Cal has a transformative moment in a conversation with a recent inductee in the Advertising Hall of Fame – Michael Kassan. The talk goes back to the days when Cal was educated in journalism school never to go to the other side of The Wall that separated editorial and sales. This education kept Cal from publicizing himself and associating with advertisers even as the Internet changed the landscape of communication. For years, Cal struggled with social media and self-promotion. But the conversation with Kassan, the founder of MediaLink, freed Cal to move into the future, and gives listeners an education on the changes we’ve all been living through at the intersection of content, advertising, marketing, entertainment and technology.

In our mean-spirited times, Cal steps into a conversation about kindness and receives a most thoughtful gift. Dete Meserve, the CEO of Wind Dancer Films and author of the books Good Sam and Random Acts of Kindness, shows Cal how the same skills and talents he used as a writer for decades can also serve him as a CEO. The epiphany comes at just the right time, as Cal sprinted toward his goal as CEO to raise a million dollars in new revenue for his business by the end of May. For Cal, the gift is life-changing.

Cal touches on the story of two brothers from Needham, Massachusetts, Bert and Johnny Jacobs, who converted their eternal optimism into a t-shirt business that is now a burgeoning company which provides assistance to a million children every year. It wasn’t easy at the start. The brothers spent five years driving around the country in a van trying to sell their t-shirts -- with little success. After five years they had a combined $78 between them. But then the smiling face of a character they called Jake next to the words Life Is Good sold 48 t-shirts in 45 minutes. And they knew they were onto something. The rest is history. Cal taps into his buddies – Bert and Johnny -- for inspiration as he closes in on the deadline for Million-Dollar May. Prepare to sing along.

Cal meets his polar opposite: The Boss in Heals. Heather Monahan. Whereas Cal was told as a writer in Journalism School never to sell, Heather came up on the sales side being told not to think of herself as a creative talent. She rose up the corporate ladder to become Chief Revenue Officer of the Beasley Media Group with 500 people working for her and was named one of the most influential women in radio only to see her job eliminated in a power struggle. But she used that tumultuous experience to turn herself into the author of the book Confidence Creator, and she is now a speaker and consultant on the topic. “Confidence,” she says, “is a skill to be developed.” She shows Cal how to be confident in areas where he doesn’t feel comfortable – and you’ll get a lot of tips, too

Cal looks at how John Rampton made millions by becoming one of the top online influencers in the world – tracing Rampton’s ascent back to an accident in college that left John bedridden in a hospital for months. John learned to master social media in that hospital bed, and he shows Cal how “giving away the farm” on the Internet is a gift that just keeps on giving through success and hard times. The founder and chief of online companies like Calendar and Due tells Cal he has numerical proof of the benefits of kindness. If you help people out on the Internet, John says, 1 in 10 will help you back. 1 in every 100 people that you help out will turn into a financial relationship. And 1 in every 1,000 people you help can turn into a million-dollar relationship.” Cal leaves the conversation hoping it will change his life – and yours, too.

Cal sits with Muhammad’s daughter, Hana, almost three years after his passing to talk about her dad. Hana has just written a book called At Home With Muhammad Ali, and this conversation looks at what life was like in the moments when the cameras weren’t around. There are happy moments – seeing her dad stuffing his mouth with bubble gum as if he were a big kid. There are beautiful moments – the way Muhammad took homeless people into his own home because he believed unoccupied rooms were a sin. There are painful moments – coming across the love letters her dad wrote to try to salvage the marriage that had broken apart between him and Hana’s mom. And there are moments of honesty that can come only from looking at illness and death. Through it all we see the unique capacity of this man to connect with the world.

When Cal turns into a salesman to try to generate a million dollars in new business by the end of May, he is unprepared for the constant buzzing of his cellphone and the new lifestyle this brings. When it begins to feel like his brain has fragmented into 500 pieces, Cal reaches out to his pal, The Monk Dandapani, for lessons on how to focus and concentrate. The world-renowned monk gives Cal advice on harnessing his energy, that can lift everybody’s life.

When Cal needs to develop a business strategy for his new company, James comes to the rescue. Altucher has started many businesses over the years, making millions, losing millions, making more millions, losing more millions and making more millions. A prolific blogger and podcaster, author, angel investor and owner of a comedy club in New York where he often appears, James shows Cal how to define, shape and monetize his new business helping companies tell their stories. The strategy session is a gift for anybody who’s thinking about starting a business – and fun for everybody else.

Cal gets the skinny on a new program that helps people lose weight. It’s not a diet (95 percent of diets do not work). There are no pills. The Reverse Approach was created by Mordechai Wiener while dropping from 330 pounds to 197. By listening to the stories of people who’ve lost a lot of weight and kept it off, you can adapt their successful habits into your own life. The concept is to slowly transform your body through understanding how you feel about yourself and then adjusting your habits. At the start, you don’t restrict the foods you love. You simply add foods that are healthy. And then you slowly learn to love the foods that make you feel better. It not only takes the weight off – changing your habits has been proven to keep the weight off.

The international best-selling author of 13 Things Mentally Strong People Don’t Do gives Cal some lessons on training your brain for happiness and success. And it couldn’t have come at a better time for Cal, who was recently challenged to lift his game as a CEO . . . and responded with an outlandish goal of bringing in a million dollars of new revenue by the end of May . . . without having the slightest idea how he was going to do it. Once she hears Cal’s background, Amy, a psychotherapist, actually thinks it’s a good thing for Cal to embrace this crazy idea and encourages him to get tough and go after it. Anybody who listens to this episode will be stronger for it – and have some laughs along the way.