How to Think Like a Founder with Amy Smilovic
The safest way to lose your voice is to borrow someone else’s playbook.
Whether you are building a company, growing an author platform, or writing a book, there will always be people ready to tell you the exact formula for success. But if you follow someone else’s path step for step, you may arrive at a version of success that was never right for you in the first place.
In this episode of Kind of a Big Book Deal, Meghan Stevenson speaks with Amy Smilovic, founder and creative director of Tibi and author of Almost Reckless, alongside Meghan Stevenson Books collaborator Blair Thornburgh. Their conversation explores contentment, risk, first principles, writing an actionable book, and why authors must become their own measure of success.
How do you build a life—and a book—on your own terms?
Start by defining what “it all working out” means to you.
After exploring that question, Amy’s conclusion was that “having it all work out” is less about reaching a number and more about feeling content.
For Amy, contentment comes from three things:
Agency: Having power over her own life, problems, and wins
Shared mindset: Being around people who are hardworking, open-minded, and interested in real discourse
Creative best: Doing work she believes in deeply enough to defend, improve, and receive feedback on it
When you define contentment for yourself, you can stop measuring success according to an industry, your parents, social expectations, social media, or other people’s opinions.
That is when you can take big steps that might look “almost reckless” to someone else — but feel aligned and empowering to you.
Why do first principles matter?
Amy’s principles emerged during a difficult moment for Tibi.
In 2020, the company was doing more than $70 million in sales and was on track to grow significantly according to its five-year plan. But Amy and her husband were deeply unhappy.
They had to ask a different question: What would make the business worth continuing?
The answer was contentment. They created a measuring stick based on the three principles of creativity, agency, and shared mindset.
For Amy, these are first principles. They must all be present at the same time.
Creativity without agency is not enough. Agency without shared mindset is not enough. Each principle informs the others, and together they help determine whether a decision is aligned.
This kind of principled life can make decisions easier. When you know what must be true for you to feel grounded and content, you can sense more quickly when an opportunity, relationship, business choice, or goal is right — or wrong.
How do you create a book that is personal and useful?
A personal story is not automatically a how-to book.
Amy and Blair shaped Almost Reckless as a book that uses Amy’s life and business experiences as the narrative arc while still giving readers practical ways to apply the ideas for themselves. The book is not a founder memoir, and it is not a guide to making it in fashion. It also does not ask readers to simply do what Amy did.
Instead, Amy’s experiences create the examples, while clearly separated “Do This” sections help readers translate the lessons into their own lives.
The goal was to make the book actionable without reducing it to a shallow, overly simplified formula.
Amy believes readers want information that exists between the extremes:
Not a pithy, catchy concept with no depth
Not an overwhelming encyclopedia of information
Enough context to understand the idea
Enough direction to put the idea into action
For authors, this is an important lesson. Your story can make a book memorable and emotionally resonant. But practical exercises, concrete takeaways, and clear reader guidance help people turn your ideas into change.
How can authors build an original platform?
Amy’s advice to aspiring authors is direct: You are your own algorithm. You are your own AI.
The moment you hand your voice over to someone else — or allow someone else’s output to define your thinking — you risk changing the DNA of what makes your work distinct.
No one can give you an exact formula for creating something original.
If you want to do something unique while closely following another person’s playbook, you are no longer creating something unique. You are following their path, toward their result, with their values and their priorities.
Amy’s guidance is to look in the other direction when everyone else is looking one way. In a world where many people are creating the same type of content and relying on the same outputs, differentiation comes from preserving your individuality.
Your perspective, judgment, experiences, and voice are the raw material for your author platform and your book.
Questions answered in this episode
What does it mean to have everything work out?
Is money the best measure of success?
How do I define contentment for myself?
What are Amy Smilovic’s three principles for a content life?
What is the difference between agency, shared mindset, and creative fulfillment?
What are first principles?
How can first principles help me make decisions?
Why should I avoid following someone else’s exact business playbook?
How can I write a book that is both personal and practical?
What is the difference between a memoir and an actionable nonfiction book?
How do you turn personal stories into reader exercises?
What is a reckless résumé?
How can waitressing, early jobs, and informal experiences build valuable skills?
Why should I stay present in everyday life?
What does it mean to collect the dots of your life?
How can authors create an original platform?
What does “you are your own algorithm” mean?
How can I stand out in a world of sameness?
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.
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