A recent lunch revealed that while we should never stop seeking advice there comes a time when we are asked to give it. It also revealed that I had transitioned to the old-guy in these conversations.

A little over a year ago I was asked to lunch by a talented, young entrepreneur. The topic of the meeting was unknown to me but I’m always up for grabbing a bite and sharing thoughts with like-minded people. Maybe he wanted to knock-around some ideas, or ask if I’d get involved in his latest project. About 15 minutes into the conversation I had one of those moments where reality gives you a knuckle sandwich. He was asking me questions about life; questions about pursuing dreams, balance. It hit me. I was the old guy in this conversation.

While we should never stop seeking advice, there comes a time when we are asked to give it. It’s our job to push past the impostor syndrome and attempt to share what we’ve learned along the way.

With the acknowledgment of this transition (as well as my old-guy status), I set about to dispense whatever pearls of wisdom I could. What resulted (and follows ) was (is) a combination of tactical and philosophical advice that I find myself repeating in answering questions about entrepreneurism, balance and success (whenever I am lucky enough to get asked).


There you are, laying in bed about to fall asleep when your eyes suddenly flap open, you sit straight up, and in an instant, the world makes sense. You just had an idea. A good idea.

Quickly, your brain races in multiple directions running checks and balances in an attempt to validate your emerging brilliance. This initial due-diligence lasts only seconds and is less than thorough but good enough for your brain to return a passing score and head onto it’s next task. Like a soon-to-be parent, you start to envision the future with your new idea and it isn’t long before you are off to your computer, or notepad, to get started. This is it!

Now there are two distinct directions in which you can go from this point. You can either start building you product / business or you can start building your pitch to have someone else build it. The latter is where a lot of ideas die. I know because I’ve done it.

If you can build the first version of your product (or service) yourself you are already off to a great start. People don’t want to be sold your vision they want to buy it. In other words, they don’t want to hear how great something is — they want to see it and make the smart decision to be part of it. Why? Because people at a fundamental level want to be part of something bigger than they are. that has a life of it’s own; something destined for success. If all you have is a vision, it’s a lot more difficult to convince someone that this is that thing. Let’s look at an example.

Nathan Kontny created Draft by himself in the last year. He is an incredibly talented entrepreneur and his product is fantastic. Draft helps people become better writers by providing superior ways to collaborate and easy access to inexpensive copy editing. I’m not sure, but my bet is with the success of his app there are lots of people that would like to be part of his project. Nate is a one-man show and has created lots of momentum by himself. He is in a great position to negotiate ownership for hires and he saves himself valuable time in not having to ‘sell’ his vision in order to build an awesome team.

This is why you have to do as much as you can to get your idea from your head to market by yourself. Learn new skills; do what you think you can’t; get uncomfortable. The success of your idea will depend on your ability to transfer your motivation to others. The more you can make your idea a reality the easier that transition is.

I spoke about this specifically in my talk at The Big Design Conference last year.


In order for your idea to see it’s full potential you are most likely going to need to build a team, but not just any team. You need a team of rockstars who don’t have a problem making your idea their own, and using it to accomplish their individual dreams.

Your job is to inspire your team to do such a thing.

Inspiration creates conviction; conviction turns into action; action turns into wins; wins turn into progress and progress returns inspiration. This cycle is the most important ingredient for success.

But how do we inspire?

Conjuring up inspiration is an art, and the approach changes from person to person. There are however a few things that seem to be consistent in my experience.

  • Be a great storyteller. Great story tellers captivate people. They use words to paint pictures of things people long to be a part. They turn ordinary events into entertaining tales of bravery, courage, persistence, and success. Great story tellers get (and keep) peoples attention.
  • Assign ownership. Don’t give your team members parts of things to do. Let them be totally responsible for something. Help them get uncomfortable and show you believe in them.
  • Be a servant. Give your team an unfair advantage to ensure their success. Smart, driven people with the correct tools and support don’t fail. By definition this creates wins.

The heartbeat of a company is the individual wins of it’s team members.


The world of entrepreneurialism is riddled with stories of huge wins, big rounds, and Y-Combinator rockstars. Stories of 18 year old kids who sold their 18 month old project for 30 million dollars. These stories are inspiring and discouraging at the same time. Inspiring, because they give us a glimpse at what is possible, and discouraging because the equation to produce such things is so unrepeatable. What we need to realize is that there are many different levels of success, and entrepreneurs need to take time to define it personally.

Success as an entrepreneur can be as simple as doing what you love on your own time. Or perhaps success is developing something that truly made someone’s life better. Maybe it’s simply not having to sit in a cubicle.

For me, personally, success is earning enough money that my family can live a comfortable life, while maintaining the potential to create something meaningful and financially freeing. That’s it. Will I ever have an exit that will send a truck full of money to my house? Who knows? There are so many factors that go into that that which are beyond my control. I just want to have the opportunity for such things to happen.

To me , success is standing at my son’s soccer practice, and hearing my email ‘ding’ from my pocket with another signup for a product I just launched.

Back at my lunch, after realizing I was the mentor instead of the mentee, I felt humbled and thankful that that my experiences have lead me to a point where others would find it worth while to ask my opinion. I’m hopeful that my advice then, now and in the future, can help them start out on the right foot.



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