Monthly Archives: January 2016

2015 Year in Review

I can’t believe that today is the last day of January in the year 2016! It’s been a whirlwind of activity and typically I’ve written this type of post within the first week of the new year (as you can see here for 2012, 2013, and 2014).

And as I sit here I just can’t seem to figure out where to start; all I know is that I feel compelled to get this post out of the door before we hit February. Where does one start when they don’t know where to start?

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Becoming a Real Startup — On Growing & Turning an Idea into Something Tangible, Fast.

Run, Forest, Run.

When I decided to start down the path of building a new company there were only a few things that I was absolutely sure about, the first being the gist of the problem that I wanted to desperately solve and second that I need to test my hypothesis as quickly as humanly possible.

My motivation was simple: If I couldn’t prove my idea quickly (or with a reasonable and justifiable amount of real data) then I’d better go find something else to do with myself (I’m not a fan of wasting my time or anyone else’s time). In addition, I’m only interested in building a legit startup which is easily defined as a new venture that grows quickly.

As Paul Graham has stated simply:

A startup is a company designed to grow fast. Being newly founded does not in itself make a company a startup. Nor is it necessary for a startup to work on technology, or take venture funding, or have some sort of “exit.” The only essential thing is growth. Everything else we associate with startups follows from growth.

Consequently, with that in mind, I embarked to build this new company with speed. And, by “company” it had to, by definition, be a venture that could sell a needed product to a large market and that would be able to reach that market with velocity (again, per Graham’s thoughts).

This is why I began building a ton of velocity in the first 72-hours because how else do you build a company, fast? Well, you build it fast, as fast as you possibly can. You sprint. And then you go faster.

So, how have we done so far? Well, I’m super-happy to share that we’ve been pulling some Usain Bolt-type of speed.

Let’s get to it.

Making It Count: The First 20 Days

As I write this it is 20 days exactly when I first began laying the foundation of what I hoped would become a legitimate startup.

As you can see below, I registered the .com domain name and my purchase receipt hit my inbox on January 9th, 2016:

[An aside: I am still floored that I get to do what I get to do — if you take a moment and step back and see all of the amazing tools that one can use (on the cheap) to build something significant, it just takes your breath away. For a mere $14.90 I can buy some space on the web and lay the foundation for what could be (eventually) a billion dollar company — and that every other technology entrepreneur started in exactly the same place. Un-freakin-real.]

As I’ve already shared, the next 3 days were a whirlwind of activity as I put together the basic building blocks of what I believed could become so much bigger than just another idea stuck in my head.

In addition to executing the very tactical points of business building I began to create some top-level strategy of how I wanted this to play out, pinging more than a handful of friends, colleagues, and family letting them know that I had, again, begun to spin up another venture.

Naturally, I wanted them to be in the know but more importantly (and somewhat selfishly), I wanted their support, their prayers, and a ton of encouragement because building a company is mind-blowing in difficulty. After having put together a company (or two) previously I was familiar with the high-highs and the low-lows and how the low-lows are, well… let’s just say that it can feel like death. I needed all the help I could get!

You see, I believe that your support network is going to be, at times, the only thing that is going to help you get through those really tough uphill climbs and the deep valleys of disappointment. I believe that the stronger your network that you have is the more likely you’ll be able to succeed — just a hunch (and speaking from a bit of experience).

But I needed more than just a few people on the sidelines rooting for me, I needed to put together a team that could kick some serious ass.

Nothing like a fantastic team all headed in the same direction. See what I did there…

Getting The Band Together

My last handful of companies were comprised of an all-star cast of players and the result was telling — we were able to achieve vastly more than we thought we could in a surprising amount of time.

Sadly, it took me quite a while when I first started down the path of entrepreneurship to realize the importance of a team and how fundamental it would be to my own and the collective success of the organization. It’s not that I believed that being a “solo founder” was something that I aspired to be but it was more about control than anything else — as an engineer it was just baked into me.

My first few projects (and acquisitions) were as a solo founder and the velocity, although good, wasn’t stellar — in other words, not “real” startup-type stuff. I was just fortunate to have just enough speed to be attractive enough to sell them the project to someone. What’s fascinating is that I continued to succeed in greater ways the more control I gave up in the early stages of company creation.

This model, most simply understood, is this: There was a direct relationship between the speed of which I grew my companies, the size of the liquidity event that eventually transpired, and the size of the founding team:

Great Team + Great Idea = A Lot of Speed

A quick trip down memory lane as a Co-Founder:

The Iron Yard (acquired by Fortune 300 in 2015), A&I (acquired in 2014), SoChurch, 8BIT (acquired in 2013)

(I just noticed that I had the same glasses in every single picture here…)

A pretty astonishing 3 of the last 4 companies ended in an acquisition when I had partners and co-founders. If you compare that with the extremely long list of solo projects that I attempted to put together by myself, well, let’s just say that they didn’t end up in nearly the same place.

Consequently, I can’t imagine putting together a company by myself since the odds are clearly stacked in the favor of team structure from the beginning. It’s not that solo founding is a bad idea, it’s just not the startup game that I play anymore.

With TOMO it would be the same and my goal in the very short-term was to build a team that would help me put this project together. I immediately set out to connect to everyone in my network — talented engineers, operators, and past business partners to see who was available and ready to tackle something big.

The challenge of trying to find amazing people to start a company with is that most of those amazing people are already tied up with another amazing opportunity or they’re already busy hacking away on their own venture.

But, sometimes you get really lucky on the timing and one of your friends are ready to jump in head-first. And “luck” is a pretty big part of startup world (although a good friend of mine once told me that “Making your own luck” is vastly better).

Billy Boozer, a friend who also hailed from Atlanta, was that guy. We first met at a WordPress conference that one of my previous startups was putting together (WC Atlanta 2012) and had been swimming in the same virtual circles for a long-time and had a number of concentric relationships in the web development, engineering, and design field.

We shared a deep and abiding love for all things open source and both believed that it was a fundamental part of the web’s future. We had both built a few companies and Billy had even built a fully-scaled out HR / hiring product used by thousands of users in some large 500+ employee companies.

The timing couldn’t be more perfect as we had both exited from our previous projects and were still hungry to explore the intersection of open source and human capital.

OMG. So ugly.

A few late nights of programming and we had an extremely CRUD prototype built and I knew that I had found my co-founder. Since we were both engineers and product guys we could move with an incredible amount of speed and the division of labor on the other parts of business building we also equal in scope and ability.

I also started putting together other parts of our team, from business and technical advisors to capitalizing on passionate volunteers with specific and relevant tactical expertise. I asked them to join a Slack Team and do daily stand-ups as we continued to push hard to a prototype delivery date.

Within the first 20 days I had a team of 6 all hell-bent on creating a ton of velocity and momentum. With a small bit of leadership and a lot of heart we began to push the giant boulder up the proverbial mountain.

And when by pushing I mean we were sprinting while pushing.

Lining the Customers Up

It’s not enough that you build a great product — you have to have customers to sell it to. In a very timely post in the Wall Street Journal, Jessica Livingston tells it straight about how to get a startup off the ground:

… you should be talking to a small number of users who are seriously interested in what you’re making… we advise most startups to begin by seeking out some core group of early adopters and then engaging with individual users to convince them to sign up.

So in addition to building a prototype that would pass snuff we had to also get really interested people to help take it out for a spin. How’d we do that in addition to building a world-class product?

You hustle the fuck out of it — remember, we had to be relentlessly resourceful and just get that junk done. We accomplished this in 3 distinct and effective ways:

1. Our Employee Onboarding Survey

When I put the landing page and survey (you can still take it!) up on the website within the first 72 hours I had a follow-up email auto-sent out to those that complete the form to ask if they wanted to be part of a potential “beta” or “prototype” testing group.

The email looks liked this:

Again, with Typeform this was easy to setup and was immediate. We instantly started getting people signing up to our email newsletter (powered by MailChimp).

This was how we got the first group of prototype testers (and continue to do s0).

The next tactic was content.

We’ve loved using for our hosted solution.

2. Content Marketing Like What

The second strategy for us was to go hard with content marketing through our new blog. I have a distinct advantage in that I’ve been blogging for 15 years every single day and do not struggle as much as most people with creating content.

(To be honest, the real advantage here is that I just have a lot of muscle memory and so I can put that to good use with a decent pair of headphones and some killer tunes.)

I knew that building a company in the HR and PeopleOps space would not be an easy win for us and that we’d have to attack the industry and market through a number of different channels (and we wouldn’t be sure of our success until we tried every single one).

Indiana knows best.

Content would be a way for us to bring a metaphorical “gun to a knife fight” since it was an in-house superpower that we could leverage that many of our competitors (and especially those in the startup phase) wouldn’t be able to compete easily with.

So by writing compelling, long-form content twice a week we could begin to build some significant traction where it didn’t originally exist, pointing people to our survey, our landing page, our social media accounts as well as our other digital outposts.

But more specifically and explicitly, I asked people to “drop me an email” if they were interested in testing out a prototype:

We got a handful of very interested people to send these emails over and we gathered them, answered the questions they had, and then lined them up for trials when the prototype was ready.

Oh, and the effectiveness of our content has been amazing as all of our social media properties have grown and we’ve even had some amazing retweets via Twitter that have given us a ton of exposure over a very short amount of time with over 7,000 views, 3,500 reads, and a solid 250 recommends — take a look:

A very modest but encouraging report considering that our little project didn’t exist a mere 3 weeks ago!

3. Doing Things That Don’t Scale: Real Convos & Research

The final thing was simply doing everything that we possibly could do to get the word out which included a ton of things that simply do not scale:

The most common unscalable thing founders have to do at the start is to recruit users manually. Nearly all startups have to. You can’t wait for users to come to you. You have to go out and get them.

This meant that the team would hit up a ton of our relationships and connections and simply ask them if they would sit with us and hear our story and give us honest feedback on our concept.

And, at the same time, see if they were interested in becoming part of the prototype group that would take our insanely taped-together tool for a spin.

It’s important to note that this was some of the most important expenditure of our time in the last 20 days as we received feedback that we could never buy from people who gave us their candid thoughts about what we were trying to achieve.

I’ll admit, some of the chats were gut-wrenching and painful. Some of the conversations were nauseating, not because they didn’t see a need for what we were building but because my ability to communicate effectively was being tested in real-time, and, in the beginning my “pitch” was pretty bad; like scratch-your-nails-against-a-chalkboard bad.

The sum total of our efforts paid off big-time though! And so grinning and bearing the fury that is honest people’s feedback was well worth the personal shame that I had to endure. For instance…:

  1. We were overwhelmed with the responses from the survey and in our real-time chats that the problem we were attempting to solve and the solution that we were creating was desperately needed, TODAY.
  2. We learned that people would be willing to pay immediately for a solution that provided even a marginally-better experience.
  3. We learned that our core hypotheses about existing solutions were, in fact, correct — people were “solving” their new employee onboarding needs in disparate ways with no cohesion and no canonical source.
  4. We learned that people understood the fiscal costs of poor employee onboarding but were unsure of how to triage the financial decay.
  5. We also found people willing to be part of the prototype group and that were so excited with the possibility that they told us they’d tell everyone about it if it worked:


These were the types of things that we were hoping for and all of those lunch meetings, super-early morning coffee dates, and one-on-one phone chats were paying the dividends that we needed to have so that we could continue our momentum forward.

Besides doing the market research in unscalable ways we also tackled building the product in ways that weren’t scalable, from manually creating entries into our DNS zone files to spinning up individual Heroku instances for each prototype user.

Gotta do what you gotta do.

Everything is manual at this stage in the venture and automation isn’t even part of the equation, which is fine, because at this point we are trying to build as much velocity as we can, even if it is relatively duck-taped together.

No shame in this game. If the concept proves to be solid and the feedback positive then we’ll rebuild the entire thing anyway (now, with automation!). We’ll get there in no time.

In summation, with these 3 large pieces in play, together, we were able to build out an awesome testing group that we promised to deliver today, in their hot little hands, so that we could begin to get some serious feedback about our concept, and learn a ton about where we should continue to head as a product and company.

We have, as it stands, 16 organizations signed up to test ranging from 2 employees to over 500! If every single employee of these 16 companies participated in our prototype then we’d have over 1,800 users:

You see, when I first started this project I wanted this to be a real startup, one that exemplified true growth with an incredible amount of velocity. I’m not creating a lifestyle business or one that just grows at a steady clip — I’m building a company that reaches hyper-speed as soon as it can and to do that I have to sprint this marathon as hard as I possibly can.

And, of course, I have to find people who are willing, able, and excited to run that race, at that speed, with me.

Putting it all together.

With Our Powers Combined

So, in the last 20 days, I’ve been blessed and fortunate to be able to assemble a passionate team around an incredible and worthwhile mission with values that we believe and operate in while solving a legitimate, felt problem that many companies experience on the daily.

While being relentlessly resourceful and doing a ton of things that don’t scale we’ve been able to put together a pilot group that’s excited to test what is a really incredible functional prototype that we’ve built from scratch.

I’ve tried to orient and lead my team with excellence and they’ve given me a ton of grace as I’m jumping between building, managing, operating, and everything else in between. I’m so fortunate to be working with them.

And so it begins.

And, in a few short hours, we’ll deliver the first prototype into the hands of an excited group and so that they can beat the snot out of it. We’ve got analytics running and a simple support system in place so that we can start taking notes.

We’re not quite the company that we want to be yet but we’ve been pushing 100+ hours a week to prove that we be a real, legit startup. I think we’re headed in the right direction, and the excitement is electric.

You see, I want to build startup, not just another company.

We are still looking for prototype testers! If your organization could use a little help with their new employee onboarding process / program we’d love to chat!

Please send us the following information in a short email (

  1. Company Name, URL
  2. The number of employees in your company (or your relative team)
  3. A few words about why you’d like to Alpha Test our tool
  4. How many new staff you’ll be hiring this year (a guess is okay)

To infinity and beyond!

Desk App: Live Preview Feature

I’ve been working a bit here and there to continually tidy up the overall experience of Desk and I know that a feature that many users have been asking about is the potential for a “live preview” for their writing.

Essentially, this feature will allow you to see how your writing / content will actually look on your existing blog (with the design). It’ll be a work-in-progress as I flesh out the details of how this might work really well, but, I think it’ll be helpful for some of you to see in real-time how your content looks to the end-user and reader.

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On Being Relentlessly Resourceful (Your Company Culture Starts Day #1)

When I decided to start putting a new company together I took a (brief) moment to review the past organizations that I had been a part of as well as the ones that I had the very unique pleasure and opportunity to build from the ground up — I wanted to be remember how I felt then and how I felt now and compare / contrast the feelings.

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