The most expensive time to raise capital is when we're most vulnerable.

This paradox is the heart and soul of where we get leveraged as Founders, particularly when we're giving up valuable equity. What we need to do in those vulnerable moments is step back and ask ourselves "Is this the best possible time to take on dilution or can we find a way forward that costs us less later?"

If we've never built a startup before, we may not even realize how important this question is. For those of us that have, we're hyper-aware of how badly we get beat up in our previous startup by not being more mindful of protecting ourselves when we were most vulnerable.

Our goal then should be identifying our moments of vulnerability and crafting a more viable pat...

No matter how much success we create with our startups, it almost never "cures" our need for validation. If anything, it often makes it worse.

It usually starts with this feeling that we need to prove the world wrong, and when we do, we'll have the last laugh (which is just code for "I need personal validation"). The relationship between building a startup and getting "revenge on something" is particularly strong with Founders because the very nature of what we do is so damn combative!

Haters and doubters are as much a part of our startup DNA as investors and customers. We've all had someone who thought we'd never pull this off, who questioned our ability and idea. Whether we admit it publicly or not, we all want to show them how incredibly...

Just because our paths as Founders have served us well, it doesn't necessarily create that same path as anyone else.

Yesterday, on a beautiful evening, I was sharing an ice cream with my daughter outside, and I asked her, "So what are you thinking about for your first job?" Mind you, she's 12, but I figured it's not that far off.

Without hesitation, she responded, "Well, I think I could learn a lot from working somewhere else, but I really just want to work for myself." I'll point out that she's started two "startups" so far, so this isn't a new concept to her. While the Founder in me was beaming with pride in that answer, another voice in my head asked, "Should she?"

As parents, should we encourage our kids to follow in our Founder footste...

When we sell our startup, it's not the simple financial transactions we all think it is. While we zero in the wealth event and the "freedom," we rarely take stock of the significant cost that comes with it.

Our startups aren't just about an income stream — it's not just a job. It's a part of us, something we created from scratch and worked tirelessly to bring into this world (I'm really trying to avoid a child-birthing analogy, out of respect to any woman who's delivered an actual child!).

When we think about selling, we need to think about all of the things that are going to be taken away, not just the dollars and freedoms that will be added. We often find that our startups provide a much deeper reward than what just having a job implies ...

While we may not know all there is to know about our business yet, there’s still going to be some good old-fashioned accounting to do. So let’s break out those green visors and add machines — it’s time to learn WTF accounting is!

At its core, in order to be an accountant we need to be able to collect all the sources of income and expenses and translate those into a spreadsheet. When the numbers are small, this is so easy to do we’ll wonder why people get paid to do it. When they get large, we’ll wonder why anyone is willing to do this for any amount of money ever!

Can any Founder do Accounting for Startups?

Yes! Because accounting for startups in the early days just isn't that complicated yet. Even if we've never seen any financial statements ...

The quickest way to halt productivity is through ineffective business communication. For people to do their jobs properly, they need to know exactly what is expected of them. In small business setting, a specific set of guidelines should be followed.

How will your team members know how to effectively interact if you don’t know how to do that? As a leader, it is your duty to understand how effective business communication affects your bottom line. To optimize success, here are three lessons small businesses should learn.

COMMUNICATION Lesson #1: Ensure transparency

When teammates are on different pages, the stage is set for disaster. If Johnny didn’t tell Charlie the “whys” and “hows” of the new retail displays, Charlie might end up deliveri...

A prospective client asked me to sign a Non-Disclosure Agreement (NDA) the other day before we began working together. After agreeing to sign his document, I was promptly shown a boilerplate template of an NDA that the guy had downloaded from the internet.

I had to laugh inside because I always tell my clients to secure an NDA whenever they are showing company information, a business plan and especially financials to anyone, yet I think NDAs are documents produced for honest people to be reminded to be honest.

I’m wondering if anyone else feels NDAs provide a sense of security?

According to Wikipedia, an “NDA creates a confidential relationship between the parties to protect any type of confidential and proprietary information or trade sec...

A market analysis is an assessment of any given market that includes both qualitative and quantitative research. Conducting a thorough market analysis as a key piece of your business plan ensures that you know everything there is to know about your market.

Coincidentally, it reassures any current or future investors that you know what you’re doing, that you’ve done you’re homework and that you’re the right entrepreneur to address the gap in this particular market.

HOW TO CONDUCT A MARKET ANALYSIS

But — in order to conduct a thorough market analysis — you need to cover a wide range of topics. Before diving into the specifics, remember that at its core, a market analysis is about learning the most you can about your market.

You’ll discover w...

Yes, there are Founders who take personal money off the table during funding rounds, and no, you probably won't be one of them.

For the unfamiliar, there is in fact a practice whereby investors are sometimes willing to directly purchase shares from existing stockholders (like the Founders) in order to create some liquidity for them personally. It's called a "Secondary Sale" and it simply means the proceeds go to the Founder, not to the company proper.

The problem is most Founders just hear "investors will give me money personally" and assume it's a regular practice. It's not, at all, but it's also not something that's very well explained to Founders either. So, here's how this actually works.

When to Ask

A few things have to happen for us t...

There's no perfect to know if you've found a great Co-Founder, but there are some really obvious ways to tell you're about to recruit a bad one!

Yet picking Co-Founders isn't something many of us will do more than once in our lifetime, so how could we possibly know what to look for? There's no absolute checklist, but there are 3 categories where most Founders don't press hard enough — Selection, Shared Cost, and Commitment.

Technically there's a fourth, which is "personality type," but that's so incredibly hard to determine in the early stages (see: all of dating and marriage) that it's almost not worth mentioning compared to the Big Three. If all of these start to sound way too familiar, it may be worth thinking about an exit strategy.

"Oh...