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When preparing for the new year, my partners and I look back on what has worked in our company, and what areas we would like to develop. This year we agreed we would put all commercially-oriented people in one big team — with me in charge.

Great, I thought, let me rethink how to make a commercial team in a way hasn’t been done before.

I Don’t Want to Become Evil Corp

At first, I wanted to organize my teams in a way that didn’t mirror the “Evil Corp”.

I’m not really sure why I was so afraid of this… I guess I’ve seen and heard a lot of stories lately where this has become the situation.

We even have people joining our team from other startups because their old jobs went too corporate, both organization-wise and product-wise. Somewhere along...

Everyone tells aspiring entrepreneurs — especially those in tech — that San Francisco is the only place they can be successful. After building a company in North Dakota and finding all the talent and funding I needed there, I’d like to offer an alternative perspective.

When it comes to small towns, it can be easy to think that the grass is greener somewhere else. There are small-town myths like you can’t find the right talent or you can’t raise funding away from the coasts. There is also a shortage of belief in success in small towns. But common startup concerns aren’t fixed by moving somewhere with more of everything.

In fact, with everyone crammed in the same place, startup necessities from money to quality hires to community support and ...

Stealth mode startups. They’re the cool kid’s club of the startup world. Who doesn’t want to know the secret, awesome, disruptive company that the latest 22-year old tech hot shot is working on?

Stealth mode is an excellent psychological trick that founders employ with the hope that the even cooler kids — i.e. the venture capitalists — will be intrigued and want to come join their club.

Problem is, it’s kind of BS.

Look, I’m not saying that no founder should ever have a stealth mode startup. There are legitimate reasons to choose to keep things quiet until you feel like your baby is ready for the world.

However, for most startups, the benefits of being out in the open — from finding the right product/market fit to locating your first 100 c...

“Stagnancy isn’t good for anything, from standing pools of water to athletic performance to startups serious about growth. Ensure positive outcomes and superior employee performance and avoid team rifts well in advance by staying attuned to changing individual and cultural needs within your workplace.”

–Michael Manning, How to Know When to Shuffle Your Employee Deck

“Every company needs to set its sights on fostering alignment between the best roles for team members as befits the business’s objectives and vision. It all starts with taking some steps toward a more organic way of managing people,” proclaims Michael Manning in her article on why shifting an employee role may allow you to see your team members in a new light.

Easier said than ...

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...