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ArticleHow Transparent Should I be With Staff?

How Transparent Should I be With Staff?

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?...



ArticleNever Tell People How Much Money You Have

Never Tell People How Much Money You Have

When I was just starting my startup career and had a little bit of success, I got the best advice ever from a friend of mine whose family had started a $50 billion company. He said:

"Never tell anyone how much money you have. Only two things will happen — they will either try to take it from you or size you up by it — either way, you lose."

I give that advice to every newly minted exited Founder I meet, and at this point, I've given that advice so many times I figured it was worth a detailed explanation. It actually doesn't matter how much you have (or don't have), the advice is just as valuable.

The Money Matters

Like it or not, we are judged by our money. If we have it, people judge us because they don't have it, and if we don't have it, ...



ArticleIs this the "Right" Co-Founder?

Is this the "Right" Co-Founder?

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...



ArticleWhy Isn't Anyone As Committed As The Founder?

Why Isn't Anyone As Committed As The Founder?

It's ridiculous to think that anyone will ever be as committed to a startup as the Founder.

And yet, we're constantly beating ourselves up trying to find just the right combination of great hires, strong incentives, and attractive growth to convert all of this raw talent into the committed, startup-building machine that we've become.

But it's 3 a.m. and we're sitting in bed staring at the ceiling completely engrossed in nothing but the future of this startup. Why isn't everyone else? Is there some sort of magic formula that would convince the rest of the staff to also be sitting in bed staring at the ceiling? (In this scenario we're assuming we'd want people to do that...)

It's time we realize, as Founders, that expecting the same level of ...



ArticleWhy Doesn't Anyone Understand What I'm Going Through?

Why Doesn't Anyone Understand What I'm Going Through?

As a Founder, no one really understands WTF we do other than another Founder. Our lives are basically attending a bunch of events where the conversation goes something like this:

Friend: "So, how is that startup thing you're doing?"

Founder: "It's going well (not true), but our burn rate is pretty significant and I don't know if we'll be able to raise another round of cash."

Friend: "Oh, OK. So what is it that you do again?"

Does this sound familiar? Look, I've been a startup Founder for nearly 30 years and to this day most of my family thinks "I do something with computers." This is pretty standard fare, but for first-time Founders, it often feels like this bizarre version of the Matrix that we're living in where we're the only people that...



ArticleHow to Make Potential Failure Less Scary

How to Make Potential Failure Less Scary

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...



ArticleWhy Selling a Startup Brings No Validation

Why Selling a Startup Brings No Validation

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...



ArticleWhen do Founders Get a Raise?

When do Founders Get a Raise?

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...



ArticleHow Founders Get Rich Without An Exit

How Founders Get Rich Without An Exit

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...



ArticleI Can't Have That — And That's OK

I Can't Have That — And That's OK

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...



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