Send us Fan Mail

What if the biggest risk is letting other people define success for you?

In this episode, Meghan Stevenson sits down with Amy Smilovic, founder of Tibi and author of Almost Reckless, to talk about building a life and business that feels true to you. Amy shares how chasing outside markers like money, status, and industry approval can leave you deeply unhappy, even when things look successful on paper. Instead, she explains why contentment comes from three things: agency, shared mindset, and doing work that lets you be creatively at your best.

This conversation is a strong reminder that success is personal. Amy breaks down why your best decisions come from knowing your own principles, not blindly following someone else’s playbook. She also talks about the value of being present in every stage of life, because even small jobs and ordinary experiences can become the “dots” that shape your future. For listeners building a business, writing a book, or trying to carve their own path, this episode offers a thoughtful framework for defining success on your own terms and having the courage to pursue it.

This week’s guest is Amy Smilovic. Amy is an author, founder, and creative director. Born in the American Midwest, raised in the South, she moved to New York City and Hong Kong after college. In 1997, she founded the designer clothing brand Tibi, where she is the Creative Director. Tibi has grown to be America’s longest standing independently owned women’s designer brand, something Amy is intensely proud of.

Amy said, “I built this business with an incredible team that looks like a veritable UN Assembly. I have no doubt this fact has played a role in our success — not the optics of it, but that the composition of our team has always forced us to be very clear in our communications and work through the discourse that arises with varied points of view. And if I’m honest, the team’s shared mindset — exhibited every day in their work ethic and their willingness to take risks — is, in my opinion, the result of a through line that runs through our respective experiences.”

Find Amy at amysmilovic.com.

Find Amy on social
instagram.com/amysmilovic
instagram.com/tibi

Episode Highlights:
(0:00) Intro
(1:23) Meet Amy Smilovic and her new book
(2:35) Why she decided to write it
(4:00) Who Almost Reckless is for
(6:31) What contentment really means
(8:25) Defining success for yourself
(10:50) Why following others can mislead you
(13:03) The three principles behind real contentment
(18:25) Collecting the dots of your life
(24:21) Turning personal story into practical lessons
(29:20) Building your “reckless resume”
(41:32) Why thoughtful people connect with this message
(45:47) You are your own algorithm
(48:38) Outro

Have a great idea for a book but don't know where to start? MeghanStevenson.com/quiz


Traditional publishing expert Meghan Stevenson blasts open the gates of the “Big 5”—Penguin Random House, Simon & Schuster, HarperCollins, Hachette, and Macmillan—to share what every entrepreneur and expert needs to know about landing a book deal.

In episodes released every Monday, Meghan shares wisdom and stories from 20+ years in publishing as well as interviews with authors, literary agents, and editors. She also answers questions from listeners like you.

Whether you are an experienced entrepreneur with an empire, or are just starting out—this podcast will help you understand what you need to do in order to turn your dream of being a bestselling author into real life.