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Bringing on an Investor Means Hiring Your Boss


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The moment we take on an investor, we just hired our own boss. There's really no way around it.

It doesn't matter how much equity we give up or how we structure the deal. The moment we owe someone money, the dynamics change. People don't tell us that when we raise money, but if we've ever raised before, it becomes painfully obvious.

The Golden Rule: She with the Gold, Rules

Anyone who holds the purse strings to our startup essentially runs our startup. If I own 5% of your company but 100% of the capital, I run the company. I may not own the company, but if I control the blood flow of the company, it lives or dies by my choice.

The vast majority of capital raises place all of the flow of capital and the control provisions that come with that...



Article

Treat Departing Employees like Future Employees


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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...



Article

Let's Define Success By What We Don't Have To Do Anymore


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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.

The List of "No" is Life Changing

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,...



Article

How to tell Investors “Sorry it didn’t work out.”


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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.

We need to own the outcome

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...



Article

How a Founder should Communicate in Crisis


  

Founders are rarely prepared for how to handle a legit crisis, like when the whole world turns upside down overnight.

I lived through 9/11 with 700 employees, raised multiple funding rounds in the middle of the 2007 Financial Crisis, and just for "funsies" oversaw the overnight shutdown of a startup with 450 people.

So yeah, I have some experience here.

What I've learned is when crisis hits, a solid approach to communication is one of the single most effective tools we can employ.

Cut the Bullshit

In times of crisis, no one wants to hear the sugar-coated version of where things stand.

"Hey Team, I know half of you have turned into flesh-eating Zombies, but the good news is there's way more La Croix for those of you who have survived!"

No...



Article

Forget Compensation, let's talk "Quality of Life"


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Would you rather make $200K with a shitty quality of life or $100K with an awesome quality of life?

In the startup world we all seem to understand that $200K is better than $100K, but we do a really lousy job of qualifying that difference based on what actually matters — our quality of life.

When we step back for a second, we may come to find out that "compensation" in strictly monetary terms, is a broken metric. We're all really trying to translate those dollar signs into how it will impact our quality of life.

So why don't we just start with what improves our quality of life and then figure out where money comes in?

What we really want is time.

Years ago at Startups.com, we instituted a work from home policy. At the time we were all sti...



Article

Let's All Work On The Last Startup We'll Ever Do


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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."

But what if there was no "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...



Article

What If The Founder's Personality Is A Startup's Liability?


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During the early days of my first startup I stumbled upon a huge liability that was killing us quickly — me.

What's funny is no one else needed to have this discovery. The rest of the organization had figured out long ago that I was immature, combative, prone to anxious tirades, and generally a pain in the ass to work with.

And looking back, I'm probably being kind.

As a Founder (and CEO), every single one of those idiosyncrasies becomes amplified a hundred-fold because my liabilities to the organization become rooted in every decision we make, every interaction we have, and the entire morale of the company.

If we don't exercise some serious self realization — and do it quickly — we may be creating one of the biggest hurdles our organiza...



Article

Why We Plan Our Entire Business In 5-Day Sprints


  

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.

Less Time = Less Room for Excuses

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...



Article

Forget Inventing New Ideas, Try Improving What's Out There


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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.

Start With This: "What's Wrong With Current Products?"

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 ...



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