As a child growing up in Los Angeles, Jean Smart, founder of Penelope, watched her immigrant parents work tirelessly to provide for their family and employees. Owners of a grocery store and restaurant, Jean’s parents valued education and hard work. But, while they took care of everyone around them, they didn’t invest in their own retirement; this left them vulnerable in their later years.
With 1 in 4 Americans having no retirement savings, it’s an all too familiar story in the US: equal parts inspiration and cautionary tale, according to Smart.
Which is why, after a career at leading Wall Street financial institutions, she founded Penelope: a retirement savings platform exclusively for small business owners and their employees.
While we pride ourselves at Earn Money in Retirement for making cash flow accessible to anyone in retirement, we also believe Penelope is a great place to start if you already own a small business and have the time to prepare for retirement.
(If that’s not you? We recommend checking out some of our how-to blogs here, including wisdom from experienced names like Steve Lopez and Paul Dillon.)
Jean Smart’s mission behind Penelope.co
Before founding Penelope, Jean Smart worked in companies like Citi and Charles Schwab and in institutional employee benefits. These included 401(k) plans, employee stock options and financial wellness, making her an expert in this field.
She spent most of her life, as a Gen Xer, hearing that we’re running out of Social Security.
For many Americans Social Security provides an essential source of income in retirement, but with money running out, projections say that starting 2034, the SSA will reduce retirement benefits.
While this isn’t necessarily an issue for the current retirement generation, it’s a daunting future for many, including Smart. But she figured she was the right person to change this.

“I wanted to do something around fintech, education and inclusive capitalism … The reality is it takes generations to build wealth. It doesn’t happen overnight and it takes people working 20, 30, 40 years before they have money to pass on,” Smart said to Forbes.
What Smart wanted was a way to set it and forget it.
She recognised that businesses with less than 20 employees, the vast majority of small businesses, needed help. Most of these businesses are owned by minorities, women, and immigrants, and she wanted to make long-lasting security possible for these individuals.
So, she set about founding Penelope, an intuitive, cloud-based 401(k) program with NO 30-40 page documents and NO complicated jargon. The content provided is brief, to the point, and uses plain and clear language. She also offers different styles for the varying needs of her clients, in both text and FinTok videos.
She notes that, because the company is mission-based, it’s striking a chord with not just professionals in their early careers. She’s currently working with five generations, with individuals all the way up to their 80s.
How Penelope can streamline your retirement savings as a small business owner
Small businesses really are the backbone of America, with the Small Business Administration estimating around 29.6 million of them in the US (as noted by Slauson & Co in 2022). Which is why Penelope consistently works toward streamlining retirement savings for small businesses and their employees.
So a happy retirement really can be made a reality for all – no matter where the world takes us.
How to create an offer to bring in the most business

Penelope was designed to build bright financial futures for nearly 60 million American employees of small businesses and eliminate the hassle, jargon and hidden fees that make 401(k) plans prohibitive to most small and micro businesses.
Its aim is to give small businesses an affordable and easy-to-use way to provide retirement benefits and is helping small businesses navigate the challenges of the Great Resignation (as noted in Forbes).
It’s the retirement platform for small businesses, making saving for the future more manageable and affordable.
If you’re the owner of a small business and have some time to plan for retirement, Penelope.co can help you with:
- Recommending the plan that best fits small business needs, whether that’s a Pooled Employer Plan (PEP), traditional 401(k) or a Solo 401(k)
- Managing your employee roster and contributions from an intuitive dashboard
- They partner with Benefit Trust Company, a non-depository trust, who has selected State Street Bank to custody all your funds and securities.
- Accessing your information anywhere, safely, through a secure dashboard
- Penelope is designed to be intuitive and simple. Manage your plan and access support within a single dashboard.
- Transparent pricing, with a one-time set-up fee, no asset under management fee, a low monthly subscription fee and monthly employment fee
“Penelope means I can build a strong company culture at the start.” – Sherrell
“Providing 401(k) access to our team was a key component of our launch strategy” – Dave
Penelope.co is a great resource for you to get started securing a bright financial future for both you and your employees if you already own a small business and have the time to prepare. However, if you’re nearing retirement or already in retirement, there are still many options for you.
Explore our full list of articles, blogs and “how-to’s” to help you earn real money in retirement and gain inspiration on successful retirees so you can find peace of mind in your later years.