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Software startups, especially in their early stages, can be rough. As a founder, it’s easy to get lost in a world of opportunity. You could build anything — but you need to build just one thing. When you finally figure out what that one thing is, you know that you’re a million iterations away from that magical product/market fit moment.

“It’s interesting because I think there’s an obligation as an entrepreneur to always have to say that we’re killing it—but the reality is always, always, always very different. In the same day you’re taking over the world, then going bankrupt, then taking over the world, and then going bankrupt again. You’re going back and forth between and that low three or four times a day. It’s quite bizarre. Every positi...

Some entrepreneurs sail blissfully into the sunset after their first big payday. Others — like us — can’t imagine anything more boring. Instead, we thrive on constantly risking it all to build something out of nothing.

This condition of serial entrepreneurship is what I call “one and not done” syndrome. Maybe we’re crazy to be willing to start a business again and again. We know it will be hard, if not seemingly impossible, and there will be times when we will be overwhelmed with frustration. In spite of that, we know the journey is worth it.

If you’re this special breed of entrepreneur, I feel both sorry and happy for you. More than anything, I welcome you to the club.

There is a magic to what we do as entrepreneurs. We can create a thrivi...

People say that the co-Founder relationship is like a marriage — but what about when it actually is a marriage?

That’s the case for Michael and Angela Smith. They founded YipYap and created the first Bluetooth-enabled smart phone for kids, Pipsqueak, after realizing that handing over their very expensive phones every time their four kids wanted to talk to Grandma just wasn’t going to work.

“I love — and I’ve told her this — I love doing business with her,” Michael told me over the phone from the house in Texas that he shares with Angela and their kids.

But juggling a successful startup, homeschooling their kids, and still finding time for each other isn’t easy. Things can hectic and it’s a constant balancing act for these life and business ...

“Did you hear about XYZ.com? I just read about them yesterday. They raised a $5 million round from a top tier venture firm at a crazy valuation. It’s like they popped up overnight!”

Ah, the familiar refrain of “instant success.” The press loves you, investors love you, everyone wants to high five you and join your mission. You’re on your way to becoming the next Google, right?

Not exactly.

Well, unless in that same minuscule time period you’ve managed to build a profitable business with a sustainable customer base and cornered your market, you haven’t proven anything.

Success doesn’t come instantly, and it sure as heck doesn’t come from big announcements. It comes from a long term dedication toward building something real.

Launching Isn’t S...

In the startup world we’re used to hearing about billion dollar outcomes and massive exits. We’re all living the dream that our startup might be the one that turns into gangster retirement wealth. And, chances are, so are the people we’ve eagerly handed stock options to. We’re all hoping for that massive Powerballesque exit.

Yet, what if I were to suggest that a massive exit isn’t the only life changing outcome? What if I were to suggest that a $250,000 lump sum check might have more life changing impact than anything? Not because it’s more valuable than, say a $10 million check, but because it will likely have more near term impact and more importantly — you might actually get it.

Base Hits versus Home Runs

We’re all sort of used to a...

I recently had a difficult conversation with the founder of a startup looking for a small seed extension investment. I reviewed the company’s performance since their seed round and expressed concern with the unexpected increase in the monthly burn and the shorter-than-expected runway immediately after they closed on their seed round. I discovered that this individual and his co-founder had started taking combined annual salaries of almost $300k. This is a company with less than $400k in the bank and less than 6 months of runway. The company did not disclose the amounts of these salaries in the Use of Proceeds provided during the seed round fundraising process.

I tried to explain to this founder that he and his co-founder were going to blee...

Recruiting talent into a team is one of the most important things yet conducting interviews is often done in a haphazard way. It’s time for an intervention!

Let’s cut right to the chase: the interviewer’s first and foremost goal is to objectively assess the candidate’s ability to do the work.

If that sounds like what you and your colleagues already do as interviewers, remember this is an intervention — so let’s make absolutely sure.

The interviewer’s goal is not:

• to talk with the candidate about other work they’ve done
• to see how the candidate would ‘fit’ in the company
• to hear from the candidate about relevant experiences
• to gauge what the candidate says in alignment with the job description

And certainly not:

• to ascertain a candidate’...

How do you figure out what’s the right mix of skills for the co-founders of your startup?

Surprisingly if you’ve filled out the business model canvas you already know who you need.

I was having breakfast with Radhika, an ex-grad student of mine who wanted to share her Customer Discovery progress for her consumer hardware startup. She started by sketching her business model canvas on a napkin, but somehow the conversation quickly shifted to what was really on her mind. “After reading your post on Why Founders Should Know How to Code it looks like web/mobile startups have it easy. They seem to know the right mix of skills on their founding team is a hacker, hustler and designer. But what about for us, a consumer hardware hardware company? Tr...

The words “successful startup” seem pretty straightforward at first glance. But, what do you picture when you hear them? A unicorn? A world-famous company, like Twitter or Facebook? A small company bootstrapping and grinding through the night, with steady growth? A lifestyle business? A thriving brick-and-mortar shop? A string of failures, followed by the perfect product/market fit?

Like so many things in the startup world, the definition of what a successful startup truly is can be elusive — and frustratingly subjective. While some founders might strive for that billion dollar valuation, others measure their success by how happy their customers are or the biggest impact they’ve made on the world. When we dig past the visions of unicorns da...

Forget Snapchat. One of the most speculated about potential IPOs in Silicon Valley this year is file sharing and storage company Dropbox.

Dropbox was one of the earliest Valley unicorns to seem to defy any logic in valuations, and at its last round was valued at $10 billion making it one of a handful of so-called “deca-corns.” At one time, it and Airbnb made up some 95% of the value of Y-Combinator’s entire portfolio. And it was backed early on by top venture capital firms Sequoia Capital, on their way to raising some $600 million in capital. Its office was so lavish it reportedly spent up to $40 million a year just on employee perks. Its lobby sported a $100,000 statue of a Panda.

Yes, for a while, Dropbox and its co-founder and CEO Drew H...