- Ann Miletti, a financial expert on national TV, began her career as a public school teacher.
- Staggering medical debt from her son’s heart condition prompted her to switch careers to the financial industry.
- Miletti started in a call center and rose to become a portfolio manager in a male-dominated field.
- She credits her ability to read people, a skill not learned in business school, for her success.
Ann Miletti exudes poise and confidence talking about stocks, company quarterly earnings and trends in the economy on national television.
She’s appeared on CNBC and Bloomberg TV as head of equity investments for Allspring Global Investments based in Milwaukee.
And while Miletti sounds like a typical financial commentator discussing “the Fed,” “mag 7,” and “market cap”, few people know about her unusual career path. She started her career as a public school teacher and then pivoted and is now a financial expert with decades of experience.
“I ended up in this business all by mistake,” Miletti said.
Her dad worked for the railroad and her mom raised the family at home in Milwaukee.
“I always thought about being a teacher, and it was something I could really see myself doing,” Miletti said.
Challenges from staggering medical debt prompted a change
After graduating from Milwaukee Hamilton High School she went to the University of Wisconsin-Milwaukee and worked at the daycare at St. Luke’s Hospital.
She married her husband Tim during her junior year and after she graduated, she taught second grade for a semester. Then the couple found out she was pregnant.
Their son Ryan was born in 1990 and the doctors said the baby had significant heart problems and the family needed to stay in the hospital for surgery.
Ryan recovered, but the medical bills piled up.
“You were going to owe 20% of what the insurance didn’t pay,” Miletti recalls from that time. “By the time he was two-and-a-half, we were about $200,000 in debt on medical bills alone. We’re in our mid-20s and you’re staring at all of this debt.”
Miletti’s husband is a mechanic and with his income and a teacher’s salary, they decided that one of them needed to switch jobs to gain some hope of paying off the debt.
An opportunity at the Strong Investments call center
Miletti knew someone who worked in the mail room at Strong Investments in Menomonee Falls and applied for a job in the call center “after having like two business classes during my college career.”
“And not knowing anything about asset management, not knowing anything about the markets,” she said. “My parents had a bank account, but they never invested in the market.”
She was hired in 1991, working midnight to 8 a.m. taking calls from customers placing orders for trades on the following day. She fielded the overnight calls from the loading dock because, at the time, it was the only place that had a security camera. She also became a mom again, giving birth to a daughter.
Passed exams to become a registered representative
Miletti eventually passed three exams and became a registered representative, and in a position to bring home more money.
She took a part time job as the portfolio assistant working for Dick Weiss, who might not be known to the average Milwaukee resident, but in the finance world, was a force.
In 1999, the New York Times described Weiss as “superstitious – he carries a lucky pen, pencil and coins and wears an elephant hair bracelet. Soft-spoken, sometimes laconic, he can sound almost mystical when talking about markets.”
Miletti described Weiss as “an extremely difficult person to work for.”
“Our average turnover on our team, people survived like 2-and-a-half years. It was tough to work for him. He had very high expectations of himself and others,” Miletti said.
After six months on the job, Weiss was pushing her to be a full-time portfolio manager.
“My son was hitting the lifetime maximum of his million-dollar healthcare policy,” Miletti said, adding the family needed a plan for when they would hit the maximum for coverage. “He could have been uninsurable at 4-years-old and no one could’ve picked him up. Now there’s laws where you can’t discriminate (against pre-existing conditions).”
She took the job to get health insurance for her son.
“That was it,” Miletti said. “I never saw myself at that point, with our kids being so young, and still dealing with a sick son, that I would be the full-time (working parent). But we did it because it was the right thing for our family.”
And by 1994 she was co-portfolio manager with Weiss.
“I was super uncomfortable the whole time,” Miletti said. “I kept thinking like ‘I probably shouldn’t be doing this job. I’m not sure I know how to do this job.’ Except I was seeing success as an analyst. I had a really good hit rate on the stock recommendations that I made.”
Reading people became an important skill
Jon Baranko, chief investment officer for Allspring Global Investments, who has worked with Miletti for years, has marveled at her ascent in a male-dominated industry.
“For her to be one of the women who broke that glass ceiling during that period is pretty remarkable,” Baranko said. “The adversity that she managed through in her personal life actually translates pretty well into her ability to navigate adversity in her professional life. She has ability to compartmentalize things in a way that is actually productive. I really admire her.”
Although she didn’t go to a university that churns out Wall Street talent, she learned on her own about how to read people and understand their motivations.
“Reading people, seeing when you make them uncomfortable, when they feel comfortable to you, all of that was super important to me and I can read that,” Miletti said.
Others at the company saw her devotion to beating the competition but noticing details that are often overlooked.
“There’s an internal drive and fire in her to, at some level, prove people wrong. That challenge and that adversity at some level drove her,” Baranko said. “She picks up on things that I don’t necessarily pick up on and that helps me as a manager be a better manager.”
Battling insecurity and breakfast with Ted Turner
Despite her success, Miletti had a lingering feeling of insecurity: worried that every client could see through her or that her background would always be questioned.
With the encouragement of Weiss, she stayed on.
“At the same time, I don’t know if I would have made it without him because as much as he demanded, he also pushed me into opportunities I would have never raised my hand for,” Miletti said.
While Miletti was the primary breadwinner in the house, her husband Tim had more contact with their kids.
Miletti remembers being at an analyst breakfast with Ted Turner, the outspoken media-mogul billionaire owner of Turner Broadcasting in New York, when Turner was merging with Time Warner in the late 90s.
“I remember calling my husband at home and was telling him about this breakfast and was laughing. And I then I was like ‘So what did you do today?’ And he goes, ‘Well, I think Samantha is potty trained,’” Miletti remembers. “It was a microcosm of, who did the most important thing in our lives that day? He did. Like, potty training our daughter is life changing for us as parents.”
Being comfortable on national television
Strong Investments was acquired by Wells Fargo in 2005 and in 2021 it was sold to private equity and became Allspring.
“I literally worked for three different companies but never left,” Miletti said.
Miletti has trouble with the label “role model” because she doesn’t feel like she is one. But those who work with her do view her as that.
“The people that work for her trust her,” Baranko said. “And it creates an environment where people want to be here and they want to work here and they enjoy the culture.”
Baranko said Miletti’s impact can be seen in Allspring.
“When she entered the industry… it was a boys’ club,” Baranko said. “If you look at our executive team, actually… we have more women than men on that team which is somewhat unusual. But I think certainly for us, what we think is its terrific and a competitive advantage.”
For roughly the last 15 years she’s been taking her blue collar, mothers’ intuition on cable news to give her insights.
“I’m more confident now about answering the questions that I can answer and not trying to be an expert at everything,” Miletti said.
“I think in the early stages of doing media, I was trying to emulate things about people that I liked. Even early in my investment career it was like ‘Oh that person does this really well, I should try to do that.’ And it’s through failure in trying to be somebody you’re not that you realize I can only do it my way.”
Baranko remembers one particular television appearance when Miletti arrived in New York City at 2 a.m. to be on Bloomberg TV at 6 a.m.
Most people, even the most nerdy of analysts, would struggle discussing finances with such little sleep.
“And I had a brief call with her before that and she was as well put together as you could possibly imagine to go on TV and represent the firm,” Baranko said. “No one would’ve known she was operating on no sleep.”