Interview With The Founder and CEO of Penny Finance, A Fintech Startup Tackling The Wealth Gap

  • Published on:
    February 7, 2022
  • Reading time by:
    5 minutes
Interview With Founder and CEO of Penny Finance A Fintech Startup Tackling The Wealth Gap womenontopp.com women on topp Crisi Cole

Meet the founder of Penny Finance, Crissi Cole, a veteran of Wall street and financial whiz. After college, she moved to New York City with a sh!t ton of student debt and was paying for rent on her credit card – even after growing up with a super-financially forward mom, studying finance in college, and landing that dream job at Goldman Sachs.

She figured it out without ever making a fortune or maxing out her 401k – with small intentional steps to trim down her loans and invest a little bit every year. Now she is on a mission to make financial advice more accessible to women who don’t yet have wealth. Because who wants to work till you’re 80? (No, thanks)

Tell us something about yourself: I am the founder and CEO of Penny Finance, an early stage fintech startup tackling the wealth gap. I am 32 years old, left-handed, live in Boston, am pregnant with my first child via IVF, and part-owner of my family ice cream business! 

What inspired you to start Penny Finance?

One of my former colleagues at work was crying in a conference room because she didn’t know how to file her taxes (even though she was the most badass, whip-smart young woman) and it was in that moment I knew I needed to build a platform to demystify finance and investing specifically for women. 

(We worked at Goldman Sachs, the mecca of finance, surrounded by arguably the best financial resources– and I still spent so much of my 10 years there teaching my women co-workers and friends how to invest their 401ks, how to pay down their student loans, and make the #s work) 

It’s hard for women to start invest when they’re in debt. What can they do?

Get your arms around your debt, and then start small. It is so normal to look at your total loan balance and think holy shit there is absolutely no way I am ready to invest. But, that is not the case at all. Even if you have $100k in student debt (A LOT), your monthly payment is likely around $500. Focus on the $500 a month not the $100k total – game changer. And then try to invest even 20 bucks a month. Or $100 once. You can do it. That $100 could grow to $2,000 over your lifetime. Start small, one step at a time. 

Can you share a few mistakes to avoid when investing?

  1. NOT investing your 401k or IRA. You HAVE TO invest your retirement accounts to build a nest egg big enough to retire. Contributing even the max every year doesn’t get you to the $1 million you need to retire. I see so many women doing the hard work of saving and contributing to their 401ks or IRAs, but not taking that extra step to invest the money. That is the magic piece.  
  2. Listening to the media and the hype around “getting rich fast”. Please don’t feel like you have to be a crypto-trader or a stock day-trader or start-up investor to make money. Investing in a long term, lower risk, stock and bond investment portfolio is how you protect and grow your money over time. You don’t have to follow the stock market every day or hit big on an investment to grow your wealth.   
  1. Understanding what you are actually investing in. This is why we built Penny. 70% of women opt out of investing – because they think it is too risky. Once you learn what the different investment options are, the worries go away. Education is the solve here.   

Can you share a few tips on how to become more financially secure?

Knowing your numbers and leaning into your financial picture is by far the #1 thing you can do. Women are incredible investors, financial planners and money makers. But we avoid it at all costs. Without the information, how could you take action? 

Practically speaking, first, know how much you have to spend every month to live (rent, insurance, car payment, etc), and back into if you have anything left over. With the left-over dollars, pay the minimum balance on your debts (excluding credit cards – if you have credit cards, please move them to 0% cards ASAP), open a 401k or IRA and contribute as much as you can to it, and set auto-pay and auto-transfer up on everything. And then spend the rest…. seriously… enjoy life and do the things you want to do. Just get your debt in order and save for retirement, first, and you are golden! 

What have been some of your failures, and what have you learned from them?


I pitched 70+ investors in venture capital last summer (a couple months after we launched our beta app). I didn’t get one yes. Not one. I was crushed. Looking back, that was a major blessing, and not a major failure. 

I had spent 2ish months of countless hours and energy on this first attempt at fundraising when I really should have been 100% focused on learning from our beta launch, tweaking the beta app, building our marketing tech stack, understanding the themes of where our customers were coming from. Instead, I thought we could super-charge the business before we had the metrics– nope! Slow down, sequence it out, and remember you can’t build a business overnight. 

And who knows – you might learn that you can fund your business without investors (like we did) if you focus on getting the product right, first! 

Tell me about what you’re working on now.

We are building more self-powered financial tools for women who are pre-wealth on penny-finance.com, and expanding our education modules to cover the full gambit of life events women encounter from 18 – 65. We are adding more community features so our women can connect with and learn from each other. And we are also building a mobile app for iOS and Android. Oh, and I am growing my first baby (the hardest of all these things!) 

How do you keep yourself updated? What are some of the websites or magazines or apps that you subscribe to or read regularly?  

I can’t live without Trello. It is my happy place. We manage a 13-person team and stay on-top of it all with the organizational boards, alerts and lists.  

I read CNN’s “5 things” every morning to stay up to date on the news, follow the financial markets via CNBC and MarketWatch, and read Inc. and Fast Company for entrepreneurship and leadership advice. 

I “time box” everything in my calendar. I pick no-meeting blocks where I can be heads down doing work, and stack all my meetings back-to-back on certain days so I am not switching from Zoom to work to Zoom to work. This has made me incredibly efficient, and less exhausted.  

What has been your key (or keys) to success? 

Consistency and focus. 90% of starting and launching a company is in the little details and tasks that build and build and build on each other. Every week I focus on the 3 things I have to get done, and my team has to get done, and do it over and over again. 

What is the best advice you have ever received? It’s not a race. Slow down. Enjoy each step in the journey. When you get to the “end” (whatever you think that end goal is in your mind) you will actually be really sad and want to go back and do it all over again. 

If you could go back by ten years, what would be some of the top tips you would give our audience?

Put that extra 50 bucks into your retirement account or towards your loans, your future self will thank you. And take that trip with your girlfriends – you only live once and you are only in your 20s with no responsibilities once. I let my anxiety of having sooo much student debt rule my life. It all works out. Oh, and power through that analyst job or bite your tongue with that terrible boss. You gotta start somewhere and will learn so much from the tough times ☺ 

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