How To Rise Through The Startup Ranks

It doesn’t matter if it’s our first startup experience or our eleventh, the skills we need to master to get from where we are to where we want to be, they don’t really change. So here are those things we need to master to rise up through the startup ranks.

The Myth of the 110% Entrepreneur

Startup burnout is a real thing. As the stigma traditionally associated with mental health issues melts away, we’re seeing a lot more entrepreneurs and startup employees raise their hands when the stress levels get too high.

How To Spin Out a Bigger and Better Startup

Startups are founded on the premise of disruption, and the tech we use to facilitate that disruption likely has multiple efficiencies coded into it that can be reapplied to other use cases. This is where the crazy money is made, because it can elevate our company from niche product player to new market dominator.

Hiring and Keeping Top Talent on a Startup Budget

To succeed in startup, you not only have to land the best talent, but you have to land and keep the best talent at the most value. Here’s how you do that, with four secrets no one else might tell you.

Should Your Startup Have Two CEOs?

Does it make sense to split the duties of a CEO in order to make a company stronger and more effective? Let me first make it perfectly clear that I understand the disaster scenario. Two leaders means a series of split decisions and bickering. Two leaders means mixed messages and incongruent priorities. Two leaders means everyone has two bosses. So first, let’s think about why any company would want two CEOs.

Building the Next Gig Economy Startup

Entrepreneurs and investors are placing bets that the gig economy is about to normalize and become an even greater share of the real economy. Here’s what I’ve learned about building the basics of a gig market platform MVP.

What To Do When Your Moneymaker Stops Making Money

Let’s talk about fallback strategies for when your biggest customer breaks up with you. I’ll prescribe a fix, but more importantly, I’ll lay out a strategy for prevention.

How To Get an Investor’s Attention

Let’s talk about how a startup founder gets funded. And why they don’t. I get about a dozen questions a week via my website from first-time entrepreneurs asking me to help them get their company funded. I don’t do that. But I do know a ton of VC and angel investors, so I asked a bunch of them questions about what works, what hurts, and what they look for from the very first contact with an entrepreneur.

How To Pay Startup Employees Fairly

I used to think salary didn’t matter, because I love what I do. But along the way I’ve learned that it’s critical to get employee pay right from the beginning.

Acquisitions Suck (here’s how to survive them)

Listen up. If your company is being acquired, or if you’re planning for an acquisition as your exit, you need to know what’s coming. Because a lot of it isn’t pretty.

When to ditch that nightmare customer (before they kill your startup)

Good entrepreneurs worry so much about where the next customer is going to come from that we never think twice about whether we should take on, or keep, a customer that's more trouble than they're worth.

* Featured in TechCrunch *

Why You Should Build Every New Product Feature Like an MVP

Making a mistake launching a new product feature is costly, and I’ve done it at least a dozen times. Never again. We’re all familiar with the Minimum Viable Product (MVP) strategy. What’s gaining traction now is the strategy of repeating the MVP process with every new feature, even down to every new version. How do we do that?

How To Raise Money For a Billion Dollar Startup

If we’re starting a company that we hope will one day reach a billion dollar valuation or more, we’ll need a different kind of strategy from the beginning.

How To Get Free Labor For Your Startup

Let’s talk about when we need to start paying the true believers working for our startup. With actual dollars. Because the alternative is usually promises. And promises in startup are always a bridge built to burn.

When Should a Startup CEO Step Down?

At what point does a founding CEO grow the company beyond their ability to grow it even more? It sounds like a Catch-22 of a question, but it’s a standard move that I believe startups get wrong more often than not.

How to Stop Undervaluing Yourself as an Entrepreneur

As entrepreneurs, it’s almost impossible to understand the value of what we’re building, and there are several reasons why we’ll sell our product for less than what it’s worth. Let's overcome that.

* A Medium Editorial Feature *

The Myth of Startup Sales Targets

Every entrepreneur comes up with simple sales targets soon after figuring out their most basic price point. We can’t help it, it’s what we do. But when it comes time for real sales projections, the math gets murkier. And we’re usually still just throwing random numbers at a wall and hoping they stick.

Why Startups Fall Apart at 50 Employees

Ask anyone who’s been there more than once, and they’ll tell you. Right at about 50 employees is where young companies start to go off the rails. So what should we do when it happens?

* A Medium Editorial Feature *

Five Minutes To Make Your Business Make More Money

Let's talk about how we use data to make a better product, raise our margins, and generate more revenue.

Should You Build a Minimum Viable Product?

Last week, I got a bunch of questions via my website from “Devin,” a smart young entrepreneur in the healthcare technology space. His MVP, a mobile app, was about six months from completion before he realized he needed to do more work around his business concept. Now his MVP is about a year out, and he’s frustrated because he wants to reach out to his target market to gauge interest in his solution.

The First Signs Your Startup Is Headed For a Sudden Shutdown

You know how startups can one day just suddenly implode, leaving a well-meaning but ultimately hollow note on their website thanking everyone for the incredible journey? It hurts every time I see that. Because you can prevent it. Not all the time. But you can see it coming. All the time.

Your Startup Needs a Product Engineer Immediately

The role of “product” within almost all industries is trending toward less emphasis on product management and product marketing, and more towards using technology and data to determine everything from what we’re building to how we’re selling it.

I Have To Fire This Guy, Right?

Firing an employee, especially at the startup level, is hands-down the toughest responsibility a founder or executive has to take on. I know this sounds like an elitist problem — oh, it must be real rough to have to ruin someone’s life. It is. Unless you’re an a-hole.

* A Medium Editorial Feature *

A Checklist To Explode Startup Sales Growth

When I see a working product not selling, it’s usually because the value premise was off from the beginning. What it almost always comes down to is: Does the product have a traceable direct value for the customer?

How To Deliver Software Without Deadlines

Let’s talk about how we deliver software when it’s ready, instead of when it’s due. This is how I’m transitioning from promising and missing dates to delivering continuous innovation, both across my org and to my customers.

You Need $250,000 To Start a Company

The harsh economics of startup are often easily overlooked. So let’s talk about what it really costs an entrepreneur to get a startup off the ground. It’s about 250 grand.

Quitting College For a Startup

Last week, I had an email exchange that came through my website from a college student who sort of lucked into a startup founded by one of his friends. He had jumped in at the beginning, and now he's at a crossroads.

Don’t Be Evil, But Don’t Be Saint Entrepreneur Either

I live by the entrepreneur’s motto: “It’s easier to ask forgiveness than to get permission. But it actually matters what you’re going to ask permission or beg forgiveness for.”

Why Entrepreneurs Stop Innovating

At some point, every entrepreneur stops innovating. Let’s talk about how to put that off for as long as possible.

Before You Launch Your Minimum Viable Product, Do This

Your MVP is your first impression, both for your startup and for you as an entrepreneur. Here's a high-level checklist I use to give my MVP its best chance, with some real-world examples thrown in.

Instead of Learn To Code, Learn To Hack Sh** Together

Should you learn to code? I used to always answer with an emphatic yes. Now I’m like 80/20 no. The catch is, and always will be: Time. Here's how to get around that.

The Myth of Minimum Viable Product

An MVP is indeed meant to be the quickest version of the product you can put out to market. But when I use the word “quickest” here, that reduction in time to market is achieved by a reduction in feature set, not a reduction in quality. Lately, I’m seeing the pendulum swing away from quality too often.

Three Stories Every Entrepreneur Should Know

What would you say your company does? It seems like a simple question that should have a simple answer, but that’s rarely the case.

The End of Software Development Deadlines

Building software under a deadline is a recipe for disaster, right? So why are we still doing it? It’s not gonna be too long before we look back and laugh at when we used to put delivery dates on tech.

Who the Hell Is Running My Startup?

Leadership flaws can start tearing at the seams of a startup right at the first signs of success. If we don’t have leadership that works, we can’t make critical decisions, we can’t move forward, chaos ensues, and the whole operation begins to crumble from the top down.

How To Have 10 Amazing Ideas Before Breakfast (and how to act on them)

When you’ve been an entrepreneur for as long as I have, you have a million ideas. Granted, a lot of these are trash. You can’t get to the great ideas until you sift through all the crap ones.

When Should I Hire a Developer for My Startup?

There a like a million things you need to do before you start spending money on that freelancer or offshore team. Wait. Five. There are actually five things you need to do before you hire a developer.