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Penny Finance and Bentley alumna Criss Cole

Crissi Cole ’11 loves investing, numbers and the stock market. “My mom had me buy my first stock at age 14, and the rest is history.”  

It’s not surprising, then, that she majored in Corporate Finance and Accounting at Bentley and then joined Goldman Sachs in New York, where she worked first as an investment professional for high-net-worth families and then focused on building and modernizing tech for private wealth management. After a decade of success, though, Cole says she was still struggling to pay off college debt from her two degrees and her female friends and colleagues were in a similar predicament, asking her for advice on debt and investing. “None of us could get a financial advisor, even if we wanted to, because we didn’t have the $100,000 minimum that was required.” 

That didn’t sit well with Cole, particularly since it was an extension of what she experienced growing up: Her grandmother immigrated from Italy to America and built a successful seamstress business while her mother acquired an ice cream shop that she ran for 20 years, yet neither had accumulated enough retirement savings.  

“I’ve spent my entire life watching women work extra hard yet not have it pay off financially,” Cole says. “I saw an enormous opportunity to help the 70% of women who didn’t have access to a financial adviser but wanted so badly to build the best future for themselves and their families.” 

That mission became a reality in 2020, when Cole left her corporate job and founded Penny Finance, a digital-first financial well-being and education platform to help close the pay equity and wealth gap for women. She says, “We help women stretch their money further, maximize participation in 401Ks, IRAs, HSAs and other financial benefits and grow their wealth with a community of like-minded women.” 

And the fintech startup is making quite a statement. In 2023, Penny Finance was named one the best financial apps of 2023 by Real Simple Magazine alongside ones from JPMorgan, Ally, Sofi and other large financial institutions. Here, Cole provides a deeper look into her inspiration, goals and life as an entrepreneur. 

You had entrepreneurial role models in your mother and grandmother, but what was it like to take the leap and launch your own business? 

There was no playbook, no timeline, no funding, no structure. So, I started by testing my product design on female friends. I would create a financial plan with budgeting tools and steps to take for the essential money moves — for example, determining how much to put in a 401k. Then I would take real people through it and see where they got stuck, and how I could simplify the experience. I did this over and over again with a dozen financial topics and almost 100 women.  

Fortunately, I knew how to build tech from the ground up after owning a few tech implementations at Goldman; so I went to Upwork, posted a part-time project seeking a full-stack engineer and got to work building my hilarious hand-drawn, half-vetted mockups. Honestly, the rest is history. Today, we have more than 70 interactive, educational, simple-to-use online components that drive our custom financial plans, including calculators that continuously monitor future value and debt payoff.  

Have any Bentley skills or experiences helped you as an entrepreneur? 

Yes, particularly experiences with the Bentley Investment Group, the Student Government Association, business courses and summer internships. Learning the time value and business DCF [discounted cash flow] models in a corporate finance course, for example, was a huge help since the backbone of Penny Finance is time value of money. I also remember a study abroad trip to Ghana that turned into a 501(c)(3) social enterprise venture that helped fund education for children in Ghana. My college experience was centered around business. I grew up with an extremely entrepreneurial family, but Bentley helped me foster those skills, experiment and do so many cool things.  

To this day, I also credit career services with setting me up for success and I return to campus to share my career insights through programs at the Pulsifer Career Developemnt Center. In 2021, we hosted one of Penny Finance’s first in-person financial workshops at Bentley. I love coming back to campus to meet up-and-coming women and have even hired some Bentley grads! 

What are some barriers for women when it comes to pay equity and wealth-building? 

Women are retiring with half of the wealth of men. We are more educated, we comprise the majority of the workforce and we have excellent credit scores, yet we are saddled with debt and get into the investment game too late — if ever. Some women are rising in their careers at the same time they are raising children or taking care of aging parents. This creates an environment where it is hard to take risks and where there is likely less cash flow left over at the end of the month. You combine these factors, and 70% of women are not investing compared to only 24% of men. Hello, wealth gap.   

What are other factors that might influence the wealth gap between men and women?   

There is absolutely a cultural element here, where financial trade secrets and acumen are fostered in boys earlier in life and shared through male-oriented whisper networks later in life. Do women talk about investing at brunch? Typically not; but men do. This is of course a generalization, and I see the next generation wanting to change this — to know more earlier and make smart money moves earlier in life. But we have a ways to go.  

What is it like when you see clients make progress toward a financially stable future?  

I can’t explain the feeling. It is the best investment we could make, because financial freedom is forever — and will transfer to future generations. 


Committing to a wealth-building plan can be daunting. Crissi Cole says, “Forget budgeting, forget the 50/30/20 rule, forget about maxing your 401k; these are unrealistic goals for many people.” Instead, she shares these basic financial tips to get started on a path toward financial freedom: 

Know your numbers —

cash flow from paycheck, must-pay expenses, debt payments and 401k savings — inside and out (even if it’s scary). 

Whatever is left over is your “budget number.” 

Remember that your debt is not bad —

it gave you your life: your degree, your job, your house. Instead of thinking about the total amount of debt, which can be overwhelming, back into the minimum payment and pay a little bit more whenever possible. Build habits that you can scale up if your budget number increases in the future. 

Start saving and investing for retirement as soon as possible —

but remember that it doesn’t have to be $20k a year; start small and build up. The earlier you start, the less you have to save later — and the more you can take advantage of compound interest. 

RELATED: How sexism sustains the gender pay gap