Dan Hogan, founder of Barrel Stock Trading Company, a fund that invests in Kentucky Bourbon, talks about learning from failure and success and why we shouldn't try to choose between achievement and enjoyment. Dan believes money is the lifeblood for any entrepreneur. Dan's first investor was his father, who bought a 1984 Cadillac Fleetwood with 410,000 miles to support Dan's limousine business. Dan also started with his college roommate an event business, a retail store, and other businesses before Dan went out on his own to purchase a home health agency. Dan's experience in home health led him to found Medalogix, a successful home health data analytics and operations improvement company. Dan worked for ten years in software sales for EMC where he learned the importance of how money moves in the world. Tom and Dan talk about how businesses are like bonds, and how building a business to grow is not the same thing as building a business to sell. Dan explains why he tells young entrepreneurs to raise more money than they think they'll need, and why trying to preserve your equity at the expense of the viability of the business is a mistake. Dan and Tom talk about why seeing things through the eyes of a beginner is essential to creating a new product and to parenting, and how developing a digital voice is more important than having a great personal network, and how bourbon is like bitcoin.