Dateline: Arlington, VA

Customer validation is worth its weight in gold.
High failure rates are well known for this field and of course none of us plan on being one of the grim statistics. But the number one reason for startup failures is a lack of market information and intelligence. Whether it is not knowing the true pain point(s) of the customer, the competitive landscape, industry trends, the classic “is this a nice-to-have or a need-to-have” or just the cultural and technological idiosyncrasies every market has, the right information can keep you on the road instead of heading full speed off a cliff. The rule you should keep in mind is there is no such thing as too much market information. No oil developer ever drills a well without thoroughly mapping out the ground beforehand.
 
So ask! Ask potential customers your questions, don’t be shy. People generally want to be helpful to startups and entrepreneurs. Engage in conversations with consultants in that industry (their value is their knowledge after all), executives who give presentations and people who write articles in industry publications. Challenge your assumptions, test out whether something would be valuable to a customer if it could do ‘X’.  I’ve lost count of the number of times I’ve heard an entrepreneur say “Wow, I wish I knew about that a whole lot earlier.” And given that early-stage venture dollars are harder to come by, customer validation lowers your overall risk and makes you a more palatable investment. If enough customers want what you plan to deliver, the money will follow.
 
Customers don’t like to change.
You’ll be hard pressed to find a company that says “We don’t like innovation.” Everyone loves innovation, it’s the apple pie held by grandma on home plate with an eagle on her shoulder. But the reality is that customers don’t like to change the way they do things. It’s very risky to stick your neck out for something new; transitions are expensive, take time and processes have to be changed. To take on a startup’s product or service means someone at your customer’s business may well have to put their job on the line to do it. That’s not going to happen unless at least one of two things are present - your value proposition is so strong that they can’t pass up the chance at saving or making more money from it or they are getting enormous pressure from their own customers to be better/faster/cheaper. That’s why one of the cardinal rules of a startup is to seek out and work on the most painful problems out there. Customers in pain are far more willing to take a chance on something new because what they currently have isn’t working for them anymore and the Band-Aids® and duct tape “solutions” are failing. This is why startup products that only have incremental improvements usually don’t work out - the value has to be big enough to balance out the risk of giving up “the way we’ve always done it” for an unknown solution from a company no one’s heard of (yet!).
 
Convince on the technology and convince on the financials.
Since most tech entrepreneurs have some kind of engineering or technical background, that is what they tend to focus on. And that’s good, having benefits and features that are superior to existing solutions is what you should be showcasing. But keep in mind that if you’re selling to another business, at some point a business-minded person who likely doesn’t have your technical background is going to be the one who makes the go/no-go decision with your offering. They’re not going to evaluate it on its speed, size, or performance, but on the impact to the financials - “How much money will this save me, how much more revenue will it generate?” Granted those specific numbers can be difficult to come by, especially if you don’t have a finished product you can run comparisons on, but you have to give them something meaningful that they can work with.
 
If the customer or investor didn’t “get it”, that’s your fault.
I’ve been guilty of this one too, walking out of a pitch shaking my head and muttering how my audience didn’t get my value proposition. But that’s our fault as entrepreneurs. We should be able to tailor our value explanation to any knowledge level. If we can’t, then we haven’t done our homework. Rework your pitch, simplify it, give it a new perspective, try a real-world analogy and focus on the elements that your audience will care most about and actually understand. Every audience is different, so find out their backgrounds ahead of time and also engage with them to get a feel for how much of your fire hose they can take. And have the good sense to know when your audience is getting glassy-eyed as you zoom overhead in your SR-71 and stop, drop back and reach out to them at their level.
 
There’s no such thing as a self-made person.
Our culture is full of rich and powerful myths regarding individual wealth and success, of the rugged wildcatter who took on the world and won, but this legend is one of the worst offenders and can really mess up someone’s expectations. No entrepreneur was ever successful by themselves. They always had help and other people were taking the risks right along with them. Your coworkers and partners are taking a risk, their families are too in letting them join up with you. The customers are taking a big chance on you (see the lesson above). Your bank will take a risk, and yes, your investors as well. Entrepreneurship is a team sport and egomaniacs need not apply. If you can’t work well and play well with others, constructively engage with people who can and will have very different personalities, work styles, and attitudes, then this role is probably not for you.