Monthly Archives: February 2016

Confidence and Insecurity

They say that confidence is quiet while insecurity is loud – I think the internet shows this all too clearly.

The problem is that the internet rarely showcases the “quiet” much at all – it’s like we’re interfacing with a spectrum of insecurities from those that yell and shout all the time and those that do it on occasion (I wonder where I sit…).

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Weave: Concierge Networking The Way It Should Be

If you’re like me then you’re probably trying out new products and services and apps all the time.

Whether it’s for personal or professional needs isn’t the question as these things tend to blend together more and more these days, but it’s just fun to see what everyone else is building and to experiment with new forms of technology and user engagement.

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On Accelerating the Inevitable

Images via Bossfight.

It’s a tough business being a startup, you know? Most of the world has very little idea of what it takes to get something significant off the ground and the amount of energy required to move at an incredible velocity (and sustain it). The physical, mental, and emotional hurdles that must be overcome every single day is nothing short of exhausting.

And it requires enormous, herculean-levels of effort. Sometimes this is displayed through marathon coding sessions for days and weeks on end; your fingers and hands brittle from keypresses.

Or sometimes it’s displayed through discrete key decision-making moments, like hopping on a plane at the last minute for the chance at meeting someone important or to score a huge game-changing deal. The startup landscape is littered with these stories and a select few may eventually become the stuff of legend (or at least a great story).

And let’s not even start with capital and fundraising — the consistent rejection notices can be tough to swallow even when your pitch is seemingly flawless. I don’t think I’m alone here, but, since your startup venture is very much your life and consequently, your identity, the dismissals can feel deeply personal and hard-hitting — it can feel as if they have rejected you, not just your crazy idea.

(By the way, if you’ve figured out to create powerful mental boundaries and somehow isolate these emotions objectively, I’d love to know your secret…!)

But you press on, you have to. Otherwise it’s probably better that you quit now than spend another moment doing something you don’t really believe in, right? No one likes to waste time.


Steve Jobs.

Steve Jobs is one of my heroes and I miss him a lot. The biographies and movies have attempted to do him justice but none of them, at least for me, have captured the essence of who he was and what he was able to do for not just an industry but the world. I’m an unabashed fan.

In the same way, I’m enjoying the very rare and unique opportunity to watch Elon Musk do what he does. Steve’s passing brings context and perspective to this opportunity: You see, we all get to to observe a person who is entirely committed to a future vision, a vision much bigger than what any of us could ever fully appreciate, comprehend, or create.

Said another way, I feel fortunate to watch a man move an entire industry forward, to fundamentally change the way that we act and behave, and to experience the raw power of technology grossly applied. I “missed” a lot of those moments with Steve and I’m committed to not miss those with Elon.

And this isn’t because I necessarily want to be Steve or Elon or Bezos or any of the many incredible business leaders that we have among us — I just want to enjoy the opportunity to watch the very best that we have do their very best work and, perhaps, glean a few things from them as they perform. If I can pick up a few scraps from their proverbial table of genius then I imagine I’d be better off for it.

A few years ago Elon gave a talk at Stanford and he spoke for nearly an hour about his thoughts on Tesla, SolarCity, and SpaceX. There was a lot that was great and it’s definitely worth a listen, but there was a moment that really captured my heart and my attention.

Elon first shares a quick thought about conviction and if you weren’t paying complete attention you’d miss it — it almost feels flippant and understated:

Yeah, but, I just thought that these things needed to get done and if the money’s lost, okay, it’s still worth trying.

You could probably sit all day on that comment and then, if you’re brave enough, you can dare to ask yourself the extremely difficult question about whether or not you are doing something that you feel needs to get done.

Are you? Do you feel it deep in your bones? And are you willing to put it all on the line to see it become a reality?

It’s always a bit disconcerting to realize that most (if not all) of us know whether or not we are doing what we’re supposed to be doing. Most of us know, in our hearts, whether we’re wasting our time or whether we’re executing against the things that we were meant to be doing — we can easily deceive and lie to ourselves about those things but in our heart-of-hearts we know the real truth.

Elon Musk doesn’t stop there though — he shares his vision for what the future will hold and why he feels so strongly about where he is leading his team at Tesla:

I mean, I think there’s a fundamental good that Tesla can accomplish — the acceleration of the inevitable, which is electro-transportation.

Elon believed, way before most of us every did, that electro-transportation was not just a possibility for our future but an inevitability.

Tesla, with Elon’s leadership, would get all of us there faster (and we’d all benefit from it).


Elon Musk

During the toughest moments of building my last company I had to hold on to the very few-yet-important and fundamental truths that allowed me to continue to put one foot in front of the other. And I’ve been starkly reminded with my current company building efforts that this is the only way startups not only prove that they are, in fact, a real startup but how they transform into world-changing companies.

At TOMO, we believe that a truly paperless world is inevitable. As technology increases and our gravitation toward more complex and deeper use of computer automation is adopted, it just makes sense that the manual processes that we experience today will become a part of history tomorrow.

We also believe that the road toward obsoleting paperwork of all types (e.g. hiring and employee administration, financial documentation, physician and patient intake processing) is a long and difficult road, both technologically and in terms of gaining mass acceptance.

Everything should be like this.

The appeal isn’t difficult to capture, explain, and enthrall those who will listen — I mean, who doesn’t want to be able to walk into a doctor’s office and instantaneously completely any and all paperwork as simply as Apple Pay or Google Wallet?

With the click of a button all that paperwork should just be automatically (and magically) completed. This future isn’t hard to imagine and we’d all love for it to be true.

But, unfortunately, not as many understand the distance that needs to be covered and the gigantic gaps that need to be filled in order for that inevitable reality to become true. I imagine Elon faced the same type of challenges and questions:

So… Elon… how are you going to do that?

How” we’re going to get there, for many people, is just too difficult to assimilate into something cohesive and understandable. I mean, when you’re building something that no one has ever really done before there are, by consequence, no existing models for you to copy or borrow from! That’s a tough mental hurdle to overcome, even for the craziest of entrepreneurs.

Building a truly paperless world is a big idea, a really big one. It requires a huge imagination, an ability to see way beyond the current state of things. Like any good startup we’d love to work with and partner with those that are also able to see that future — they are few and far between. It’s easy to say that you’ll invest in “moon shots” and hard to actually do it.

This is why watching Elon do what he does with the vision that he has for the future is so encouraging. His history of self-financing his vision when very few people would is a testament to his long-term vision for what is now generally understood as inevitable — he just saw it decades before all of us.

With TOMO I feel the same way about an inevitable yet fast-approaching future. This gives me courage, resolve, and it breeds resilience when faced with criticisms and rampant doubt. Our efforts to automate human capital by utilizing blockchain technology is different, in every sense of the word.

But I’ve got my own personal horizon line — there’s no way that my 9-year old daughter, 7 years from now (when she’s 16), should ever have to manually fill out a I-9 and W-4 form via pen and paper to get a job; instead, those administrative tasks will be automated, magically, based on an idea and a technology that her father was proud to build.

We’ve just got to get there faster; I want to accelerate the inevitable.


We are accelerating the inevitable, a future where paper-based systems are obsolete. Follow our progress via our blog and twitter. We’re breaking things.

The 3 Types of Startup Pitches That You Will Always & Inevitably Give Venture Capitalists

Go big or go…

A long time ago I took a few classes that centered around public speaking — more specifically, homiletics, which is the art and study of preaching. At the time it wasn’t my intent to become a preacher or a pastor but I wanted to seriously level-up my expository skills and my ability to explain and describe a given topic and/or idea.

I needed these classes because, to put it lightly, my communication skills were about as good as a pimply-faced pre-teen asking someone if they wanted to go to the middle school dance (speaking from experience…): My delivery was broken, my thoughts scattered, and I stuttered a great deal, not to mention the fact that my hands could never really find a suitable place to “sit” as I talked. My professor said I was a “gesticulator extraordinaire” — I wasn’t always sure how to interpret that comment.

But ever-so slowly, I improved. I realized that the most helpful coaching, for me, was squarely centered around two distinct things, the first being a physical component and the second being a mental one:

  1. My pacing, which was directly tied to my ability to breathe and to not forget about breathing. I am notorious for getting so excited that I forget to inhale / exhale at a reasonable measure which leaves me winded and then everything goes downhill from there. If I forget to breathe it also means that I forget to swallow which contributes to massive cottonmouth which compounds the problem. You can easily imagine how this growing snowball leaves me pretty debilitated in my execution.
  2. My delivery was predicated 100% on my own sense of identity and the peace that I had about being myself. In other words, the more comfortable that I was in “my own skin” the better I could perform in the unique ways that only I could perform. When you first start out you attempt to copy and model your own speech patterns, styles, and delivery mechanics of people you admire and respect. The goal is to appreciate their distinct communication techniques and then quickly begin to discover and practice your own. This is easier said than done.

And so I was trained, received a ton of tough (but necessary) feedback, and eventually became much better in many of these things. I even worked with a breathing coach at one point in time to help facilitate a better connection between my thoughts and my body.

All of this was bolstered by a ton of practice as that’s really the only true panacea for public speaking and my mentor at the time required me to sign up for as many public speaking events as I could find. I went to them all hoping that I’d eventually become a master.

Naturally, of course, I never did, and that’s because there are a few things that simply never change.


All of them are related, all of them happen at the same time.

Invariably there are 3 types of talks (or speeches, lectures, sermons, and pitches) that you will give to other people. These 3 types of talks, as far as I can tell, never change and there’s nothing you can do about it — sorry.

  1. The Talk (Pitch) that you prepare to deliver.
  2. The Talk (Pitch) that you actually deliver.
  3. The Talk (Pitch) that you wish you had delivered.

If you’ve ever had to do any form of communication then you know exactly what I’m talking about. There’s the talk that you’ve been preparing your butt off to deliver, that you’ve sweated over (and perhaps even bled over), and that has cost you hours of sleep.

Then, when you get there, you give something different than the one that you had so fervently prepared to give — perhaps it was the audience (or one particular audience member) that changed things up (for good or for bad), or perhaps it was a mental hurdle that you couldn’t (or could?) overcome in the last moment, or perhaps it was what you ate for breakfast that threw everything to pot.

And then, after the event, as things have cooled down and as you’ve had a few moments to breathe and a bit of time to reflect on your delivery, you realize that there was a talk that you had really wished that you had given, that may have actually been different than the one that you had prepared for — oh, the irony!

The last one always hits me like a ton of bricks and I may even mutter something aloud as the realization pounces upon me:

“Dang, if I had only _______________!”

(You can fill in the blank based on your own experiences here.)


You know what they say about life and lemons…

I blew it. And, what’s worse, is that I knew it even before they told me that they weren’t interested in what I was building. The intro to this particular VC had been incredibly “warm” from a long-standing relationship that had a ton of relational capital built-upon it.

The institution’s portfolio was right up our alley and there were a ton of principally similar technical companies that almost guaranteed that they’d grok what we were building. They were excited (and I, doubly-so) about our pitch and they even moved a bunch of meetings around so that we could walk in a bit earlier in the week.

But for whatever reason (it could have been the carne asada tacos the night before…) I just wasn’t “firing” on all cylinders and whatever came out of my mouth just didn’t “land” as I had supposed they would. Blank stares and then, the death knell: One of the partners couldn’t help but mentally (and physically) disengage from our pitch and with a clever stretch-like maneuver unlocked his iPhone to check on some updates or email or whatever. Death.

By the way, to be clear, I’m not angry nor am I bitter — in fact, getting a ton of “No’s” is part and parcel of what raising venture capital is all about. I’m used to that and take it on the chin. This is what happens.

You know, sometimes it’s easy and sometimes it’s hard but it’s always stressful and full of anxious-laden nights. But most of that anxiety is generally unfounded as there are circumstances way outside of everyone and any one person’s control and, let’s be honest, sometimes, for whatever reason, someone could just be having a really shitty day.

But it doesn’t stop me from doing the math in my own head as I walk out of the building — what could I have done better, what did I say that could have possibly screwed things up, what could I have done to recover faster (or was recovery even a possibility in that scenario)? It’s all on the table for review.

You see, I inevitably begin to cycle through the pitch that I had prepared to give, the pitch that I had actually given, and the pitch that I wished that I had given instead of whatever “that” pitch was.

And even though I am familiar with this dynamic it still burns me up quite a bit, until I take a moment to pause and remember some very vital coaching advice from one of my business mentors…


This is probably a more realistic depiction of “pitching VCs” than most anything else out there.

One of the most important pieces of advice that was given to me when I first started raising capital for startups was to take every single pitch as a performance in which refinement was the goal, not applause.

In other words, my goal was to learn as much as I possibly could from the previous experience and apply it wisely and strategically to the next. In addition, I was learning to be more comfortable with not only the content of my performance but also the delivery mechanisms that were so important to manage and maintain. I was learning to pace and to become a bit more comfortable in my own skin.

Your pitch (and your pitch deck) is a constant work-in-progress, and it never reaches its “final” form — never is it truly perfected, only on the path towards perfection. Every single time you walk out on that metaphorical stage you have a new opportunity to practice your art, to become better at your pitch, and to learn more about what works and what doesn’t.

In the process you also learn a bit more about yourself — sometimes the first few pitches during a fundraising season (as they call it) is a lesson about self-confidence, self-respect, and courage.

And especially at the early stage, it is oftentimes more about you than your actual product or company.


At TOMO, we’re building the future of work by seeking to automate human capital. This blog post (and the larger publication) is about our journey on doing just that. Follow us on Twitter and subscribe to our email newsletter.