Teams should be agile enough to iterate quickly based on what analytics tells about how users behave. But it’s hard to teach or define art and creativity which is why most software apps tend to end up looking like each other.

Our General Counsel would frown upon me saying this but the truth is I like working with younger engineers for front end and UI / UX design work. The principles of mouse-click reduction, the psychology of stepping outside yourself for user perspective, etc. still have to be acquired but they’re not as encumbered by previous products they’ve designed/learned. They’re more apt to create a novel workflow that takes a user to their destination with a higher level of intuition and delight over existing products. This is especially true of consumer applications but I see it increasingly in B2B as well. I just wish the millennial generation would stop making ridiculous statements as if they were toned like questions – “Um, I don’t like morning conference calls?”

For back end and database engineering however, I would much prefer an experienced person. Married guy with children – I love you. Frequent front end design mistakes and iterations are cool, but back end issues will keep you up in the middle of the night.

I was up in the middle of the night a lot.

Hey ladies, meet me and my brooo.

The other night our best sales guy called me wanting to figure out how to establish an enterprise sale with a medium-sized medical technology supply company. I wasn’t quite sure what the fit was but he was insistent we find a way (uber tenacity is part of his charm).

The next Sunday at brunch we were having our usual Sunday get-together when a group of guys approached us (see real pic above). The lines they began to throw down were so cliche (sorry guys) it made me think back on that potential enterprise sale.

Our own pitch to the enterprise company was probably going to come off just as cliche and generic. Something like, “Hi _______, you know, as social media in healthcare grows, DoctorBase has a solution that <insert feature ramble here>.”

Hypothetically assuming -

I’m an enterprise, especially one with deep pockets and a wide distribution channel, I’d probably get approached by startups a lot. And like most startups, they’d begin pitching me the wonders of their technology with brochure-talk of product, completely oblivious to -

1) My role in the enterprise. It’s a large company and there are multiple stakeholders other than the bottom line. So, what’s in it for me? I care about the company I work for and their profits, but I care about my job and my success internally as well. How are you going to make my life easier in the department I work in?

2) How would I realistically adopt it without massive disruption to my salesforce, channel or support teams? Do you even know what I have to do each day to get things to work around here?

3) Even if I bought your product or partnered with you, how would it affect the other divisions or departments in my company?

Armed with this newfound inspiration we researched the enterprise heavily and the managers of the different divisions on LinkedIn. We mocked a flow for our preso like this -

A) What was the economic momentum of the company? It turned out they were pursuing a loss-leader strategy in the U.S. market and were losing money heavily – primarily in the national salesforce they had hired.

B) What marketing were they doing now? Using social media monitoring tools we picked up comments from distributors in that vertical that indicated ineffective marketing. We found one quote on a forum (which we screenshot) that said, “This company must be spending a lot of money on marketing. I see their brochures in the trash bins of a lot of dental offices I go to.”

C) What would the mechanics of our partnership look like? We wanted to show our audience at the enterprise that they would look like visionaries to their CEO and the rest of the industry, and that the different departments (marketing, sales management, customer support, legal) could be easily shown why they had a stake in the new project.

Once we could answer and flowchart A, B and C above – we started to craft our pitch. It ended up going from -

“Hi, I’m _____. I want to tell you about an amazing new…..”

to

“DoctorBase has a solution to leverage social media to turn around your retracting sales efforts, make you look like a rock star and help sell the different departments on why they should buy into your idea of partnering with us.”

We may still not end up having them date us, but at least we’ll come with an approach that will leave the door open for a friendship

* Sorry guys in pic, I know this is kind of harsh. But you’re wearing matching baseball caps worn backwards while delicately holding mimosas.

The chase for money often leads to a brick wall

During a lunch with the partner of a medium-sized venture fund back in the mid 2000′s, I was talking excitedly about how Voice over IP and the Cloud was going to “revolutionize” call center technology. Admittedly, I was full of hype in my youth. The VC waived his hand and said, “John, software companies are successful because of marketing and capitalization. Not technology.”

Over the last few years I’ve found this to be true on purely statistical levels, but while the startup industry can be analyzed as an aggregate of statistics, the individual success of a startup is really about the psychology of its people.

If money is the primary psychological driver for why the founders are in a startup, the chances that they’ll survive the fluctuating funding environments and all the ups and downs of the entrepreneur journey are slim.

IMHO the culture of the organization will be better suited for the long term if the thinking is -

“What the f*ck else could we do?”

A lot of the entrepreneurs whom I’ve spoken to that have more than one successful startup do their own gig not because they think they would make a lot of money (though they desperately hope to) but at their core – they didn’t think they could do anything else. Not creating exciting products with their smart, creative friends was an existence they couldn’t imagine. Quite simply, it was the thing to do because it was the only thing to do. Nothing was optional. There was no corporate safety net to fall back on if things failed.

But if the motivations are to “Drive Ferraris, date hot people and tell the world to go f*ck themselves” – that’s the culture that tends to grow as the company gets bigger, and the propensity to abandon ship when things don’t go well always loom. Concurrently, the management thinking becomes very linear – market, raise money, market, raise money…. Liquidity event!

Even if this turns out well for the team financially (and sometimes it does) it’s not terribly exciting. Trying to change an industry, change people’s behaviors, or even take down a corporate giant – that type of focus not only has a higher chance of success, the road looking back will be a lot more fun.

God's waiting room awaits the foolish and young

From conference to conference, we all hear people say this.

But wouldn’t the folks who say stuff like this rather be waiting for the next great feature to be built, to then wait on getting a new customer, so they can then wait on getting revenues?

Because if they can’t wait for that, they can wait for funding. And they’ll be waiting a while.

Chances are, you're the monkey too.

As startups grow there come inevitable points where stressful times meet the dynamics of group psychology. During these lows, it’s  common to hear some people gripe or complain -

“I have no faith in this management team.”

The only problem is, in companies that are 25 people or smaller, everyone is essentially in management. What they’re saying is that they have no faith in themselves. The English have a word for that – loser.

Don’t be one.

Strategy Meatball is a good recipe for Strategery Spaghetti

Every growing startup has people approach them or interview for a job interested in “doing product marketing” and/or defining “growth strategies.” These folks range from fresh out of business school or on the heels of having taken some time off after the last startup they were a part of (as early employees, almost never as the founding technical people) had a liquidity event.

Tell them to go f*ck themselves. In a nice way, of course.

These people will not only waste your time, in a startup that is sub $10 Million in revenue, they will require additional resources to get their “ideas” off the ground. Read: hiring more people, consultants, expensive B2B intelligence apps, eating the time of the sales team, creating documentation no one will read, etc.

At the end of the day, they become the ones winning in the relationship – because they got to learn on your time and dime. And for some reason, they have a propensity for politics and blame games when things do’t go their way (they won’t).

Unless they can code, sell on the phones or generate leads, avoid them at all costs.