Forums Search

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...

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

At Startups.com, one of our most popular products 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...

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, "...

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 ...

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...

For as much as we startup Founders love to innovate business models, we sure have done a lousy job of innovating on the employment model. Our salary lines tend to be our single largest expense in a company, and yet the biggest innovation we've had to date has been moving to a remote work system.

We've agreed that we don't need offices or "40-hour work weeks" anymore, so why haven't we agreed that we don't need the "full-time salaries" that came with them?

(Gasp!)

Yeah, I said it. Yeah, I'm about to be exponentially less popular. And, well, I wasn't that popular before, so… But seriously, why haven't we reconsidered compensation in an era where everything has become fractionalized?

Full-Time is Dead

Very few people actually work full-time an...

We need to treat every successful startup like it's our last — because statistically speaking, it probably will be.

In the startup biz, there are tons of second and third acts (I'm on my 9th) but there are very few that are ever equally successful. That's a problem for us as Founders, because we can easily lose sight of how important a single success is, and waste the opportunity thinking there will simply be another.

What if there isn't? What if this startup success, in whatever form it has right now, is the last successful startup we'll ever build? Shouldn't we treat it like gold versus assuming this is "one of many"? What happens if we get this wrong?

The Odds are Stacked Against Us

The first thing we need to understand is that the odds ...

The only thing harder than making a ton of money is giving it away to family.

On paper, it sounds easy. We've finally got some dough and now we can hand it out like Robinhood to all the people in need. What could feel better than helping our family with a little extra cash?

That's until we find out what a giant tangled mess of problems it tends to create. What we are thinking about is how helpful we can be, but what we're not thinking about — and where most Founders live in regret — is what a can of worms we open from here on out.

It. Never. Ends.

The problem with giving away money once is that once we open those floodgates, they are nearly impossible to close. All it takes is a single act of kindness to send those gates crashing open.

Here...

Venture-funded startups grow way beyond their means because they have to.

Time and time again we get asked by (typically bootstrapped) Founders about why in the hell venture-funded startups love that so-called "fake growth."

You've seen this before, when a new startup raises gobs of venture capital, hires hundreds of new people, burns through tens of millions of dollars (or more!), and then later on has to crash and burn the whole thing because it never actually made any money.

From the outside, it seems insane. What Founders don't realize is that this whole "fake growth strategy" isn't just some bizarre misstep - it's an actual playbook. We look at stories like WeWork and ask "How could anyone let that happen?" Well, it turns out, there's...

It turns out middle schoolers may be some of the best Founders I've ever met.

A little backstory. My kids go to a small school in Ohio that only has 208 students in the whole Middle School (grades 5-8). The school is very innovative, but one of the things that they do is allow the teachers to each pick one topic they would love to teach, no matter how weird, and pitch it to the entire Middle School.

I got invited to this pitch, totally unprepared as usual, and watched all of the other teachers pitch their classes. It was everything from "How to be a Pirate" to "How to Create your Dungeons and Dragons character." There were some seriously academic ones in there, but I was "sold" on the D&D course for sure! Where was this stuff when I was a kid...