Crissi Cole Penny Finance
Crissi Cole, founder of Penny Finance. (Credit: Courtesy of Penny Finance)

Crissi Cole has watched women work hard her entire life. First her grandmother, who worked until the day she passed at 75, and then her single mom, who worked 70-hour weeks and brought her to the office on weekends. Cole tried to break this pattern by landing a job in finance at Goldman Sachs. But during her 10-year career there, she still found herself living paycheck to paycheck because of her student loans. At the same time, the Boston-based entrepreneur often had female friends and colleagues asking her for financial advice and referrals on small investments – but most financial advisors won’t take a call from anyone with less than $100,000 in the bank. In 2020, Cole decided to create the resource she and her network wished for: Penny Finance, a comprehensive financial planning platform made for women. Through Penny Finance, users can gain deeper insight into their current financial situations while learning how to invest (without laying out the big bucks), pay off debt, and save for their futures. 

Here’s our lightly edited Q&A, from The Story Exchange 1,000+ Stories Project.

How is your business different from others in your industry?

We serve people who don’t have money yet. We offer affordable financial advice. We offer holistic financial education. We are women-first.

The pandemic caused a big economic shock for both employers and employees, highlighting the fact that most Americans are vulnerable when it comes to financial security. Women are especially at a disadvantage – holding two thirds of the student loan debt and retiring with only one third the wealth of men. Penny Finance offers a digital-first financial well-being and education platform that will help close the pay equity and wealth gap for every female employee in the U.S. 

Tell us about your biggest success so far. 

About 21,000 women use Penny Finance as their virtual advisor. And, five Fortune 100 companies are piloting it with their women employees! Also, raising capital from 2 VCs in 2022 as a female founder, after trying (and failing) to fundraise in 2021.

What is your top challenge and how have you addressed it?

Creating a safe, inviting place to learn about finance for a group of people who are ashamed of, or shamed about, money. How do you get someone to do something they normally avoid at all costs?

Have you experienced any significant personal situations that have affected your business decisions?

Navigating IVF, then hyperemesis gravidarum and preeclampsia before giving birth and tending to a newborn baby while grappling with postpartum anxiety. This was really, really hard, especially because I got induced the day after we launched Penny Finance into the world. Startup life is a pressure cooker already – add in becoming a mom, and I almost gave up. But I powered through, sought help, and now my daughter is 1 year old and Penny is VC-backed with 10,000 users. We can do hard things.

What is your biggest tip for other startup entrepreneurs? 

Find a co-founder – this journey is lonely and exhausting!

How do you find inspiration on your darkest days?

I talk to my customers, which re-energizes me and reminds me that I am building something to solve a real problem. Sometimes you get no no no from investors or partners, and it makes you wonder if you are building a viable business. Then, I talk to a 55-year-old who has less than $1,000 in her retirement account. 

What is your go-to song to get motivated on tough days? 

“Light” by San Holo.

Who is your most important role model?

My mom. She got me into investing at a young age. And, she showed me how resourcefulness and work ethic can win over pedigree or wealth. ◼

Instagram: @startwithapenny
Facebook: @getmoneyempowered

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