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What if one day we woke up and all of the things we set out to do in life were done? Would we be happy or sad?

This actually happened to me in the past year, and it's been freaking me out! But it's also been a cause for a ton of reflection.

As Founders, we set a ton of goals for ourselves and our startups — obviously. We work tirelessly toward those goals with the anticipation that once we accomplish them, something magical will happen.

What we rarely consider is what happens on the other side of these goals once we've crossed the finish line.

In Case You Missed It

We Need a Strict Definition of Personal Success Every moment we spend pursuing an undefined goal is a complete waste of time — especially personal goals.

Why No One Tells Founde...

What if college simply doesn't make sense for aspiring Founders — are we ready to sacrifice this sacred cow?

Last week I was having lunch with a very successful old friend who made over $100 million in his career. He wanted me to sit down and advise his 18-year-old son who had just graduated high school. The first thing he said was, "He's decided to skip college and go straight to starting his own company."

This is the first time I've heard a parent say that out loud, but I'm starting to think it certainly won't be the last.

My immediate gut reaction was going to be some defense of college, even though I dropped out as fast as I could to start my first company. But no matter how many points I sped through in my mind, I couldn't come up with...

What if our startup is only failing because we refuse to let it evolve?

There’s a moment in every Founder’s journey when nothing feels like it’s working. The product isn’t catching on. The sales aren’t converting. The market isn’t responding. And the creeping voice starts to whisper: “Maybe this just isn’t going to work.”

But what if it’s not the startup that’s failing — it's us?

What if we're the ones who are holding on too tightly to the original product or vision that we're preventing our startup from evolving into what it's meant to be?

The Myth of the Perfect Plan

Most of us fall in love with an idea before we’ve ever tested it. That’s how this whole thing starts. We get a flash of inspiration, we build the deck, and we convince oursel...

A year ago, on a random Tuesday afternoon, I was driving home from an appointment and called an old friend — someone I’ve known for years, a high-level exec with big responsibilities and serious sales goals.

I asked him what he was up to. He said, “I’m floating in my pool.” I laughed. I thought he was joking. It was 2pm... on a Tuesday! People like him (people like us) don’t do that.

So I asked him why. He paused, like he’d never really been asked that question before, and simply said, “It makes me happy.” That was it. No explanation, no excuse. Just a basic truth. And in that moment, it hit me: the fact that I didn’t know that answer was my problem, not his.

In Case You Missed It

We Need a Strict Definition of Personal Success Every moment...

What happens when the company we built no longer needs the version of us who built it?

At some point, I walked into a building as the CEO of a company with over 600 employees. I looked around and realized our HR department had more headcount than our whole company used to be, which made sense because we were managing $10 million a month in payroll.

Our focus had moved toward doubling headcount — again. We were recruiting top execs from Fortune 500 companies to help us plan an IPO. These were the same people who would have never even looked at my resume a few years earlier!

I was 26 years old at the time, and it was becoming evident to everyone, especially me, that this company had clearly outgrown me. It was time for me to go — but what do ...

Wil’s Personal Note: “Founders, I want you to give yourself 100x more credit than you probably are for doing what you’ve already done. If we lose perspective of our progress, we’ve already lost. We need that perspective to fuel our next big win.”

When I was living in Beverly Hills, I felt like a total loser. This isn't some lame setup to a humble brag, I'm telling you I never saw this coming and it pissed me off.

As a kid growing up without much, I never thought in a million years I'd be living in Beverly Hills, so my expectations heading into life were very low. But every morning when I would wake up, I would look across this sun-drenched canyon and see the most amazing houses you would ever see — literally billionaire homes.

Do you know...

Guessing is Not a Successful Sales Strategy. Create an ideal customer profile instead.

Think your product is “for everyone”? That’s cute. It’s also a ticket to early stage startup hell.

One of the top reasons startups fail (42%!) is building something nobody actually needs. Translation: they never clearly defined who their real customer was. In startup post-mortems you’ll hear the haunting refrain: “no market need.”

An Ideal Customer Profile (ICP) is the antidote to that fate. It’s the crystal-clear picture of who truly needs what you’re selling. An ICP helps in qualifying leads effectively, ensuring your sales and marketing teams focus on the target audience.

Without it, you’re basically playing darts blindfolded and hoping for a bullseye...

We need to get back to building the startup that inspired us to begin with — we need to get back to our "Why."

Part of the Founder journey, really for all of us, starts with this amazing inspirational period of hopes and dreams, where we have this idea that we just can't wait to bring into the world. At that moment, all rationale and reason give way to exuberance and optimism — we become completely and utterly intoxicated with what's possible — and it's incredible!

At that very moment, we are filled to the brim with our "Why." Our "Why" is the entire purpose of building our startup. It's different for all of us, but it typically is a combination of personal goals, product vision, and desire to put a little dent in the universe. If you talk ...

Just because our paths as Founders have served us well, it doesn't necessarily create that same path as anyone else.

Yesterday, on a beautiful evening, I was sharing an ice cream with my daughter outside, and I asked her, "So what are you thinking about for your first job?" Mind you, she's 12, but I figured it's not that far off.

Without hesitation, she responded, "Well, I think I could learn a lot from working somewhere else, but I really just want to work for myself." I'll point out that she's started two "startups" so far, so this isn't a new concept to her. While the Founder in me was beaming with pride in that answer, another voice in my head asked, "Should she?"

As parents, should we encourage our kids to follow in our Founder footste...

Entry-level workers are no longer U.S. college grads—in fact, some aren't even human anymore.

The world of entry-level talent has completely changed in the past decade, particularly for startups. Not too long ago, startups raided colleges with an implicit understanding that among college grads, you could find someone who was smart (the college part), willing to work hard (lots of free time), and relatively cheap (first job).

I know this well because I was exactly that—young, relatively smart, insanely hungry, and freakishly cheap to hire. Since then, I've been trying to find my 19-year-old clone every single day of my Founder life. What has changed, though, is that the most fertile hunting grounds for those folks are no longer U.S. colleges...