Simon "Thor" Damborg is a former competitive CrossFit athlete, small business consultant, and the owner of Raincity Athletics and the Functional Fitness League in Vancouver, Canada. In this episode, which isn't your typical TFF conversation, Simon opens up about the challenges of building his businesses, dating in a culture of toxic masculinity, his "privileged guilt," the pain, isolation and shame of creating a "macho" personal brand, and how to make room for failure as an entrepreneur.

Amy Briant and Lisa DeLarco Bonoff are the founders of Lumion, a skincare product line revolutionizing skin health technology. In this episode, Amy shares the story of her painful split from a co-founder in her former venture, and what she learned the hard way. Tune into hear her advice on protecting yourself legally, setting boundaries, mitigating conflict, and optimizing co-founder relationships.

At 25 years old, Jessie Andrews is the founder and CEO of four successful businesses. Formerly an adult-film star and international DJ/Producer, she's now also a globally sought-after photographer, in-demand brand builder, and successful model and designer. In this episode, brought to you by Discover LMS, Jessie shares her unconventional journey from dropping out of high school to becoming one of the few adult actress to break through to mainstream. Listen in for her wisdom and grit-filled story, plus how to prevent the past from defining you, plus her advice in starting up and owning who you are.

Gabby Slome is the co-founder of Ollie; an all-natural, human grade dog food delivery service. In this episode, brought to you by Discover LMS, she shares how she overcame "analysis paralysis" and what she believes is most important in starting a successful business. Warning: Gabby shares some stomach-turning truths about the dog-food industry, so you might not want to eat while listening to this episode!

It's one thing to leave a job you hate to follow your dreams; but what about leaving that "cushy" job that's not totally terrible? In this interview, brought to you by Discover LMS, Sarah Merrill of "Big Kid problems" walks Megan through how she traversed this decision in her own life and how she's made a successful business out of social media.

From appearing as a guest on the day- time Emmy winning Steve Harvey Show on three separate episodes teaching "Social Media 101" segments, and being featured on various podcasts and websites as a "millennial thought leader", listen in as Sarah shares how she embraces fear and failure, and lets us in on her secrets to growing and monetizing her following to a quarter-million.

Known for taboo industry innovation, controversial subway ads, and a publicly challenging departure from her role as CEO of THINX Period Underwear, Miki Agrawal is a serial entrepreneur, author, and speaker. The four-time founder sat down with Megan for an exclusive first interview since what she describes as "trial by fire." Agrawal also shares how she believes anyone can be an entrepreneur, and how she navigates gender biases and double standards.

Cassandra Bodzak is the founder of the online mind-body-soul support community, Aprecity.com,and best-selling author of "Eat With Intention." She's a global meditation and wellness teacher, host of Eat with Intention TV, and former host of ABC's The Taste. Hear Cassandra's story on how she successfully built an online community and personal brand alongside the grief of heartbreak and her brother's life-changing diagnosis – then rebranded and did it all over again – as well as her advice for how to combat perfectionism and own your success.

Bobby Kim (also known as Bobby Hundreds) is the Co-Founder and Chief Creative Officer of The Hundreds – a massively popular streetwear line worn by celebrities such as Kanye West and Justin Bieber. Hear Bobby's story about the conversation that gave him the courage to leave law; how he's built a trustworthy brand; and the unique way he copes with success and failure.