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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...

A few years back I was driving through a windy street of Bel-Air with my wife, looking at houses. If you ever want to feel ridiculously poor, I encourage you to do the same.

During our home tour we drove up beside a house under construction that was so big, we thought it was a hotel. We just kept driving around the perimeter of the house, and it just kept going! Our realtor told us it was the future home of Elon Musk.

A younger version of me would have said "Someday I'm going to have that house!" and believed wholeheartedly that there were some future series of events that would lead to that outcome. It's the blessing and curse of being a Founder I think.

I turned to my wife and said "I can't have that — and that's OK." Let me explain why t...

There we are, once again, sitting at yet another Founder get-together while everyone tells us how great their startups are doing. Oh shit, that woman just said that they raised a massive round of funding. That guy just said he just surpassed 100 employees. The other person (I'm losing count) just claimed they are growing 50% per month.

"WTF? I thought I was doing great and now listening to everyone else I feel like a total loser."

And there it is. The age-old startup-sizing "competition" where we indeliberately one-up each other with how amazing our startups are doing. In the process, we all make each other feel miserable about ourselves.

What's that? You don't do that at get-togethers? Well, if you're like most, you're doing it anyway in s...

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...