Financial Struggles: One Founder's Debt Recovery Story

Financial struggles nearly ended KaiKini when a bad partnership quadrupled the founder's debt. Taryn Rodighiero shares what she learned and how she's fighting back.

In this series, I speak with people who know what desperate feels like. While now blooming into success, these founders share with me their deeply personal financial struggles and lessons learned on their way back to black.

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Taryn Rodighiero was serving in a restaurant when she decided she needed a change. She spent all of her savings on industrial sewing machines and taught herself to make swimsuits—something she’d never done before. For a year, Taryn continued serving while building her brand, KaiKini, slowly on the side. Then she quit her job.

Taryn and her husband lived off his income, and it was a tough time, she says. “We just scraped by.” But soon, KaiKini took off, and Taryn grew the company rapidly, hiring six employees and shipping her Hawaii-made swimwear worldwide. Then, Taryn had her first child. The stress of balancing home and work life prompted her to bring on a partner—a mistake that plunged the company into unimaginable debt. During the darkest days of the business, she says, she almost quit.

In Taryn’s words:

About four years into KaiKini, I had my first baby. I had postpartum depression, and it was hard during that time. I had to rely on my employees a lot more. They did so good, but then at the same time, we started to plateau. I was overwhelmed by learning how to be a new parent. I was at a low point—I was even thinking about giving up the business.

I found a business partner who had corporate experience, but then nothing in the grassroots, started-in-the-extra-bedroom kind of thing. I think I was just so ready to be like, “Here, you do it,” that I didn’t provide the amount of training that I probably should have.

My debt quadrupled. When I found out, my stomach dropped.

We ended up running the business into more debt in that one year she was with me than I had accumulated in the five years I had been in business. My debt quadrupled. When I found out, my stomach dropped. It really hit me what kind of trouble we were in. I was like, “Are we gonna have to leverage my house?” And, when we tried to get a second mortgage to remodel the kitchen, we were denied because of KaiKini.

I think my biggest mistake was not paying attention to my financials whatsoever. I take a lot of responsibility for what happened. For a while, I would have liked to put all the blame on her, but really, it was both of us. It was me not paying attention, mostly. I totally put blinders on and handed all that over to her. With whatever mental state I was in and the postpartum, I definitely didn’t want to deal with any of it.

We’re chipping away at the debt—I have over a third of it paid off already.

We had to make some major downsizing decisions. My business partner and I decided to part ways, then I went from about seven employees to me and two others. Between the three of us, we’ve kept it going for the last few years. We’re chipping away at the debt—I have over a third of it paid off already. It does weigh on me, for sure. It’s my burden. It’s like my penance.

Through this, I learned a lot. I realized that I did want to fight for the business. I wasn’t going to give up. In the end, it made me a better business person. Now I’m obsessed with my finances, and I will never ignore them ever again. Apparently I need to learn things the really, really hard way.

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Today, KaiKini is back on track with a leaner team, a focus on what they do best—made-to-order swimwear—and Taryn confidently managing her roles as both a mom and a boss.

Have a story about financial struggle you want to share ? Tell us more.

Illustration by Germán González

Financial Struggles FAQ

What causes financial struggles in a small business?

Financial struggles most often stem from inconsistent cash flow, insufficient starting capital, and running a business without a formal budget.

What are early warning signs a business is heading toward financial trouble?

Getting denied for loans or refinancing, debt growing faster than revenue, and relying on credit to cover routine operating costs are all early warning signs of financial trouble. Late customer payments are also a major red flag, since chronic late payments can leave a business unable to cover its own expenses and create significant financial strain. Owners who notice mounting debt or stalled sales should review financial statements right away instead of waiting for a bigger crisis to force the issue.

How can a business recover after falling deep into debt?

Recovering from significant business debt usually requires cutting costs immediately, restructuring existing debt, and negotiating new payment terms with creditors rather than taking on additional loans. Downsizing staff or scaling back operations can free up cash flow quickly, while consulting a business attorney or accountant helps map out a realistic repayment plan. Rebuilding takes time, but steady debt paydown paired with closer attention to financial statements typically prevents the same problem from repeating.

Should a struggling business bring on a partner or investor to fix its finances?

Bringing on a partner or investor can help a struggling business, but only when financial responsibility stays clearly divided and both sides maintain consistent oversight of the books. Equity investors, angel investors, and venture capital can supply needed cash, though any partner's experience with day-to-day financial management should be vetted before signing on. Handing over full control without proper training or regular check-ins can create more debt rather than solve the original problem.

How long does it typically take to pay off significant business debt?

Paying off major business debt typically takes several years rather than months, with progress depending on how much revenue can be redirected toward repayment while non-essential costs get trimmed. Restructuring debt, negotiating new terms with creditors, and consulting a business attorney can shorten the timeline. Businesses that track expenses and revenue in real time are better positioned to keep paying down debt without needing to take on new loans along the way.

How can personal life stress affect business financial decisions?

Personal challenges like new parenthood, illness, or family emergencies can pull an owner's attention away from day-to-day financial oversight, often at the exact moment close monitoring matters most. When spending and revenue aren't tracked closely, small issues can quietly accumulate into significant debt before anyone notices. Building a support system, whether through trusted employees or scheduled financial check-ins, helps keep the business steady when personal circumstances demand more attention.