Jack Boudreau

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Jack Boudreau I read the boring stuff so you don’t have to
Business // Finance // Tech
✉️: [email protected] To learn more, visit www.usehabits.com.

Jack Boudreau is the CEO and co-founder of Habits, a venture-backed marketplace built for the next generation of financial advice. Under Jack’s leadership, Habits is reimagining how individuals and families find financial advisors, combining behavioral science and a proprietary large language model to match users with the top 5 advisors that best align with their goals, lifestyle, and communication style. In 2024, Jack led Habits through an oversubscribed $1.1M pre-seed round with backing from Atlanta Ventures, Elevate Ventures, Flywheel Fund, and notable angels including the former Vice Chairman of J.P. Morgan, as well as operators from AMEX Ventures, Techstars, and more. Habits has since gained national recognition:
🏆 People’s Choice Award Winner at 1871’s Fintech Summit (out of 46 startups)
🏆 Best in Show at Morningstar’s Investor Conference FinTech Showcase

A passionate communicator and advocate for financial literacy, Jack reaches millions each month across TikTok, Instagram, and LinkedIn, helping a new generation navigate money, wealth, and life with more confidence.

10/17/2026

Half the “rich” people you’re jealous of might just be cosplaying.

Goldman Sachs Asset Management’s 2026 Retirement Survey (5,106 respondents ages 45 to 75) found that 46% of households earning over $500,000 typically pay only the minimum on their monthly credit card balances or less, nearly identical to households earning under $50,000 (47%). And 36.6% of $500k+ households say they primarily live paycheck to paycheck, which the survey defined as struggling to save and make progress on long-term goals. Eighty percent say they’ve had to delay a major financial goal.

High income and visible spending don’t tell you much about someone’s actual financial health. The designer bag, the luxury car, and the constant trips can just as easily sit on top of revolving debt and an empty savings account. If you’re paying your cards in full, slowly saving, and driving something boring that’s paid off, you may be further ahead than the people you’re comparing yourself to.

Source: Goldman Sachs Asset Management Retirement Survey & Insights Report 2026, via Fortune (Oct 13, 2026).

I’m Jack, I read the boring stuff so you don’t have to.

10/16/2026

Kroger isn’t cutting cashiers. It’s cutting the office.

The country’s largest supermarket chain plans to eliminate about 3,000 corporate roles over the next three years, roughly 37% of its 8,200 corporate employees, according to an internal memo from CEO Greg Foran. Store-level jobs aren’t part of the cuts. Foran wrote that Kroger has “more layers, more handoffs and more overhead than we need,” and that the company will lean on technology to reduce duplicative work, with savings going toward lower prices and frontline workers. The cuts come on top of roughly 1,000 corporate roles Kroger eliminated in 2025. The memo doesn’t specify how many roles technology or AI will directly replace, and details on which teams are affected are expected in the coming months.

For a generation told that a desk job was the safe job, it’s a strange reversal: the people on the store floor are being invested in, and the people in the corporate office are the ones getting cut.

Sources: Reuters, Grocery Dive, Cincinnati Business Courier, Fortune (Oct 12 to 14, 2026).

I’m Jack, I read the boring stuff so you don’t have to.

10/16/2026

Your next job interview might be with someone who doesn’t exist.

McKinsey confirmed to The Wall Street Journal that it’s piloting a 10-minute interview segment where candidates talk to an AI avatar playing a client, in one scenario, a mayor seeking advice on a major development project. The pilot is running this fall for undergraduates applying to business analyst roles in some North American offices, and hundreds of candidates may go through it. Human interviewers observe and make the hiring decision; the avatar asks questions but doesn’t score anyone. McKinsey says it could expand the format to other roles next year if the pilot works.

When the firm that advises half the Fortune 500 changes how it hires, other companies tend to follow. Today it’s a fake mayor at McKinsey. Tomorrow it might be your next interview.

Source: The Wall Street Journal (Oct 14, 2026), via The Verge.

I’m Jack, I read the boring stuff so you don’t have to.

10/15/2026

For the record, it’s a brownstone, I’m 31 and work in tech

10/15/2026

Americans feel worse about the economy right now than they did during the 2008 financial crisis, COVID, or 9/11.

The University of Michigan’s preliminary consumer sentiment index fell to 46.3 in October 2026, down from 48.1 in September. If it holds in the final reading on Oct 23, it’ll be the second-lowest level in the survey’s 74-year history, below the Great Recession (November 2008 came in at 55.3), the pandemic, 9/11, the 1970s oil crisis, and the Vietnam War. Americans’ view of current economic conditions fell 12% in a month to 44.7, an all-time low. The steepest declines came from lower-income households and people with little exposure to the stock market.

That’s the K-shaped economy in one survey. People with investments are riding the market. People living on a paycheck are absorbing higher prices, rates, and costs, without a crash or a headline to point to. Nothing broke. It just keeps costing more.

Source: University of Michigan Surveys of Consumers, preliminary October 2026 (via CNN and Bloomberg, Oct 9, 2026).

I’m Jack, I read the boring stuff so you don’t have to.

10/14/2026

Same same but different

10/14/2026

Going home for the holidays is officially a luxury item, and the airlines said the quiet part out loud.

Hopper’s forecast puts the average domestic Thanksgiving ticket around $400, up 31% from last year, with Christmas fares around $450, up 23%. Airlines point to jet fuel, which spiked after the war in Iran began, but when fuel prices fell after their April peak, Delta and other carriers didn’t lower fares. On CNBC, Delta CEO Ed Bastian said holiday fares “will be a function of what the market bears,” and that households in the top 40% by income “are basically our customers.” For a family of four, the trip home can easily cost more than a month’s car payment.

If you’re still booking: book soon, and if your schedule allows, depart Monday, Nov 23, the cheapest day to leave for Thanksgiving according to Points Path data.

Sources: Hopper forecast and Points Path via The Points Guy (Oct 9, 2026); CNN/CNBC interviews with Delta CEO Ed Bastian (Oct 9, 2026).

I’m Jack, I read the boring stuff so you don’t have to.

10/13/2026

Grew up with landlines, LimeWire, and carried quarters in our pockets.

Then witnessed iPhones, social media, App Store, and the world being a tap away.

Came after the financial crisis, but also got to experience our 20s before COVID lockdowns changed everything.

It doesn’t apply to everyone, but all things considered, we dodged a lot of bullets that millennials and Gen Z had to face.

10/13/2026

Travel sports used to mean a cool backpack. Now it costs more than some car payments.

The average U.S. sports family spent $1,016 on a child’s primary sport in 2024, up 46% since 2019, roughly double the rate of inflation, and about $1,500 per child across all sports. The biggest driver isn’t equipment anymore, it’s travel and lodging for out-of-town play, plus private lessons and camps. Collectively, American families spend more than $40 billion a year on youth sports, nearly double the NFL’s annual revenue. Kids from households earning $100,000+ are twice as likely to play travel sports as kids from homes earning under $50,000, and Project Play found parents spend more than three hours a day on their kids’ sports.

The saddest stat: research has found the average child quits organized sports by around age 11, most often because it stops being fun. The goal used to be a fun weekend and a cool hoodie. Somewhere along the way it became a scholarship pipeline, and the kids noticed.

Sources: Aspen Institute Project Play (State of Play 2025, National Youth Sports Parent Survey 2024/2025).

I’m Jack, I read the boring stuff so you don’t have to.

10/12/2026

A remote worker says she was fired for refusing to be photographed by her laptop we**am 160 times a day.

According to a lawsuit filed in New Jersey, the employee had worked remotely for Sutherland Healthcare Solutions since 2018. The company introduced an AI monitoring tool that captured a we**am photo about every three minutes, roughly 160 per eight-hour shift, using facial recognition to confirm she was at her workstation. She has lupus, and her doctor asked the company to make the monitoring less frequent because it was worsening her anxiety and condition. The suit alleges the company offered three options: accept the monitoring, commute to an office roughly three hours away each way, or be terminated. She was fired on Sept 8. Her attorneys say the company failed to engage in the accommodation process required under New Jersey law. Sutherland had not publicly responded, and there’s no ruling yet.

The bigger shift: the remote-work fight is moving from “come back” to “be watched.” New Jersey lawmakers are considering a bill requiring impact assessments before employers deploy AI monitoring tools.

Sources: Inc. (Oct 7, 2026), NJ Law Journal (Sept 26, 2026), Bergen Record.

I’m Jack, I read the boring stuff so you don’t have to.

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