The Case For Autonomous Commercial Commerce

My day begins sitting atop a 36’ Hunter sailboat listening to Channel 16 radio chatter from the iconic San Francisco Bay. It was a bluebird day with a light breeze – a perfect day for writing. As we near one of the most active commercial shipping zones on the West Coast several gargantuan cargo ships steadily make their way into port to be unloaded. Small sailboats weave around them, careful to avoid their tremendous wake. Overhead, the faint buzz of jets can be heard; their bodies full with passengers and cargo as they crisscrossed the sky.
We live in a technology enhanced world. Our cargo ships and cruise liners pilot themselves over vast swaths of seas, our planes fly themselves once airborne, and we’re all walking around with miniature supercomputers in our pockets. Commerce is bustling. The world is growing, evolving. 
I get back to my motorcycle and make the drive back to a friend's place across the bay. Hopping on the freeway I pass a congestion of yawning, day dreaming, phone checking cars and long-haul trucks, everyone eager to reach their destinations and be done with the monotony of their commute. 
I reflect and then ask the question: In an era in which planes carry hundreds of passengers through the sky, and cargo ships transport tens of millions of dollars worth of precious cargo through choppy seas, both relying heavily on autonomous piloting for expansive stretches of their journeys, why are our road systems still plagued with a driver system not remarkably different than that of the early 1920’s?
The Story of Suzanne & Jennifer:
Our fictional truck driving character, we’ll call her Suzanne, is tired. She’s been on the road for weeks, each day logging just under 11 hours, the maximum permitted by federal law before she’s required to rest for 10 hours. Her eyelids sag heavily, her jaw is slack. The road undulates in front of her; thousands of miles of sameness blur in the front of her mind. The rumble strips scream to life as she drifts slightly off to the side for the hundredth time. The brakes flash red. She shakes herself a bit, polishes off the final few sips of burnt gas station coffee and presses the gas pedal. Afraid to be penalized for going over hours, she pulls off into the next truck stop to get some rest. She drifts off to sleep under the familiar neon glow of the truck stop thinking about her family and wondering whether or not she’ll have a load to haul on her long journey home.
Not everyone makes it to the truck stop. In 2013, 95,000 people were injured in accidents involving commercial trucks, with 3,964 fatalities. But Suzanne is not our villain here. Antiquated driver technology is.
Our fictional supply chain executive is Jennifer. Jennifer’s 2014 Company Charter is to move their goods faster, for less, and to materially improve the company’s environmental footprint. Each year she’s responsible for coordinating the movement of their goods across state highways, an effort which collectively racks up hundreds of millions of human-driven miles per year. In the face of growing consumer demands and radical eCommerce growth, Jennifer’s fictional employer MallMart has put the hammer down on Jennifer and her team, asking her to squeeze any and all juice out of their existing logistics program. More trucks, more hours, more routes, more efficiency. Each request making less sense than the last. 
She thinks through their asks and her options:

  1. “More Trucks,” presents a huge upfront cost, coupled with increased ongoing maintenance and insurance costs. 
  2. “More Hours,” are not possible as federal regulation (the FMCSA) strictly mandates drivers to a maximum 11 hours of consecutive driving before a requisite 10-hour break. 
  3. “More Drivers,” are increasingly hard to come by, with a national shortage of over 30,000 driver jobs, as reported last year by the Council of Supply Chain Management Professionals’ State of Logistics Report.  

As it stands, both driver and employer are hard pressed to make progress; stuck in a stagnant, technology starved industry.
Enter the Case for Autonomous Commercial Commerce:

  1. Big Business is hungry for a more efficient, safe, and modern means of overland logistics. 
  2. Drivers are hungry for their profession to be brought into the 21st century – for them, this would mean fewer empty loads (technology-enabled logistics), and a much safer working environment (autonomous rigs).
  3. Technology has been empowering other key modes of autonomous commercial transit safely by both Sea and Air for years.  

Who will step up to the plate? Will it be the technology giants like Google or Apple, or will the automakers themselves be the first to take the leap? 
If I was a betting man (and generally startup biased), I’d say we’ll first see something like this arrive out a garage somewhere, and see it catch on from there. 
Either way, the time is now. 
This post is an expression of my own personal thoughts and is in no way related to that of my employer, Glider.

Re: Technology

When I was just a boy I was imminently close to successfully bending space and time.

Sitting in the basement of my mothers Northern California home I had all of the essential ingredients. My workshop smelled of freshly cut wood and had dissected electronics strewn about the floor. I was likely seated Indian style inside of my spaceship - a full-size refrigerator box wired to the bleeding edge of what was technologically possible for the curious mind of 7 yearold. The internals were illuminated by strands of christmas tree lights. A keyboard sat in front of me, dissected motors, fans, and switches of all types and sizes carefully embedded in the cardboard walls. I would sit down there for hours. Imagining. Dreaming. A daily rush of possibilities and excitement seemingly in endless supply.

Then one day, building RC cars became cool and girls no longer had cooties. Over time my workshop collected dust, and the inventions of my childhood were disassembled and discarded. Life went on.

The feeling of unbridled curiosity and the belief that nearly anything was possible fell by the wayside and was replaced over time with “reality” -  a boxed up justification for rules, growing cynicism, and explanations for why things are the way they are, not the curiosity as to why they’re not, or what they could be. 

A few months ago I stumbled across a blog post by Braintree founder Bryan Johnson containing a few lines that (within the context of the rest of his article) shook my world, and momentarily transported me back to my glowing refrigerator-box time machine. 

"The United States space program of the 1960’s captured the imaginations of an entire generation. How many children from that era dreamed of becoming astronauts when they grew up? 

What will today’s children dream of becoming?"

Read his entire article here. It’s well worth the six minutes. 

What will today's children dream of becoming? My scribbles here and elsewhere are dedicated to exploring the limitless possibilities and exciting times we face today as technologists and practitioners both in software and hardware enabled fields. An attempt to re-ignite for me and hopefully for others, the type of thinking and action, however small or large, that we once explored without bounds as curious, hopeful, and ever optimistic children flipping switches in our refrigerator-box time machines. 


Measure & Question Everything

This almost was broken into two separate posts, but since they’re so related we’ll just roll with one broken into two parts.

On Measuring:

If you're not measuring everything that you do as a company, you're doing it wrong. In fact (IMOP) - if you aren't measuring it, you might as well not be doing it at all. 

Why? Because when people speak generally about performance, they do two things (usually unintentionally): 

  1. They miss out on identifying key patterns. Frequently these things are subtle and only manifest in single digit percentages. 
  2. They avoid facing evidence certain key stakeholders or programs may not be performing to expectations. 

Almost more important than the negative side of neglecting measurement, is the upside to measuring early and often:

  1. Cuts down on meeting time.
  2. Aids in communication, and is the easiest way to end petty team arguments.
  3. Helps guide decision making between founders or key stakeholders.
  4. Helps to avoid budget waste.

So invest some up-front time in setting up systems to measure: it's worth the time now and will pay off in dividends down the road. 

On Questioning:

Towards the end of an evening recently, a mentor and I honed in on on the topic of SaaS Metrics. At the time, I was MQL obsessed. 

Me: “We just kicked off a big new marketing campaign and we’re seeing amazing growth in our MQLs"
Him: "Great - how do you define an MQL?"
Me: (feeling good about my answer) "In our case, an MQL is a CFO, VP Sales, or Sales Operations Director at a technology company between 100 - 500 FTEs."
Him: Good to hear. How many of your MQLs have converted to sales?
Me: <insert pathetic single digit percentage conversion rate here>
Him: So for the X% that did convert, what did they do differently than the rest, and why aren't you tracking and optimizing for that?

AHA* - now we're on to something. It sounds stupid and obvious now, but when you've been dead set on seeing a certain set of metrics perform - and have been throwing tens of thousands of dollars into spinning up their support systems, the blinders inherantly go up at some point. 

The takeaway is two-fold:

  1. Constantly audit your metrics all the way through to final conversion. Don't set it and forget it.
  2. Having X,XXX MQLs/mo felt and sounded great, but you know what's better...? In our case it was dropping the MQL obsession in favor of having XX SRLs/mo (Sales Ready Leads) that were 80% more likely to turn into sales. 

These changes in metrics don't have to be huge. In the case of our MQL to SRL shift, the only difference in qualifying characteristics was that an SRL was an MQL that requested a demo. 

What made a much bigger difference, was realizing that our current content marketing plan was not pointing these leads in the directon of a demo.

Most of the time the devil is in the details– so take the time to sort through things before putting budget behind campaigns, and be obsessed with full (through) funnel conversion rates. 

The Instrument Panel: Starting and Running A Company

I was drinking bourbon with a friend of mine who runs a company in town (~200 FTEs), and at some point in our conversation, a visualization came to mind of what it’s like to start and begin to scale a company. I thought it would be fun to try to sketch out the concept that came to mind.

The key idea behind this is that if you boil companies down to several stages of growth, there are only a handful of things that actually matter. It all becomes about the ability to focus. 

*The drawings are supposed to represent an airplane cockpit, but I suck at drawing.*

**(It’s important to note that these illustrations are only examples. Every company has its own core metrics that matter. Sit down with your team and figure out what these metrics are and then fill in the blanks. Additionally, I'm coming at this from the viewpoint of a CEO reporting to his or her board. Sure, there are other things that matter that ultimately support some of these higher level items, but those won't necessarily be brought up during performance review and can be delegated to others if need be.** 

At the "Birth Stage" there are only two things that matter, 1) you have cash in the bank, and 2) you're building product. Anything else is noise. 




At the "Seed Stage" there are only three things that matter, 1) you have cash in the bank, 2) you're building product, and 3) you're signing up customers. Anything else is noise. 




At the "You're a Real Company Now Stage" there are at least nine things that matter, 1) you have cash in the bank, 2) you're on top of your product backlog, 3) you're signing up customers, 4) you're tracking and improving your Lead Velocity Rate, 5) you're tracking and improving your Marketing Qualified Leads, 6) you're tracking and improving your Sales Ready Leads, 7) you're tracking and improving your Customer Lifetime Value, 8) you're tracking and improving your Cost to Acquire Customers, and 9, your Average Selling Time doesn't scare off sales reps :). Anything else is noise. 


9 Steps to a Killer (and free) Content Marketing Program

This post is all about how to build brand, distribute genuine content, and land highly targeted leads for free. Not only that but this strategy will scale, and it only takes your time.

This is the same strategy that we put to work in 2013 at Glider, and the results have been great. 

Before we dive deep here's the TL;DR.

TL;DR: Google will help you uncover several "Top XYZ of 2013" lists where you can identify vertical-specific industry experts. Personal flattery via LinkedIn messages will get them to listen to you, and finally, an opportunity for them to be quoted on your blog will tie their name and syndication to your brand. 

There are four facts that this strategy relies on:

  1. People always want to improve themselves (look/sound/do good).
  2. One of the best sources of endorsement (just behind customers/friends) is from a recognized and impartial thought leader in your given space.
  3. At the end of the day, people love to hear the sound of their own voice. 
  4. Flattery still opens doors.

Ok, now on to the step by step guide. Feel free to leave any questions down in the comments and I can elaborate...

1. Get on the Same Page
To kick things off: Content that doesn't quote an industry leader, brand, or some other voice in your industry is throwing away opportunity, time, and money. If your content pipeline doesn't have room for expert opinion in the form of a quote, contribution, or guest post - reconsider your content pipeline. Do we post articles without third party contributions? Sure, but they don't do as well as the content that does. 

2. Build your Influencer Lists
Now that we're on the same page, go fire up your browser and run a search that looks like this: "Top ______ leaders of 2013." The blank should be filled with the title of your target buyer. In our case we ran three seperate searches, "Top Sales Operations leaders of 2013, Top CFOs of 2013, and Top VPs of Sales of 2013." Now do this for the past three years and create an excel spreadsheet documenting names, companies and sources. 

3. Templates
It's time to put together a master template so you don't waste too much time on outreach. Here is what our template looked like:

"Hi John,

I'm reaching out because we're looking to include a quick quote from a Sales Operations thought leader. It looks like you've been doing some great work over at Acme Corporation - congrats on the award last year. 

I know you're busy, but if you'd like to contribute a quote, we'd be happy to include it in our piece next month.


The messages can be cookie cutter - just make sure the names, roles, and companies are correct :) 

4. Outreach
This part takes some time. You're going to go to LinkedIn and friend request each of them. In your "Friend Request" you'll paste in the template you created in Step 3. *Pro-Tip- TextExpander is free and will make these templates less of a task. 

Send as many as you can up front. You'll be waiting out many of these responses for weeks, so better to start the waiting now. If you're good (like our talented content writer, Elaina Ransford) you'll hook a few in the first 5 days. Some of these have taken months to groom for participation. 

5. Build
Rome wasn't built in a day, right? Neither are these relationships. Start slow, ask small. Build a rapport with these folks, it's going to be a long ride. A quick 2 line quote is an easy first ask. Whatever you do, don't ask them about your product. Make it very general. What do they like to write about? Ask them for a quote on a topic you know they like discussing (YouTube may help here). Tell them when you expect the article to go-live, and that it will be published on the company blog, in whitepapers etc.

6. Their Turn
This step is the most important. Up until now you've done a few things well: 
1) You've built your credibility by attaching their better-known brand to yours, and 2) You've started to get them invested in the success of their quote. 

The day you're ready to post (or the day before) send them a preview of the article. Give them an opportunity to suggest any changes etc (now you're getting them invested in the entire article). Tell them you'll send them a link to the article once you publish it "sometime around 2p today" in case they want to share it with their colleagues. 

7. The Golden Share
You've got them engaged, and now without any pushing and zero budget, you landed a quote, and a shout out (tweet etc) from an industry leader. Also, since you're friends on Linkedin, and because your blog auto publishes to all of your employees LinkedIns (you've set that up, right?) the contributor will likely “like” or share the article which will then put it in front of their entire professional network. Boom.

8. BFF's
You're friends now–  they've contributed, you've thanked. Everyone feels good. In your followup email make sure to let them know how well the article did and that you'd love to include them in future pieces if they're interested. In fact, now might be a perfect time to mention that upcoming white paper a few months from now that they might be interested in contributing to. Nothing soon, but worth mentioning. This should all be done by phone if possible. They like hearing their own voice, but they also like knowing you have one too. 

9. Success Compounds
You can see how this just continues to get better with time. As you develop your program, it may make sense to start spending small - an intern to run outreach under your name, a content writer to work on the posts, or at best someone who can do all of the above in their own name. 

Good luck, and ask questions. 

The Cost of Free

In enterprise, the cost of free is perception.

Perceived value is – at least up front – everything. It is the push required to get a prospective customer to sign up and trial– to take the time to find value in your product.

Free is great– it dramatically lowers the barrier (cost, approval, time to activation, etc.,) between a prospect and your products value. In many cases, this is where the market is headed. It's the world of SaaS, BUT it is important to understand that there is a HUGE difference between a free trial and a free (or cheap) product.

In our early days (still living them), it happened time and time again– until I saw the pattern. You land a meeting with a C-Level exec at a F500-2000. They’d love the product, the timing would be right, they were ready to get started:

"So how much does it cost."
"Well, your first month is free, but I'd like to include you in our 3-month pilot program."

And that's that. The interest would disappear in an instant. Why? Because surely an enterprise grade, solve-all-of-our-problems product is worth more than free, even for a trial. As soon as I started asking for money - real money - my results improved.

"So how much does it cost."
"Well, normally it's $XX,000 per month, but I'm willing to work with you at $X,000 over the course of a
3 month pilot program while we ensure you are successfully on-boarded." 
"That sounds reasonable, I'll talk with our CXO about next steps."

Now we're talking.

Free is great, but make sure you're using it properly. 

Enterprise customers don't want free, they want a clear return on investment, support, and uptime. Charge them for it, they want you to. 

The Power of The Whiteboard

We all love our tools. 

Google Apps, Evernote,, Intercom, Mixpanel, Base, Glider. 
I'm not sure what I'd do without any one of them. They help me keep all of my data contained, searchable, and relevant – but around 3p every day, none of them can help me. 

We all know the 3pm slump. Your previously consumed lunch is now suggesting you take a nap, your inbox continues to distract, and you're now torn between any number of pseudo-meaningful, but-not-necessarily-priority tasks. Drat. 

None of your compu-tools can help you, and switching between them to find the right thing to work on becomes a distraction in and of itself. 

Enter the Whiteboard. 

There's something beautiful in the simplicity and power a whiteboard with a few self assigned tasks can hold. 
You don't want to let the whiteboard down, because in effect, you're letting yourself down. With a few tasks on a whiteboard, you now have the opportunity to have several daily wins, even if they are all smaller pieces of a bigger goal. With a whiteboard, you're a closer.

At Glider, the whiteboard is just as much a daily tool as any one of the aforementioned web apps. Every morning at 9:15 we host a get-to-the-point standup where each team member writes out their top priorities for the day– the things that in their own mind must be completed or seriously underway by beer-thirty. Ten minutes later, everyone has a list for which they can hold themselves accountable– a list that provides that simple reminder when the 3pm slump rolls around and you forget what really matters. Ever since rolling out these whiteboard stand ups, the number of "what are you working on today" office conversations have dwindled.

So give it a shot– starting next Monday, write out all of your daily goals on the nearest whiteboard (make sure they are all actionable, non-menial tasks), and keep it in your line of sight throughout the day. Each day, put checks next to the tasks you've completed the day before, and add new tasks for each new day. At the end of the week your whiteboard will look more like a trophy than that once ignored blank canvas. 

I'd love to know how it works for you. 

When Raising Money, Notes Come Second

Ten months ago, venture financing was as foreign to me as crocheting. 

You start with some yarn (or something like that) and then using some stick things you end up with a scarf (or something like that). For financing you start with a business proposition, you find some investors, and out pops a check.

Fifteen angel pitches, and twenty-seven venture pitches later– I now know that raising money is in fact much more complicated than crocheting (or perhaps more accurately– at least you don't need an attorney to help you finish that scarf). 

The goal of this post is to establish a simple mental model that should save any first-time entrepreneur some significant time and headache. I'll try to keep most of this pretty high level because there are tons of great resources out there once you're ready for a deep dive (Venture Deals). 

A few upfront disclaimers: 1) I am by no means- an expert, just a first time entrepreneur with some air miles under my belt that I've come to learn are worth sharing. 2) Everyone's venture is unique, what has worked for me may very well fail to work for you. 3) Don't' ask me for introductions to our investors– it's tacky, and if I think what you're working on is interesting they'll probably hear about it at some point anyway.

It gets pretty wordy down below so for the sake of brevity here's the TLDR. 

TL;DR - Understand how priced financings work before trying to wrap your head around convertible notes. Because notes convert into your next priced financing, there's a lot of early decision making that you'll have to leave up to your attorney and investors if you don't understand how priced offerings work. Think of this time spent up front as a personal investment in your company, as it will give you the foresight to optimize for future rounds. 

Here's my attempt at a "quick," plain English breakdown of what all of this actually means. 

Nowadays (generically speaking), when you go out and raise your first slice of capital, you'll do so on a convertible note. 

Notes are used at the earliest stage of financing to create a certain amount of flexibility for both entrepreneur and investor. It creates flexibility for the entrepreneur by not forcing the investor to determine the value of the company at a stage that generally would return unsavory results. AKA, if you're a team of smart guys/gals and you're raising money pre-product, it might be fair to say that your company is worth less than $1M on the open market in its present state. Assuming you're playing the VC game, and aim to build a $100M business, it would be lame to give away a huge chunk of your company for a small sum of start-up capital… Enter, "The Convertible Note." 

Casually speaking, what is a Convertible Note, and what does it mean for my company?

A convertible note is a document that promises the issuance of shares upon the closing of a future issuance of stock (Qualified Equity Financing or "QEF"). When you sign a note, shares are not actually priced and issued to the investors, but rather held until the price has been set 6-18 months down the road (again, generalizing). Once the price is set, the note will convert into stock at the price deemed at the time of the QEF subject to any Note Cap, and/or Discount. 

Instead of forcing the investor to price the round, a convertible note allows the investor to place an early bet, cap his risk, and receive a discount towards future investment. The "Note Cap" acts as a security blanket for the investor so that he or she is guaranteed to take a minimum stake in the company as deemed per the Cap. If this is your first go-round, and you don't come from some sort of world class tech pedigree, you'll almost certainly be working with a capped note (though sometimes you do see uncapped notes flying around). 

Expanding on the example of this pre-product company raising money on a note, the investor and entrepreneur might set a cap of $4M pre-money, basically stating that no matter what the priced valuation ends up being down the road (maybe you blow up and your next round is priced at $15M), the early stage investors will convert at the capped $4M valuation rather than the rest of the investors at $15M. (This is the upside of a note for investors that I referenced earlier). This is also generally subject to some sort of discount so they'll end up with a bit of a spiff off the top. 

THAT SAID, I didn't write this post to explain what a convertible note does, I wrote this post because I believe that before you can truly understand convertible notes, you must first understand priced financings. 

A priced financing is when you and an investor agree that your company is presently worth $(X)M pre-money and based on that number, and the number of shares outstanding, the investor takes Y shares to equal Z% ownership. It's pretty straightforward.

A simple example of this: let's say I want to invest in an apple. I agree with the shop owner that this apple is worth $2 pre-money (pre-money = before I make my investment). I then decide to make a $1 investment in the Apple, and as a result, I now own 33.3% of an apple that is now worth $3 (post-money).

It's important to bear in mind that investment has just as much to do with Control as it does with Ownership. Generally speaking, these are the two dials that get turned when negotiating a term sheet. 

SO HERE'S THE RUB: If everything that you agree to in a Convertible Note, ends up translating into a certain amount of ownership and control once it's mashed up with the terms set in a QEF 6-12 months down the road, wouldn't you want to know what those terms might look like, and how this present note will effect the future round?!? 

I think the answer is yes. I think everything written above becomes MUCH easier to understand if you first wrap your head around what a priced financing looks like. More importantly, you'll be able to make smarter decisions re: early negotiations. So do yourself a favor– go read Venture Deals, learn a bunch about equity financings, and then go kick some convertible note ass.  


What Startup Founders Can Learn from Vintage Motorcycles.

At some point, shit is going to hit the fan. It always does. Sometimes in a life-jarring way, while other times merely a road bump. 

Let me start with a story.

It was raining pretty heavily as I slowed "Charlie" my 1972 BMW motorcycle to a stop behind some heavy traffic. I had a billion things on my mind. A mental check list if you will, starting wi – – – out of the blue my horn just started going crazy. Erratic honking mind you, while stuck behind a line of stopped cars. Immediately embarrassed, I shut Charlie off to make the noise stop. After giving him a few seconds to settle, I gave the key a twist. More noise. I was completely thrown off. Distracted. What the hell could be going wrong? In an instant, my to-do list, my day of focused productivity, all out the window. The only thing I could think about was my motorcycle horn, and how annoyed the drivers around me must have been. 

The horn issues persisted for a day or two before things returned to normal. Charlie was relegated to the garage while I let him, and my confidence in his electrical system cool down. 

Fast forward to last week. It was pouring down rain. I was nearly home when the familiar high pitched horn kicked into gear without permission. Only this time, my reaction was different. In a split second, I acknowledged the fact that the horn was not going to stop by way of killing the engine, swearing, or tinkering with the wiring harness. Nope, Charlie was wet, and as such the horn would not stop shorting until the wiring had a chance to dry. I accepted the situation for what it was and continued on with my day. 

A silly story, yes. A poignant analogy, I hope so.

As entrepreneurs, success is underpinned by our ability to remain focused when shit hits the fan. One of the most surefire ways to ensure you'll do this is to learn from these road bumps, so the next time they crop up– everything is that much easier. And they will crop up. If you don't know what I mean, you're either lying to yourself, or not pushing hard enough. So pay attention to your mistakes, do post-mortems with your team when the hard lessons crop up, and be that much more prepared the next time shit hits the fan.

Don't Build a Hammer

I learned this one the hard way, as I think most everyone does. 

We're entrepreneurs, and as such, we see problems as opportunity. We evaluate the competitors, total addressable market, risk etc., and then propose what in our minds is the perfect solution.

It's beautiful. It's a hammer. It's handle - so ergonomic, it's weight - balanced to perfection, its color - inspires accuracy and power. No one in their right mind would ever use one of the hammers that exist today over ours. This hammer- it's a no-brainer.  

We get ourselves pumped up, and after collecting "enough" data we go heads down to build "a thing." In no time, our obsession has shifted from being focused on a problem to being focused on our solution.

You see this all the time. How many entrepreneurs walk you through their sexy Product X demo, but then get squirrely once you ask them what problem they're actually solving? In their quest to build a great product they've become completely detached from a real problem. 

Be obsessed with helping people drive nails through wood, not building a hammer.