What is one thing you should considering adjust about your pitch for different investors?

Every pitch you make should be tailored specifically to your audience and also tailored to the medium you are using. For example, the slide deck you email an to an investor to read through should be much different than the deck you use when giving a presentation in person. We had about 8 different decks at any given time while starting CoachUp, depending on if we’re giving a 3 min pitch vs. 10 min pitch, whether the pitch was in person or not, and how knowledgeable the investor was about our industry.

What is your top tip for staying connected to your customer?

Call them! It goes without saying, but the best way to stay connected with your customer is to speak with them as often as possible. I’m always surprised at how few entrepreneurs are willing to just pick up the phone and call their users. Customers don’t bite and you’ll be astonished at how much you learn about your product after speaking with an actual user for 5 minutes.

What is one thing you wish your employees would talk to you about, but usually don’t and why?

How to build your business! Most employees of early stage companies have brilliant insight into how you can improve you daily processes to operate more efficiently, or how to make your product better. I’m always shocked at what good ideas people have but fail to vocalize. There are a multitude of reasons why employees don’t speak up, ranging from never being asked all the way to fear of rejection. I’ve found for the most part it’s because they’re really just never asked. To solve this problem, I recommend setting up weekly or monthly 1 on 1 closed-door meetings with employees just to give them the forum to open up and speak their opinion about what the company can do better and how the product can be better (keep the meetings quick).

When considering building new technology to serve his or her business vs. using an existing SaaS product, what is the most important factor an entrepreneur should consider?

The easiest way to answer this question is to truly understand your business needs. The build vs. buy question is easily answered by determining if the technology is core to your business. You should always build technology that is core to your business. After all, it’s this technology that sets you apart from every other company out there…it’s what makes you unique. Never outsource core components of your business. If the technology is ancillary and it’s purpose is to make your business operate smother or more efficiently, then you should not waste time building these services and instead go with someone else’s SaaS solution. Remember the adage ‘Stick to what you’re good at’. Build your core competencies yourself and use others’ products to make up for areas in which you do not specialize.

Name one legal issue that most entrepreneurs don’t consider when starting a business, but should.

Using open source components! The number of startups that grab open source components to whip something together is growing by the second. However, startups need to consider the licenses that govern these components. I’ve taken the engineering department at CoachUp through two rounds of Venture Capital and each time the licensing issue has come up during our due diligence process. It is your responsibility to understand what your technology does under the hood. It’s great to just plug new tools and libraries into your codebase and be off and running, but remember that comes with a price. The worst thing possible is to get deep in the due diligence process with a VC firm and then have your deal fall through because you based your technology on a tool or library in a way that does not give you ownership of it.

What field or industry do you believe could benefit from more technological innovation? Explain why.

Education, without a doubt! Our entire education system in the U.S. is antiquated! Everything from the curriculum taught to the technology used hasn’t changed since my parents were kids! The world is evolving at an exponential rate, but our education system isn’t designed to keep up. We’re teaching outdated subjects to prepare our youth for our parents’ world, which doesn’t exist anymore. I’ve invested in QuickKey and Edtrips, two startups in the education space that aim to solve some of these problems directly and I hope that more investors realize the growing problems our nation is going to face if we don’t act soon.

Question: What is the best business or career book to give as a holiday gift and why?

The best business book I’ve ever read is the E-myth by Michael Gerber. The E Myth teaches entrepreneurs how to think about building their business so that they can turn their company into a well structured, systemized business. I truly believe too many entrepreneurs do not follow the advice in this book, which is why 80% of start ups fail.

Question: I know how people feel about them, but occasional meetings are needed for our team. What is 1 simple thing I can do to make sure they are useful?

Meetings can be productive if your team is vigilant and disciplined. To start, all meetings should have an agenda as well as an organizer. If you give someone the responsibility of setting the meeting topic, conducting the meeting, and then following up with action items, there is a good chance the meeting will actually be productive and drive your business forward.

Question: What is the #1 suggestion you’d give an employee who wants to pitch his or her boss on leading a new project?

There is a difference between average employees and great employees. Average employees identify problems/inefficiencies and bring them to their boss’ attention …great employees identify SOLUTIONS to problems/inefficiencies and present those solutions to their boss. If you want to lead a new project, you must be a great employee who has a reputation for developing solutions, not enumerating problems. That will give your boss the confidence to let you take the reins on a new project, knowing that you’ll end up eliminating any problems / inefficiencies that come up instead of creating new ones.

Question: I don’t check in with my employees often but would like to. What is one straight-to-the-point question to ask them when I do?

Regular check-ins are a great way to keep your finger on the pulse of your company. Frequent, shorter check-ins are better than infrequent, longer check-ins. I always strive for a 2-5min chat with every member of the team bi-weekly instead of a 30 min chat every quarter. When you meet that frequently, you’ll have no problem getting a sense of what is on their mind (sometimes, it will be nothing, and that’s ok). The best question to ask is always ‘From your perspective, if you could change one thing about the company for the better, what would it be and why?’ You’ll be surprised at the insight your employees have!