP3 bit rates, audio quality and file size. This prompted me to record a short podcast, which I extended in to a 32 minute episode and exported at 10 different bit rates. The results of this experiment, showing the effect of bit rates on file size and audio quality, are found in this blog post: http://blog.signalleaf.com/blog/2013/12/18/mp3-bit-rates/ By the time the end of the day rolled around (and I do mean “end of day” – I stayed online until midnight, tweaking the book, engaging more people via twitter, and generally trying to build my audience) – I had sold nothing, but I had at least gained a great asset that would be an introduction to world of podcasting, for others. That in itself was a success. The challenge day: fail. I earned nothing, and therefore failed the challenge. I emailed Josh and John, let them know my results for the day:

  • 7K+  words written
  • 5 chapters of a brand new book
  • 1 book cover design, with a dozen or more image manipulations for the book pages
  • 1 web page / book page and
  • 2 blog posts
  • 10 exports of a single podcast episode, with a complete RSS feed for the special-edition podcast
  • 2 comments on relevant blog posts, with 1 link back to my blog
  • several conversations engaged on twitter
  • give away 1 copy of the book to a person on twitter (who has yet to claim it)
  • 1 tweet from a podcast that I’m sponsoring, about my book
  • 16 unique visitors to the blog
  • 1 new trial account signup (though I think it’s not going to go anywhere, I’m happy to have another trial signup)
  • 0 sales, $0 income and 0 email list signups for Signalleaf

I did end up selling 1 copy of the book, by the way. But it wasn’t until after 1am – an hour after the challenge ended. So that $10 did not count toward my goal for the day. Since then, I’ve made the book “free” for signing up on my mailing list, I’ve added a number of checklists to to appendix, and having given away around 20 copies. The book itself is not yet finished, but it’s a great start and something that I will be working on throughout the rest of 2014.

Objectively, the day was a failure. The goal was to generate income and I completely, utterly failed at that. Long term, the day was an outstanding success. I set in motion a ton of things, completed a number of my commitments for the week, and had a ton of fun staying up for 22 hours, hacking away on things! icon biggrin Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (2 of 3) If this were re-branded as a marketing hackathon day, I would be in strong standing with a good chance of taking home first prize. I kicked ass on creating new content, producing material that is tremendously valuable to the podcasting community, and engaging the community through blog posts and podcast episodes. It was a good day.

Josh’s Story

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Battle plan

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I didn’t sleep very well. My brain was looping relentlessly, rehashing my plans for the challenge.

When I finally got up, around 4 a.m., I didn’t feel great. No, scratch that, I was miserable. I was a weak-kneed, sour-stomached ball of anxiety.

Still, I got up, took my usual morning shower, and settled down to work around 4:30 a.m.

My battle plan was simple. It all hinged on writing a killer blog post, then ensuring that this post was a hit that attracted thousands of visitors to my site. I’d use this burst of exposure to build a small email list by offering a giveaway related to the topic of my post. Then I’d use my experience with email marketing to my advantage to sell … something … and win the day!

To make this work, I’d need to write a blog post, set up a mailing list opt-in form, promote the post, settle on a product, write a sales page, write the giveaway I was promising all of the people who were joining my list, and send out the email that would bring in the sales. The audience was more important than the product; with enough traffic, I should be able to sell whatever I came up with …

Off to a rousing start

The blog post was the linchpin, the key to the entire day. There was a lot riding on it. My plan called for me to finish it by 7 a.m. so I could publish it on Hacker News before the site got too busy, maximizing my chances for a front page hit.

So naturally the first thing I did when I sat down at my desk was … start researching the product I was going to offer. Particularly, what tools I would use to create it. Typical software developer…

I was considering two different options for the product. I didn’t want to presell something that I’d have to spend weeks creating, so I’d settled on doing some kind of live event. My blog post was going to be about the success I’ve had marketing my Sublime Text book over the last 12 months, so I thought I could try to sell either some 1-on-1 coaching-type sessions with aspiring self-published authors, or else a webinar-format event where I walked participants through what I’ve done to promote my book.

Like many developers and writers, I’m an introvert, and just thinking about doing either of these events made me a little sick. I let this anxiety immediately derail my plan.

After an hour or so of comparing software platforms, I decided that I’d offer seats to a private Google Hangout, and I’d use Eventbrite to sell the tickets. This didn’t help my anxiety much, but at least I knew what I was going to be selling.

Reverse-engineering success

With that research out of the way, it was time to get writing. The post really was important, and I needed to get it out stat.

Sounds like a good time for … more research!

I spent the next 30 minutes or so reviewing popular posts on Hacker News, particularly Nathan Barry’s always popular book launch postmortems. He devotes a lot of space to numbers and specifics, I noted, and his posts are heavy on charts and graphs, along with some analysis of what went right and what went wrong. I also dissected the headlines he used—the headline is by far the most important contributor to the success of a post.

Unlike my first research excursion, this was time well spent. I could have been much more efficient, though, because …

By the time I finally cracked open Sublime and started writing it was 6:31 a.m.

That 7 a.m. deadline wasn’t looking too good …mess thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (2 of 3)

I average around 800 words an hour when I’m in a groove and working on a focused topic with a good outline. Unfortunately, I was about as far from those ideal conditions as possible.

To start, the topic was very broad—I was going to try to cover more than a year of sales ups and downs in one post. There was my nervousness about pretending to know something about marketing when there are so many truly skilled marketers out there. What if they laughed at me or left mean comments?

And then there was this truth: I secretly hoped I’d fail. Putting myself out there in this post was bad enough, but success meant I’d have to go through with the live event, which was an even worse prospect.

My writing discipline crumbled. I broke all my rules. I researched as I worked. I didn’t write a thorough outline. I didn’t write a first draft without editing. I scrolled, I tweaked, I revised.

And the results were predictable. It turned out to be a good post, 2,035 words long, with a half dozen graphs and charts to break up the wall of text and prove my results. But it took six hours to produce, and I didn’t push the publish button until 12:34 p.m.

Emotionally drained, I posted the link on Hacker News and Reddit and went to lunch.

My fate was in the gentle hands of Hacker News

Google Analytics is pure productivity Kryptonite. Especially since they added the realtime current visitors counter.

All through lunch, I kept an eye on that counter to see what my fate would be. Would Hacker News take an interest in my post, or would it quickly disappear under a pile of NSA revelations?

For a few minutes, it looked like it was going to catch. My simultaneous visitors count climbed to the upper single digits. I know from past experience that this is the make-or-break point—if you don’t get into double digits within the first few minutes, your post will probably only going to get a couple of hundred visits from Hacker News.

Then the counter started to drop.

A feeling of relief washed over me. Without a traffic surge from Hacker News, there was no way my plan could work.

Oh, well, I’d given it my best shot, and I’d failed. Now I could relax and not worry about the contest.

It’s all over. Right?

When I got back from lunch, I decided I should at least go forward with some of my plans to promote the post—no sense letting my work go completely to waste.

I sat down and started sending emails. I planned to individually contact each of the influential people I mentioned in the post and thank them for helping to make my success possible. I included a link to the post but did not specifically ask them to share it. My list of influencers included Peter Armstrong of Leanpub, Pat Flynn, Nathan Barry, and Jesse Liberty.

As I worked, I noticed my Google Analytics counter start to creep up again. My post seemed like it was showing some signs of life on Hacker News. Uh oh…

Then it shot up like a rocket—now more than 120 people were reading the post at once! I’d hit the front page, and I was getting hundreds of new hits every few minutes.

I was back in the game! I was still sick with anxiety, but this traffic spike gave me the courage to keep going. I sent a few more emails to friends and acquaintances, asking for a tweet or a like.

The responsesstarted arriving. Peter Armstrong responded and said he’d tweeted the article three different times. Moreover, he was wondering whether I’d be interested in allowing him to republish it on the Leanpub blog. That was my first invitation to guest post—I was stoked! It wouldn’t help me with the contest, but it would help me build traffic long term to my blog. Jesse Liberty replied to let me know he tweeted the post.

But my biggest shock came when I emailed Pat Flynn—and got a response two minutes later!

pat flynn 1 thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (2 of 3)

I was convinced I’d triggered a reply from a crafty autoresponder—Pat is a ninja with clever productivity hacks like that. I replied that I’d be happy to offer a testimonial, then asked for a tweet or Facebook post. And he responded again:

pat flynn 2 thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (2 of 3)

Score! Pat’s audience was a perfect fit for the topic of my post and seemed likely to be interested in my self-publishing Hangout.

After a couple of hours of promotion, I was running out of people to contact.

But was it working?

By this point, the blog post had generated a couple of thousand visits. That part of my strategy was working as planned, but was I getting the email signups I needed to be able to sell seats to my Google Hangout?

I logged into MailChimp to find out.

Oh, not good. Traffic was trending down, and I’d only gotten 9 subscribers. Hacker News traffic doesn’t usually convert well to email sign ups—I was prepared for that. But I had hoped that a front page hit would bring in enough volume that I’d still get 5 to 10 times as many subscribers as this.

After considering my options for a few minutes, I decided that I needed to change gears. This indirect approach wasn’t going to get me the numbers I needed—I had to pitch the Hangout directly at the end of the post, where it would be seen by more people.

But first I had to get the event scheduled. I jumped over to Eventbrite and fumbled my way through creating tickets for an online-only event. I settled on a price of $25 per seat, which would allow me to make $23.97 profit per sale. I’d need to sell five seats to hit my goal.

Now that I had a link, I updated the call to action in my post: Instead of encouraging readers to sign up for my email list, I promoted my self-publishing Google Hangout.

Running out of gas

It was 2:58 p.m. when I finally started promoting my event. Was it too late? I needed more traffic, but I was getting low on ideas. My personal network was tapped out, and I’d implemented my best “instant traffic” tactics.empty gas thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (2 of 3)

While I waited to see if my updated call to action would net any sales, I started looking for other places to promote my post. I jumped on to Facebook, where I belonged to a self-publishing group run by Pat Flynn, and posted a comment about my post there. This generated several questions and responses, which I responded to.

I googled phrases like “self-publishing” and “marketing an ebook,” looking for highly ranked blog posts that would allow me to add a useful comment and a link back to my post, naturally. This didn’t seem likely to help me out much in the contest, but I knew it would create a small but steady stream of traffic to my blog in the future.

And a sale!

At 4:53 p.m., my efforts paid off—an email landed in my inbox informing me that I had sold a seat to my Hangout! I was relieved. At least I was in the game. How many more sales would I be able to get before midnight?

I was now officially out of ideas for promoting the post, so I decided to break for dinner and some family time.

More resistance?

The resistance that I battled all day returned with a vengeance when I sat down to tackle my last task for the day—creating the giveaway I’d promised to get readers to sign up for my mailing list. Would this list of tools even be useful to anyone? The whole idea seemed stupid. People were going to be mad at me when they got it.

But I’d committed to putting it together, and I really didn’t want to leave this task hanging over my head, so I forced myself to start working on it.

I’d planned on about 30 minutes for this, so of course it took more like 90. I finished it at 8:32 p.m. and decided that I was done for the night.

Before I put away my laptop, I decided to check Google Analytics one more time. Whoa, my realtime counter said I had 60 people on my site! Pat Flynn’s promised tweet had just hit. Another nice burst of traffic to wrap up the day.

I turned out the light, knowing full well that Derick and John were still cranking away. But after a day of wrestling my inner demons, I didn’t much care. I’d executed my strategy. I’d survived. I’d made some money.

Was it enough?

Grand finale coming up

Want to find out what happens next?  In the last post in this series, we’ll each talk about what the final results were and what we learned from the experience.  Sign up here to make sure you don’t miss that next post.

Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)

You are dropped in the middle of the forest by helicopter with nothing but a hunting knife. What do you do? How do you survive?

That was the basic premise of the challenge a couple of my buddies and I undertook, only instead of our competition taking place in the woods, ours took place completely online.

wilderness survival thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)

The idea was pretty simple. You have one day–24 hours–to make at least $100 online. The only catch is you can’t use anything you have already. You can’t use your Twitter account, you can’t use your blog, you can’t sell some product you already created; whatever you do, you have to do it within 24 hours and you have to get cold hard cash–I owe yous don’t count.

This is the first in a series of three blog posts that are going to detail the events of this story from each of our perspectives.

  • In this first post, Josh Earl, Derick Bailey and myself will talk about what we thought about prior to the contest, how we felt and prepared mentally, and what we planned to do.
  • In the next post, we’ll each talk about what actually happened when the clock ticked midnight on Dec 17th, 2013. And how we survived the 24 hour ordeal.
  • Finally, in the last post, you’ll hear the final outcome of the competition as we each discuss our results, break down what exactly we think we did right and what we did wrong, and how we would have done things differently.

My story

IMG 0037 withoutlogo Mobile thumb1 Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)If you follow my blog, you probably already know a bit about me, but I’ll introduce myself for everyone else. My name is John Sonmez. I’ve been a software developer for about 15 years–at least that is how long I have been doing it professionally.

I’ve worked for large and small companies, worked as a contractor and an employee and used a wide variety of programming languages and technologies, but my true passion has always been teaching.

A few years ago I started making courses for Pluralsight and during that time I produced 54 courses on everything from Android and iOS to game development. The success from this venture allowed me to quit my job and work full-time on my own company, Simple Programmer. Since then, I’ve been writing blog posts, making YouTube videos, creating podcasts and producing products to help developers in all areas of their life.

The challenge

I have to admit, I was a bit intimidated by the challenge–even though I was the one who proposed it. It is one thing to talk about making $100 online in 24 hours–it is another thing to try and do it.

I felt pretty confident that I could easily accomplish this goal right up until the point that we actually set a date on the calendar and committed to doing it.

One of the rules we had set out was that we couldn’t actually write down anything or do any prep-work ahead of time–it all had to be in our heads. I figured that I had better come up with some idea of a plan, so I started thinking about some of the possible ways that I could earn $100 in a day.

One obvious way was just to start randomly begging people for money. Explaining the contest itself was not against the rules, so I could basically pitch people by telling them I wanted to win this contest and see if they would contribute. I was pretty sure in 24 hours I could talk to enough people to scrape together the money, even if I had to do it one dollar at a time, but that idea didn’t really seem too appealing to me.  I wanted to do something for this contest that would have the potential of benefiting me in the long run. (I did stash this idea as a last resort to use in the case that my main plan failed though.)

The next idea I had was to do some kind of affiliate marketing. At the very least I could try and market some Amazon products and get a 6% commission on whatever I sold. But, I could also find some other high commission product and try to sell it. The problem with this approach would be that I wouldn’t really have any audience to sell into; I’d basically have to be like a door-to-door salesman randomly posting on forums and Facebook groups trying to make a sale. Also, it wouldn’t have any long term benefit to me. This option seemed viable, but I thought there had to be something better I could do.

My next thought was to create a small product that I could sell. I thought perhaps I could put together a small eBook that was somewhere around 5,000 to 10,000 words and put up a small website to sell the eBook. The only problem with this approach would be that I would have to spend a large amount of the day writing the eBook and then I’d have to try and get traffic to my sales page. But, at the end of the day, I’d actually have a product that I could sell and improve in the future. This idea seemed promising, but how was I going to write a book in a single day and still have time to market it, and what should I price something like this at?

The product

I had a couple of weeks until the competition, so I spent some time during my running workouts thinking about my strategy. I was pretty sure I was going to create some product and try to sell it, but I wasn’t sure exactly what kind of product I should create and how I should price that product.

One thing that occurred to me pretty early on was that I if I sold something at a low price, I’d have to make a large number of sales, but if I was able to create a product that I could sell at a high enough price, then I could possibly reach my $100 goal just by making one or two sales. It seemed that it made the most sense to try and sell a high-priced item, since there wouldn’t be enough time to do enough marketing to get the traffic needed to sell a bunch of little items. But how the heck could I make something in less than 24 hours that I preselling thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)could sell for a large amount of money?

It turned out that I had already planned to create a course that was going to teach developers how to market themselves in order to get better jobs and boost their careers. I had come up with this idea, because I had realized how valuable the publicity I had gotten from my blog, podcast, and Pluralsight courses had become to my career, and I felt that I could condense the information I had learned from this experience into something that just about any other developer could recreate. The only problem was that I had planned to create this course the following year and the course was going to take a long time to create–we are talking months, not weeks.

Then, I had a brilliant idea! What about preselling the course? I could create a first draft of one of the eBooks for the course and give it away within 24 hours for anyone who bought the presale of the entire course. If I told the customers who prebought the course that they’d get the eBook within 24 hours of their purchase, it would actually even buy my an additional 24 hours to create the book. (None of this was against any of the rules for the contest, since I would be getting the money during the 24 hour period, even if I delivered the goods later.) It was a bit risky–I mean, I would still have to write an entire first draft of a book in about 24 hours–but I thought this was the best chance of selling a high priced item. As an added bonus, all the work for the competition would force me to actually create the product I had been planning to create the next year and would actually give me a head-start on doing it.

The strategy

Next up was trying to figure out exactly what I was going to do tactically to get this product up for sale and to make the best use of my 24 hours. I had to do quite a bit of running and rehearsing in my mind, but I came up with what I thought was a solid plan.

I decided that I should probably go to sleep really early the night before the competition and try to wake up right around midnight in order to maximize the amount of time I had to actually create and sell my product–this was pretty obvious and I expected my competitors to do the same.

Then, I started thinking about what order I would probably want to do things. It seemed to me that I wanted to have as much time as possible to market the product and have the product for sale, so the first priority would be to stand up some kind of a landing page and make the product available for sale as soon as possible.

But, the real big problem was how to market this thing. What do you do when you only have 24 hours and you can’t use your existing social platforms? If I could send an email out to my email list or make a post on my blog, this would be easy, but starting from scratch and only having 24 hours makes this rather hard. I thought about some of the things I could do to spread the word.

One obvious thing would be to email other developers that I knew, whom had big audiences, and see if I could get them to mention my product on their social networks. I thought I could probably come up with a pretty large list of developers that might be willing to help me out and I could send out one email to all of them, which would leverage my time effectively.

Another idea I had was to write up some kind of epic blog post that I could get on Hacker News or Reddit. I would have to create a brand new blog to do this, since I couldn’t use my existing blog, but if I was successful, it could generate quite a bit of traffic to my landing page and with enough traffic, I should be able to get the few sales that I would need.

I also considered that I could post in various developer forums and communities. I could either answer posts or create my own post that would have some relevant information, but eventually lead someone to my landing page. It would be another way to extend my reach by borrowing another audience.

Finally, I thought as a last resort I could purchase a list of developer email addresses and send out a one-time email blast to try and sell the product. It might be perceived as spam, but if I could send out an email to a large enough list of developers, I would at least be able to make a few sales.

I had to keep thinking about this list of marketing ideas in my head so that I wouldn’t forget them before the contest, since I wasn’t allowed to write them down.

So, that is it. That was my plan. I was going to create a landing page for my How To Market Yourself as a Software Developer course as quickly as possible and try to market it mostly by leveraging existing audiences since I couldn’t use my own. I felt like it was an OK plan, but I still had some serious doubts and reservations about my ability to pull it off.

It might not sound like much, but this challenge was daunting to me. Sure, I’ve earned hundreds and even thousands of dollars in a single day with screencast releases, book sales and other things. But having to do this in a single day, using no existing assets or networks… I’m getting that tight chested, stomach churning fear just remembering it.

Derick Bailey’s Story

derick Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)Derick Bailey is an entrepreneur, problem solver (and creator? icon razz Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3) ), software developer, screencaster, writer, blogger, speaker and technology leader in central Texas (north of Austin). He runs SignalLeaf.comthe amazingly awesome podcast audio hosting service that everyone should be using, and WatchMeCode.net where he throws down the JavaScript gauntlets to get you up to speed. He has been a professional software developer since the late 90’s, and has been writing code since the late 80’s. Find me on twitter: @derickbailey,@mutedsolutions, @backbonejsclass Find me on the web: SignalLeaf,WatchMeCode, MarionetteJS, My Github profile, On Google+.

Deciding What To Do

We talked about this a number of times before we set the date, and in those discussions I decided that I was going to focus on my SignalLeaf service for this day. Yes, SignalLeaf was something that I had already started, but it had next to nothing in terms of traffic and network. There were only a few followers for the @SignalLeaf Twitter account, there was next to no traffic on the blog (a blog that barely had a post or two on it) and the site was not getting any significant use. John and Josh both graciously agreed to let me focus on SignalLeaf since anything else would potentially mean starting up a new business model or finding a one-time thing to do. I wasn’t really interested in finding a new business model, though the one-time-only idea had me interested.

signalleaf logo Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)

Creating A Plan

After getting SignalLeaf approved by the other guys, I made a plan in my head for what I was going to do. I would focus my day on creating and selling an eBook on how to get started in podcasting. I wanted to help people get past their fear of starting, their fear of failure and their constant delay tactics. I wanted to show people how easy it is to get started in podcasting, and give people a clear path to getting their first episode online. An eBook seemed like a great way to do this, and I’ve had a lot of success with my Building Backbone Plugins eBook. So that was set. The eBook would be my majority focus for the challenge day.

large thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)

But after I settled on the eBook, I thought of something else… something a bit devious and underhanded. In addition to the eBook, I decided I was going to build a website that quite literally asked people to give me money just so I could win this challenge. I would buy a domain name on the day of the challenge, stand up a very simple page with a PayPal donate button and find a way to get people to it. Since we couldn’t use our own existing blogs or social networks, though, my plan was to borrow someone else’s. I was going to email a few very well known developers and friends, and beg them to tweet a link to my new site. It was sneaky, dirty fighting and totally sounded like something worth doing just to win.

So the rough outline for my day, with both an eBook and website to build, would be:

  • 12am (Midnight): wake up and get breakfast
  • 1am: buy a domain name for the “give me money” site
  • 2am: publish the site
  • 3am: start writing the eBook on podcasting
  • 12noon: publish whatever I had on Leanpub.com, and build the marketing page
  • 1pm: begin marketing the book through any means I could think of
  • 12am (midnight – 24 hours later): get one final report of any income I had earned that day

Awesome. Plan set. Wife and kids informed, and vacation day from work scheduled. Now, I wait for the day to come.

The Mounting Fear

fear thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)

As that day got closer, I became more and more fearful – fear of failure, fear of being laughed at, fear of having someone call me out and tell me I’m a fraud or some kind of marketing shill just begging for money. It was terrifying, and I let that fear get to me. I continued to make my plans in my head. I thought about what the eBook would say. I considered ideas for building the “give me money” page. I wondered about how I would email people about it. But all the time, while I was thinking about these things, I felt my stomach turning in circles and tying in knots. The closer the day got, the worse I felt.

Honestly, I wanted to give up even before I started. I thought about the book I was going to write and whether or not I could even market and sell the thing. I wondered about the viability of selling a book on podcasting when there are so many resources for getting started in podcasting already. I even sent an email to Josh and John expressing my concerns about being able to sell this. The fear was killing me, and I wanted to give up. But I didn’t and I’m glad I didn’t – not because I was successful, but because of the things I learned from that day and the effort I put in to it.

So It Begins

The experience of throwing yourself in to the woods with nothing more than a knife is terrifying – even more so when you know it’s coming. So I went to bed early and tried to sleep, with my brain running wild with ideas, keeping me awake longer than I should have been. Then my alarm clock went off and the day was here. I pulled myself out of bed and got to work.

Josh Earl’s Story

josh earl Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)Josh Earl is a software developer, writer and entrepreneur from Pittsburgh, Pennsylvania. He is the author of two self-published books, Sublime Productivity and Writing Sublime Plugins, both about Sublime Text, which is also the topic of his SublimeTextTips.com blog. He also runs DeskHacks.com, a site for standing desk enthusiasts, and blogs about writing and business at joshuaearl.com. His Twitter handle is @josh_earl.

Challenge accepted…

When John first proposed this challenge, it sounded like a blast. Take a vacation day, spend some time hacking on a business idea, taunt friends via email, make some money. What fun.

And even better, I thought I had a decent shot at winning.

I have a little experience doing business online. I’ve published and marketed an ebook about Sublime Text that’s earned nearly $20,000, created several blogs that receive thousands of hits a month, and started a niche site that earns hundreds of dollars a month in Amazon affiliate income. I’ve built a collective Twitter following of nearly 13,000 and a mailing list subscriber base of more than 5,000.

sublime productivity thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)

I’ve also enjoyed some success with generating “instant traffic” for my sites. I’ve had four posts featured on LifeHacker and another half dozen or so that spent a few hours on the front page of Hacker News.

Once the battle lines were drawn, my plan coalesced quickly.

I’ve proven to myself that I can get traffic quickly, so I decided to play to that strength. If I could get enough traffic, I knew I could figure out a way to convert that into money.

What could I create that would generate thousands of visits?

The answer was obvious.

There’s a blog post I’d wanted to write for ages, It was going to be a behind the scenes look at how I’d grown my audience and my income in the year since I published my book. I’d be as transparent as possible and share what I’d done well and where I’d fallen short. Then I’d wrap it up with a summary of some of the lessons I’ve learned over the past year.

The web loves these posts—Pat Flynn built much of his following around his monthly income reports, and Amy Hoy and Nathan Barry have also used them to good effect.

I had a good story and inspiring results, and I knew if I wrote the post it would be popular.

swing hard thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)

I decided to bet the farm on this blog post. I’d invest whatever time was necessary into writing and promoting it, then spend the rest of the day figuring out how to earn a few bucks from the torrent of traffic.

I had several ideas that I hoped would increase my chances of hitting a home run. First, Hacker News. A post that lands on the front page will receive dozens or even hundreds of page views a minute. I thought I could engineer a front page hit if I posted early enough in the day (7 a.m. Eastern in the U.S. is primetime). To maximize the appeal of my post, I planned to study several examples of income report-type posts that had done well on HN and use their headlines and structure for inspiration.

Second, I’d be as open and honest as possible about my successes and struggles. This post would be genuine and informative.

Third, I planned to mention well-known people who contributed to my success, giving me an excuse to reach out to them directly via email or on Twitter and ask them to share the post with their larger audiences.

To summarize my traffic generation strategy, I planned to write a killer post in a genre that I knew was popular with a specific audience, then try to borrow other people’s audiences to help me get the word out.

But how could I generate income from this traffic?

If there’s one thing I’ve learned in the past year, it’s that email is the best tool for selling products online. From my experience marketing my Sublime book, I’ve learned how to use a free giveaway as an incentive to get people to sign up for my mailing list, and I’ve also learned how to get people to open and read the emails I send.

I planned to use the same tactics that I’ve used effectively to market my book—only this time I’d do it at warp speed. At the end of my post, I’d entice readers to join my newly created mailing list by offering a useful giveaway. This “lead magnet” would be something related to the post—maybe a list of tools that I’ve relied on to create and market my book.

That meant I’d need to create the giveaway and write an email welcoming people to my list and linking them to the list of tools. I knew from experience that this email would get a very high open rate. I also knew that adding a P.S. to an email is a great way to draw attention to a message—after the subject line, it’s the one thing most readers will see. So I’d use a P.S. in the welcome email to promote whatever product I decided to offer.

Oh, yeah, that.

What in the world could I sell?

In addition to the contest rules, I had a self-imposed constraint that limited what I could offer: I didn’t want this product to require much of an ongoing commitment after the contest ended. That meant that preselling a book was out—at the time, I was hip-deep in editing my next Sublime Text book, Writing Sublime Plugins. The last thing I needed was another massive writing project to feel guilty about.

Two ideas seemed to fit: I could offer to let people book some time with me for one-on-one marketing help, or I could sell seats to a Google+ Hangout where I delved deeper into how I’ve promoted my book. I wasn’t sure which option I’d go for–it partly depended on which was easier to set up. I’d need to do some research into scheduling and event software, and I couldn’t do that in advance.

It seemed like a sound strategy. I looked at it as a math problem. If I could get several thousand page views on my blog post, I could probably get 100 people to sign up for the mailing list. From that, it seemed reasonable that I could sell four to six seats or coaching sessions for $20 to $30.

seats thumb Craziest Entrepreneur Challenge: Can 3 Devs Make $100 Each In 24 Hours? (1 of 3)

The entire day was going to be an exercise in creative prioritization and creating and shipping things just in time. Here’s how I envisioned the day unfolding:

  • 5:00 – 7 a.m. — Research blog post format. Outline and write post. Set up mailing list subscription form.
  • 7:00 a.m. — Publish post. Post link on Hacker News.
  • 7:00 a.m. – 12:00 p.m. — Promote post via email, Twitter.
  • 1:00 p.m. – 3:00 p.m. — Decide on product format. Write sales page.
  • 3:00 p.m. – 5:00 p.m. — Create list signup giveaway. Write and send welcome email, including giveaway and event promotion. Schedule welcome email to go out automatically to new subscribers.
  • 7:00 p.m. – 9:00 p.m. — Find additional ways to promote blog post. Try to sell event or coaching slots directly to friends and acquaintances.

My confidence started to ebb as December 17 got closer

Instead of looking forward to the contest, I started to dread it.

There were two main sources to this stress. One was the reason why I hadn’t already written this blog post, and the other was a fundamental fear that most humans suffer from.

As I mentioned earlier, this blog post idea had sat in on my to-do list for months. I’d resisted acting on it even though I knew it would be a hit. Why the reluctance to do something I knew would be good for my business?

The very thought of publishing this post made me feel like fraud. While I’ve had some modest successes with my marketing efforts, there are a lot of people out there who know a lot more about the topic than I do. I’ve learned most of what I know from sources like Amy Hoy’s 30×500 class and blog posts from guys like Nathan Barry and Pat Flynn. I was afraid of what these marketing vets would think. Would they just laugh at me and leave sarcastic comments?

Then there was another terrifying possibility: If my post did well and I sold a few seats, I’d have to gulp speak to a group of people—and purport to know what I was talking about. And for me (as with most breathing humans), public speaking ranks up there with swan diving into a pit of rattlesnakes.

The fear intensified with each passing day. I knew I had a shot at winning this contest, but by the time I went to bed on December 16, I wasn’t sure I wanted to.

Up next

In the next post in this series, you’ll hear from each of us how each of our days actually went.  So, stay tuned.  Subscribe here if you don’t want to miss the updates.

1 Million Dollars to Succeed

Let me ask you a question.

How would you develop your next software project if I told you that if you “succeeded” you would be given $1 million dollars, but if you failed you would get nothing?

money thumb 1 Million Dollars to Succeed

Success of course is a very fuzzy term, but let’s assume that success means:

  1. You built a working functional product
  2. Your customers are happy with it, content enough to call it done
  3. You delivered it on time
  4. You delivered it within budget
  5. It can be fairly easily modified and maintained with its current design for the next 5 years.

This is an all or nothing proposition.  Everything is on the line.  If you were to succeed, you would be rewarded handsomely, but if you fail, your effort would be entirely wasted.

Oh, also, you can’t work more than 8 hours a day 5 days a week—no winning by heroics alone.

Why ask this question?

Simple, because after thinking about “how to build software” for the last 10 or so years, (in my beginning years, I didn’t really ponder this question) I have decided the answer to this question is the way that software should be built.

I don’t mean that developers should be given an all or nothing proposition.  What I mean is that we should be building and designing software as if I proposed the above situation.

This might sound a bit crazy, but think about it for a bit.

Most developers today are paid a salary.  Some salaries have bonuses attached for performance, but rarely are we put in a situation where making mistakes or not being as efficient as possible results in dire consequences.  The worst that can happen in most cases is that we would get paid for the work we did and then be looking for a new job at the end of the project.

Losing all the time we put into the project and losing out on an opportunity to make a million dollars would be some consequence.

We’d think about software development quite differently

think thumb 1 Million Dollars to Succeed

It’s really hard for me to answer the question of whether or not practices like TDD are worth it.  I mean sure, I tell my manager it is.  I emphasize quality over speed.  I say we need to do this or that, but honestly I don’t really know.

I’ve never been put to the test.

No one has ever said to me, “succeed or die.”

No one has ever put the consequences of my choices directly in my own hands.

Never have I actually had to weigh the weight of extra time spent refactoring code, writing unit tests or using an ORM instead of writing SQL directly in my source code.

I choose technologies because they seem good to me or it seems like they’ll help me get things done faster, but I am never really staking much on that choice.

Sure, I may be staking my reputation, or I might lose my job, but chances are I’ll just blame some failure on some other reason or worse yet, I won’t even recognize my failure, because it will be disguised by “good enough.”

“Man, John, you are a big fraudulent a-hole!  I can’t believe you go around touting to know stuff, leading people down paths that you yourself don’t even know are correct.  Burning up other people’s money in your test lab of software development.”

Maybe it’s true.  Maybe I am a big ignorant and arrogant jerk, but somehow I feel that I am not alone.

I’m not saying we don’t or shouldn’t have strong convictions.

I’m not saying that we don’t have good reason to believe the development methodologies and practices we suggest and follow are correct.

What I am saying is…

Our beliefs about software development are mostly theoretical

theory thumb 1 Million Dollars to Succeed

8 years ago I would have told you that you needed to create UML diagrams before you write any code.

5 years ago I would have probably emphasized the importance of always having an XML schema.  I would have told you data without schema is meaningless.

I don’t hold either of those views today.

Perhaps you’ve changed your views in the past few years as well?

The point is that even though we may be down in the trenches doing software development and to some degree finding out what works and what doesn’t, we are basing the results on OUR motivations not the motivations of our customers or our employers.

So, we may eventually get good at making things easier for ourselves, but unless your feet are held to the fire, you’ll never really optimize for building the best software as efficiently as possible.

If you think you already are focusing on building the best software as efficiently as possible and I am just full of crap and you don’t operate that way, I would strongly suggest doing a thorough self-check and also please tell me the secret of the most efficient way to build software, because I definitely want to know.

What about startups or open source projects?

You might be tempted to think that working for yourself or not for money at all would change things, but I’m really not sure that is the case.

I’ve worked on plenty of my own software projects where my fate was directly in my hands.

I’ve built applications like PaceMaker where my financial success with the endeavor was directly tied my own efforts and my efforts alone.

But, do I think I built PaceMaker as efficiently as possible?

No, definitely not!

The problem with PaceMaker and other projects where there is a big potential upside, is that the upside potential is not guaranteed.

I can assure you that if someone said to me that I have 6 months to build PaceMaker and if I succeeded (according to the rules I stated above) that I would be given $1 million dollars, but if I failed I would be given nothing, I would have probably gone about the whole process an entirely different way.

I’m not saying I would have built it with perfect efficiency, but my motivations would have entirely matched up with the footprint of building software as perfectly as possible.

What I mean by this is that I would be trying as hard as I could to do what I absolutely believed was mostly likely to benefit me, and by doing so I would be trying as hard as possible to completely optimize the process of building that software.

What can we do about this?

Now I can’t tell you how I would have built PaceMaker had I been given the million dollar challenge.

There is no way that I could objectively put myself into that situation and give you an answer.

Would I have bothered with unit tests?  Would I have have created backlogs and written UATs to make sure they pass?  Would I have used an IoC container?

The plain and honest answer is, I don’t know.  All I know is that I would have done things differently and on any software project you’ve worked on, you probably would also.

There are a few things we can gather from thinking about this hypothetical proposition.

  • Don’t think you know the answer, but at the same time have convictions about what you currently believe.  Just hold on to those convictions loosely.
  • Even though you can’t realistically be completely objective and build software as if someone was going to pay you 1 million dollars (just like you can’t tickle yourself) you can still try to think as much as possible with this mindset.  It is a worthwhile exercise to imagine as if the decisions you are making and the convictions you are holding onto are based on idealism or reality.  We could also all examine and at least understand our own motivations.
  • Recognize others are in the exact same boat you are.  Don’t believe everything an expert says or even believe there are experts.  Experience and wisdom count for something, but no one has anywhere close to all the answers.

I’d love to see this experiment actually played out.  I’d really be curious to see what the outcome was, especially in a team situation.

Perhaps someday, someone will actually conduct this experiment and share the results.

What about you?  How do you think being given the million dollar challenge would change the way you develop software?