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Can we stop trying to replace our in-office culture with a remote work version?

I was a hardcore 80-hour-a-week office guy for over two decades. I prided myself on being the first one in and the last one out. The office was my badge of honor. It was where I measured my discipline, my loyalty, and my seriousness about work. But if you asked me to go back to an office today, even though this is my dream job, I would quit on the spot.

That does not mean I think remote work is universally better. It is not. It works beautifully for some people and terribly for others. What it does mean is that now that remote work has had time to marinate, we can look at it with more clarity. We can start to see what it is, and more importantly what it is not. ...

Wouldn't it be amazing if someone else could run our startup for us?

That's the dream, really.

We build our startups to a point where they are making money, hire some super competent person with our same kind of ambition, and just sit back and let the checks tumble in while we sip margaritas on a beach.

But there's a reason why we call it a "dream" and not a "given." It works really well in our minds, but it tends to fail miserably in reality.

Why Won't it Work?

The problem with handing over the reins isn't the immediate handoff, it's all of the little compounding problems that stack up over time. That's the part we don't see.

Imagine for a moment you were a parent with teenage kids and you wanted to go on a vacation without them. When you ...

How do you fire a Founder without having them leave the startup?

You give them a bullshit title.

The moment you hear about a new CEO being anointed at a startup, and you learn that the previous Founder/CEO is now the "Chief Vision Officer," or "Head of Strategy," or in some cases even "Chairman" — you pretty much know they got canned.

It usually means things have gone horribly wrong and from the outside you may not see it. But short of a company preparing for an IPO, the Founder rarely voluntarily relegates themselves to some arms-length title. It's almost always foisted upon them by someone else in the organization (typically investors) who are pushing hard for regime change.

So yeah, it sucks. But the way to make it less sucky is to unde...

Is it possible to recover from burnout?

Burnout doesn’t mean you’ve failed. It means you’ve slammed into the same wall every founder eventually hits.

The danger is mistaking your own exhaustion for your startup’s fate. Burnout feels permanent. It isn’t. Treat it like a setback, not a stop sign.

The real question isn’t if burnout will happen — it’s what you’ll do when it does. Some founders walk away too soon. Others find a second wind and do their best work on the other side.

We're So Connected — And Totally Lonely Despite endless digital tools, Founders are facing record levels of isolation, and only real human connection can fix it.

You Only Think You Work Hard There's a common misconception about 'working hard' within startups. Let's cha...

What if I told you that you had twice as many hours available today?

As Founders, we always complain about "not having enough time." There are a million things to get done, but only one of us to do it. If only we had more hours! What if we did?

I'm not talking about bending space and time here. I'm talking about re-configuring how we use our time in order to create the effect of having more hours. I've done it, and it was life changing, and I'm constantly shocked that more Founders aren't militant about how they use their time.

We all have enough hours to do everything we want, but how we use those hours is often our problem.

How I Found 8 More Hours Per Day

About 20 years ago I was working 16 hours a day, 7 days a week... for about 15 year...

Are we really aligned with everyone around us — our employees, Co-Founders, or even our spouses?

After 30+ years of working my ass off to find "synergy" with these three groups, I learned a painful lesson — try as I have, I'm not fully aligned with the people in my life.

I want to be. They are all awesome people. But I've come to realize that there are some important nuances that prevent Founders from ever being 100% on the same side of the table as the people around us.

This has been a source of endless frustration for me, and certainly for those around me. Over time, I've come to acknowledge and support the differences. But first, I had to figure out what the hell was so broken!

Should Startups be a Family? Running a startup isn't a grou...

What if the time comes when we trade our sacrifice for a payout and we find it wasn't what we had hoped?

Years ago I was sitting at dinner with my wife discussing the final details of closing on our new home in Bel Air, California. My wife, being the smarter of us, was lamenting the cost, and said that it was a big undertaking for our family, and she was second guessing whether we should do it.

I told her that was a big problem for me, but not because of the house. I said "I've been working every waking moment, non-stop for nearly 30 years. Every life event I skipped, every holiday I didn't celebrate, every experience I'll never get back was a promise I made to myself. That promise was that one day, it would enable me to do something extrao...

Congratulations — you just sold your company! Time to sit back and see the decimal places on your bank account sprint to the right!

Now you've got the means to do whatever you want with your newfound wealth. You've worked so hard to get here — what could possibly go wrong?

Everything. Everything can go wrong. And for many Founders it really does.

Whenever a Founder I know has a wealth event, the first thing I do is get in front of them and give them a very specific speech. I've been giving this speech for over 30 years, and I'd like to share it with you today.

I've lovingly titled the speech "Congrats, now don't fuck it up!"

You Only Need to Win Once

The problem with gamblers like us is that we love to win. So the idea of not winning again...

When does having "more" become a liability?

As Founders, we all start with nothing, so we're heavily conditioned to keep asking for more — more customers, more revenue, more capital, more resources. More is always better, because we have so little.

Yet if things go well, at some point we do have more stuff. We've got a successful company, a great income, and lots of toys. For the first time, we start to realize that getting "more" starts to become extremely expensive, and potentially not worth it all.

So, how do we figure out what that perfect balance is for us? How do we avoid falling into the trap of not being able to stop ourselves?

Who am I Really Competing Against? What if we're all competing in a game we can't actually win?

How to Fin...

Entrepreneurship saved my life. It took me from a poor, under-privileged kid to someone who finally felt like I had control of my future.

I strongly believe it has the power to alleviate the poor conditions of millions of people around the world, but how realistic is that transformation? Is access to meaningful entrepreneurship only accessible to those with means?

It's a question that's been gnawing at me for decades.

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How to be a Happy Entrepreneur Everything about entrepreneurship works against our basic human desires for comfort, stability and predictability. So, how do we keep ou...