Raising money isn't just about getting some cash in the bank, it's about committing to a very different path to building our startup.

And there's sorta no going back.

What no one told us going into the capital-raising game was that once we take money from investors, we're basically locked into a handful of outcomes, but more importantly, we're locked out of a few that we're probably going to want back!

We Significantly Limit our Potential Outcomes

When we're looking to raise capital, we're all thinking the same thing "We need more money to grow!" which of course makes sense. What we miss, however, is that taking on investors might increase the potential of our upside, but often comes at the cost of limiting other potential options that coul...

To grow or to profit, that is the question!

There we are, with a fistful of profit in our hands (finally!) and an endless list of places to spend it! Do we hire another engineer to get our product shipped faster? How about increasing our marketing budget to scale customer acquisition? Or, and let's just get crazy, do we finally pay ourselves?

Profit First, then Grow

I'm going to go out on a limb and spat in the face of startup lore, which suggests that the only way to succeed is to bet the farm and grow. Think of me as the owner of a casino (in this case, that casino is Startups.com) who gets to not only witness a handful of people bet it all and get rich, but 100x more bet it all and fail.

What we miss in our passion for greatness is that...

There's no golden age to start a company, but there is definitely a timer on when we can withstand failure. The question is — when does that timer expire for us?

As it happens, our numeric age isn't really what's driving our "Founder Expiration Date" — it's about how our age may reflect our relative appetite for risk. That's really a nice way of saying "What's the oldest I can be before I'm too old to recover from failure?"

Age Erodes Risk

Every year that goes by is another year we can't get back. When we're in our 20's and starting a company, we have our entire adult life to make up for the risk of failure. In many cases, we may not have a family or even a mortgage to worry about. At most, our failure may result in some lost years and a sh...

Every startup dies a few deaths before it lives forever.

But that's not what they tell us in the startup Founder brochure. Instead, we make up this fairy tale that our startup must be a great idea that instantly takes off, leaving customers and investors standing in line to hand us their cash. We keep making great decisions while we struggle to stay on top of our meteoric rise. Our days are jam-packed between photo shoots for magazine covers, headlining major conferences, and giving powerful speeches at company retreats.

Sound familiar?

No, of course it doesn't. Because that's not how any of this shit goes. The real version of a startup involves failing incessantly, sometimes to the brink of shutting down, until we rise back up and finally ...

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 ...

In the weeks leading up to the launch of Startups.com in 2012, I was coming off running 5 startups at the same time, 3 of them venture-funded (high stakes), on top of launching this one. I got married, had a child, lost my grandmother, moved across the country, and had nearly every major life event you could have happen — in less than 12 months.

On this specific day, I was at lunch with my co-workers and something about me just felt "off." I couldn't put my finger on it, but I was feeling dizzy for no reason and my body felt like it wasn't mine. After lunch, I hopped in my car and headed home to rest. While I was on the phone with my wife, driving on the highway, I said, "You know, I don't feel right..." and as soon as I said that — my wor...

How could we possibly be "right" as Founders when literally everything we are doing is unknown?

Think about it — we're building a startup that has never existed with a product that's being invented run by a team that's never worked together delivering to a customer who has never heard of us. Oh, and did I mention as Founders we've probably never done this before?

What about that formula drives certainty?

Separating Mistakes from Failure

Let me start by saying this — there is no possible way, NO possible way, that as a Founder we could possibly make the right decision over and over. In fact, the only way TO make the right decision is going to be to make tons of mistakes until we figure out which decision is correct.

We need to learn that whe...

Sometimes having to burn it all down is the best medicine our startup can take.

It sure doesn't feel that way at the time. When we're sitting across from an income statement that's been decimated and thinking of having to go back to our team, investors, and partners to tell them some truly horrible news, the last thing we're thinking is "Hey this might be great!"

But for those of you that have never been through it, I'm here to tell you, it may in fact be the best thing that ever happened to our startups.

That's because a Hard Reset gives us the one opportunity to go back and reset all of our decisions that we've made, teeing us up to build a far more efficient and capable startup going forward. It sucks — like I said — but it also has som...

Craig Newmark is the man behind craigslist —a website that today is among the 40 most visited websites in the world, is found in 70 countries, and can best be compared with Exchange and Mart in the United Kingdom.

Craig started craigslist back in 1995, and today he is reportedly worth more than DKK 3 billion. However, the last impression you get when talking to him is that of an entrepreneur guru. On the contrary, Craig is completely down to earth, something of a nerd (his word), and deeply passionate about using technology to make the world better.

He no longer heads craigslist but has dedicated his life to charitable work via Craig Newmark Philanthropies, which supports and connects nonprofit communities and drives powerful civic engageme...

As Founders, when we give away equity determines how much we're going to lose.

That's because the equity game, and our job of holding on to it for dear life, is really about vulnerability. The more vulnerable we are, the more we give away. The stronger our position is, the more we retain. It's really that simple, and yet, especially if this is our first startup, it's hard to realize when we're giving up too much too early.

There are really three moments in time where we have to really consider our timing and our approach — when we add co-founders, hiring early employees, and when we take on seed capital. What we often don't realize is that there is a lot of strategy to when and how we pull these triggers, while a lack of strategy has massiv...