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BEYOND THE CHAIR

Reimagining Retirement with Penelope

In a country where over 30 million small business owners are overlooked by traditional retirement platforms, Penelope is flipping the script. In this Beyond the Chair spotlight, we sit down with Jean Smart, Founder & CEO of Penelope, to talk about why the smallest businesses deserve the biggest innovation in retirement and how Penelope is delivering just that.

Penelope is a retirement savings platform designed for sole proprietors, micro-businesses, and the intermediaries who serve them. The company’s mission is simple but powerful: make retirement plans accessible, affordable, and ridiculously easy to implement for those who have historically been left out of the conversation.

“There are 34 million businesses in the U.S. Only 700,000 401(k) plans. That math is a problem we’re here to solve.”

Jean, a former Wall Street executive and now a mission-driven fintech leader, has built Penelope to remove the friction—technical, administrative, and emotional—that prevents small business owners from planning for their future.

An Intentional Path with TFC

Jean’s journey with The Founder’s Chair began at the Irvine event, where she immediately felt a different kind of energy. From the due diligence process to the in-person experience, Jean recalls the value of having investors truly listen—not just to her pitch, but to her data room, her story, and her strategy.

That connection led to more than investment. It unlocked strategic partnerships, pitch opportunities, and access to the broader insurtech ecosystem.

Tech-Forward, Human-Centered

Penelope’s platform is fully digital, purpose-built for ease of use, and supports white-labeled solutions for intermediaries—from banks and payroll providers to PEOs and TPAs. The team is preparing to onboard one of the largest national third-party administrators in the country, migrating their retirement services off a legacy platform and onto Penelope’s modern infrastructure.

What does it take to build a venture that lasts?

  • Take care of your health. Founding is a long game.

  • Forgive yourself. Mistakes are inevitable.

  • Find your people. The journey is lighter with support.

Est. 1919 · Des Moines, Iowa

HOTEL FORT DES MOINES

A century of stories, one remarkable address

Famous Guests
Scandals & Secrets
Firsts & Innovations
The Beginning
1922
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1922

Helen Keller rang in the New Year here, staying at the hotel while in Des Moines for performances over New Year's Eve.

1927
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1927

Babe Ruth and Lou Gehrig had breakfast here before an exhibition game. Two of baseball's greatest, at the same table, in Des Moines.

1927
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1927

Charles Lindbergh hosted a banquet here after his famous transatlantic flight. The menu featured boneless squab — reportedly a rare Des Moines delicacy at the time.

1933
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1933

Amelia Earhart visited the hotel to speak about her solo flight across the Atlantic — a rare chance for Iowans to hear her story firsthand.

1947
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1947

Mae West stayed here during her performance of "Come on Up" at the KRNT Radio Theater. One imagines she made an impression on the staff.

1959
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1959

Soviet Premier Nikita Khrushchev occupied the Presidential Suite during the height of the Cold War. This hotel has seen history made.

1960
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1960

JFK, LBJ, and Hubert Humphrey all attended dinner here and held a meeting on farm policy — three future or sitting presidents under one roof.

1980
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1980

Elizabeth Taylor stayed here during a Des Moines appearance. Hollywood glamour, right here in the heartland.

1980
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1980

Elizabeth Taylor stayed here during a Des Moines appearance. Hollywood glamour, right here in the heartland.

2003
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2003

Cher requested her own personal mattress be placed in room #1025. The hotel obliged. Room 1025 has never quite been the same.

2008
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2008

Barack Obama and Hillary Clinton both stayed here during the Iowa caucuses — rivals for the presidency, sharing the same address for a night.

1939
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1939

Police raided the Log Cabin Room on the 11th floor, seizing liquor and gambling equipment. The tip reportedly came from the men's own wives.

1927
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1927

When Lindbergh dined here post-transatlantic flight, he reportedly insisted on serving boneless squab, an extravagance that raised eyebrows across Iowa.

1959
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1959

The FBI monitored Khrushchev's stay closely. Guests on nearby floors reportedly had no idea who was sleeping down the hall.

1971
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1971

President Nixon greeted supporters in the lobby during his stay — a reminder that this hotel has always been where Iowa's political drama plays out.

1919
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1919

When it opened, every single room had a bathtub, purified chilled circulating water, and a window. Unheard of luxury for its era.

1938
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1938

The hotel announced the first air-conditioned guest room in Des Moines, a genuine technological milestone that made front-page news.

1953
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1953

100 rooms received TV sets in what was reportedly the largest single installation of televisions in Iowa at the time. The fee to operate yours? 25 cents.

1982
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1982

Governor Terry Branstad nominated the hotel to the National Register of Historic Places, cementing its place in Iowa's official history.

1919
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1919

The hotel opened on July 15, 1919, built for approximately $1.5 million and designed by the architectural firm Proudfoot, Bird & Rawson.

1919
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1919

Its opening was a statement of ambition: every room had a private bathtub, purified water, and a window. In 1919, this was genuinely extraordinary.

1974
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1974

Ronald Reagan attended WHO Radio's 50th anniversary celebration at the hotel, proof that Fort Des Moines has always been Iowa's premier gathering place.

2021
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2021

After major renovations, the hotel reopened as part of the Curio Collection by Hilton, a century of history, restored for the next hundred years.