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As Founders, so many of us have joined this marathon because we believed there was our own version of "happiness" on the other side of it. The problem for many Founders, once they've "made it" is that they don't realize that money was never going to buy more happiness. In fact, it wasn't the problem they were solving for, to begin with.

Think of it like getting a big, honking bruise. In this case, that bruise is a metaphor for debt. When you have a bruise, you're constantly worried about it — it's super painful. So we think about how great it will be when it goes away. And eventually, it heals (we have some money). But all we did was get rid of the pain, we don't actually become "more healthy" than we were before.

The same goes for debt. Wh...

If most early-stage Founders were being completely transparent with their staff, their company updates would probably look something like this:

"Hey everyone, good to see you all on Zoom. So my quick update is this — We don't know if we have enough runway to make it to our next funding round. Also, I'm getting a lot of personal emails from folks saying they don't see the vision anymore. And personally, I don't really think this was the right decision for me or my family. So.. who wants to lead with OKR updates?"

That's the kind of truth that exists for us as Founders every day, and yet we find ourselves "hiding" that truth from our staff on a daily basis. Does that make us horrible people? Do all Founders leave this kind of information out?...

Imagine getting married to someone you hardly knew just because you "really needed to get this marriage thing going, and they seem qualified enough at the time." Does that sound like the recipe for a healthy long-term relationship? Probably not. But that's pretty much how most of us select our future spouse for our startups (aka "The Cofounder").

At some point, we inevitably step back and ask "Is this really the right person to be my long-term co-founder or did I just do a shotgun wedding with this weirdo?" Which invariably leads to "How can I tell if this is the 'right' co-Founder, and if it isn't — how do I unwind this thing?

To be fair, these are questions most Founders will end up asking, and if we're not, it doesn't mean our co-founder...

I've failed numerous times and watched countless other Founders do the same. We kept ourselves awake nonstop worrying about the outcome of our failures. We took years off of our life and put ourselves in horrible places mentally and physically.

And you know what we learned in the end? It generally didn't matter.

That's right, our "fear of failure" was always 100x worse than how the failure itself played out. And so we took desperate measures to avoid failure, like clearing the last of our savings, running up debt, and going yet another year without pay. At some point, we became far more intent on "not failing" than succeeding.

What we need is a method for dissecting failure into actionable bits.

Failure needs to be Unpacked

If we think ab...

We spend countless years getting our startups to an "exit." We all know that once we hit that promised land, everything will finally be OK. We'll satisfy our investors, our employee stockholders, and finally pay back all that debt we created. We'll get a vacation — a real one this time! We'll get back in the gym, we'll pick our hobbies back up, we may even find out what our kid's names are ("Chad, right?".. "No, Dad, I'm Jen.")

All of this will be an atomic mushroom cloud that lands us to what we've always been promised — validation.

We'll validate ourselves from the haters and naysayers. We'll walk into rooms full of important people who will all look at us and say "Can you believe what an amazing thing that woman did?" We'll get instant r...

For some reason, Founders are incredibly "shy" about giving themselves a raise.

It's odd really because we are responsible for looking out for the futures of so many other people, yet we often shortchange ourselves when it comes to our own needs. The reality is, our raises tend to come last, and in many cases, not at all.

So when is the appropriate time to pull ourselves aside and award that long-overdue raise?

Balancing Salary Versus Distribution

For many of us, the default answer on when our salary goes up (or down) is based on our ongoing Net Income. If we make more money, we take some home. If we lose a bunch, well, those credit card balances and Home Equity lines just keep growing... and growing...

That said, basing all of our "salary...

Most Founders get rich without ever exiting their business. Yes, you read that right. We don't have to build a rocket ship that takes on gobs of funding for an IPO in order to have everything we want.

We just need to keep making money (and not even that much!)

While to most people this may sound obvious, in the startup world we tend to forget how this simple fact works. We keep thinking in terms of this big liquidity event where we get handed a giant check like we just won the Powerball. We picture ringing the bell on NASDAQ wearing the only nice outfit we own shaking hands with bankers and smiling for the camera.

And in the end, we picture having enough money to just do whatever the eff we want.

The Stacking Effect

I spend a ridiculous amo...

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...

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...