Kelli Was Here

Kelli Was Here Episode 2: My Honest Story About Business Debt and Shame


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Welcome to Episode 2 of “Kelli Was Here”! In this raw and honest episode, your host Kelli dives into one of the most difficult and important topics in entrepreneurship, especially for women: business debt and our complicated relationship with money.

Kelli opens up about her lifelong journey with financial shame, inherited beliefs, and the realities of growing up with a trust fund but little understanding of how money actually works. She recounts her early experiences of never having to worry about finances, feeling disconnected from the realities of earning and managing money, and how those patterns followed her into adulthood and entrepreneurship.

From college days funded by a mysterious trust, to never really understanding work as a path to income, to her start in entrepreneurship where financial transparency was lacking, Kelli unpacks how a lack of financial clarity and open conversation set the stage for years of hidden debt, shame, and secretly living beyond her means. She shares stories of running her own spa, over-investing in business courses and certifications, and struggling with the guilt and secrecy around accruing business and personal debt—sometimes hiding it from her husband and family.

Kelli reflects on the cultural and personal narratives that tell women they aren’t good with money, the cycle of shame and secrecy that keeps us stuck, and the unique challenges of female entrepreneurship. Through her personal story, she highlights the importance of transparency, the pitfalls of a consumer vs. investor mindset, and how all the real growth and breakthroughs have come from finally facing her financial reality head-on.

This episode is a compassionate, vulnerable invitation to break the stigma and shame around business debt. Kelli encourages listeners to get curious about their own money stories, to break cycles of secrecy, and to approach investment with intention rather than from fear or desperation. She emphasizes that the debt itself isn’t what causes the biggest problems—it’s our relationship to it, the secrecy, and the shame that do the most damage, affecting everything from our marriages to our ability to be present as friends, parents, and business owners.

If you struggle with your business finances, hide your investments, or wonder if you’re the only one feeling weighed down by debt, this episode is for you. Leave a comment, share your experiences, or pass this along to someone who ne

Thanks for tuning into this episode of Kelli Was Here. If you made it this far, bless your brave little ears—and welcome to the beginning of something raw, real, and probably a little unhinged.

If this episode felt like a peek into your own brain, come hang with me on Instagram. That’s where I share behind-the-scenes chaos, brand rants, personal pivots, and questionable thoughts I probably should’ve kept in my Notes app.

More into slow-burn storytelling and “holy sh*t, did she just say that?” essays? Substack is where I write the stuff that doesn’t fit into a square or a reel—aka the uncut version of becoming.

💡 If you want someone in your corner while you do it…
That’s where I come in. I do personal brand coaching where personal branding is more like personal becoming—because this isn’t about building a shinier façade, it’s about showing up as the you that’s been dying to get out.

✨ Or skip the overthinking and stop by The Studio for done-for-you design, strategy, and copy that finally gets your genius out of your head and into the world.

📍 Start here → www.kelliwashere.com

If you’re navigating change, craving truth, or just tired of pretending you’ve got it all together, I’m your girl. Hit follow. Subscribe. Or slide into my DMs and say hi like it’s 2013.

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Kelli Was HereBy Kelli Preston