One of the coldest truths about startup is that it's pretty freaking lonely. I don't mean lonely in the sense that we spend long days in front of flickering laptop screens in dark, windowless basements. No, in that sense, startup is actually kind of social. When I say startup is lonely, I mean there aren't a lot of places to turn when we feel like we're going it alone.
Have you pivoted lately? If not, you should probably be thinking about it. Yes, a proactive pivot. Why? Because you’ve heard that old phrase: In startup, if you’re not growing, you’re dying. A lesser known but more actionable phrase is: If you’re not changing, you’re not growing.
If you're going to do startup, you're eventually going to fail. It will be shocking, painful, and costly. And until you've failed a few times, you won't be ready for it, because failure is one of the most misunderstood topics in startup. Let's fix that.
In startup, the difference between survival and running out of runway always comes down to taking our eyes off revenue. We don’t want to do this, and we certainly don’t do it on purpose. But when we’re in the middle of the startup run, it’s pretty easy to fall into a trap of wasting our time on feelgood tasks that seem like progress but don’t bring in any money.
One of the biggest mistakes entrepreneurs make is trying to be a competitor in an existing market instead of creating their own market. In this post, I’ll give you some case studies and strategies to get you thinking bigger.
One of the most common questions I get from company leaders is about who to hire and when. It doesn’t matter if your company is two people or 20 or 200, your next hire is always the most important hire. Filling the wrong role at the wrong time is a waste of money and potentially even a waste of talent.
Most of us entrepreneurs chase success like a dog chases a car - we don't know what to do with it when we catch it. That's because most of us have at least one weakness in our growth game.
I need to ask you a sensitive question. How many times have you gotten screwed out of fair payment for your product or service? If the answer is more than “zero,” then you’ve probably made sure it’ll never happen again. Right? Or have you? Chances are, there might still be gaping holes in your payment strategy.
If we’re going to spend time on competitive analysis — and mind you, lack of competitive awareness is one of the top reasons investors reject growth stage startups — we might as well go all in. Here’s how to do just that.
There’s a right way to approach crowdfunding, and a whole lot of wrong ways. Some of those wrong ways could lead to litigious customers, fines, and even criminal charges. So let’s talk about avoiding the most common mistakes entrepreneurs make when considering crowdfunding.
It’s easy for an entrepreneur, new or experienced, to fall into a loop where we freeze on decisions, second-guess ourselves, and get overwhelmed trying to map out the next steps of our company’s progress. At these points, we need help, experienced help, and we’re not sure where to turn.
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.
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.
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.
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.
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.
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.
* A Medium Editorial Feature *
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.
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.
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 *
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.
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.
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.
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 *
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 *
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.
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 *
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.
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.”
At some point, every entrepreneur stops innovating. Let’s talk about how to put that off for as long as possible.
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.
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.
There are 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.
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.
In a 20-year career as an entrepreneur, I’ve been lucky enough to have a few wins. But I’ve also had my share of startup failures, and I learned more with those than I did with the successes.
I’ll walk through each of my five startup acquisitions, and pick one thing I should have done differently, either before, during, and after.
The worst kind of startup isn’t the one that fails, it’s the one that stagnates. In startup and small business, if you’re not growing, you’re dying.
A couple years ago, in a perfect storm of circumstances, I wound up selling two companies nearly back-to-back. Here’s my story and, now that I have hindsight, what I learned.
One of the most difficult skills for an entrepreneur to master is solid decision making. But decision making is the “Executive” part of Chief Executive Officer, and you’ve got to have it.
One of the toughest questions I get about startup happens to also be one that I get the most often: How much of a pay cut should I expect to go to work for a startup?
As a career entrepreneur, I wear the customer-first badge. Proudly. I strongly believe raising money through customer sales is the best option, and in a lot of cases, it should be the only option.