My 2016 Year In Review: From zero to profitable

University of Florida College of Engineering Interview Preparation Workshop

In September 2015, I quit my job (again) to publish Fearless Salary Negotiation and start bootstrapping a business. So the one-sentence summary for 2015 would’ve been: Write and publish my book.

My one-sentence summary for 2016 is: Build infrastructure to turn the book into a business.

As usual, this is a long post, so here’s a table of contents in case there’s something you want to jump to:

Here we go!

How did I do in 2016?

For 2016, I thought I would just publish the book, build some products to augment the book (video courses), ramp up to enough revenue to cover all my bills and then return my focus to TaskBook. I hoped to do that early in 2016.

If you’ve built a business, you know how silly this plan was, especially considering I was more or less starting from scratch. Yes, I had published a book. But that was it. I had something like 700 people on my mailing list when I launched the book, and somehow I thought I was heading to enough monthly revenue to pay all my bills from digital products early in 2016? Who was going to buy all these products?

On average, I made about half of what I would’ve needed to pay all my bills in 2016. That’s the bad news. The good news is that I finished the year on a five-month stretch of basically paying all my personal and business expenses. So it took me almost a year, but I am paying my bills, and my business is profitable.

Of course, the ultimate goal is to make multiples of my previous day-job salary. But that’s going to take a while, so I need smaller goals in between. The first one was “Pay all my bills”. The next one is “Make a decent living”.

What I now realize is that 2016 was another foundational year. If 2015 was “Write and publish my book.”, then 2016 was: Build infrastructure to turn the book into a business.

Looking ahead to 2017

For 2017 I have a more strategic focus, supported by tactics, to build on the infrastructure I created in 2016.

It feels like this is the difference between working in the business and working on the business. I’m not exactly sure what that means, but I think that’s what’s going on. I’m moving out one level from working in the business—building products, building a web site—to working on it by growing it.

Fewer new products, more new sales

I’ve built a lot of great things in 2016, and now it’s time to grow my business and revenue. Building new products is extremely challenging and time consuming. But now that those things are built, I can reallocate that time to growing my business.

So I don’t plan to create many products in 2017, and will turn my focus to finding my niche and finding the right customers to benefit from the products I have built. I’m sure I’ll build something new, but I’m planning to resist the urge to make make make.

Focus on helping software developers

I think “the right customers” for my business are software developers. I like working with devs and they are generally positioned to gain a lot from my expertise. In many ways 2016 was just a series of experiments with different markets, and every time I worked with devs, or made something specifically for devs, the response was tremendous. For example, this article on How software developers can get a raise without changing jobs has been viewed over 30,000 times so far.

It’s pretty obvious that this is where I should focus, so that’s what I’ll do in 2017.

More traffic (continued)

By the end of 2017, I would like to have 100,000 visits from organic search per month. That’s about 15 times what I’m getting right now. There was a time when this goal would’ve seemed totally unattainable, but I know what I need to do, and I just need to execute.

The problem with this goal is that much of this is out of my control. An algorithm change or something else could wipe me out. The good news is that if I do the right things to drive this number, lots of other numbers will improve. As I’ll talk about in my detailed recap below, organic traffic has been a lagging indicator that I’m doing the right things, and I’m really interested in this stat as a proxy for other things going well. If those things go well and this stat tanks, then so be it.

What’s interesting is I have no idea if this is a stretch goal, or low-hanging fruit. One one hand, 100,000 organic visits per month seems like a huge number. On the other hand, I’ve consistently tripled organic traffic every 60 days for a year. I don’t think that’s sustainable, but I also didn’t think it was sustainable a few months ago and here I am.

If I keep up that pace (again, it sure seems like this is totally unsustainable), I’ll hit 100,000 organic monthly visits in July or August 2017—plenty of time to spare.

Make a decent living

I’m basically breaking even right now—my savings account is no longer shrinking, but it’s also not growing. And I’m living very lean to make that happen. “Make a decent living” would mean replacing about half of my previous day job income, starting to re-grow my savings account, and opening up my personal budget a little bit.

I’m not really swinging for the fences here, but that’s because I’ve learned that this is likely to be a slow, steady grind forward. Hopefully I blow this goal out of the water, but I’m not counting on it. Maybe “Make good money” will be a goal for 2018.

Finally finish my audiobook

I managed to re-record about 70% of my audiobook after learning some tough lessons earlier this year, but then I ran out of steam. I would like to get this project finished, and I’m hoping to get back to it early in 2017. We’ll see.

A detailed 2016 Year In Review

Here’s a look back at what I built in 2016.

Products and services

Most of these things are new things I built in 2016. Plus there’s a TaskBook update for those who are curious.

Video courses

I started the year by building video courses to accompany Fearless Salary Negotiation. I know a lot of people learn visually and need action items and next steps, and I wanted to give them a way to learn and apply my strategies and tactics.

This was the hardest part of 2016 by far. Not only did I have to create all the content (about 400 slides, each one scripted word-for-word), but I had to learn how to record and edit audio, video and screencasts. Meanwhile, my monthly revenue was close to zero and I had to spend about $2,000 on my car.

It took me about 10 weeks of non-stop work, but I got everything done and I’m very happy with the result. The result is over three hours of quality screencasts that augment the book and visually illustrate key concepts so they’re easier to understand and use.

I started out here on Once I picked a title for my book, I registered and published a few sales pages, but I still kept writing and pointing everything to

In March this year, I realized that Fearless Salary Negotiation was its own brand and that I needed to start treating it that way. So I redesigned the site, moved to a new platform, and started publishing new content there. At the time, had about 10 pages total. Now it has over 150 pages, and I’ve built every single one.

About 60 of those pages are the online version of the book. The rest are a mix of articles, landing pages, and sales pages.


I’ve been coaching people since I started writing my book because I needed to know exactly what was happening in interviews, salary negotiations, and raise and promotion discussions. At first I didn’t charge anything and I worked with friends and family, then friends of friends. I did that for over a year.

Then I got a call from a friend who said, “I have a big job opportunity and I don’t want to mess up this negotiation. What’s your consulting rate?” I…didn’t have a rate, but I knew she was a freelancer, so I said, “Whatever your rate is.” She charged $75 an hour, so that’s what I charged. Then another friend reached out and since my first client didn’t flinch, I charged $120 an hour. Again, no hesitation, so I knew I needed to raise my rate again.

Fortunately, I went to BaconBiz Conf during this $120/hr engagement, and I talked to my pals Josh Kaufman and Jim Gay. I was pretty proud of myself for getting up to $120 an hour and planning to “Charge more!”, but they had other ideas:

“Why are you charging hourly?”

After a 30-minute conversation, I was planning to charge $1,500 for a fixed-fee engagement with a money-back guarantee. I would promise to increase my clients’ base salary by at least $10,000, so this would be a slam dunk ROI calculation.

Looking back, I’m not sure I actually believed I could find clients who would pay me $1,500 to coach them. (This was classic Imposter Syndrome at work.) Sure, I had made people tens of thousands of dollars. Sure, I knew what I was doing and my previous clients (paid and pro bono) had loved working with me. But would strangers really pay me $1,500 to help them bump their salary by $10,000?

You bet they would! But they didn’t much care about the $10,000 promise and I think it actually worked against me early on. $10,000 is a lot of money to some people, but it’s not much money to other people. For those other people, a $10,000 promise just wasn’t compelling (if you’re making $150,000 a year and I promise to help you get to $160,000…that’s not an exceptional jump for you). So I dropped the $10k promise and stuck with the money-back guarantee.

Since then, I’ve worked with folks negotiating at Google, Amazon, Tesla, Samsung, Verizon, and other companies you’ve heard of. And I’ve raised my rate to $2,000 with a plan to raise it again soon.

I was obviously nervous about offering a money-back guarantee, so I mitigate this risk by holding the money aside until my client tells me they’re satisfied. But so far, none of my clients have asked for a refund. (I’m sure this will happen eventually—it’s just a part of doing business. But it’s nice to have a perfect record in 2016.)

My coaching offering has been a huge boon to my business this year. About one-third of my revenue was from coaching.

The Interview Cheat Sheet

Initially, I made The Interview Cheat Sheet for my coaching clients. I found that I always gave them the same homework before their job interviews, so I figured I would make a nice cheat sheet for them. I hadn’t launched any tiny products, so this was a good chance to try that.

It only made a few hundred dollars, but that was just gravy since I made it for my coaching clients anyway. And now I include it with all my eBook and video course bundles as well.

Get Your Next Raise

Any time someone buys Fearless Salary Negotiation, I ask them “Are you negotiating an offer for a new job or looking to increase your salary at your current job?” The responses are pretty evenly split.

Then I ask some followup questions to see where they might be stuck. I found that I had a really good offering for people who were stuck on interviewing and negotiating and wanted more help from me, but I didn’t have much to offer for those who were hoping for a raise.

So I built Get Your Next Raise. It’s a pretty unique self-paced and guided course that walks students through step-by-step process to ask for a raise while I get them feedback along the way. I launched it at the end of November and I plan to promote it heavily in 2017.

This is also the first product I have built by working backwards from the specific need I saw to a solution (the course) to a free offering that offers value and helps potential students determine if the course is right for them.

Shutting down TaskBook

I’ve decided to focus 100% of my time and energy on growing my business around Fearless Salary Negotiation, which means I’m sunsetting TaskBook in 2017. This is tough because I still have people reaching out who say, “Why can’t I sign up for TaskBook?”, and I know it would help them. But I simply don’t have the resources to grow two businesses.

There’s an alternate timeline where my first big project is Fearless Salary Negotiation, and it fizzles out because I don’t know how to sell or market. Then I take what I learned and build TaskBook, which takes off like a rocket. But instead, I started with a SaaS (pro tip: Don’t do this!), didn’t know how to find customers, and got distracted by a shiny new thing, which is growing into a business.


I mentioned this was a foundational year, and I think that will show through in this section. Here are my high-level stats from 2016.

My email list

A big metric for businesses like mine is “How many subscribers do you have on your list?”

  • December 2015: ~700
  • December 2016: ~2,500

That’s a decent growth rate considering I haven’t done any meaningful paid acquisition (Facebook ads, etc.). One thing I need to work on is learning more about what folks need when they join my list or download a free guide from me. And I need to provide more value and build a better connection with everyone on my list.

In September, switched to a new Email Service Provider (ESP) called Drip. ConvertKit was great for getting from zero to almost 2,000 subscribers. But as I tried to do more with my list, engage more effectively, learn about people, I kept bumping into limitations. Drip seemed like the best way to get to the next level, so I switched. To ConvertKit’s credit, many of the things that I left for are starting to show up in their product, so it seems I was just a few months ahead of them.


After BaconBiz Conf, I spent an extra day in Philly. I decided to walk to a little coffee shop and found myself crashing a post-conference work session attended by many of the conference’s speakers (many of whom are already my friends). Not one to let a good opportunity go to waste, I coaxed a little advice from the group (this was not difficult), and the main message was:

You’re doing the right things, you just need to do more of them and get more traffic.

At the time, I really didn’t know what that meant, but I started doing things I thought would help. I was already doing a podcast tour, inspired by Kai Davis among others, and had begun looking for opportunities to write guest blog posts. (See a summary of my podcast appearances and guest posts here.)

I also began writing and promoting more content at so I would have more content to point people to when they asked questions, and so Google would have a greater surface area of things to find and suggest for search queries.

My focus has been on Organic traffic (when people Google things and click through to find the answer) because I think that’s a lagging indicator of all other types of traffic. If I get lots of traction with my content, podcasts, guest posts, social media, etc., that will eventually translate into Organic traffic.

Here’s my 2016 weekly organic traffic:

2016 weekly organic traffic on

As you can see, it’s growing pretty steadily and quickly. I have basically tripled traffic every 60 days this year, so I went from almost zero traffic in January to almost 2,000 visits a week now.

Book sales

I’ve sold almost 1,200 copies of Fearless Salary Negotiation so far. Most of those sales were on Amazon, which is why I launched on Amazon. One cool thing is that I have steadily raised my price and sales continue to improve. So I’m making more sales and getting more revenue per sale. This has been a nice surprise.

One concern I had about launching and selling on Amazon was “You don’t know who your customers are!” (this is a common thing I hear in the self-publishing community). This is partially true—I technically don’t know who buys my book because Amazon doesn’t tell me.

But! 10–15% of Amazon buyers subscribe to my email list because I point back to my site, where I offer free worksheets and email templates to accompany the book. Some of those folks have eventually become coaching clients, so I see the Amazon version of my book as a sort of combo product/marketing tool/calling card.


I worked with about a dozen different clients this year. Not bad considering I didn’t launch my coaching offering until mid-year. I’ve intentionally grown this part of the business slowly because I want to make sure my clients get great value for the price, and because I wanted to iterate on the offering as I got to know more clients.

I’ve found that the folks who benefit the most from working with me are experienced software developers moving to larger companies like Amazon, Google, and Tesla, so that’s who I’ve been working with lately.


University of Florida College of Engineering

I had a chance to do about 10 talks this year, and they were a lot of fun. As I write this, I realize that all but one of those talks were to engineers or software developers—another sign that focusing my efforts on helping software developers is a good idea.

This talk on salary negotiation for software developers for Orlando Devs and The Iron Yard, Orlando was my first of the year and it has almost 7,000 views on YouTube. I also gave several talks at a local code school called Gainesville Dev Academy, where they buy a copy of my paperback for every student.

The really fun thing is that talks are easy for me to do—I’m extremely comfortable with public speaking. And they give me a chance to meet developers and see what they’re struggling with.

Podcasts, webinars, quotes, and guest posts

Here’s a one-page summary of my podcast appearances, webinars, quotes, and guest posts.

I was on more than 20 podcasts this year. Most of them were software developer podcasts (yes yes, another checkmark for “focus on helping software developers”), and the response was fantastic.

I think the highlight for me was talking with my pal Patrick McKenzie on his Kalzumeus podcast. Patrick’s detailed blog post Salary Negotiation: Make More Money, Be More Valued was an early inspiration for me to learn more about salary negotiation, try it for myself, and eventually write Fearless Salary Negotiation.

I also participated in three or four webinars, which was great practice. I’m extremely comfortable in the podcast format (probably more comfortable than public speaking), but not as comfortable with webinars where I sometimes need to be on camera, and where the audience is live but invisible.

I did four guest posts and was quoted in a article, so that’s pretty nifty.


I’ve decided not to share my revenue numbers publicly because there are some drawbacks and I can’t think of any real benefits.

That said, I’m basically paying all of my personal and business expenses each month. That’s a big deal for me because it means I’m not spending my savings anymore. Hopefully in 2017 I can replenish the savings I burned through earlier this year.

Wrapping up 2016

It was a good year. It started slow and stressful, but things turned around mid-year and most of the important graphs are moving up and to the right.

I am learning a lot about building and running a business—this experience is invaluable. I’ve spent the past several years getting to know some very smart people, and their guidance has helped me keep focused on the right things and ignore the things that don’t matter.

I’m really looking forward to seeing how this business grows in 2017.

Why I cut my 2014 WSOP trip short

NOTE: I wrote the first draft of this on Sunday morning, July 6.

I’m in Atlanta, waiting on my 8:00 AM connecting flight back to Gainesville. It’s been a while since I took a redeye, but this is the real deal. I took this flight because I didn’t have many other options when I decided to cut my annual WSOP trip to Vegas short.

Why did I do that? To be honest, I’m really not sure, and I’m processing that question as I write this. I was really excited to head out this year, and I’d been looking forward to it since I returned from last summer’s trip. So I packed my bags, flew to Vegas, and immediately just felt… off. Instead of looking forward to playing tournaments, I sort of dreaded it. I was there for three days before I played my first tournament (the $1,500 Monster Stack, where I hung out for 10 hours and busted at the end of Day 1). It was another four days before I played my second tournament (a $300 tourney at the Wynn, where I busted on a bad beat after about four hours).

After playing only two tournaments in a week, I thought the remaining 11 days of my vacation could be better spent than puttering around Vegas, playing a tournament every few days. I decided I would rather spend my final week off in Gainesville, where I can relax and work on TaskBook. So here I am.

But I can’t help but wonder if there’s a little more to it. I’ve been playing poker for 11 years, and I was really, really fascinated by it when I began playing in little home games in college. I was the guy who went out and bought books and started reading poker forums to get better in my five-dollar home game. When I graduated from college, moved to Dallas, and started working full-time, I also started playing a lot of poker online at night after work.

I played a lot and read a lot, but I never went all-in the way some online pros and grinders did. I just didn’t have the will or desire to grind eight to 10 hours a day online. That didn’t sound fun to me.

I continued playing a lot of poker online for the next several years, and started visiting Vegas for the WSOP beginning in 2009. A couple months after my WSOP trip in 2009, I was let go from my job and started playing a lot more online poker. I still enjoyed playing, but not nearly as much as I had when I began, and playing online started feeling like more and more of a grind. I think that’s when I began to burn out.

My poker reserves began running low late in 2009, then my online time tapered a bit through 2010 and had all but disappeared by the time Black Friday hit online poker in April of 2011. From then on, I would play the occasional cash game in Florida, but mostly just played during the summers in Vegas.

Late in 2011, I began writing Heads-Up Tournament Poker and building my first web application (ShareAppeal). Pretty much all of my poker energy went into the book, and the remainder of my creative and intellectual energy went into learning Ruby on Rails. I never really saw poker as a way to create a dependable income, but I felt differently about web applications – I felt there could really be something there for meaningful future income. I began shifting my energy and interest from poker to app development and stopped playing poker entirely except during the summers in Vegas.

My 2012 trip was a month long, but I was working full time for the entire month, so I didn’t play much poker. I almost didn’t make the trip in 2013, but was persuaded by a friend to make the trip (and I’m glad I did – that was a fun two weeks). I think my 2013 trip emptied the tank, although I didn’t realize it at the time. I didn’t play a single hand of poker between the WSOP 2013 and my trip this summer, or maybe I would’ve realized sooner that I had used up most of my interest in poker for now.

I’m not saying I’ve quit poker, or that I’m over it. I just wasn’t feeling it this summer. I’ve been working hard on TaskBook, and that takes a lot of energy and can be sort of distracting when playing poker. I see TaskBook in particular, and app development in general, as a way to generate real income on the side, and it’s still very interesting to me. Unfortunately for poker, app development uses a lot of the same creative energy as poker does, so there’s just not enough room for a deep interest in both.

I hope that I can replenish my poker-energy reserves over time. I may play some cash games around town, or jump into some Florida tournament series this fall, or I may not. But for now, I’m just not as interested in poker as I used to be, and I’m more and more interested in app development. So my guess is my energy will be focused there for a while, and poker could be on the back burner indefinitely.

I have a cool new app idea! How do I get started building it?

Why I’m writing this

“I have a cool new idea for an app! How do I get started building it?” I get some form of this question about once a month. It recently came up again over lunch with a friend who owns a small, successful business. “I have an app that we’ve been using at my business for a couple years. I think it could really be valuable to other businesses like mine, so I’ve been talking to a couple of my friends, and I think we’re going to go in together and build the app out so we can sell it as a service to other businesses.”

As we talked, I heard some really encouraging things and some red flags.


  • A few other business owners have told him they think it’s a good idea and they would be interested in learning more.
  • He already has a prototype that’s a functioning web app, so he wouldn’t be starting from scratch.
  • The app saves him a lot of money every month by almost eliminating the time needed for one aspect of his business’s customer service; it also brings in a little revenue of its own.
  • He has direct access to a good-sized target market. His particular business is very well respected in his niche, and those who respect him could benefit from this product and would take his call if he wanted to ask them to try it.

Red flags

  • He wants to bring a couple of technical people in as co-founders to start a company and build the app.
  • His background is in sales and marketing, but he has little technical expertise (someone else built the current app with his direction and input).
  • He’s already pretty busy running his current business day to day. He also owns another totally different business on the side.

After lunch, I told him I would think about his idea and email him with my thoughts. I realized I had a lot more to say about his idea and I put together a long email, hoping to help him avoid some possible pitfalls and set him up with an actionable plan in case he moves forward with his idea.

Then I realized this could really apply more generally to the question in the title of this piece. So I’m posting it here and I’ll refer future requests here as a starting point.

Here’s the email, slightly edited. I swapped out the specific function of the app for a generic term “uses” or “instances” so I don’t give too much information about my friend’s business or his app. I also edited for brevity in some spots.

The email

DISCLAIMER: I’m not a lawyer or an expert on building apps or starting businesses, or co-founding, or equity, or anything like that. If you need an expert or a lawyer, you should go find one 🙂


I looked at the app on your site, and it’s pretty cool! I’m happy to talk about this over lunch some time, but here are my general thoughts. Everything I’m saying here is from the perspective of how to build and grow a business to give yourself a good shot at success. I’m not really looking at it from the perspective of someone who just wants a challenge, or something to do with friends, or is looking for a new project.

Overall bottom line

  1. Get a rough idea of who you’re going to sell to and what you’re going to charge.
  2. Go find potential customers and see if they’re really interested. Get a commitment from them that they would pay for your product at a certain price-point. You may also want to put up a “landing page” where other potential customers can sign up for a mailing list and/or pre-order.
  3. If there’s real interest then start building it either by outsourcing or with a single technical co-founder with experience in this area.

Revenue model

Bottom line: I recommend charging monthly using a tiered model based on number of times they’ll use the app. I don’t know where the prices should land (I’m not sure how much value the app adds – more on how to figure that out below), but something like: “Up to 50 uses a month for $149/month; Up to 100 uses a month for $249; Up to 200 uses a month for $399; Up to 1,000 uses a month for $999; Call for Enterprise pricing”.

You should start thinking about this now. You may change it later, but it’s important to know how this app will actually make you money. Are you just charging customers a monthly fee to use it? If so, does every customer pay the same amount? How do you differentiate between “big” and “small” customers? Or maybe you just take a cut of premium upgrade fees and give the app to customers for free.

How to determine price: The easiest way to do this is just to figure out the value-add for a customer and price accordingly. You mentioned that you used to spend a lot of time every day for this aspect of your customer service. You could do a rough guess on how much time you save (man hours) per month with the app, then figure out what that translates into on a per-use basis for you.

Example: “We complete about 100 instances a month. My employees probably spent about 40 hours a month performing this function manually, and my cost of payroll is about $12 an hour. I don’t save all of that time because the app doesn’t replace all of the manual work, so let’s call it $400 a month in savings.” But this app also increases top line revenue, so you could add, “And we make about $100 a month from upgrades. So we’ll save total value is about $500 per month at my store.” But you have to add value – not break even – for your customers, so let’s cut the cost to the customer in half: $250/month for 100 uses.

This is just a ballpark number that you would use to build other tiers around so you have a pricing plan to show to potential customers. The reason this matters is that the next thing you need to do is…

Marketing and Customer Development

Bottom line: You should find customers before you invest the time and resources in building the product. You want to go out and find a few customers who have the pain point you’re addressing, and who are willing to pay for your solution. If possible, you want some kind of commitment that they’ll be a customer when you launch. I’d say you want at least five customers who say, “Yes, I have this need and I would be willing to pay that amount for a product that addresses this need.”

If you’re serious about building this app, you should start with Marketing and Customer Development. You should start by going out and finding customers who will pay for your product. From what you told me at lunch, this could be easy – but you won’t really know if it’s a viable (meaning – profit-generating with customers ready to buy) business idea until you have commitments from customers to give you money to use the product.

So you’ll call up some of your contacts in your own niche and ask them if you can get their feedback on a product idea you’ve been thinking of bringing to market. Show them a demo or some mockups to get their input and gauge their interest. Then ask them if they’re a customer at their estimated price-point, and ask if you can keep in touch with them via email as you move forward with the project. You want to leave the meeting with two things: 1. Some kind of commitment that they’re a customer around the price you anticipate charging them (this could range from a verbal commitment to a pre-order); 2. Some way to keep in touch with them (email, phone, etc.).

If you’re able to get five commitments or so, you’ve got a good thing going and you should think about developing the app. But first, you might want to set up a “landing page” – a one-page website with a little brochure about what you’re building, and where potential customers can sign up for a mailing list to keep up with your progress. You could market this page and continue soliciting signups as you build the app so that you have a nice mailing list to reach out to when you are ready to launch (or do a Beta or whatever). Marketing will be an ongoing activity as you develop the app, and it’s best to start early.


Bottom line: In your case, I would recommend either 0 or 1 co-founders. Since your available time to work on this is limited, it seems like you’d be best off getting one technical co-founder to manage app development (including outsourcing if you want to save time by spending more money).

Now I’m finally getting to co-founders! You’ve gotten to this step because you’ve figured out a potential revenue model for your product, and you’ve found a number of potential customers who said they would buy your product at some price. So it’s time to figure out how to bring this to market given your constraints. In your case, it seems that your constraints are primarily your available time to invest in building another business, and technical expertise. (Your strengths are that you are very comfortable running a business, and you’re an experienced Sales and Marketing guy.)

I think you should have a really, really strong business reason for bringing on co-founders. For example, if I decided to start a business tomorrow, I would be capable of owning the technical aspects of the business (technology, writing code, testing, etc.), and a lot of the business operations (cash flow, whether to hire, etc.), but I am pretty green when it comes to Marketing. If I were bringing in a co-founder, I think my blindspot is Sales and Marketing, so I would try to find someone who is very strong there. But I wouldn’t go after multiple people with that skillset – just one.

Be careful bringing on co-founders – they’re very expensive and difficult to get rid of if they don’t work out. If you give someone 25% and they work a few months and then get bored and moved to Indiana, they’re still a co-founder with 25% and that would be really unfortunate. [Digression, which I didn’t include in the email itself: You can do some smart things around vesting periods that mitigate this, but their ownership stake is only a small part as they’ll also be influencing the actual operations of the business, possibly slowing it down or derailing it, or just generally getting in the way.]

It sounds like you had a good idea, and talked to some friends, and they thought it was a good idea, so you’re all thinking of co-founding together. But you already have the idea and you had a prototype built. And, if you’ve gone through this progression the way I wrote it, you’ve already gone out yourself and found people willing to pay for your product. What you need now is technical expertise. I think it’s reasonable to find a technical co-founder, but I don’t think it’s necessary (or even useful) to have multiple technical co-founders. The difficulty in managing the business increases exponentially with more co-founders–the more you have, the harder it is to make decisions, and the more likely someone will just free-ride on your work.

Things I would look for in a technical co-founder for your idea (these aren’t all mandatory)

  • Has some level of business experience – after all, you’re co-founding a business. You want your partner(s) to know something about what that means.
  • Experience building web applications.
  • Experience with billing and payment integration into applications (you’ll be taking money and he’ll be responsible for making the app do that).
  • Experience with multi-tenant web applications (“multi-tenant” just means that the app can be used independently by multiple businesses without them seeing what the other businesses are doing).
  • Experience managing technical resources. Odds are you’ll need to outsource some of the work (although a really strong technical founder could at least build the prototype and Minimum Viable Product).

You could also do this without a technical co-founder, but it would be tough. What you would need to do is find a web app developer who could build the app as a contractor or something like that. This could be problematic for a few reasons:

  1. It might be tough for you to manage a contractor given that you aren’t experienced with app development. It’s not impossible that this could work (after all, you have a prototype), but it could be tough.
  2. Proficient web app developers are in very high demand right now, and could be both difficult to find and expensive to hire.
  3. If you want to move quickly at all, it would probably be better if your technical lead was really invested in making this product work and bringing it to market. Contractors charge by the hour and would be pretty happy to just plod along at a reasonable rate. A co-founder with equity would want to start generating revenue quickly in order to get paid.

I’m not trying to discourage you here – I know it may seem that way. I’m trying to help you maximize your chances of succeeding without running yourself into the ground. I’ve heard this methodology described over and over again, and I wish I had approached TaskBook this way.

Some resources you may find helpful

  • Most of the “get customers and signups first” stuff I am talking about is based on Nathan Barry’s book, Authority.
  • Startup For The Rest of Us is an excellent podcast on startups. I’ve listened to about 60 episodes and I’m moving through them as quickly as possible. You could scan the list of episode names for relevant topics (co-founders, customer development, etc.).
  • Amy Hoy’s blog is a great resource for bootstrappers. In particular, How do you create a product people want to buy? might be helpful to you right now.
  • Product People is a really great interview podcast where Justin Jackson asks entrepreneurs about their products and businesses. It’s a really informative, and really easy listen.

TaskBook has a new blog!

A while back, I announced TaskBook, a simple online employee checklist tool to help businesses save time and money. TaskBook is growing, and I realized that I have a lot of ideas for blog posts that could be helpful to the TaskBook community. Rather than mix TaskBook posts with my personal blog posts, I decided to create a dedicated TaskBook Blog. I’ll use the TaskBook Blog to announce new features and share tips for managing business owners.

Here are some resources where you can learn more about TaskBook and follow its progress:

I’m constantly learning new things as I continue to build TaskBook, and I may still use this blog to write about the process of building TaskBook – lessons learned, pitfalls, Ah-ha! moments – so stay tuned!

I built TaskBook, an app to help businesses save time by managing employees better


I’m really excited (ok, and kind of terrified) to announce TaskBook, an app to help businesses manage their employees’ responsibilities. It’s a checklist app that helps automate recurring task assignments so employees know what to do when they come into work.

I’ve probably said, “I’m building an app…” a thousand times this year, and I’m glad I can finally share what I’ve built.

Why a checklist app?

A couple of years ago, I started working on ShareAppeal, which is a social networking app to help us share links and build reading lists for each other and ourselves. That was a really fun project, and I still use it regularly. I worked on ShareAppeal for about a year, and then took a step back to reflect on what I made and consider where to take it next.

I decided to build something new. This time, I would make something small but really useful – something that could be helpful every day.

“What if I made an app to replace the binder?”

Some friends of mine own a bakery, and one day we were talking about the dreaded three-ring binder of checklists. I’ve since learned that this is a universal device that’s used everywhere from hair salons to restaurants to banks. Virtually every time I talk to a brick-and-mortar business owner, they know exactly what I mean when I say “the checklists” or “the binder”. (If you’re not in that world, just picture a pile of laminated paper checklists and a dry-erase marker.)

I could tell the binder was something the bakery used, but that they hated it; it was used, but not useful. It was hard to maintain, didn’t give any kind of history, and employees eventually just stopped using it because they thought they had everything memorized.

I asked my friends, “What if I made an app to replace the binder?”, and they immediately perked up and wanted to know more about what I had in mind. Over the next few months, I worked closely with my friends and their employees at the bakery to build the first prototype of the app.

I was shooting for “small”, but ended up creating something pretty big

TaskBook has come a long way since then, but the basic idea is still exactly the same as that first prototype: managers create checklists and assign them to appropriate days (“Opening tasks” is assigned pretty much every day, but since Monday is a new work week, Monday might have “Monday’s opening tasks” instead). When employees come in for a shift, they sign into TaskBook and the day’s checklists are right there, waiting for them to complete. They find the first incomplete task and start working on it. They tap the task’s checkbox to indicate it’s done, and TaskBook marks the task as complete, stamping it with the time and employee’s name. From the employee’s perspective, that’s all there is to it.

The cool part about replacing the binder with a web application is that apps record data and can be accessed from any device with an internet connection and a web browser. Changing lists becomes trivial – just a few clicks to update the list, and the new version is right there in TaskBook next time an employee signed in. Onboarding and training that used to take weeks now takes hours – at the end of a new hire’s first shift, the manager knows they’ve covered everything.

With my friends’ help, I made something much bigger than “an app to replace the binder”. It’s a simple app, but it’s not small at all – it’s had a big impact the way they run their business.

So that’s what I was talking about when I said, “I’m building an app…”

Ok, now what?

This is where things get a little scary. I’ve spent about nine months building TaskBook, and now it’s out in the wild. Businesses can sign up for a free 30-day trial and try it out to see if it helps their business like it helped my friends at the bakery. The interesting thing is, thanks to all the time I’ve spent at the bakery, I know it will help small businesses. My next challenge is to communicate how useful TaskBook can be for customers.

I spent the past few years learning to build useful apps. Now that I’ve attained my first goal, there’s another challenge right behind it: I have to learn how to sell and market TaskBook while continuing to improve it.

Now, when friends ask me what I’m up to, I’ll have to say something like, “I’m growing TaskBook.”

How you can learn more about TaskBook and follow its progress

Here’s how you can learn more about TaskBook, and keep tabs on its progress:

TaskBook Homepage
More about how TaskBook has changed my friends’ bakery
Sign up for a free TaskBook trial
Like TaskBook on Facebook
or follow TaskBook on Twitter

If you have questions about TaskBook, you can leave a comment, or reach out to me on Twitter: @JoshDoody.