Guests - Risa Ryan, Meg Swain, Betsy Smith
Unretire Group Connects Retirees with Opportunities in Insurance Industry
The Silver Tsunami: Retirees Return to Workforce
Founder and CEO Risa Ryan is addressing a critical workforce gap with her new venture, The Unretire Group. During COVID, the workforce experienced what has been called "the great resignation" - a mass exodus of workers whose effects are still being felt today. Ryan noticed this problem firsthand while leading a team at a major insurance company.
"Towards the tail end of COVID, I was running a team at a big insurance company and we'd lost so many people to retirement," Ryan explains. "They figured they had enough to retire and really didn't want to commute back into New York. It takes an hour and a half to two hours each way from New Jersey to the city."
While workers enjoyed the flexibility of being home, Ryan recognized a deeper issue: "We were losing incredible talent—folks we need to help the younger generation develop knowledge, skills and especially the soft skills essential in insurance. In the insurance industry, things aren't always written down. It's often about walking down the hall and running things by experienced colleagues."
The retired workers themselves face challenges too. As Ryan points out, "You're going to be fine for a month or maybe two. But after that cruise, after that vacation, after you get a little suntan, you're going to be bored."
Today's retirees are dramatically different from those of previous generations. "When you retired at 60 in the 1960s, you were lucky to live 10 more years. And people were retiring from physically demanding jobs like manufacturing, construction, and transportation," Ryan notes. "But that's different today. 55 and 60-year-olds today have spent their lives in front of computers as knowledge workers. We take better care of ourselves—people don't smoke and drink like they used to, we have good diets, people exercise."
This leads to what Ryan calls a "30-year vacation" that isn't necessarily good for retirees. "Studies show rates of depression and feelings of isolation increase. I thought, 'I know how to fix this.'"
Creating a Marketplace for Retired Talent
Ryan's solution is a digital platform connecting retirees with companies seeking project work. "I hired four incredible software engineers—these kids have superpowers—and we developed this platform where retirees create profiles and view projects posted by companies."
The platform focuses on project work rather than full-time employment. "Retirees can pick up $5,000 here, $10,000 there, working however many hours a week they choose," Ryan explains. "It's great for companies because they don't pay benefits or 401ks, and they're not committing to a full-time hire, which companies are hesitant to do given current economic uncertainty. It's a win-win on both sides."
The platform launched to retirees in early 2025 and opened to companies about a month ago. "We've got over 300 retirees signed up in the last couple of months," Ryan reports. "For companies, we've had a couple post positions already. The platform has incredible talent—claims folks, finance professionals, underwriters, sales people—at all levels, from loss control specialists to CFOs and CEOs."
Companies pay $500 per month per post, while there's no cost to retirees. Ryan explains why she built the marketplace this way: "It's supply and demand. I figured I'd better have enough retirees on board before approaching companies to post projects, since companies pay the fee."
Mentorship: Bridging the Knowledge Gap
The platform addresses more than just staffing shortages—it provides crucial mentorship opportunities. "There are so many seasoned senior people that want to share their knowledge and wisdom," Ryan says. "This is the perfect avenue because they want to give back."
Winn highlights the coaching aspect: "Someone who was a CFO or CEO of a business and navigated different highs and lows in the market can make such a difference with someone who's now in that role. It's like having a coach for the player still on the field facing all the pressures."
This mentorship becomes particularly valuable for succession planning. Ryan shares an example: "I was at a meeting in Chicago last week with about 20 HR folks from smaller insurance companies in the Midwest. They were discussing succession planning—how to make sure the next person in line is ready to step in. The CEO can only do so much with a full-time job. But if you get a mentor who was a CEO, who understands the pressures, how quickly decisions must be made, how to analyze data and think about strategic direction—that resource can be invaluable to the next level down who you're grooming for leadership."
A Crisis in Insurance: The Talent Gap
The insurance industry faces a significant talent crisis. "There are 400,000 folks in the insurance industry eligible to retire in the next five years," Ryan reveals. "For every Gen Z that comes in, there are six boomers leaving. There is an enormous gap that's not going to get better anytime soon."
Part of the challenge is attracting new talent to insurance. "Insurance isn't glamorous," Ryan acknowledges. "There are a lot of sexier jobs these days. This generation, the Gen Zers, are very technically and digitally oriented, which isn't what you think of with insurance."
Yet Ryan passionately advocates for insurance careers: "It's a great industry. Once they get in, they realize no day is the same. You never look at a piece of property or business the same way again. You realize all the risks associated with it, and it's fun. But most people don't know or appreciate that."
Ryan elaborates on the diverse career opportunities in insurance:
"From a mathematical perspective, there are data science and actuarial jobs determining rates using historical data, identifying patterns, and predicting future claim costs. There's lots of math and programming—that's fun.
On the legal side, there are interesting issues like drafting policies, ensuring they cover what was intended and priced for. If you like analyzing words and making sure the written word matches your intention, those are great jobs.
In finance, there are loads of fun roles, whether helping set strategy on profitability or ensuring you know how much money you're making or not. Whether accounting jobs or MBA finance positions, insurance offers incredible opportunities.
The sales world is great because there are so many products—homeowners, personal auto, commercial auto, business owners policies, commercial properties, workers comp. From a sales standpoint, it's incredible, and you get exposed to absolutely everything.
You also have opportunities to work for global companies. I've worked almost solely for global companies, getting to learn about insurance markets in the UK, Switzerland, and Germany. You get to know industries around the world."
A Call for Retirees and Companies to Connect
For retirees in insurance, finance, banking, or marketing looking to engage with The Unretire Group, Ryan explains: "We are going to be the go-to platform for the insurance industry to find project-based talent. While there are platforms for full-time insurance jobs, nothing exists for project-based work. The insurance industry is looking to Unretire to find those retirees and project-based talent quickly."
Ryan emphasizes the importance of maintaining institutional knowledge: "The insurance industry isn't just stable—it's noble. The economy couldn't function the way it does without insurance. We have to make sure we're protecting it and ensuring that wisdom is passed down through generations."
Those interested in learning more can reach Risa Ryan at Risa@unretire.io or visit the website at unretire.io.
Smith and Winn: Addressing Police Issues and City Leadership
The 86-47 Controversy: Former FBI Director James Comey
Former FBI Director James Comey stirred controversy with a recent Instagram post showing "86-47" spelled out in seashells, which many interpreted as a reference to removing former President Trump (the 47th president). This post has drawn significant criticism, especially given Trump was already the target of an assassination attempt last year.
"It's ignorant, irresponsible, immature, and it just further destroys his legacy," comments Betsy Brantner Smith of the National Police Association. While she believes the post may be intended to incite those with hatred for Trump, Smith stops short of calling it illegal.
Winn adds: "If it's not illegal, it certainly appears to be unethical. What happens if seashells now sweep up and say '86-46,' the guy in between Donald Trump and Donald Trump, because now he has cancer? That would be so inappropriate, and people would be so upset about it."
Both noted the poor timing of Comey's post during National Police Week, with Smith pointing out: "He didn't post a single thing about that. He'd rather take a dig at Donald Trump than acknowledge police officers during Police Week, and that says everything we need to know about him."
Severe Weather and Emergency Response
Smith, currently traveling through the Midwest, reports on the severe weather affecting the region: "We just drove through quite a little rainstorm here in Iowa. We were on the Iowa-Missouri border and fortunately were able to avoid the tornadoes and storms in St. Louis."
The storms have caused significant damage, with Smith reporting: "The search and rescue area that they have been dealing with in St. Louis has been extraordinary. St. Louis is a difficult area to begin with, and now they've had a lot of damages with nearly 30 deaths. And then they've had a bunch of looting."
Despite these challenges, Smith notes positive community response: "The public is stepping in, working hard to protect their own properties. People are encouraging everyone to help each other and not hurt. We're seeing a quick response from FEMA."
Policing Challenges and Local Leadership
The conversation turned to policing issues in Tucson, with discussion of a recent post from the Tucson Police Protective League claiming Mayor Regina Romero used police resources for personal transportation to Phoenix International Airport for a trip to Qatar.
"Mayor Romero has four police officers assigned to her in the city of Tucson," Smith explains. "So city of Tucson residents, if you call 911 to report any crime except the worst, like a murder in progress, you're probably not going to get one police officer, much less four."
This led to broader criticism of city leadership. "We've had enough of potholes, fentanyl poisonings, homelessness related to the fentanyl poisonings, the trafficking, and the mismanagement of money for pet political projects that leave us without the police force that we need," Winn states.
Smith relates Tucson's situation to problems in Chicago: "Chicago is a cautionary tale for Tucson. The crime that is in Chicago is spreading to suburbs like Fairview Heights, where three police officers were shot over the weekend responding to a suspicious person call."
Both advocates for changes in local leadership. "The only way you can change that is if you change the leadership," Winn argues. "We fire CEOs in this country when they fail, when they don't do the job. It's time to reconstitute the leadership in this city."
Smith adds: "Remember what Donald Trump said to Chicago four years ago: 'What do you have to lose?' What do you have to lose, Tucson, by electing some Republicans to your city council? It can hardly get worse. How about if we work on making it better?"
Supreme Court Decision on Immigration
The conversation touched on a breaking Supreme Court decision allowing the Trump administration to revoke temporary protected status for 300,000 Venezuelans.
"The Trump administration has the authority to revoke this protected status," Smith explains. "I'm not saying everyone here from Venezuela is a criminal, but people need to understand that while crime in Venezuela is at record lows, crimes committed by Venezuelan illegal immigrants over the last three and a half years has risen about 300% in the United States."
Smith clarifies that many of those affected "are people largely who are coming here not to assimilate, not to be a part of American culture and be here illegally. These are people that are coming here to continue their illegal activity."
FBI Leadership and Upcoming Revelations
Smith shared insights about a recent interview with FBI Deputy Director Dan Bongino and Kash Patel on Fox News: "They talked about everything from Epstein... Bongino said that he has seen all the files and photos and Epstein did indeed kill himself."
She noted they also discussed "Russiagate" and "Russia collusion," with hints that "some big information is gonna be coming in the next couple of weeks." Smith speculates this might explain why "Hillary Clinton, who really spearheaded the whole Russia collusion thing, has been quite vocal and strident in the last few days... I think maybe she's getting a little nervous."
Mortgage Monday Update with Meg Swain
Current Mortgage Rates and Market Outlook
Though the Federal Reserve has not yet lowered interest rates, Meg Swain of Loan Depot reports there's optimism for future decreases: "They still are predicting that the rates are gonna come down three more times before the end of the year. They're saying that we're going to be at six or a little bit under by January of 2026."
Current rates as of mid-May 2025:
30-year fixed: 6.90%
15-year fixed: 6.08%
5-year ARMs: around 6.25%
Creative Financing Options
Swain highlights several creative financing alternatives for homebuyers in the current market:
5-Year ARMs (Adjustable Rate Mortgages): "It's stable and fixed for five years. Then after the five years, it has a start rate that can go up by at least two points minimum a year, with a max that can go up six points total," Swain explains. She emphasizes the importance of refinancing before the adjustment period: "My job would be to catch it before that fifth year is up and refinance them out of that loan before they put themselves into jeopardy."
Two-One Buydowns: "The first year, the start rate is at like 4.5%, then the second year is at 5.5%, and then it jumps up to the 30-year fixed for the remainder of the loan," Swain details. This program gives homebuyers "that little bit of a glide for 24 months" with a more comfortable payment initially.
First-Time Homebuyer Programs: "I have a client right now locking with LifeHouse. LifeHouse is amazing—it's Pima County, they give 4% toward the down payment of the house. They have to live in it for five years, and the interest rate today is 6%."
Advice for Homebuyers
Swain strongly recommends getting pre-qualified before house hunting: "You have to start with me at the beginning. Even if you're not ready exactly right now, it's an awesome idea to get an actual idea of what you can do."
She offers credit assistance and guidance on available programs: "If you have to work on any credit, I'm really strong with credit. They have to be able to see the road that they're gonna navigate."
Winn emphasizes this point: "The smartest thing you can do is not wait until you're out shopping for a home to get pre-qualified. There might be a student loan, a medical bill, something on your credit that you're gonna have to take time to get off your credit that you don't even know is there."
Potential homebuyers can reach Meg Swain at 520-471-8073 for more information on mortgage options.