ArticleTime is Our Greatest Asset

Time is Our Greatest Asset

The most powerful asset a startup can have is simply enough time to operate.

The problem is, most of us don't have that asset — at all. In fact, the very nature of a startup is often fighting the few moments we have left until our startup runs out of money altogether. Since we're all so hyper-aware of what happens when we run out of time, let's talk about the opposite — what happens when we have lots of time to build our startup?

Our internal motto at Startups has implicitly been "Let's stick around long enough to build our dream." That meant constantly fighting to stay profitable so that we could have an unlimited runway. As we celebrate our 11th birthday, I'd like to reflect on what the asset of "unlimited time" has done for us.

We Can Su...

ArticleThe Toll of Everyone Around a Founder

The Toll of Everyone Around a Founder

We all know how much of a toll being a Founder takes on us, but what about everyone around us?

It'd be nice to think that our journey, and the personal hell that is trying to be a Founder overall is limited to just our own world, the reality is our world radiates out to everyone around us. Our long hours, intense stress, and sometimes total failure doesn't just blow up our world, it has a strong ripple effect on everyone around us.

Startups Aren't Exactly "Marriage Enhancers"

If you ever want to truly test your marriage (or any relationship for that matter), try running it through the grueling gauntlet that is a startup company. While it's hard enough to build a strong relationship, mixing in a giant dose of anxiety and uncertainty does not...

ArticleBig Starts Breed False Victories

Big Starts Breed False Victories

Every startup launches victoriously — it's the rest of the journey that tends to put an end to it.

How many times do we have to see this same movie before we realize how it ends? Tell me if this sounds familiar: A startup launches with great fanfare — big funding, a "transformative" product, and heaps of early praise only to be nearly extinct in just a few years.

Whether it's the "next great media platform," Clubhouse ($4b valuation in 18 months, now almost defunct) or Bird ($2b valuation in just over a year, now worth $40m), we just keep seeing the same thing happen over and over.

What we're missing is the ability to discount those early announcements in favor of waiting for the actual results. We need to be able to see the early victories...

ArticleOnce a Founder, Always a Founder

Once a Founder, Always a Founder

We are Founders for life — we just happen to build a few startup companies along the way.

At, one of our most popular XXXXX is our "Founder Groups," where we pair 8-10 founders together to discuss the challenges of being a startup Founder. Invariably, startups succeed and fail, and the Founders find themselves asking us an existential question:

"Can I still be in a Founder Group now that I'm no longer a Founder?"

To which our answer is "Of course because you can never stop being a Founder." We say that because we don't believe being a Founder is a job that we happen to have while running a startup. Being a Founder is who we are as creators. Our startups are a single moment of creation, but our role and existence as Founders are...

ArticleThe Invention of the 20-Something-Year-Old Founder

The Invention of the 20-Something-Year-Old Founder

Yes, friends, there was a time in the days of startup yore when being a 20-something-year-old Founder was unheard of. It was the best of times, it was the worst of times, but mainly it was 1994, and rollerblading was still a thing.

I was a 19-year-old college student that had been living inside the Internet long before the Web browser came along (thank you, Marc Andreessen). I had this notion that these new "Web Pages," as we called them, would be a big deal, so I set up shop to build them for people.

Things were just starting to take off, and I went to my guidance counselor, full of excitement, to tell her I was dropping out of college. She was startled. "What's wrong? Is everything OK?" she inquired, to which I emphatically responded, "...

ArticleWhen is Founder Ego Too Much?

When is Founder Ego Too Much?

When is our ego an asset and when is it our greatest enemy?

The startup world is loaded with big egos, and if we're being honest, it kind of needs to be. We operate in one of the most insecure environments there is, where everyone is creating something out of nothing and hoping that next week they can simply make payroll. Without a little overconfidence, that's not an easy path to follow.

But that same overconfidence, when it's just pure ego, can also be our downfall. There's a point where we're no longer just confident, we're actually starting to lose our self-awareness altogether, and that's a dangerous spot. Many Founders don't even see it happening.

We Treat Assumptions like Facts

Early in our startups, we're forced to make a lot of big...

ArticleFounder Impostor Syndrome Never Goes Away

Founder Impostor Syndrome Never Goes Away

The way to get rid of Founder Impostor Syndrome is to just be a wildly successful Founder... right?

Actually no — and it surprisingly gets worse over time.

Founder Impostor Syndrome is what we feel when we think we're not truly qualified or capable of being a successful startup Founder. We second guess all of our decisions and outcomes because we have an endless stream of more successful Founders to compare ourselves to.

What we fail to realize is that no matter what we achieve, we never lose the feeling of being "less than qualified" we simply convert it to something else where we feel just as insecure.

Here's how it tends to happen.

We all Start as Freshman

Launching our startup is like showing up on the first day of High School as a do...

ArticleAlways Take Money off the Table

Always Take Money off the Table

Startups are an excellent way to make money — for everyone else.

We all love hearing the story about that super-successful Founder who made a billion dollars growing their startup. Those legends fuel the myth that we "rank and file" Founders must also be swimming in our Scrooge McDuck vaults of cash.

Yet, I speak to thousands of Founders and if there's one common thread when it comes to money — it's that most of them are beyond broke!

So how is it that we can spend so much time building a wealth engine that doesn't actually provide any wealth for us? Where is all that money going anyway?

"Back of the Line, Pal!"

The problem starts with us. When we launch our startup, we're wildly resource-constrained, so we start off by sacrificing our own ...

ArticleShould I Feel Guilty for Failing?

Should I Feel Guilty for Failing?

No one will ever create more guilt over startup failure than the Founder.

Startup Founders have an insane ability to manufacture epic amounts of guilt over their own failures. It's almost like we do some magical alchemy that takes every pound of failure or criticism and turns it into a metric ton of guilt.

But should we really feel this guilty over failing at our startups?

There are two answers here. The first is — everyone does it. But that is of very little help. The second answer is just "no." Failing at a startup is painful but should not be a source of guilt. Guilt comes from our misunderstanding of what actually just happened.

Startups Typically Fail

For those that are unaware, most startups fail. Most Founders are doing this for the...

ArticleThe Case Against Full Transparency

The Case Against Full Transparency

Startup Founders love the idea of full transparency when it works for them.

At first glance, it's hard to argue against the idea of "full transparency" in our startups. Who wouldn't want the inside information about what's really happening at a startup? Doesn't that make everyone feel more informed, safe, and supportive?

But try running a startup for long enough, and you'll quickly start to see that the concept of full transparency only works when things are good. The reality of running a startup quickly devolves into lots of shitty situations where going "full transparency" is more likely to sink our startups than improve them.

We Want Transparency When it's Positive

Startups often love the idea of full transparency in the early days when ...

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