Category Archives: TOMO

Finding a Home on The Slack App Directory

The Slack App Directory

And a Strange Feeling That This Has All Happened Before…

Last week we were notified that our very young and very small Slack integration was fully accepted into the Official Slack App Directory (check it out here!) and we’re grateful and honored to be one of the first 400 apps ever in the entire directory — what a cool thing to think about!

If you would have told me even 100 days ago that we’d be making a submission to the Slack Directory and that this past weekend I’d spend most of it building out small micro apps via webhooks and a variety of different APIs I would have looked at you sideways.

But, that’s been the pattern of building so far as we’ve built velocity for our company, executing quickly and working towards product-market fit.

Good times, good times and you know what the strangest thing is? I feel like this has all happened before…

Hot dog!

Nearly 8 years ago the Apple App Store launched and the commentary from the sidelines and pundits were as varied as you could imagine, from people saying that it was the worst idea ever to others claiming that it was a new way of building software and that our lives would be forever changed (also for both good and bad).

A few folks guessed rightly and are now among the few that could say that they had all seen this coming, the rise of an entire ecology and ecosystem of value, exchange, and digital commerce.

To my own misfortune I didn’t think much of it and didn’t spend any time building software for it. I thought that it was too small and that the possibility of building a business on top of it was too risky. I wish I had reconsidered my position and dove in earlier and I promised myself that if I had an opportunity to do it all over again that I would.

And wouldn’t you know it? That time is now. With Slack I see more than just another “platform play” — I see another ecosystem, a veritable ecology of how businesses will do business, a new way of how we all get work done.

Is “it” in its “final form” (as they say)? No, not even close, but I do believe that all the tell-tale signs are already present and accounted for (and if you need me to enumerate them for you then you’re already behind the curve).

Consequently, our investment into the Slack economy is one of serious interest and being one of the first 400 apps approved for the directory is proof-positive of this investment.

You see, we believe there’s a real opportunity to empower HR staff (and employees) with better tools and technology so that they can do better work and help their organizations become much more healthy.

It’s a vision worth building towards, building for, and investing in — it’s why this company exists.

Oh, and this time, I won’t be looking back 7 or 8 years from now and thinking anything close to…:

Darn, I probably should have built something for that new environment, that new way of doing business. Oh well. Opportunity lost.

Nope, not this time.

We’re building something different, something special, and something that we believe will significantly change people’s lives. Follow our progress on this blog,via Twitter, or via our email newsletter.

A W-4 Form to End All W-4 Forms

Oh, you remember this form…

Wow, time does fly when you’re having fun, doesn’t it? Just a month ago we shared a small micro app to help people fill and complete IRS W-9 Forms, not the sexiest (nor prettiest) of ideas but incredibly useful for the many users who have given it a try.

And then, just a few weeks ago we announced that we had built the workflow in such a way that allowed an easy integration with Slack! We can’t help ourselves — we just like building stuff that helps people save time on their administrative tasks!

Today, we’re pleased to announce the next small micro app that takes what we built for the IRS W-9 Form and applies that technology to the IRS W-4 Form.

Slack-integration included!

A new landing page!

Our new IRS W-4 Form tool allows you to simple request, fill out, and send a W-4. Nothing super-fancy about that, right?

Except, that it’s also powered by our global admin and dashboard so that any user can create once and never have to fill it out again — they can just send another copy to another org as they’d like (and update any relevant information as they so choose).

We like Slack… a lot.

And, as we already mentioned, we have a Slack integration too!

Users within Slack can, with a simple command, make those requests right where they are!

This is particularly useful for the overworked HR administrator or manager who has to make these types of requests often of their new employees.

Especially if you’re in hyper-growth mode (like a startup) having our system handle this and for the admin to also get notices when they are completed (as well as a status of where they are in the process) just makes life a little bit more easy, which is worth the low, low price of FREE!

So hope that helps and we’d love your feedback (email us: as you give it a go and test it out the next time you hire someone in your organization!

Feel free to send this to one of your tired and under-resourced HR manager so that they can save a few moments of their day with administrative tasks!

Glad we could help!

The I-9 Form

At EVE we’re pretty passionate about making organizations more healthy and we believe that we can do that by automating the things that can be automated and thus giving back precious time to staff and employees so that they can do the things that automation can’t solve for: Human relationships.

Consequently, we’re continuing to build out our own technology that allows us to do this for all parts of the business!

So, what’s next you ask? Great question! On deck, as they say, is tackling the much more difficult I-9 Form provided to us by the Department of Homeland Security.

The IRS W-4 Form typically walks hand-in-hand with this document when a new full-time employee starts their new job.

If we can begin to create tools that automate these required workflows for companies then we can begin to really fulfill our mission as an organization — we’re super excited to know that we’re on track to do just that.

Talk soon.

At EVE we’re building a truly paperless business world. Follow our story here on the blog and follow us on Twitter or our email newsletter.

Eve: The First 100 Days

Images via BOSSFIGHT

A Retrospective Through Pictures, Tweets, and Text

Exactly 50 days ago I penned a picture-laden post about the first 50 days of our new company and today I’m going to do the exact same about the second set of 50 — hey, I’m good at math.

As you might imagine putting this post together encouraged me to look back on the first 50 days and it was honestly hard to review; it just makes me too darn emotional for my own good.

You see, things move fast in the world of startups but while you’re in the middle of one the concept of time gets totally destroyed, totally out of whack. Time is compressed and yet stretched at the exact same time and in a way that is really beyond measurement.

And the emotions that you feel and experience are all over the map in quality and type, breadth and depth. And that’s mostly because a startup forces you to encounter, at the most fundamental levels, your insecurities as a human being.

And taking pictures along the way is one way that I force myself not to forget my own humanity.

Where I ended the first 50.

The last 50 days have been an exercise of patience and execution, a reminder that great things take time and that big things always start really, really small. Working hard, staying humble, and moving fast.

There are a number of concurrent tracks that need to be laid and traveled on, such as building great product, financing, and cultivating a culture that you can be legitimately proud of, always.

To do this I found myself traveling up and down from SF to SV to hustle the conversations that were necessary to keep the financing side of things moving along as well as traveling back east to hang with the team and do a few other things necessary to keep production high.

There was a lot of CALTRAIN action in the past 50 days. Sand Hill Road was calling a bunch and I needed to take a lot of trips down there. Like for these fine folks:

A visit to Andreessen Horowitz. I walked from the Starbucks in Menlo.

Conversations are just that: Conversations. No promises. Dating is still much better here in SF than any other place as far as I can tell.

Coffee shops all across the the Bay were used to get things done, keep me hydrated (and awake). I used my bike for most of my travel if I could:

I’ve had so many things stolen off of the bike already.

Something that I experimented more with in the last few months is a number of coworking environments around the city. In Atlanta, I spent a long period of time visiting and testing out these environments and many of them were decent with very few of them being amazing.

Here, though, SF seems to be doing a vastly better job of creating functional work environments with the right of amount of amenities — many of them are not overdone, which I think is about right.

Everyone is here to get shit done.

A few weeks of #headsdown work and I found myself back out east to work with the team and then, more specifically, capture some video for some of our applications to accelerators.

Is there anything more goofy than two guys trying to talk about themselves about a product concept that barely even exists?

This entire experience was a mess. But, fun.

I took a stop by St. Louis to get eaten by a dinosaur as well on my way back to San Francisco:

Actually, chatting with a few college students and meeting one of our digital teammates was in order. That was legit and very fun.

A week later Billy was back in my part of town and we continued to hack the hell out of our product as well as a few interviews with Accelerators / Incubators. It seemed like our efforts around our video actually worked. Imagine that.

The bottom of my apartment building gets some serious use for this company and regardless of where it all ends up I’ll have made some pretty fond memories here.


You know, there is something definitely romantic about building a company from scratch. I don’t have a “garage” though so this story won’t include any of those types of environments (at least not right now).

We’d end up doing pretty well, as least as far as I could tell. More travel back and forth, more flights, more CALTRAIN, more coffee shops, more work.

And, more virtual phone chats, now using Slack instead of many of the other terrible alternatives:

What I love about what I get to do is first, work with great people. Second, I love the discretion that I have around my schedule. No one tells me what I can and cannot do with my time and especially where I should be doing it.

Maximizing my calendar with work and meetings is a neat problem to solve and an ever-evolving challenge — it’s actually something I don’t mind encountering every single week anew, as long as I know that my team and I are headed in the same direction.

The locations that I choose to do my work are just small parts of a much larger equation. I enjoy visiting different spots, testing out the “native” resources, and getting a good feel for what the “natives” feel like. It’s half anthropological and half sociological.

Always in the service of productivity.

More pitching, more prep.

Finally, the last few weeks have been focusing on shipping our new integration with Slack, a significant name change to “Eve”, and meeting a few more selected venture groups that have given us some interesting yet rewarding feedback on our concept.

We have a long way to go, but we’re getting closer to hitting some of the important internal benchmarks that we have as a team and we’re gaining ground in the many different ways that we need.

It doesn’t always feel great and we certainly do not see the fruits of our work immediately but if I am to compare the second 50 to the first 50 days — it doesn’t even feel like the same thing, the same company. Even I feel significantly different about myself.

A startup changes you. We all know this but very few of us take the time to introspect while it’s happening. I want to create a business and a culture where this type of effort and activity is encouraged and I have to model it for my team by actually doing it (imagine that).

I can’t wait to see what the next 50 days bring. Day #150… watch out.

Today is Day #100 of our new company and it’s been an incredibly-fun and wild ride. You should follow our progress on this blog,via Twitter, and/or via our email newsletter for updates.

These are My Two “Must-Haves” When It Comes to Finding the Right VC

The Right VC for the Right Seat on the Plane.

Finding the right investor(s) for your new company is hard, no question about it. I would know because I’ve been living this reality for the past 3 months as I put together EVE.

I’ve been told that my startup is “Unsexy as Fuck”, have been acutely reminded about how annoying this process (and VCs) can be, and have been humbled by how terrible my pitch efforts can be.

But hey, it’s has been very positive on the whole — I’m quite thankful and I love the process because it’s part of putting together my dream that is my company.

For those who know, though, there’s no question about the experience of finding the right fiscal partners: It’s arduous and difficult work — not only do you have to weed through a ton of them to find the right one(s) and fit, which is time-consuming and difficult in its own right; there are, in addition, a near-infinite amount of things that are wildly outside of your control that can make or break a potential deal.

With all of moving parts it’s best that you, as the leader, have your own list of what you’re looking for and stay true to them. In fact, this isn’t just the best way to operate, it’s really the only way to operate since you can control very little of the process.

So, you create your own small list of what you believe to be uncompromisable when it comes the financial partners that you want to work with. Note, this list may end up being fluid and changing depending on the round and stage (e.g. Seed, Series-A, Series-B, etc).

For me, the core list of requirements has always been pretty small which allows me to have a bit of that fluidity based on stage. Here’s mine:

  1. Proven Integrity
  2. Real Operating Experience

That’s about it. The rest of the details (and they are just that, details) can be ironed and fleshed out over time, but without those two things I simply can’t move forward.

Here’s why…

Real integrity is refreshing, always tasteful.

Proven Integrity

It’s easy and hard to understand quickly if someone has integrity, if they have the moral fiber and fortitude to make the right decisions more often than not.

It’s easy on one hand because you can quickly get a gut feel for whether they are the right people for the job, for the mission that you’re asking them to be part of. This gut-level instinct is something most entrepreneur’s have, an ability to cut through the bullshit and get to the really important stuff really fast.

You can also easily do your background, reference and relationship checks as part of your due diligence and a few probing and specific questions can give you a lot of context that you need. VC’s are looking for patterns (i.e. “pattern matching”) and you should be too, finding a consistent narrative from their own lips and from other’s that have the pleasure (or the pain) of doing business with them.

At the same time, it can be very difficult to ascertain true moral character and integrity. Why? Because even in healthy relationships it can take time to get to know someone for who they really are and incubating and cultivating a relationship towards a discrete deal, at times, needs to happen with some modicum of speed.

And finally, in most situations, you just won’t know until you just give it a go, trusting your gut and giving the relationship a try. Hopefully it blossoms into what you had hoped it would become and continues to head in that direction.

On the flip side of things, unfortuantely, you’ll know pretty quickly if what you were sold was a “bill of goods” — it’s just one of the costs of doing business, one of the natural risks that you have to take when trying to build a company from scratch.

Suss out their integrity, ask the right probing questions about who they are, where they’ve been, and why they made the decisions that they made.

What you’re looking for, at a top-level, is a consistent pattern of decision making that you could classify as such:

This person intentionally and consistently does what is right for the company and what is right for the people that they serve.

These people just do right by other people and you get an overwhelming sense that they would do the same for you and your team.

By the way, having integrity isn’t about being nice and it certainly isn’t even about doing what is fair — it’s about doing the right thing, publicly and privately.

You can know and learn about the former from others and you’ll have to learn the latter over time as you align outside perception with inside knowledge turned wisdom. You’ve simply found them to be the same person, everywhere.

Remember, people without integrity will fuck you in the end. It’s inevitable.

Choose wisely.

They know the game. They’ve felt it. Played it. Touched it.

Real Operating Experience

This is as big of a deal as the first requirement because in many ways their ability to lead and coach me with integrity is based on their ability to speak truth into my life based on fact, not theory nor fiction.

What I mean by this is very simple: I always want to find financial partners who know what it’s like to build companies, at every stage but most especially at the earliest stages of company building.

I need to know that they can more than just sympathize with the challenges of startup life but can deeply, personally empathize with me and my team. In short, they’ve been there, done that.

I believe this to be pretty self-evident but I’ve come across a number of entrepreneurs who don’t keep this on their shortlist of requirements. Personally, I think that’s pretty stupid of them but that’s just one man’s opinion.

But it shouldn’t surprise anyone that, statistically-speaking, the most successful venture firms are the ones that have previous entrepreneurs and operators in their general partner ranks:

via TechCrunch
via TechCrunch

These general partners (and the firm as a natural consequence) can put real, explicit, and discrete knowledge and experience into their investing thesis as well as their investments.

They have lived, breathed the entrepreneurial journey, all the ups and the many, many downs. They know the agony of having to make some of the hardest decisions of their life and many of them know all-too-intimately the darkest corners of despair as they’ve had to close down shop.

These are the “realest” venture partners, the type of people that I really want to work with. Their words of wisdom, their coaching can be trusted because it sits squarely upon battle torn experience and legit scar tissue.

And, to be sure, they simply won’t bullshit you — they smell it a thousand miles away and know that bullshit never builds companies.

Actually, to stick on this point for a moment, their bullshit-ometer relates directly to a very simple and easy smoke test that you can use and leverage while you qualify them as a partner. You see, you’ll know clearly whether or not a VC has real operating experience not by what they tell you they’ve done (i.e. their apparent “war stories”) but rather the quality of the questions that they ask you about the work that you’re doing (and plan to do).

In short, a quality VC with legit operating experience will inevitably ask the questions that are difficult to answer, sometimes painful. You want those type of folks. You don’t need cheerleaders, you need coaches.

As emphatic as I am on this point it’s worth noting that this matters to me much more at the early stages than the later. Although it’s always preferable at all stages, you’ll naturally have to build and make deals with more and more parties, many who may not have the key operating experience that you need.

Thankfully, the venture landscape has grown so significantly that finding a GP in most firms who has the experience that you need is within reach and you don’t need to build deep-level relationships with all of your investors.

Play the relationship game close to the chest, pick and choose wisely, and you’ll find that you’ll be handsomely rewarded (and not just capital).

Here are a few additional resources and points of reference, especially related to the “Top VCs” research:

We’re building something different, something special, and something that we believe will significantly change people’s lives. Follow our progress on this blog,via Twitter, or via our email newsletter.

Originally published at John Saddington.

Design Thinking in HR: Empowering Your Staff with The Right Tools at the Right Time

Bob Dylan

The Mission of the HR Leader is Evolving from that of the “Chief Talent Executive” to the “Chief Employee Experience Officer.”

Bob Dylan once famously sang these words through his title track on his 1964 album of the same name and many of us have been humming it to ourselves ever since:

Come gather ‘round people
Wherever you roam
And admit that the waters
Around you have grown
And accept it that soon
You’ll be drenched to the bone
If your time to you
Is worth savin’
Then you better start swimmin’
Or you’ll sink like a stone
For the times they are a-changin’.

And for those of us who live in the world of software and technology we know this to be true — in fact, for many of us, this song is very emblematic of who we are as people, as professionals, and this song serves as an anthem to the constant push for newness, value-generating innovation, and the stark reality that things change so quickly around this town.

But implementing change is hard; we are creatures of habit and change is almost always uncomfortable, jarring, and something that we naturally want to avoid when given options.

And even those who would volunteer themselves as being the most open to change know a time (or two) where they’ve been forced to change because, well, “the times they are a-changin’” and it was just an inevitability.

Image via Deloitte

In a recent study done by Deloitte on Global Human Capital Trends in 2016, they’ve been able to codify a few truths that we have all already begun to experience. Per their report:

After three years of struggling to drive employee engagement and retention, improve leadership, and build a meaningful culture, executives see a need to redesign the organization itself, with 92 percent of survey participants rating this as a critical priority.

The “new organization,” as we call it, is built around highly empowered teams, driven by a new model of management, and led by a breed of younger, more globally diverse leaders.

And there’s no question — the workforce has gotten flooded by younger folks, millennials, who have been introducing faster, more fluid, and more powerful forms of tooling and business applications.

The so-called “redesign” or reinvention of the organization is already happening: You encounter it just as you wake up and it’s the last thing that you do before you fall asleep — the change is here, it’s deep within the very heart and soul of the business that you walk into every single day.

If you’re using any form of “modern” workforce communication tool, like Slack, then you know this all too well. It’s insane to imagine that only 2 years ago most of the world didn’t even know this technology existed and if you move back 3 years it actually didn’t exist at all (the original product built by Stewart Butterfield was a video game called “Glitch”).

And yet, now, many of us can’t possibly live without it — Slack is as “mission-critical” as it gets and entire organizations run almost their entire organization through the platform.

Why? Because Slack has democratized the flow of information from every angle and facet of the organization, from the individual contributor to the C-Suite, and allowed individuals own their roles, their job functions, and their corporate experience end-to-end.

But notice how I said “almost” because there are still some incredible opportunities for the forward-thinking company to take advantage of, areas of the business that have historically been owned by the organization and not by the staff and team, one of them being Human Resources.

…the times they are a-changin’…

via Deloitte

Deloitte’s level-setting piece continues to codify a new reality for the progressive, technologically-rich organization and truly heralds the growing role of the HR-centric business and the HR Leader as one of the most significant for our future:

Amidst these changes, the HR function is taking on a new role as the steward and designer of these new people processes. The mission of the HR leader is evolving from that of “chief talent executive” to “chief employee experience officer.”

HR is being asked to simplify its processes, help employees manage the flood of information at work, and build a culture of collaboration, empowerment, and innovation.

The call is clear and for those that are already in HR you can feel the pressure of providing and increasing amount of value with speed, accuracy, and always digitally and always on-demand — there is truly a “flood” of information for both the existing staff member and especially the new hire as they onboard and learn the ropes.

One way to do this is through more strategic and advanced design thinking, a way to focus the employee’s experience and creating processes centered around the worker, instead of the organization. This is also known as “human-centered design” thinking.

Technology, like Slack, is allowing design thinking to become even easier to implement and customize. And the result is a major uptick in employee satisfaction, productivity, and enjoyment.

As Deloittes notes:

Applying design thinking to the work experience compels HR to ask, “What does a great employee experience look like from end to end? How can we facilitate collaboration and learning in everything we do? How can we take advantage of location-aware mobile devices to make people more productive? How can we give employees a few easy-to-understand choices so they can make decisions faster?”

Exciting new digital tools that employ design thinking are also making routine HR tasks more efficient and easy, while improving the employee experience.

She’s called “Eve” — she’s learning and growing every day (just like you).

And this is why we’re building an HR Superbot named “Eve” — creating new digital toolset that is accessible in the very context that your staff do their work.

It’s as simple as a few familiar /slash commands (and it shouldn’t be any more difficult).

In other words, we hope to bring the solution (“Eve”) to the employee in a way that’s approachable, familiar, and that saves both them and the HR organization a ton of time, making those “routine” tasks efficient and easy.

In fact, we believe that we can make it better than efficient and easy; if we do it right we’ll eliminate it entirely. Wouldn’t that be nice?

You see, existing HR tooling just doesn’t give this amount of freedom, customization, and flexibility. These older tools do not allow design thinking to be applied liberally and they do not allow the HR organization to study their team and craft and shape a compelling employee experience.

In short, an organization would do well to think of how they can deftly apply design thinking in their organization’s technology and culture, especially as it applies in the business units of HR — their competitiveness, profitability, and retention of top talent for success depends on it.

The times have inevitably changed for HR in exciting and powerful ways — embrace it with open arms… what other choice do you really have?

The line it is drawn
The curse it is cast
The slow one now
Will later be fast
As the present now
Will later be past
The order is
Rapidly fadin’
And the first one now
Will later be last
For the times they are a-changin’.

We’re building something different, something special, and something that we believe will significantly change people’s lives. Follow our progress on this blog, via Twitter, or via our email newsletter.

TOMO is Now Eve

We’ve been super-busy (and it’s been a lot of fun)!

And We’re Building an HR Superbot (Also Called “Eve”)

To cut to the very quick chase… we’ve changed our name from a 4-letter word to a 3-letter word, thus reducing the typing requirements into any browser window by a dramatic 25%!

Okay. Less dramatic, we’re moving away from TOMO as a name and brand and now adopting Eve from here on out — we couldn’t be more excited!

In fact, you may have already noticed the swap with some of our social media accounts (Twitter is now EVE_IO) as well as our Medium-powered publication, now housed at

But that’s actually not the most exciting thing that we have to announce…

We’re integrating with Slack!

Eve Gives HR Managers Super-Powers

Saving You Time So You Can Focus on More Important Tasks

Our mission with Eve is very simple: Go paperless. It’s something that we had in mind when we first started putting this company together and is still at the very heartbeat of what we’re building. It’s a clarifying “north star” in all of our decision-making, especially when it relates to the products that we’re creating.

You see, a truly paperless organization is smart and strategic enough to use tools that allow their staff to operate in the context in which they do their work. In other words, a paperless organization leverages apps that operate in-line with their other mission-critical tooling.

/eve request w9

We believe that Slack is fast becoming a fundamental part of business life and we wanted to bring our solution and workflow into that world, as frictionless as possible.

And that’s what we’ve done.

Now, you can integrate directly with Slack and make requests for IRS W-9 Forms via a simple slash command:

/eve request w9

It’s that simple. Send as many you’d like! We’ve also created a simple way for you to get the “STATUS” of those requests as well:

/eve status

And this is just the start.

/eve status

We are quickly using our technology to build out other requests that Eve will be able to manage and create for you, including workflows and tooling for full-time employees.

Our hope is to continue to iterate and expand the intelligence of our new superbot so that, in time, Eve will be able to assist and manage most of the repetitive HR functions that HR organizations, specialists, and managers have to deal with every single day.

Imagine how amazing that would be! Imagine a world where an HR Superbot could be trusted to manage and oversee the majority of your daily administrative and document-related tasks.

Imagine a world where an HR Superbot could be tasked with answering most of the common questions that your staff and team ask you regularly (e.g. payroll, benefits, flexible spending, reimbursements, etc.)!

Imagine a world where an HR Superbot could free your schedule up to focus on the more interesting and important tasks like investing in your staff and the organizational culture and giving you margin to manage the elements of your job that no bot could ever do, like conflict-resolution, career development of your staff, and cultural assimilation.

You’re already a hero to your org — let’s level you up even more!

That’s where we’re headed with Eve, the first-ever, HR Superbot that will be able to connect with your core business tools and HRIS / MS solutions seamlessly, accessible at every part of the business anytime, anywhere.

But, we can’t get there without your help and feedback!


So, we’d love for you test out our first implementation and then email us your ideas and/or suggestions about how we can make Eve the most amazing HR Superbot ever.

Email us here:

Can’t wait to hear from you!

At EVE we’re building the world’s best HR Superbot, integrated directly into Slack. This is our story of how we’re putting it together. Follow us on Twitter and sign up for our email newsletter.

Hey, Your Startup is “Unsexy as Fuck”

We’ll take it. It’s our ugly baby and we like it.

But It’ll Make a Lot of Money…

We’ve been making the rounds lately with VC’s and it’s been a trip (they say the darndest things) and I wish I had taken more notes because some of it is really quite tweet-worthy (if that’s a thing).

No, these aren’t any of the irritating things that VC’s say but rather clever one-liners that are both memorable and true, probably the former because latter. Yesterday we got this doozy that I really appreciated a lot:

Hey, it’s unsexy as fuck… but it’ll make a lot of money… and I like those types of companies.

And he was/is right: Our startup is as unsexy as they come and there’s really no way to put any lipstick on this pig — and I like it a lot.

But it didn’t start that way.

Move fast or perish.

At this point in time we’ve put together three working products / prototypes with customers to boot and I’m super-proud of the progress that we’ve made in the last 88 days (yeah, I’m counting!).

And what’s crazy is not just how far we’ve come but how quickly we’ve been working to attack the problem from different angles and perspectives. This makes sense because we’ve been attempting to ship Version Zero Dot Zeroes as much as we possibly can and reducing our core concepts to bare bones.

What’s equally fascinating to behold and admit is that our idea has become less sexy every single iteration. Our original idea and prototype was a super-sleek workflow tool for onboarding new staff into an organization. A worthy goal and something we felt really good about.

But that wasn’t what the customer’s really wanted; so we had to reconfigure and isolate a much more acute problem that they were having. We came up with a “universal profiling tool” a’la GitHub that wasn’t an entirely new concept but we attacked the problem in a way that was distinct. And, it had our corporate and team DNA all over it.

Less sexy? For sure, but we gave up the sex appeal so that we could attack a much more discrete problem that we knew that we could solve uniquely. If there was any serious deliberation about our first pivot it didn’t last long — we knew that it was right and we were learning to become a real product and engineering company.

So we fought (i.e engineered) hard to maintain velocity and eventually pushed through to our first public microapp which we launched exclusively on Product Hunt — it achieved some of our internal goals and even hit a few more that were very surprising (and welcome).

But let’s take a step back, shall we? We had moved from a complex, infinitely-scalable workflow tool for onboarding staff to an GitHub-like human capital profiling system to… *wait for it* … … … automating government paperwork.

I mean, let’s be intellectually and emotionally honest here — there’s just nothing sexy about the IRS W-9 Form:

There she is, in all her glory.

So when we stepped into this VC’s office yesterday and showed him and his team our progression over the last 3 months and where we’ve landed with our three prototypes he shared what was intuitive and self-evident:

… it’s unsexy as fuck.

And we were all-smiles. You see, we could legitimately beam with pride with that comment knowing that we had landed on something that was not only useful but the beginning of something much bigger — which is why he mentioned shortly thereafter that it had incredible potential as a business).

You see, we had proven our core hypotheses to be true and we had hit some really neat internal milestones, and we were iterating / engineering like mad men as well as building go-to-market collateral and optimizing internal operations weekly.

His comment was clarifying and encouraging; it struck a sweet chord with the team and was a real moment to remember.

There’s a lot of potential here.

This meeting was also special because we demo’d for the first time our next iteration of where we believe we need to head with our product. And you guessed it — it’s not getting that much sexier.

And that’s great because we didn’t set out to build a “sexy” product or a sexy company — we set out to build something that people would use and something that businesses would pay for because of the high-value that it created. If we’ve done anything sexy it’s just that we’ve worked our asses off to get where we are (although that, in and of itself, is not unique as that’s the standard for putting a company together from scratch).

But I can tell you that I am having the time of my life building things that resonate with others with people that I really love working with.

And that’s important because there are only a few things that you can really control when it comes to a startup, and those things or elements center around your decisions of who you want to work with and the shared values that all of you agree make the most sense.

And I’m proud of what we’ve put together and the team that’s behind it all —you know, that’s really, really sexy.

We’re putting together something entirely unsexy but is proving itself to be a pretty sweet business opportunity. You should follow our progress on this blog, via Twitter, and/or via our email newsletter for updates.

An Epic List (100+!) of The Best Free & Paid Web Tools for Freelancers & Contractors

A list to end all lists. All images via BOSSFIGHT.

Organized by Category for Your Viewing Pleasure

If you’re like me then you’ve probably experimented with both full-time employment as well as freelance and contract work — both have been very satisfying ways of earning income and I’ve been thankful that both models exist for me and my family.

Right now I’m doing the “full-time” thing but that’s only because I’m in the process of building a new company, TOMO and a small micro-app to help contractors and businesses send & receive IRS W-9 Forms — this is partly why I put this list together so I can do a bit more research into what our growing 1099 / gig-economy demographic needs to do their jobs well.

You should give it a spin — we’d love that!

It’s been great and I’ve loved sharing the journey through our blog.

In any case, I have a ton of freelance buddies, friends, and colleagues who are always asking me for advice on how to get started, what tools to use, and the like, and it’s not that I have the absolute best advice to give but I’ve certainly been around for a while.

And, as a consequence of just being around for some time I’ve amassed a pretty large collection of tools that I’ve used or experimented with in the past — I thought I’d share those publicly to help others.

Feel free to comment and add a tool that you think should be on the list — and if this post is helpful please share it and give it a HEART!

Get in those hours.

Time Tracking, Invoicing

We all need to track time, especially if we’re getting paid by the hour.

The numbers matter.

Taxes, Expenses, and Accounting

This one is critical and you need to make sure you’ve got the right tools for the job — this one could mess you up badly if you don’t have your junk together! So, do it!

You never do email in bed… right?

Email and Project Management

Now, email is our lifeblood (we all know that) but the better you can manage it the more sane your life becomes.

Calendaring on all platforms.

Calendars, To-Do, and Scheduling

Closely aligned with email is making sure you show up at the right time for the job — don’t be too late or too early!

Type. Type. Type.

Blogging, Publishing, and Writing

I love blogging and it’s a huge part of my own story and how I build companies — I think that the freelancers and contractors who write have a serious leg-up on the game.

Starting to make it real.


Getting your concepts and designs into prototypes is huge. These should get you started and on the right track.

Every bit counts.

Fonts and Styles

Content, words, and images are all important but making that content stand out is all part of design.

Design. Design. Design.

Design Products, Apps

These are the things that make it go “pop” — or, if you don’t like that word, use something else (yes, I know… I know…!). :P

Colors, Styles.

Colors, Styles

Give it a little bit of life, will yah?

Getting things organized.

File Management

These are some of my favorite apps!

Icons everywhere.

Icons and Iconography

These things give text a little bit of something extra.

Hopefully a little more than just a few pennies.

Getting Work, Jobs, and Getting Paid

Here are a few websites to find jobs and gigs.

Images, cameras, and more.

Images, Stock Free Photography, and Photos

Make it pretty.

I’m taking notes.

Have a Resource to Add? Comment Below!

I’m listening and will keep this list updated, which is much more easy than other systems of note — I can just edit this post and add them at will. And, if you have any other suggestions on how to best curate and even organize them, that would be helpful too.

(Obviously this isn’t a comprehensive list by any stretch of the imagination.)

So, feel free to contribute an additional resource via the comments! Thanks so much for helping out. Keep ’em coming!

Oh, and don’t forget to do this:

At TOMO we’re building simple tools to help part-time, full-time, and contractors get their work done (as well as the businesses that hire and employ them). Follow our journey via our blog here, via Twitter, and subscribe to our kick-booty email newsletter.

A/B Testing Our Way Toward Product Success

A/B Testing helps you see all things more clearly.

Or How I Got Over Myself and Started A/B Testing Our Landing Page Immediately After Our Product Launch

As an entrepreneur, engineer, and full stack founder I’ve been doing all that I can to push the very limits of our what our team can produce every single day, including myself. It’s fun yet entirely exhausting.

You see, there are 1,000 things that need to get done and only a small amount of hours to do them — good leadership understands how to manage these two disparate points of data and how to define what is truly “critical path” and what is wholly extraneous, even (and especially) when those things do not feel that way.

Fortunately, I have had the pleasure of working some amazing leaders in the past and their seemingly-innate ability to make tough calls amid a storm of options is precious and instructive; how does one really find the strength and have the self-awareness required to swallow their pride to do the things that do not seem to make the most sense, especially when you’re the leader?

It’s magical to behold when modeled well and over the past few years I’ve been training myself to become better at this. Curiously, it doesn’t seem to get any easier (imagine that).

That “featured” image though…

When we launched our IRS W-9 Form app exclusively on Product Hunt just 10 days ago we had some internal goals that we had wanted to hit and we managed to cross most of them off our list (as we shared in our Product Hunt Retrospective).

We felt good about our launch and it was a good, real-time flight test of what we felt was the smallest functional product, a true “Version Zero Dot Zero” as we’ve called it.

But it gets better — not only have we had great usage and sign-ups for our small tool we hit 2 internal milestones that we’re pretty stoked about:

  1. We had not one, not two, but three Fortune 500 companies sign up to create organizations and request IRS W-9 Forms for their contractors.
  2. We had one business break the double-digit request ceiling this past weekend. In other words, one organization has requested more than 10 W-9 Forms for their contractors making us their go-to tool. Amaze!

So good. So yummy.

In the latter case we were so excited that we sent them a tower of Ghirardelli Chocolate with a small note thanking them for using our new service.

I mean, it’s a big-stinking deal to become the defacto tool for an organization and for them to trust us with incredibly-sensitive data (but we’ve got our encryption on “lock” —yes, yes… pun intended).

So, we have much to be thankful and grateful for — and hell, we’re just getting started!

But that wasn’t enough for our team — we wanted to make sure that we could not only optimize the product for our growing customer base but also to optimize how we converted new visitors into real users.

A real A/B Test is what the doctor ordered.

Let’s get it open, let’s get it done.

In our launch post we happened to share our core technology stack and we’re continuing to expand that list as we introduce new technology into our product and engineering. We feel good about this for two reasons:

  1. We lose nothing by sharing our process and our technology. Our real advantage as a startup in the early stage is shipping, quickly and with a shit-ton of conviction. Full stop.
  2. We feel indebted to the amazing resources and material that we’ve used and have learned from in the past as we’ve grown as technology professionals — giving back is part of keeping that “open source” and virtuous circle alive and well.

And in this post we’re going to share some of our additional efforts in building a real business (not just an app) and how we work towards finding real product-market fit.

Now, in the past, I’ve opted to wait much longer before starting any real A/B testing but it just made a ton of sense to start immediately. And, if I’m to be honest, one of my cofounders felt really strong about it as early as possible, so, I felt really good about implementation.

It does the job.

To do this we used a simple gem called Split which you can find here.

As the description covers, it’s a light-weight, customizable A/B testing framework for Rails, Sinatra, and other rack-based apps.

Hacker-friendly, you can extend it and customize it to your heart’s content.

With statistical validity, weighting options, and the ability to run multiple experiments at the same time with a simple UI dashboard to aggregate results real-time, it was the clear technology winner for what we needed to do (and we could implement it quickly).

The result? We came up with two landing page designs, the first having a simple white background and interface:

Design One (or “White”)

The second included a different color set as well as an extended description of the app and product as a whole:

Design Two (or “Purple”)

You see the expanded overviews below the action at the top of the page, below, which included text and images:

For both the “Contractor” and “Employer”

If you visit our IRS W-9 Form app you will see either one — give it a spin or share it with someone who’s a contractor or a business who hires and works with contractors! Appreciate that, a lot!

Although the results are still young and inconclusive, it’s already destroyed my confident guess as to which one would ultimately fare better and become our default and standard.

Did I mention that building a startup is humbling? Yeah…

Decision-making in a startup is like trying to see the sand below the surface.

So, about that — when you start a company and begin building a product to solve the problem that you believe is worth solving you hold a number of wide-sweeping assumptions about the market, the market’s need and ability to bear the weight / demand, as well as your own and your team’s ability to build something that the world really needs and wants.

The honest-to-god truth is this: You simply have no idea if what you’re building is actually going to work and if the world really will give two shits about it. If you can’t be this intellectually honest with yourself and with your team then it’s probably best to go do something else with your time than to start a company — I mean, it’s just too hard to deceive yourself for that long and not go absolutely insane.

But the best startup leaders validate, all-day every-day. They look for ways to make their so-called “hunch” into something real, something tangible. Sure, they dream big but they also, at the same time, find creative ways to qualify their moonshot dreams into something quantitative.

In other words, they seek validation through data, through real-life metrics, instead of hoping and praying that things just magically work (they almost never do, by the way).

We call our A/B Testing Dashboard “Cosmo”… #culture … :P

And that’s what I’m trying to do for our very exciting little project — find the points of validation and the avenues to receive validation as quickly as humanly possible.

If that’s through survey data, then great. If that’s through growth-hacking the hell out of niche industries through Google Search, then go do that.

And, if it’s A/B Testing just a few days post-launch despite the increasing pressure of building additional features in the existing while serving brand new customers then you should do it.

Yes, yes… it doesn’t feel like the most optimal use of engineering bandwidth but that’s the point — strategic founders will tactically ignore their feelings for discrete opportunities for validation more often than not.

But it still doesn’t feel very good at the moment (and that’s okay). I mean, none of us signed up for this because it was going to feel good, right? No, we started building our companies because we felt morally obligated to build them, like an invisible force that compelled us to start, to begin.

Don’t stop, keep going.

We’re building something so strangely obvious (at least to us) with TOMO that most days it feels like an embarrassment, but that’s okay. This is our story of how we built something that people wanted. Follow our story via this blog, on Twitter, and our email newsletter.

The Full Stack Founder

The startup founder is, above all else, a hustler.

How An Entrepreneur Can See Rightly Their Role and Responsibilities as a Business & Company Builder

Via The Full Stack Employee:

The conventional seams between disciplines are fraying, and the set of skills necessary to succeed are broader and more nebulous than they’ve been before. These days, you’ve gotta be a real polymath to get ahead; you’ve got to be a full-stack employee.

When I first encountered @chrismessina description of what he called a “full stack employee” it resonated with me a bit.

I thought it was, at the very least, and interesting way of borrowing a term that had been originally applied to a technical employee (e.g. full stack developer) and it got me thinking critically about not just who I hire when starting a new company but how I think about hiring the right people.

Let’s be clear: Chris’ thesis isn’t perfect by any stretch and my biggest problem with the piece was that it could be interpreted as attempt to describe (and prescribe) the model employee for an organization, what the “best” looks like and should be in today’s modern economy — I don’t agree with this possible sentiment but I’ll expand on this in a bit.

But, that doesn’t diminish the value that the post created: It was important at the time (and even now) because it gave folks an opportunity to discuss an important topic: Hiring.

Everyone has “gear” — it depends on how you use it.

And that’s good because there’s a ton of room for improvement in that area of doing business; all of us business owners, myself included, can learn a thing or two about how to better hire for their organizations! And, we should always be looking to level-up in this area as things change and as our own companies evolve and grow.

The reality, though, is this: There is a significant amount of need for all types of employees, the specialist, the generalist, and everything in between. We need all types for fully functioning organizations and we should celebrate that. There is no “one type fits all” employee nor is there a “best” type of employee, at least from my perspective, just as there is not a “one type fits all” business or company.

So, the question and issue isn’t about whether you are the right type of employee — the question is whether you are the right person for that job at that company at that specific time. It’s about context, timing, and relevancy.

To be more specific, early-stage startups need employees who can apply skills broadly in and over a wide set of disciplines simply because there is too much work to go around and not enough hands to literally do the work.

This is, for the uninformed, simply based on economics — early stage companies do not have the financing (if any) to pay for more employees to specialize and attack the more separate and discrete business areas.

So what does that mean for founders? What that mean for the future of company builders? I think it provides a bit of a framework for thinking that has, at the very least, helped me think through what it takes to start a company (since I’m kind of in that mode right now with TOMO).

The Full Stack Founder gets shit done.

The Full-Stack Founder

After spending time with a great bunch of students at WashU this past week and chatting for a few days about entrepreneurship it dawned on me that many (most?) students are generally unprepared to be a business founder, and, closely tied to that, an entrepreneur.

Most of this is simply because they have yet to experience it, which is fine, and this is not necessarily any fault of their own. Although, I would argue very heavily that those who want to be an entrepreneur should be doing entrepreneurial things which means building and shipping things, learning to work with others well (i.e. building and managing teams), and just “entreprenur-ing” if that word can be used.

There’s no reason that these things can be practiced extensively, daily, in every environment and it’s been proven time and time again that college students can create world-changing companies and businesses.

Unfortunately, many students have only been given a partial story about what it really takes to start a company and then to be a company-builder and sustainer / maintainer of that company.

You see, many people (not just college students) have fallen in love with all of the upside of entrepreneurship (i.e. the rewards) but have not yet encountered or been told as fully about the downside: The hardships, the fears, the anxieties, the loneliness, and how scared shitless you are all the time under a crushing weight of responsibilities.

The darkest times of my life have been while trying to build companies. I have never felt more alone when launching a startup, even with great cofounders. Sadly, these things cannot be expressed or told or taught to others — you must learn through experience these things for oneself.

Things move quickly (and if they don’t you’re in trouble).

And, there is a significant difference between being an entrepreneur (and a person who builds companies) compared to one who is just building an app. Those are not the same thing. Just because you can program or build something does not mean you know what it’s like to build a company.

Building a company means that you’re the first person on the team. Being an entrepreneur and founder means that you have to not only engineer a product (i.e. build an app) but also know about finance and accounting, marketing, sales, customer support, product development / product management, research and development, and any / all administrative tasks.

Take note that I didn’t say you had to be an “expert” at all of these things nor do you have to be overwhelmingly good. Rather, in a somewhat poor and limited metaphor, it’s like being an excellent basketball player (and as a consequence, an athlete) and also being comfortable playing soccer, throwing a football, and jumping into the pool to play water polo recreationally with your friends.

In other words, you’re not an expert at everything but you have the awareness to grasp the fundamentals and apply them immediately, as best as you can. And you’re motivated to execute because your friends invited you to a local pickup game and you had the interest to do it. You wanted to perform, to help the team win, to have a good game.

The same thing can be said of a founder, a business builder. They may be an expert in one area (or may not be, it really is fairly fluid) but they have the situational awareness and resolve because they have to get shit done. They have to make this thing work.

So, back to my WashU experience this week… I, again, was reminded of how uninformed many of the students were about the difference between building an app (or being a “hobbyist” programmer) and building a company, and during a painful “Open Office Hours” section of my schedule yesterday I met a talented and driven young man who had just spent the last year building an app but confused that with building a company.

I, in the nicest way possible, shared with him that if he was building a real company then he also must spend time learning the other facets of what a business requires, not just engineering a great product.

This was a painful encounter (for him and for me) but an important one. Building an app is not the same thing as building a company. They can be related but do not necessarily have to be.

For instance (and semantics aside), I have built many apps, some that have been successful (like this one) and many more that have done terribly. But even for the ones happened to achieve a modicum of success were never real companies, they were never a real startup venture. They were just personal projects, and I’m comfortable with calling them for what they are.

Finally, for what it’s worth, neither is wrong or better or worse; you can be a “hobbyist” programmer or you can be a programmer who builds a company. Both are great and you should do what is right for you.

“Full Stack!”

So what does this mean, then, for a student (or anyone else) to become a really great founder? I think it means that you should become more of a “polymath,” a person who begins to acquire a number of skills besides becoming exceptionally good at one or two.

And, if I were to honor the original meaning and intent of what polymaths have been throughout history, one would become a student of the entire lifestyle required to not just acquire those skills but to live them out in all areas of life.

Robert Heinlein is well-known for his thoughts on this type of person:

A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.

There’s a lot of good sense here, by the way, logical. As a founder you have the blessed opportunity to do anything and everything to get the company off the ground. Literally everything — you have to. This is a consequence of being the only person on the team when you start. And even if you have cofounder (which you should) everyone does everything all the time.

Therefore, if one was to try to prepare to be a great founder of a company (and to increase one’s odds of success as a company builder) then becoming more equipped in the many areas of business building would be sound advice and counsel.

Remember, the goal isn’t deep-level expertise in all areas of the business — the goal is to know enough to be equipped and dangerous and open and humble enough to do the work necessary to get a company off the ground.

I find the athlete example a helpful one.

If we can return to the somewhat-poor metaphor of an athlete who professionally plays one sport but can recreationally engage in others, this may be a good and helpful example and metaphor.

Or, put another way, as a founder, there is no task that is too below you, no task too small for you to do it. You do not (should not) outsource much when you start (if anything).

You do it all and that’s important. You are the engineer, the designer, the marketer, the salesman, the product manager, the first-line of customer support, and the gal who puts together the shitty IKEA furniture that you got second-hand via Craigslist, all at the same time. You do it all.

Why? Because you are a full-stack founder. You understand that to survive you must be willing and able to do all of it, even when you’re not an expert. Why? Because there is no one else to do it. And your partners, co-founders, are right there with you, building, doing the heavy lifting, and also putting together those shitty IKEA chairs.

SIDEBAR: This is a good “smoke test” for whether that person will be a great cofounder with you: Is that person willing and able and interested and hungry enough to make this venture succeed that they will do any and all of the tasks necessary for success which includes the more menial and mind-numbing tasks ? Are they humble enough to come in on a Saturday morning to build IKEA furniture?

If not, perhaps you’re working with the wrong person. Oh, and this is also self-reflective too — if you are not ready, willing, and able to do the small things because you’re too good or too self-important then you’re probably not ready to start a company, entrepreneurship is probably not the right career and profession.

Well, at least right now.

“Preparedness” is not a requirement for a full stack founder.

In summary, the full stack founder is more about one’s interest and openness in doing the tough work necessary to start a company and less about their innate skill set or natural expertise. A full stack founder is relentlessly resourceful, a polymath when it comes to rolling up their sleeves and getting shit done.

I want to work with those types of people. I want to hire those types of people. I want to be that type of person. No job is ever too small.

If you want to read more thoughts on how to hire right for a startup I’ve got a few thoughts here (and a bunch of links at the bottom as well). At TOMO we’re building tools that automate paperwork, starting with things like the IRS W-9 Form. This is just the beginning — make sure to follow our journey.