Introduction:

This week, special guest Sharon Gillenwater lets us in on some dirty little secrets about Silicon Valley. She is the founder of two businesses. The first one was backed by venture capital and then destroyed by venture capital. Despite that experience, Sharon tried to raise capital for her second business, Boardroom Insiders, a software-as-a-service marketing tool that helps businesses sell to the top decision-makers at big corporations. But this time, the VCs weren’t interested. So she bootstrapped the business with the help of an angel investor—and proceeded to learn some surprising lessons, many of which she shares in her book, Scaling with Soul. Perhaps the biggest surprise came when she sold her business and learned the happy lesson that the founder of a relatively small bootstrapped business can walk away with more money than the founder of a venture-backed business that sells for far more. In our conversation, Sharon is unusually candid about what it took to build her business, what she learned about B2B marketing, and precisely how much money she made along the way.

— Loren Feldman

Introduction:

This week, Paul Downs, Jaci Russo, and Sarah Segal talk about how they wound up pitching their products and services not to consumers, but to other businesses. They all agree that selling to business is more profitable, and they all agree that it has other advantages, as well. “In general,” says Paul, “it’s easier to sell to businesses because the person you’re talking to, it’s rarely their money.” But some aspects of selling B2B can be harder. For example, how do you break through and reach the right person at a business, especially if you’re trying to reach the owner directly? And of course, there’s always a learning curve: Selling to a big business requires a level of professionalism that can be challenging, especially early on. Plus: Sarah explains why—even though she had to lay off people last year—she’s doubling her office space this year. Jaci is exploring what policies make hybrid offices most effective. And Paul, who says he’s having his best year ever, spells out the way he calculates when it’s time to add employees, as he had to do earlier this year.

— Loren Feldman

In this episode, Steve and Rich are entertained by two ladies from Springfield Little Theatre, Beth Domann and Lorianne Dunn, as they discuss tapping the creative energy you already have in the business for solutions to problems, how hiring the right people means you've already done 90% of the work, and by all means "Have Fun!"