Business is Equal Parts Art and Science: How to Trust Your Gut w/ Diana Wilson

Seed Money

The process of building a company, getting funded and bringing a product to market isn’t just data-driven. It’s gut-driven too. The numbers matter, but when you’re building a product without market acceptance, you have to trust your intuition and persevere when you’re told it won’t work.

In many ways, taking an entrepreneurial risk is a lot like taking a creative risk. You have a vision not many understand until you convince them. The journey can be lonely, and you’ll question yourself all the time. Considering that our guest took Ugg public and wrote a novel for the first time, she would know how similar the journeys are.

How do you keep going when you’re doing something so disruptive that no one sees the vision? What pitfalls do entrepreneurs fall into in that early funding stage? How do you learn to trust your gut?

In this episode, I’m joined by entrepreneur, leader and coach, Diana Wilson. She shares lessons from her own career journey, what it was like taking Deckers (Ugg) public and what every entrepreneur should be doing to succeed.

Guest Bio

Diana Wilson is a self-described industry agnostic, in addition to her most recent roles as CEO, Diana has held a variety of C-suite positions across a wide range of industries—from footwear to music—in roles covering all points along the strategic, financial and operational spectrum. Early career highlights include the high-intensity thrill of taking Deckers (Ugg, Hoka) public in 1993, spearheading a number of successful M & A transactions. Most recently she has completed a passion project of writing a fictional novel and launching a Substack Newsletter, Wit & Wisdom where she writes about everything from business and creativity—to health & wellness—to living a purpose-filled life. Connect with Diana on LinkedIn and subscribe to her newsletter Wit and Wisdom.

Host Bio

Jayla Siciliano, Shark Tank Entrepreneur, Real Estate Investor, MBA and experienced investor/founder in markets from consumer products to short-term rentals. If you like Alex Hormozi, Tim Ferriss, Entrepreneurs on Fire with John Lee Dumas, or you follow sharks like Barbara Corcoran, Lori Greiner or Mark Cuban (who invested in my Shark Tank pitch) you’ll love this show!