Office Hours: I’m the CEO & founder of Penny Finance, but more importantly I spent 10 years paying off $100k+ in student loans. I’m Crissi Cole. AMA.Featured

Hi Elphas!

I’m Crissi Cole, the founder and CEO of Penny Finance based in Boston, MA. I previously spent a decade working in wealth management at Goldman Sachs in NYC, and now run a financial planning platform for women. I hold my Series 7 and 66 trading licenses and am a candidate for the Certified Financial Planner (CFP) designation.

During my career at Goldman, not only was I living paycheck to paycheck because of my student loans, but over and over again my female friends and colleagues would come to me (and beg me) for financial advice. There were no resources I could point them to and financial advisors wouldn’t take their call because they didn’t have $100k in the bank.

Now, I’m here for those women.

When I’m not working I’m mothering – soaking in my baby girl Charlie and…napping. Just kidding, toddler moms don’t sleep.

Ask me anything about your personal finances: getting out of debt, navigating the re-start of payments on student loans, investing, family finances, retirement accounts, estate planning, budgeting, saving.

Thanks so much for joining us @Citycrissi!Elphas – please ask @Citycrissi your questions before Friday, October 20th. @Citycrissi may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕
Thank you so much @Citycrissi for stopping by. So I have about $24k remaining to pay off my student loans an journey I’ve been on for 3-1/2 years. What advice would you give for staring motivated? Ways to pay more w/o trading more time for money? (I work 6- days a week now 😅)
@jamesadixon Ugh it is the worst. Knowing what the end game is going to be is how to stay focused and excited about paying them off. Take this quiz to see when you will pay them off without changing a thing. If that feels good – great, close your eyes and go. If you want to pay them off more quickly – here are a few ideas:
Hi, Citycrissi! My daughter is a senior this year and applying to colleges this month. To my mind, college is just as much about horizon-broadening experiences as it is about academics, and I've always encouraged her to go out of state to gain diverse new experiences. Now that the moment is nigh, though, I'm experiencing some sticker shock at $30k-$40k tuition prices. I had a full-ride scholarship, so I never had college loans. However, my guess is that once we tack on living expenses, we'll need to take out somewhere around $25k a year for her. She's planning to get a stats degree, which I'm hazarding a guess will earn her $75,000 within graduation. Since I didn't have to pay for my own education, I haven't the foggiest idea what would be a normal and reasonable amount of college debt to take on. Given your experience with student loans, is that much outlay okay or is it overburdening? Her dad and I will be able to help pay it down over time.
@nicolelarkin Congrats, mama. A daughter studying stats -- yes!. The cost of college is insane. The way I would think about a “reasonable” amount of debt is what kind of job and salary she can demand once she graduates. For example, if she can obtain an Actuary job out of college could yield $150k! And after years in the business, That return on investment is worth it for $100k total investment. Separately, make sure to submit the FAFSA on time, you may not get financial aid but you can get access to subsidized student loans from the government to help! Lastly, bringing your daughter into the conversation and process is key. Learning the trade offs of debt, the repayment process, the interst rate environment earlier on in your career will benefit her. The financial decisions will never stop once she is in the real world.
Hi Crissi, Wow, what an amazing journey! I wonder: What were the main differences between women handling their finances vs men? Have you ever pointed anyone to a financial therapist? Where do you think companies could improve the most when it comes to helping their female employees manage their finances? Thank you for the work you do!
@marissajoakim therapy is critical! money makes you feel things. We just launched resident money therapists at penny and believe deeply in mindset too. Women generally have more financial burden and more risk aversion. That makes financial planning different — we have to start with student loans — of the questions alone in this elpha chat half are about student loans! Companies can move the needle here — financial wellbeing starts at work. With the vast majority of employees reportedly feeling stressed about their finances and financial stress costing employers. an estimated nearly $200 billion annually. Employers must go beyond day care deductibles and start providing alternative solutions to help keep women and mothers in the workplace healthy and happy. Offer tuition assistance, long term care support, and overall financial planning tools beyond a 401k.
Hello Citycrissi! Thanks for making the time. Talking about time, how do you balance your role as a CEO with being a mother? What strategies have you found helpful in managing work-life balance?
@lynn36 Oh gosh this is the hardest of all the questions!! This is what I turn to @elpha for!! I haven’t mastered it, and feel like I am failing most days BUT on the few days I manage to figure it out I have done the following:1. Create clear boundaries between work and home. When I wake up with Charlie, I am with Charlie. Not on my phone. Not checking email. Not worrying about the meetings on the docket for the day. Same for bed time. I am focused on spending quality time with her, soaking up the snuggles while watching Sing 2 for the 300th time. 2. Make 30 minutes for myself – whether it is meditating, taking a walk, getting a manicure. I call these “commas” .... what is the mini pause (or a comma) in my day that allows me to get back to me – so I can bring my best self to home and work? 3. Built an army of babysitters and caretakers that I can call on to puzzle childcare together. Reliable, affordable childcare is the only way I can be the CEO of Penny. 4. During my work day – I try to work extra smart (instead of super hard). Mondays and Fridays are no meetings days. Those are brain days with no distractions that I can use to get sh!t done. Tues/Wed/Thurs are for meetings on meetings.
As a new mother, what have been the biggest lessons you've learned – personal or professional? Did anything surprise you?
@loree147 Motherhood is the ultimate endurance challenge. I thought Motherhood would come naturally and seamlessly integrate into my life, not the case. There is so much mom guilt combined with exhaustion and most times I feel like I can’t breathe. Showing up to work energetic, fresh, upbeat and present is really difficult. This has also made showing up as a wife, sister, daughter, and friend basically impossible. Lastly, I am shocked how expensive and labor intensive the childcare puzzle is. I hope it gets easier as Charlie gets older but I hear bigger kids … bigger problems :)
Hi Crissi! How do you think women can better prepare for financial security at a young age? What do you think is helpful to teach young girls specifically?
@lia85 overall -- education and confidence around money and finances!! The number one thing young women can do early on is fund and invest a retirement account. This is the largest contributor to the wealth gap. Women get a late start to the investing game (because of our student debt or risk aversion) and we miss out on compound interest. A 49 year old who starts investing for retirement at $500 a month will grow her wealth to $200k. A 22 year old who starts investing for retirement also at $500 a month will grow her wealth to $1.5 million.This is EXACTLY why we built Penny. <3
I understand the note on toddler moms don’t sleep. What is the single most important advice you would give to someone looking to get out of student loan debt?
@genevie16 Pay more than the minimum on your loans. Like yesterday. You can figure out that number with our free money quiz:, see if you qualify for forgiveness or reduced payment at
Hi, Citycrissi . Thanks for the AMA.I have two questions would like to learnwhat's the challenge of doing estate planing?and who is the most generation do estate planning?
@katezhang There are 3 main challenges with estate planning – 1. Understanding the tax frameworks for your state and federal 2. cost – sooo expensive to get a lawyer 3. Identifying the best guardians and executors for your family and estate If you don’t have kids and any assets over $50k, focus on getting a simple will together If you have kiddos and more money, focus on a more robust Will and creating a Family trust together What is zero cost to you is setting “beneficiaries” on your retirement and investment accounts – that can be done today without a Will or Trust!
What best practices or rules do you live by to budget your personal finances and not let spending get out of hand or sight?
@tajuana122 1. We use the “mini budget method” with Penny. separate credit cards for my big budget categories. One for must-pay items, one for each category you have been splurging on too much on. This helps you keep it in check when you see your total spend tally up every month. 3.Think about spending 3 times before you actually pull the trigger. One click buy culture is out of control – I fall victim to this sooo much – my Amazon bill creeps up on us and I’ll end up spending $100 extra dollars at Target because the holiday décor is too cute.