Have you ever felt like you're digging a hole… and wondering if it’s actually going anywhere?
Friend, if you’re in that season right now—questioning your next move, your qualifications, or even your sanity—this episode is for YOU.
In this deeply personal solo episode, I walk you through the real, behind-the-scenes journey of building my business from nothing. I didn’t have connections. I didn’t have funding. I didn’t even own a camera when I decided to become a photographer in 2007. (True story.)
But what I did have? A gut feeling. A belief that if I was given an idea, then I also had the capacity to succeed. So I started digging.
And just like building a skyscraper requires a deep foundation before anything visible rises above ground, my business required years of unseen, unglamorous work before anything shiny showed up.
You’ll also hear my 1-on-1 conversation with Gary Vaynerchuk where he weighed in with his advice for next steps for building my holding company.
Here’s what you’ll hear in this episode:
- How I pivoted from photography to digital products, consulting, and software (with zero experience at each step).
- Why “wildly unqualified” might be your superpower.
- The key mindset shifts that helped me transition from freelancer to founder to CEO of a holding company.
- A message I’d share with every woman who doubts her ability to build something big.
I want you to know: if you’re still in the hole-digging phase of your business, you are not alone. And you are not behind.
This is the foundation phase—the part most people don’t see. But it’s also the part that determines how high you’ll go.
So let’s build something incredible, yeah?
Click >>PLAY<< to hear all of this and:
[00:01] Why I almost didn’t say the word “skyscraper” aloud (and why I changed my mind)
[00:53] The deeper the foundation, the taller the structure
[01:49] How I built a six-figure business without a camera
[03:39] The moment I realized consulting was a “thing” (and how it changed my path)
[04:29] From courses to a membership to a tech company
[05:20] Starting a holding company (without knowing what a HoldCo was) (A masterclass in figuring things out while you build.)
[06:18] For the women building against the odds
[09:15] My conversation with Gary Vaynerchuck
Listen to Related Episodes:
- Gary Vaynerchuk’s Growth Accelerator Program: My Experience and Key Takeaways (So Far)
- How to Get Attention and “Embrace the Dirt” for Long-Term Success with Gary Vaynerchuk
📧 Join my Newsletter for a weekly cocktail of insider business strategy, personal reflections, and the journey of being a thought leader. 📧
Click >>PLAY<< to listen now!

Gary Vaynerchuk
Gary Vaynerchuk is a serial entrepreneur and serves as the Chairman of VaynerX, the CEO of VaynerMedia, and the Creator & CEO of VeeFriends. Gary is considered one of the leading global minds on what's next in culture, business, and the internet.
Known as “GaryVee,” he is described as one of the most forward thinkers in business. He acutely recognizes trends and patterns early to help others understand how shifts in consumer attention impact the realities of the business world today. Gary's approach sits at the intersection of business and pop culture. He keenly understands how to bring brand relevance to the forefront. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber.