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Building Better Business Relationships in the Age of AI


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Overview

John Jantsch talks with returning guest Zvi Band about something most business owners already sense: AI can churn out a thousand warm-sounding messages before breakfast, but people can still tell when a message sounds like a machine instead of a human.

Social feeds are filling up with algorithm-picked content and AI-generated noise, which is part of why relationships feel more urgent right now. Band and Jantsch talk through where AI earns its keep, capturing details, surfacing who to reach out to, and where it falls flat: judgment, timing, the soft skills that make someone want to work with you.

This one’s for solo consultants and agency owners who know relationships drive their business but haven’t yet built a system for maintaining them. Band shares a rough decay rate for relationships, the mistake most people make once they get serious about their network, and 1 simple move you can make this week to get started.

Guest Bio

Zvi Band is the founder of Contactually, the personal CRM that helped thousands of professionals stay on top of their networks (before Compass acquired the company in 2019). He wrote Success Is in Your Sphere: Leverage the Power of Relationships to Achieve Your Business Goals, and he’s spent the years since building Relatable, an AI-powered personal CRM built around a different premise: people aren’t leads. Band joined the Duct Tape Marketing Podcast once before, years ago, and returns now to talk about what’s changed since.

Key Takeaways

  • AI-assisted note-taking can free up mental bandwidth, so you’re fully present in a conversation instead of mentally cataloging details to remember later.
  • Relationships have a rough 6-month decay window. After that, people fall out of mind, not from anyone’s fault, but from being flooded with too much noise.
  • Before adopting any relationship-building system or tool, get clear on why those relationships matter to you right now, since that “why” changes as your goals shift.
  • Treat relationship maintenance like gardening: a few contacts a day beats 1 marathon organizing session that burns you out and goes stale again by morning.
  • As AI takes over administrative tasks, soft skills, like noticing whether someone genuinely connects with you and asking the right follow-up questions, become the real differentiator.

Great Moments

  • [00:01] – Jantsch opens with the line that frames the whole episode: people can tell when a message came from a prompt instead of a person, no matter how well the AI is trained.
  • [02:43] – Band explains why relationships feel more urgent now: better-tuned algorithms are hiding people’s posts from each other, and AI content overload is pushing people to tune out entire channels.
  • [06:09] – Band draws the line between Contactually’s original mind-share, warm-leads framework and Relatable’s premise that people aren’t leads.
  • [12:45] – Band describes Relatable as a relationship OS built to answer 3 questions: who do I know, who should I talk to today, and what should I do to nurture that relationship?
  • [20:04] – Band walks through organizing a messy contact list: get everyone into 1 place, then work through a handful of contacts every day instead of a single weekend marathon.

Memorable Quotes

  • “The more burden AI can take off our plate, the more cognitive capacity we have to care.” — Zvi Band
  • “AI can take the transcript and capture the details, but it’s not going to pick up the little things, like whether someone smiles when they’re talking to you. Only a human notices that.” — Zvi Band
  • “When someone finally decides to take their network seriously, very few make the jump from treating it like a New Year’s resolution to treating it as something they strategically execute on a regular basis, with a real system behind it.” — Zvi Band
  • “My guidance for people is to start with a clear why. Why is building relationships worth my time, my money, and the hours I could be spending with my family or elsewhere in my business?” — Zvi Band
  • “The magic number I’ve seen for how long you can go without staying in touch is around 6 months. Once you go past that, it’s nobody’s fault, people are just inundated with so much messaging that you fall out of their mind.” — Zvi Band

Resources

AI relationships, personal CRM, relationship building, Small Business Marketing, Zvi Band

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The Offer

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What Will Today’s Fed Rate Hike Mean for Mortgage Rates?


The Federal Reserve is almost guaranteed to hike rates today.

Odds are currently around 93%, per CME FedWatch, meaning it’s basically a sure thing.

In the Fed’s history, they’ve never defied odds like that so a ¼-point hike should be delivered as expected.

The impact on mortgage rates is less certain, as it always is because the Fed only deals with short-term rates.

But it wouldn’t shock me to see some relief for mortgage rates today, though the longer-term picture will remain data-driven as always.

Will the Fed Hike Lower Mortgage Rates?

First off, let’s quickly dispel the myth that the Fed sets mortgage rates. They don’t. They only set their overnight lending rate between banks.

This means if the Fed hikes, mortgage rates don’t automatically go up.

Similarly, if they cut, mortgage rates don’t automatically go down.

The only DIRECT impact on home lending is HELOCs, which are tied to the prime rate and do go up or down depending on a rate or hike of the federal funds rate (which correlates 100% with the prime rate).

So if you have a HELOC, it will likely rise by 0.25% because of today’s FOMC decision.

The good news is 0.25% shouldn’t affect the payment too deeply, though it’s still another blow with everything seemingly more expensive every day.

Now let’s talk about how the Fed does impact mortgage rates. It does so via Fed rate expectations.

The mortgage rate market reacts to what it thinks the Fed might do over time.

So if MBS investors think we’re entering a tightening cycle, they might demand higher yields (interest rates) as time goes on.

However, this isn’t a perfect science and it typically takes place before the actual Fed decision, not on the day of.

Fed Moves Often Counter Mortgage Rate Moves

This explains why mortgage rates and Fed rate hikes/cuts can diverge and often do.

In fact, on the day of many of the most recent Fed rate decisions, mortgage rates went the other way.

I pointed this out when they were hiking back in 2022-2023.

During that tightening cycle, the Fed hiked 11 consecutive times. It was painful for the economy and for mortgage rates, which also increased from sub-3% to as high as 8%.

However, that had more to do with the end of QE (the MBS buying program) and inflation than it did the Fed raising its overnight rate.

Interestingly, on nine of those 11 days, mortgage rates actually fell. So the Fed hiked, and mortgage rates went down!

While that might seem bizarre, especially when so many wrongly believe the Fed sets consumer mortgage rates, it makes perfect sense.

Remember, the market front-runs Fed decisions because they’re so obvious and telegraphed.

So when the actual news gets delivered, it’s often just a relief valve going off.

Similarly, when the Fed cuts, the market has already made its move lower. Mortgage rates go down in anticipation, often weeks before, so there isn’t another move lower on cut day.

Instead, mortgage rates may actually move higher on a cut day!

The Underlying Economic Data Matters Most, As Usual

Ultimately, it’s the underlying economic data that matters most, as it always does.

The Fed just works off this data, whether it’s the monthly jobs report or the PCE report (inflation gauge).

They aren’t really coming up with their own decisions independent of this data.

They are making monetary policy decisions based upon this data.

This means if you want to know which direction mortgage rates will go, simply follow the data.

As a rule of thumb, if the economy/prices are cooling, mortgage rates tend to go down.

If the economy is heating up (prices rising), mortgage rates tend to go up.

It’s pretty much as simple as that.

Aside from the seemingly foregone conclusion of a 1/4-point rate hike today, there is also the press conference with Fed chair Kevin Warsh today.

What he says also has the power to move mortgage rates, though again, it will all depend on the underlying economic data. And he will say as much.

(photo: k)

Colin Robertson
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How to Invest Your First Salary | A Beginner's Guide on Mutual Funds, SIPs, Gold | Dr Anuj Pachhel



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Kickstart your financial journey with Dr. Anuj Pachhel as he unveils key strategies for investing your first salary. This beginner’s guide covers mutual funds, SIPs, and gold, helping you make informed decisions to build a strong financial foundation. Perfect for young professionals eager to grow their wealth.

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Shiba Inu’s Bull Market Price Potential May Surprise You


Most meme coins don’t stick around long. Shiba Inu (SHIB +1.62%) is one of the rare exceptions. It launched in 2020 and peaked in 2021, but it’s still a recognizable name with a market cap of about $3 billion, and its price has increased 21% over the last month (as of Sept. 18).

It’s a welcome turnaround for a cryptocurrency that has mostly trended down since early 2025. Here’s what has changed recently for Shiba Inu and what kind of price potential it has.

Image source: Getty Images.

Regulatory wins could be tailwinds for Shiba Inu

Shiba Inu received good news on the regulatory front in March when the Securities and Exchange Commission (SEC) classified it, along with 15 other major cryptocurrencies, as digital commodities. That classification means Shiba Inu doesn’t fall under the SEC’s strict securities rules. Exchanges can offer Shiba Inu trading, and institutions can own the meme coin, without the risk of a lawsuit for listing or holding an unregistered security.

This also opens the door to the possibility that crypto exchange-traded funds (ETFs) could hold Shiba Inu. Although there haven’t been any applications for spot Shiba Inu ETFs so far, T. Rowe Price has filed with the SEC for permission to launch an active crypto ETF that would hold cryptocurrencies that fit its definition of eligible assets. Shiba Inu makes the list, alongside  Bitcoin, Ethereum, and XRP, among others.

In November, Shiba Inu was also the first meme coin to be added to Japan’s regulatory Green List. That put it in the same category as Bitcoin and Ethereum, and it means that Japanese crypto exchanges that want to list Shiba Inu can do so without any delays.

This meme coin has less upside than you might think

Shiba Inu trades at around $0.000005, and while fans of this cryptocurrency sometimes speculate it could reach $0.01, that’s not happening. There are about 589 trillion SHIB tokens in circulation, and if it reaches $0.01, Shiba Inu would have a market cap of $5.89 trillion. That’s more than double the value of the entire crypto market.

The regulatory wins and inclusion in T. Rowe Price’s proposed crypto ETF are both beneficial for Shiba Inu, but they haven’t moved the needle noticeably when the token is viewed through a wider lens. It’s still down 94% from the all-time high it set in 2021, and down by 60% over the past 12 months. Even though Shiba Inu has met certain regulatory standards, I question the level of institutional adoption there will be for a meme coin with a cartoon dog as its mascot.

Shiba Inu has occasionally gone on short upward runs, though their peaks have been lower since the big one in 2021. It reached $0.000045 in 2024, which is about nine times higher than its current price. It’s certainly in the realm of possibility that Shiba Inu could build up some hype again and manage to double, triple, or more. However, that’s entirely up to chance, and the likelihood of it happening is slim. I’d stay far away from Shiba Inu and stick to crypto investments with better odds of success.

Lyle Daly has positions in Bitcoin and Ethereum. The Motley Fool has positions in and recommends Bitcoin, Ethereum, T. Rowe Price Group, and XRP. The Motley Fool has a disclosure policy.

What Fed Rate Hikes Could Mean For Real Estate Investors to End the Year


As Al Pacino famously said in The Godfather III, “Just when I thought I was out, they pull me back in!”

Just when you thought you’d seen the end of high interest rates and that the Federal Reserve’s hand-picked new chair, Kevin Warsh, had a clear mandate to lower them, news of the Fed’s quarter-percentage-point rate hike has all of us investors shuttling back to 2022 in a nightmarish fever dream of negative cash flow. Will it never end?

A quick recap: Amid rising inflation sparked principally by the Iran war, the Federal Reserve raised interest rates for the first time in three years after its September meeting. For many investors, that will only add insult to injury because, at the time of writing, mortgage rates have already moved above 7%, so another rate hike will only add fuel to the fire.

However, for small investors looking to grow their portfolio, the obvious silver lining is that higher interest rates could lead to falling prices. For those with capital, the chance to nab a deal amid low competition and high rental demand is a golden opportunity.

Before we get ahead of ourselves, remember that the Fed does not directly set mortgage rates, which are more closely tied to long-term bond yields, inflation expectations, and demand for mortgage-backed securities. This helps explain why interest rates have been rising even though the Fed has not raised them until now. 

However, the Fed’s actions affect interest rates indirectly, and investors should keep in mind that mortgage rates will not necessarily rise or fall by the same amount as the federal funds rate, which is what the Fed’s rate changes directly correlate to.

A Sequel Many Times Over

We’ve all seen this movie before, only with different actors. First were Jerome Powell and Joe Biden, then Powell and Trump, and now Warsh and Trump. Despite the changing actors, the script is largely the same, and the outcome—the difficulty in getting leveraged rentals to cash flow or buyers to qualify for flips—remains.

“For buyers, a slower market can actually create opportunity,” mortgage executive Benjamin Cohen told Realtor.com. “There is more time to make a decision, more negotiating power, and potentially more flexibility from sellers.”

Not Every Housing Market is Slowing at the Same Pace

In addition, the housing market is not monolithic. According to Realtor.com, the Midwest offers fertile hunting ground for deals, with August pending sales down 4.3% from a year earlier. Pending sales were down 3.3% in the West. However, the same number is up 1.8% in the South, and the Northeast is up 1.1%, so deal-getting is very much a state-by-state scenario.

Prices also swing widely, with price reductions in the Northeast affecting 14.15% of listings, compared to over 20% in the West and South. So, in addition to the Fed’s move, investors will need to calculate potential cash flow based on negotiating power, along with all the usual metrics such as insurance, taxes, and rents.

That said, a Fed rate hike will have a major effect on all U.S. housing markets, as many retail owner-occupants will be eliminated from the discussion.

“Historically, rates are not that high, but we are also at the highest prices ever seen in many markets, so having rates this high on top of record high prices, we noticed that just going from a 6.75% rate to a 7% rate, it takes out a swath of buyers,” said Beau Keenan, broker-owner of Dickson RealtyKeenan, in a recent HousingWire report on market sentiment.

Cash Rules Everything Around Me

The Wu-Tang Clan’s hip-hop classic, “C.R.E.A.M. (Cash Rules Everything Around Me),” has proven more prophetic than even the rap legends could have imagined. For cash-ready buyers, rate hikes and falling prices are where fortunes are made. The extended homebuying malaise has opened pockets of real opportunity, with many motivated investors keen to take advantage.

“A lot of our buyers are coming in with equity from a home they just sold, or they’re paying cash outright, so a hike isn’t going to keep them away,” said Anna-Marie Ellison, vice president of sales at John R. Wood Properties Christie’s International Real Estate, to HousingWire, emphasizing how cash reserves and equity insulate top investors from rate movements.

There are several ways to access the cash you need to buy, even if you don’t have it sitting in your bank account:

  1. Sell assets (stock shares or other nonperforming real estate).
  2. Partner with a cash investor.
  3. Borrow from a family member at a low rate and refinance when feasible.
  4. Look for small multifamilies that you can house hack with an FHA loan.
  5. Look for seller financing opportunities or assumable mortgages.

Rental Demand Remains Strong, Urging an Investor Response

The increase in interest rates is a double-edged sword for investors. On one hand, conventional leverage investing, including BRRRRs, will be made more difficult. On the other, it keeps homebuyers out of the market, heightening rental demand and making purchases more likely to be absorbed quickly at maximum rents. 

This is reflected in recent data from the Federal Reserve Bank of New York, which shows consumer inflation expectations and rent growth remaining firm, reflecting the continued housing demand across urban and suburban markets.

Use Long-Term Cash-Flowing Rentals to Upgrade

For landlords who own long-term rentals and are locked in at low interest rates, as tempting as it is, now might not be the time to try creative borrowing strategies to buy more deals. Instead, using the cash flow from your existing rentals to make upgrades might be the safest and ultimately most profitable way forward. Stabilizing buildings with long-term, reliable tenants is far less risky and stressful than jumping into a turbulent real estate market, despite the temptation to do so.

Final Thoughts

For owners with multiple property portfolios who have been keen to keep stacking doors, now might be the time to take your foot off the gas and evaluate what you already have, what is working, and what’s not. If you were hoping to refinance high-rate loans by now but haven’t been able to, using cash flow to pay down balances, or—if you are unable to maintain some assets at a loss—selling and taking a haircut to preserve a smaller but healthier portfolio and lessen the day-to-day stress could be a good strategic move.

You can always live to fight another day, but life is short, and in the rush to get rich, it’s worth remembering to enjoy the journey, not just fixate on the destination.

agrees to leave Greenland with Denmark and boost US military presence



President Donald Trump announced Friday he has a deal with Denmark to bolster the U.S. military presence in Greenlandafter months of threatening to take the island by force from the NATO ally — an agreement that also keeps the Arctic territory in Denmark’s hands.

Trump in a social media post announcing the deal said the agreement “gives the United States permanent control over security, and all other needs, in Greenland, completely addressing ALL of our many U.S. concerns.”

He added that with the agreement his administration would “immediately” begin the process of developing a larger military presence on the mineral-rich Danish territory.

The office of Denmark’s prime minister, Mette Frederiksen, said the deal will be signed by all three governments next week during the United Nations General Assembly, but parliamentary action is still needed by the Danish and Greenland governments before it can be enforced.

In a statement she said “the agreement recognizes the sovereignty and territorial integrity” of Greenland and Denmark and upholds both people’s right “to self-determination.”

Greenland Prime Minister Jens-Frederik Nielsen said the emerging deal benefits all three governments and “recognizes Greenland’s interests and our place in the international cooperation.”

Allies pushed back on Trump’s call for the US to acquire Greenland

With his return to the White House last year, Trump called on Denmark to sell the island to the United States, while insisting Greenland is crucial for U.S. security. He pointedly wouldn’t rule out taking the island by military force, even though Denmark is a NATO ally of the U.S.

Denmark and Greenland repeatedly said the island is not for sale and condemned reports of the U.S. gathering intelligence there. The U.S. push for Greenland was also fiercely opposed by Russia and much of Europe.

But Trump with the announcement Friday suggested an understanding may have been reached that could bring an end to what was viewed as an existential crisis by Denmark.

“We look forward to working with the wonderful people of Denmark and Greenland toward a magnificent future with respect to this large, and highly strategic, parcel of land,” Trump said in his post. “We will be very protective of it!”

Trump had claimed the U.S. needs Greenland to deter threats from Russia and China, and has repeatedly made false claims of Chinese and Russian military forces lurking off the island’s coastline.

The agreement bans any non-NATO base in Greenland, limits adversaries from being able to make investments in Greenland and guarantees that China and Russia cannot have a base in Greenland, according to a State Department official who was not authorized to comment publicly and spoke on the condition of anonymity.

Secretary of State Marco Rubio cheered the statement as a “historic deal” and “huge win” for the United States.

“Greenland will forever be part of the strategic defense area of North America and exclude any adversary from it and the surrounding area,” Rubio said. “This deal permanently and completely addresses our national security concerns in Greenland.”

The island is crucial to North America’s defense

But the U.S. has long had a military presence in Greenland, holding several bases and installations through the Cold War before dialing back its presence.

The U.S. still operates the remote Pituffik Space Base in northwestern Greenland, which was built after the U.S. and Denmark signed the Defense of Greenland Treaty in 1951. It supports missile warning, missile defense and space surveillance operations for the U.S. and NATO.

Greenland sits off the northeastern coast of Canada, with more than two-thirds of its territory lying within the Arctic Circle. That has made it crucial to the defense of North America since World War II, when the U.S. occupied Greenland to ensure it didn’t fall into the hands of Nazi Germany and to protect vital North Atlantic shipping lanes.

Despite Trump’s repeated aggressive comments toward Denmark about Greenland, Danish officials had repeatedly made clear that they stood ready to work with the U.S. to expand the American military presence and strengthen U.S. commercial interests in Greenland.

Still, Trump’s repeated demands for Greenland and threats to take it by force rattled the NATO alliance and discomfited European allies, said Imran Bayoumi, an associate director at the Atlantic Council’s Scowcroft Center for Strategy and Security.

“I think Americans really underestimate how damaging it was for the image of the United States in Europe,” he said. “I think Greenlanders, Danes, Europeans saw this as a real attack on their sovereignty, and it’s going to take a lot of work to repair.”

Portage Finalizes $600M Fintech Venture Fund As Platform Hits $7 Billion


Portage, the fintech-focused investment platform within Sagard, has completed fundraising for its fourth venture vehicle, Portage Ventures IV, at roughly $600 million. The close, announced on September 16, 2026, arrives as the firm marks a decade of backing companies that are changing how financial services operate.

Combined with earlier strategies, the new capital lifts Portage’s assets under management to about $7 billion.

The firm began in 2016 as a specialist venture investor. Over the following years it broadened into growth equity and secondaries while remaining tightly focused on financial technology.

It now works with more than 140 companies across North America, and additional markets, and maintains offices in Canada, the United States, Europe, and the Middle East.

Parent platform Sagard oversees approximately $47 billion across several alternative strategies.

Portage Ventures IV will support founders from seed through Series C in wealth and asset management, banking, insurance, payments, and related segments.

The firm’s stated approach pairs capital with industry relationships, commercial introductions, and hands-on help in go-to-market, technology, partnerships, and transactions.

New strategic limited partners include Broadridge and Fifth Third Bank, a sign that established financial institutions see value in Portage’s specialized model.

Debevoise & Plimpton advised on the raise.

Co-founder and CEO Adam Felesky said the original thesis has only grown stronger.

Financial services, he argued, are still in the middle of a deep technology shift.

Wealth management in particular is encountering the kind of structural change banking experienced a decade earlier. Artificial intelligence is moving quickly into core institutional workflows, and legacy firms that once proceeded slowly are now spending more aggressively on modernization.

The companies Portage backs, he added, are building the infrastructure that makes that upgrade possible.

Stephanie Choo, general partner and co-head of Portage Ventures, framed the fund as a continuation of a decade-long effort to give fintech founders more than generic venture support.

In her view, the sector has its own dynamics, and founders benefit from an investor that already understands the landscape and can open doors across the industry.

Portage Ventures IV, she said, is meant to extend that partnership to the next wave of category-defining businesses.

The raise also sits against a wider Canadian backdrop of efforts to mobilize more private capital.

Portage itself has become more international over time; only a small share of recent venture investments from its later funds have been in Canadian companies, even as the platform still holds notable domestic names from earlier vintages.

The new pool of capital is intended to keep the firm active wherever it sees founders addressing institutional modernization, digitization of core financial products, and the practical application of AI inside banks, insurers, asset managers, and payment businesses.

For portfolio companies, Portage emphasizes a dedicated value-creation group rather than capital alone.

The platform’s pitch is that specialized knowledge plus a network of institutions, advisors, and commercial partners can shorten the path from product to scale.

It now remains to be seen whether that advantage holds through the next cycle. It will depend on execution and on how quickly incumbents continue to adopt outside technology.

The close of Portage Ventures IV is therefore both a routine fundraising milestone and a statement that a dedicated fintech platform still sees a large, unfinished opportunity in the rebuild of financial services.



Canada’s long-term bond auction draws highest yield since 2007




Canada auctioned long-term bonds at the highest yield in 19 years, as upside inflation risks create higher borrowing costs for governments around the world.

Widow of Roblox member allegedly taken for $6 million trying to buy out man from his escort contract



Marianne Flippo paid a male escort roughly $635,000 for eight months of exclusive companionship. Then, according to a lawsuit filed this week in Manhattan Supreme Court, he and his agency allegedly told her the only way to make the arrangement permanent was to pay $10 million to buy him out of his contract.

“I now recognize that I was the victim of a horrendous scheme by Starr who is a sociopath who lacks any conscience,” Flippo said in a sworn affirmation filed with the court.

The suit names the escort as Gregg Starr, an employee of an agency called Cowboys 4 Angels, and describes Marianne as newly widowed, managing money alone for the first time, and living with a rare genetic disorder that heightened her vulnerability to drugs and alcohol. Court documents allege Starr built her trust before defrauding her of nearly $6 million.

During a February 2026 trip to visit Starr’s mother, who suffered from dementia, two agency employees showed up unannounced and pressed Flippo to drink at lunch, despite knowing she was on medication for a recent surgery. The two ordered shots for the table, and after roughly five drinks, they produced an “Exit Agreement” requiring her to pay $10 million to end Starr’s ties to the agency.

“While I was drunk and confused (all of which was exacerbated by my medications and medical condition), Starr and Collins began to press me to sign the Exit Agreement,” Flippo said in her affirmation. She says she was taken to a hotel room and had never seen the document before that day. The agreement states that “under no circumstances has physical companionship been purchased for consideration.”

Flippo tried twice to wire the $10 million, but both attempts were independently flagged as suspected fraud, first by JPMorgan Chase and then through Westpac. Starr then directed her to open a joint account at Charles Schwab, which she says let him access funds without triggering a bank’s fraud review. She transferred $5.95 million into that account, and bank records filed with the court show Starr moved $5,719,010.37 of it into an account in his name alone within weeks, draining the balance to $12.61 by the end of June.

A circumstantial meeting

Flippo suffers from vascular Ehlers-Danlos syndrome, a rare genetic disorder that makes her blood vessels and organs prone to tearing and leaves her unusually sensitive to alcohol and medication. In December 2024, still grieving the loss of her husband, Chad, and needing to travel to Italy for a medication that had become unavailable in the U.S. because of the war in Ukraine, she asked a former colleague of Chad’s for help finding an Italian-speaking companion.

Chad joined Roblox when it was still a startup—years before it became the multibillion-dollar gaming platform used by tens of millions of children worldwide—earning multiple patents and building what Flippo describes as “a substantial amount of wealth.” Battling with depression, Chad died by suicide in August 2024. The two had been married 28 years, had three children, and were together since they met at 13.

Flippo was referred to Cowboys 4 Angels, which paired her with Starr. At first, she believed the company provided personal assistants but now says she learned it is an escort agency. Despite staying in separate rooms, Starr made advances toward her on the trip, which she turned down, and she paid the agency $27,000 for his assistance, split into three $9,000 payments she now believes were structured to avoid IRS reporting requirements. The agency kept calling afterward and told her Starr missed her. An employee named Bridget Collins became, in Flippo’s account, a trusted confidante who encouraged her to reconnect with him.

By March 2025, Flippo agreed to pay roughly $150,000 for Starr to be “exclusive” with her, but broke up with him that October after learning he was seeing an ex-girlfriend. But the agency kept calling, and she eventually agreed to speak with him again. By December 1, 2025, Starr moved into her Upper West Side apartment, and she signed a formal “Independent Contractor Agreement,” paying $368,000 for his companionship through May. The contract states Starr would serve as her “male companion” for an average of 16 days a month; that the arrangement “do[es] not include sexual acts of any kind;” and includes a clause requiring the money be returned if Starr cheated on her with that same ex-girlfriend. In January 2026, she paid another $90,000 to extend the exclusivity period.

Her illness runs through nearly every filing. People with vascular Ehlers-Danlos syndrome have an average life expectancy of 48 to 51 years; Flippo is 49. After surgery in early 2026, she was prescribed gabapentin and codeine, which she says left her “in a compromised mental state” for months, worsened by a severe infection in both arms. It was during this period, her complaint alleges, that Starr and Collins began telling her he needed $10 million to buy his way out of his contract.

“Unfortunately, I was not capable or perceptive enough to know these statements were false but, since I loved and trusted Starr, I relied on what he said. I now realize I was foolish,” Flippo said in her affirmation. And so the $5.95 million was transferred.

Flippo was already a client of Larry Hutcher for unrelated legal matters when Starr’s demand for an additional $4 million came up, according to her affirmation. Hutcher says he looked into what had happened and concluded she “was the victim of a horrific scheme.” She didn’t see it that way, and Hutcher said she was still “under the Svengali-like control of Starr.”

Starr, meanwhile, had retained his own attorney to draw up an agreement for the additional funds, and Hutcher arranged a July 7 meeting at his office to address it. Starr believed the meeting was to negotiate the $4 million; instead, Hutcher confronted him and said “he was shamelessly and criminally exploiting Marianne’s vulnerabilities and had defrauded her out of $5,950,000 and that no further money would be paid.” Starr, according to both affirmations, became visibly angry and threatened to abscond with the $5.95 million already taken if she didn’t pay the rest.

“In my fifty (50) years of practice I have never seen the type of outrageous conduct that exists in this case,” Hutcher said in his affirmation.