Last week I had a great conversation with a Startups.com employee who was leaving to join another company. During the conversation I repeated the same thing I've told hundreds of departed employees, "This isn't the last time we'll work together, so while I'm sad to see you leave, I'm pumped to team up again later."
Why would we tell someone that's leaving how excited we are to be working together in the future? Because if we've been in this game long enough, we realize how many of those relationships do in fact come around again... and again... and again.
As Founders, especially veteran ones, we begin to learn that every single person we work with is part of a larger "workforce" of future hires that becomes some of our most reliable talent...
What if we defined success by what we DON'T have to do anymore?
What if we didn't have to work with people we don't like? What if we never had to miss dinner with our kids? What if we never had to think twice about taking a vacation?
Does this sound like startup Shangri-la? I thought so, too, until 8 years ago. I decided to build Startups.com based on everything I never wanted to do again.
It fundamentally changed my life.
It turns out that making a list of things we don't want to ever do is actually much easier than a list of things we are trying to accomplish.
That's because saying "no" is more immediate. We can say, "I'll take more vacations when I'm really rich" (the "someday" paradox), or we can say,...
Breaking up with investors at the end of a failed startup journey is basically every Founder's worst nightmare. It's that awful conversation we did everything in our power to avoid. We rehearsed it over and over while starting at the ceiling at 3 AM. And yet, here we are.
How we break up with investors is as important as how we built the relationship to begin with. That's because in the startup world, building long standing relationships among key players, including investors, is all about treating those folks with respect at every step of the journey — even the shitty ending part.
This is no time to point fingers. It was our job to create a successful startup; it didn't work out — we have to own that. This is th...
8 years ago I decided that whatever startup I was going to launch would be the last startup I ever did.
I made this decision after launching 8 startups and realizing that creating a company as a "means to an end" was a shitty way for me to live.
I found myself in this constant cycle of being wildly preoccupied by "the next thing." Raising money for my startup was a means to a quicker exit. Killing myself meant I could finish this chapter faster, more successfully.
I had endless justifications for compromising my life because I could always "make it up later."
This time around I decided to change it up.
I asked myself, "What if I picked what I wanted to do for the rest of my life NOW?" So instead of maki...
There's an incredible amount of magic in having very little time to get things done.
That's why at Startups.com, with over 200+ people, we manage our entire workload based on what we plan on getting done by Friday. That's it. No long term planning sessions, no confusing Gantt charts or Trello boards. Just 5 days to get stuff done.
And damn it's effective.
The problem with creating longer planning cycles is that every additional day, week, or month decreases the visibility and accountability for a single day of work. Our focus needs to be reducing the amount of time we can cheat on our time.
Imagine we wanted to lose 10 pounds this year. At lunch, we can order a cheeseburger, because hey, we have all year t...
While the novelty of creating the next Facebook sounds amazing, the truth is we don't need to necessarily invent a product to bring a new innovation to market.
If we look closely, we'll see that some of the fastest-growing companies out there — Uber, Casper, Dollar Shave Club and dare I say it, WeWork — are all based on ancient business models with a new twist.
Look, Uber didn't invent taxis — they just simply asked, "What's broken about the taxi business?" (Well, the limo business initially but who's tracking?) Any of us would be hard-pressed to find an existing product or service that couldn't use a ton of improvement.
What customers care most about is the improvement. Maybe that's ...
We're all freaked out about sharing our flaws.
We're worried that employees, investors, customers and just about anyone else will think less of us. Maybe they won't invest, maybe they won't buy our products, or maybe they won't come to work for us.
Sharing our flaws is terrifying. But it's also one of the most liberating things we can do not just as Founders, but as the weirdo humans we all are.
Geez, where do I begin?
I've been building startups for nearly 3 decades and I have tons of flaws. I've got massive ADHD (I can't even proofread this sentence without losing focus), terminal pain, crippling anxiety — and I can't dance to save my life.
For a long time I would have never even...
Imagine what would happen if we spent as much time trying to teach kids to become entrepreneurs as we did trying to get them to prepare for the SATs?
Let's remember that a disproportionate amount of our academic focus is around a series of standardized tests designed in an era where homogenizing the workforce was our number one goal (side note: it worked).
Now our goal is the polar opposite: differentiating our workforce. The only way our kids will succeed is if they can stand apart from others and chart their own course.
That's the essence of entrepreneurship, and it's something we can absolutely teach.
Kids are natural entrepreneurs.
They possess the most powerful skill any of us can have...
Getting equity back from an existing stakeholder isn't easy — but it is possible.
It's a situation that very few Founders have ever been through before, so no one really knows how to go about it. Let's talk a bit about how the situation develops and what we can do to get some of that precious equity back into our coffers.
More than anything, equity isn't just a stock issuance. It's a promise that at some future point that stock will be worth cash money — maybe.
When we think about pulling the equity back, we have to think in terms of how to redeem that promise of payment in some capacity. It's not just a matter of "taking it away" per se, it's a matter of trading the terms of the initial agreement ...
Funding doesn't make a lot of sense to first time Founders. In our minds, we think, "Hey, investors want to make money, so if my startup can make money, who cares how big it gets?"
Unfortunately, that thinking overlooks one big fact: that for every one investor check out there, there are hundreds of startups competing for it.
In order to understand how investors look at one deal versus another, we first have to understand how investors look at deals in the first place.
There's no absolute rule here, but investor behavior generally follows a consistent trend. Most "professional" investors (people who invest consistently) gravitate toward investments that can yield an exponential return, such as an IPO.