As the founder of a start-up and new app, I’m in the position of being in a brand new position over and over again.

Pretty much daily, in fact, like all entrepreneurs, I’m confronted with a barrage of new questions that require research, testing, intuition, and unforeseen obstacles that keep me up in the wee hours of night.

So many new things to learn, so much to navigate.

It’s those endless beginnings, however, those unknown situations when I’m standing on the edge of foreign terrain with no roadmap that keep me ...

We've all been there.

Sitting at our desk as this dark cloud of guilt begins to swirl — yet again — knowing that we're about to choose whether we're going to finish this one critical project at work or make it on time for dinner. Or a soccer game. Or any event that our families are counting on us for.

Do we fail the startup or do we fail the family? We're going to fail someone. Guilt is a constant, the only variable is the source of the guilt.

If this sounds familiar, it's because nearly every startup Founder wrestles with this problem on a daily basis.

We're not just working at jobs — we're trying to survive long enough to even get a paycheck. Everything we have is on the line, including the welfare of the very people we're running hom...

Founders, when we look in the mirror what do we see?

I don't mean that haggard shell of a complexion that looks like a time lapse video of decaying fruit. I mean do we look in the mirror, squint really hard through bloodshot eyes and say:

"Welp, that's it. Today's the day everyone is going to find out how big of a Founder fraud I really am!"

That's right.

Today's the day our investors find out we have no clue how we'd ever grow this company to an exit. Today's the day our customer calls us and says "There's no way I should have put my faith in you!" It's the day we finally admit to our staff that we were never 100% certain we should have told them to join this company.

Yep, today is the day that everyone reveals us for the fraud that we tr...

When I started my first company, we were operating on a bare-bones budget and hadn’t purchased a backup server. It was too expensive, and there was no such thing as the cloud at this point.

I’ll never forget walking through IKEA one weekend when my tech guy called me. He told me that our server had failed and couldn’t be fixed. My heart dropped; I thought it was the end of my company. That one server represented the entirety of the business — the very real possibility of losing the business, too, was terrifying.

Entrepreneurs know about obstacles. Startups fail 90 percent of the time, so determined entrepreneurs know that failure is something they’ll have to confront regularly.

Turning a concept into a reality isn’t easy, but true entrepre...

Having interviewed hundreds of people in positions ranging from developers to sales reps, there are some interesting patterns that emerge.

LEVEL +0

There are a number of things that candidates focus on which are in the “cannot hurt” category. To be competitive as a candidate these won’t suffice.

Dress for success?

So cliché. Your mom probably told you to “dress for success” but she also reminded you to be yourself. Come to an interview as yourself, if you’re comfortable in ‘business casual clothes’, wear those, if you’re only comfortable in jeans and t-shirt, great. If your confidence in a sales situation is strongest when dressed in a suit, bring it. Be yourself.

Follow-up letter?

“That candidate sent a great follow-up email so they have ...

For some Founders, their "job" at their startup isn't necessarily something they want to keep.

There can be a ton of factors at play, whether it's "I can't afford to do this any longer" or "I'm more passionate about something else."

No matter what the reason, it is, in fact, possible to quit our own startup. There are just some creative ways we need to approach it.

If I quit, who runs this thing?

Depending on the size of the company, there may be quite a few people who are interested in our jobs.

For example, if it's a 10 person company that's doing OK (not great), our CEO job might be something we're totally over but someone else in the company may find it as an incredible opportunity to be the CEO for once.

That same opportunity may co...

CHAPTER THREE: Start with the Outcome

In This Chapter:

-How to set goals to accomplish before scheduling a meeting
-How to communicate clearly when calendaring

How often do you start a meeting with a clear indication from everyone in the room with what you’re supposed to achieve after you leave? If you’re like most, not often.

Most calendar appointments look like this:

Awesome. You’ve let everyone know that 1. You are going to meet and 2. That there is an open ended discussion happening about the cataclysmic destruction of the planet.

However on the brink of Armageddon it’d be nice to know that the folks responsible for this discussion focused more on the ou...

Historically, the bulk of the Valley’s successful companies haven’t been the rocketship consumer successes like Google and Facebook. They’ve been the steady doubles, base-hits, triples, and home runs of the companies who sell software to businesses.

And in a time when Google and Facebook alone control some 80% of all digital ad budgets, that business model of selling something is starting to look better and better.

One of the few entrepreneurs to bridge these two worlds– selling intuitive, easy to use products to companies– and build a multi-billion public company out of it was Aaron Levie. Unlike a Marc Benioff, Levie didn’t come from the enterprise world. He never worked a day at Oracle or IBM. He came up with the idea in college.

It was ...

As a bootstrapper, I had a complicated relationship with the topic of acquisitions. I rejected the idea that an Exit Strategy was an important part of running a great business.

First, I believe that entrepreneurs are conditioned by our media, society, peers and their investors (if they have them), to think that selling their business is the ultimate manifestation of success.

Now that I have experienced the arc of scaling a profitable business and achieving a positive cash exit, I see the alternatives to selling more clearly.

On the one hand, I have appreciation for the commitment and vision it takes to turn down a lucrative, flattering, possibly life-changing offer in exchange for continuing to roll the dice and play the game.

On the other ...

"Do I bet the farm or hold it all back?"

We often wonder whether every dollar of our personal savings should be going toward our startup, or toward our safety.

On the one hand, if we don't bet our cash on our startup, we're starving the very thing we need to grow with. On the other hand, if we spend that money, we'll never be able to sleep at night knowing our safe landing has been pulled away.

So do I spend it or save it?

Don't spend it all. Seriously — don't.

There's a point at which depleting all of our savings and personal cushion works against us. We start shifting our focus from "growing the business" to "surviving personally" (more than it already is!) and at that point, we're in a downward spiral.

How much do I keep in savings?

I...